SU311900A1 - METHOD FOR OBTAINING ACETYLEDYHYDRODYLCYCLOPENTADIENYL ETHYLIC FATTY - Google Patents

Description

This invention relates to a process for the preparation of new polycyclic fatty acid esters;

The industry of synthetic polymeric materials is associated with the development of the production of various plasticizers. In this connection, the synthesis of new compounds based on petroleum, in particular naphthenic hydrocarbons, acquires important practical and theoretical importance. In addition, the fatty acid acetyl dihydrodicyclopentadienyl esters synthesized according to the invention can be used as a feedstock for the synthesis of epoxy ethers, which, in turn, are good plasticizers as stabilizers for polyvinyl chloride and a number of other chlorinated polymers.

It is known to prepare dihydrodicyclopentadienyl ethers of monochloroacetic acid by condensation of dicyclopentadiene and monochloroacetic acid in the presence of acidic catalysts.

These esters contain one acyl group

C1-CH2-C-0-CIS1 U

:, JxixV

YC-0-6H2-C-0-6i | 1 I

D. l

contain two acyl groups, which increases their reactivity.

The proposed method for the preparation of acetyl dihydrodicyclopentadienyl ester of nary acids is based on the interaction of monochloroacetic acid dihydrodicycloeptadienyl ester with alkaline salts of fatty acids at a temperature not higher than 100 ° C.

The process is carried out mainly in the aquatic environment. The use of water as a medium contributes to the activation of the chlorine atom in chlorine ethers and thus facilitates condensation at low temperature.

By this method, 10 new acetyl dihydrodicyclopentadienyl fatty acid esters, not previously described in the literature, were synthesized. The resulting esters are clear oily liquids with a low specific odor, do not dissolve in water and dissolve well in organic solvents.

The reaction proceeds as follows:

-HgO

c.iiuCooH - con jp - cis - s - o-CH | lJ -X

h o

-С5Н „-с-о-сн-с-о-к; ь

In a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 11.6 g of caproic acid, 5.6 g of a 40% aqueous solution of KOH are charged. The mixture is heated for 0.5 hours at a temperature of 80-85 ° C and 23.9 g of monochloroacetic acid dihydrodicyclopentadienyl ester is added dropwise. Then the temperature is raised to 100 ° C and the reaction is continued for 5-6 hours. The target product is extracted with benzene, washed with water, dried, the solvent is distilled off.

and the residue is subjected to vacuum distillation. Acetyl-dihydrodicyclonentadienylcanronate is distilled at 185-187 ° C and 3 mm Hg. Art. The output of the ether 25 g, or 81.9% of theory. The acetyl dihydrodicyclopentadienyls of fatty acids given in the table are synthesized in the same way.

Compounds of general formula

R-C-0-CH2-C-0- CHi

oo

Table

Subject invention

The method of producing acetyl dihydrodicyclopentadienyl fatty acid esters, characterized in that monochloroacetic acid dhydrodicyclopentadienyl ester

subjected to interaction with the alkaline salt of the corresponding fatty acid at a temperature not higher than 100 ° C; with the subsequent selection of the target product by known techniques.