FI68242C - Foerfarande foer framstaellning av n-fosfonmetyl-glycin - Google Patents
Foerfarande foer framstaellning av n-fosfonmetyl-glycin Download PDFInfo
- Publication number
- FI68242C FI68242C FI801363A FI801363A FI68242C FI 68242 C FI68242 C FI 68242C FI 801363 A FI801363 A FI 801363A FI 801363 A FI801363 A FI 801363A FI 68242 C FI68242 C FI 68242C
- Authority
- FI
- Finland
- Prior art keywords
- reaction
- catalyst
- oxidation
- acid
- phosphonomethylglycine
- Prior art date
Links
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 36
- 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 33
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 20
- 230000003647 oxidation Effects 0.000 claims abstract description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000007789 gas Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000725 suspension Substances 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012467 final product Substances 0.000 description 5
- 229910052697 platinum Inorganic materials 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
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- -1 N-phosphonomethylglycine triester Chemical class 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010438 heat treatment Methods 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
- 239000000203 mixture Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ATMCYVLYKYHSJF-UHFFFAOYSA-N 2-(phosphonomethylimino)acetic acid Chemical compound OC(=O)C=NCP(O)(O)=O ATMCYVLYKYHSJF-UHFFFAOYSA-N 0.000 description 1
- 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
- ZFOAAGMZOKROSR-UHFFFAOYSA-N CCC(CC=NCP(=O)(O)O)C(=O)O Chemical compound CCC(CC=NCP(=O)(O)O)C(=O)O ZFOAAGMZOKROSR-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 101100166829 Mus musculus Cenpk gene Proteins 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940097068 glyphosate Drugs 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
- 239000004009 herbicide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- WYOBJKKCIPAIQO-UHFFFAOYSA-N methanamine;methylphosphonic acid Chemical compound NC.CP(O)(O)=O WYOBJKKCIPAIQO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical class [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000080 wetting agent Substances 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 (2)
| 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 |
| HUMA003146 | 1979-05-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI801363A FI801363A (fi) | 1980-11-12 |
| FI68242B FI68242B (fi) | 1985-04-30 |
| FI68242C true FI68242C (fi) | 1985-08-12 |
Family
ID=10999085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI801363A FI68242C (fi) | 1979-05-11 | 1980-04-28 | Foerfarande foer framstaellning av n-fosfonmetyl-glycin |
Country Status (35)
| Country | Link |
|---|---|
| EP (1) | EP0019445B2 (xx) |
| JP (1) | JPS5618994A (xx) |
| AT (2) | AT380687B (xx) |
| AU (1) | AU542716B2 (xx) |
| BE (1) | BE883222A (xx) |
| BG (1) | BG33276A3 (xx) |
| BR (1) | BR8002886A (xx) |
| CA (1) | CA1155138A (xx) |
| CH (1) | CH642379A5 (xx) |
| CS (1) | CS221969B2 (xx) |
| DD (1) | DD150614A5 (xx) |
| DE (2) | DE3017518C2 (xx) |
| DK (1) | DK147144C (xx) |
| EG (1) | EG14671A (xx) |
| ES (1) | ES8104312A1 (xx) |
| FI (1) | FI68242C (xx) |
| FR (1) | FR2456115B1 (xx) |
| GB (1) | GB2049697B (xx) |
| GR (1) | GR68515B (xx) |
| HU (1) | HU184168B (xx) |
| IE (1) | IE50347B1 (xx) |
| IL (1) | IL59903A (xx) |
| IN (1) | IN151845B (xx) |
| IT (1) | IT1148860B (xx) |
| LU (1) | LU82380A1 (xx) |
| NL (1) | NL8002674A (xx) |
| NO (1) | NO152416C (xx) |
| NZ (1) | NZ193573A (xx) |
| PL (1) | PL122706B1 (xx) |
| PT (1) | PT71151A (xx) |
| SE (1) | SE447901B (xx) |
| SU (1) | SU927121A3 (xx) |
| TR (1) | TR21105A (xx) |
| YU (1) | YU42213B (xx) |
| ZA (1) | ZA802456B (xx) |
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 |
| PT1198466E (pt) * | 1999-07-23 | 2003-08-29 | Basf Ag | Processo para producao de glifosatos ou um dos seus sais |
| WO2001092272A2 (en) | 2000-05-22 | 2001-12-06 | Monsanto Technology Llc | Reaction systems for making n-(phosphonomethyl)glycine compounds |
| US6921834B2 (en) | 2002-05-22 | 2005-07-26 | Dow Agrosciences Llc | Continuous process for preparing N-phosphonomethyl glycine |
| US8703639B2 (en) | 2004-09-15 | 2014-04-22 | 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 FI FI801363A patent/FI68242C/fi not_active IP Right Cessation
- 1980-04-28 PT PT71151A patent/PT71151A/pt not_active IP Right Cessation
- 1980-04-30 EG EG269/80A patent/EG14671A/xx active
- 1980-04-30 NZ NZ193573A patent/NZ193573A/xx unknown
- 1980-05-03 GR GR61848A patent/GR68515B/el unknown
- 1980-05-05 BG BG8047626A patent/BG33276A3/xx unknown
- 1980-05-06 SE SE8003396A patent/SE447901B/sv not_active IP Right Cessation
- 1980-05-06 IN IN525/CAL/80A patent/IN151845B/en unknown
- 1980-05-07 CS CS803211A patent/CS221969B2/cs unknown
- 1980-05-07 IE IE944/80A patent/IE50347B1/en unknown
- 1980-05-07 DE DE3017518A patent/DE3017518C2/de not_active Expired
- 1980-05-07 SU SU802917349A patent/SU927121A3/ru active
- 1980-05-08 PL PL1980224125A patent/PL122706B1/pl unknown
- 1980-05-08 ES ES491296A patent/ES8104312A1/es not_active Expired
- 1980-05-08 DD DD80220946A patent/DD150614A5/de not_active IP Right Cessation
- 1980-05-09 CA CA000351661A patent/CA1155138A/en not_active Expired
- 1980-05-09 BR BR8002886A patent/BR8002886A/pt unknown
- 1980-05-09 DK DK204080A patent/DK147144C/da not_active IP Right Cessation
- 1980-05-09 IT IT21972/80A patent/IT1148860B/it active
- 1980-05-09 AT AT0247280A patent/AT380687B/de not_active IP Right Cessation
- 1980-05-09 AU AU58285/80A patent/AU542716B2/en not_active Expired
- 1980-05-09 JP JP6164280A patent/JPS5618994A/ja active Granted
- 1980-05-09 YU YU1245/80A patent/YU42213B/xx unknown
- 1980-05-09 BE BE0/200555A patent/BE883222A/fr not_active IP Right Cessation
- 1980-05-09 FR FR8010482A patent/FR2456115B1/fr not_active Expired
- 1980-05-09 NO NO801381A patent/NO152416C/no unknown
- 1980-05-09 NL NL8002674A patent/NL8002674A/nl not_active Application Discontinuation
- 1980-05-12 DE DE8080301549T patent/DE3063274D1/de not_active Expired
- 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 GB GB8015644A patent/GB2049697B/en not_active Expired
-
1983
- 1983-05-08 TR TR21105A patent/TR21105A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: NITROKéMIA IPARTELEPEK |