Process for the preparation of n-phosphono-methylglycine and...

C - Chemistry – Metallurgy – 07 – F

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C07F 9/38 (2006.01)

Patent

CA 2536327

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.

L'invention concerne des N-phosphonométhylamines que l'on produit en faisant réagir un substrat amine avec un acide halométhylphosphonique ou un sel de celui-ci, un acide hydroxyméthylphosphonique ou un sel de celui-ci, ou un dimère, trimère ou oligomère d'acide hydroxyméthylphosphonique auto-ester déshydraté. On peut notamment préparer suivant ce procédé des acides N-phosphonométhylaminocarboxyliques, par exemple glyphosate, des N-phosphonométhylaminoalcanols par exemple l'acide hydroxyéthylaminométhylphosphonique, et des acides N-acylaminométhylphosphoniques, par exemple l'acide N-carbamylaminométhylphosphonique. On réalise certaines réactions avec un sensible excédent de réactif amine afin d'entraîner la transformation tout en évitant la formation excessive de sous-produits bis(N-phosphonométhyle) amine. Dans d'autres réactions, on utilise un substrat amine secondaire (par exemple l'acide iminodiacétique) et on peut les réaliser selon des rapports équimolaires d'acide halométhylaminométhylphosphonique ou d'acide hydroxyaminométhylphosphonique sur un réactif amine secondaire sans formation importante de sous-produits bis(N-phosphonométhyle). L'invention concerne en outre la préparation de dimères, trimères et oligomères auto-ester d'acide hydroxyméthylphosphonique par déshydratation azéotropique.

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