IL43880A - Process for producing n-phosphonomethyl glycines - Google Patents
Process for producing n-phosphonomethyl glycinesInfo
- Publication number
- IL43880A IL43880A IL43880A IL4388073A IL43880A IL 43880 A IL43880 A IL 43880A IL 43880 A IL43880 A IL 43880A IL 4388073 A IL4388073 A IL 4388073A IL 43880 A IL43880 A IL 43880A
- Authority
- IL
- Israel
- Prior art keywords
- acetic acid
- medium
- aqueous electrolytic
- carbon
- aqueous
- Prior art date
Links
- 150000002333 glycines Chemical class 0.000 title 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 239000002609 medium Substances 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- -1 2,2,2-tri-phenylethyl Chemical group 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910002804 graphite Inorganic materials 0.000 claims 4
- 239000010439 graphite Substances 0.000 claims 4
- 239000012736 aqueous medium Substances 0.000 claims 3
- 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 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 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 claims 1
- KOJRWLCMBRYCBJ-UHFFFAOYSA-N 2-[benzyl(phosphonomethyl)amino]acetic acid Chemical compound OC(=O)CN(CP(O)(O)=O)CC1=CC=CC=C1 KOJRWLCMBRYCBJ-UHFFFAOYSA-N 0.000 claims 1
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 229960002449 glycine Drugs 0.000 claims 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
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 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Electric Double-Layer Capacitors Or The Like (AREA)
- Electrolytic Production Of Metals (AREA)
Claims (15)
1. AG-9 7 · φ WHAT IS CLAIMED IS :
2. 1. A process for producing an N-phosphonomethyl glycine of the formula wherein M, i and M2 are each individually hydrogen, alkoxy-alkyl 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, Mi and M2 is hydrogen, alkali metal or alkaline earth metal which comprises subjecting an aqueous electrolytic medium containing an N-organo-N-phosphono-methylamino acetic acid compound of the formula wherein R is a member of the class consisting of allyl, halogen substituted allyl, benzyl, halosubstituted benzyl, 2,2,2-tri-phenylethyl, diphenylmethyl , 1,2- or 2 ,2-diphenylethyl , -CH2CH20H, CH2N02, CH2CN, 0 CH2C-CnH2n + 1} 0 CH2-CH20R', CH2Cl, CH2CH0 , CH2CH2NR', CH20R', CH2CCl
3. , CH2C-N-R R" R" wherein R' is alkyl of from 1 to 6 carbon atoms, R" is H or R', n is an integer of 1 to 6, and M3 and M4 are as defined for M, Mi and M2 to an electromotive force whereby said acetic acid compound is oxidized to N-phosphonomethyl glycine. AG-947 tion is at least 1% by weight of the total medium. 3- A process as claimed in Claim 1 wherein the aqueous electrolytic medium is an acidic aqueous medium.
4. A process as claimed in Claim 1 wherein the aqueous electrolytic medium is a basic aqueous medium.
5. · A process as claimed in Claim 3 wherein the acidic aqueous medium is hydrochloric acid.
6. A process as claimed in Claim 5 wherein the hydrochloric acid concentration is from 10 to about 25% .
7. A process as claimed in Claim 1 wherein the concentration of the N-organo-N-phosphonomethylamino acetic acid compound is from about 5 % to about 30$ by weight of the aqueous electrolytic medium.
8. A process as claimed in Claim 1 wherein the process is conducted in an electrolytic cell having noble metal, carbon, or graphite electrodes.
9. A process as claimed in Claim 1 wherein the current density is from 1.0 to about 700 ma/cm^.
10. A process as claimed in Claim 8 wherein both electrodes are carbon or graphite electrodes.
11. A process as claimed in Claim 10 wherein the graphite is porous graphite.
12. A process as claimed in Claim 10 wherein the carbon is porous carbon.
13. A process as claimed in Claim 1 wherein the aqueous electrolytic medium also contains urea. 1A..
14. A process as claimed in Claim 1 wherein the aqueous electrolytic medium contains a salt.
15. The process as claimed in Claim 1 wherein the N-organo-N-phosphonomethy lamino acetic acid compound is N- AG-947 ■ of N-phosphonomethylimino diacetic acid, N-allyl-N-phosphono-methylamino acetic acid, N-benzyl-N-phosphonomethylamino acetic acid or bis-(N-phosphonomethyl)amino acetic acid. Attorneys for Applicant
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 |
---|---|
IL43880A0 IL43880A0 (en) | 1974-03-14 |
IL43880A true IL43880A (en) | 1976-05-31 |
Family
ID=26980991
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL43880A IL43880A (en) | 1972-12-21 | 1973-12-20 | Process for producing n-phosphonomethyl glycines |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
ES8603901A1 (en) * | 1983-07-27 | 1986-01-01 | Rhone Poulenc Agrochimie | Herbicides of the sulfon imide-type with an aminomethylphosphonic group. |
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 |
IL129840A0 (en) * | 1998-02-12 | 2000-02-29 | Monsanto Co | 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 |
ATE310009T1 (en) | 2000-05-22 | 2005-12-15 | Monsanto Technology Llc | REACTION SYSTEMS FOR THE PRODUCTION OF N-(PHOSPHONOMETHYL)GLYZINE COMPOUNDS |
US8703639B2 (en) * | 2004-09-15 | 2014-04-22 | Monsanto Technology Llc | Oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
AU2006232348B2 (en) | 2005-04-01 | 2010-11-25 | Monsanto Technology Llc | 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 DD DD175538A patent/DD110503A5/xx unknown
- 1973-12-20 FR FR7345835A patent/FR2211468B1/fr not_active Expired
- 1973-12-20 CH CH1796673A patent/CH592105A5/xx not_active IP Right Cessation
- 1973-12-20 BG BG025303A patent/BG24411A3/en unknown
- 1973-12-20 HU HUMO891A patent/HU168961B/hu not_active IP Right Cessation
- 1973-12-20 DK DK694073AA patent/DK134559B/en not_active IP Right Cessation
- 1973-12-20 SE SE7317193A patent/SE403379B/en unknown
- 1973-12-20 IT IT3554/73A patent/IT1001432B/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
- 1973-12-20 YU YU3305/73A patent/YU37363B/en unknown
- 1973-12-20 AR AR251626A patent/AR216882A1/en active
- 1973-12-20 GB GB5908373A patent/GB1428499A/en not_active Expired
- 1973-12-20 IE IE2308/73A patent/IE38667B1/en unknown
- 1973-12-20 JP JP48142934A patent/JPS5111094B2/ja not_active Expired
- 1973-12-20 PL PL1973167559A patent/PL94988B1/pl unknown
Also Published As
Publication number | Publication date |
---|---|
DK134559C (en) | 1977-05-09 |
BR7309442D0 (en) | 1974-08-29 |
NL163218B (en) | 1980-03-17 |
US3835000A (en) | 1974-09-10 |
AU6385173A (en) | 1975-06-26 |
CH592105A5 (en) | 1977-10-14 |
DE2363634A1 (en) | 1974-06-27 |
EG11507A (en) | 1977-08-15 |
NL163218C (en) | 1980-08-15 |
DE2363634B2 (en) | 1977-06-02 |
ES421614A1 (en) | 1976-10-16 |
HU168961B (en) | 1976-08-28 |
CA1001992A (en) | 1976-12-21 |
IE38667B1 (en) | 1978-05-10 |
IE38667L (en) | 1974-06-21 |
RO64474A (en) | 1979-05-15 |
NL7317370A (en) | 1974-06-25 |
IT1001432B (en) | 1976-04-20 |
DD110503A5 (en) | 1974-12-20 |
YU330573A (en) | 1983-04-27 |
SE403379B (en) | 1978-08-14 |
FR2211468B1 (en) | 1976-05-07 |
JPS5111094B2 (en) | 1976-04-08 |
DK134559B (en) | 1976-11-29 |
JPS4988827A (en) | 1974-08-24 |
PH10205A (en) | 1976-09-27 |
GB1428499A (en) | 1976-03-17 |
AR216882A1 (en) | 1980-02-15 |
PL94988B1 (en) | 1977-09-30 |
BG24411A3 (en) | 1978-02-10 |
IL43880A0 (en) | 1974-03-14 |
YU37363B (en) | 1984-08-31 |
FR2211468A1 (en) | 1974-07-19 |
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