CN1066152C - 制备n－膦酰基甲基甘氨酸的方法 - Google Patents
制备n－膦酰基甲基甘氨酸的方法 Download PDFInfo
- Publication number
- CN1066152C CN1066152C CN96193655A CN96193655A CN1066152C CN 1066152 C CN1066152 C CN 1066152C CN 96193655 A CN96193655 A CN 96193655A CN 96193655 A CN96193655 A CN 96193655A CN 1066152 C CN1066152 C CN 1066152C
- Authority
- CN
- China
- Prior art keywords
- pmida
- gac
- mole
- pmg
- hydrogen peroxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 81
- 230000008569 process Effects 0.000 title claims abstract description 9
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 138
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000010438 heat treatment Methods 0.000 claims description 41
- 238000013019 agitation Methods 0.000 claims 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 abstract description 102
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 92
- 238000006243 chemical reaction Methods 0.000 description 50
- 238000003756 stirring Methods 0.000 description 36
- 239000000203 mixture Substances 0.000 description 33
- 238000000926 separation method Methods 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 11
- 230000008025 crystallization Effects 0.000 description 11
- 239000003643 water by type Substances 0.000 description 11
- 239000003610 charcoal Substances 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 238000001640 fractional crystallisation Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000003245 coal Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 230000005587 bubbling Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 229910000765 intermetallic Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003077 lignite Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 for example Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- BKUQKIUBBFUVBN-UHFFFAOYSA-N 2-(carboxymethylamino)acetic acid;sodium Chemical compound [Na].OC(=O)CNCC(O)=O BKUQKIUBBFUVBN-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002802 bituminous coal Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood 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)]
- C07F9/40—Esters thereof
-
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4600595 | 1995-03-07 | ||
| JP46005/1995 | 1995-03-07 | ||
| JP46005/95 | 1995-03-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1183100A CN1183100A (zh) | 1998-05-27 |
| CN1066152C true CN1066152C (zh) | 2001-05-23 |
Family
ID=12734963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96193655A Expired - Fee Related CN1066152C (zh) | 1995-03-07 | 1996-03-07 | 制备n－膦酰基甲基甘氨酸的方法 |
Country Status (6)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962729A (en) * | 1998-05-14 | 1999-10-05 | Calgon Carbon Corporation | Method for the manufacture of N-phosphonomethylglycine from N-phosphonomethyliminodiacetic acid using a catalytic carbon |
| CA2380177A1 (en) | 1999-07-23 | 2001-02-01 | Basf Aktiengesellschaft | Method of producing glyphosate or a salt thereof |
| DE19938622C2 (de) * | 1999-08-14 | 2002-10-02 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von N-(Phosphonomethyl)glycin |
| CN101311183B (zh) * | 2000-05-22 | 2011-08-31 | 孟山都技术有限责任公司 | 制备n-(膦酰基甲基)甘氨酸化合物的反应系统 |
| CN1221558C (zh) * | 2000-05-22 | 2005-10-05 | 孟山都技术有限责任公司 | 制备n－(膦酰基甲基)甘氨酸化合物的反应系统 |
| CN1301259C (zh) * | 2004-01-16 | 2007-02-21 | 广东琪田农药化工有限公司 | 由双甘膦制备草甘膦的方法 |
| CN104585228B (zh) * | 2005-03-04 | 2017-05-24 | 孟山都技术公司 | 减轻用除草剂草甘膦制剂处理的草甘膦耐受性转基因棉花植物内的坏死 |
| CN101092429B (zh) * | 2006-06-23 | 2010-08-11 | 北京紫光英力化工技术有限公司 | 一种催化氧化法制备草甘膦的方法 |
| CN101092428B (zh) * | 2006-06-23 | 2011-04-06 | 北京紫光英力化工技术有限公司 | 一种双甘膦空气氧化制备草甘膦的新工艺 |
| CN101508701B (zh) * | 2008-12-10 | 2012-09-05 | 上海泰禾(集团)有限公司 | 一种活性碳作催化剂氧气氧化双甘膦制备草甘膦的方法 |
| US9359390B2 (en) | 2010-03-31 | 2016-06-07 | Kuraray Chemical Co., Ltd. | Activated carbon and use therefor |
| KR101246278B1 (ko) * | 2012-09-18 | 2013-03-22 | 주식회사 천보 | 이미노디아세트산의 합성방법 |
| CN104829649A (zh) * | 2015-05-05 | 2015-08-12 | 安徽省益农化工有限公司 | 采用双甘膦为原料生产草甘膦的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969398A (en) * | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| EP0088180A1 (en) * | 1982-03-08 | 1983-09-14 | Geshuri Laboratories Ltd. | N-phosphonomethylglycine derivatives |
| EP0162035A2 (en) * | 1984-05-10 | 1985-11-21 | Monsanto Company | Process for the selective production of secondary and primary amines |
| EP0980334A2 (en) * | 1997-05-09 | 2000-02-23 | The Procter & Gamble Company | Flexible, collapsible, self-supporting storage bags and containers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL66137A (en) * | 1982-06-25 | 1986-03-31 | Geshuri Lab Ltd | Process for producing n-phosphonomethylglycine isopropyl amine salt and herbicidal compositions prepared therewith |
| JPS60246328A (ja) * | 1984-05-10 | 1985-12-06 | モンサント コンパニー | 第２アミン及び第１アミンの選択的製造方法 |
-
1996
- 1996-03-05 TW TW085102684A patent/TW322481B/zh active
- 1996-03-07 AU AU48893/96A patent/AU4889396A/en not_active Abandoned
- 1996-03-07 KR KR1019970706115A patent/KR19980702708A/ko active IP Right Grant
- 1996-03-07 WO PCT/JP1996/000550 patent/WO1996027602A1/ja active IP Right Grant
- 1996-03-07 CN CN96193655A patent/CN1066152C/zh not_active Expired - Fee Related
-
1998
- 1998-11-09 HK HK98111858A patent/HK1017360A1/xx not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969398A (en) * | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| EP0088180A1 (en) * | 1982-03-08 | 1983-09-14 | Geshuri Laboratories Ltd. | N-phosphonomethylglycine derivatives |
| EP0162035A2 (en) * | 1984-05-10 | 1985-11-21 | Monsanto Company | Process for the selective production of secondary and primary amines |
| EP0980334A2 (en) * | 1997-05-09 | 2000-02-23 | The Procter & Gamble Company | Flexible, collapsible, self-supporting storage bags and containers |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4889396A (en) | 1996-09-23 |
| HK1017360A1 (en) | 1999-11-19 |
| KR19980702708A (ko) | 1998-08-05 |
| CN1183100A (zh) | 1998-05-27 |
| WO1996027602A1 (fr) | 1996-09-12 |
| TW322481B (US20020095090A1-20020718-M00002.png) | 1997-12-11 |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |