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Nylon-9 via 9-aminononanoic acid from soybean oil
- Miller, W.R., Pryde, E.H., Awl, R.A., Kohlhase, W.L., Moore, J.
- Industrial and engineering chemistry product research and development 1971 v.10 no.4 pp. 442
- soybean oil, nylon, ozone, esters, hydrolysis, biopolymers, chemical reactions
- 9-Aminononanoic acid was prepared from soybean oil by a four-step process. Alcoholysis of the oil gave alkyl esters of the component fatty acids. Reductive ozonolysis of these esters gave an alkyl azelaaldehydate used for reductive alkylation of ammonia. The alkyl 9-aminononanoate was not isolated but hydrolyzed directly to 9-aminononanoic acid. Yields in the reductive alkylation-hydrolysis were better than 90% of crude amino acid purified by precipitation from water with an organic nonsolvent. Polymerization by heating at atmospheric pressure gave nylon-9 of high molecular weight. Nylon-9 fibers prepared by melt spinning had strengths comparable to those of commercial nylons.