Dow Global Technolgoies LLC

Rohm and Haas Company

Dow Agrosciences LLC

The Dow Chemical Company

University of Minnesota

Daniel A Hickman

Kirk Walton Limbach

Mark E Jones

Dmitry A Krapchetov

Timothy Charles Frank

Erich J Molitor

Victor J Sussman

Shawn D Feist

Jeffrey A Herron

Abraham D Schuitman

Patrick H Au-Yeung

Terrence McCabe

Bruce S Holden

Michael Lee Trippeer

Jason Lee Bronkema

Mukund R Patel

Robin K Johnston

Michael M Olken

Stacie L Santhany

D Wayne Blaylock

David Craig Molzahn

Barry B Fish

Albert Edward Schweizer

Christopher D Frick

Robert J Gulotty, Jr

John P Henley

Wen-Sheng Lee

Daniel J Reed

Wen Sheng Lee

Lee E Walko

William D Clarke

Kenric A Marshall

Daniel J Arriola

Michael Leo Tulchinsky

James Elder

Lanny D Schmidt

James William Ringer

Alexey Kirilin

Andrew T Heitsch

William G Worley

Dmitri A Kraptchetov

David Jean

Kurt D Olson

Ramzy M Shayib

Patrick Ho Sing Au-Yeung

Kurt W Olson

Todd William Toyzan

Gerald W Dare

James E Elder

Erich Molitor

Ramzy Shayib

Gerald Dare

Todd Toyzan

A method for preparing methyl methacrylate from methacrolein and methanol. The process comprises contacting in a reactor a mixture comprising methacrolein, methanol and oxygen with a heterogeneous catalyst comprising a support and a noble metal, wherein said catalyst has an average diameter of at least 200 microns, liquid and gaseous reactants flow downward in the reactor and wherein the continuous phase in the reactor is a gas which has no more than 7.5 mol % oxygen at reactor inlets.

Method for production of methyl methacrylate by oxidative esterification using a heterogeneous catalyst

A method for preparing methyl methacrylate from methacrolein and methanol. The method comprises contacting a mixture comprising methacrolein, methanol and oxygen with a heterogeneous catalyst comprising a support and a noble metal, wherein oxygen concentration at a reactor outlet is from 1 to 7.5 mol % and wherein pH at a reactor outlet is no greater than 7.5.

A method for preparing methyl methacrylate from methacrolein and methanol. The method comprises contacting a mixture comprising methacrolein, methanol and oxygen with a heterogeneous catalyst comprising a support and a noble metal, wherein said catalyst has an average diameter of at least 200 microns and at least 90 wt % of the noble metal is in the outer 70% of catalyst volume, and wherein oxygen concentration at a reactor outlet is from 0.5 to 7.5 mol %.

A method for preparing methyl methacrylate from methacrolein and methanol. The method comprises contacting a mixture comprising methacrolein, methanol and oxygen with a heterogeneous catalyst comprising a support and a noble metal, wherein said catalyst has an average diameter of at least 200 microns and average concentration of methacrolein is at least 15 wt %.

A method for preparing methyl methacrylate from methacrolein and methanol; said method comprising contacting in a reactor a mixture comprising methacrolein, methanol and oxygen with a heterogeneous catalyst comprising a support and a noble metal, wherein pH at the reactor outlet is from 3 to 6.7.

A method for preparing methyl methacrylate from methacrolein and methanol. The method comprises contacting in a reactor a mixture comprising methacrolein, methanol and oxygen with a heterogeneous catalyst comprising a support and a noble metal, wherein said catalyst has an average diameter of at least 200 microns, wherein oxygen concentration at a reactor outlet is from 0.5 to 7.5 mol % and wherein the reactor comprises a partition with the catalyst bed on a first side of the partition and with flow through the catalyst bed in a first direction and flow on a second side of the partition in an opposite direction.

A method for preparing methyl methacrylate from methacrolein and methanol. The method comprises contacting in a tubular reactor having at least four zones a mixture comprising methacrolein, methanol, oxygen and a base with a catalyst bed of heterogeneous catalyst comprising a support and a noble metal, wherein reaction zones comprising catalyst beds alternate with mixing zones not comprising catalyst beds.

A process for converting tertiary halogenated hydrocarbons in a tertiary halogenated hydrocarbon-containing stream to a corresponding unhalogenated or less-halogenated unsaturated hydrocarbon product with the release of hydrogen halide involves contacting the tertiary halogenated hydrocarbon with a sorbent-type dehydrohalogenation catalyst in a reaction zone and optionally passing a stripping gas through the reaction zone to remove vapor phase reaction products from the reaction zone. A process for removing a tertiary chlorinated hydrocarbon impurity from 1,3-dichloro-1-propene involves contacting a mixture containing the 1,3-dichloro-1-propene and the tertiary chlorinated hydrocarbon impurity with a dehydrochlorination catalyst effective to catalyze a conversion of the tertiary chlorinated hydrocarbon impurity to a corresponding unchlorinated or less-chlorinated unsaturated hydrocarbon and hydrogen chloride and distilling the 1,3-dichloro-1-propene to produce a purified cis-1,3-dichloro-1-propene fraction and a purified trans-1,3-dichloro-1-propene fraction.

Selective dehydrohalogenation of tertiary halogenated hydrocarbons and removal of tertiary halogenated hydrocarbon impurities from a halogenated hydrocarbon product

The instant invention provides cycloaliphatic diamines and a method of making the same. The cycloaliphatic diamines according to the instant invention comprise the reaction product of one or more cycloaliphatic cyanoaldehydes selected from the group consisting of 1,3-cyanocyclohexane carboxaldehyde, 1,4-cyanocyclohexane carboxaldehyde, mixtures thereof, and combinations thereof, hydrogen, and ammonia fed into a continuous reductive amination reactor system; wherein the one or more cycloaliphatic cyanoaldehydes, hydrogen, and ammonia are contacted with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80&#xb0; C. to about 160&#xb0; C. and a pressure in the range of from 700 to 3500 psig; and wherein one or more cycloaliphatic diamines are formed; and wherein said one or more cycloaliphatic diamines are selected from the group consisting of 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, combinations thereof, and mixtures thereof.

Cycloaliphatic diamines and method of making the same

The instant invention provides a process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities, and aliphatic diamines obtained via such a process. The process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities according to the instant invention comprises the steps of: (1) feeding one or more cycloaliphatic cyanoaldehydes, hydrogen, ammonia, and optionally one or more solvents into a continuous reductive amination reactor system; (2) contacting said one or more cycloaliphatic cyanoaldehydes, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 80&#xb0; C. to about 160&#xb0; C. and a pressure in the range of from 700 to 3500 psig; (3) thereby forming a product mixture comprising one or more cycloaliphatic diamines, optionally one or more bicyclic by-products, optionally one or more cycloaliphatic aminonitriles, optionally one or more cycloaliphatic aminoalcohols, optionally one or more oligomeric by-products, ammonia, water, hydrogen, and optionally one or more solvents; (4) removing said product mixture from the reactor system; (5) removing at least a portion of said ammonia, said hydrogen, or mixture thereof from said product mixture via distillation; (6) removing at least a portion of said water and said one or more optional solvents via distillation; (7) removing at least a portion of one or more optional bicyclic by-products via distillation; (8) removing one or more optional cycloaliphatic aminonitriles, one or more optional cycloaliphatic aminoalcohols, one or more optional oligomeric by-products via distillation; and (9) thereby separating said one or more cycloaliphatic diamines from said product mixture.

Process for separating one or more aliphatic diamines from reductive amination reaction solvents and impurities

A process for converting a tertiary halogenated hydrocarbons in a tertiary halogenated hydrocarbon-containing stream to a corresponding unhalogenated or less-halogenated unsaturated hydrocarbon product with the release of hydrogen halide involves contacting the tertiary halogenated hydrocarbon with a sorbent-type dehydrohalogenation catalyst in a reaction zone and optionally passing a stripping gas through the reaction zone to remove vapor phase reaction products from the reaction zone. A process for removing a tertiary chlorinated hydrocarbon impurity from 1,3-dichloro-1-propene involves contacting a mixture containing the 1,3-dichloro-1-propene and the tertiary chlorinated hydrocarbon impurity with a dehydrochlorination catalyst effective to catalyze a conversion of the tertiary chlorinated hydrocarbon impurity to a corresponding unchlorinated or less-chlorinated unsaturated hydrocarbon and hydrogen chloride and distilling the 1,3-dichloro-1-propene to produce a purified cis-1,3-dichloro-1-propene fraction and a purified trans-1,3-dichloro-1-propene fraction.

A process for conversion of aliphatic bicyclic amines to aliphatic diamines including contacting one or more bicyclic amines selected from the group consisting of 3-azabicyclo[3.3.1]nonane and azabicyclo[3.3.1]non-2-ene with ammonia and hydrogen, and alcohols in the presence of heterogeneous metal based catalyst systems, a metal selected from the group consisting of Co, Ni, Ru, Fe, Cu, Re, Pd, and their oxides at a temperature from 140&#xb0; C. to 200&#xb0; C. and a pressure from 1540 to 1735 psig for at least one hour reactor systems; forming a product mixture comprising aliphatic diamine(s), bicyclic amine(s), ammonia, hydrogen, and alcohol(s); removing said product mixture from the reactor system; removing at least some of the ammonia, hydrogen, water, alcohols, bicyclic amines from said product mixture; thereby separating the aliphatic diamines from said product mixture.

Process for the conversion of aliphatic cyclic amines to aliphatic diamines

A process for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines comprising (1) providing a mixture of 1,3-cyanocyclohexane carboxaldehyde and/or 1,4-cyanocyclohexane carboxaldehyde; (2) contacting said mixture with a metal carbonate based solid bed or a weak base anion exchange resin bed at a temperature from 15 to 40 &#xb0; C. for a period of at least 1 minute; (3) thereby treating said mixture, wherein said treated mixture has a pH in the range of 6 to 9; (4) feeding said treated mixture, hydrogen, and ammonia into a continuous reductive amination reactor system; (6) contacting said treated mixture, hydrogen, and ammonia with each other in the presence of one or more heterogeneous metal based catalyst systems at a temperature from 80 &#xb0; C. to 160 &#xb0; C. and a pressure from 700 to 3500 psig; (7) thereby producing one or more cycloaliphatic diamines is provided.

Process for reductive amination of aliphatic cyanoaldehydes to aliphatic diamines

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Midland, MI, United States of America

Daniel A Hickman