Synthesis of 12-oxododecanoic acid oxime from vernolic acid

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

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564262, 564268, 562623, C07C24904, C07C25132

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054343070

ABSTRACT:
A process for producing 12-oxododecanoic acid oxime, a novel compound which can be used as a raw material in several industrial processes, is disclosed. The disclosed process relies on a renewable raw material, vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid. The process utilizes readily available chemical technology which does not involve the use of gaseous hydrocarbon or petrochemical-base feedstock. Hydrogenation of vernolic acid produces 12,13-epoxystearic acid, which can be oxidized with periodic acid to give 12-oxododecanoic acid, which can be reacted with hydroxylamine to yield 12-oxododecanoic acid oxime. A process for reducing the 12-oxododecanoic acid oxime to yield 12-aminododecanoic acid, the monomer for nylon-12, is also disclosed.

REFERENCES:
Industrial and Engineering Chemistry, vol. 62, No. 3, (1970) Wolfgang Griehl et al., pp. 16-22: Nylon-12-Preparation.
Lipids, vol. 23, No. 4 (1988), Henry Rakoff, pp. 280-284: Preparation of Methyl cis-9, cis-12, cis-15-Octadecatrienoate-15,16-d.sub.2 and Methyl cis-9,cis-12,cis-15-Octadecatrienoate-6,6,7,7-d.sub.4.

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