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The preparation of fatty acid chlorides

1946; Wiley; Volume: 23; Issue: 1 Linguagem: Inglês

10.1007/bf02593227

1558-9331

S. T. Bauer,

Synthesis and Biological Activity

Oil and SoapVolume 23, Issue 1 p. 1-5 Article The preparation of fatty acid chlorides S. T. Bauer, S. T. Bauer Southern Regional Research Laboratory, New Orleans, LouisianaSearch for more papers by this author S. T. Bauer, S. T. Bauer Southern Regional Research Laboratory, New Orleans, LouisianaSearch for more papers by this author First published: 01 January 1946 https://doi.org/10.1007/BF02593227Citations: 31 One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture. AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Summary Fatty acid chlorides of lauric, myristic, palmitic, stearic, oleic, elaidic, and linoleic acids were prepared using phosphorus tri- and pentachlorides, oxalyl chloride, and thionyl chloride as chlorinating agents. On the basis of yields, ease of handling, and cost of reagent, phosphorus tri- and pentachlorides are superior to other chlorinating agents for the preparation of the higher fatty acid chlorides for use as intermediates in the preparation of pure saturated fatty acid glycerides of known structure. The unsaturated fatty acid chlorides are, however, best prepared from oxalyl chloride. The use of phosgene, which has been patented for the preparation of acid chlorides, failed to effect efficient conversion of the higher fatty acids to the corresponding chlorides. The analysis of the fatty acid chlorides by conversion to anilides provides a simple and easy means for ascertaining the extent of conversion of fatty acids to chlorides. By means of this method it is possible to follow readily the course of the reaction in order to determine when complete conversion of fatty acid to fatty acid chloride has been effected. Citing Literature Volume23, Issue1January 1946Pages 1-5 RelatedInformation