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Synthesis of dodecanedioic acid from vernonia galamensis oil
Author(s) -
Ayorinde Folahan O.,
Powers Fiona T.,
Streete Ludwig D.,
Shepard Robert L.,
Tabi Dorothy N.
Publication year - 1989
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/bf02669953
Subject(s) - saponification , petrochemical , chemistry , chromic acid , yield (engineering) , organic chemistry , raw material , materials science , metallurgy
Abstract Dodecanedioic acid, currently available from elaborate synthesis utilizing petrochemical feedstock, was synthesized from Vernonia galamensis oil via an efficient, relatively simple three‐reaction sequence that involved the room temperature oxidation of 12,13‐epoxystearic acid. The first and second steps of the reaction scheme were saponification and hydrogenation, both of which were almost quantitative. The third reaction, involving chromic acid oxidation of the resulting epoxy acid, afforded greater than 50% of the theoretical yield of dodecanedioic acid (>95% purity, m.p. 123–125°C; lit. m.p. 128–130°C).