IE38667L - N-phosphonomethyl glycine - Google Patents
N-phosphonomethyl glycineInfo
- Publication number
- IE38667L IE38667L IE732308A IE230873A IE38667L IE 38667 L IE38667 L IE 38667L IE 732308 A IE732308 A IE 732308A IE 230873 A IE230873 A IE 230873A IE 38667 L IE38667 L IE 38667L
- Authority
- IE
- Ireland
- Prior art keywords
- electrolytic
- solution
- phosphonomethyl glycine
- medium
- dec
- Prior art date
Links
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title abstract 4
- -1 acetic acid compound Chemical class 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 239000008151 electrolyte solution Substances 0.000 abstract 1
- 229960002449 glycine Drugs 0.000 abstract 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 abstract 1
- 229910002804 graphite Inorganic materials 0.000 abstract 1
- 239000010439 graphite Substances 0.000 abstract 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 239000002516 radical scavenger Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
-
- 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 Table
- 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 ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Electrolytic Production Of Metals (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
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.
[GB1428499A]
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE38667L true IE38667L (en) | 1974-06-21 |
| IE38667B1 IE38667B1 (en) | 1978-05-10 |
Family
ID=26980991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2308/73A IE38667B1 (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) |
Families Citing this family (34)
| 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 |
| US4063922A (en) * | 1976-08-13 | 1977-12-20 | Monsanto Company | N-(2-hydroxyalkyl) derivatives of N-phosphonomethylglycine for treatment of sugarcane |
| US4047927A (en) * | 1976-08-13 | 1977-09-13 | Monsanto Company | N-(2-hydroxyalkyl) derivatives of N-phosphonomethylglycine and the herbicidal use thereof |
| MX4703E (en) * | 1976-12-20 | 1982-08-04 | Monsanto Co | IMPROVED PROCEDURE FOR THE PREPARATION OF MONKEY AND DISALS OF N-PHOSPHONOMETILGLICINA |
| US4105432A (en) * | 1977-07-18 | 1978-08-08 | Monsanto Company | Cyclized derivatives of N-(2-hydroxyalkyl)-N-phosphonomethylglycine compounds |
| US4180394A (en) * | 1978-07-10 | 1979-12-25 | Monsanto Company | Derivatives of N-trifluoroacetyl-N-phosphonomethylglycinates and the herbicidal use thereof |
| US4218235A (en) * | 1978-07-10 | 1980-08-19 | Monsanto Company | Ester derivatives of n-trifluoroacetyl-n-phosphonomethylglycine 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 |
| US4300942A (en) * | 1978-09-29 | 1981-11-17 | Monsanto Company | N-(Substituted carbonyl) derivatives of N-phos-phinylmethylglycinates 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 |
| ES8603901A1 (en) * | 1983-07-27 | 1986-01-01 | Rhone Poulenc Agrochimie | Herbicides of the sulfon imide-type with an aminomethylphosphonic group. |
| FR2560198B1 (en) * | 1984-02-23 | 1987-05-07 | Rhone Poulenc Agrochimie | ESTERS OF THE N-PHOSPHONOMETHYLGLYCIN FAMILY AND THEIR USE FOR THE PREPARATION OF KNOWN HERBICIDES |
| 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 |
| 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 |
| US5187292A (en) * | 1988-08-18 | 1993-02-16 | Rhone-Poulenc Agrochimie | N-sulfomethylglycinate, use in the preparation of herbicides of the glyphosate type |
| EP1062221B1 (en) * | 1998-02-12 | 2006-05-10 | Monsanto Technology LLC | Process for making glyphosate by oxidizing n-substituted glyphosates |
| 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 |
| US7015351B2 (en) * | 2000-05-22 | 2006-03-21 | Monsanto Technology Llc | Reaction systems for making N-(phosphonomethyl) glycine compounds |
| WO2006031938A2 (en) * | 2004-09-15 | 2006-03-23 | Monsanto Technology Llc | Oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
| CN101218242A (en) | 2005-04-01 | 2008-07-09 | 孟山都技术公司 | Control of N-(phosphonomethyl) iminodiacetic acid conversion in manufacture of glyphosate |
| 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 NL NL7317370.A patent/NL163218C/en not_active IP Right Cessation
- 1973-12-19 ES ES421614A patent/ES421614A1/en not_active Expired
- 1973-12-20 YU YU3305/73A patent/YU37363B/en unknown
- 1973-12-20 HU HUMO891A patent/HU168961B/hu not_active IP Right Cessation
- 1973-12-20 DD DD175538A patent/DD110503A5/xx unknown
- 1973-12-20 IT IT3554/73A patent/IT1001432B/en active
- 1973-12-20 SE SE7317193A patent/SE403379B/en unknown
- 1973-12-20 IE IE2308/73A patent/IE38667B1/en unknown
- 1973-12-20 CH CH1796673A patent/CH592105A5/xx not_active IP Right Cessation
- 1973-12-20 DK DK694073AA patent/DK134559B/en not_active IP Right Cessation
- 1973-12-20 PL PL1973167559A patent/PL94988B1/pl unknown
- 1973-12-20 FR FR7345835A patent/FR2211468B1/fr not_active Expired
- 1973-12-20 BG BG025303A patent/BG24411A3/en unknown
- 1973-12-20 JP JP48142934A patent/JPS5111094B2/ja not_active Expired
- 1973-12-20 GB GB5908373A patent/GB1428499A/en not_active Expired
- 1973-12-20 AR AR251626A patent/AR216882A1/en active
- 1973-12-20 CA CA188,637A patent/CA1001992A/en not_active Expired
- 1973-12-20 IL IL43880A patent/IL43880A/en unknown
- 1973-12-20 EG EG480/73A patent/EG11507A/en active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2211468A1 (en) | 1974-07-19 |
| BR7309442D0 (en) | 1974-08-29 |
| NL163218B (en) | 1980-03-17 |
| JPS4988827A (en) | 1974-08-24 |
| FR2211468B1 (en) | 1976-05-07 |
| DD110503A5 (en) | 1974-12-20 |
| SE403379B (en) | 1978-08-14 |
| IL43880A0 (en) | 1974-03-14 |
| BG24411A3 (en) | 1978-02-10 |
| EG11507A (en) | 1977-08-15 |
| AR216882A1 (en) | 1980-02-15 |
| DK134559C (en) | 1977-05-09 |
| YU37363B (en) | 1984-08-31 |
| PH10205A (en) | 1976-09-27 |
| US3835000A (en) | 1974-09-10 |
| NL163218C (en) | 1980-08-15 |
| DE2363634B2 (en) | 1977-06-02 |
| CA1001992A (en) | 1976-12-21 |
| GB1428499A (en) | 1976-03-17 |
| IE38667B1 (en) | 1978-05-10 |
| DK134559B (en) | 1976-11-29 |
| ES421614A1 (en) | 1976-10-16 |
| AU6385173A (en) | 1975-06-26 |
| CH592105A5 (en) | 1977-10-14 |
| RO64474A (en) | 1979-05-15 |
| NL7317370A (en) | 1974-06-25 |
| HU168961B (en) | 1976-08-28 |
| DE2363634A1 (en) | 1974-06-27 |
| IL43880A (en) | 1976-05-31 |
| YU330573A (en) | 1983-04-27 |
| JPS5111094B2 (en) | 1976-04-08 |
| IT1001432B (en) | 1976-04-20 |
| PL94988B1 (en) | 1977-09-30 |
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