Monsanto Technology LLC

Monsanto Company

Howard C Berk

Juan Pedro Arhancet

David A Morgenstern

James C Peterson

William L Moench, Jr

John Joseph Parlow

Bruno De Kort

Junqiu Yang

Amy E Stroman

Thaddeus S Franczyk, Ii

James W Kassebaum

Robert B Weisenfeld

William L Moench

The present invention generally relates to processes for purification, recovery, and conversion of chlorophenol salts (e.g., 2,5-dichlorophenol and salts thereof). In various aspects, the present invention is related to removing one or more impurities from chlorophenol salt-containing process streams and/or recovering chlorophenol salts from process streams for use of the recovered chlorophenol elsewhere in an integrated process. Process streams that may be treated in accordance with the present invention include those incorporating one or more chlorophenol salts in a feed mixture and also those where one or more chlorophenol salts are present in a product or by-product stream of an integrated process. For example, conversion processes of the present invention are suitable as one piece of an integrated process for producing 3,6-dichloro-2-methoxybenzoic acid (dicamba) or a salt or ester thereof or a process for producing 2,4-dichlorophenoxyacetic acid (2,4-D) or a salt or ester thereof. The present invention further relates to processes for preparation, purification, and recovery of intermediates formed in integrated processes utilizing chlorophenol salts such as 2,5-dichlorophenol as starting material, including the intermediate 3,6-dichlorosalicylic acid (3,6-DCSA) formed during preparation of dicamba from 2,5-dichlorophenol.

Processes for purification, recovery, and conversion of chlorophenol salts and preparation and recovery of products prepared therefrom

This invention is directed a process for preparation of a carboxylic acid salt by dehydrogenation of a primary alcohol. The invention is also directed to a catalyst for dehydrogenating primary alcohols. In one embodiment, for example, the catalyst comprises a metal support (preferably a metal sponge support) having a copper-containing coating at the surface thereof. In another embodiment, the catalyst comprises a metal selected from the group consisting of zinc, cobalt, iron, tin and combinations thereof having a copper-containing coating at the surface thereof.

Process for preparation of a carboxylic acid salt by dehydrogenation of a primary alcohol

This invention is directed to catalysts for dehydrogenating primary alcohols. Catalysts comprising a metal support comprising (a) from about 2% to about 30% by weight copper, and (b) at least about 50% by weight non-copper metal selected from the group consisting of nickel, zinc, tin, cobalt, iron and combinations thereof; and a copper-containing coating are described.

Catalyst for dehydrogenating primary alcohols

This invention is directed to a process for making a salt of a carboxylic acid. The process comprises contacting a catalyst with an alkaline mixture comprising a primary alcohol. In one embodiment, for example, the catalyst comprises a metal support (preferably a metal sponge support) having a copper-containing active phase at the surface thereof. The support is resistant to deformation under the conditions of the dehydrogenation reaction. In another embodiment, the catalyst comprises a metal sponge having a copper-containing active phase at the surface thereof and a supporting structure containing at least 10% non-copper metal. This invention is also directed to copper-containing catalysts which may, for example, be used in the above process. This invention is further directed to processes for making such catalysts.

Process and catalyst for dehydrogenating primary alcohols to make carboxylic acid salts

This invention is directed to a process for making an iminodiacetic acid compound from a monoethanolamine substrate having the formula: wherein Ris hydrogen, hydrocarbyl, or substituted hydrocarbyl. The process includes a series of reactions comprising a cyanomethylation, a hydrolysis and a dehydrogenation. In a particular embodiment, the iminodiacetic acid produced is disodium iminodiacetic acid and the monoethanolamine substrate used is 2-aminoethanol.

Process for making iminodiacetic acid compounds from monoethanolamine substrates

This invention is directed to a process for dehydrogenating primary alcohols to make salts of carboxylic acids. The process comprises contacting a catalyst, preferably a metal support coated with copper or silver, with an alkaline mixture comprising a primary alcohol. The invention further provides for novel copper-containing and silver-containing catalysts which may be used, for example, in the above process as well as processes for making such catalysts.

Catalyst for dehydrogenating primary alcohols to make carboxylic acid salts

Disclosed are storage-stable aqueous concentrate formulations of pesticides or plant growth modifying agents containing sufficient amounts of an alkoxylated alkylamine surfactant to insure a high degree of pesticidal or plant growth modifying efficacy, wherein irritancy to eyes resulting from the presence of said surfactant is reduced by the presence of an effective amount of a C.sub.6-22 saturated or unsaturated alkyl monocarboxylic or dicarboxylic acid or mixture of such acids.

Aqueous concentrate formulations having reduced eye irritancy

A herbicidal composition is provided which is substantially non-irritant to the eyes and which comprises a stable aqueous concentrate solution of one or more agriculturally acceptable salts-of N-phosphonomethylglycine and a surfactant represented by the formula ##STR1## wherein R is an alkyl group having from about 6 to about 14 carbon atoms, R.sup.1 is ethyl, propyl, or a mixture of ethyl and propyl, the sum of n and m is between about 5 and about 50, R.sup.2 is an alkyl group with 1-4 carbon atoms, X is an agriculturally acceptable anion, and the weight ratio of surfactant to N-phosphonomethylglycine (expressed as the acid equivalent) is between about 1:5 and about 5:1.

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St. Louis, MO, United States of America

Howard C Berk