9‐Aminononanamide and nylon‐9 from azelaaldehydic derivatives of soybean oil

Abstract 9‐Aminononamide, a potential intermediate for nylon‐9, was prepared from soybean oil via alkyl soyate, aldehyde oil or soybean amides. All three routes involved various sequences for reductive ozonolysis, reductive amination and ammonolysis. The preferred route is through the alkyl soyates, although the other two have fewer steps. The amino amide is a water‐soluble, strongly basic solid that rapidly absorbs atmospheric carbon dioxide and is readily hydrolyzed to 9‐aminononanoic acid. Although the amino amide is selfpolymerizable in limited degree, the preferred monomer for nylon‐9 is the amino acid. Other new compounds prepared and characterized include azelaaldehydamide, bis(8‐carbamoyloctyl)amine; N‐(8‐carbamoyloctyl)‐8‐methoxycarbonyloctylamine; 9‐hydroxynonanamide; and dimers of the amino amide and the amino ester.