The Preparation of the Esters of some Substituted Sebacic Acids from Oleic Acid

Abstract

threo-9,10-Dihydroxyoctadecanoic acid (I) like its erythro-isomer gives good yields of 2-hydroxy-2-octyldeoandioic acid (II) when fused with alkali. Under similar conditions 9,lO-diketo-octadecanoic acid gives a somewhat lower yield of this same acid and is considered a probable intermediate in the conversion of I to II. Esters of II have been tested as lubricants at low temperatures and as plasticizers. They are too heat sensitive to serve as lubricants. The octyl side chain renders them less effective as plasticizers than esters of sebacic acid. The 2-ethylhexyl ester of 2-octyldecandioic acid (III), derived from II, has properties which fit it for use as a lubricant.