70393-85-0

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 113, p. 3371, 1991 DOI: 10.1021/ja00009a023

InChI:InChI=1/3C3H8NO5P.2Na/c3*5-3(6)1-4-2-10(7,8)9;;/h3*4H,1-2H2,(H,5,6)(H2,7,8,9);;/q;;;2*+1/p-6

Upstream product

• 1071-83-6 N-(phosphonemethyl)glycine 
• 110-90-7 hexahydro-1,3,5-triazine 
• 60672-94-8 1,3,5-tri-(ethoxycarbonylmethyl)hexahydro-1,3,5-triazine 
• 64140-94-9 N,N’-bis(phosphonomethyl)-2,5-diketopiperazine 
• 2617-47-2 hydroxymethylphosphonic acid 
• 6000-44-8 sodium glycinate 
• 2565-58-4 chloromethylphosphonic acid 
• 142-73-4 iminodiacetic acid 

Relevant academic research and scientific papers

METHOD FOR THE SYNTHESIS OF N-(PHOSPHONOMETHYL)GLYCINE

The present invention is related to a method for the synthesis of N- (phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters, or its phosphonate ester salts, which includes the steps of: ? a) forming, in the presence an acid catalyst, a reaction mixture comprising 2,5- diketopiperazine, formaldehyde and a compound comprising one or more P-0-P anhydride moieties, said moieties having one P atom at the oxidation state (+ III) and the other P atom at the oxidation state (+III) or (+V), to form Ν,Ν'- bisphosphonomethyl-2,5-diketopiperazine, its mono- to tetra phosphonate esters, the dehydrated forms of Ν,Ν'- bisphosphonomethyl-2,5-diketopiperazine and the phosphonate esters of its dehydrated forms; ? b) hydrolysing said N,N'-bisphosphonomethyl-2,5-diketopiperazine, its dehydrated forms or their phosphonate esters to obtain N- (phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters and its phosphonate ester salts.

Process for the preparation of N-phosphonomethylglycine and derivatives thereof

N-phosphonomethylamines are produced by reaction of an amine substrate with a halomethylphosphonic acid or salt thereof, a hydroxymethylphosphonic acid or salt thereof, or a dehydrated self-ester dimer, trimer or oligomer of hydroxymethylphosphonic acid. Among the products that may be prepared according to the process are N-phosphonomethylaminocarboxylic acids such as (e.g.) glyphosate, N-phosphonomethylaminoalkanols such as (e.g.) hydroxyethlaminomethylphosphonic acid, and N-acylaminomethylphosphonic acids such as (e.g.) N-carbamylaminomethylphosphonic acid. Certain reactions are conducted with a substantial excess of amine reactant in order to drive the conversion while avoiding excessive formation of bis(N-phosphonomethyl)amine by-products. Other reactions use a secondary amine substrate (such as iminodiacetic acid) and can be conducted at substantial equimolar ratios of halomethylaminomethylphosphonic acid or hydroxyaminomethylphosphonic acid to secondary amine reactant without significant formation of bis(phosphonomethyl)amine by-products. Further disclosed is a process for the preparation of hydroxymethylphosphonic acid self-ester dimers, trimers and oligomers by azeotropic dehydration.

Process for the preparation of glyphosate and glyphosate derivatives

A process for preparing glyphosate and other secondary amines of related structure in which a precursor primary amine such as aminomethylphosphonic acid is condensed with glyoxylic acid, or a related aldehyde compound, and the condensation product reduced without isolation to produce the desired product.

Method for preparation of N-phosphonomethylglycine or salts

A method for the production of N-phosphonomethylglycine and soluble salts thereof is disclosed in which glycinemethylenephosphinic acid or its soluble salts are reacted with an excess of an alkali or alkaline earth base for a period of time and at a sufficient temperature to cause oxidation of the glycinemethylenephosphinic acid or its soluble salts thereof to N-phosphonomethylglycine salts, from which N-phosphonomethylglycine may be obtained by acidification. The N-phosphonomethyleglycine or its soluble salts, are used as herbicides.

Method for preparation of N-phosphonomethylglycine

Disclosed is a method for the preparation of N-phosphonomethylglycine which comprises the steps of (1) reacting 1,3,5-tris(alkoxy- or aryloxy-substituted carbonylmethyl) hexahydro-s-triazine, with a substituted phosphorus compound having the formula PXYZ wherein X is a halogen, Y and Z are independently selected from the group consisting of halogen, alkoxy having from 1 to 10 carbon atoms, and aryloxy, in the presence of a protic acid and a low molecular weight carboxylic acid; (2) heating said reactants to a temperature ranging from about 10° to about 25° C. for a sufficient period of time to cause the formation of an N-phosphonomethylglycine ester,; and (3) hydrolyzing said phosphonomethylglycine ester to N-phosphonomethylglycine.

Method for preparation of N-phosphonomethylglycine

Disclosed is a method for the preparation of N-phosphonomethylglycine which comprises the steps of (a) reacting 1,3,5-tri-(substituted methyl) hexahydro-s-triazine, a compound of the formula STR1 wherein R, R1 and R2 are the same or different and are selected from the group consisting of cyano, alkoxycarbonyl wherein the alkyl group ranges from 2 to 18 carbon atoms, and aryloxycarbonyl wherein the aryl group ranges from 6 to 12 carbon atoms, with a substituted phosphorus compound having the formula PXYZ wherein X is a halogen, Y and Z are each independently selected from the group consisting of halogen, alkoxy having from 1 to 10 carbon atoms and aryloxy, in the presence of a low molecular weight carboxylic acid solvent and a protic acid; (b) treating the reaction mixture with water; (c) removing said solvent and hydrolyzing the residue with aqueous alkali to generate a salt of N-phosphonomethylglycine; and (d) neutralizing said salt with an acid to produce the end product, N-phosphonomethylglycine.

Increasing carbohydrate deposition in plants with N-phosphono-methylglycine and derivatives thereof

N-phosphonomethylglycine and derivatives thereof useful to increase the carbohydrate deposition in plants.