RESEARCH ON ORGANIC DYE STUFFS AT THE RUBEZHNOYE CHEMICAL COMBINE

• Document Type: CREST
• Collection: General CIA Records
• Document Number (FOIA) /ESDN (CREST): CIA-RDP80-00810A001500740010-3
• Release Decision: RIPPUB
• Original Classification: S
• Document Page Count: 12
• Document Creation Date: December 16, 2016
• Document Release Date: June 1, 2005
• Sequence Number: 10
• Publication Date: November 3, 1953
• Content Type: REPORT

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CENTRAL INTELLIGENCE AGENCY
INFORMATION REPORT
SECRET/
COUNTRY USSR (Voroshilovgrad Oblast)
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DATE OF INFO.
Research on Organic Dye Stuffs at the
Rubetnoye Chemical Combine
This Document contains information affecting the Na-
tional Defense of the United States, within the mean-
ing of Title 18, Sections 793 and 794, of the U.S. Code, as
amended. Its transmission or revelation of its contents
to or receipt by an unauthorized person is prohibited
by law. The reproduction of this form is prohibited.
REPORT NO.
DATE DISTR.
NO. OF PAGES
REQUIREMENT NO.
REFERENCES
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1. The Rubezhnoye (N 49-01, E 38-23) Chemical Combine produced,principally, organic
dye stuffs, intermed,ete products,, and some base materials. The plants, built
by American firms.in 1926, were partly dismantled during World War II and.the
buildings were heavily damaged. From 1946 reconstruction was slow.
For example the power station which had been under construction as early as
1946 had not been completed
zz w o rected the works of the German research tegam. Soviet personnel of the
laboratory. included two women secretaries,, a woman bookkeeper, a woman librarian,
and three workmen. Several Soviet chemists and women assistant chemists were
assigned to the German specialists.
The Soviet chemists were not equal in training to the Geraans. They were un-
acquainted with many chemical processes and.conspicuously lacking in the ability
to perform chemical calculations. In general they were docile and eager to
learn but were distracted from their duties by competitions and political in-
doctrination. They were 'specially reluctant to assume responsibility and worked
2. The manager of the Combine, not a specialisty was aState or Party functionary
who directed not only. the wor1~ . but also most of the provi,q can and clothing
shops, hotels, culture buildings, and other installations it Rubezhnoye. The
technical manager of the Combine was the chief engineer who waste supervisor
of department and. shop managers. he laboratory
of the German specialists employe n. the works was directed by Bulkin (fnu), a
rather young Soviet chemist, who was afterward sentenced to several years of
penal servitude for unknown reasons. He was succeeded by Viktor Yemilyevioh
Reyrifart, a.Moscow the :ist who was given the title of director after the
laboratory had been taken -over by the NIOPIK (nauchny institut organicheskikh
produktov i krasitelyey "Scientific Institute for Organic Products and Dye Stuffs).
Second to Reynfartp who was a high,-ranking Party functionary, was Daputy Direc:.t,or
`tyoyanov (fnu) who had, been awarded a Stalin prize for scientific works in 1951
a d h di
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only when given positive orders by supervisors. The women assistant chemists
were very diligent and were constantly instructed by chemists in both chemical
and political subjects. Chemists,, as well as assistant chemists, were organized
according to work and salary grades; they could be promoted or demoted to higher
or lower grades.
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25X1 4. twenty-three deported German specialists. twenty-one from
the of en Farbenfabrik and two from the Deutsche Hydrierwerke in Rodleben ar-
rived at R.ubezhnoye. With the exception of one physicist and two engineers all
were chemists. Only three of them were employed in their proper field; the
others had to familiarize themselves with new subjects. Their duties were made
known to them by Professor Voroshtsov (fnu), director of a Moscow scientific dye
stuff laboratory, who determined the possibilities of employment and the salary
for each member of the German team. Salaries were between 4,000 and 7,000. rubles.
After reading scientific literature for one month, the Germans were assigned a
temporary laboratory with small and simply..equipped rooms. The supply of current
and gas was irregular. The gas, which was a..benzo.l-air mixture, was so irregularly
supplied that the burners often went out and.benzol vapor appeared in the rooms.
This was extremely detrimental to the health of the working staff in the laboratory
and affected the hemoglobin level of the blood., decreasing it from .90to 70 per-
cent. The glass equipment was very poor and tins. and glasses for conserves were
used to a very large extent. From time to time glass, equipment delivered as
reparations, or resulting from dismantlings, arrived from Germany but most of
it was stolen before reaching-he laboratory. Writing paper was scarce, too, and
packing paper was generally used for writing. In mid-1947, the German team
moved into a new laboratory with better equipment which had been constructed for
them. The installations were not perfect but the laboratory ensured undisturbed
work to a certain degree. A library on the fifth story of the building became
useful gradually. All major chemical works had been seized in Germany.
5. A so--called teihn.ikutn, an experimental plant where all major experiments
of the processes developed in the laboratory were executed under commercial
conditions, was attached to the laboratory. Although equipped with modern
instruments from Germany and Hungary, the tkhniktzm. lacked implements and
tools. It was directed by Popov (fnu), a Soviet chemist who was assisted
by five other Soviet chemists. They worked in three shifts, and the German
specialists had only to express their wishesion the technique of the pro-
ceases to control the experiments. They were never informed whether the
processes were adopted.for regular production nor were they allowed to
enter the production shops.
.La,41 Research on_Ryestuffs and D eetuff Intermediates.
6. Ethox-Cleve acid, intermediate product for dyestuff.
(I ) Naphthol OH -p_- Ethyl alcohol C HS5OH
C10H80 0( r Sulfuric acid H280
(II) Naphthol ethyl ether 0C2H5 $ Nitric acid 03) ~+5i
C1211120 in organic(HNsolvent, 401-'C
(III) Nitro-ethoxy-naphthalene N02
C12H11O3N OC2H5. +
ryl\~ Iron (Fe )
Hydrochloric acid
_(IV) Amino-ethoxy-naphthalene
C12H130 N
HH2 0/25 ? Suuls ric acid
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03?
(V) Amino -ethoxy-naphthalene- N12
sulfonic acid C12H13O4SN HSO3
(VI
l~amino-2-ethoxy-6-naphthalene-
sulfonic acid sodium salt
C12H12O SNNa
The etherification (I), in the Soviet Union, is allegedly supposed to
be performed with boric acid (HBO ) as a catalyst. An orientation ex-
periment failed and was not repeated. The nitration (II) proceeds
smoothly. It results, also, in the formation of other nitro compounds
which, in the main, remain in solution, while the 1-nitro compound
precipitates. The L-nitro-2-ethoxy-naphthalene (III), which has been
filtered off and dried,, is sufficiently pure for further treatment.
The reduction to the amino compound (IV) with iron powder is difficult
and tedious. The amino compound so obtained will be distilled in a
vacuum, then dissolved in and recrystallized from ethyl alcohol, (C2H5OH).
Sulfonating (IV) with 98%b sulfuric acid and salting out with sodium
chloride offer no obstacles at all.
'j. Diehloro tro-aniline, intermediate product for dyestuff.
(I) Nitro-aniline
C 6B6O2N2
(II) 2,6-dichloro-p-nitro aniline
. C6H4Cl2O2N2
+ Chlorine (C12)
in hydrochloric acid (Ml)
NP2
o"
2
Chlorination with gaseous chlorine is to be preferred, by far, to that
of a chlorate cio or NaC1O3) , Any excess of chlorine must be avoided,, since
,,CO)
guinone like (O . . C. ,CO ) compounds form immediately and,, in addition,
bH-CH
the yield promptly drops off. As long as p-nitro-aniline-chlorine hydrate
is still present, a. test by the spot method on paper containing lignin
brings out a blood-red coloration, which is an excellent test for the
completion of the reaction.. By dissolving it in, and then crystallizing
it from concentrated sulfuric acid (H2H0j), or by dissolving it in, and
then recrystallizing it from methanol (CH30H), the product can be purified.
Allyl mustard oil, for use on the film area.
(I) Glycerol CH OH 2 (C3H803) I
CHOH
1
CH2 OH
formic acid
HOOCH
CH200CH
(II) Glycerol diformate
(C5H805) CHOH +2arous.chloride (CuCZ)
pyrolysis according to ,Sandmeyer---~
CH200CH
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III) Allyl formate.
(CjH602)
CH2
II
IH
CH200 CH
+ hydrochloric acid (Hci)
coned., up to 50'C
(IV) Allyl chloride
(C3g5C1) CH
CH2C1
(V) Allyl mustard oil CHI
11
(C4H5NS)
+ ammonium thioc anate
I1u1 CNS rearrangement
CH
I
CH2'NsCmS
The water formed as the result of esterification with formic acid is
gradually distilled off in a vacuum; the glycerol diformate, after that,
is not further purified. The pyrolysis (III) takes place between 1800 and
2600, and must be run very slowly, since completing it. too quickly results
in other cleavage products. In conversion to allyl chloride (III), one
must take into consideration that with hydrochloric acid weaker than 30
percent, the yield drops off rapidly. The final transition to mustard
oil is accomplished most readily with ammonium thiocyanate (IV), less
readily with potassium.thiocyanate (KCNS), and least. readily with sodium.
thiocyanate (NaCNS).
4itxo-benzoyl chloride, Parazol G, parazol G-aci.d,, intermediates for
he yellow' components or color rij.m.
(I) Nitro-benzoic acid
(C7H504N)
(II) nitro.benzoyl chloride
(C_740 CIN ')
(III) Nitro-benzpyl acetic ester
(C11H11o5N)
(IV) Parazol G-ester
(C17H1008N)
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~. thionyl chloride 60012 . or
phosphorus pentachloride (PC15 Y
~. sodium salt of acetoacetic ester
C 6'H1101,Na
000CH3
CO0CH2.CO002H5
(V) Parazol G-acid
(C17H1208N)
CO0CH20CO.NH
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The object of the above work was, on the one hand, to seek reasonably. to
purify p-Nitro-benzolyl chloride through sublimation, which, however,
proved unavailing in respect to the problem of apparatus. Following the
instruction of a Soviet expert, the p-nitro-benzoyl chloride
in the Soviet Union, was distilled in a vacuum; this, however, did not
prove safe. In addition, the difficult condensation with acetoacetic ester
was thoroughly studied, and it was found that the success, aside from
the pH value (hydrogen ion concentration),is solely dependent on the
purity of the nitro-benzoyl chloride. Also, by means of the following
stage of operation, in itself easily pursued, and through the introduc-
tion of a very pure p-nitro-benzoyl chloride,the.yield can be considerably
increased. The final stage: the condensation of parazol G-acid, by means
of stearyl chloride, to the finished yellow component,could not be
accomplished, since a sufficiently pure stearic acid tCH3'(CH2)i6.CO2Hj
was not available.
10. p-Methoxy benzoyl acetic ester, intermediate for a yellow component of
color film.
(I)
Hydroxy benzoic acid
(Oxy-benzoic acid)
(C7H603)
(II) Methoxy-benzoic acid
(C8Hgo3)
(III) Methoxy benzoyl chloride
(C8H7C102)
MCI
(IV) -Methoxy benzoyl acetic ester
(C12H1504)
CO,CH30002C2H5 (2)
Here the problem, above all, is to find a method of determination for
p-methoxy benzoyl acetic ester (IV). A method was worked out by coupling
the ester with diazo solution (sodium nitrite, NaNO ,t hydrochloric acid,
HC1). This work was superseded, because in the meantime, in Moscow, a
polarographic method of determination was discovered. However, p-methoxy
benzoyl acetic ester, which hitherto had been known only as a liquid, could
by this experiment be prepared in a crystallized form for the first time.
The pure ester has a fine hawthorn aroma.
11. Eriochrome blue-black B, azo dye,
ester, nitrocellulose lacquer).
(I) Naphthol
(C10Hgo)
(II) Nitroso naphthol
(C10H702N)
(III) Amidol adid
(C1OH9osN)
+ dimethyl sulfate [(CH3.O)2S03J
and potassium hydroxide (KOH)
-~- phosphorus trichloride
PCl3
-J- sodioacetoaeetic.ester
C6H110Na
~- sodium nitrite (NaNO._)
sulfuric acid H2SO4
N
H + sodium bisulfite (NaHSO,
sulfuric acid H2S0.
0~ .
NH2
H
so3H
is processed on a dye for cellulose
+ sodium nitrite (NaNO2)
hydrochloric acid (HCl
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(Iv) C10H7O4C1SN2
-6-
N2C1
03
(v) Eriochrome blue-black B
(C20Hl4055N2 )
3
The introduction of the nitroso group (I) poses no difficulties. In
the same manner, the reduction and sulfonation (II) performed in a single
operation gave little trouble. Contrary to the data of FIERZ-DAVID, the
maximum yield amounts to 78-80 percent of the theoretical. The diazotized
amidol acid (IV) couples with oC naphthol, in a caustic alkaline solution
(potassium hydroxide [KOHJ or sodium hydroxide [NaOHJ) to form
eriochrome blue-black.
12. Metanil yellow, indicator dye.
(I) Nitro-benzene
(C6H502N)
(II) Nitro-benzene sulfonic acid
(C6H5o5SN)
(III) Aniline sulfonic acid
(C6H703SN)
(IV) Diazochlorsulfonic acid
(C6H503C1SN2)
(V) Metanil yellow
(C18H11+O3SN)
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+ oC naphthol (C10H8O)
S03
03H
+ Fuming sulfuric acid (H2S0) ))
~. Iron (Fe).
Sulfuric acid H2S0j)
+ Sodium nitrite NaNO )
Hydrochloric acid H l)
+ Diphenyl amine C H5 ) NH
I 2r
Ethyl alcohol (C2H5.OH
The sulfonation (I) and reduction (II) proceed smoothly. The coupling with
Biphenyl amine (IV) was undertaken in an ethyl alcohol solution. In methyl
alcohol'(CH3OH), duller dyes are formed.
13. Indanthrene red.violet RH, vat dye of the thioindigo series.
(I)
o-Toluidine
(C7H9N)
+ Acetic anhydride f(CH3.CO)207
or Formic acid HC02H
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(II) Acet-o-toluidide
(C9H110N)
-7-
3
CO0CH3
-+- Chlorine (C12 )
(III) Dichloro aceto-o-toluidide
(c9H9oc12N)
01-11 ~L-Cl t n_ - - >_ rTr,.Tr~
(IV) Chloro amino toluene
(c7H9clN)
(V) Diazodiehloro amino toluene
(C7H6C12N2)
(VI) C14H12C12S2N4
C3
(V) C11 H12CX2S2
(VI) C7H6c1S
C1
(VII) C9H9c1028
Sodium nitrite (NaN02)
Hydrochloric acid HC1
-~- Sodium entasulfide
""-
Na2S5)a at 700C
Sulfuric acid (H280
+ Chloro acetic acid CH C1.CO2H
Sodium hydroxide NaOH)
.CH2.C02H L Sulfuric acid (H
.50 )
2
(VIII) Thio- 3B - acid
(C9H9C102S)
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(3)
S-S -eOO,\ + Iron (Fe)
.CH2.CO2H -f- Chloro sulfonic acid
(Cis03H
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14.
(IX) Thionaphthene chloride
(C9H7clos)
(X) Indanthrene red violet RH
(C18H14cl2o2S2)
-~- Bromine (Br)
First, following the old process of I.G0Farben, the o-toluidine (I) was
subjected to acetylation. The diacetyl compound is chlorinated (II) in an
aqueous suspension and saponified under pressure with sodium hydroxide
(NaOH) or potassium hydroxide (KOH). Besides 5-chloros2-acetylaminotoluene,
3--chloro-2?acetylaminotoluene is also formed. Both chlorine compounds
are separated by distillation, for which, however, very highly effective
columns are required. These columns were not available in Rubezhnoye.
Instead of products with a minimum freezing point of 26?C, only prod-
ucts with a freezing point of from 16?C to 18?C were obtained in this manner.
Further, a method was discovered whereby both chlorine products could be
separated by agitating the aqueous solutions of the hydrochlorides with
chlorobenzene. In this manner, the more weakly basic 3-chloro-2aminotoluene
was almost quantitatively dissolved in the solvent. In the aqueous
layer, enriched 5-.ehloro?2-aminotoluene hydrochloride remains. Later,
an operation was performed in accordance with instructions received from
Moscow, whose source remained unknown, in compliance with one which produces
the formyl compound of o-toluidine in chlorobenzene. The formyl compound
does not have to be isolated, but is directly chlorinated in the chloroben
zene solution (C6H 5C1) and processed further. The 5-chloro-2-aminotoluene
obtained in this manner is of excellent quality. The 3-chloro compound
remains in solution in the chlorobenzene, but, for the most part, passes
over into chlorinated quinone compounds. The process is more expensive
than that of I.G.Farben, and besides the 3-chloro compound is lost. The
advantage lies solely in the fact that one can obtain a pure product
without any highly effective fractionating apparatus. The diazotization
proceeds normally (IV), yet the conversion with sodium pentasulfide
(Na2S)(V) presents certain difficulties. The Na2S5 solution is applied
at 700C, and the diazo solution is permitted slowly to run into it, in
order to assure the immediate decomposition of the explosive diazodisulfide
,compound. Since the diazo solution itself is quite readily decomposed,
cane should be taken at the influx that the solution itself does not
become warm before it has reached the reaction mass. This stage of the
operation, at one beginning point of the process, might present the
greatest difficulty. The reduction (V) and the glycination (VI) present
no obstacles. The thio-3-B-acid (VIII) is isolated and dried. The
thionaphthene compound (IX) forms quickly through the action of the
chloro sulfonic acid on the thio-3B-acid. (VIII). In order to obtain a
dye which conforms to standard, the chloro sulfonic acid employed must
be especially pure, particularly in regard to a content of oxidizing
substances, otherwise the dyes will take on a blue tinge. This dye was
stricken from the production program of the Rubezhnoye combine, since
a sufficiently pure chloro sulfon.ip acid was not available.
Vat printing black BL, vat dye.
(I) Naphthylamine sulfonic acid
(c10H903SN)
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+ Sodium nitrite (NaNO2)
Hydrochloric acid HC1
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(II) Chloro naphthalene: sulfonic
acid (C10H7C103N2S)
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+ Cuprous chloride (OtzCl)
Sodium chloride(NaCl)
(III) Chloro naphthalene sodium
sulfo acid (C10H6C1O3SNa)
+ Zinc dust (Zn)
Sulfuric acid (H2SO451
(IV) Chloro naphthalene sulfide
(C10H7C1S)
(V) Chloro naphthalene thio-
glycolic acid (C12H9C102S)
- Chioro acetic acid (CH0CICOOH
Potassium Hydroxide
? Sulfuric acid
~-H2SO4
(VI) The same As (V)
(VII) C12H8C120S
(veil) C12H7e1oS
(XII) Indanthrene.rinting black
C20H9BrC102SN
(XI) Bromoisatin chloride
(C8H,BrC1ON)
(X) Bromoisatin
(C8HkBr02N)
(IX) Isatin
(c8H5o2N)
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? Phos. horus trichloride
(PCl3
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The diazotization (I) and the Sandmeyer reaction (II) present no diff-
iculties. The 8-Chloro naphthalene-l--sulfonic acid sodium salt (III)
is isolated. The further processing to 8-chloro naphthalene -1-
thioglycolic acid (IV) also offers no obstacles, whereas the condensation
of the thionaphthalene compound with bromoisatin chloride (XII) is
sensitive. If, in the production of bromoisatin chloride (X), the
hydrogen chloride formed is not drawn off and the operation is not
immediately carried further, dyes with muddy, dirty shades are formed.
The dye was prepared in all stages by a German expert in the technical
institution of the combine.
15. Dibromo isoviolanthroneo vat dye.
(i) Benzanthrone
(C17H10o)
(II) Benzanthrone bromide
(III) C 31H17028
IV) Isoviolanthrone
(o34Hi6o2)
(V) Dibromo isoviolanthrone
(C34H1i.Br2o2 )
-{- potassium. hydroxide (KOH)
alcoholic
-}- Bromine (Br2) -
in water
The bromination of benzanthrone (I), sulfidization (II) and desulfuri-
zation (III) proceed smoothly. The bromination of isoviolanthrone,
following a Soviet patent: of Krol'i.k', way' supposed. to take
place in an aqueous suspension (IV) at 30?C, and with a quantity of
bromine amounting to 600 per cent of the theoretical. This was not
the case. All dyes prepared in this manner were too reddish. The
German expert discovered that dyes according to type can be obtained
at 70?C, with 300 per cent of bromine.
+ Bromine
Br2)
-il- Sodium sulfide (Na2S)
in an autoclave
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16. Dibromo.dibenzo pyrenequinone, vat dye.
(I) 1, 5 Dibenzoyl naphthalene
(C2441602)
(II) Dibenzo pyrenequinone
(C201202)
(III) Dibromo dibenzo pyrenequinone
(C24H10Br2O2)
6
B'r
+Aluminum chloride Aid
Manganese dioxide (Mn02
The preparation of the dye proceeds without any particular difficulty,
with a moderate. yield, to be sure. Application of manganese dioxide proved
the latter to be absolutely essential as a hydrogen-absorbing substance.
17. Vat sols, ester salts of vat dye compounds.
Example: .0 0
11; C
(I) Thioindigo ! LS/ - ~\S
'-(II) C16H1002S2
- Iron (Fe) Pyridine (C5H5N)
Chloro sulfonic acid C1SO3H
+ Pyridine sulfate
c5H5NSO3
o.SO -NH
3. HN_03S.Q_.C
(III) C2812008S1+N2 6I-.
Soda (IV) Vat sol of
Na2CO3 Thioindigo
(C16H808S1+Na2 )
03Na Na03S
The quality of the iron used (I) for the reduction of the thioindigo is
important for the course of the operation. A special reduction iron is
best. The German expert prepared from five to six kg of indigo dyes
the appropriate vat sole, i.e. depending on the solubility, either the
sodium salt or the potassium salt (III). In one case which involved a
pink dye, the salt of triethanolamine was prepared (ECU 6r0HJ3N).
Previously, two to three moles of ethylene oxide 9CH2)20 per ethanol
group had been added to the base. This vat sol was a syrup-like, brown
liquid, whereas all the other were in the form of white or weakly-colored
crystals.
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1'. This formula should be written ((CH3)2. S04-7.
2. This formula should be written CO.CH2.CO2C2H5.
3. This formula should be written NH2.
4. Very'likely this is the Soviet scientist L. Krolik who is known for
his work in organic chemistry.
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