CH620223A5 - Process for the preparation of N-phosphonomethylglycine - Google Patents
Process for the preparation of N-phosphonomethylglycine Download PDFInfo
- Publication number
- CH620223A5 CH620223A5 CH45476A CH45476A CH620223A5 CH 620223 A5 CH620223 A5 CH 620223A5 CH 45476 A CH45476 A CH 45476A CH 45476 A CH45476 A CH 45476A CH 620223 A5 CH620223 A5 CH 620223A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- formula
- diketopiperazine
- phosphonomethyl
- acid
- Prior art date
Links
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 claims abstract description 7
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 7
- 241000196324 Embryophyta Species 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- -1 N- [chloromethyl] -2,5-diketopiperazine Chemical compound 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- 241000508725 Elymus repens Species 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 241000245665 Taraxacum Species 0.000 claims description 4
- 240000008042 Zea mays Species 0.000 claims description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 4
- 235000009973 maize Nutrition 0.000 claims description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- DFRHETNXRZJTGA-UHFFFAOYSA-N 2-(phosphanylmethylamino)acetic acid Chemical compound OC(=O)CNCP DFRHETNXRZJTGA-UHFFFAOYSA-N 0.000 claims description 2
- 244000052363 Cynodon dactylon Species 0.000 claims description 2
- 241000234653 Cyperus Species 0.000 claims description 2
- 240000004585 Dactylis glomerata Species 0.000 claims description 2
- 241000234642 Festuca Species 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- 240000004658 Medicago sativa Species 0.000 claims description 2
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 2
- 241000700159 Rattus Species 0.000 claims description 2
- 240000002439 Sorghum halepense Species 0.000 claims description 2
- 238000009395 breeding Methods 0.000 claims description 2
- 230000001488 breeding effect Effects 0.000 claims description 2
- 230000006196 deacetylation Effects 0.000 claims description 2
- 238000003381 deacetylation reaction Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002420 orchard Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 claims description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 231100000331 toxic Toxicity 0.000 claims description 2
- 230000002588 toxic effect Effects 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- INMIYNYVYZKEMP-UHFFFAOYSA-N (2,3-dioxopiperazin-1-yl)methylphosphonic acid Chemical compound P(=O)(O)(O)CN1C(C(NCC1)=O)=O INMIYNYVYZKEMP-UHFFFAOYSA-N 0.000 description 3
- LYQCDRHQPKKJFN-UHFFFAOYSA-N 1-(chloromethyl)piperazine-2,3-dione Chemical compound ClCN1C(C(NCC1)=O)=O LYQCDRHQPKKJFN-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- UTAKHSUKJYWECQ-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)piperazine-2,3-dione Chemical compound C(C)OP(=O)(OCC)CN1C(C(NCC1)=O)=O UTAKHSUKJYWECQ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- TTYQXKBDHVRUMS-UHFFFAOYSA-N (2,5-dioxopiperazin-1-yl)methylphosphonic acid Chemical compound OP(O)(=O)CN1CC(=O)NCC1=O TTYQXKBDHVRUMS-UHFFFAOYSA-N 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001538 HU170684B (ro) | 1975-01-16 | 1975-01-16 | |
| HUCI001537 HU170683B (ro) | 1975-01-16 | 1975-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH620223A5 true CH620223A5 (en) | 1980-11-14 |
Family
ID=26318405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH45476A CH620223A5 (en) | 1975-01-16 | 1976-01-15 | Process for the preparation of N-phosphonomethylglycine |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5922718B2 (ro) |
| CH (1) | CH620223A5 (ro) |
| DD (1) | DD123192A1 (ro) |
| ES (1) | ES444490A1 (ro) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0102694A1 (en) * | 1982-07-29 | 1984-03-14 | Stauffer Chemical Company | Method for preparation of N-phosphonomethylglycine |
| EP0107464A1 (en) * | 1982-10-18 | 1984-05-02 | Stauffer Chemical Company | Method for preparation of N-phosphonomethylglycine |
| EP0216744A2 (en) * | 1985-09-23 | 1987-04-01 | Monsanto Company | The compound 1,4-diisopropyl-2,5-diketopiperazine |
| WO2014012991A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of n-(phosphonomethyl)glycine |
| US10280189B2 (en) | 2012-07-17 | 2019-05-07 | Monsanto Technology Llc | Method for the synthesis of aminoalkylenephosphonic acid |
| US10364262B2 (en) | 2012-07-17 | 2019-07-30 | Monsanto Technology Llc | Method for the synthesis of N-phosphonomethyliminodiacetic acid |
| US10464958B2 (en) | 2012-07-17 | 2019-11-05 | Monsanto Technology Llc | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
-
1976
- 1976-01-14 ES ES444490A patent/ES444490A1/es not_active Expired
- 1976-01-14 DD DD19080176A patent/DD123192A1/xx unknown
- 1976-01-15 CH CH45476A patent/CH620223A5/de not_active IP Right Cessation
- 1976-01-16 JP JP326676A patent/JPS5922718B2/ja not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0102694A1 (en) * | 1982-07-29 | 1984-03-14 | Stauffer Chemical Company | Method for preparation of N-phosphonomethylglycine |
| EP0107464A1 (en) * | 1982-10-18 | 1984-05-02 | Stauffer Chemical Company | Method for preparation of N-phosphonomethylglycine |
| EP0216744A2 (en) * | 1985-09-23 | 1987-04-01 | Monsanto Company | The compound 1,4-diisopropyl-2,5-diketopiperazine |
| EP0216744A3 (en) * | 1985-09-23 | 1987-09-09 | Monsanto Company | The compound 1,4-diisopropyl-2,5-diketopiperazine |
| WO2014012991A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of n-(phosphonomethyl)glycine |
| CN104812764A (zh) * | 2012-07-17 | 2015-07-29 | 斯特雷特马克控股股份公司 | 用于合成n-(膦酰基甲基)甘氨酸的方法 |
| CN104812764B (zh) * | 2012-07-17 | 2017-06-09 | 斯特雷特马克控股股份公司 | 用于合成n‑(膦酰基甲基)甘氨酸的方法 |
| US9676799B2 (en) | 2012-07-17 | 2017-06-13 | Straitmark Holding Ag | Method for the synthesis of N-(phosphonomethyl)glycine |
| US10280189B2 (en) | 2012-07-17 | 2019-05-07 | Monsanto Technology Llc | Method for the synthesis of aminoalkylenephosphonic acid |
| US10364262B2 (en) | 2012-07-17 | 2019-07-30 | Monsanto Technology Llc | Method for the synthesis of N-phosphonomethyliminodiacetic acid |
| US10464958B2 (en) | 2012-07-17 | 2019-11-05 | Monsanto Technology Llc | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| ES444490A1 (es) | 1977-09-16 |
| JPS5195084A (en) | 1976-08-20 |
| DD123192A1 (ro) | 1976-12-05 |
| JPS5922718B2 (ja) | 1984-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |