Synthesis of 12-aminododecanoic acid

Details Synthesis of 12-aminododecanoic acid Synthesis of 12-aminododecanoic acid

1995-03-15

1996-06-25

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554103, C07C 9900

Patent

active

055301487

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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