PubAg

13-aminotridecanoic acid from erucic acid

Author:

Greene, J.L., Burks, R.E.

Source:

Industrial and engineering chemistry product research and development 1969 v.8 no.2 pp. 171

ISSN:

0196-4321

Subject:

erucic acid, Crambe abyssinica, nylon, ozone, chemical reactions, esterification, hydrolysis, yields

Abstract:

13-Aminotridecanoic acid, the monomer for nylon 13, was synthesized from commercial erucic acid or its derivatives by several methods in a study to determine the method of choice, which involved oxidative ozonolysis of eruconitrile, followed by esterification before isolation to give methyl 12-cyanododecanoate. The cyano ester was then catalytically reduced and hydrolyzed, without isolation of intermediates, to give very pure 13-aminotridecanoic acid in 55 to 60% yield from the eruconitrile. Almost equally convenient was a method starting with oxidative ozonolysis of methyl erucate to the half ester of brassylic acid, which was then converted successively to the amide-ester, nitrile-ester, amino ester, and amino acid. Other methods tried were significantly less desirable because of low yields and difficult purifications.

Agid:

31359

Handle:

10113/31359

http://dx.doi.org/10.1021/i360030a015