Method of synthesizing fatty acid esters of ascorbic acid

Details Method of synthesizing fatty acid esters of ascorbic acid Method of synthesizing fatty acid esters of ascorbic acid

1978-01-27

1979-04-24

Randolph, John D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07D30762

Patent

active

041511786

ABSTRACT:
A high-yield process of producing essentially pure fatty acid esters of ascorbic acid is disclosed which gives significantly increased yields of esters using a simple reaction scheme and an excess of relatively inexpensive, recoverable fatty acids, as opposed to use of an excess of ascorbic acid. The process hereof comprises reacting an ascorbic acid isomer and a saturated fatty acid in concentrated sulfuric acid at ambient or relatively low temperatures, followed by ester recovery. Surprisingly, enchanced yields are obtained by using a molar excess of fatty acid relative to the ascorbic acid, 98-99% concentrated sulfuric acid as opposed to 95% sulfuric acid, and/or a molar ratio of the sum of the fatty acid and ascorbic acid to sulfuric acid of from about 0.1 to 0.3.

REFERENCES:
patent: 2350435 (1944-06-01), Wells et al.
patent: 2408897 (1946-10-01), Wells et al.
Delga et al., Ann. Pharm. France vol. 15, pp. 691-697 (1957).
Wertheim, Textbook of Organic Chemistry, 3rd Ed., frontispage, and pp. 231 to 233, The Blakiston Co. NY (1951).
Chemical Abstracts, vol. 68, abst. no. 96105r (1968), (brief abstract of Shionogi & Co., Japanese Pat. 20,051 supra).
Tanaka, Yakugaku Zasshi, vol. 86, pp. 376-383 (1966).

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