E.i. Dupont De Nemours and Company

Dsm N.v.

Other

E. I. Du Pont Nemours and Co.

Frank Edward Herkes

John Edward Gavagan

Robert Donald Fallon

Robert Di Cosimo

Lech Wilczek

Michael G Bramucci

Robert Dicosimo

Wim Buijs

Nicolaas F Haasen

Samuel L Lane

Henricus F Wolters

Leo Ernest Manzer

Kostantinos Kourtakis

David P Higley

William A Beck

Robert Pestman

Jay Leslie Snyder

Jeroen Af Boogers

This invention relates to a process for the preparation of a 3-hydroxycarboxylic acid from a 3-hydroxynitrile. More specifically, 3-hydroxyvaleronitrile is converted to 3-hydroxyvaleric acid in high yield at up to 100% conversion, using as an enzyme catalyst 1) nitrile hydratase activity and amidase activity or 2) nitrilase activity of a microbial cell. 3-Hydroxyvaleric acid is used as a substitute for &#x3b5;-caprolactone in the preparation of highly branched copolyester.

3-Hydroxycarboxylic acid production and use in branched polymers

3-hydroxycarboxylic acid production and use in branched polymers

This invention relates to a process for producing 5-methyl-1-R-2-pyrrolidone or 5-methyl-2-pyrrolidone, wherein R is a hydrocarbyl or substituted hydrocarbyl, by reductive amination of levulinic acid utilizing a metal catalyst, which may be optionally supported.

Production of 5-methyl-1-hydrocarbyl-2-pyrrolidone by reductive amination of levulinic acid

This invention relates to a process for the preparation of a 3-hydroxycarboxylic acid from a 3-hydroxynitrile. More specifically, 3-hydroxyvaleronitrile is converted to 3-hydroxyvaleric acid in high yield at up to 100% conversion, using as an enzyme catalyst 1) nitrile hydratase activity and amidase activity or 2) nitrilase activity of a microbial cell. 3-Hydroxyvaleric acid is used as a substitute for &egr;-caprolactone in the preparation of highly branched copolyester.

The present invention provides a process for making 3-hydroxyalkanenitriles comprising the steps of reacting an alkenylnitrile, wherein the alkenylnitrile is an alkenyl-2-nitrile or an alkenylnitrile which under reaction conditions isomerizes to form an alkenyl-2-nitrile, in the presence of a base with benzyl alcohol to form a 3-benzyloxyalkanenitrile adduct and then partially hydrogenating the adduct in the presence of a trace amount of HCl to form the 3-hydroxyalkanenitrile or fully hydrogenating the adduct to form a 3-hydroxyaminoalkane.

Process for making 3-hydroxyalkanelnitriles and conversion of the 3-hydroxyalkanelnitrile to an hydroxyaminoalkane

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.

Preparation of lactams from aliphatic .alpha..omega.-dinitriles

Nitrilase-producing acidovorax facilis

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

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.

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

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.-nitrile-carboxylic 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 arnidase (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.

The present invention relates to a process for the cyanobutylation of ammonia, an alkylamine or hydrazine with 3- and 4-pentenenitrile and mixtures thereof to form alkylaminonitriles.

Cyanobutylation of ammonia, alkylamines and hydrazine with

A process for the hydrogenation of 3-aminopentanenitrile to produce 1,3 diaminopentane using a Raney.RTM. cobalt catalyst promoted with chromium, nickel, molybdenum, iron, manganese or mixtures thereof. Performing the reaction in the presence of aqueous caustic (e.g., alkali metal hydroxide) enhances the selectivity to 1,3 diaminopentane.

Production of 1,3-diaminopentane by hydrogenation of

This continuous process for preparing an aqueous mixture of .di-elect cons.-caprolactam and 6-aminocaproic acid and/or 6-aminocaproamide by involves, as the reductive amination step, continuously contacting 5-formylvaleric acid or an alkyl 5-formylvalerate in water as solvent with hydrogen and an excess of ammonia in the presence of a ruthenium on carrier, as a catalyst, wherein the carrier is at least one of titanium oxide or zirconium oxide. The aqueous mixture can be used to prepare .di-elect cons.-caprolactam.

Process to continuously prepare an aqueous mixture of episilon

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 aimnonium 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.-monocarboxylic 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.

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

The present invention relates to a process for selective dimerization of 2-pentenenitrile or mixtures of 2- and 3-pentenenitrile in the presence of a strong base to form 1,3-dicyano-2-ethyl-3-hexene.

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Wilmington, DE, United States of America

Frank Edward Herkes