EXPORT OF PHTALIC ANHYDRIDE TO EUROPEAN SOVIET BLOC

• Document Type: CREST
• Collection: General CIA Records
• Document Number (FOIA) /ESDN (CREST): CIA-RDP62-00328A000100170005-3
• Release Decision: RIFPUB
• Original Classification: C
• Document Page Count: 12
• Document Creation Date: December 9, 2016
• Document Release Date: July 11, 2000
• Sequence Number: 5
• Publication Date: April 3, 1958
• Content Type: MEMO

This document is circulated for agency review prior to formal committee consideration. Agency comments, issues
or questions to be brought before the formal meeting;_should.be.reported to the Executive Secretary (Code 112-
Extension 4252) (Room 5312, Commerce Building) by the close of business
CONFIDENTIAL.
April 3, 1958
.OC DOCUP.`ENT NO. 1392 Supplement 1
TO: Chairman, Operating Committee
FRONT: Corrmerce Member
SUBJECT: Export of Phthalic Anhydride to European Soviet Bloc
Reference: OC Document 1392
if Background
In the reference document,, the Department of Commerce recommended
that three applications covering the export of phthalic anhydride
to the European Soviet Bloc be rejected. This recommendation was
concurred in by the Operating Committee. (PD 1348).
The Department stated,, in the reference document, that a technical
review was being conducted to determine whether.phthalic anhydride
should be placed on the control list. This study has been completed.
(See attachment -1),
2. Recommendation
In the light of this study, the Department of Commerce concludes
that phthalic anhydride does not qualify for either multilateral
or unilateral control; and that the rejection of applications by
the U.-S.. does not contribute to the security of the United States,
and has no effect other than to transfer the business to.European
producers.
The Department therefore proposes that future applications for the
export of phthalic anhydride to the Soviet bloc be viewed.. favorably.
Additionally, it is recommended that favorable action be taken. on a
formal appeal which has been received from the applicant in Case
No, 150697 (See attached letter from Monsanto); on a request for
reconsideration received from the applicant in Case No. 176481,
(See attached letter from Leslie Kleyman);,and on, an additional case
(No. 197744)which was recently resubmitted. This third case was
originally submitted in early February. and iras.RWAtd.
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These three cases, all of which are for the USSR, total approximately
52500.9000 lbs.
34 Strategic `valuation
An analysis of phthalic anhydride in terns of PD 1100 indicates that
the criterion for strategic rating are not met. Specifically,
phthalic anhydride is not designed.specially or used principally for
the development, production or utilization. of arms,, ammunition,
implements of war or atomic energy materials. Its military'signifi-
canoe stems from the use of products .for which- it is the raw material,
and not from the use of phthalic anhydride as such,, '
Attribute three is therefore not met.
The technology for producing phthalio anhydride is well known through-
out the world, and in any case such technology is not extractable
from. the material itself.
? Attribute four is therefore not met,
The primary military 'signVicance of phthalic: anhydride stems from
its use as a` raw material for the production of. p hthalate esters,
which are plasticizers used in making. rocket fuels and other
.military propellants (See 'table 1).
The data on Soviet bloc pro ductioii indicate that Soviet production
is of such magnitude that no critical deficiency of this material
exists.
U.S. consumption of phthal:c anhydride far ,plastic:Lzers in. 1944
was 69 . million lbs., used for cable lacquer, -insect repellants, and
propellants. Soviet bloc production?of~phthalic-anhydride is
reported as 40 to 46 'million' lb's. '.as, of.::1954, which would: be more
than ample. for propellant requirements..
Attribute 'five is therefore not met.
(It:is..interesting to note that phthalic anhydride was at one
time on List III (item 3754) but was decontrolled in 1954. It was
one of the items for vuhich the original. U.S*. position was to delete.
(JOG Doe 1/3754 dated 5/7/54)? It is not on the current U.S. list
of items. proposed for International =?con.trol. as prepared by the
Ad Hoc Subcommittee on List Review and adopted by. ]EDAC.)
B..0 Unilateral Control
The attached fact sheet shows that Western European production
capacity is 343 million pounds per year, as compared with 425 million
pounds in the United States, and that U.S. exports to Western Europe
totalled 10.4 million pounds in 1956 and 17.5 million pounds in the
first eight months of 1957 (data includes both phthalic anhydride
and phthalate esters).
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These proportions are such that U.S. unilateral controls would
clearly be ineffective. In this connection, it should be noted
that both France and Italy have included phthalic anhydride in
their trade agreements with the U.S.S.R. (hoscow D-365 dated
1/16/58; Paris D-1267 dated 1/29/58; COCOk Doc 2942B dated 2/25/58)
Under these circumstances of trade and supply potential, and in view
of the indirectness of the relationship of phthalic anhydride to
military uses, and of the small proportion of strategic as against
non-strategic uses, this commodity does not appear to qualify for
unilateral embargo control by the United States..
Attachments:
1. Fact Sheet
2. Letter from Monsanto
3. Letter from Leslie Ifleyman
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Fact Sheet .> Phthalic Anhydride march 1958
A. Description
Phthalic anhydride (P.A.) is one of the most important cyclic
chemicals. It is produced either from coal tar (via naphthalene)
or synthetically from petroleum (via orthoxylene). Some 60 -? 70
million dollars worth are produced annually in the United States.
Actual U. S. production was 331.4 million lbs. in 1955, and 315.2
million lbs. in 1956.
P.A. is a major raw material used for the production of alkyd type
surface coating resins (about 55%), esters for plasticizers (35%),
an intermediate for a red coloring compound (5%), and miscellaneous
other uses (5%).
The phthalate esters are produced by reacting P.A. with various
alcohols.
C. Technology
Production of P.A. from naphthalene involves the processes of
vaporizing, catalytic conversion, crystallization, and purifica-
tion by distillation. The anhydride is then melted and flaked.
In its production from orthoxylene, there is vaporization with
excess air to avoid explosion, catalytic conversion, condensation,
distillation and flaking. Esters are produced by reacting
alcohols with P.A. in the presence of concentrated sulfuric acid.
Equipment required must be resistant to highly corrosive chemicals,
and suitable for working with high pressure or under high vacuum.
Heat transfer controls and other controls to keep pressures and
temperatures to close tolerances are also necessary. Supervision
of equipment must be under highly trained technicians to avoid
explosions or the degradation of final products.
D. Strategic Uses
1. P.A. esters (phthalates) used as plasticizers give propellants
certain desirable. burning characteristics and keep the mixed,
solid propellants in condition during storage as such or when
incorporated in the shell or missile. (See Table 1.)
2. While peacetime usage in the U. S. is primarily for paints and
plastics, the wartime pattern of 1944 shows 122.million lbs.
of P.A. practically all allocated to military and other
essential requirements. Of this amount 38 million went into
alkyd surface coatings (largely paints) and 69 million were
used for plasticizers for cable lacquer, insect repellants,
and -for single and double base propellants of the types shown
in Table 1.
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A recent survey of U. S. work in the field of solid propellants gives
the following information on plasticizers:
1. Use; of plasticizers
For plasticizing nitrocellulose type propellants, the phthalate
esters used included the dimethyl, diethyl and dioctyl. Other
plasticizers used are esters of acetic, adipic and sebacic acids
as well as the solvents triacetin and diethylene glycol. Adipo-
nitrile is also mentioned,
The JATO unit developed for the Air Force by Standard Oil Co. of
Indiana, which was based on ammonium nitrate with cellulose acetate
as a binder, used a variety of plasticizers, including the phthal-
ates, triacetin, glycols and dinitrotoluene.
The survey states that the choice of plasticizer has an important
effect on the ballistic properties of a propellant.
2. Thy es of plasticizers
Plasticizers listed in the current Plastics Encyclopedia for use by
the plastics industry demonstrate the availability of many other
possibilities. Specifically, those groups known to be useful in
plastics include the following chemicals or their derivatives:
Abietic acid
Camphor
Ethers
Adipic acid
Caprylic acid
Ethy'.Lhexoi acid
Azelaic acid
Citric acid
Fumeric acid
Benzoic acid
Coconut oil
Glycerine
Biphemyl
Epoxy
Glycols
Hydrocarbons
Palmitic acid
Ricinoleic acid
Laurie acid
Paraffin
Sebacic acid
Malefic acid
Pelargonic
Stearic acid
Myristic acid
Pentaerythritol
Styrene
Naphthalene
Phosphoric acid
Succinic acid
Nitrile
Phthalic acid
Sucrose
Oleic acid
Polyesters
Sulfonic acid
Tall oil
Tartaric acid
Actually a list of over 300 specific chemicals is shown in the
Encyclopedia and the unlisted other chemical combinations are in-
finite in number. About half of the 300 listed are phthalates,
however, indicating the importance of this type of plasticizer for
all uses, i.e., in plastics as well as propellants. For reasons
of cost, availability and superior performance, the phthalates
appear to be the most attractive both for military and nonmilitary
uses,
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E. 2. Continued:
Production of plasticizers in the U. S. is shown in Table 2. In
1955 over 212 million pounds of phthalates were produced out of
396 million of plasticizers. In 1956 the ratio was 237 out of 417
million. Production by type of phthalate is shown in Table 3.
F. Sources of Supply
1. World Production
Available data. for the rest of the Free World indicate some 393
million pounds of capacity per annum as of 1956. This compares with
an estimated 425 million for the U. S. in the same year. (Table 4).
By contrast, the 1954 Soviet Bloc production is reported at 40 to
46 million pounds, of which the U.S.S.R. had 15 to 22 million and
East Germany most of the balance. Table 5 shows these estimates by
country.
2. International Trade in Phthalate Anhydride and its Esters, (Tables
6 and 7).
Note: The full extent of such trade cannot. be measured due to
statistical classification difficulties. Some countries
combine the anhydride with: ethers, or the anhydride with
its esters. Some countries show basket categories which
include a number of related chemicals, thereby concealing
the data completely.
G. Free World Trade with the Soviet Bloc
Recent shipments to the Soviet Bloc from Western Europe are shown in
Table 6.
France and Italy have included phthalic Anhydride in trade agreements
with the U.S.S.R.
A recent report indicates that a Dutch firm has a Russian order for
22 million pounds of P.A. The proposed source of this material is
not known.
The U. S. licensed 1.3 million pounds for the U.S.S.R. in September 1957
and 200,000 pounds for Czechoslovakia in October. The U. S. rejected
applications for an additional 2 million pounds for the U.S.S.R. in
January 1958. A request to extend the time validity for Its tons of the
P.A. licensed to Czechoslovakia was also rejected in January.
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Prior Years Control
Phthalic anhydride and its esters were formerly Item 3754 (MESL 47101-
#B 709), but were deleted during the 1954 review.
Task Group Members
BFC < Messrs. R. Stewart, F. Magnuson. L. Keiston
BDSA .. Mr. W. Lowe Walde
Defense Mr. Fred. Bates
AEC Mr. Fred C. Lee
State Mr. Thomas S. Strong
TABLE 1
a.o
lb,
Propellants which require Phthalate Esters
(Illustrative List in
Class and Description.
or Name Propellant
Small arms - .30 light rifles
Guns
Mortar
Rockets - Terrier sustainer
Western Ball Powder
Single base powder Ml
M6
Double-base propellant M8
Double base "0 G Ktt
Terrier booster Double base "0 I Y"
Nike booster Double-base 110 I Ytt
Talos booster Double base 110 I Ytt
FFAR (Aircraft folding fin) Double-base "N - 5tt
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TABLE 2
U.S. Production of Plasticizers
1955-1956
(Millions of lbs.)
Price per Pound
1955
1956
1956
Total
396
117
.32
Plasticizers, Cyclic Total
297
315
.30
Phosphoric acid esters
143
41
.32
Phthalic anhydride esters
213
237
.29
All other cyclic
plasticizers 21
41
37
.32
Plasticizers, Acyclic
100
101
.39
Adipic acid esters
11
9
.44
Azelaic acid esters 21
-
10
.142
Glyceryl monoricinoleate
0.3
0.3
.32
Oleic acid esters
12
10
.32
Phosphoric acid esters
10
7
.143
Sebacic acid esters
9
11
.58
Stearic acid esters
10
11
.24
Triethylene glycol
di(caprylate-caprate)
2
1
.41
All other acyclic
plasticizers 2/
46
43
.37
NOTES: Data for 1956 are preliminary
1/ Includes data for synthetic camphor, certain phosphoric acid
esters, toluene-sulfonamides, tetrahydrofurfuryl cleate, and
other cyclic plasticizers.
Includes data for citric and acetylcitric, azelaic, palmitic,
tartaric, and ricinoleic acid esters, and for butyl myristate,
glyceryl and glycol esters of certain fatty acids, glyceryl
tripropionate, complex polymeric materials, and other scyclic
plasticizers.
Sources U. S. Tariff Commission.
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TABLE 3
U.S. Production of Phthalate Esters - 1955-196
(Mill on lbs.)
Tn)e of Phthalate
19 5
1956
Dioctyl
30.6
31.0
Diethyl