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Synthesis of azelaic acid and suberic acid from Vernonia galamensis oil
Author(s) -
Ayorinde Folahan O.,
Osman Gamal,
Shepard Robert L.,
Powers Fiona T.
Publication year - 1988
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/bf02542380
Subject(s) - azelaic acid , dibasic acid , ricinoleic acid , nitric acid , chemistry , sebacic acid , adipic acid , organic chemistry , castor oil
We have demonstrated the potential of Vernonia galamensis seed oil as a source of dibasic acids. Reaction of nitric acid with V. galamensis oil afforded a homologous series of dibasic acids that include butanedioic acid, pentanedioic acid, hexanedioic acid (adipic), heptanedioic acid (pimelic), octanedioic acid (suberic), nonanedioic acid (azelaic), decanedioic acid (sebacic), and undecanedioic acid. Using a combination of chloroform extraction and subsequent water crystallizations, we have isolated suberic acid (∼95% purity by GC) and azelaic acid (∼95% purity by GC). The isolated yield of suberic acid is 15% and of azelaic acid is 11%. Reported reaction of nitric acid with ricinoleic acid (from castor oil) gave 8.8% suberic acid and 7.2% of a mixture of suberic and azelaic acids.