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US4237065A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of N-phosphonomethyl glycine

Assignee: Biological Chemical Activities Patents (Bcap)
•
Filing: 1979-10-15
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Granted: 1980-12-02
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Expires: 1999-10-15
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Abstract

Abstract N-phosphonomethyl glycine is prepared starting from glycine, formaldehyde and a tertiary base in alcoholic solution. After completion of the reaction, a dialkyl phosphite is added. The reaction product is hydrolyzed, and acidification yields the desired product in good purity.

Inventors

  • 👤 Rodolphe Ehrat

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 01:33
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3808; C07F9/3813

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 55 words
A process for the preparation of N-phosphonomethyl glycine, wherein glycine is dissolved in an alcoholic solution of formaldehyde and a tertiary base, to the so obtained completed solution a dialkyl phosphite is added, the reaction mixture is subjected to an alkaline hydrolysis followed by an acidification whereupon the desired N-phosphonomethyl glycine is obtained by precipitation.
Claim 2
Dependent Claim 55 words
A process for the preparation of N-phosphonomethyl glycine, wherein glycine is dissolved in an alcoholic solution of formaldehyde and a tertiary base, to the so obtained completed solution a dialkyl phosphite is added, the reaction mixture is subjected to an alkaline hydrolysis followed by an acidification whereupon the desired N-phosphonomethyl glycine is obtained by precipitation.
Claim 3
Dependent Claim 90 words
The process of claim 1 comprising the following steps: Dissolving formaldehyde in an alcohol with heating and adding a small quantity of a tertiary base to effect the depolymerization of the paraformaldehyde; adding glycine and a greater amount of said tertiary base; adding after completion of the solution, a dialkyl phosphite; reacting the mixture in the heat and saponifying the formed ester by means of an aqueous NaOH solution while removing said alcohol and said tertiary base; and acidifying the obtained alkaline solution in order to precipitate said N-phosphonomethyl glycine.
Claim 4
Dependent Claim 24 words
The process of claim 1 or 2 wherein said alcohol is methanol, said formaldehyde is trioxymethylene or paraformaldehyde, and said tertiary base is triethylamine.
Claim 5
Dependent Claim 24 words
The process of claim 1 or 2, wherein the acidification of the final alkaline solution is effected to a pH of less than 2.
Claim 6
Dependent Claim 41 words
The process of claim 3 wherein a solution of triethylamine in methanol is obtained by the recuperation and the recycling of a distillate at a temperature of not more than 70° C. of said aqueous alkaline saponification solution of the process.
Claim 7
Dependent Claim 110 words
The process of claim 1 or 2, wherein the molar ratio of triethylamine to glycine is not less than 1, the ratio of formaldehyde; to glycine is comprised in the range between 1 and 2 and the ratio of said phosphite to said glycine is comprised in the range between 0.4 and 2, the amount of solvent is between 150 and 500 ml per mol of glycine, the amount of NaOH to hydrolyze the ester is comprised between 3 and 4 mols per mol of said phosphite used and the amount of acid necessary to effect the acidification of the saponified solution corresponds to the molar amount of said NaOH.
Claim 8
Dependent Claim 17 words
The process of claim 1 or 2 wherein hydroxymethylphosphonic acid is reclaimed as a secondary reaction product.
Claim 9
Dependent Claim 31 words
The process of claim 7 wherein the reclaiming of said hydroxymethylphosphonic acid is carried out in the form of an insoluble salt before or after the separation of said N-phosphonomethyl glycine.
Claim 10
Dependent Claim 33 words
The process of claim 6 wherein the ratio of formaldehyde to glycine is between 1.3 and 1.6, the ratio of phosphite to glycine is between 0.6 and 1.6 and the solvent is methanol.
Claim 11
Dependent Claim 12 words
The process of claim 8 wherein the insoluble salt is calcium salt.

References Cited (Backward Citations)

US2635112A Cited
US2847442A Cited
US3288846A Cited
US3549728A Cited
US3956370A Cited
DE2741504A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-12-02 1984-06-02 1984-12-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-12-02 1988-06-02 1988-12-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-12-02 1992-06-02 1992-12-02 $7700.00 Window Closed / Lapsed

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