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US4851159A
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Process for the preparation of N- phosphonomethylglycine
Assignee: Monsanto Technology LLC
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Filing: 1988-05-02
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Granted: 1989-07-25
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Expires: 2008-05-02
Abstract
Abstract A process is disclosed for the preparation of N-phosphonomethylglycine which comprises bringing together under reaction conditions glyoxylic acid or a derivative thereof and an N-acylaminomethylphosphonic acid represented by the formula ##STR1## wherein R is selected from the group consisting of alkyl having from one to about 6 carbon atoms, haloalkyl having from one to about six carbon atoms, benzyl and phenyl.
Inventors
- 👤 Jr. Fields
- 👤 Raymond C. Grabiak
- 👤 Sherrol L. Baysdon
- 👤 Peter E. Rogers
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 00:47
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/44; C07F9/3804; C07F9/3808; C07F9/3813
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
67 words
A process for the preparation of N-phosphonomethylglycine which comprises bringing together under reaction conditions a glyoxylic compound which is glyoxylic acid, hydrate, hemiacetal, acetal or alkyl ester thereof and an N-acylaminomethylphosphonic acid represented by the formula ##STR3## wherein R is selected from the group consisting of alkyl having from one to about 6 carbon atoms, haloalkyl having from one to about six carbon atoms, benzyl and phenyl.
Claim 2
Dependent Claim
67 words
A process for the preparation of N-phosphonomethylglycine which comprises bringing together under reaction conditions a glyoxylic compound which is glyoxylic acid, hydrate, hemiacetal, acetal or alkyl ester thereof and an N-acylaminomethylphosphonic acid represented by the formula ##STR3## wherein R is selected from the group consisting of alkyl having from one to about 6 carbon atoms, haloalkyl having from one to about six carbon atoms, benzyl and phenyl.
Claim 3
Dependent Claim
19 words
A process of claim 1 wherein the mole ratio of glyoxylic compound to N-acylaminomethylphosphonic acid is at least 2:1.
Claim 4
Dependent Claim
30 words
A process of claim 1 wherein the N-acylaminomethylphosphonic acid and the glyoxylic compound thereof are brought together and heated to a temperature between about 50° C. and about 180° C.
Claim 5
Dependent Claim
17 words
A process of claim 3 wherein the temperature is between about 70° C. and about 150° C.
Claim 6
Dependent Claim
9 words
A process of claim 1 wherein R is alkyl.
Claim 7
Dependent Claim
9 words
A process of claim 5 wherein R is methyl.
Claim 8
Dependent Claim
9 words
A process of claim 1 wherein R is phenyl.
Claim 9
Dependent Claim
91 words
A process for the preparation of N-phosphonomethylglycine which comprises bringing together in the presence of water or an aqueous a mineral acid and at a temperature between about 70° C. and about 150° C. a glyoxylic compound which is glyoxylic acid, hydrate, hemiacetal, acetal or alkyl ester thereof and an N-acylaminomethylphosphonic acid represented by the formula ##STR4## wherein R is selected from the group consisting of alkyl having from one to about 6 carbon atoms, and phenyl wherein the mole ratio of glyoxylic acid to N-acylaminomethylglyphosphonic acid is at least 2:1.
Claim 10
Dependent Claim
91 words
A process for the preparation of N-phosphonomethylglycine which comprises bringing together in the presence of water or an aqueous a mineral acid and at a temperature between about 70° C. and about 150° C. a glyoxylic compound which is glyoxylic acid, hydrate, hemiacetal, acetal or alkyl ester thereof and an N-acylaminomethylphosphonic acid represented by the formula ##STR4## wherein R is selected from the group consisting of alkyl having from one to about 6 carbon atoms, and phenyl wherein the mole ratio of glyoxylic acid to N-acylaminomethylglyphosphonic acid is at least 2:1.
Claim 11
Dependent Claim
15 words
A process of claim 8 wherein the mineral acid is hydrochloric acid or sulfuric acid.
Claim 12
Dependent Claim
9 words
A process of claim 8 wherein R is phenyl.
Claim 13
Dependent Claim
12 words
A process of claim 10 wherein the mineral acid is hydrochloric acid.
Claim 14
Dependent Claim
9 words
A process of claim 8 wherein R is methyl.
Claim 15
Dependent Claim
13 words
A process of claim 12 wherein water without added mineral acid is used.
Claim 16
Dependent Claim
28 words
A process of claim 8 wherein the glyoxylic compound is the alkyl ester of glyoxylic acid, wherein the alkyl group contains from one to about six carbon atoms.
Claim 17
Dependent Claim
29 words
A process of claim 8 wherein the glyoxylic compound is the alkyl ester hemiacetal of glyoxylic acid, wherein the alkyl group contains from one to about six carbon atoms.
Claim 18
Dependent Claim
50 words
A process of claim 1 wherein the N-acylaminomethylphosphonic acid is prepared by bringing together under substantially anhydrous reaction conditions an amide represented by the formula ##STR5## wherein R is as defined above, paraformaldehyde, and phosphorus trichloride, and without isolation of the N-acylaminomethylphosphonic acid, adding glyoxylic compound to the reaction mixture.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-07-24 | 1993-01-23 | 1993-07-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-07-24 | 1997-01-23 | 1997-07-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-07-24 | 2001-01-23 | 2001-07-25 | $7700.00 | Window Closed / Lapsed |