Preparation of lactams from aliphatic .alpha.,.omega.-Dinitiles

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United States of America Patent

PATENT NO 5922589
SERIAL NO

09108729

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Abstract

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A process for the preparation of five-membered or six-membered ring lactams from aliphatic .alpha., .omega.-dinitriles has been developed. In the process an aliphatic .alpha.,.omega.-dinitrile is first converted to an ammonium salt of an .omega.-nitrilecarboxylic acid in aqueous solution using a catalyst having an aliphatic nitrilase (EC 3.5.5.7) activity, or a combination of nitrile hydratase (EC 4.2.1.84) and amidase (EC 3.5.1.4) activities. The ammonium salt of the .omega.-nitrilecarboxylic acid is then converted directly to the corresponding lactam by hydrogenation in aqueous solution, without isolation of the intermediate .omega.-nitrilecarboxylic acid or .omega.-aminocarboxylic acid. When the aliphatic .alpha.,.omega.-dinitrile is also unsymmetrically substituted at the .alpha.-carbon atom, the nitrilase produces the .omega.-nitrilecarboxylic acid ammonium salt resulting from hydrolysis of the .omega.-nitrile group with greater than 98% regioselectivity, thereby producing only one of the two possible lactam products during the subsequent hydrogenation. A heat-treatment process to select for desirable regioselective nitrilase or nitrile hydratase activities while destroying undesirable activities is also provided.

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Patent Owner(s)

  • E. I. DU PONT DE NEMOURS AND COMPANY

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Inventor(s)

Inventor Name Address # of filed Patents Total Citations
Di, Cosimo Robert Rockland, DE 10 91
Fallon, Robert Donald Elkton, MD 13 102
Gavagan, John Edward Wilmington, DE 57 745
Herkes, Frank Edward Wilmington, DE 11 72

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