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The preparation of hydroxystearic acids from red oil (Commercial oleic acid)
Author(s) -
Munns W. O.,
Kairys S.,
Manion Dilys A.,
Meade E. M.
Publication year - 1963
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02645783
Subject(s) - saponification , oleic acid , chemistry , acetic acid , anhydrous , organic chemistry , catalysis , yield (engineering) , saponification value , distillation , acid value , hexane , fatty acid , chromatography , nuclear chemistry , biochemistry , materials science , metallurgy
Abstract The hydroacetoxylation of red oil (commercial oleic acid) in acetic acid solution has been studied. The optimum hydroacetoxylation conditions were obtained under anhydrous conditions using sulphuric acid as a catalyst at: a concentration of 1% (based on the wt of red oil). at a reaction temp of 70C, at a ratio of acetic acid: oleic acid of 3蝘1.Some 70 hr were required under these conditions to obtain maximum (60舑70%) addition to the double bond. Some 50% (based on the wt of red oil) of pure hydroxystearic acids was isolated from this acetoxylation mixture by simultaneous deacetylation and esterification, followed by distillation, saponification, acidification, and crystallization of the acids from hexane. For the isolation of a less pure (50舑60%) hydroxystearic acid, the mixture following distillation was hydrogenated, saponified, and acidified. Suitable hydrogenation conditions were found to be 110舑115C, at a pressure of 300 psi for 4 hr. Selectol C was the catalyst of choice used at a concentration of 0.2% (nickel based on the wt of fatty acids). An 85% wt yield of this product was obtained.