Monsanto Company

Monsanto Technology LLC

Todd J Johnson

Michael K Stern

Michael D Rogers

Yvette M Fobian

David A Morgenstern

Robert L Cleek

Thaddeus S Franczyk, Ii

Amy L Jorgenson

Jeffrey A Levine

Paul D Drumheller

Theresa A Holland

William H Miller

Bruce Steinhaus

Lars Vincent

Per Antoni

Karin Leontein

Krzysztof R Pietrzak

Novel compounds, N,N&prime;-bis(phosphonomethyl)-N,N&prime;-bis(hydroxycarbonylmethyl)urea and N,N,N&prime;,N&prime;-tetrakis(hydroxycarbonylmethyl)urea, suitable for use in preparing N-acyl aminocarboxylic acids that can be readily converted to N-(phosphonomethyl)glycine are provided. The compounds may be formed by the reaction of bis-(phosophonomethyl)urea or urea respectively with carbon monoxide and formaldehyde in the presence of a carboxymethylation catalyst precursor and solvent.

Method of preparing amino carboxylic acids

A process for the continuous production of N-(phosphonomethyl)glycine is provided. In the process, N-(acetyl)iminodiacetic acid is formed in an amidocarboxymethylation reactor system. The N-(acetyl)iminodiacetic acid product stream is either: (1) reacted with a source of phosphorous and a source of formaldehyde in the presence of an acid to form a phosphonomethylation reaction product stream containing N-(phosphonomethyl)iminodiacetic acid and acetic acid; or (2) deacylated and cyclized to form a 2,5-diketopiperazine, and then reacted with a source of phosphorous and a source of formaldehyde in the presence of an acid to form a phosphonomethylation reaction product stream containing N-(phosphonomethyl)iminodiacetic acid and acetic acid. In either case, the N-(phosphonomethyl)iminodiacetic acid product is recovered and converted to N-(phosphonomethyl)glycine.

Continuous process for the preparation of N-(phosphonomethyl)iminodiacetic acid

Process for the preparation of an N-acyl amino carboxylic acid by means of a carboxymethylation reaction. In this reaction, a reaction mixture is formed which contains a base pair, carbon monoxide, hydrogen and an aldehyde with the base pair comprising a carbamoyl compound and a carboxymethylation catalyst precursor. In a preferred embodiment, the carbamoyl compound and aldehyde are selected to yield an N-acyl amino carboxylic acid which is readily converted to N-(phosphonomethyl)glycine, or a salt or ester thereof.

A process for the production of N-(phosphonomethyl)iminodiacetic acid. N-(acetyl)iminodiacetic acid is formed in a amidocarboxymethylation reactor system, into which a source of each of the following is continuously fed: (1) acetamide or an acetamide derivative, (2) formaldehyde or a formaldehyde generator or derivative, (3) a carbonylation catalyst, (4) carbon monoxide, and optionally (5) hydrogen. In turn, an amidocarboxymethylation reaction product stream, which contains N-(acetyl)iminodiacetic acid and the carbonylation catalyst, is withdrawn from the amidocarboxymethylation reactor system. The carbonylation catalyst is separated from the amidocarboxymethylation reaction product stream to recover the carbonylation catalyst and form a catalyst depleted product stream which contains N-(acetyl)iminodiacetic acid. The separated carbonylation catalyst is returned to the amidocarboxymethylation reactor system, and the N-(acetyl)iminodiacetic acid in the catalyst depleted product stream is either: (1) reacted with a source of phosphorous and a source of formaldehyde in the presence of an acid to form a phosphonomethylation reaction product stream containing N-(phosphonomethyl)iminodiacetic acid and acetic acid; or (2) deacylated and cyclized to form a 2,5-diketopiperazine, and then reacted with a source of phosphorous and a source of formaldehyde in the presence of an acid to form a phosphonomethylation reaction product stream containing N-(phosphonomethyl)iminodiacetic acid and acetic acid. Either way, the N-(phosphonomethyl)iminodiacetic acid is precipitated from the phosphonomethylation reaction product stream in the presence of acetic acid, and the precipitate is recovered to form a filtrate stream.

Continuous process for the preparation of N-(phosphonomethyl)

The invention provides a process for preparing aminophosphonic acids comprising contacting an aminophosphonate ester with a base in the presence of a hydrolysis facilitator selected from the group consisting of CO.sub.2, CS.sub.2 and COS. In one embodiment, the aminophosphonate ester is first prepared by contacting an amine, trialkylphosphite, base and formaldehyde.

Carbon dioxide assisted hydrolysis of aminophosphonates

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Boonville, MO, United States of America

Todd J Johnson