Union Carbide Chemicals & Plastics Technology Corporation

Union Carbide Corporation

Uop Lcc

Union Carbide Chemicals and Plastics Company, Inc.

Union Carbide Chemicals & Technology LLC

Kurt Damar Olson

Thomas Carl Eisenschmid

John Robert Briggs

Diane Lee Packett

Anil Sakharam Guram

Erik Bruce Tjaden

David Robert Bryant

Stephen W King

John Michael Maher

Steven W Kaiser

David James Schreck

Ailene Gardner Phillips

Elaine Susan Brigham

Bernard C Ream

Johnathan Eugene Holladay

Arthur Roy Doumaux, Jr

Eric Bruce Tjaden

Daine Lee Packett

This invention relates in part to processes for producing one or more substituted or unsubstituted unsaturated alcohols which comprise reacting one or more substituted or unsubstituted alkadienes with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted unsaturated alcohols. The substituted and unsubstituted unsaturated alcohols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted unsaturated alcohols as principal product(s) of reaction.

Processes for producing unsaturated alcohols

This invention relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam, which comprise (a) converting one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanal, optionally in the presence of a catalyst or a catalyst and promoter, to one or more substituted or unsubstituted hydroxyamides, e.g. 6-hydroxycaproamide, and/or one or more substituted or unsubstituted epsilon caprolactam precursors, e.g., 6-aminocaproamide, epsilon caprolactone, epsilon caprolactone oligomers and esters of 6-hydroxycaproic acid and mixtures thereof, and (b) converting said one or more substituted or unsubstituted hydroxyamides and/or said one or more substituted or unsubstituted epsilon caprolactam precursors, optionally in the presence of a catalyst or a catalyst and promoter, to said one or more substituted or unsubstituted epsilon caprolactams; wherein the amount of byproducts resulting from reduction and/or reductive amination of said one or more substituted or unsubstituted hydroxyaldehydes, e.g., 1,6-hexanediol, aminohexanol, and the like, is no greater than about 10 weight percent, preferably no greater than about 5 weight percent, and more preferably no greater than about 1 weight percent, of the total of said one or more substituted or unsubstituted hydroxyamides and/or one or more substituted or unsubstituted epsilon caprolactam precursors. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted epsilon caprolactams as principal product(s) of reaction.

Processes for producing epsilon caprolactams

This invention relates in part to processes for producing one or more substituted or unsubstituted 1,6-hexanediols which comprise subjecting one or more substituted or unsubstituted penten-1-ols to reductive hydroformylation in the presence of a reductive hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted 1,6-hexanediols. The substituted and unsubstituted 1,6-hexanediols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted 1,6-hexanediols as principal product(s) of reaction.

Processes for producing 1,6-hexanediols

This invention relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise subjecting one or more substituted or unsubstituted alkadienes to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols. The substituted and unsubstituted 1,6-hexanediols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted 1,6-hexanediols as principal product(s) of reaction.

This invention relates in part to processes for producing one or more substituted or unsubstituted saturated alcohols which comprise reacting one or more substituted or unsubstituted alkadienes with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted saturated alcohols. The substituted and unsubstituted saturated alcohols produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted saturated alcohols as principal product(s) of reaction.

Processes for producing saturated alcohols

This invention relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam, which comprises: (a) subjecting one or more substituted or unsubstituted alkadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and neutralization with a base to produce one or more substituted or unsubstituted pentenoic acid salts; (b) subjecting said one or more substituted or unsubstituted pentenoic acid salts to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors; and (c) subjecting said one or more substituted or unsubstituted formylvaleric acid salts and/or said one or more substituted or unsubstituted epsilon caprolactam precursors to reductive amination in the presence of a reductive amination catalyst and cyclization optionally in the presence of a cyclization catalyst to produce said one or more substituted or unsubstituted epsilon caprolactams. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted epsilon caprolactams as the principal product(s) of reaction.

This invention relates to a composition comprising (a) epsilon caprolactam and (b) one or more of 5-�4,5-di(3-carboxypropyl)-2-pyridyl!pentanoic acid or salt or amide, 4-�4,5-di(2-carboxypropyl)-2-pyridyl!-2-methylbutanoic acid or salt or amide, 2-�2-(2-carboxybutyl)-5-(1-carboxypropyl)-4-pyridyl!butanoic acid or salt or amide, 5-�3,5-di(3-carboxypropyl)-2-pyridyl!pentanoic acid or salt or amide, 4-�3,5-di(2-carboxypropyl)-2-pyridyl!-2-methylbutanoic acid or salt or amide, 2-�-2-(2-carboxybutyl)-5-(1-carboxypropyl)-3-pyridyl!butanoic acid or salt or amide, 5-amino-4-methylpentanamide, 4-amino-3-ethylbutanamide, 5-�4,5-di(4-hydroxybutyl)-2-pyridyl!pentanol, 4-�4,5-di(2-methoxypropyl)-2-pyridyl!-2-methylbutanol, 2-�2-(2-methoxybutyl)-5-(1-methoxypropyl)-4-pyridyl!butanol, 5-�3,5-di(4-hydroxybutyl)-2-pyridyl!pentanol, 4-�3,5-di(2-methoxypropyl)-2-pyridyl!-2-methylbutanol, 2-�2-(2-methoxybutyl)-5-(1-methoxypropyl)-3-pyridyl!butanol, 5-amino-4-methyl-1-pentanol, 5-imino-2-methyl-1-pentanamine, 5-amino-2-methyl-1-pentanol, 5-imino-4-methyl-1-pentanamine and 2-butyl-4,5-dipropylpyridine, wherein the weight ratio of component (a) to component (b) is at least about 99 to 1. The epsilon caprolactam compositions are useful in the preparation of nylon 6.

Epsilon caprolactam compositions

This invention relates in part to processes for producing one or more substituted or unsubstituted aldehyde acid salts, e.g., epsilon caprolactam, which comprises subjecting said one or more substituted or unsubstituted unsaturated acid salts, e.g., pentenoic acid salts, to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted aldehyde acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted aldehyde acid salts as the principal product(s) of reaction.

Process for producing aldehyde acid salts

This invention relates in part to processes for producing one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanals, which comprise subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to reductive hydroformylation in the presence of a reductive hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted hydroxyaldehydes. The substituted and unsubstituted hydroxyaldehydes produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted hydroxyaldehydes as principal product(s) of reaction.

Processes for producing hydroxyaldehydes

This invention relates in part to processes for producing one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanals, which comprise subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted hydroxyaldehydes. The substituted and unsubstituted hydroxyaldehydes produced by the processes of this invention can undergo further reaction(s) to afford desired derivatives thereof, e.g., epsilon caprolactone. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted hydroxyaldehydes as principal product(s) of reaction.

A process for preparing cyclic ethers which comprises contacting a carboxylated ether with a mixed metal oxide catalyst under conditions effective to produce the cyclic ether.

Processes for the preparation of cyclic ethers

A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.

Processes for the preparation of ethers

A decarboxylation process which comprises contacting a carboxylated compound with a metal oxide catalyst under conditions effective to decarboxylate the carboxylated compound.

Decarboxylation processes using mixed metal oxide catalysts

.beta.-Hydroxyamines can be converted to the corresponding aziridines by contacting the amines with a molecular sieve, which has incorporated therein at least one alkali metal or alkaline metal, the preferred metal being cesium. Molecular sieves useful in the reaction include aluminosilicates, aluminophosphates and silicoaluminophosphates. The process is especially useful for the conversion of monoethanolamine to ethylenimine.

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Cross Lanes, WV, United States of America

Kurt Damar Olson