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Large‐scale synthesis of methyl cis ‐9, trans ‐11‐octadecadienoate from methyl ricinoleate
Author(s) -
Berdeaux O.,
Christie W. W.,
Gunstone F. D.,
Sebedio J. L.
Publication year - 1997
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/s11746-997-0018-z
Subject(s) - chemistry , chromatography , organic chemistry , stereochemistry
Abstract The conjugated linoleic acid methyl cis ‐9, trans ‐11‐octadecadienoate has been prepared on a large scale from methyl ricinoleate. Methyl ricinoleate was purified from castor esters by a partition method. It was converted to the mesylate, which was reacted with a base (1,8‐diazabicyclo[5,4,0]‐undec‐7‐ene) to give a product that contained 66% of the desired ester. Two urea crystallizations produced a product containing 83% methyl cis ‐9, trans ‐11‐octadecadienoate, the identity of which was confirmed by gas chromatography linked to mass spectrometry and by Fourier transform infrared spectroscopy. The remaining impurities were methyl cis ‐9, cis ‐11‐ and cis ‐9‐, trans ‐12‐octadecadienoate.