Monsanto Company

Monsanto Technology LLC

The Nutrasweet Company

Solutia Incorporated

Huntsman Petrochemical Corporation

Huntsman Specialty Chemicals Corporation

Jerry R Ebner

Kam-To Wan

Mark A Leiber

Peter E Rogers

Anthony Woods

William D McGhee

Indra Prakash

Arnold Hershman

Zhi Guo

Mark D Paster

Loraine M Klein

Thaddeus S Franczyk, Ii

Timothy R Felthouse

John T Gleaves

William J Andrews

Dennis Patrick Riley

Michael K Stern

Brian K Cheng

Robert A Keppel

Jingyue Liu

James P Coleman

Samuel J Tremont

Patrick J Lennon

Tao P Li

Eric A Haupfear

Anthony K Uriarte

Erik D Sall

Michael J Mummey

Michael J Gross

William A Scholle

Serge G Wolfson

Thomas C Kuechler

Denton C Fentress

James William Gambell

Paul Ho Liu

Jingye Liu

Joseph A Schaper

Jayne E Morris

Christopher R Buechler

Philip H Brodsky

Thaddeus S Franczyk

Arnold Herschman

Lorraine M Klein

This invention relates to an improved catalyst, comprising a carbon support having a noble metal at its surface, for use in catalyzing liquid phase oxidation reactions, especially in an acidic oxidative environment and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; a process for the preparation of the improved catalyst; a liquid phase oxidation process using such a catalyst wherein the catalyst exhibits improved resistance to noble metal leaching, particularly in acidic oxidative environments and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; and a liquid phase oxidation process in which N-(phosphonomethyl)iminodiacetic acid (i.e., 'PMIDA') or a salt thereof is oxidized to form N-(phosphonomethyl)glycine (i.e., 'glyphosate') or a salt thereof using such a catalyst wherein the oxidation of the formaldehyde and formic acid by-products into carbon dioxide and water is increased.

Deeply reduced oxidation catalyst and its use in preparing N-(phosphonomethyl) glycine compounds

N-phosphonomethylamines are produced by reaction of an amine substrate with a halomethylphosphonic acid or salt thereof, a hydroxymethylphosphonic acid or salt thereof, or a dehydrated self-ester dimer, trimer or oligomer of hydroxymethylphosphonic acid. Among the products that may be prepared according to the process are N-phosphonomethylaminocarboxylic acids such as (e.g.) glyphosate, N-phosphonomethylaminoalkanols such as (e.g.) hydroxyethlaminomethylphosphonic acid, and N-acylaminomethylphosphonic acids such as (e.g.) N-carbamylaminomethylphosphonic acid. Certain reactions are conducted with a substantial excess of amine reactant in order to drive the conversion while avoiding excessive formation of bis(N-phosphonomethyl)amine by-products. Other reactions use a secondary amine substrate (such as iminodiacetic acid) and can be conducted at substantial equimolar ratios of halomethylaminomethylphosphonic acid or hydroxyaminomethylphosphonic acid to secondary amine reactant without significant formation of bis(phosphonomethyl)amine by-products. Further disclosed is a process for the preparation of hydroxymethylphosphonic acid self-ester dimers, trimers and oligomers by azeotropic dehydration.

Process for the preparation of N-phosphonomethylglycine and derivatives thereof

3,3-Dimethylbutanal is prepared from 3,3-dimethybutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and a mineral acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hydrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converted 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.

Process for the preparation of 3,3-dimethylbutanal

3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and a mineral acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hydrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.

This invention relates to an improved catalyst, comprising a carbon support having a noble metal at its surface, for use in catalyzing liquid phase oxidation reactions, especially in an acidic oxidative environment and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; a process for the preparation of the improved catalyst; a liquid phase oxidation process using such a catalyst wherein the catalyst exhibits improved resistance to noble metal leaching, particularly in acidic oxidative environments and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; and a liquid phase oxidation process in which N-(phosphonomethyl)iminodiacetic acid (i.e., 'PMIDA') or a salt thereof is oxidized to form N-(phosphonomethyl) glycine (i.e., 'glyphosate') or a salt thereof using such a catalyst wherein the oxidation of the formaldehyde and formic acid by-products into carbon dioxide and water is increased.

This invention relates to the use of a supplemental promoter in conjunction with a noble-metal-containing catalyst comprising a carbon support in catalyzing liquid phase oxidation reactions. In a particularly preferred embodiment, a supplemental promoter (most preferably bismuth or tellurium) is used in conjunction with a noble-metal-containing catalyst comprising a carbon support in a liquid phase oxidation process wherein N-(phosphonomethyl) iminodiacetic acid (i.e., 'PMIDA') or a salt thereof is oxidized to form N-(phosphonomethyl)glycine (i.e., 'glyphosate') or a salt thereof. The benefits of such a process include oxidation of the formaldehyde and formic acid by-products, and, consequently, decreased final concentrations of those by-products as well as other undesirable by-products, most notably N-methyl-N-(phosphonomethyl)glycine (i.e., &#x201c;NMG&#x201d;).

Use of a supplemental promoter in conjunction with a carbon-supported noble-metal-containing catalyst in liquid phase oxidation reactions

This invention relates to an improved catalyst, comprising a carbon support having a noble metal at its surface, for use in catalyzing liquid phase oxidation reactions, especially in an acidic oxidative environment and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; a process for the preparation of the improved catalyst; a liquid phase oxidation process using such a catalyst wherein the catalyst exhibits improved resistance to noble metal leaching, particularly in acidic oxidative environments and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; and a liquid phase oxidation process in which N-(phosphonomethyl)iminodiacetic acid (i.e., &ldquo;PMIDA&rdquo;) or a salt thereof is oxidized to form N-(phosphonomethyl)glycine (i.e., &ldquo;glyphosate&rdquo;) or a salt thereof using such a catalyst wherein the oxidation of the formaldehyde and formic acid by-products into carbon dioxide and water is increased.

Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions

Use of a supplemental promoter in conjunction with a carbon-supported, noble-metal containing catalyst in liquid phase oxidation reactions

3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and sulfuric acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hvdrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.

Inert gas additive is utilized in the catalytic oxidation of benzene with nitrous oxide to produce phenol in order to prevent excessive exothermic temperature increases and to render gaseous mixtures throughout the process non-flammable.

Chemical composition and process

An improved process for the manufacture of maleic anhydride by catalytic oxidation of a nonaromatic hydrocarbon having at least four carbon atoms in a straight chain, in which a gas containing oxygen and hydrocarbon is passed through a fixed catalyst bed in a tubular reactor. The activity of the catalyst bed is graded in such manner that the reactor can be operated at an initial (feed gas) hydrocarbon concentration of over 1.5% by volume, an integrated average temperature difference between gas and cooling fluid of at least about 15.degree. C. over that portion of the bed in which the gas temperature exceeds the cooling fluid temperature, and a productivity of at least about 5.0 lbs. maleic anhydride per hour, without the temperature difference between the gas and the cooling fluid exceeding 80.degree. C. at any point in the catalyst bed during the course of the reaction. Preferably, the catalyst activity and the gas permeability of the bed vary in the direction of gas flow so that both the catalyst activity and the pressure drop per unit distance are lower in a critical region, where the combination of temperature and hydrocarbon concentration could otherwise cause the reaction to proceed at an excessive rate, than they are in a region of low temperature and low hydrocarbon concentration. Significant and unexpected improvement in reactor performance is achieved by the combination of a graded catalyst charge and incorporation of a catalyst modifying organophosphorus compound in the hydrocarbon feed.

High productivity process for the production of maleic anhydride

A more reactive thoria catalyst for the production of diaryl ethers from aromatic compounds, a process for making the catalyst and the use of the catalyst is taught. The thoria catalyst has a specified surface area, density and average crystal size.

Thoria catalyst

Carboxylic acid salts are prepared by the dehydrogenation of a primary alcohol in the presence of a catalyst comprising a finely divided anchor metal partially embedded on a support and having at least some of the nonembedded surface coated with an electroless plating of a catalytically active metal. The anchor metal is selected from a group consisting of osmium, iridium, rhodium and mixtures thereof.

Process for preparing carboxylic acid salts and catalysts useful in such

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St. Charles, MO, United States of America

Jerry R Ebner