Nonanoic acid

Description

Nonanoic acid , also called pelargonic acid, is an organic compound composed of a nine - carbon chain terminating in a carboxylic acid with structural formula CH₃(CH₂)₇COOH. Nonanoic acid forms esters—nonanoates. It is a clear, oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in chloroform, ether, and hexane.
Its refractive index is 1.4322. Its critical point is at 712 K ( 439 °C ) and 2.35 MPa.

Chemical properties

clear colorless liquid

Chemical properties

Colorless or yellowish, combustible, oily liquid. Faint odor.

Chemical properties

Nonanoic acid has a fatty, characteristic odor and a corresponding unpleasant taste. May be prepared by oxidation of methylnonyl ketone; by oxidation of oleic acid; or from heptyl iodide via malonic ester synthesis.

Chemical properties

Nonanoic acid has a fatty, characteristic odor and a corresponding unpleasant taste. This compound is also reported as having a cheese, waxy flavor

Originator

Pellar,Crookes Barnes, US ,1960

Occurrence

Nonanoic acid is a fatty acid which occurs naturally as esters in the oil of pelargonium. Synthetic esters, such as methyl nonanoate, are used as flavorings.
Nonanoic acid is also used in the preparation of plasticizers and lacquers.
The derivative 4-nonanoylmorpholine is an ingredient in some pepper sprays.
The ammonium salt of nonanoic acid, ammonium nonanoate, is used as an herbicide.

The Uses of Nonanoic acid

The primary uses of this acid are in organic synthesis and in the manufacture of lacquers, plastics, pharmaceuticals, synthetic odors and flavorings, gasoline additives, flotation agents, lubricants, and vinyl plasticizers. Nonanoic acid has found some use in pharmaceutical preparations and as a topical bactericide and fungicide. It is also used in herbicides.

The Uses of Nonanoic acid

Intermediates of Liquid Crystals

The Uses of Nonanoic acid

In the production of hydrotropic salts (hydrotropic salts form aqueous solutions which dissolve sparingly soluble substances to a greater extent than water); in the manufacture of lacquers, plastics.

What are the applications of Application

Nonanoic acid is a lipid used in the preparation of plasticizers and lacquers

Definition

ChEBI: A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.

Preparation

Nonanoic acid is produced by malonic ester synthesis, from Heptyl iodide.

Manufacturing Process

A body of liquid, 18 inches high, comprising a 35% (by weight) solution of technical (95%) oleic acid in n-propanol, is maintained at a temperature of 86°C in a reactor. The solution also contains dissolved therein 0.042% by weight of cobalt, in the form of cobalt naphthenate. From the bottom of the reactor very fine bubbles of air are passed into and through the solution at the rate of about 0.3 cubic feet per minute, measured at standard conditions, per square foot for 72 hours. The gases leaving the reactor are first passed through an ice water reflux condenser and then vented to the atmosphere. At the end of the 72 hour period the reaction mixture is separated into its components. It is found that 60% of the oleic acid has been consumed in the reaction. For each pound of oleic acid consumed there are obtained 0.30 pound of azelaic acid (representing an efficiency of 46%, calculated on the basis that the technical oleic acid is 100% oleic acid), 0.13 pound of pelargonic acid (representing an efficiency of 23%) and 0.21 pound of 9,10dihydroxystearic acid (representing an efficiency of 19%).

Therapeutic Function

Fungicide

Aroma threshold values

Detection: 3 to 9 ppm

Taste threshold values

Taste characteristics at 10 ppm: fatty, waxy, and cheesy with a mild, sweet, creamy background

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 195, 1971 DOI: 10.1021/ja00730a033
Organic Syntheses, Coll. Vol. 2, p. 474, 1943
Tetrahedron Letters, 9, p. 5689, 1968

General Description

Nonanoic acid occurs naturally in Pelargonium L′Her. It one of the flavor constituents of cooked rice, acerola fruit, licorice and yogurt.

Agricultural Uses

Herbicide, Fungicide: Pelargonic acid occurs naturally in many plants and animals. It is used to control the growth of weeds and as a blossom thinner for apple and pear trees. It is also used as a food additive; as an ingredient in solutions used to commercially peel fruits and vegetables

Trade name

CIRRASOL®-185A; ECONOSAN®; EMERY® 202 (mixture with n-octoic acid); EMFAC®-1202; HEXACID® C-9; PELARGON®; SCYTHE®; WEST AGRO ACID SANITIZER®

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. A severe skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

By oxidation of methylnonyl ketone; by oxidation of oleic acid; or from heptyl iodide via malonic ester synthesis

Potential Exposure

Pelargonic acid, a naturally occurring fatty acid herbicide/fungicide. It is used to control the growth of weeds and as a blossom thinner for apple and pear trees. It is also used as a food additive; as an ingredient in solutions used to commercially peel fruits and vegetables; in the manufacture of lacquers, plastics and pharmaceuticals.

Purification Methods

Esterify the acid with ethylene glycol and distil the ester. (This removes dibasic acids as undistillable residues.) The acid is regenerated by hydrolysing the ester in the usual way and is distilled in vacuo. [Beilstein 2 IV 1018.]

Incompatibilities

Heated vapors may form explosive mixture with air. May react violently with strong oxidizers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders or dust. Incompatible with strong bases and silver compounds; mixture with some silver compounds may form explosive salts of silver oxalate.

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Contact a licensed disposal facility about surplus and non-recyclable solutions. Burn in a chemical incinerator equipped with an afterburner and scrubber. Extra care must be exercised as the material in an organic solvent is highly flammable. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.