Howard University

Folahan O Ayorinde

Chukwuma P Nwaonicha

Mahmoud Hassan

A process for producing 12-oxododecanoic acid oxime, a novel compound which can be used as a raw material in several industrial processes, is disclosed. The disclosed process relies on a renewable raw material, vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid. The process utilizes readily available chemical technology which does not involve the use of gaseous hydrocarbon or petrochemical-base feedstock. Hydrogenation of vernolic acid produces 12,13-epoxystearic acid, which can be oxidized with periodic acid to give 12-oxododecanoic acid, which can be reacted with hydroxylamine to yield 12-oxododecanoic acid oxime. A process for reducing the 12-oxododecanoic acid oxime to yield 12-aminododecanoic acid, the monomer for nylon-12, is also disclosed.

Synthesis of 12-aminododecanoic acid

Nylon-11 monomer, 11-aminoundecanoic acid, is synthesized from 12-oxododecanoic acid oxime in a three-step reaction sequence which involves a Beckmann rearrangement, Hofmann degradation and hydrolysis. The aldoxime acid is hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid. This amide is then treated with a solution of sodium methoxide and bromine at 70.degree.-80.degree. C. to give 11-(methoxycarbonylamino)undecanoic acid, which upon basic hydrolysis and subsequent neutralization, yields the 11-aminoundecanoic acid.

Synthesis of nylon-11 monomer

The present invention concerns a method for the production of olefin anhydrides, such as acrylic anhydride and methacrylic anhydride, via reactions between an aromatic acid chloride, such as benzoyl chloride, and carboxylate ions of the olefin acid corresponding to the anhydride to be produced. The method of the invention may be conducted without the use of a solvent, catalyst, polymerization inhibitor, or an external source of heat. Moreover the acrylic anhydrides of the invention can be used to produce high yields of acrylate esters by means of room-temperature reactions, without mineral acid catalysis.

Acrylate ester

Synthesis of 12-oxododecanoic acid oxime from vernolic acid

A chromatographic process for deacidification of vegetable oils at ambient temperature. According to the process, which can be retrofitted into deacidification operations using miscella refining or solvent extraction, crude vegetable oil is dissolved in a solvent such as isopropyl alcohol and passed through a column of activated alumina (aluminum oxide) at room temperature. The process, which eliminates physical contact between both oil and an alkaline reagent and oil and water, simplifies subsequent bleaching processes by also removing some color pigments. The spent alumina can be reactivated by washing it with a dilute solution of sodium hydroxide or potassium hydroxide.

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Kettering, MD, United States of America

Folahan O Ayorinde