US4053505A
Expired / Lapsed
US
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Preparation of n-phosphonomethyl glycine
Assignee: Monsanto Co
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Filing: 1976-01-05
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Granted: 1977-10-11
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Expires: 1996-01-05
Abstract
Abstract A herbicidal compound N-phosphonomethyl glycine is prepared by (a) reacting 1,3,5-tricarbohydrocarbonoxymethyl hexahydrotriazine with a di-monovalent hydrocarbon phosphite to form an ester of N-phosphonomethyl glycine which is thereafter (b) hydrolyzed and the N-phosphonomethyl glycine is recovered.
Inventors
- 👤 Gerard A. Dutra
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 08:26
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3808; C07F9/3813
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
113 words
A process for the production of N-phosphonomethyl glycine which comprises (a) reacting a 1,3,5-tricarbohydrocarbonoxy-methyl-hexahydrotriazine of the formula ##STR2## wherein R is a monovalent hydrocarbon or substituted hydrocarbon radical in which the substituent is inert to the reaction; with a phosphite ester of the formula ##STR3## wherein the R' is the same or different radical as defined for R, in the absence of a catalyst, by heating a mixture of said triazine and said ester to a temperature sufficiently elevated to initiate and maintain the reaction to form a triester of N-phosphonomethyl glycine of the formula ##STR4## wherein R and R' are as above defined, (b) hydrolyzing the triester and (c) recovering N-phosphonomethyl glycine.
Claim 2
Dependent Claim
113 words
A process for the production of N-phosphonomethyl glycine which comprises (a) reacting a 1,3,5-tricarbohydrocarbonoxy-methyl-hexahydrotriazine of the formula ##STR2## wherein R is a monovalent hydrocarbon or substituted hydrocarbon radical in which the substituent is inert to the reaction; with a phosphite ester of the formula ##STR3## wherein the R' is the same or different radical as defined for R, in the absence of a catalyst, by heating a mixture of said triazine and said ester to a temperature sufficiently elevated to initiate and maintain the reaction to form a triester of N-phosphonomethyl glycine of the formula ##STR4## wherein R and R' are as above defined, (b) hydrolyzing the triester and (c) recovering N-phosphonomethyl glycine.
Claim 3
Dependent Claim
17 words
A process of claim 1 wherein step (a) is conducted in the presence of a suitable solvent.
Claim 4
Dependent Claim
21 words
A process according to claim 2 wherein said triester of N-phosphonomethyl glycine is isolated before the hydrolysis by removing the solvent.
Claim 5
Dependent Claim
28 words
A process according to claim 1 wherein R represents an alkyl radical of from 1 to 6 carbon atoms and R' represents a phenyl or substituted phenyl radical.
Claim 6
Dependent Claim
17 words
A process in accordance with claim 1 wherein the temperature is between 20° C. and 150° C.
Claim 7
Dependent Claim
24 words
A process in accordance with claim 1 wherein the hydrolysis is carried out in aqueous hydrohalic acid having a normality of at least 1.0.
Claim 8
Dependent Claim
22 words
A process according to claim 2 wherein aqueous hydrohalic acid is added to the reaction mixture before the removal of the solvent.
References Cited (Backward Citations)
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US3476799A
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US3549728A
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US3886204A
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US3799758A
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US3923877A
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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) | 1980-10-10 | 1981-04-11 | 1981-10-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-10 | 1985-04-11 | 1985-10-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-10 | 1989-04-11 | 1989-10-11 | $7700.00 | Window Closed / Lapsed |