SCIENTIFIC ABSTRACT SHUYKIN, N.I. - SHUYKIN, N.I.

• Document Type: CREST
• Collection: Scientific Abstracts
• Document Number (FOIA) /ESDN (CREST): CIA-RDP86-00513R001550320005-0
• Release Decision: RIF
• Original Classification: S
• Document Page Count: 100
• Document Creation Date: November 2, 2016
• Document Release Date: August 31, 2001
• Sequence Number: 5
• Publication Date: December 31, 1967
• Content Type: SCIENTIFIC ABSTRACT

Thermal Isomerization of 2-Yiethyl-4.5-dihydrofuran to SOY/20-125-5-27/61
Methyl-cyclopropyl Ketone
ASSOCIATION% Institut, organicheskoy khimii im. N. D. Zelinakago Akademii
nauk SSSR (Institute of Organic Chemistry imeni N. D.
Zelinskiy of the Academy of Sciences,USSR)
SUBMITTED: February 5, 1959
Card 3/3

5(2).

AUTHORS: TimofeyeviL, le. A., 4h4,y -6-2-1161
SOV120-125
Corresponding Member, AS USSR,
Plotnikov, Yu. N., Kleymenova, V. M.
TITLE: Dehydrogenation of n-Hexane on an Aluminochromium Catalyst
(Degidrogenizatsiya n-geksana na alyumokhromovom katalizatore)
PERIODICAL: Doklady Akademii nauk SSSR, 1959, Vol 125, Nr 6, pp 1272-1274
(USSR)
ABSTRACT: A survey of publications on the reaction mentioned in the title
(Refs 1-2) shows that neither the instructions concerning the
reaction nor the yield of hexenes nor the formation of aromatic
hydrocarbons under the given conditions have been hitherto
discussed. Papers on the afore-mentioned reaction on oxide
catalysts lack. Further references follow (3-6). Table 1 shows
the data given in the publications concerning the reaction
mentioned in the title in the presence of chromium and with the
aromatization of n-heptane. This shows that catalyzates have
hitherto been obtained by various research workers which contained
considerably less unsaturated hydrocarbons than aromatic ones,
On the strength of their investigations carried out in the last
Card 1/3 years the authors drew the conclusion that it is possible to

Dehydrogenation of n-Hexane on an Aluminochromium SOV/20-125-6-27/61
Catalyst
change considerably the ratios of the yields of the two afore-
mentioned hydrocarbon typesv i.e. from 0-14 to 2.11 by changing
the production of the catalysts mentioned in the title,
furthermore, by the introduction of oxides of alkali metals,
finally by changing the instructions concerning the reaction.
The catalyst without alkaline additions was the best of all
catalysts investigated, as far as the maximum yields of unsatura-
ted hydrocarbons are concerned. It was produced by the
saturation of aluminum oxide with ammonium bichromate solution.
Unsaturated hydrocarbons with a yield of 2(rja' and not more than
14L benzene were obtained from n-hexane at 5000 and a rate of
passage of 0-5 h- 1. It was the authors' object to suppress the
aromatization even more in this investigation. All factors
were investigated for this purpose: temperature, rate of passage,
and individual parts of the catalyzate were analyzed etc. Table
2 and figure 1 show the results. The gas produced by the trans-
formations of n-hexane at 475 and 5000 contained 90.6-95-31,~r
hydrogen, up to 1.8 unsaturated hydrocarbons, and 2.7-7.5%
alkanes. The temperature rise within the afore-mentioned range
Card 2/3 increases the yield of hexenes only by 21i'~, that of benzene,

Dehydrogenation of n-Hexane on an Aluminochromium SOV/20-125-6-27/61
Catalyst
however, by 9-13114. Thus, it was found that the dehydrocycliza-
tion of n-hexane practically does not take place under the
given conditions, whereas hezenes are produced in rather con-
siderable quantities. The result is of general importance
since the authors succeeded in suppressing the aromatization
of an n-alkane which is capable of immediate dehydrocyclization
in the presence of an aluminochromium catalyst. The dehydrogena-
tion of n-hexane is rather considerable. There are 1 figure,
2 tables, and 8 references, 6 of which are Soviet.
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo Akademii nauk
SSSR (Institute of Organic Chemistry imeni N. D. Zelinakiy of
the Academy of Sciences USSR)
SUBMITTED: January 30, 1959
Card 3/3

5 (3)
AUTHORS: Correspondinj 1.,em,.ber SOV/2C-126-1-28/-6-22
AS USSR, Bekau..ri, if. G.
TITLE: Catalytic Pol~,cjcli~.at4on of Hicher Alkanes (Kataliticheskaya
politsikli-,atsiya vysshikh alkanov)
PERIODICAL: Doklady A%Mdemii nauk SSSR, 1959, Vol 126, lir 1, Pv 103 - 106
(USSR)
ABSTRACT: A _i~roup of scientists detectad at the same time (Refs 1-3) the
of the catalytic dehydrocyclization of alkanes vi
%I hich
have a chain of carb~,r. atoms in "he moieczzle (not less than 6).
This reaction was in7estiGated mainly in the case of hydrocar-
bc~ns ,f simplv composition. The-, Cave as final yiel-I b-anzene
,
tolu(--rie, and xyl,=_-:,3. Acc3rdin,~- to the mult plet thecry of
A. A. Balandin and othei- theorie,3 it could, however, be expect-
ed, that hiCher alkares of normal structure (bejinnin- with -the
n-decane) are bound to yield cn.-idensed systema of raphtlialene,
phenan-threne, and still more complicated pulycyoles under con-
ditions which favor dehydrocyclization, This is in fact the
case (Ref 4) (see scheme). a-Naphthalcnes can be partly or
completely isomeriz:!d into tho il-form in this reactizn. This
Card 1/4 formaticn is, however, possible with an intermediate stage of

Catalytic PoljcWcliz~~tt,.n LN.Elit,r A-J_Rnc-3 SCV/20--l 2(;--: --29162
a sabstftot,~,-d benze-c With a E,it-sequent closing of the side
chain (sr-O U.-heTf~'). This As ba3ed upon a provious paper of
the fl-rst a-,thor (Ref 5, s2e coheme). In the present paper
trans fox-1--A' ..J,ons c;f n-heptadecana and n-cctodeacana were in-
vestigated Ir. -the pra3erce of 0.5Fpf platinum preii.1-itated or.
alumirniml zxid.o and on 11guribri-a" (bleaching earth), or palla-
dium prcc!piltatid a' alr~rG ': and a hydro.-en pressure of 30 atm
(Ref C. Thc~ i.-t-al alkanes were inolated from the fraotion
'* c
190-350 f -,c,.e Sok.,;'jovogorskaya and Mirzaar-skaya petroleum
(Ref 7) and cieered. 8 liquid catalyzates -srere cb-
tained aE 41~e ressall. of the experiments wh-ch were tho--ughly
inventigatel accordIng- t-o an earlier deso-ribed (Ref 4) =ethod.
Vies,.- catalyzatr.is kicatained prz~ducts of the polymer-- zation, of
hydro,:-raf,.!,~ing, and, z~f the dehydrceyclization of the Initial
alkanee. Af4.4.0 Et t;pajj fraction which boils cut up to '1000has
beer- distill~,d off, L_-omatiz: hycirocarbons were isolated from
the rest of the Intli-vidual oatalyzates by mears of the chro-
mat n,-rL-.ph.-*Lc- rElisorptior. on silica gel cf the type ASM. By mzans
0 f 0-
f,.rther fracti...natinjx in. a r.-Itrocen atmrsphere a greater
content of -Iuxn,~, ind' -,c -la ir -1 p--ati-,Uln WaS o'htai-.ed
Card 2/4 1167~~Tbr nell ;vhich ~,ut --_-P tc 1500. Therefore,

Catalytic Polycy,~Iizstisn e-f SOVI,2r,-! 26--,, -23162
I(gumbi,-J-:-u-" 1'.9 i72)le ti aroma t4 Z-1 -1J
J. .LDn reacti-Dns. Figure
sh~)WG tht, propea7ticc C!f hydrocarbons boil
abcove 15(j'--. They lq,*-,.,c- a .)Iue--~:rveen fluorescence. The mixtLre
mas 6 zones respectively by ultra-,--*,;;I*t i.'Lum,-*-
natlo!. a nf ~Ufferent intensity ~-:.nd --olicr
(via-ve of the spect-ra showid that
the frantic-, i1 ~Y`.r
ss -1:1 is 4-q this ccmnecton most
aimilar ~m) and -.Is homolog-uae. The spectn2m cf the
fractic.- 17 'Fi-s 1:2 curelvo) J.-- similar to that ti-f a-:,..ethyl-
-n-aph-thal.-n-- (F~L-3 1 :.1 car--f-re), alt!i,)---,gh the two spectra lid
not Thiw alk.71 0--c-n7tn'.11rene3 witt, the side groups C - C
3 4
ax-'st 4r. t j,_ Tj ey rapi-tasent probably a. mixture of
Th - 4
ph,=anthrenes with a admixture
(see scl.-,eime) Th,~ continued. There are 1
figure, 1 and 7 S"viet, r9ferences.
Card 3/4

~Catllalytic Polycyclization of Higher Alkares SOV/20..126-1,-28/62
ASSOCIATION: Institut oi-ganicheskoy khimii iv.. N. D. Zelinskogo Alcademii
nauk SSSR (Institute of Organic Chemistry imeri N. D.
Zelinskiy of the Academy of Sciences,USSR). Institit khimll
im. P. G. Melikish-rili Akalemii nauk GruzSSR (Instultute of
Chemistry kmer.'. P. G. Molikishvili. of the Academy of Sciences,
Gruzinskaya SSR)
SUBMITTED: February 21, 11059
Card 4/4

50)
AUTHORS: Bellskiy, I. F., Sh SOV/20-127-1-23/65
Corresponding Member, AS USSR
TITLE: Catalytic Isomerization of S-Oxides (Tetrahydropyrans) to
Aliphatic Carbonyl Compounds (Kataliticheskaya izomerizatsiya
~T-okisey (tetragidropiranov) v alifaticheskiye karbonillnyye
soyedineniya)
PERIODICAL': Doklady Akademii nauk SSSRI 19599 Vol 127, Nr 1, pp 91-92
(USSR)
ABSTRACT:: Hitherto it has been assumed that the I- and &-oxides cannot
be isomerized by the opening of the ring to the compounds men-
tioned in the title, in contrast to the a-oxides. The authors
proved, however, (Ref 1) that this is possible as well in the
case of the d-oxides (tetrahydrofuran and its homologs) iD the
vapor phase on platinized charcoal at 2500. They are transformed
mainly into aliphatic ketones. The reaction of the &-oxides
mentioned in the title could be carried out as well with an
alkyl substituent in an a-position at 300-3500, as was ex-
pected. The corresponding aliphatic ketones (vield 70-80 %) and
alkahes (20-30 %.) are formed also in this case (see Scheme).
Card 1/2 This speaks in favor of the fact that the isomerization of

Catalytic Isomerization of 6-oxides (Tetrahvdro- SOV/20-127-1-23/65
pyrans) to Aliphatic Carbonyl Compounds
a-..&Ikyl-tetrahydropyrans-,proceeds like in the case of the
y-oxides, mainly by the opening of the ring of the C-0
bond which is farthest away from the alkj1 substituent
(bond 1-6). The reaction proceeds as smoothly as that of the
y-oxides; the reaction products are the same. An analogy with
the y-oxides exists with respect to the easiness of opening
(raskrytiye) of the ring as well. The transformation degree
of the d-oxides into ketone and aldehydes was higher than that
of the y-oxides (50-60 % per passage over the catalyst)9 since
their isomerization was carried out at a higher temperature.
There are 2 references, 1 of which is Soviet.
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo Akademii
nauk SSSR (Institute of organic Chemistry imeni ff. D. Zelinskiy
of the Academy of Sciences, USSR)
SUBMITTED: April 18, 1959
Card 2/2

5. (3) '
AUTHORS- Shuykin~ N. I., Corresponding Member SOV/20-127-2-34/70
AS USSR,-Bell'skiy, I. P.
TITLE: Hydrogenolysis of Carbonyl-containing -Furan Conpounds. Trans-
formation of Alkyl-acyl-furans Into Six-membered Carbocyclic
Compounds
PERIODICAL: Doklady Akademii nauk SSSH, 1959, Vol 127, Nr 2, PP 359-361 (USSR)
ABSTRACT: The direction of the hydrogenolysie of the furan ring depends on
various factors, in the first place on'the nature of the catalyst
and on the properties of the lateral substitutents (Refs 1-5)-
Strict conclusions on the influence of the latter on the mentioned
direction of the ring cleavage are possible only on the strength
of the comparison of experimental results obtained under equal
conditions of phase state and pressure. In a previous paper
(Ref 5) the authors found a ring aperture in the ctralkyl-furaus
on Pt-C only at the C-O-bond at normal pressure which is not
adjacent to the alkyl radical. Aliphatic ketones are formed here.
In the present paper the hydration reaction of pyromucic acid-
methyl-ester and 2-methyl-5-acetyl-furan was investigated under
conditions completely analogous to the last mentioned ones. In
Card 1/3 this case the carbonyl-containing groups influence decisively

HydrogenolysiB of Carbonyl-containing Furan Compounds. SOV/20-127-2-34/70
Transformation of Alkyl-acyl-furans Into Six-membered Carbocyclic Compounds
the direction of the aperture of the furan ring. The effect of
these groups is opposed to that of the alk-y1 radical. The hydro-
genolysis mentioned in the title proceeds in all substances
investigated easily and only at the C-0-bond adjacent to
carbonyl-containing groups. The primary products produced by this
are subjected to further changes in the vapor phase under the
hydration conditions. This hydration is interesting not only from
the theoretical point of view, but also opens new ways of
catalytic synthesis of valuable compounds on the iurfurol base.
The mentioned ester forms methyl butyrate with a yield of 35 %
in the hydration on Pt-C at 2750. This is a decarbonylization
product of the esters of the corresponding aldehyde acid produced
meanwhile (see Scheme)- 3-methyl-cyclohexanone, 3-methyl-
cyclohexanol as well as metacresol are produced as main products
from 2-mothyl-5-acetyl-furan under the mentioned hydration
conditions. This formation of carbocyclic compounds is based
upon profound structural changes in the molecule of this
heterocyclic ketone (2-methyl-5-acetyl-furan) and is certainly
a result of several subsequent reactions (see Scheme). Thus a
Card 2/3 hydro.-enolysis of the furan ring at the-C-0-bond adjacent to the

Hydrogenolysis of Carbonyl-containing Faran Compounds. SOY/20-127-2-34/70
Transformation of Alkyl-acyl-furans Into Six-membered Carbocyclic Compounds
carbonyl oroup proceeds first on Pt-C (iii contrast to Xi
catalysts). This leads to the formation of carbocyclic compounds.
A primary reduction of the carbonyl group in 2-methyl-5-acetyl-
furan takes as well place on Pt-C, however, to a much lower
extent than on Ni catalysts. An immediate transformation of I
into IV and V (see Scheme) has obviously a general importance
and may serve as a catalytic synthesis method of the alkyl-
cyclohexanones and alkyl-phenols from 2-alkyl-5-acyl-furans.
Finally the hydration apparatus, the reaction conditions, ana the 1tv-
sical owstaats of the obtained substances are described. There
are 6 references, 3 of which are Soviet.
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo Akademii nauk
SSSR (Institute of Organic Chemistry imeni N. D. Zelinskiy of
the Academy of Sciences, USSR)
SUBMITTED: April 18, 1959
Card 3/3

- / /
3)
-1-24 0
/ , .'7 j ~
AS USS_7~, -T;Cl I _`~i F

I 7-L E':
Isr mor.i z, .1 on ~jf r-0-TiC.Is [0 A7 ip, al, :~UT1,C-11YI C':-;FP0UrdS.
Zffo,~ t of t1c~ Tr~mpe fa 1.ur.,3 an', St - -o f The se Ci~mj.,our.,1 s
PERIODICAL. Doklady Akademii nauk SSSR,19599vol 127, Nr 4,PP 815-817 (USSR)
A:3 3 iC 2 T,7"_11. probl-ms arn this articie: (1) 7i.,'hat is the aotion
sed 'oy 'he 'anatli of Vhn --_erb~;n chain of tl-,L, all-Y1
pla~,-ecl n M-posit` or. on the rapas` fy o tl 0 tetrahydrof uran
L. _L D
oy3le to isovnerir~e, DceL-; this action -roceod in ti.0 I
ls
;Ji ttInS c-' 5-b-2--i-I), or in t'_p diroction II 'ttin-
.
2-1~o-ad, Scheme)? (2) is the effect of temperature
of the 1
.
on the Tolat Lve capaci ty of 'he I 5-bouds to to sfl- t
.1 -11-1 1~,ot-raliydrofurans ? (7) How dGes
Ly the of 06-;,
f 2 tetrahydrofurans develop, 4dcli
atiol~ 0 5
possess al':~-l radica1s witl-, numbers of carbon ator-le ?
(4) W11-1t, is t-1-.e direction in .,hic'L 'Llo isomerization of
2,2-dialkyl tetrahydrofuraiis takes pl,aco ? Table 1 shows
i.,Xpe-rimell"al resuIts. S 0 1 u + ~` 0 P_ S :
(1) The isomqrlzatlon of and
CG_n_L__1,[.jyj tetrah;(d2~o:rurarj. was mider eclual conditions
in the vaFor phase on platinized coal at 350c. I indicates

of r-Oxidos to Aliphahic Carbonyl 30V/20-1 ?7-4-24/6o
Effect of .-Le Temperature and Structure of These Compounds
A.
that the increasinG. number of carbon atoms in tLe oide chain of
a6-alkyl tetrahydrofurans increases the capacity of the C-0 bond
fo be split in the cycle i some -~izatio n. On the other hand, the
tendency of the C-0 bond 1,1r towards splitting decreases. The
yields of the isomerization products are Civen. In this case, a
pronounced dependence of tl-~e capacity of the tetrah-Ydrofuran
cycle to ioomerize on the length of the alkyl side r~~--dical is
noticeable in direction I or 11. (2) This problem was solved by
results obtained from the isomeriZation of ot-n-propyl tetrahydro-
furan at 250, 350, -and 4000. The relative quantities of n-hexane
and dipropyl ketone show an orientation of the isomerization of
Me tPtrah%drofuran cycle on the C-0 1,2- and 1,5-bond in
y
dependence on temperature. Table 1 further shows that the
re7a"ive capacity to iscj,-..ierize under the action of the ring
s,rlittinC at t1le C-0 bon,1 in the vicinity of the alkyl radical
i!-creases ,.-ith ris4ng tern...Verature. (3) In so far as the difference
of the C-0 bords 1,2 and 1,5 in their capacity to be split by the
i2ow-rization of thle substituted tettra-hyd-rofuran ring depends on
thc lencth of the tM:yl radlical ir. oC-position, it mi-ay be
exrected th-at this dif forence also oxists in tetra-
Card 2113 '-.ydrofurans containiw- various raimbers off' C-atoms. -as

of r-Oxiil..~s to Alipl-,-Ltic Carbor-3-1 S~,1,7/2)0- 1 ?7- 24 /60
Co m -~o unds -T-S-f-~ " o-f' t"-'e r a. ture -.in r! Zt:!-ljc t ure of Coq.,,ounds
L -r
In ne fso_-:,~-r~zation of diallkyl tet
.Lurans contaird-in- both alkyl ~--adicals i. a o n one a nd
thc~ sa-me C-a"-rri, I.'-.e rinds aye al-says 2pl-*;.t at the C-0 borld
4-
which is adlja-cont tq th,~ al',yi side radical. If cr t h
. I Ij JL -
,.~ c; a I:a-~ ii t -~ Leantime, this
(i r1bonylization of tilic.- aitlehyde for , c1 i -h
leads to t1ne '.rmatio;- of aliphat-It. hydrocarlociis.
ure table and r-,~!,,rnnces, -' of which nr.-- 3cvict.
ILIZtitUt - ` , zi .- -
SO,- 1 11 c 1! , S, -- 0h ~L m i i ; u . ~, . D . , ~~ 1 i 11 S! -. 0 g c M" a (I C- 1, na 1"'k.
SSS-1 Irstitulc. of Cr~~:inic Chcm-istr'-, imen! D. --jllLijsl:-iY Of the
3~-iencez, uss-)
SUBMITTED:
Card 31 171

00 66169
SOV/20-12-8-5-22/67
AUTHORS- Bellskiy, I. F., Shuykin, N. I., Corresponding Hernber, AS USSR
TITLh: A New Method for the Synthesis of Tetrahycirofuran Homologs
PERIOLICALt Doklady Akademii nauk 55SR, 1959, Vol 128, Nr 5, PP 9,,5-947 (USSR)
A.BSTa-.:,CT: The authors recall the niethods used so far for the above syn-
thesis (Refs 1-3). The new method worked out by the qathcrs is
described. It is based on a direct transformation of 1-furyl-
alkanols-3 into tetrahydrofurans of varying structure. This de-
pends on intermediate formation of 1,4-diols due to hydrogeno-
lysis of the furan cycle in the molecule of the 1-furyl-alkanols-3.
In hydrogenation in the vapor phase 1,4-diols are easily cyclized.
They separate water and form corresponding tetrahydrofarans. Two
cases are to be discussed %ith regard to the possibility of
synthesizing various homologs (mentioned in the title) due to
furfarol and aliphatic ketones: 1) Condensation of furfurol with
methylalkyl ketones. 2-n-proPYl-5-alkyl-tetrahydrofurans (III)
are formed (see Diagram). 2) Condensation of furfurol with ketones
of the type R-CH 2-1 -CH 2-R. 2-n-propyl-4,5-dialkyl-tetra-
0
Card 1/3 hydrofurans (VI) are formed ( see Diagram). The reaction LK

66169
A New I'lethod. for the Synthesis of Tetrahydrofuran S107/20-128-5-22/67
Homolo.as
mechanism mentioned above is proved by the structure of di-
and trialkyl-tetrahydrofurans for;aed by hydrogenation of
1-furyl-alkanols-3-in the vapor phase. This is a peculiar case
of hydrogenolysis of the furan cycle and of simultaneous
closure of the new tetrahydrofuran cycle by carbon atoms, three
of them having formed a side chain in the initial substance.
This fact offers many possibilities of Wnthesizing various
homologs of tetrahydrofuran since the side chain may vary ini
dependence on the str-.cture of the carbonyl-containing grou ~W .
a P
of the furan compound as well as the structure of the alipha-
tic ketone. The structure of this s-:*dc chain of 1-furyl-al-
kanols-3 is decisive for the structure of the new substituted
tetrahYdrofuran cycle being formed. Hydrogenolysis of the
furan cycle readily proceeds on various catalysts containing
-,etals of group VIII, e.g. on Pt-C and skeleton Ni-Zn, as well
as on a skeleton Cu-Al catalyst. The most important side
reactions on Pt-C are: a) isomerization of the homologs of
t,Arahydrofaran to aliphatic ketones (Ref 4). b) Formation
of lo4-dions. c) Hydrogenation of 1-furyl-allkanols-3 to 1-
lard 2/3 tetra'iydrofaryl-.alkanols-3. The authors obtained farfurylidene-
41-- 1

66169
A New :4ethod for the Synthesis of Tetrahydrofuran SOV/20-128-5-22/67
Homologs A
methyl-alkyl-ketones (I) by condensation of furfurol with
acetone, methylethyl ketone, and methyl-propyl ketone in the
presence of an NaOH solution. The yield was 70-M4- Conden-
sation with diethylketone was less satisfactory: only 50-55%
of the corresponding furfurylidene ketone (IV) was formed.
Hydrogenation of the latter substances to 1-furyl-alkanols-3
(II,V) gave a yield of up to 95~6- Four of these substances
are mentioned together with their constants. There are 4 ref-
erences, 3 of which are Soviet.
ASSOCIATION: Institat organicheskoy khimii im. 11. D. Zelinskogo Akademii
nauk SSSR (Institute of Or,,anic Chemistry.. imeni N. D. Ze-
linskiy of the Academy of Sciences, USSR)
SuB!.:ITTED: June 25, 1959
Card 3/3

6648F
'3 3 0 SOY/20-129-1-35/64
AUTHORS: Timofeyevaq Ye. A., Shuykinq N.I., Corresponding Member AS USSR9
Plotnikovq Yu. No, Ki-e-i ienova~q. ~.
TITLE: Dehydrogenation of n-Nonane on an Aluminum-Chromium Catalyst
PERIODICAL: Doklady Akademii nauk SSSRj 1959t Vol 129v Nr It pp 128-130
(USSR)
ABSTRACT: In connection with previous investigations (Refs 1, 2) the authors
wanted to dehydrogenate n-alkanes with higher molecular weight
on the catalyst mentioned in the title. Data from publications are
very scarce (Ref 3). The investigations were carried out at
various temperatures and volume rates. The method described
earlier (Ref 2) was applied. The gas formed due to reaction
contained 92-97% hydrogen, 1-5- 3-5% unsaturated and 1-0- 4-5%
saturated hydrocarbons. Table I and figure I show the results.
Table I shows that with a volume rate of 2.1 h-1 the olefin
content is increased from 8% to not more than 14-15% if the
temperature increases from 400 to 4750. At the same time the
content of aromatic hydrocarbons increases considerablyq namely
from traces to 15-16%. Thus a temperature of 4000 is optimum with
Card 1/2 regard to the selective reaction progress of dehydrogenation.
11K

MINACHEV, Kh.M.; SHUYKIN, N.I.; MARKOV, M.A.
Effect of the specific surface area of platiniwd aluminosilicate
on the degree of n.nonar-q conversions. Report No.2: Change
in the catalytic activity of platinized ablyninosilicate in the
course of the carrier treatment by water vapors. Izv.AN S&W Otd.
khim.nauk no.8:11+66-11+70 Ag 160. (MIR& 15:5)
1. Institut organicheskoy kbimii im. N.D.Zelinskogo AN SSSR.
(Honane) (Aluminosilicates) (Catalysis)

:1 -Ma
72 -0;0 Z.;AM
s V .3
'Jim
14 0
d
Jim, 1
0.4
t

PdAJi I BOOK WLADITATICS SOV/49111
Nezhvuzovskoye 910VOSAChanlye p0 khImll nefti. Moscow, 1956.
Sbornik trudQv M4zhvuzovskogo saveszenanlyl po ~;hlmll nerti
(Collection of Transactions of t." Inter-Univer3ity Con-
ference on Petroleum CnemIstry) [Moscow) Izd-vo Moak.
univ., 1960. 313 P. Errata slip Inserted. 1,6Go copies
printed.
organizing ccmaittea or the Conference: Chalman: B. A.
Uzanskly, Academician., Vlce-Chairozm: S. 1. Khromov,
D"ent; 0. M. Panchankov. Professor, A, P. flat*. Pro-
fessor; Secretary. Te. S. BalenkovA~ Scientific Workdr.
141torial Board: Reap. Ed.: A. P. ?!are; 1. V. Goatun-
okay&. I. R. Tits-Skvorta,;v4, L. A. FrIvanskaya.
PURPOSE, This collection of articlea Is Intended Car the
teaching atarr or universities and schools or higher ad.
ucati on training specialists for the petroleum anti patrol-
Anua-rerIning industries.
Card 1/7
COVERAaz; The collection Includes articles dealing with the
present state of the petroleum industry. the scientific
research problems In petroleum chemistryo the chemistry
or petroleum. the COCIP031tion or petroleum and petroleum
products, the sciontirle principles of refining petroleum
Into motor rueln and lubricants, and the manufacture of
synthetic products from hydrociurbon gists and petroleum.
One article discusses the affect of chemical composition
and additives an fuel combustion In jet engines. The ma-
toriAl Was presented at the In:*r-UnIversity Conference
on Patrol*um Chemistry, he Id at tne Moscow State Universi-
ty Imeni M. V. 14monosov November 26-25-. 19~,,Q. No person-
&LItlea are mentioned. References accompany most of the
articles.
?ABLt UP CONTIMSs Non* given
The Authors and the titles of articles A" as follows:
Xntrodu4tion by B. A. Kazanskly, Academician
Card 2/7

S/595/60/ooo/ooo/oll/014
E040/E435
AUTHORS: Shuykin, N.I., Naryshkina, T.I.
TITLE: Catalytic synthesis of cyclopentadiene series of
hydrocarbons
SOURCE: Vsesoyuznoye soveshcbaniye po khimicheskoy
pererabotke neftyanykh uglevodorodov v poluprodukty
dlya sinteza volokon i plasticheski-kh mass. Baku, 1957
Baku, Izd-vo AN Azerb, SSR, 196o. 249-259
TEXT: In view of the importance of hydrocarbons of the cyclo-
pentadiene series because of their high reactivity, the present
authors studied their production 1) by catalytic dehydrocyclization
of diolefinic hydrocarbons and 2) by catalytic dehydrogenation of
five-member cyclanes into cyclenes. The optimum dehydrocyclization
conditions for piperylene were found to be at 6000C under reduced
pressure (20 to 25 mm Hg). Alumino-chrome-potassium catalyst was
found to give the highest yield of (1) and to have a useful active
life of up to 80 hours. A much higher yield of 47% was obtained
under the same reaction conditions in dehydrocyclization of
piperylene-3-methylpentadiene-1,3 to methylcyclopentadiene.
2-ethylbutadiene formed easily methylcyclopentadiene with
Card l/ 4

S/595/6o/ooo/ooo/oll/oi4
Catalytic synthesis of ... Eo40/E435
38% yield. The reaction is sensitive to pressure.
Dehydrocyclization of piperylene under a slightly reduced pressure
leads to some isomerization to isoprene and pentadiene-1.4 and to
hydrogenation giving pentenes and 2-methylbutene-1. A sonsiderable
quantity of aromatic hydrocarbons is formed if the reaction is
carried out under atmospheric pressure: at 600'C and atm pressure
piperylene gives a 5Mo yield of benzole, toluol and xylol. By
carrying out the reaction at reduced pressure and re-.:~ytling the
non-reacted piperylene, the yield of (1) is raised to 40%. The
two methods of M preparation were studied on pentadiene-.1.3..
3-methylpentadiene-1,3 and 2--ethylbutadiene--1,3 (dehydrocycl-lzaticii
method) and on cyclopentene, methylcyclopentene and zy:;lopentane
(dehydrogenation method). The reactions were c;arried out in a
quartz tube, 18 mm in diameter at 500 to 600'C, the pressure being
varied from atmospheric to 20 to 25 mm Hg, The yield of (1) in
the reaction products was determined using B.N.Afanas7yev's method
(Ref.1; Zavodskaya laboratoriya., no.12, 1948, 1493). The
catalysate was fractionated and analysed by optical and ~hem;.,_al
methods. Evaluation was made of a number of catalysts but a
Ild t 0 a
16 (1.4%)* K20 (2
mixture of A1203 (84() + Cr203
Card 2/4

S/595/60/000/000/011/01"
Catalytic synthesis of E040/E435
specific surface of 97.9 cm2/g was found to be the most
Complete results are reported including data for the compcsiti~'n z'
all catalysts tried and the reaction products identified in the
catalysate. It is concluded that cyclopentadiene and its
homologues can be obtained by dehydrocyclization of diene hydro-
c_arbons of the aliphatic series and dehydrogenation of five-mf-mber
,cyclanes and cyclenes, the yield of (I) in dehydrocyclization of
alkadienes being 18 to 47%. Dehydrogenation of cyclenes gives up
to 58% of (I). Under the same conditions, cyclopentane and
methylcyclopentane are dehydrogenated in 14 to 311% yield, The
optimum conditions for cycloalkadiene formation from the above
hydrocarbons are at 600"C and 20 to 25 mm Hg. Acknowledgment-3 are
expressed to Yu.P.Yegorov for his assistance. Academician
S.V.Lebedev is mentioned in connection with his method for the
production of divinyl. There are I figure, 5 tables and
41 references: 14 Soviet-bloc, I English translation from Sovie,
publication and 26 non-Soviet-bloc, The four most recent
references to English lan,~uagve publications read as follows~
C~A~, 47, 6645 11953
_o, Joiies T,G~ US Patent 2,636-o66, 1953,
Card 3/4

S/595/60/000/000/011/014
Catalyti.c synthesis of Eo4o/E435
Ref,27 Kennedy RM., Hetzel S-J, Industr. Engng. Chem- 421: 19~-9
71-
5'1-1 Ref.28. Lodge W.V_ Walters W.D. J~ Am~ Chem, So:-.
4,51. Ref,29, Mundy C.1-7- J. Oil Colour, Chemxst, Assoc, 38
211)_

S/595/60/000/000/012/014
E196/E485
AUTHORS. Shuykin, N.I., Timofeyeva, Ye.A., Dobrynina, T,P,
TITLE., Contact.-catalytic dehydrogenation of pentanes
SOURCEg Vsesoyuznoye soveshchaniye po khimicheakoy
pererabotke neftyanykh uglevodorodov v poluprodukty
dlya sinteza volokort i plasticheskikh mass, Baku, 1957,
Baku, Izd-.vo AN Azerb. SSR, ig6o. 261-265
TEXT: In earlier published work, the authors found tbat
dehydrogenation of n-pentane using catalyst composed of oxides of
Al, Cr and Mg in molar ratio 45:30:25 at 500 to 550'C with space
-elocity of 1.2 hr-1 gave condensate containing 21 to 26% pentenes,
1.e. 18 to 19% of the transformed pentano. A more effective
catalyst of the composition A1203, Cr203, K20 (90.7:5.693.7 mol %)
gave from isopentane at 5270C an 87% yield of catalysate with an
olefin content of 38%, consisting of all isomeric isopentenes,
mainly 2-methyl-2-butene and also n-pentane (0), isoprene (2%)
and small quantities of pentene-1, pentene-2 and toluene. Under
identical conditions, n-pentane was dehydrogenated in 88% yield to
a product containing 31% of olefins including: pentene-.2 (28%).,
Card 1/ 3

S/595/60/000/000/012/014
Contact-catalytic dehydrogenation E196/E485
pentene-1 (0), also isopentane (3%) and pentadienes kl%), The
yield is increased by 3 to 4% if the catalyst is reactivated with
hydrogen. The same catalyst was used to study the effect of
temperature., space velocity and the duration of working cy-les.,
The catalyst's activity is claimed to be such that reaction
equilibrium is reached at 500 to 5500C with a space velocity of
O~3 to 0,5 hr-l~ The effect of space velo-city on the yield of
pentenes varies with temperature, At 500'C the yield of isopentenes
is reduced from 39 to 27 mol % when space velocity rises from 0.5
to 1.1 hr-l, The corresponding reduction in the yield of
isopentenes is 46 to 42% at 527'C and none at 550'C. At 575C
space velocity can be varied from 0.3 to 1.7 hr-1 withiout effe_~t
on the yield, The catalyst's active life decreases with increase
in reaction temperature, In order, to obtain maximum quantity of
isopentenes without regard to the usage of raw materials, high
reaction temperature (550'C) and high space velocity (Izl to
1.7 hr-1) are recommended, If, however, the object -is to get tht
highest conversion of isopentane to isopentene. then the lower
temperatures may give more economical operation. There are
Card 2 /3

5/595/60/000/000/012/014
Contact-catalytic dehydrogenation. .- E196/E485
2 figureg, 2 tables and 5 referencesi 4 Soviet-bloc and 1 non
Soviet-bloc,
Card 3/3

5(0)
AUTHOR- Shuykin, N.10, Corresponding S/030/60/000,10111026/067
Member of the;kcademy of Sciences B015/3008
USSR
TITLE: Scientific Conference Devoted to Petroleum- and Coal Chemistry
PERIODICAL: Vestnik Akademii nauk SSSR, 1960, Nr 1, PP 73-74 (USSR)
ABSTRA,CT: The Conference was held at the Technical School of Higher
Education for Chemistry Leuna-gerseburg (Eastern Germany)
from October I to 5, 1959~ K. Winkler, Minister for the
Chemical Industry of Eastern Germany, reported on the chemical
industry in the Republic and the establishment of a number of
new productions which are based mainly on the chemical proces-
sing of petroleum,, V. Blauhut described the essential problems
which resulted in connection with the further development of
petroleum.- and coal chemistry. He underlined the utility of
a scientific-technical cooperation with the USSR and the
people's democracies, Reports of scientists from Eastern
Germany are mentioned further. The author jointly with
I.F~ Bellskiy on behalf of the Soviet scientists reported on
Card 1/2 the catalytic hydrogenolysii~in the series of the furfuran4
I

Scientific Conference Devoted to Petroleum- s/1030/60/000/01/026/067
and Coal Chemistry B015/BO08
compounds~ The delegates visited the -Chemical Kombinat "Leuna"
after the conclusion of the Conference,
wel
-
Card 2/2

IJ
Lt1

Catalytic Conversions of ;)-C,.-r--ee~e Over -, 8 0 -"' 0 ~;
Platir.11.zed Alurrina Unde- !~lrdrogen P!-ess.,re Sov 116-2 - 6 0 - 1 - 10
1
ASSOCIATION:
SUBMITTED:
There are 9 reCerences, 6 Soviet, 3 U.S. The 3 U.S.
references are: Haen,--el,V , Donaldson, G. R., Induztr.
and Engng. Chem , 42, 582 (10F-W; Pitts, P. M., Connor,
"~ j -
j. E., Leum.. L. M.. industr, and Fno*ng, Chem., 41, 7 70
t
a Chem, Rev., .
,1955); Szw r M. 47. 171 (1950).
N. D. Zelinskly Tnstitute of Organic Chemistry of the
Academy of Sciences of the USSR (Institut organicheskoy
khIml'- imeni N. D. Zelir-skogQ Akademli nauk SSSR)
June 6, 1950
1 Card 313

r
V.
A U 0 !_"S)
-1 oni De hy d n'-, tr Il
T ITI E Corn,,nuillcat j c, CL- Me thy ltetra-
hydropyr."!rl Over, 'rlO,I-Al_0l C-j y:1
I
FE H I OD I C A 1, 01
of Cl -me thy 111(! ral ly(h.opl, r,,an (1) wndt~,r the
,s of'
condit-lor, Its dehydi,atlon ov;-,:- T 1, 0,, - A J0, ca'. ly t
",-)-,)0 -,a n d
W
-0. 1101-tv
!;f o, If-Y 'i U(I,
it.c
I cI 1,
IL A +
cl I'cl 1clIcif ClICII,

I c
:i 0 C;tt
I I t of' th~~ on." "i vo v".ri rl
F-1,1~,~ t Iona I d :10 t ll Ia t lon
of' th~, Products of' cata-
1,; of' e p;- I rm-.~ n "I , conduc-
;-,'u 41:0 (a) amount
Al Al

TL

G
K
.
9, h
9,7
5 3 n 5

3o
o"-,
" 1.3
to,:1
- 1.1,7 1 .0
6110 90 o.:1 ,,,s 1; .1.3 1 , 1; 27, G
k t.: Lj
-:e Velocity,
I
f run
j

0

I I -~llld t *,,~.'~:,- 1`l(-",- U.S
Th- U.S.
J . C l .(~m S o It son
80"' . .
1.'.
Bul.clh,
W. F).

,ft
1" ! u1, O
lc".,111~- cllelfi ktr-y :i ,-*Lld,-~l'liy
. f
'..I!,,ikoco Akaderrill tiaul~

s/o62/60/000/03/05/007
BO08/BOO6
AUTHORS: Shuykin. N. I., Tulupovaq Ye. D.
TITLE: Preparation of Aronatio HydrocarbonalFrom Tuymazy Gasoline
by Two-stage Aromatization
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheakikh
nauk, 1960, No. 3, PP- 490-494
TEXT: The possibility of preparation of toluene and xylenes from V/
Tuymazy gasoline with a low anti-knock value was investigated. The two-
stage aromatization method was applied for the heptane-methyl cyclohexane
fraction boiling point 91 1030C) and the octane-dimethyl cyclohexane
fraction ~boiling point 117 1270C). The fractions investigated were
obtained by rectification. The properties of the initial material and the
fractions obtained are listed in Table 1. The results obtained by two-
stage aromatization of the heptane-methyl cyclohexane- and octane-dimethyl
cyclohexane fractions, as well as of Tuymazy unrectified gasoline and the
residue remaining after distillation of the fraction boiling at 91 - 1030C
Card 1/3

Preparation of Aromatic Hydrocarbons From S/062/60/000/03/05/00-i
Tuymazy Gasoline by Two-stage Aromatization BOOB/BO06
are tabulated in Table 2. Changes in the activity of the catalyst during
long-time dehydration are illustrated in Figs. 1 and 2. Platinized
carbon containing 10% finely dispersed platinum and nickel - copper -
aluminum oxide (67.5% Ni + 2-5% Cu + 30% A1203) were used as catalysts.
Tests showed that the toluene content of the heptane-methyl cyclo-
hexane fraction can be increased from 5 to 30% by volume by two-stage
aromatization in the presence of 10% platinized carbon. A Ni-Cu.-A120
catalyst can also be used for dehydrogenizing hexamethylene hydrocarLns.
It is less stable than the platinized carbon catalyst, but can be re-
generated in situ. In the case of the octane-dimethyl cyclohexane
fraction (boiling point 117 - 1270C) of the Tuymazy gasoline, the
content of aromatic hydrocarbons, particularly that of xylenes, can be
increased from 8 to 33% by volume by two-stage aromatization. The
xylene content alone is increased by 17% owing to isomerization of
5-membered cycloparaffins to form 6-membered cycloparaffins. Removal of
the fraction boiling at 91-1030C does not lower the anti-knock value of
the residual Tuymazy gasoline. There are 2 figures, 2 tables, and 15
references, 12 of which are Soviet,
Card 2/3

Preparation of Aromatic Hydrocarbons From S/062j6O/OOO/O3/O5/OO7
Tuymazy Gasoline by Two-stage Aromatization Boo8/Boo6
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo k1
Akademii nauk SSSR (I%stitute of OrK n*c (I. . v imeni
N. D. Zelinskiy of the Academy of Sciences, USS )
SUBMITTED: July 18, 1958
Card 3/3

MINACHEV, Kh.M.; SHUYKIN, N.I.; MAMOV. M.A.
Bffect of the specific surface of a platinized aluminosilicate on
the degree of u-nonane conversion. Report -Wo.l: Change in the
activity of platinized aluminosilicate in the course of the
treatment of the carrier with hydrogen. Izv.Ll SSSR Otd.khim.
nauk no-5:907-912 Nr 160. (MIRA 13:6)
1. Institut organicheskoy khimii imeni N.D. Zelinskogo Ak&demii
nauk SSSR.
(Aluminosilicates) (Platinum) (No"Ane)

? I I
SALIMOV, M.A~.-. VIKTOF.OVA, Ye,A,.; :,MVJUNSK2..YA, L. L.; SIIUYKIN, N: I
larared spectra of alkyl.phenols and their simple ethers. Azerb.
k.him.zhur, no~6-'99-105 t60. (!-UFA 14,1- 8)
(Phenol-Speptra)

SHMIN, N. I.; POZDNYKK, N.A.
Catalytic alkylation of tetralin. Report Mo.l: ADWIation of
tetralin with amylenes. Izv.AN SSSR.Otd.kbim.nauk no.6:
lo94-lo97 ii 16o. (KIRA 13:7)
1. Institut organicheskoy khimii imeni N.D.Zelinskogo Akademii
nauk SSSR.
(Naphthalene) (Pentens) (Alkylation)

AUTHORS: Shuykin, N. I., Pozdnyak, N. A.,
TITLE: Catalytic Alkylationlof Tetralinl.
of Tetralin With Heptene-1
3106 9/000/07/06/007
B015PBO254
Shlyapochnikov, V. A.
Information 2. Alkylation
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh naukq
1960, No. 7, PP- 1254-1257
TEXT: The authors alkylated Tetralin with heptene-1 in a continuous-flow
apparatus using two types of catalysts. In one series of experiments they
used an aluminum oxide treated with hydrofluoric acid (10% and 20% HF),
in the other series an aluminosilicate catalyst; the experiments were
carried out at atmospheric and increased pressure and at different tempera-
tu.res (Tables 1-3, influence of different test conditions). In the cata-
lytic alkylation, a mixture of P-heptyl Tetralin and Pgpl-diheptyl Tetralin
was obtained. The given data show that with the aluminosilicate catalyst
the following o8timum conditions exist: volume velocity 0.25 hours~l,
temperature 200 C, pressure 10 atm, molar ratio Tetralin : heptene-1
= 2 : 1. Under these conditions, the yield in P-heptyl Tetralin is 48.7%
ut"ll
Card 1/2

M2
Catalytic Alkylation of Tetralin. Information 2. S/062 0/000/07/06/007
Alkylation of Tetralin With Heptene-1 BO15/BO54
with respect to heptene-1, and 24.3% with respect to Tetralin. The infra-
red spectra of the heptyl Tetralin synthesized showed that the heptyl
group lies in the P-position. B. A. Kazanskiy, G. A. Tarasova, and
0. D. Sterligov are mentioned in the paper. There are 3 tables and
6 references: 3 Soviet and 3 American.
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo Akademii
nauk SSSR
(Institute of Organic Chemistry imeni N. D. Zelinskiy of
t~e Academy of Sciences, USSR)
SUBMITTED: December 10, 195
Card 2/2

86413
I Ts S/062/60/000/008/021/033/xx
1~1.sglo 2209 BO13/BO55

AUTHORS: Popov, M. A. and_~~ I.
TITLE: Catalytic Synthesis of Nitriles. Communication 3- Prepara-
tion of Aromatic Nitriles
PERIODICAL: I2vestiya Akademii nauk SSSR. Ot' deleniye khimicheskikh nauk,
1960, No. 8, pp. 1451-1456
TEXT: The present paper deals with the catalytic synthesis of nitriles
from aromatic alcohols and ammonia in the presence of nickel/aluminum-
oxide catalysts. The investigation was undertaken with a view to finding
the most suitable conditions of synthesJs, and tc study the effect of the
phenyl radical on ihe composition of the reaction products. Experiments
were performed with benzy! alcohol, P-phenyl ethanol and y-phenyl propa-
nol. The reaction was carried out at 270-3900C and atmospheric pressure
in a continuous system. The catalysts contained 3, 7.5 and 15"' reduced
nickel precipitated on aluminum oxide. Catalyst preparation and experimen-
tal apparatus have been described in Ref. 7. Systematic experiments showed
that at 3900C, benzonitrile is formed from ammonia and benzyl alcohol
on a 3% nickel/aluminum-oxide catalyst in 51.7% theoretical yield. The
Card 1/3

86413
Catalytic Synthesis of Nitriles. CGmmunication 3. S/062'r.'J" 2 Ift 3YXX
V1 000, 00811b
Preparation of Aromatic Nitriles B013/B 055
reaction of P-phenyl ethanol with ammonla at 300 0C and of y-phenyl pro-
panol with ammonia at 330 0C over 7-Wo' nickel/aluminum-oxide catalysts also
lead to the formation of the corresponding phenyl acetonitrile (44-06
yield) and P-phenyl propionitrile (50.8% yield). The authors describe the
reaction conditions given above as optimal.. The following reaction mechan-
ism is assumed tc explain the formation cf small quantities of amines and
aromatic hydrocarbons as by-prodLjts _`n the cyanation of aromatic and ali-
phatic (Ref. 7) alcohols. The experiments showed that the amine formation
is independent of the amount of nitrile formed. The first step is there-
fore assumed to be the conversion of al-lohol to the primary amine. Forma-
tion of secondary and terriary amines can then proceed according to the
scheme: 2ArCH 2NH2 ? (ArCH 2)2 KH 4.- NH 3* Part of the ammonia is decomposed
to nitrogen and hydrogen on the catalyst surface: 2NH ;0 N + 3H,. The
3 2 C
hydrogen so formed, together wj.+,h the hydrQgen formed -in the main reac-
tion, reduces a certain am,.)unt cf the final nitrile to the aromatic hydro-
carbon. There are 4 tables and 24 references: 6 Soviet, 8 US, 6 German,
6 French, 3 British, and I Belgian.
ASSOCIATION: Institut organicheskoy khim-L'i im. rf. D. Zelinskogo Akademii
nauk SSSR (Institute of Organic Chemistry imeni N. D.
Card 2/3 Zelinskiy of the Academy -,~f Sciences USSR)

86413
Catalytic Synthesis of Nitriles. CGmmunication 3. S106 60/000/00*1/0 3YX X
Preparation of Aromatic Nitriles B013YB055
SUBMITTED: February 2, 1959
Card 3/3

86414
S/062/60/000/008/022/033/XX
BO13/BO55
AUTHORS: Timofeyeva, Ye. A., Dobrynina, T. P.,
Plotnikov, Yu. N., Petryayeva, G. S., and Gayvoronskaya,
G. K.
TITLE: Catalytic Dehydrogenation of Isohexanes
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1960, No. 8, pp. 1457-1465
TEXT: The present paper is a continuation of the investigation into the
dehydrogenation of hydrocarbons of different structures over an aluminum-
chromium-potassium catalyst. The catalyst is discussed in detail in Ref.l.
The 2-methyl pentane, 3-methyl pentane, and 2,3-dimethyl butane used in
this investigation were prepared by the Grignard reaction. 2,2-dimethyl
butane was obtained by pyrolysis of pinacoline alcohol acetate ~Ref. 2).
The experiments were carried out in a continuous systemg at 500 C and
atmospheric pressure and a flow rate of 0.5 h-1. The cataly8t was re-
generated after every experiment by oxidation in air at 700 C. The
properties of the isohexane catalyzates are listed in Table 1 and the
-.1 1/3

86414
Catalytic Dehydrogenation of Isohexanes S/062/60/000/008/022/033/Xx
BO13/BO55
composition of the gases formed in Table 2. For comparison, the correspond-
ing data for n-hexane are also given. As is shown, dehydrogenation of
2-methyl pentane, 3--methyl pentane and 2,3-dimethyl butane yields 34-40%
unsaturated hydrocarbons. Isohexanes form up to 2% and n-hexane up to
43% aromatic hydrocarbons. 2,2-dimethyl butane was found to form 15% un-
saturated hydrocarbons. Formation of aromatic hydrocarbons was not ob-
served. The gaseous products formed from 2--methyl pentanev 3-methyl pen-
tane and 2,3-dimethyl butane contained 84 - 90% hydrogen, 9 - 12% methane,
ethane, and propane, and I - 4% of other alkenes and alkanes. The gas ob-
tained from 2j2-dimethyl butane contained 72.6% hydrogen, 21.2% C -C
alkanes and 6.2% of Gther hydrocarbons. These data show that 2,2-hJthyl
butane is less stable under the given conditions than all cther isohexanes.
This conclusion was confirmed by the examination of the-liquid catalyzates.
Analytical data on the catalyzatecomposition allow the conclusion that, in
hydrogenation under the given conditions, all the isohexanes form alkenes
containing essentially 6 ~,,arbon atoms. Isomerization was not observed in
dehydrogenation of 3-methyl pentane. Slight isomerization occurred during
dehydrogenation of 2-methyl pentane and 2,3-dimethyl butane. 2,2-dimethyl
butane formed alkenes during the catalytic reaction. Approximately half
of these alkenes were !somerization products: 4-methyl 2-pentene,
Card 2/3

86414'
Catalytic Dehydrogenation of Isohexanes S106 60/000/008/022/033/XX
B01 3YBO55.
2-methyl 2-pentene and 2,3-dimethyl 1,3-butadtene. Finally, a thermo-
dynamic calculation of the reaction isohexanes - 0 isohexenes was carried
from the '
out (Table 8, Fig. 2). It Is evident results obtained that the
experimental yields of' isohexenes approach the equilibrium yields. Fig. 1
represents ohromatograms of an artifioial hydrocarbon mixture and several
fractions of isohexane catalyzates. The authors thank R. N. Shafran for
carr,ving out the analysis of the gases. There are 2 figures, 9 tables,
and 9 referenc,3s: 7 Soviet, I US, and 2 British.
ASSOCIATION: Institui organicheskoy khimii im. N. D..Zelinskogo Akademii
nauk SSSR
(Institute:, cf-Organic Chemistry i-meni N. D. Zelinskiy of the
A,~ademy cf S,;Iences USSR)
SUBMITTED: February 1'1, 1959
Card 3/3

S/062/60/000/008/023/033/XX
B013/BO55
AUTHORS: M--nachev, Kh~ M., Shuykin, N. I , and Markov, M. A,
TITLE: Investigation of the Effect of the Specific Surface of
Platinized Alumosilicate on the Degree of n-Nonane
Can,-**e:sion
PERIODICAL: izvest.iya Akad,~mii nauk SSSR. Otdeleniye khimicheskikh nauk,
1960, No. 8, pp. 1466-1470
TEXT: This paper is a continuation of the studies on the effect of the
specific surface of catalysts on the degree of hydrocarbon conversion.
For this purpose, the authors studied the conversion of n-nonane on alumo-
silicate catalys%3 with wlidely varying specific surfaces. Two 0.5% plati-
num/alumosilicate catalysts with specific surfaces of 320 m2/g (K_I)
and 60 m2lg (K-2) -nere used. A standard alumosilicate catalyst for the
cracking process was -.used as carrier for the preparation of the platinum
catalysts. To prepare the latter, the carrier was saturated with a dilute
H2PtCl6 solutlon. The data ~.-,f the n-nonane used were in agreement with
those given in Ref- 4. Infrared spectra showed the n-nonane to be free
Card 1/3

Investigation of the Effect of the Specific S/062/60/000/008/02'#/033/XX
Surface of Platinized Alumosilicate on the B013/B055
Degree of n,.Nonane Conversion
of isomers. The experimental apparatus has been described in Ref. 1.
The experiments were carried out in a continuous system at 360 to 450 C,
a hydrogen pressure of 10 atm and a flow rate of 1 h-A. The molar ratio of
hydrocarbon and hydrogen was 1:5. A fresh catalyst was used for each ex-
periment. The results of the examination of the catalyzates are listed in
Tables 1 and 2 and graphically represented in Figs. 1 - 3. These data show
that the degre-i of hydrooracking of hydrocarbons considerably decreases
with decreasing specific catalyst surface. This is in agreement with data
given in Ref. 2. The yields of hydrocracking products on X-1 catalysts
were found to increase mcre rapidly with a temperature rise than on K-2
catalysts. At temperatures of 420 0 - 4500C, hydrocracking on K-2 is in-
significant, which enables C9-isoalkanes to be obtained in comparatively
high yields (54% at 4W'C), On K-1, the maximum yield of isononanes is
obtained at03800C (53~). Since arcmatization occurs to a noticeable degree
only at 400 C, aromatla hydrocarbons can be obtained over K-2 before C
isoalkane yields are reduced. The total yield of hydrocracking product2
under the experimental conditions was 45.7% over K-1, and 25.3% over K-2.
The experiments ha-.,e thus shown that by decreasing the specific surface
Card 2/3

Investigation of the Effect of the Specific S/062/6o/ooo/oo8/O23/O33/XX
Surface of PlatinLzed Alumosilicate on the BO13/BO55
Degree of n-Nonane Conversion
of the catalyst the process can be carried out at higher temperatures
without the occurr,;nce cf hydrooracking. There are 3 figures, 2 tables,
and 4 Soviet references.
ASSOCIATION: Institut organichoskoy khimii im. N. D. Zelinskogo Akademii
nauk SSSR
(Institute- of Organic Chemistry imeni N. D. Zelinskiy of
the Acad-amy of Sciences USSR) V/
SUBMITTED: F-sbruary 76, 19'0
Card 3/3

S/062/60/000/008/026/033/XX
BO13/B055
I- and An, V. V.
AUTHORS: _ah~n, ~N.
TITLE: Dehydration of Tetrahydropyran on TiO 2 - Al2 03
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1960.4 No. 8, pp. 1508-1510
TEXT: In this brief publication, the authors describe a study of the
dehydration of tetrahydropyrans on TiO 2 - Al 203(8 mole%'Al203) and the
dependence of the yields in cyclopentadiene and pentadienes on the flow
rate and temperature. The experimental technique and preparation of the
catalyst were described in Ref. 3. The relation between tetrahydropyran
transformationto cyclopentadiene and piperylene and the flow rate at
6oo 0C was found to be the same as in the case of tetrahydrosylvan. The
maximum yields of cyclopentadiene and pigerylene, however, were lower,
i.e., 10.2 and 36.6% respectively at 600 C and a flow rate of 1 h-1. The
maximum cyclopentadiene yields are obtained at comparatively low tempera-
tures, around 4000C, a fact which deserves attention. Piperylene yields
increase with rising temperature and at high temperatures attain a practi-
cally constant value. Thermodyamiz- equilibrium calculations carried out
Card 1/2

Dehydration of Tetrahydropyran on TiO 2 -Al203 S/062/60/000/008/026/033/XX
B013/BO55
by Kilpatrick qnd collaborators (Ref. 2) showed that 1,4-pentadiene can
be transformed to piperglene in yields of 90 to 95% in the temperature
range investigated (350 - 6000C). The low 1,4-pentadiene content in the
catalyzate proves that its transformation to piperylene proceeds at a
remarkable rate. It was found that the isomerization of the primarily
formed 1,4-pentadiene is accompanied by a number of other reactions:
hydrogenation~ polymerization, cracking0and charring. As a result, the
catalyzate contains up to '8-5% (at 6oo C) 1-pentene and 2-pentene, and
traces of isoprene, isoamylenee,n-pentane and isopentane. There are
2 figures and 4 references: 3 Soviet and 1 US.
ASSOCIATION: Institut organicheskoy'khimii im. N. D. Zelinskogo Akademii
nauk SSSR
(Institute of Organic Chemistry imeni N. D. Zelinskiy of the
Academy of Sciences USSR)
SUBMITTED: January 7, 1960
Card 2/2

S/062/60/000/008/027/033/Xx
B013/BO55
AUTHORS: Viktorova, Ye. A., and Korosteleva, G. S.
TITLE: Catalytic Synthesis of 2,4-Di-tert-amyl Phenol
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1960, No. 8, p. 1510
TEXT: This is a brief communication on the catalytic synthesis of 2,4-di-
tert-amyl phenol. The latter was synthesized by alkylating phenol with
trimethyl ethylene in the presence of a KU-1 cationite, a sulfonated
phenol-formaldehyde resin. The yield of pure 2,4-di-tert-amyl phenol
was 30% of the theory. 2,4-di-tert--amyl phenol was then transformed to
the corresponding phenoxy acetic acid derivative. This was then precipi-
tated with hydrochloric acid and recrystallized from 20% alcohol. The
yield was 30 to 35%, Amy! phenols, including 2,4--di-tert-amyl pheno;
was used as antioxidants and as intermediatesfor the synthesis of in-
secticides and herbicides. There is 14 non-Soviet reference.
ASSOCIATION: Moskovskiy gosudarstvennyy universitet im. M. V. Lomonosova
(Moscow State University imeni M. V. Lomonosov)
LAR&A94a.,

S1062/601'000/009101 3/021
B023/BO64
AUTHORS: Shuykin,,N. I. and Vasilevskaya, G. K.
TITLE: Catalytic Dehydration of Alpha Isobutyl Tetrahydrofurane
PERIODICAL: Izvestiya Akademii nauk SSSR- Otdeloniye khimicheskikh
nauk, 1960, No. 9, pp. 1664-1667
TEXT: N. I. Shuykin, V. A. Tulupov, and I. F. Bellskiy referred in their
paper (Ref. 3) on the dehydration of tetrahydrosylvane on a titanium-
alumina catalyst at 500-6000C and a pressure of 20-30 mm to the fact that
this catalyst leads to the formation of both open and cyclic dienes. The
authors studied the dehydration of a more complex tetrahydrofurane homologi
viz.a(-isobutyl tetrahydrofurane. They carried out this reaction on the
same catalyst and expected to obtain 6-methyl pentadiene-1,3 in the
mixture with its dehydrocyclization products. At 600 and 5500, and a
pressure of 20-30 mm, and a volume rate of 0.1 h-l,cK-isobutyl tetrahydro-
furane underwent strong cracking, and, consequently, liquid catalyzates
were obtained in a yield of 25-30% only. It was a complex mixture of
rapidly resinifying hydrocarbons with a high boiling point. After the
u/
Card 1/2

Catalytic Dehydration of Alpha Isobutyl S1062V601000100910131021
Tetrahydrofurane B023/BO64
dehydration temperature had been reduced to 4000C and the contact time
shortened, a liquid catalyzate was obtained in a yield of 95P/c. In indivi-
dual fractions, with boiling points between 121-7-136cC, it contained
between 81.0 and 92% diene hydrocarbons,. Summing up: Considerable amounts
of unsaturated hydrocarbons, especially dienes, may be obtained oil the
basis of a pentosan-containing initial substance and furfurole, furane
homologs, and their tetrahydro derivatives. The finding of conditions for-
the catalytic dehydration of tetrahydrofurane homclogs under the formation
of complicated mixtures of dienes and alkeres is regarded as a further
task; in this connection it is possible to isolate individual hydro-
carbons. A formula of Ye. A. Timofeyeva, T. P. Dobrynina, and V. M.
Kleymenova is mentioned. A determination method developed by G.,P.Kaufwan
and G. D. Gallpern is applied. There are 1 table and 9 references:
6 Soviet, 4 French, 1 US, 2 British, and 1 German.
ASSOCIATION: Institut organicheskoy khimii im. N.D.Zelinskogo Akademii
nauk SSSR (Institute of Organic Chemistry imeni N. D.
Zelinskiy of the Academy of Sciences USSR)
SUBMITTED: March 18, 1959
Card 2/2

S/062/60/000/010/011/018
BO15/Bo64
AUTHORS: Minachev, Kh. M., Ryashentsevaq M. A., and Shuykin, N. I.
Catalytic Transformations of Cyclohexane'~Methyl Cyclo-
TITLE:
pentane, and n-Hexane on a Palladium Alumina Catalyst at
Increased Temperature and Increased Hydrogen Pressure A
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh
nauk, 1960, No. 10, pp. 1844 - 1847
TEXT: In previous papers.(Refs. 1-4), the authors investigated the
catalytic properties of 0.5% palladium alumina catalysts in the re-form-
ing of small gasolineUractions of petroleum from the Illskiy,
Khadyzhenskiy, Ural, and Volga deposits. To confirm the results obtainedy
the authors studied the transformation of cyclohexane, methyl cycl
pentane, and n-hexane on 0-5% palladium-containing alumina catalysts
under the optimum conditions of re-forming gasoline fractions (48OPC,2()atm,
H :HC 5, v = 1.0 hours -1 . The experiments were
2 rcarried out in a
continuous-flow apparatus. The catalyzate obtained from cyclohexane
-Card I

Catalytic Transformations of Cyclohexane, S10621601000101010111018
Methyl Cyclopentane, and n-Hexane on a B015/Bo64
Palladium Alumina Catalyst at Increased
Temperature and Increased Hydrogen Pressure
contained 5Wo benzene, while C 6 paraffin hydrocarbons with approximately
6% and five-membered cyclanes with approximately 43% were detected in
the naphthene paraffin component (Table 1, composition), i.e., a de-
hydrogenation to benzene, an isomerization with a contraction of the
cycle, and a slight hydrogenolysis under the formation of alkanes took
place. Approximately 9 5% aromatic hydrocarbons and, besides unchanged
n-hexane, approximatel; 5% paraffin hydrocarbons with iso-structure
were obtained from the transformation of n-hexane. Besides unchanged
methyl cyclopentane, methyl cyclopentane (Table 2) yielded approximately
11% 2,3-dimethyl butane, 3-methyl pentane, n-hexane, n-pentane (approxi-
mately 3.8%), and approximately 1.2% cyclohexane of the paraffin com-
ponents, and 33% benzene as the aromatic component of the catalyzate.
Thus, methyl cyclopentane undergoes an isomerization to cyclohexane and
subsequent dehydrogenation to benzene, as well as hydrogenolysis and
hydrocracking under the formation of n-pentane. A Scheme is given on
the basis of the results obtained, and it is stated that the present
Card 2

Catalytic Transformations of Cyclohexane, 3/062/60/000/010/011/018
Methyl Cyclopentane, and n-Hexane on a B015/BO64
Palladium Alumina Catalyst at Increased
Temperature and Increased Hydrogen Pressure
experiments confirm the formation mechanism of aromatic hydrocarbons in
re-forming the above gasoline fractions. There are 2 tables and
6 Soviet references.
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo
Akademii nauk SSSR (Institute of Organic Chemistry
imeni N. D. Zelinskiy of the Academy of Sciences USSR)
SUBMITTED: May 14, 1959
Card 313

3106,16010001010/031 /031
73 0 0 2 ///,It 0 6 0
....... S-uykin, N. I. , Tyan' Sin-khua
Some Problems Concerning the 1114echanism of Conversion of
:.:ethyl Cyclohexane on a Nickel - Alumina Catalyst at
Tncreased Hydrogen Pressure
OD I C1, L Izvestiya Akademii nauk SSSR. Otudeleniye khimicheslkikh nauk,
11,160, 11o. 10, pp. 1891-1894
'_EXT: The authors studied the reaction 0oficyclohexane, me-thyl cyclohexane,
methyl cyclopentane, and toluene at 360 C qnd 20 atn hydrogen pressure on
a 10;,, Ni-Al203catalyst, volume velocity 0.2 h7l, and -molar ratio hydrogen:
_'ydrocarbon = 4:1. 3enzene, me'uhvl cyclopentane, n-Dentane, n-hexane,
-nd 2--_-ethyl pentane are chiefly
.io-_ . Cyclohexane may dlecom~)ose
0
2 3,
C_C_C_C_C_C
2
formed
by t-.-,o
or
from cyclohexane under theze condi-
mechanisma
6 C :1 2/! 6 C7,4
lard 1/3
1

Some Problems Concernina the Yechanism of 31061V601000/010; 3 1
,onver--ion of ',:e'.hyl C-yclohexane on a
Nickel - Alumina Catalyst at Increased Hydrogen
7re 9 o,2,re
toluene, and benzene are chiefly formed from methyl cyclo-
hexane. 11.4oreover, also 3-methyl hexane, 2-methyl hexane, and others, are
.r
~ormcd. The following scheie is suggested for these reactions:
C-C-C-C-c
C I ~
C C C
C if.
C-~-C-~-c
C-C-C-C-G-c
C
/ H2 C-C-C-
C C-C
I H2 -CH4
C-rrc-C-C-C C C
~;' ., .-31 C-r_-C-C -C
C-C-C-C-C-c 3H? 6c", 7
I
C C
+ CH.
Card 213

Scme Problems Concerning the Mechanism of S/062/60/000/010 /031/031
version of Methyl Cyclohexane on a B002/Bo6o
.'i. 'el - Alumina Catalyst at Increased
Hy:lrogen Pressure
The reaction of methyl cyclopentane mainly yielded 2-methyl pentane,
3-methyl pentane, and benzene. The toluene reaction yielded methyl
cyclohexane, cyclohexane, benzene, and others. There are 2 tables and
7 Soviet references.
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo Akademii
nauk SSSR
(Institute of Organic Chemistry imeni N. D. Zelinskiy of
the Academy of Sciences USSR)
SUBMITTED: March 25, 1960
Card 3/3

S/062/60/000/01 1 /,008/0106
B01 3/BO78
AUTHORS: Shuykin, N. I., Tyan' Sin-Khua
TITLE: Demethylization of Methyl Cyclohexane in Contact With
Nickel Catalysts Under Hydrogen Pressure
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1960, No. 11 , pp - 2014 - 2018
TEXT: In this paper the catalytic demethylization of methyl cyclohexane
on nickel catalysts was investigated in a continuous system under hydro-
gen pressure of 20 at and at temperatures of 3300-3600C. Industrially
produced silica gels served as carriers with a granulation of 1.5-2 mm,
aluminum oxide of the type A-2 (A-2) and alumosilicate from GrozNII
(Groznyy Petroleum Scientific Research Institute) which were pre-treated
by the dynamic method (Refs. 9 and 10). Nickel aluminum oxide, nickel
silica gel, and nickel-aluminum silicate catalysts were obtained by im-
pregnation of the respective carriers with a nickel nitrate solution, by
calculating 101/4 nickel per catalyst. A second specimen of the 1CF%6 nickel
silica gel catalyst was obtained by simultaneous precipitation of
Card 1/2

Demethylization of Methyl Cyclohexane in Contact S/062/60/000/011/008/016
With Ifickel Catalysts Under Hydrogen Pressure BO13/B078
appropriate nitrate solutions, and a third specimen by pre-treatment of
the carrier with hydrofluoric acid. Results obtained by catalysis of
methyl cyclohexane are shown in Tables 1-5- It was found that the cata-
lyst treated with hydrofluoric acid is beat suited for the demethyliza-
tion of methyl cyclohexane. The yield of cyclohexane in the presence of
this catalyst amounted, after one passage, to 30.1% of the converted
methyl cyclohexane. Moreovdr, this catalyst shows a larger selectivity
than the non-treated one. The demethylization of methyl cyclohexane with
nickel catalysts is complicated by the fact that part of the resulting
cyclohexane is isomerized to methyl cyclopentane, and next, the hydro-
genolysis of the latter takes place under formation of alkanes.
Ye. I. Sillchenko is mentioned. There are 5 tables and 11 references:
9 Soviet.
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo
Akademii nauk SSSR (Institute of Organic Chemistry imeni
N. D. Zelinskiy of the Academy of Sciences USSR)
SUBMITTED: Jun.- 20, 1959
Card 2/2

S/062/60/000/011/011/ol6
B013/BO78
AUTHORS: Shuykin, N. I., Tyan' Sin-Khua
TITLE: Hydrogenolysis of C 7 Alkanes in the Presence of a Nickel
Aluminum Oxide Catalyst Under Hydrogen Pressure
PERIODICAL: Izvestiya kkademii nauk SSSR. Otdeleniye khimicheskikh
nauk, 1960, No. 11, pp. 2046 - 2048
TEXT: This is a brief report on the hydrogenolysis of n-heptane,
3-methyl hexane, 2,4-dimethyl pentane, and 2,2-dimethyl pentane with a
Ni-Al 0 catalyst in the continuous-flow system at 3600C and at a
2 3
hydrogen pressure of 20 atm. The molar ratio of hydrogen to hydrocarbon
was 4:1. The volume velocity amounted to 0.2 h- 1. The composition of the
liquid catalyzate was determined by chromatography. The waste gases were
examined with a chromatographic gas analyzer. Results are tabulated. The
table shows that, under the present conditions, the alkanes considered
undergo hydrogenolysis, but isomerization does not take place.
Card 1/4

Hydrogenolysis of C7 Alkanes in the Presence S/062/60/000/011/oli/ol6
of a Nickel Aluminum Oxide Catalyst Under BO13/BO78
Hydrogen Pressure
Methylcyclohexane and cyclohexane are partially isomerized under the
same conditions. Here, the rings are compressed into pentamethylene
hydrocarbons. The composition of the gases thus obtained and of the
liquid catalyzates indicates that the hydrogenolysis of the alkanes
proceeds according to the mechanism of a systematic demethylation. The
authors propose the following systems for the catalytic hydrogenolysis
of C7 alkanes with varying structure:
Card 2/0

Hydrogenolysi:j of C7 Alkanes in- the Presence ~SI062V601000101#10111016
of a Nickel Alumin .um Oxide Catalyst Under B013/3078
Hydrogen Prezsure
It was found thatpunder 'the present' conditions',-the tertiar .y carbod atom
in the 3-methylhexanc atom not only inhibits thd '~ydrogenolysis of the
group directly bound to it, but also the relatively easy hydrogenolysis
of the neighboring C-C bonds. The hydrogenolysis of the groups being
most distant from the tertiary carbon atom proceeds with great rapidity.
This hydrogenolysis is even-more.,.distinct in the case of 2,2-dimethyl-
pentane which contains a quatern'ry carbon atom. D. bl. Tilicheyev and
A. A. Polyakova are m6ntioned.~There are 1 table and 9 references:
5 Soviet, 3 US, and 1 German..
ASSOCIATION: Institut organicheskoy-khimii im. N.'D. Zelinskogo
Almdemii nauk SSSR,(instituteof Organic Chemistry
imeni N. D. Zelinskiy of the Academy of Sciences USSR).
SUBITITTEDd April 18, ig6o
Card 4/0

VIXTORO-VA, Ye.A.; SHUYKIN, N.I.; FOLYANSKAYA, E.I.
I Cycloalkenylation of phenol by 1,3-CYclohexadiene. Izv. AU SSSR.
Otd. khim. nauk no.11:2048-2049 H 160. (14IRA 13:11)
1. Moskovakiy goeudarstvannyy univerattet im.N.Y.Losonosova.
(Cyclohexadiene) (Phenols) (Alkanylation)

S/062/60/000/012/010/020
BO13/BO55
AUTHORS: --Shuykin,_ff, -I.,, Timofeyeva, Ye, A,, Plotnikov, Yu, N., and
Andreyev, N. 3,
TITLE: Composition of the Products of Dehydration of C - C
n-Alkanes Over Aluminum-chromium-potassium Cata~yst 9
PERIODICAL: Izvestiya Akademii nauk SSSR. Otdeleniye khimicheskikh nauk,
1960, No. 12, pp. 2173-2177
TEXT: In the present paper the authoisstudied the structure of unsaturated
and aromatic hydrocarbons, but above all the composition of alkenes
formed from n-alkanes at 5000C over an aluminum-chromium-potassium catalyst
and a volume velocity of 0.5 h-1. n-hexane, n-heptane, n-octane and n-nonane
were used for this reaction. The unsaturated hydrocarbons formed were found
to consist mainly of alkenes. As regards number of carbon atoms, they cor-
respond to the initial alkanes and have double bonds in the positions 2, 3
or 4. The catalyzate of n-hexane was found to contain 1-hexene also, but
in much smaller amounts than 2- and 3-hexenes. The catalyzates of n-heptane,
n-octane, and n-nonane possibly contain other alkenes in addition to the
2-heptene, 4-octene, and 4-nonene actually found. The quantities contained,
howeverp are so small that they were not detectable in the Raman spectra.
Card 1/2

Composition of the Products of Dehydration S1062V601000101210101020
of C6 - C9 n-Alkanes Over Aluminum-chromium- BO13/BO55
potassium Catalyst
All catalyzates were found to contain dienes, the structures of which could
not yet be established exactly. The structure of the aromatic hydrocarbons
formed from n-alkanes becomes more complicated as the molecular weight
of the initial alkane increases. n-hexane forms benzene, n-heptane toluene,
n-octane mainly xylenes and ethyl benzene as well as lower-boiling aromatic
hydrocarbons, benzene and toluene. The aromatic hydrocarbons formed from
n-nonane consist mainly of methyl ethyl benzene, trimethyl benzene, and n-
propyl- and isopropyl benzenes. Apart from these, the catalyzate contains
lower-boiling hydrocarbons, benzene, toluene, and ethyl benzene. There
are 5 tables and 5 references: 3 Soviet and 2 British.
ASSOCIATION: Institut organicheskoy khimii im. N. D. Zelinskogo Akademii
nauk SSSR
(Institute of Organic Chemistry imeni N. D. Zelinskiy of the
Academy of Sciences USSR)
SUBMITTED: July 10, 1959
Card 2/2

. In 0
VI.L'C-.u'A, Ye.,',,.; 6AY,~I'L:9 G.v.
Contact cata-ljtic ccnv-.rsions of Pa---t 5: Alkylation of
'v-creso" ',.y yiperylene. Vest. un. -Se---. 2: 11'adl. . 1,; nc.~S:
62-65 N-3 160. (:~:r.'I 1-/:-g)
1. Kafodra khirdi nefti Moskovs:-orpo u-nivers-,",eta.
(GrC301)

B&AURI, IT.G.; SHMIIT, N.I.; SHAKA-IIASHVILI, T.S.
Catalytic transformatiom of N tridecane, N tetradecane and N pentade-
cane under hydrogen pressure in a flow system. Soob.AH Gruz. JPIk
no.6:655-662 Je 160. (MIRA 13:9)
1. AN GruzSSR, Institut khimii im. F.G. Melikashvili. Tbilisi i AN
SSSR, Institut organicheskoy khImii im.N.D. Zelinskogo. Moskva
F~redBtavleno chlenom-korrespondentom Akademii G.V. TSitsishvili.
2. Chlen-korrespondent AN SSSR (for Shuykin).
(%cane)

BXKAURI, N.G.; SMITKIN, N.I.; SHKARASHVILI, T.S.
Improving the motor characteristics of a normal undecane and
dodecane. Soob.AN Gruz.SSR 25 no-5:525-531 H 160.. OURA 14:1)
1. Akademiya nauk GruzSSR, Institut khimii imeni P.G.Kelftishvill,
Tbilisi i AN SSSR, Institut organicheskoy khimli imeni N.Zelinskago,
Moskva. Predstavleno chlonom-korrenpondentom Akademii G.V.TSitsi-
shvili.
(DDdecans) (Undecane)

SIRJYKIN, N. I.; BRIVANSKATA, L.A.
N
Catalytic hydrogenation of phenols. Uep.khim. 29
no.5:648-668\lgy 160. (XIBA 13:7)
1. Khimicheskiy fakulltat Koskovskogo gosudaretyennogo
universiteta im. N.Y.Lononosova.
(Phenols) (EVdrogenation)

S/074/60/029/05/03/005
B008/BO06
AUTHORSt Shuykin, N. I., Erivanskaya, L. A.
TlTLEt Catalytic-iL*drbrgenationjof Phenols
PERIODICALj Uspekhi khimii, 1960, Vol.29, No- 5, pp. 648-668
TEXTs An investigation of catalytic transformations occurring in the
hydrogenation of phenols separated from higher fractions of primary
resins, and in the hydrogenation of narrow fractions enriched in one or
the other component was carried out. Sharp rectification- or chromato-
graphic methods can be applied for separating these fractions. Previous
research in the field of phenol transformation in hydrogenation is des-
ciibed in Refs. 1-8. Hydrogenation of phenols to hydroaromatic alcohols
is discussed in Refs. 1, 9-91. Hydrogenations on platinum-, palladium- P
copper-, and nickel catalysts are described. Hydrogenation of pure ghen-
ols can be carried out at comparatively low temperatures (up to 200 C)
as well as at high- or atmospheric pressures in the presence of nickel-
or platinum catalysts. Hydrogenation of industrial phenol mixtures is
more difficult, owing to catalyst poisoning by sulfur-containing com-
pounds. The reaction order of phenol hydrogenation is probably between
zero and one. Which of the possible geometric isomers of the correspond-
,-Card -1/4

Catalytic Hydrogenation of Phenols S/074/60/029/05/03/005
B006/BO06
ing alcohol is formed, depends on hydrogenation conditions. Published
data on the properties of cis- and trans-methyl cyclohexanols and
melting points of their derivatives are given in Table 1. Hydrogenation
of phenols to hydroaromatic ketones is described in Refs. 29, 66t 78,
92-101. In general, alicyclic ketones can be prepared by hydrogenating
the corresponding phenols. Yields of these ketones. however, depend not
only on hydrogenation conditions, the nature of the catalyst, and the
amount of hydrogen adsorbed, but also on the structure of the initial
phenol. The reduction of phenols to aromatic hydrocarbons is discussed
in Refs, 5, 102-154. Catalysts based on molybdenum are generally applied.
Experimental- and thermodynamic data indicate that a pressure drop
during the hydrogenation of phenols in the presence of molybdenum
catalysts increases the yields of aromatic hydrocarbons.1 The reaction,
however, is slower and accompanied by considerable charring. At higher
temperatures, phenols tend to give various condensation reactions. The
formation of alicyclic hydrocarbons in the hydrogenation of phenols to
the corresponding alcohols was observed by many investigators (Refs. 27,
28, 31, 66, 113, 118, 137, 140, 141, 149, 155-160). These hydroaromatic
hydrocarbons, however, were only formed in small quantities as by-prod-
ucts of hydroaromatic alcohols. In order to obtain alicyclic hydrocarbons-:
Card 2/4

Catalytic Hydrogenation of Phenols B/074/60/029/05/03/005
B008/BO06
as main reaction product, the hydrogenation temperature must be chosen
high enough to ensure dehydration of the alcohols. The behavior of
polynuclear phenols in hydrogenation reactions has not been investigat-
ed widely (Refs. 107, 128, 136, 141, 158, 161-168). High-pressure hydro-
genation of these compounds in the presence of molybdenum catalysts
yields hydrocarbon mixtures containing aromatic-, hydroaromatic-, and
various other hydrocarbons. Phenol formation is also observed. Refs. 6,
169-213 deal with the destructive hydrogenation of higher phenols, by
which lower phenols are obtained. Thermodynamically, dealkylation of
phenols is also possible. It can be effected by cracking higher phenols,
or, by reacting higher phenols, without a catalyst at higher temperatures.
Yields of lower phenols, however, are small. Several patents (Refs.
199-204) recommend destructive transformations of phenols to be carried
out not only in the presence of metal oxides and metal sulfides, but
also in contact with cracking catalysts. The direction of the reaction
can be determined by eboceing appropriate conditions and catalyst admix-
tures. The following persons are mentioned: V. V. Tishchenko, M. A.
Belopol~skiy, B. L., Moldavskiy, I. B. Rapoport, S. Ye. Lifshits, A. V.
Lozovoy, M. K. D'yakova, V. N. Ipatlyev, N. A, Orlov, M. F. Shosta-
kovskiy, V. V. Shabarov, Ye. A, Viktorova, I. Ye. Pokrovskayaq A. I.
Card 3/4

Catalytic Hydrogenation of Phenols S/074/60/029/05/03/005
B008/BO06
Afanaslyeva, V. F. Polozov, Ye. 1. Sillchenko, A. Bagg T. Yegunov,
D. Volokitin, S. A. Deryabing'A. M. Yasnyy, A. P. Terentlyev, A. N.
Guseva. I. N. Nazarov, Ye. N. Zillberman, P. Fisher, N. Prokopchuk,
Ye. I. Prokopets, I. I. Yeru, B. K. Klimov, I. F. Bogdanov, V. I.
Boby8hev, M. P. Minchenkov, V. P. Konov, K. A. Alekseyeva, T. Gritfie-
vich, V. Ilonanov, G. Z. Koshell, V. A. Lanin, M. V. Pronina, M. S.
Knyazeva, V. I. Zabavin, M. 1. Kuznetsov, K. A. Belov, N. P. Masina,
I. V. Kalechits, F. G. Salimgareyeva, N. N. Vorozhtsov junior , and
V. N. Lisitsyn. There are 1 table and 213 references, 58 of which aze
Soviet.
ASSOCIATIONR Khimicheskiy fakulltet MGU
(Chemical Department of the
imeni M. V. Lomonosov)
im. M. V. Lomonosova
MSU (Moscow State University)
Card 4/4

S/074/60/029/010/002/004
B013/BO75
AUTHORS: Shuykin, N. 1. and Viktorova, Ye. A.
TITLE: Catalytic Synthesis of Alkyl Phenols
PERIODICAL: Uspekhi khimliq 1960, Vol. 29,, No. 10, pp. 1229-1259
TEXT: The authors give a survey of studies made on the catalytic synthesis
of alkyl phenols. The available publications were systematized according
to the character of the alkylating substances. Papers are mentioned re-
ferring to some catalysts, on the character of which the structure and the
ratio of alkylation products are dependent. The subject of the first
chapter is the alkylation of phenols with unsaturated hydrocarbons. The
application of the following ~~atajy!jtsjis described: Acids as alkylation
catalysts (Refs. 32-108); metal chlorides in alkylating phenols with
alkenes (Refs. 63, 109-128); borofluoride (Refs. 129-168). Data obtained
show that sulfuric acid is the most frequently used catalyst. It is pre-
ferred due to its accessibility and its sufficiently high yields of alkyl
phenols. Also alkylation in the presence of resin - ion exchangers seems
to be promising. The use of borofluoride and of some of its molecular com-
_~,rd 1/3

Catalytic Synthesis of Alkyl Phenols S/074/60/029/010/002/004
B013/BO79
pounds requires further study, The use of aluminum phenoxide seems to
open new posnibilities in the synthesis of o-alkyl phenols. The second
chapter deals with the alkylation or phenois with alcohols (Refs. 36,
65, 80, 81., 99~~ 173 277). As was proved by the mentioned data, the strue-
ture and the yield of alkyl phenols are dependent on the reaction conditJons.
These, in turn, depend on the structure of the alcohols employed, on the
temperature, as well as on the nature of the catalyst. In some cases.
phase stateand pressure factor play an essential part. In spite of the
high yields, alkylation of phenols with alcohols is rather inexpedient
for industrial purposes; in laboratory practice, however, it offers a
number of advantages. In the third chapter,alkylation of phenols with al-
kyl halogens is discussed (Refs. 109 278-335),. Data available an alkyla-
tic~n with alkyl halogensishow that the reaction in the presence of aluminum
chloride is- E6'-st -M-roughly investigated. However, it has to be taken into
consideration that the isomerization of the radical entering into the
phenol molecule does not always take place. Alkylation with ternary alkyl
halogens in the presence of halogen hydracid is extremely easy, especial..
1y if the alkyl halogen forms during the synthesis. By this means, the
possibility of using more easily accessible alkenes is given.
Card 2/3

Catalytic Synthesis of Alkyl Phenols S/074/60/029/010/002/004
B013/B075
Yu. G. Mamedaliyev, V. N, lpatlyev,, V., I~ Isagulyants, A. V. Topchiyev,
1,Tsukervanik, V. Tambovtseva, B. M. Dubinin, A. Ye. Chichibabin., A. S.
Abdurasuleva, N. G. Sidorova, Z. N. Nazarova, I. N~ Samsonova, Z. P.
Aleksandrova, A. B. Xuchkarev, and P. P. Bagryantseva are mentioned.
There are 335 references: 40 Soviet, 188 US, 1 Austrian, I Belgian,
29 British, I Canadian, 1 Czechoslovakian, 1 Danish, 1 Dutch, 20 French,
38 German, 3'Itali~an, 1 Rumanian, 6 Japaneseand i Swiis.
ASSOCIATION: Khimichsskiy fakul7tet MGU im. M. V. Lomonoscva
(Department of Chemistry of the Mos'ccw State University
imeni M. V. Lomonosov
Card 3/3

5.3300,5.1190 77864
SOV/79-30-2-15/78
AUTHORSt Shuykin, N. I., Kashkovskaya, L. K., Kononov, N. F.
TITLEz Catalytic Hydrodealkylation of Polyalkylbenzenes. II.
Demethylation of Toluene over 10% Nickel-Alumina
Catalyst. Effect of Temperature and of the Rate of
Feed of TolUene
PERIODICAL: ZhUrnal obshchey khimii, 1960, Vol 30, Nr 2, pp 1124-
430 (USSR)
ABSTRAM The aUthOrS aLudied the effect of temperature and feed
rate Of toluene upon the degree of hydrogenolysis of
toluene over 10% nickel-alumina, in the temperature
range 1130-5100. It was found earlier (Zhur. Obshchey
Khim., 29, 2230, (1959) that the following reactions
can take place 0under conditions of hydrogenolysis
(Ni-Al2 03-P 46o , 5 atm):
Card 1/1~

Catalytic Hydi-odealkylation of Polyalkyl-
benzenes. II. Demethylation of Toluene
over 10,9 Nickel-Alumina Catalyst. Effect
of Temperature arid of the Rate of Feed of
Toluene
7r,
7,7864
SOV/79-30-2-15/78
The experimental results show that in the temperature
range 430-4600, reactions (2), (3), and (4) do not
take place to any appreciable extent. (Hydrogenation
was performed in apparatus which was described earlier
(loc. cit. ); the products of catalysis were fraction._,.Lf.-~d
arid identified by their Raman sVectra (optical analysis
was performed by Yu. P. Yegorov); in all experiments
the hydrogenitoluene ratio equaled 5) Increase of
pressure speeds up reactions (3) and ~4)(from 0.6 to
Card 214 35% for toluene-methyl6yclohexane conversion and from 1

"Y!,
j,
T -

v r lu~rv N i r- I-e
Y S_
lre flip t_, t
To I u, e P. e
Pr,l,
an
r a s -
noreases destruction
it ~h(
('~f rine aromat Lc ring: reacti-) '21 ll~ wus found
that -a change C mporature C v o, m. li AC) 10'~ di)C-s
LYS I S
no~ esseti~.Ja y a f't c-c ~ ~he yiela cf trie Latal
producr,zi n,~,,r the cont~en- -I~f benzene (30-35%).
Trie "life" of the catalyst. ulmder conji-I.--ions of steadilly
rising llemperWl-ure_ is cver 120 hours, vi Ihich is longer
a-_ cumsr,ant ~erfkperature (at-- 146o it was f~-"Jnd 7--o

leals ro
,a,
u f' t
,~A -,ue n. e C rom hr, a consider--
,
-
,
n benzene content
e c r e a s e
f rom 3:) -- 35 t-c -1 - ,
pr(Dd~ic-,,~ of" ca?,-al,,7s is ~bur Dn -rf-- c~tfler i-ialna
'2~
is inhibited b higher flow
rea c t i o n l
Lu: n
y
.
,
k
-
There al-e 3' -.ables; arid 8 references,
mf
,
_
S If e I U- . 3 The U.S. reference is- Selec~ed
Card Va'
F' Pn
!Jes (-
sical and Tnerrricdynamic Properties of
,
,
y

J
A S
IS T---' B IMI I IT E D
4v "I rn r j ~3 s u ull-gh
i ~a i r: 1 & rn 1 13 r r,r h e A c a d my o
ri- r-t-y., t i Al(,ij em m i 1

BOO',/BO55
AUTHORS: Sh--tykin, N, L., BeVskiy, I, Y-1 and Karakhanov. R. A.,
TITLE.- Hydrogenolysis of Tetrahydrofurans
PERIODICAL: Zhurnal obshchey khimii., 1960, Vol. 30, No. 6,
pp,, '933 - *937
TEXT: Since al! the investigations of Refs~ If - 4 on the reaction
me~..hanism of the catalytic hydrogenationlof the furan ring were mainly
ut- to establish only this mechanism, it sufficed to determine
,ha.:, ~~.he furan- and the tetrahyd---e-ofuran ring behaved differently in
hydr-.genolysis, w--~hout investigating possible transformations of
~etrahydrofurans during hydrogenolysis in greater detail, In an
.n'iestigatio-n -f the hydrogenolysis of tetrahydrofurans, however,
e-,-erything Indlicat4ing the difference between the furan and the tetra-
hydrofuran rings and their behavior in hydrogenolysis is of importance.
For this reason the authors of the present work investigated the
hydrc,genolysis of tetrahydrofurans,, They studied the hydrogenolysis of
S/079/60/030/006/033/033/XX
Card '/3

Hyd:-rgenf-,'Lys--, zi of Tetrahydrofurans S/079/60/030/006/033/033/XX
BOOI/B0505
2-alky'-,-, 2 2.,d'Lalkyl-. and 2,5-dialkyl-tetrahydrofurans in the vapor
f-Pase a,!. atmospher;i: pressure, using platinized carbon and a nickel -
qlum~-num skele!~on ~,atalyst, The hydrogenolysis of tetrahydrofuran
~- m,-, ~gs z-'-qu--:es higher temperatures and takes an entirely different
c~,-zrse than the hydrogenolysis of furan compounds., Hydrogenolysis of
tetrahydrofurans on platinized carbon at 3500C, besides causing
.S-~me:--zation to aliphati,,, carbonyl compounds, occurs simultaneously
a~ bctb C-0 bonds,, This leads to paraffin hydrocarbons with the same
ntim-'-e- cf carbon at-cms as the Initial tetrahydrofurans. On the nickel
a1um'-nim ske'e`on catalyst, hydrogenolysis of 2-alkyl- and 2,2-dialkyl
t,z,trahyd-.ofurans cccurs at the C-0 bond adjacent to the alkyl groups.
Primary alcohols and aldehydes forming as intermediates react to give
pa-affLn hyd:rocarbons, the carbon chains of which contain one carbon
at,~,m 1--ss than the Initial tetrahydrofuran derivative. The nickel -
aluminum skeleton catalyst also causes a more radical decomposition of
tetrahydrofurans. thus forming water and gaseous products. The
hyiz~,ganoiysis of furans has definite advantages over that of tetra-
hydrafurans, sincp ir, the first case aliphatic alcohols and ketones
Ca--d 2/3

Oxila--ion cf P.-Ketoacetals by
Means of Lead Tetraacetate
S/079/60/030/006/032/033/XX
B001/B055
A rea:-,ion mechanism is suggested involving intermediate formation of
a a1kc;xy r~nyl ketone and subsequent acetoxylation with lead tetraacetate.
A methcd was developed for the synthesis of a-hydroxy-p-ketoacetals by
trea-.,.'ng a acetoxy-P-ketoacylal compounds with a methandlic solution of
hydrogen ch"oride (Scheme 5) (yield 35 - 65%). It was shown that
a-a-~,:-toxy--P-ketcacylals react with polyhydric phenols or P-naphth6l
formLng 3-acetoxy substituted benzo- or naphtho-pyrylium salts. The
data given show that a-pleetoxy-p-ketoacylals are now accessible and
may prove important for'the synthesis of several hitherto inaccessible
~neter,)cyc',ic --cmpcunds..There are 14 references: 7 Soviet, 4 US,
3 German I
ASSOCIATION: Mcskovskiy gosudarstvennyy universitet
(Moscow State University)
SUBM'ITTED. June 11,, 1959
r,
~' a r d 1j/ 3

SHUYXIN, N.I.- BELISKIY, I.F.; SHOSTAKOVSKIY, V.M.
Catalytic isomerization of V-oxides. Conversion of alkyl
tetrahydrofaryl carbinols into aliphatic ketones. Zhur.ob.khim.
30 no-8:2757-2759 Ag 160. (MIRA 13:8)
1. Institut organicheskoy khimii Akademii nauk SSSR.
(Ketones) (Methanol)

84869
S/079
% 60/030/010/005/030
BOO O75

AUTHORS: Haryshkina, T. and Shuykin, N. 1.
-
TITLE: Synthesis of New gs of Cyclopentadiene
Homolo
PERIODICAL: Zhurnal obshchey khimii, 1960, Vol. 30, No. 10,
pp. 3205-3207
TEXT: Due to its difficult production, the chemistry of highly active
cyclopentadiene homologs - unlike the cyclopentadiene itself - has
hitherto not been thoroughly investigated. The synthesis of cyclopenta-
diene homologs described in Refs. I and 2 is reliable but somewhat compli
cated. The synthesis mentioned in Ref. 3 has to be improved in order to
reach a higher purity and yield of the final products, cyclopentadiene
and methyl cyclopentadiene. As cyclopentadiene yields organometallic
derivatives (e.g., cyclopentadiene potassium), alkyl or aryl radicals
can be introduced into its ring. However, this method only leads to
cyclopentadiene hydrocarbons having substituents in the C"2 group. Thus,
homologs of cyclopentadiene having Cl-C 4 substituents (Refs- 5, 6) in
position 5 were synthesized, as well as gem-substituted cyclopentadienes
Card 1/2

S/080/60/0)3/008/0' 12/01A 3
A0031AOOI
AUTHORS: Sh-aykin, N.I.1 Pozdnyak, N.A.
TITLE: The Catalytic Methylation of Benzene by Methanoll
FERIODICAL: Zhurnal prl-kladnoy khimil, 1960, Vol. 33, No. 8, pp. 1904-1906
TEXT: The article Is a continuation of the work published in Ref. 3. A
special apparatus was designed for the continuous methylation of benzene by
methanol and also for the methylation under a pressure of 20-60 atm. This
apparatus makes It possible to obtain catalyzates containing 92-95% alkylate
with at least 60% toluene. The apparatus comprises an electric furnace with the
alumosilicate catalyst, in which the reaction takes place at 450 and 5000C. The
ratio of benze-ne:methanol is 4:1. The alkylate obtained at 5000C consists of
60.5% toluene, 20.3% xyIenes and 19.2% polymetnylbenzenes. The methylation under
pressure.was investigated at 400, 45o and 4750C and pressures from 20 to 60 alum.
An Increase in pressure as well as in temperature promotes the formation of methyl-
benzenes, among them also xylenee. The yield of the toluene fraction increases
very slowly in tLhe pressure range from 20 to 40 atm and decreases with a further
pressure Increase. The effect of an excess of methyl alcohol in the reaction mix-
Card 1/2

9/076/60/034/04/31/042
BOIO/ '.009
AUTHORS: Yegorov, Yu. P. Romadan, I. A., Shlyapoohnikor, V. 1.9
Shudin, N. I. Noscow)
TITLE: Investigation of the Structure of the Radical@ of Substances
Obtained by Alkylation of Aromatic Hydrocarbons by Means of
Alcohols in the Presence of Boron Trifluorido '
PERIODICAL: Zhurnal fizicheskoy khimii, 1960, Vol. 34* No- 49 PP- 888 - 893
TEXT: In a number of earlier papers (Refs. 1-6) 1. A. Romadan described a method
for the alkylation of aromatic hydrocarbons with molecular alcohol compounds of
boron trifluoride at 165-1700 in an autoclave, or at a pressure of I atmosphere.
The results obtained do not agree with those given by other authors, and it in
assumed that a different reaction mechanism prevails under such conditions (with-
out activator and at 165-1700). For instance, in the alkylation of naphthalene
with n-butyl, n-amyl, and n-propyl alcohol alky naphthalenes with normal radicals
were obtained. The structure of n-butylnaphthal no was confirmed spectroscopically
(Ref. 13) and by a special method of dout riiaim exc &Me at the fiziko-khimicheskiy
.Lnotitut im. L. Ta. Karpova (Physicochemical Institute iseni L. Ta. Karpov) in the
Card 1/2

Investigation of the Structure of the Radicals of S/076,/60/034/04/31/042
Substances Obtained by Alkylation of Aromatic Hydro- B010/3009
carbons by Means of Alcohols in the Presence of Boron Trifluoride
laboratory of A. I. dhatenshteyn. The reaction mechanism can hardly be explained
by means of the data concerning the alkylation with iso-alcohols; however, the
reaction might take place via an intermediate stage during which olefines are
formed. The structure of the alkylation products obtained was determined from
infrared spectra; particular attention was paid to the structure of the side
chain, which wle investigated on the basis of the frequency of CH oscillations
(2800-3000 0m- ). The spectra of the alkyl naphthalenes and diphenyls (Figs. 1,2),
the constants of which are given in a table, were recorded by means of an IKS-11
infrared spectrometer with thp aid of an FEOU-15 amplifier. The assumption was
confirmed that there is aweak interaction between the alkyl radicals and aro-
matic rings. The investigation results given in the paper show that in the way
described the structures of the radicals in compounds of the-t e Ar-11 (Ar -
phenyl, diphenyl, naphthyl, and R - alkyl groups from C3 to C5~Kay be deter-
mined. Papers by A. V. Topchiyev, Ta. 1. Paushking and 1. V. Kurashev'are men-
tioned in the paper. There are 2 figures, I table, and 22 references, 13 of which
are Soviet.
SUBMITTED: September 17, 1958
Card 2/2

A
6
1 1 hr. J:P
O)l
J cl 0 0 S/020/6 3 /01,-09, o6o
AUTHORS: Shukin, 11. 1., Corresponding Member, B011/BO06
A
I
S USSR, Bellckiy, I. F.
'% 'I 'I
TITLE: llydro,-enatio~i of Puran Compounds on a Skeleton Cu-Al Catalyst
PERIUDICAL: Doklady Ak.,.dcjAi nauk SSSR, 1960, V01131 , Nr 1, pp 109-112
(USSR)
AESTRACT: The authors investiLated the effects of pressure and temperature
on the sentience of the reduction of unsaturated bonds in various
compounds of the furan series. 1) The pressure determines the
direction of hydrogenolycis of the furan ring. In the pre ence
of skeleton Gu-Al catal"-st' tinder normal pressure# the s VVX
silvan rinf; is cleaved at -L'-.,,.o C-0 bond not adjacent to the
methyl ,:rou-p. 1:ctliyl --,ropyl ketone is, formed (see scheme:
rcferenec 3). itr. n i-inO elozovare, howrover, is possible in both
if :Alwii i.-, lilrdro,,enated
(G-0 bou(iu 1v2 c,~nd 1,5) 0
in the v..-,:oi- pliase before, bi,t with crossurized hydrogen.
o cuanLitien obtained of and c-`,-.no1-2 vary con-
ly with 'he prc-_zu:L-e applied. `.3 '~or t11'.._.c-.-;-.'_-vres -)ro-
der: 1 t, - ..~l
u,ote both the del,:.,-Jr; tion of -,,.ont,-~nol-2 to nethyl propyl ketone,
Cr,.rd and the clenv~ :v- of n i,~nt-or i.or: ~tion of n--!)cnt.-,nc and

.1ydroCenation of Furan Compounds on a
Skeleton Cu-Al Catalyst
Card 21-1
68816
S/'020/60/131/01/030/0'0
B011/BO06-
water. Pive to ei_ht percent tetrah,, drofuran was formed in all
reactions involvinf, prosouri,,,ed hydrogen. 2) The primary re-
action in the h.,,drot;enation of alkylfurylc'rbinol!) on skeleton
Cu-Al nortizal or increased hydrot~&n pressure is
the reduction of the hydroxyl Group, yielding the corresponding
q-alkylfurans. Under normal pressure and at 230-250' yields of
up to 95Wo are obtained. Further hydro.-enolysis of the ring
(at hiC~her temperatures) leadu to aliphatic ketones. Under
these conditiono hydroj,,enolysis of the ring is much more in- J/'
tenLe in both directions. Aliphatic alcohols and small quanti-7
ties of o(-alkyltetrahydrofurans Pre also contained in the re-
action products. 3) In the case of alkyl-o(-furyl ketones and
alkyl-(X-furylcarbinols selective reduction of the carbonyl
group under retention of the furan ring is possible in the
vapor phase. As a catalyst for this reaction, e.g., nickel, de-
posited on zinc- or cadnium oxide com be used (Ref 4). However,
the sequence of the reactions may also be different (on
platinized c_rbon). The effect of okeleton Cu-Al catalyst on
the hydroLenation of alky1furyl ketones at nornal. pressure in