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Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula . It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in . The and carboxylate salt of pelargonic acid are called pelargonates or nonanoates.
The acid is named after the pelargonium plant, since oil from its leaves contains esters of the acid.
Alternatively, pelargonic acid can be produced in a two-step process beginning with coupled dimerization and hydroesterification of 1,3-butadiene. This step produces a doubly unsaturated C9-ester, which can be hydrogenated to give esters of pelargonic acid.
A laboratory preparation involves permanganate oxidation of 1-decene.
Synthetic esters of pelargonic acid, such as methyl pelargonate, are used as flavorings. Pelargonic acid is also used in the preparation of and . The derivative 4-nonanoylmorpholine is an ingredient in some .
The ammonium salt of pelargonic acid, ammonium pelargonate, is a herbicide. It is commonly used in conjunction with glyphosate, a non-selective herbicide, for a quick burn-down effect in the control of weeds in turfgrass. It works by causing leaks in plant cell membranes, allowing chlorophyll molecules to escape the chloroplast. Under sunlight, these misplaced molecules cause immense oxidative damage to the plant.
The methyl form and ethylene glycol pelargonate act as against Meloidogyne javanica on Solanum lycopersicum, and the methyl against Heterodera glycines and M. incognita on Glycine max. p.229.
Esters of pelargonic acid are precursors to lubricants.
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