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Production of vinylic unsaturation by partial dehydrobromination of vicinal dibromo fatty derivatives
Author(s) -
Rheineck A. E.,
Sreenivasan B.
Publication year - 1969
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/bf02544368
Subject(s) - linseed oil , chemistry , bromine , degree of unsaturation , double bond , vicinal , organic chemistry , medicinal chemistry
The reaction of methyl dibromostearate with metal cyanates in dimethyl formamide or dimethyl sulfoxide results in the disappearance of the peak at 548 cm −1 in the IR spectrum due to the ‐C‐Br group. Chemical analysis of the products reveals the presence of residual bromine. Gas liquid chromatography and nuclear magnetic resonance examination of the products shows the presence of olefinic unsaturation and this indicates that partial dehydrobromination has occurred. The result is a double bond with one carbon atom attached to a bromine atom. This structure has some vinylic characteristics. The application of this process to partially brominated linseed oil yields a dehydrobrominated linseed oil, with residual bromine. This oil has drying properties very similar to raw linseed and safflower oils.