Patent US4568432A successfully refreshed from Google Patents.
US4568432A
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Process for preparing glyphosate and glyphosate derivatives
Assignee: Monsanto Co
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Filing: 1984-12-28
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Granted: 1986-02-04
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Expires: 2004-12-28
Abstract
Abstract A process for preparing glyphosate and derivatives of related structure. A precursor primary or secondary amine, such as glycine, is condensed with a carbonyl compound, such as formylphosphonic acid or its acetals, and the condensation product is reduced to produce the desired product.
Inventors
- 👤 Thomas E. Rogers
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 00:57
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/44; C07F9/3804; C07F9/3808; C07F9/3813; C07F9/3817; C25; C25B; C25B3/00; C25B3/01; C25B3/07; C25B3/09; C25B3/20; C25B3/25
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
291 words
A process for preparing a compound of the formula ##STR8## wherein R can be hydrogen and R, R 1 , and R 2 are independently selected from the group consisting of --OH; --SH; --NR 4 R 5 wherein R 4 and R 5 are independently selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl having 1 through 4 carbon atoms, alkenyl having 2 through 4 carbon atoms, and R 4 and R 5 together with the nitrogen atoms can form a heterocyclic ring; --OR 6 and SR 6 wherein R 6 is selected from the group consisting of monovalent hydrocarbon groups, monovalent hydrocarbonoxyhydrocarbon groups each containing from 1 to 18 carbon atoms, halogenated monovalent hydrocarbon groups, halogenated monovalent hydrocarbonoxyhydrocarbon groups each containing from 1 to 18 carbon atoms and from 1 to 3 halogens, and groups having the formula ##STR9## wherein n is from 1 to 4, and R 4 and R 5 are as defined above; --OR 7 wherein R 7 is a herbicidally acceptable salt-forming cation; and R 3 is hydrogen or alkyl, the process comprising: condensing a precursor primary or secondary amine corresponding to the formula ##STR10## where R and R 3 are as defined above, in an aqueous reaction medium, with carbonyl compound, or hydrate or acetal thereof, said carbonyl compound corresponding to the Formula (III) or (IV) ##STR11## wherein R 1 and R 2 are as defined above, R 12 and R 13 are independently selected from hydrogen, alkyl, hydroxyalkyl having 1 to 4 carbon atoms, alkenyl and alkyl having 2 to 4 carbon atoms joined through the oxygen atoms to form a cyclic acetal, aryl, substituted aryl, or heterocyclic moieties; and reducing the condensation product without isolation to produce a compound of Formula (I).
Claim 2
Dependent Claim
291 words
A process for preparing a compound of the formula ##STR8## wherein R can be hydrogen and R, R 1 , and R 2 are independently selected from the group consisting of --OH; --SH; --NR 4 R 5 wherein R 4 and R 5 are independently selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl having 1 through 4 carbon atoms, alkenyl having 2 through 4 carbon atoms, and R 4 and R 5 together with the nitrogen atoms can form a heterocyclic ring; --OR 6 and SR 6 wherein R 6 is selected from the group consisting of monovalent hydrocarbon groups, monovalent hydrocarbonoxyhydrocarbon groups each containing from 1 to 18 carbon atoms, halogenated monovalent hydrocarbon groups, halogenated monovalent hydrocarbonoxyhydrocarbon groups each containing from 1 to 18 carbon atoms and from 1 to 3 halogens, and groups having the formula ##STR9## wherein n is from 1 to 4, and R 4 and R 5 are as defined above; --OR 7 wherein R 7 is a herbicidally acceptable salt-forming cation; and R 3 is hydrogen or alkyl, the process comprising: condensing a precursor primary or secondary amine corresponding to the formula ##STR10## where R and R 3 are as defined above, in an aqueous reaction medium, with carbonyl compound, or hydrate or acetal thereof, said carbonyl compound corresponding to the Formula (III) or (IV) ##STR11## wherein R 1 and R 2 are as defined above, R 12 and R 13 are independently selected from hydrogen, alkyl, hydroxyalkyl having 1 to 4 carbon atoms, alkenyl and alkyl having 2 to 4 carbon atoms joined through the oxygen atoms to form a cyclic acetal, aryl, substituted aryl, or heterocyclic moieties; and reducing the condensation product without isolation to produce a compound of Formula (I).
Claim 3
Dependent Claim
53 words
The process of claim 1 wherein at least one of R, R 1 , and R 2 is OR 7 wherein R is a salt-forming cation selected from the group consisting of alkali metals, alkaline earth metals, copper, zinc, manganese, nickel, ammonium, aliphatic ammonium, phosphonium, aliphatic phosphonium, aliphatic sulfonium, and primary aryl ammonium.
Claim 4
Dependent Claim
28 words
A process as set forth in claim 1 wherein the pH of said reaction medium is between about 5.5 and about 12.0 during said condensation and reduction reactions.
Claim 5
Dependent Claim
27 words
A process as set forth in claim 3 wherein said pH is adjusted between about 7.0 and about 12.0 during said reactions by addition of a base.
Claim 6
Dependent Claim
35 words
A process as set forth in claim 1 wherein the concentration of each of said precursor amine and said carbonyl compound reactants in said aqueous medium is between about 2% and about 20% by weight.
Claim 7
Dependent Claim
26 words
A process as set forth in claim 5 wherein the molar ratio of said carbonyl compounds to said precursor amine is between 1.0 and about 1.2.
Claim 8
Dependent Claim
15 words
A process as set forth in claim 1 wherein said reduction is carried out electrochemically.
Claim 9
Dependent Claim
18 words
A process as set forth in claim 7 wherein said reduction is carried out using a mercury electrode.
Claim 10
Dependent Claim
43 words
A process as set forth in claim 7 wherein the reduction is carried out in a cell having a porous barrier between cathode and anode, and said aqueous medium containing said precursor amine and said carbonyl compound comprises the catholyte in said cell.
Claim 11
Dependent Claim
29 words
A process as set forth in claim 7 wherein the cell is operated at a current density of between about 0.001 and about 0.5 amperes per cm 2 .
Claim 12
Dependent Claim
18 words
A process as set forth in claim 1 wherein said reduction reaction is carried out by catalytic hydrogenation.
Claim 13
Dependent Claim
33 words
A process as set forth in claim 11 wherein said catalyst is selected from the group consisting of platinum, palladium, osmium, iridium, rhodium, ruthenium, nickel, cobalt, copper, zinc, and compounds of said metals.
Claim 14
Dependent Claim
20 words
A process as set forth in claim 12 wherein said catalyst comprises a platinum group metal on a carbon support.
Claim 15
Dependent Claim
18 words
A process as set forth in claim 12 wherein said catalyst comprises a nickel or a nickel compound.
Claim 16
Dependent Claim
14 words
A process as set forth in claim 14 wherein said catalyst comprises Raney nickel.
Claim 17
Dependent Claim
15 words
A process as set forth in claim 12 wherein said catalyst comprises a water-soluble compound.
Claim 18
Dependent Claim
23 words
A process as set forth in claim 1 wherein R 3 is H and R, R 1 , and R 2 are OH.
Claim 19
Dependent Claim
41 words
A process as set forth in claim 1 wherein one of R, R 1 and R 2 is OR 7 , and R 7 is selected from a herbicidally acceptable salt-forming cation which renders the compound more readily soluble in water.
Claim 20
Dependent Claim
18 words
A process as set forth in claim 4 wherein said base comprises a tertiary, secondary, or primary amine.
Claim 21
Dependent Claim
72 words
A process as set forth in claim 1 wherein R 3 is represented by the formula ##STR12## wherein R 8 , R 9 , R 10 , and R 11 are independently selected from the group consisting of hydrogen, alkyl C 1 - 6 , aryl, and substituted aryl provided no more than two of R 8 , R 9 , R 10 , and R 11 are aryl or substituted aryl.
Claim 22
Dependent Claim
13 words
A process as set forth in claim 20 wherein R 3 is isopropyl.
References Cited (Backward Citations)
US3288846A
Cited
US4233056A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-02-03 | 1989-08-05 | 1990-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-02-03 | 1993-08-05 | 1994-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-02-03 | 1997-08-05 | 1998-02-04 | $7700.00 | Window Closed / Lapsed |