Monsanto Company

Terry M Balthazor

John P Chupp

William H Miller

Mitchell J Pulwer

James P Coleman

Samuel J Tremont

Gerhard H Alt

Richard D Goodin

Audrey Y Ku

There is disclosed a process for producing the alkali metal salts of N-phosphonomethylglycine which comprises heating to an elevated temperature an aqueous solution of a di- or tri-alkali metal salt of N-alkyl-N-phosphonomethylglycine. The N-alkyl substituent contains at least one hydrogen on the beta carbon atom.

Thermal dealkylation of N-alkyl N-phosphonomethylglycine

Ortho-alkylanilines are prepared by catalytic hydrodesulfurization of ortho-aminobenzyl sulfides using a cobalt-molybdenum oxide catalyst. For example, 2-methyl-6-trifluoromethylaniline is prepared by catalytic hydrodesulfurization of 3-trifluoromethyl-2-aminobenzyl sulfides. The substituted anilines prepared by the method of this invention are useful as intermediates in the synthesis of compounds shown to have herbicidal activity.

Catalytic hydrodesulfurization of ortho-aminobenzylsulfides

Amino acids can be produced from suitable tertiary and secondary amines by dealkylation using an alkali metal hydroxide.

Amine dealkylation process

A process for the preparation of a glyphosate product. An .alpha.-substituted N-phosphonomethylamino diacetic acid substrate is contacted in an aqueous medium with molecular oxygen in the presence of a catalyst for the oxidative cleavage of a substituent from the imino nitrogen of the substrate. Cleavage produces a glyphosate product, carbon dioxide, a higher aldehyde, or ketone. Novel intermediates and methods of preparation thereof are also disclosed.

Process for the preparation of a glyphosate product

.alpha.-Substituted N-phosphonomethyliminodiacetic acid

This invention pertains to processes for the preparation of nuclear substituted benzylic halides such as ortho-amino benzyl chlorides by reaction of substituted benzyl sulfoxides with nonoxidizing acid halides.

Preparation of substituted benzylic halides

This invention relates to a process for the preparation of 2-(methylthiomethyl)-6-(trifluoromethyl) aniline, [MTA], from ortho-aminobenzotrifluoride, (OABT), employing a single solvent transformation via a sulfilimine intermediate. A sulfilimine hydrochloride salt is prepared by the oxidative addition of dimethyl sulfide to OABT in the presence of N-chlorosuccinimide. Neutralization of the sulfilimine hydrochloride salt with aqueous sodium hydroxide followed by phase separation results in an organic phase containing free sulfilimine and an aqueous phase generally containing succinimide and/or sodium succinimide. In a preferred embodiment the phase separation is performed in such a manner to leave a catalytic amount of succinimide in the organic phase. The free sulfilimine catalytically rearranges at moderate temperatures in the presence of this succinimide catalyst to form MTA. The aqueous phase separated after neutralization of the sulfilimine hydrochloride salt contains succinimide and/or sodium succinimide which may be converted by the action of chlorine to N-chlorosuccinimide which in turn may be recycled to the first step in the process.

Preparation of 2-(methylthiomethyl)-6-(trifluoromethyl)aniline from

The disclosure herein relates to substituted 2-alkylsulfonylalkyl nitrobenzenes and a process for the preparation thereof. The compounds herein are useful as intermediates in the preparation of certain substituted anilines used as reactants in the preparation of 2-haloacetanilide herbicides.

Substituted 2-alkylsulfonylalkyl nitrobenzenes and process for their

Various substituted ortho-alkyl anilines are prepared by electrolytic desulfurization of various benzyl sulfides, sulfoxides and sulfones, e.g. 2-methyl-6-trifluoromethylaniline is prepared from 2-amino-3-trifluoromethylbenzyl sulfides, sulfoxides and sulfones. The processes are conducted in concentrated aqueous quaternary ammonium hydroxide, as well as in aprotic media. The substituted anilines obtained are useful as intermediates for herbicide compounds.

Growing community of inventors

University City, MO, United States of America

Terry M Balthazor