GB1428499A - Process for producing n-phosphonomethyl glycine and salts and esters thereof - Google Patents
Process for producing n-phosphonomethyl glycine and salts and esters thereofInfo
- Publication number
- GB1428499A GB1428499A GB5908373A GB5908373A GB1428499A GB 1428499 A GB1428499 A GB 1428499A GB 5908373 A GB5908373 A GB 5908373A GB 5908373 A GB5908373 A GB 5908373A GB 1428499 A GB1428499 A GB 1428499A
- Authority
- GB
- United Kingdom
- Prior art keywords
- electrolytic
- phosphonomethyl glycine
- solution
- medium
- dec
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
Abstract
1428499 Preparing N-phosphonomethyl glycine and derivatives thereof MONSANTO CO 20 Dec 1973 [21 Dec 1972 6 Aug 1973] 59083/73 Heading C2P N-Phosphonomethyl glycine and its derivatives of the formula wherein M, M 1 and M 2 are each individually hydrogen, alkoxyalkyl groups, alkoxyalkoxyalkyl groups, alkyl groups of from 1 to 18 carbon atoms, alkali metal, alkaline earth metal, ammonium or organic ammonium provided that at least one of M, M 1 and M 2 is hydrogen, alkali metal or alkaline earth metal, are obtained by subjecting an aqueous electrolytic medium containing an N-organo-N-phosphonomethylamino acetic acid compound of the formula wherein R is selected from allyl, halogen-substituted allyl, benzyl, halosubstituted benzyl, 2,2,2-triphenylethyl, diphenylmethyl, 1,2- or 2,2-diphenylethyl, -CH 2 CH 2 OH, -CH 2 NO 2 , -CH 2 CN, -CH 2 C(O)C n H 2n+1 , -CH 2 -CH 2 OR<SP>1</SP>, -CH 2 Cl, -CH 2 CHO, -CH 2 CH 2 NR<SP>1</SP>R<SP>11</SP>, -CH 2 OR<SP>1</SP>, -CH 2 CCl 3 , CH 2 C(O)NR<SP>1</SP>R<SP>11</SP>, M 3 OOCCH 2 or (M 3 O)(M 4 O)P(O)CH 2 - wherein R<SP>1</SP> is C 1 -C 6 alkyl, R<SP>11</SP> is H or is as defined for R<SP>1</SP>, M 3 and M 4 are as defined for M, M 1 and M 2 , and n is 1 to 6 to an electromotive force to convert the amino acetic acid compound to N-phosphonomethyl glycine or derivative thereof. Preferably a 2% to 30% by weight solution of the compound II dissolved in 1À0 to 37% by weight aqueous HCl is charged into an electrolytic cell maintained at 25 to 110 C. and having noble metal, graphite or carbon electrodes and a current passed through at between 1 and 700 ma./cm.<SP>2</SP> for a time sufficient to effect the electrolytic conversion. The resultant solution may be vacuum evaporated to remove the aqueous HCl medium and volatile by-products and the residue dissolved in water and recovered by recrystallization on cooling the solution. Other acids, or bases or salts of such bases, may also be used to make the electrolytic solution conductive and a formaldehyde-scavenging agent, e.g. urea may be included in the medium.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31749872A | 1972-12-21 | 1972-12-21 | |
| US00385932A US3835000A (en) | 1972-12-21 | 1973-08-06 | Electrolytic process for producing n-phosphonomethyl glycine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1428499A true GB1428499A (en) | 1976-03-17 |
Family
ID=26980991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5908373A Expired GB1428499A (en) | 1972-12-21 | 1973-12-20 | Process for producing n-phosphonomethyl glycine and salts and esters thereof |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3835000A (en) |
| JP (1) | JPS5111094B2 (en) |
| AR (1) | AR216882A1 (en) |
| BG (1) | BG24411A3 (en) |
| BR (1) | BR7309442D0 (en) |
| CA (1) | CA1001992A (en) |
| CH (1) | CH592105A5 (en) |
| DD (1) | DD110503A5 (en) |
| DK (1) | DK134559B (en) |
| EG (1) | EG11507A (en) |
| ES (1) | ES421614A1 (en) |
| FR (1) | FR2211468B1 (en) |
| GB (1) | GB1428499A (en) |
| HU (1) | HU168961B (en) |
| IE (1) | IE38667B1 (en) |
| IL (1) | IL43880A (en) |
| IT (1) | IT1001432B (en) |
| NL (1) | NL163218C (en) |
| PH (1) | PH10205A (en) |
| PL (1) | PL94988B1 (en) |
| RO (1) | RO64474A (en) |
| SE (1) | SE403379B (en) |
| YU (1) | YU37363B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2144425A (en) * | 1983-07-27 | 1985-03-06 | Rhone Poulenc Agrochimie | Sulphonimide herbicides containing an aminomethylphosphonic group |
| GB2155476A (en) * | 1984-02-23 | 1985-09-25 | Rhone Poulenc Agrochimie | Esters of the family of N-phosphonomethylglycine and their use in the preparation of known herbicides |
| WO2006107824A2 (en) * | 2005-04-01 | 2006-10-12 | Monsanto Technology Llc | Control of n-(phosphonomethyl) iminodiacetic acid conversion in manufacture of glyphosate |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1494197A (en) * | 1973-11-30 | 1977-12-07 | Ici Ltd | Electrochemical process for the preparation of n-phosphonomethyl glycine |
| US3991095A (en) * | 1975-12-29 | 1976-11-09 | Monsanto Company | N-thiolcarbonyl derivatives of N-phosphonomethylglycine |
| US4047927A (en) * | 1976-08-13 | 1977-09-13 | Monsanto Company | N-(2-hydroxyalkyl) derivatives of N-phosphonomethylglycine and the herbicidal use thereof |
| US4063922A (en) * | 1976-08-13 | 1977-12-20 | Monsanto Company | N-(2-hydroxyalkyl) derivatives of N-phosphonomethylglycine for treatment of sugarcane |
| NL7713959A (en) * | 1976-12-20 | 1978-06-22 | Monsanto Co | PROCESS FOR PREPARING N-PHOSPHONOMETHYLGLYCIN SALTS. |
| US4105432A (en) * | 1977-07-18 | 1978-08-08 | Monsanto Company | Cyclized derivatives of N-(2-hydroxyalkyl)-N-phosphonomethylglycine compounds |
| US4218235A (en) * | 1978-07-10 | 1980-08-19 | Monsanto Company | Ester derivatives of n-trifluoroacetyl-n-phosphonomethylglycine and the herbicidal use thereof |
| US4180394A (en) * | 1978-07-10 | 1979-12-25 | Monsanto Company | Derivatives of N-trifluoroacetyl-N-phosphonomethylglycinates and the herbicidal use thereof |
| US4300942A (en) * | 1978-09-29 | 1981-11-17 | Monsanto Company | N-(Substituted carbonyl) derivatives of N-phos-phinylmethylglycinates and the herbicidal use thereof |
| US4251258A (en) * | 1978-09-29 | 1981-02-17 | Monsanto Company | N-(Substituted carbonyl) derivatives of N-phosphinylmethylglycinates and the herbicidal use thereof |
| US4251256A (en) * | 1978-12-22 | 1981-02-17 | Monsanto Company | Herbicidal N-substituted ethylene derivatives of N-phosphonomethylglycine |
| US4261727A (en) * | 1979-08-02 | 1981-04-14 | Monsanto Company | Herbicidal N-substituted triesters of N-phosphonomethylglycine |
| US4384880A (en) * | 1980-12-04 | 1983-05-24 | Stauffer Chemical Company | Trialkylsulfonium salts of N-phosphonomethyl-glycine and their use as plant growth regulators and herbicides |
| US4315765A (en) * | 1980-12-04 | 1982-02-16 | Stauffer Chemical Company | Trialkylsulfonium salts of n-phosphonomethylglycine and their use as plant growth regulators and herbicides |
| US4376644A (en) * | 1980-12-04 | 1983-03-15 | Stauffer Chemical Company | Tri-mixed alkylsulfonium salts of N-phosphonomethylglycine and their use as plant growth regulators and herbicides |
| US4328027A (en) * | 1981-04-16 | 1982-05-04 | Stauffer Chemical Company | Di-triethylamine salt of N,N'-bis-carboethoxymethyl-N,N'-bis-phosphonomethylurea and its use as a plant growth regulator |
| US4437874A (en) | 1981-11-25 | 1984-03-20 | Stauffer Chemical Company | Tri-mixed alkylsulfonium salts of N-phosphonomethylgylcine and their use as plant growth regulators and herbicides |
| IL65187A (en) * | 1982-03-08 | 1985-03-31 | Geshuri Lab Ltd | N-phosphonomethylglycine derivatives,processes for their preparation and herbicidal compositions containing them |
| US4472189A (en) * | 1982-12-27 | 1984-09-18 | Stauffer Chemical Co. | Stannic N-phosphonomethyglycine and its use as a herbicide |
| IL77364A (en) * | 1984-12-28 | 1991-01-31 | Monsanto Co | Thermal dealkylation of n-alkyl n-phosphono-methylglycine |
| US4921991A (en) * | 1985-02-22 | 1990-05-01 | Guy Lacroix | Preparation of esters of the N-phosphonomethylglycine and the N-phosphonomethyl glycines |
| US4804500A (en) * | 1985-04-22 | 1989-02-14 | Monsanto Company | Amine dealkylation process |
| US4684483A (en) * | 1985-09-23 | 1987-08-04 | Monsanto Company | Preparation of N-substituted amino acids |
| US5187292A (en) * | 1988-08-18 | 1993-02-16 | Rhone-Poulenc Agrochimie | N-sulfomethylglycinate, use in the preparation of herbicides of the glyphosate type |
| FR2635522B1 (en) * | 1988-08-18 | 1990-11-16 | Rhone Poulenc Agrochimie | N-SULFONOMETHYLGLYCINATE PROCESS FOR THE PREPARATION, USE IN THE PREPARATION OF GLYPHOSATE-LIKE HERBICIDES |
| CZ164699A3 (en) * | 1998-02-12 | 1999-12-15 | Monsanto Company | Process for preparing glyphosate, salt or ester thereof by oxidation of n-substituted glyphosates a oxidation catalyst used during execution of this process |
| US6232494B1 (en) | 1998-02-12 | 2001-05-15 | Monsanto Company | Process for the preparation of N-(phosphonomethyl)glycine by oxidizing N-substituted N-(phosphonomethyl)glycine |
| US6417133B1 (en) | 1998-02-25 | 2002-07-09 | Monsanto Technology Llc | Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
| BR0111041A (en) | 2000-05-22 | 2004-06-15 | Monsanto Technology Llc | Reaction systems for producing n- (phosphonomethyl) glycine compounds |
| TW200624171A (en) * | 2004-09-15 | 2006-07-16 | Monsanto Technology Llc | Oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
| US8252953B2 (en) | 2008-05-01 | 2012-08-28 | Monsanto Technology Llc | Metal utilization in supported, metal-containing catalysts |
-
1973
- 1973-08-06 US US00385932A patent/US3835000A/en not_active Expired - Lifetime
- 1973-11-21 PH PH15246A patent/PH10205A/en unknown
- 1973-11-30 BR BR9442/73A patent/BR7309442D0/en unknown
- 1973-12-18 RO RO7377044A patent/RO64474A/en unknown
- 1973-12-19 ES ES421614A patent/ES421614A1/en not_active Expired
- 1973-12-19 NL NL7317370.A patent/NL163218C/en not_active IP Right Cessation
- 1973-12-20 GB GB5908373A patent/GB1428499A/en not_active Expired
- 1973-12-20 JP JP48142934A patent/JPS5111094B2/ja not_active Expired
- 1973-12-20 CA CA188,637A patent/CA1001992A/en not_active Expired
- 1973-12-20 IE IE2308/73A patent/IE38667B1/en unknown
- 1973-12-20 EG EG480/73A patent/EG11507A/en active
- 1973-12-20 IT IT3554/73A patent/IT1001432B/en active
- 1973-12-20 DD DD175538A patent/DD110503A5/xx unknown
- 1973-12-20 PL PL1973167559A patent/PL94988B1/pl unknown
- 1973-12-20 HU HUMO891A patent/HU168961B/hu not_active IP Right Cessation
- 1973-12-20 SE SE7317193A patent/SE403379B/en unknown
- 1973-12-20 FR FR7345835A patent/FR2211468B1/fr not_active Expired
- 1973-12-20 DK DK694073AA patent/DK134559B/en not_active IP Right Cessation
- 1973-12-20 YU YU3305/73A patent/YU37363B/en unknown
- 1973-12-20 AR AR251626A patent/AR216882A1/en active
- 1973-12-20 IL IL43880A patent/IL43880A/en unknown
- 1973-12-20 CH CH1796673A patent/CH592105A5/xx not_active IP Right Cessation
- 1973-12-20 BG BG7300025303A patent/BG24411A3/en unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2144425A (en) * | 1983-07-27 | 1985-03-06 | Rhone Poulenc Agrochimie | Sulphonimide herbicides containing an aminomethylphosphonic group |
| GB2193497A (en) * | 1983-07-27 | 1988-02-10 | Rhone Poulenc Agrochimie | Intermediates useful in the preparation of herbicidal compounds |
| GB2155476A (en) * | 1984-02-23 | 1985-09-25 | Rhone Poulenc Agrochimie | Esters of the family of N-phosphonomethylglycine and their use in the preparation of known herbicides |
| WO2006107824A2 (en) * | 2005-04-01 | 2006-10-12 | Monsanto Technology Llc | Control of n-(phosphonomethyl) iminodiacetic acid conversion in manufacture of glyphosate |
| WO2006107824A3 (en) * | 2005-04-01 | 2007-02-22 | Monsanto Technology Llc | Control of n-(phosphonomethyl) iminodiacetic acid conversion in manufacture of glyphosate |
| US7799571B2 (en) | 2005-04-01 | 2010-09-21 | Monsanto Technology Llc | Control of N-(phosphonomethyl)iminodiacetic acid conversion in manufacture of glyphosate |
| US9409935B2 (en) | 2005-04-01 | 2016-08-09 | Monsanto Technology Llc | Control of N-(phosphonomethyl)iminodiacetic acid conversion in manufacture of glyphosate |
| US11067502B2 (en) | 2005-04-01 | 2021-07-20 | Monsanto Technology Llc | Control of n-(phosphonomethyl)iminodiacetic acid conversion in manufacture of glyphosate |
| US11802835B2 (en) | 2005-04-01 | 2023-10-31 | Monsanto Technology Llc | Control of N-(phosphonomethyl)iminodiacetic acid conversion manufacture of glyphosate |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2363634B2 (en) | 1977-06-02 |
| JPS4988827A (en) | 1974-08-24 |
| FR2211468A1 (en) | 1974-07-19 |
| CH592105A5 (en) | 1977-10-14 |
| NL163218B (en) | 1980-03-17 |
| JPS5111094B2 (en) | 1976-04-08 |
| DK134559B (en) | 1976-11-29 |
| IE38667B1 (en) | 1978-05-10 |
| FR2211468B1 (en) | 1976-05-07 |
| IL43880A (en) | 1976-05-31 |
| AR216882A1 (en) | 1980-02-15 |
| NL163218C (en) | 1980-08-15 |
| IE38667L (en) | 1974-06-21 |
| AU6385173A (en) | 1975-06-26 |
| PH10205A (en) | 1976-09-27 |
| EG11507A (en) | 1977-08-15 |
| YU330573A (en) | 1983-04-27 |
| IL43880A0 (en) | 1974-03-14 |
| HU168961B (en) | 1976-08-28 |
| DD110503A5 (en) | 1974-12-20 |
| RO64474A (en) | 1979-05-15 |
| DE2363634A1 (en) | 1974-06-27 |
| YU37363B (en) | 1984-08-31 |
| BG24411A3 (en) | 1978-02-10 |
| BR7309442D0 (en) | 1974-08-29 |
| ES421614A1 (en) | 1976-10-16 |
| SE403379B (en) | 1978-08-14 |
| US3835000A (en) | 1974-09-10 |
| CA1001992A (en) | 1976-12-21 |
| DK134559C (en) | 1977-05-09 |
| PL94988B1 (en) | 1977-09-30 |
| NL7317370A (en) | 1974-06-25 |
| IT1001432B (en) | 1976-04-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |