CS221969B2 - Method of making the n-phosphonomrthylglycine - Google Patents
Method of making the n-phosphonomrthylglycine Download PDFInfo
- Publication number
- CS221969B2 CS221969B2 CS803211A CS321180A CS221969B2 CS 221969 B2 CS221969 B2 CS 221969B2 CS 803211 A CS803211 A CS 803211A CS 321180 A CS321180 A CS 321180A CS 221969 B2 CS221969 B2 CS 221969B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- reaction
- acid
- catalyst
- oxygen
- water
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 43
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 230000008569 process Effects 0.000 claims abstract description 22
- 230000003647 oxidation Effects 0.000 claims abstract description 16
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 16
- 239000001301 oxygen Substances 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 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 abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007789 gas Substances 0.000 claims abstract description 5
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 239000000725 suspension Substances 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 16
- 239000012736 aqueous medium Substances 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 64
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 26
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000002045 lasting effect Effects 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SGVDYFNFBJGOHB-UHFFFAOYSA-N 2-[methyl(phosphonomethyl)amino]acetic acid Chemical compound OC(=O)CN(C)CP(O)(O)=O SGVDYFNFBJGOHB-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- -1 N-phosphonomethylglycine ester Chemical class 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241001311547 Patina Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HSMRCPIZVMDSHN-UHFFFAOYSA-N methylaminomethylphosphonic acid Chemical compound CNCP(O)(O)=O HSMRCPIZVMDSHN-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79MA3146A HU184168B (en) | 1979-05-11 | 1979-05-11 | Process for producing n-bracket-phosphono-methyl-bracket closed-glycine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS221969B2 true CS221969B2 (en) | 1983-04-29 |
Family
ID=10999085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS803211A CS221969B2 (en) | 1979-05-11 | 1980-05-07 | Method of making the n-phosphonomrthylglycine |
Country Status (35)
| Country | Link |
|---|---|
| EP (1) | EP0019445B2 (ru) |
| JP (1) | JPS5618994A (ru) |
| AT (2) | AT380687B (ru) |
| AU (1) | AU542716B2 (ru) |
| BE (1) | BE883222A (ru) |
| BG (1) | BG33276A3 (ru) |
| BR (1) | BR8002886A (ru) |
| CA (1) | CA1155138A (ru) |
| CH (1) | CH642379A5 (ru) |
| CS (1) | CS221969B2 (ru) |
| DD (1) | DD150614A5 (ru) |
| DE (2) | DE3017518C2 (ru) |
| DK (1) | DK147144C (ru) |
| EG (1) | EG14671A (ru) |
| ES (1) | ES8104312A1 (ru) |
| FI (1) | FI68242C (ru) |
| FR (1) | FR2456115B1 (ru) |
| GB (1) | GB2049697B (ru) |
| GR (1) | GR68515B (ru) |
| HU (1) | HU184168B (ru) |
| IE (1) | IE50347B1 (ru) |
| IL (1) | IL59903A (ru) |
| IN (1) | IN151845B (ru) |
| IT (1) | IT1148860B (ru) |
| LU (1) | LU82380A1 (ru) |
| NL (1) | NL8002674A (ru) |
| NO (1) | NO152416C (ru) |
| NZ (1) | NZ193573A (ru) |
| PL (1) | PL122706B1 (ru) |
| PT (1) | PT71151A (ru) |
| SE (1) | SE447901B (ru) |
| SU (1) | SU927121A3 (ru) |
| TR (1) | TR21105A (ru) |
| YU (1) | YU42213B (ru) |
| ZA (1) | ZA802456B (ru) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4442041A (en) * | 1982-06-30 | 1984-04-10 | Stauffer Chemical Company | Method for preparation of N-phosphonomethylglycine |
| IL68716A (en) * | 1983-05-17 | 1987-03-31 | Geshuri Lab Ltd | Process for producing n-phosphonomethylglycine |
| US4579689A (en) * | 1985-02-11 | 1986-04-01 | Monsanto Company | Oxidation with coated catalyst |
| US4582650A (en) * | 1985-02-11 | 1986-04-15 | Monsanto Company | Oxidation with encapsulated co-catalyst |
| US4696772A (en) * | 1985-02-28 | 1987-09-29 | Monsanto Company | Amine oxidation using carbon catalyst having oxides removed from surface |
| US4657705A (en) * | 1985-09-23 | 1987-04-14 | Monsanto Company | Process for the preparation of N-substituted aminomethylphosphonic acids |
| US4853159A (en) * | 1987-10-26 | 1989-08-01 | Monsanto Company | Process for producing N-phosphonomethylglycine |
| HU200780B (en) * | 1988-02-08 | 1990-08-28 | Nitrokemia Ipartelepek | Process for producing n-phosphonomethyl iminodiacetic acid from double salt of iminodiacetic acid |
| US4952723A (en) * | 1989-07-31 | 1990-08-28 | Monsanto Company | Process for producing N-phosphonomethylglycine |
| US5095140A (en) * | 1990-06-25 | 1992-03-10 | Monsanto Company | Peroxide process for producing N-phosphonomethylglycine |
| US5061820A (en) * | 1990-10-22 | 1991-10-29 | Monsanto Company | Process for producing N-phosphonomethylgylcine |
| SI9400449A (en) * | 1994-12-20 | 1996-06-30 | Pinus D D | Process for preparing N-phosphonomethyl glycin |
| US6417133B1 (en) | 1998-02-25 | 2002-07-09 | Monsanto Technology Llc | Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions |
| EP1198466B1 (de) | 1999-07-23 | 2003-04-02 | Basf Aktiengesellschaft | Verfahren zur herstellung von glyphosate oder eines salzes davon |
| DE60115019T2 (de) | 2000-05-22 | 2006-08-03 | Monsanto Technology Llc. | Reaktionssysteme zur herstellung von n-(phosphonomethyl)glyzin verbindungen |
| US6921834B2 (en) | 2002-05-22 | 2005-07-26 | Dow Agrosciences Llc | Continuous process for preparing N-phosphonomethyl glycine |
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969398A (en) * | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
-
1979
- 1979-05-11 HU HU79MA3146A patent/HU184168B/hu unknown
-
1980
- 1980-04-21 CH CH304780A patent/CH642379A5/de not_active IP Right Cessation
- 1980-04-22 LU LU82380A patent/LU82380A1/de unknown
- 1980-04-23 IL IL59903A patent/IL59903A/xx unknown
- 1980-04-23 ZA ZA00802457A patent/ZA802456B/xx unknown
- 1980-04-28 PT PT71151A patent/PT71151A/pt not_active IP Right Cessation
- 1980-04-28 FI FI801363A patent/FI68242C/fi not_active IP Right Cessation
- 1980-04-30 NZ NZ193573A patent/NZ193573A/xx unknown
- 1980-04-30 EG EG269/80A patent/EG14671A/xx active
- 1980-05-03 GR GR61848A patent/GR68515B/el unknown
- 1980-05-05 BG BG8047626A patent/BG33276A3/xx unknown
- 1980-05-06 IN IN525/CAL/80A patent/IN151845B/en unknown
- 1980-05-06 SE SE8003396A patent/SE447901B/sv not_active IP Right Cessation
- 1980-05-07 DE DE3017518A patent/DE3017518C2/de not_active Expired
- 1980-05-07 CS CS803211A patent/CS221969B2/cs unknown
- 1980-05-07 IE IE944/80A patent/IE50347B1/en unknown
- 1980-05-07 SU SU802917349A patent/SU927121A3/ru active
- 1980-05-08 ES ES491296A patent/ES8104312A1/es not_active Expired
- 1980-05-08 PL PL1980224125A patent/PL122706B1/pl unknown
- 1980-05-08 DD DD80220946A patent/DD150614A5/de not_active IP Right Cessation
- 1980-05-09 NL NL8002674A patent/NL8002674A/nl not_active Application Discontinuation
- 1980-05-09 YU YU1245/80A patent/YU42213B/xx unknown
- 1980-05-09 AT AT0247280A patent/AT380687B/de not_active IP Right Cessation
- 1980-05-09 BE BE0/200555A patent/BE883222A/fr not_active IP Right Cessation
- 1980-05-09 NO NO801381A patent/NO152416C/no unknown
- 1980-05-09 AU AU58285/80A patent/AU542716B2/en not_active Expired
- 1980-05-09 DK DK204080A patent/DK147144C/da not_active IP Right Cessation
- 1980-05-09 JP JP6164280A patent/JPS5618994A/ja active Granted
- 1980-05-09 BR BR8002886A patent/BR8002886A/pt unknown
- 1980-05-09 FR FR8010482A patent/FR2456115B1/fr not_active Expired
- 1980-05-09 CA CA000351661A patent/CA1155138A/en not_active Expired
- 1980-05-09 IT IT21972/80A patent/IT1148860B/it active
- 1980-05-12 AT AT80301549T patent/ATE3428T1/de not_active IP Right Cessation
- 1980-05-12 EP EP80301549A patent/EP0019445B2/en not_active Expired
- 1980-05-12 DE DE8080301549T patent/DE3063274D1/de not_active Expired
- 1980-05-12 GB GB8015644A patent/GB2049697B/en not_active Expired
-
1983
- 1983-05-08 TR TR21105A patent/TR21105A/xx unknown
Also Published As
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