RESEARCH IN DYES AND DYE INTERMEDIATES AT NIOPIK, RUBEZHNOYE

• Document Type: CREST
• Collection: General CIA Records
• Document Number (FOIA) /ESDN (CREST): CIA-RDP81-01030R000100340004-9
• Release Decision: RIPPUB
• Original Classification: S
• Document Page Count: 9
• Document Creation Date: December 27, 2016
• Document Release Date: July 25, 2013
• Sequence Number: 4
• Publication Date: January 8, 1953
• Content Type: REPORT

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CENTRAL INTELLIGENCE AGENCY
INFORMATION REPORT
COUNTRY
SUBJECT
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USSR (Voroshilovgrad Oblast) ,
Research in Dyes and Dye Intermediates
at NIOPiK, Rubezhnoye
Di
DATE OF INFO.
PLACE ACQUIRE
REPORT
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NO. OF PAGES
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-,REQUIREMENT
REFERENCES
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THE SOURCE EVACUATIONS IN THIS REPORT ARE DEFINITIVE.
THE APPRAISAL OF CONTENT IS TENTATIVE.
(FOR KEY SEE REVERSE)
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STATE
ARMY
NAVY
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AIR
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FBI
AEC
OSI Ev
Note: Washington Distribution indicattid By "X"; Field Distribution By "s".)
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COUNTRY : USSR (Voroshilovgrad
REPORT
A 7 goi/5",3
Oblast) DATE DISTR.
91/83ECT s Research in Dyes and Dye Intermediates at NO. OF PAGES 8
NIOPiK, Rubezhnoye
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THIS IS UNEVALUATED INFORMATION
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RESEARCH ON '-DYES FOR COLOR PHOTOGRAPHY AT RUBEZHNOYE
1. group of 23 German organic and physical chemists
were transported to a development laboratory at Ru ez toye, 50X1-HUM
USSR, to work on development probLems connected with the manufacture
of known German dyes by the faotory "Chimkombinat" at Rubezhnoye. 50X1-H UM
Filiale NIOPiK was a laboratory in Rubezhnoye specifically organized
by MOM (Nauchnyi Institut Organicheskii Promezhotohnii-Produktov e
Krasitoleyi), Moscow, in order to permit the transported German group
to work within the USSR under Soviet direction, but at the same time
to restriet their activities to their own laboratory. Liaison between'
the 'Waco* NIOPiK office and the laboratory, and between both the
"Chiikombinat" plant and its technical service laboratory, was conducts&
by a single liaison officer. General problems were assigned to the
group by,the.NIOPiK liaison officer, and were concerned with applied
research onlys i.e., adaptation of German processes for the manufacture
of textile and color-photography dyes to Soviet manufacturing fecal**.
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chemical intermediates.
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2.
German chemists who were selected
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by the Soviets primarily to work
on the development of
dyes and
dye components for color photography
were transported
to
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Rubezhnoye in Novemlier 1946,
and for a period of about
nine
months given laboratory
apace in the very poorly equipped 50X1-HUM
and limited Central Laboratory
of Chimkombinat. For some
time a
rumor had circulated that was eventually to be
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to a new laboratory in Moscow that was ostensibly to be
for the
sole use of the technical group,
but nothing further was heard,
and instead________ moved in
August 1947 to the new NIOPiK Branch 50X1-HUM
Laboratory Nauchnyi Institut
Organioheskyi Promezhotchnii-Produktov
Krasiteleyi; Scientific Institute for Organic Dyes and Dye Inter-
mediates) in Rubezhnoye. 50X1-HUM
3. Shortly after arrival in Rubezhnoye were visited by a 50X1-HUM
committee of three that consisted of UVAROV, who was the represent-
ative of the Chemical Ministry that controlled NIOPiK; Prof.
VOROSHCHOV, the scientific consultant to NIOPiK, Moscow; and Mrs.
RASCHEVSKAYA, the head of the Central Laboratory of Chimkombinat.
The latter interviewed each specialist and assigned him a problem.
Later scientific One-Year Plans that included suggestions 50X1-HUM
made were drafted.
Laboratory Poorly Equipped
4. The laboratory had its own library and in addition also had access
to the fairly good Chimkombinat library, equipped with scientific
literature in the form of journals, books, and both German and
Soviet reports. Upon request could obtain documents from
NIOPiK, Moscow. The laboratory was very poorly equipped, however,
and particularly at the beginning lacked common supplies such as
thermometers, flasks, condensers, etc. More complex items such
as microscopes, refractometers, viscosimeters, constant temperature
baths etc., could be obtained from the so-called "trophy storage,"
of German equipment. However, the needs of Central Laboratory
took Precedence over those of the NIOPiK Branch Laboratory.
Balances were of Soviet manufacture, but were insensitive and of
low precision according to German standards. As time progressed,
the marked deficiency in laboratory equipment was alleviated by
imports from Germany; and it was of some interest that
better equipped than were equivalent laboratories in Germany
with ground-glass articles due to these importations. Glassware
of Soviet origin was arilable, but was of very poor quality; and
mas only because of
very gifted-Soviet glassblower
able to maintain adequate stocks of glass apparatus.
5. However, in no case can it be said that laboratory was well
equipped, either with glassiare or with chemicals. Common
reagents such as sodium sulfate, potassium chloride, potassium
bromide, etc., were unobtainable. It was necessary to prepare
these reagents from the appropriate acids and bases or from
stocks of reagents that had been originally imported from Germany,
as for example potassium bromide, which was prepared from a small
supply of potassium bromate that happened to be in stock. Purifica-
tion of reagents for, analytical purposes was almost always
necessary, such as for example the purification of hydrochloric
acid by distillation. The comparatively low availability of Soviet
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6.
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chemicals was not a question of their availability; the USSR
Norm Catalog listed a wide selection, but was rather the result
of the cumbersome transportation system. For example, flammable
chemicals were shipped for short dietances only by truck, and
the convenient German practice of shipping such materials by
rail was unknown. On the whole, the quality of Soviet chemicals
when delivered was rather poor,
Necessary tools such as slide rules, magnifying glasses, glass
cutters, typewriters (German), were in very short supply, and were
not provided by the Soviets Paper was also in exceedingly short
supply for all purposes, and for a long period it was necessary
to use paper sacks or wrapping paper for the required reports0
typewriter paper of rather
available on a limited basis0
poor quality was made
7. In spite of all these difficulties, the German group managed
to conduct significant work. learned quickly to improvise,
just as do the Soviets who are masters of improvisation, and it
was quite obvious expected to um all knowledge
in every aspect of activities there.
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Soviet Personnel of Inferior Caliber
8. Soviet laboratory assistants mostly women, were at our disposal,
and usually came untrained except for a limited knowledge
of German. As might be expected, a few were gifted and eager
to learn and very eager to rectify their obvious lack of practical
laboratory training, All Soviet technical personnel were required
to take courses regulariy and to take an examination once a year,
from the results of which they were classified according to
position. A few came with limited formal training, but this was
the exception rather than the rule.
9. less success with the Soviet chemists who occasionally
came to work , Their training at that time was poor,
particularly in laboratory experience, and only a few of the
younger chemists were willing to further their own education
by self-study in order that they might prosecute a problem
independently. On the whole, the average Soviet chemist seemed
to be afraid to pursue independently his own problems, in part
it seems because of his fear to accept responsibility for his
own decisions and in part because ota well-defined inferiority
complex. He had the tendency to follow written instructions
uncritically (i.e., "cook-book chemistry") and to use formulae
rather than reasoning, and consequently often gave the impression
that he was rather ungifted for his work. On the whole, the
relationships between the Soviet and the German chemists in the
laboratory were quite good, and were free of invidious national-
istic or racial comparisons, but it was obvious that these
social relationships could not be continued into private life.
RESEARCH PROJECTS AT NIOPiK BRANCH LABORATORY'
10,
occupied with
the NIOPiK Branch Laboratory was
a number of projects, briefly describe.
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a. Vat Dyes, especially Thioindigo Compounds: This project
was assigned from the start and continued until the group
was returned to Germany in 1951. Dr. WVTKE (now group
leader at Wolfen) as advisor and planner, and Prof. Dr.
RIECHE,Dr.HaFFMANand, Were occupied in this
group throughout. -Dr. W. NlCHTIR and Dr. HAIL were
assigned occasional tasks. In 1949 the vat dye and
anthraquinone compounds development section was expanded
and Dr. GNUECHTEL, Dr. SCHULZE were assigned
to the group.
b. Dye Intermediates: At first, the projects in this class
were those of interest to Chimkombinat. For example,
Dr. CARO worked on the nitration of chloro-
benzene and toluene and the isolation of the nitration
products. Other problems included the preparation of
intermediates such as trichlorobenze (by Dr. ENGELMANN),
2, 6-dichlorotoluene (Dr. RICHTER), sulfonation of various
naphthalenes (Dr. SCHULZE). In general, these syntheses
were undertaken in order to produce small quantities of
dyes as standards of purity.
0. Dye Components for Color Photography: Several research
assignments that had as their objective the improvement
of quality of color-film dye components and improvements
in the yields of the reactions that produced them were
assigned to Dr. HAIL and to Dr. GNUECHTEL.
d. Indicators: In 1948 the Bayer series of indicators
were produced in laboratory scale by Dr. THURM, Dr. SCHULZE,
Dr. CARO, Dr. GNUECHTEL, ,Dr. LEHMANN . Their
application was investigated by Dr. FUCHS, 50X1-HUM
Inorganic Developments: Insofar as they were applicable
to the synthesis and development of dyes, the regenera-
tion of sulfuric acid and the preparation of thionyl
chloride and sulfuryl chloride were investigated by
Dr. WOLFF.
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f. Continuous Processes: Plans and apparatus for the
continuous production of p-nitraniline and of 2-amino-
anthraquinone were developed by Dr. KRATZ and Dipl. Ing.
BRINKMANN.
g.
Miscellaneous: Dr. KELLER investigated the carboxyla-
tion reaction of phenol to yield salicylic acid, whereas
Dr. SCHUSTER and Ing. RANK investigated the oxidation
of naphthalene to phthalic anhydride and the decarboxyla-
tion of phthalic acid to benzoic acid. To a small extent,
synthetic detergents like "Igepone" and "Igepale" as
well as the dye-fixative dicyanamide-formaldehyde water-
soluble resin "Solidogene" were investigated by Dr.
BRODERSEN. Fur dyes were investigated by Dr. LEHMANN.
Certain insecticides and fungicides marketed under the
tradename "EUlan" by Bayer, Leverkusen, were under develop-
ment by Dr. MAIER-BODE.
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h. Services: An analytical laboratory under the direction
of Dr. A. RICHTER wad at our disposal. His previous
work in Germany was with the development of ion-exchange
resins, but he did no work on them while at the NIOPiK
Branch Laboratory. However, his special knowledge in
dehydration techniques was often of great assistance.
The physicist of the group, Dr. FUCHS, was occupied with
various problems in instrumentation.
the NIOPiKiBranch Laboratory
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a. Development of an Analytical Method for the Determination
of meta-Nitrochlorobenzene in an Isomeric Mixture. The
technical nitration of chlorobenzene yields only about
two per cent of the meta isomer, and although the
chlorination of nitrobenzene is preferred because it gives
better yields of the meta isomer, the
Chimkombinat plant (o basis of" the results of the
analytical procedure developed) that a grade of
meta-nitroohlorobenzene of purity sufficient for the
preparation of the dye Sulfur Black could be obtained
by modification of the existing process to include a
regenerative step. It would have been beet if the meta
derivative could have been isolated by an efficient low-
pressure distillation?but this equipment was not avail-
able in the plant. analytical method was based on
the determination of the freezing points of a ternary
Mixture of isomers, previously freed of nitrobenzene
and dinitrochlorobenzene by distillation. Attempts to
enrich the meta content by selective hydrolysis with
steam of the ortho and para isomers was not successful.
analytical method was not
previously described in the litekature that was avail-
able s the reports of the I. G. Farben and reports
issued by the Chimkombinat.
b. Isolation of meta-Nitrotoluene from Technical Mixtures.
In this case it was not necessary to conduct
laboratory work, because the reports from the I. G.
Parbenindustrie that were available described an
excellent procedure for the isolation of pure meta-
nitrotoluene by distillation,
number of recommendations to the plant to this effect,
including an analytical procedure for the meta-isomer.
There was available to the plant the use of a 53-plate
? bubble-cap column that had been delivered to Chimkombinat
for reparations; and although this column was quite suit-
able for vacuum distillation and separation of"the three
isomers, the plant was unable to make it achieve the
desired separation.
Consequently, the plant never
did succeed in preparing the pure meta isomer.
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? Development of a Process to Produce Ethyl Acetoacetate:
A suitable process was designed for the preparation of
'ethyl acetoacetate from ethyl acetate and anhydrous
sodium ethylate, based on reports from Hoechst and from
the NIOPiK-Moscow laboratory. The process was tested
at Moscow, and pilot plant erected at an unknown
location.
d. Development of a Process to produce Phthalodinitrile:
A suitable process was recommended, based on reports
originating from Ludwigshafen and from NIOPiK-Moscow,
and involved the catalytic dehydration of the reaction
product of phthalic anhydride and ammonia. The original
process called for bauxite, or activated alumina; but
since this was not available in the USSR, a process based
on phosphoric acid as a contact catalyst was recommended.
This process also was tested at NIOPiK-Moscow,
.e. Preparation of Indicators in a Laboratory Scale:
Industrial literature was not available, and details
for the preparation of such indicators were obtained
from the open literature.
(1) o-Cresylphthalein: Approximately 200 grams.
of this indicator were prepared by the
condensation of phthalic
anhydride with o-cresol,
with toluene sulfonic acid 03
as a catalyst.
cit
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? (2) Bromor0R01 Green (Tetrabromo-m-cresolsulfo-
pntnaleio): Attempts to prepare this common
indicator from saccharin as a starting\material
were not successful.
f. Special Synthesis of Indanthrene Brilliant Green FFB:
(Dimethoxydibenzanthrone). (Russian name: Kubovi-Yarko
Zelenyi C). The steps that were of interest to the plant
were:
(1) The oxidative 'condensation of dibenZanthronyl to
' .dihydroxydibenzanthrones
WL11?
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pr-ri7,50y.
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. (2) The methylation of dihydrozydibenzanthrone by
methyl tolusnesulfonate or in both cases (HO)
benzene sulfonate to dimethoxydibenzanthrones
0
(Ago otH3
0
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This dye was produced in the plant, and the
objective of this particular project was to
clarify the reaction mechanism and to produce a
standard sample of high-quality dye. A further
objective was to suggest means of diminishing
the consumption of sulfuric acid instep (1);
and the sulfuric acid
consumption could be minimized if the quality of
the manganese dioxide used in otep (1) were raised
such that it was free of silica, with the con-
sequence that the purification step be eliminated 50X1 HUM
that required that the dihydroxydibenzanthrone be
dissolved in concentrated sulfuric acid and repre-
cipitated by the addition of water,
This research was
guided by a plant report from I. G. Ludwigshafen,
a short note from CIBA, and a prewar report from
the Moscow, laboratory.
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On the whole, the quality of the Indanthrene
Brilliant Green FIB that was produced at the plant
was not up to German standards. In an effort to
correct this condition, the 50X1-HUM
fact that the fastness of the dye would be affected
by impurities introduced during manufacture; 50X1-HUM
In general, the plant experienced a great many
difficulties in manufacture, to judge from the
fairly large number of questions
g. Development of Methods for Manufacturing Anthrasole Dyes:
These were vat dyes that were applied to the fiber in the
form of the water-soluble hemisulfate of the leuco
(reduced) form, and then oxidized in situ. This class of
arently was unknown in the USSR,
he reports issued bjr I. G. Ludwigshafen in
or er to conduct the development work. The following
dyes, neither of which were new, were developed
fc
Soviet use 7
The dyes were:
(1) Anthrasole Brilliant Green FIB (Russian name:
Kybozom Yarko ZeleynAC), or hemisulfate of
leuco dimethoxydibenzanthrones
Nt 0 SO NM,
Cawa
0 0
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(2) Anthrasole Golden Yellow GK(Russian name: Kybozom
Zolotieto Zheltyi JK), or herieulfate of
dibenzpyrene quinone:0 a,
04 4
05.901.
The hemisulfates were obtained by reduction of
the parent vat dye with a.metal powder in anhydrous
pyridine, with simultaneous eulfation by means of
chlorosulfonic acid. In connection with this re-
search, a procedure for the pre- 50X1-HUM
paration of anhydrous pyridine by azeotropic
distillation of the wet pyridine, and also developed
preparative procedures for the preparation of
dimethylaniline-p-sulfoilic acid and of "Trioloxyd"
(the polyethylene oxide derivative of triethanolamine).
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