Monsanto Company

Monsanto Technology LLC

Pharmacia Corporation

Thaddeus S Franczyk, Ii

Jerry R Ebner

Juan Pedro Arhancet

David A Morgenstern

Michael K Stern

Michael D Rogers

Howard C Berk

James C Peterson

Robert B Weisenfeld

William L Moench, Jr

Todd J Johnson

Amy L Jorgenson

Donald W Hansen, Jr

Alan E Moormann

Mahima Trivedi

Ronald Keith Webber

Alok K Awasthi

Jeffrey S Snyder

William L Moench

An improved process for the manufacture of formylphosphonic acid derivatives is reported. An aminomethylphosphonic acid substrate is contacted with a reagent selected from the group consisting of water, an alcohol, a phenol compound, and mixtures thereof and an oxidizing gas in the presence of a catalyst to form a reaction product mixture containing a formylphosphonic acid derivative and the conditions under which said contacting is carried out are controlled so that no more than 50% of the formylphosphonic acid derivative formed in the reaction product mixture is consumed by reaction with the reagent.

Method for preparing formylphosphonic acid

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

A process for oxidizing a hydroxymethylphosphonic acid compound to produce a formylphosphonic acid compound is described. The oxidation reaction is carried out in the presence of an oxidant and a catalyst. For example, hydroxymethylphosphonic acid (HMPA) is oxidized by oxygen or hydrogen peroxide in the presence of a copper-containing catalyst to give formylphosphonic acid (FPA). Formylphosphonic acid can then be reacted with glycine to produce a condensation product which, upon hydrogenation, yields glyphosate. Glyphosate can be incorporated into various formulations for use as a herbicide. In addition to glycine, formylphosphonic acid can also be reacted with ammonia, ethanolamine, or other primary amines to form a precursor compound, which can be converted to glyphosate.

Method of making phosphorus-containing compounds and products thereof

The present invention provides a new and useful improvement in the process to manufacture a carboxylic acid salt, particularly an amino carboxylic acid salt, from a primary alcohol, particularly a primary aminoalcohol. The process of manufacturing amino carboxylic acid salts comprises contacting an aqueous solution of a primary aminoalcohol with a strong hydroxide base selected from the group consisting of an alkali metal hydroxide, an alkaline earth metal hydroxide, an ammonium hydroxide compound including a tetraalkyl ammonium hydroxide, or the like, in the presence of an effective amount of a catalyst. The catalyst comprises one or more of elements selected from the group consisting of copper, cobalt, nickel, and cadmium as well as optionally lesser amounts of chromium, titanium, niobium, tantalum, zirconium, vanadium, molybdenum, manganese, tungsten, cobalt, nickel, or mixtures thereof. The reaction mixture contains less than about 3000 ppm, preferably less than about 500 ppm, more preferably less than about 100 ppm of oxidized copper (Cu and/or Cu ) during the reaction. The concentration of oxidizing agents in the reactants is minimized to prevent formation of oxidized copper from metallic copper catalyst.

Process for the preparation of carboxylic acid salts from primary alcohols

Homoiminopiperidinyl Hexanoic Acid derivatives and pharmaceutically acceptable salts thereof useful in the inhibition of the inducible isoform of nitric oxide synthase are disclosed.

Homoiminopiperidinyl hexanoic acid inhibitors of inducible nitric oxide synthase

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

Formylphosphonic acid derivatives are prepared by the catalytic decomposition of a (phosphonomethyl)amine N-oxide compound to form the formylphosphonic acid derivative and a dephosphonomethylated amine.

Preparation of formylphosphonic acid from tertiary aminomethylphosphonic acid N-oxides

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)

A process for the manufacture of formylphosphonic acid derivatives is reported. An aminomethylphosphonic acid substrate is contacted with a reagent selected from the group consisting of water, an alcohol, a phenol compound, and mixtures thereof and an oxidizing gas in the presence of a catalyst to form a reaction product mixture containing a formylphosphonic acid derivative and the conditions under which said contacting is carried out are controlled so that no more than 50% of the formylphosphonic acid derivative formed in the reaction product mixture is consumed by reaction with the reagent.

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.

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Chesterfield, MO, United States of America

Thaddeus S Franczyk, Ii