Monsanto Technology LLC

Mark A Leiber

Kam-To Wan

Jerry R Ebner

Peter E Rogers

Anthony Woods

William A Scholle

Jingyue Liu

Juan Pedro Arhancet

Jerald D Heise

Michael Rogers

Eduardo Aurelio Casanova

Eric A Haupfear

Henry H Chien

Amy L Jorgenson

William B Hooper

Jingye Liu

Karen A Wittler, Legal Representative

This invention relates to the field of heterogeneous catalysis, and more particularly to oxidation catalysts including carbon supports having deposited thereon a noble metal and one or more optional promoters and to methods for their preparation. The invention further relates to the field of heterogeneous catalytic oxidation reactions, including the preparation of secondary amines by the catalytic oxidation of tertiary amines, such as the oxidation of an N-(phosphonomethyl)iminodiacetic acid to produce an N-(phosphonomethyl)glycine product.

Oxidation catalyst and its use for catalyzing 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., '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

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, a process for making of an improved catalyst comprising such a supplemental promoter, and an improved catalyst comprising such a supplemental promoter.

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

This invention relates to the use of a promoter in conjunction with a noble-metal-containing catalyst comprising a carbon support in catalyzing liquid phase oxidation reactions. In a particularly preferred embodiment, the catalyst comprises a carbon support having a noble metal and tellurium at a surface of the carbon support and is used 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.

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 generally relates to liquid phase oxidation processes for making N-(phosphonomethyl)glycine (also known in the agricultural chemical industry as glyphosate) and related compounds. This invention, for example, particularly relates to processes wherein an N-(phosphonomethyl)iminodiacetic acid (NPMIDA) substrate (i.e., N-(phosphonomethyl)iminodiacetic acid, a salt of N-(phosphonomethyl)iminodiacetic acid, or an ester of N-(phosphonomethyl)iminodiacetic acid) is continuously oxidized to form an N-(phosphonomethyl)glycine product (i.e., N-(phosphonomethyl)glycine, a salt of N-(phosphonomethyl)glycine, or an ester of N-(phosphonomethyl)glycine). This invention also, for example, particularly relates to processes wherein an N-(phosphonomethyl)iminodiacetic acid substrate is oxidized to form an N-(phosphonomethyl)glycine product, which, in turn, is crystallized (at least in part) in an adiabatic crystallizer.

Reaction systems for making N-(phosphonomethyl) glycine compounds

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

An improved catalyst comprising a noble metal and tellurium at the surface of a carbon support is provided. Also provided are novel methods for preparing such catalysts and novel processes for the use of such catalysts in liquid phase oxidation reactions, particularly the oxidation of N-(phosphonomethyl)iminodiacetic acid or a salt thereof.

Use of tellurium in carbon-supported, noble metal-containing catalysts for liquid phase oxidation reactions

A treatment for de-oxygenating a noble metal on carbon catalyst used in liquid phase oxidation reactions which includes exposing the catalyst to a non-oxidizing environment. The de-oxygenation treatment improves catalyst performance and is particularly suited for noble metal on carbon catalysts used to catalyze the oxidative cleavage of a carboxymethyl substituent from an N-(phosphonomethyl)iminodiacetic acid substrate in an aqueous reaction mixture using an oxygen-containing gas to produce an N-(phosphonomethyl)glycine product. In one embodiment, the catalyst is exposed to a non-oxidizing environment by introducing a non-oxidizing gas and/or reducing gas into a slurry comprising the catalyst in contact with a liquid medium.

De-oxygenation treatment for noble metal on carbon catalysts used 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.

Growing community of inventors

St. Peters, MO, United States of America

Mark A Leiber