Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1998-07-01
1999-08-10
Ramsuer, Robert W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
C07C25529
Patent
active
059361140
ABSTRACT:
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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Di Cosimo Robert
Fallon Robert Donald
Gavagan John Edward
Herkes Frank Edward
E. I. Du Pont de Nemours and Company
Ramsuer Robert W.
Sackey Ebenezer
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