EP1165572A1 - Verfahren zur herstellung von n-phosphonomethyliminodiessigsäure - Google Patents
Verfahren zur herstellung von n-phosphonomethyliminodiessigsäureInfo
- Publication number
- EP1165572A1 EP1165572A1 EP00926772A EP00926772A EP1165572A1 EP 1165572 A1 EP1165572 A1 EP 1165572A1 EP 00926772 A EP00926772 A EP 00926772A EP 00926772 A EP00926772 A EP 00926772A EP 1165572 A1 EP1165572 A1 EP 1165572A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- sep
- reaction
- iminodiacetic acid
- ida
- 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.)
- Withdrawn
Links
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 title abstract description 56
- 238000000034 method Methods 0.000 title abstract description 32
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 abstract description 58
- 238000006243 chemical reaction Methods 0.000 abstract description 55
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 30
- 239000002253 acid Substances 0.000 abstract description 22
- 239000000243 solution Substances 0.000 abstract description 21
- 239000012452 mother liquor Substances 0.000 abstract description 20
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 19
- 239000011707 mineral Substances 0.000 abstract description 19
- 238000006386 neutralization reaction Methods 0.000 abstract description 16
- 239000007864 aqueous solution Substances 0.000 abstract description 15
- 238000001914 filtration Methods 0.000 abstract description 11
- 239000002699 waste material Substances 0.000 abstract description 10
- 239000006227 byproduct Substances 0.000 abstract description 8
- 238000000926 separation method Methods 0.000 abstract description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 7
- 239000011734 sodium Substances 0.000 abstract description 7
- 238000004064 recycling Methods 0.000 abstract description 6
- 229910052708 sodium Inorganic materials 0.000 abstract description 6
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract description 5
- 230000001681 protective effect Effects 0.000 abstract description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 39
- 239000000706 filtrate Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 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 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000012535 impurity Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FUXALCGRSSRCQE-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-7-yl)ethanamine Chemical compound NCCC1=CC=CC2=C1OCC2 FUXALCGRSSRCQE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- XEQIERZCOHTONL-UHFFFAOYSA-L dipotassium;2-(carboxylatomethylamino)acetate Chemical compound [K+].[K+].[O-]C(=O)CNCC([O-])=O XEQIERZCOHTONL-UHFFFAOYSA-L 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010626 work up procedure 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
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 |
|---|---|---|---|
| DE19914375 | 1999-03-30 | ||
| DE19914375A DE19914375A1 (de) | 1999-03-30 | 1999-03-30 | Verfahren zur Herstellung von N-Phosphonomethyliminodiessigsäure |
| PCT/EP2000/002762 WO2000059915A1 (de) | 1999-03-30 | 2000-03-29 | Verfahren zur herstellung von n-phosphonomethyliminodiessigsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1165572A1 true EP1165572A1 (de) | 2002-01-02 |
Family
ID=7902923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP00926772A Withdrawn EP1165572A1 (de) | 1999-03-30 | 2000-03-29 | Verfahren zur herstellung von n-phosphonomethyliminodiessigsäure |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1165572A1 (zh) |
| AR (1) | AR023123A1 (zh) |
| AU (1) | AU4540500A (zh) |
| DE (1) | DE19914375A1 (zh) |
| HK (1) | HK1042903A1 (zh) |
| WO (1) | WO2000059915A1 (zh) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR029508A1 (es) * | 2000-04-14 | 2003-07-02 | Dow Agrosciences Llc | Proceso para remover y recuperar cloruro de sodio de los efluentes de desecho provenientes de los procesos de fabricacion del acido n-fosfometiliminodiacetico (pmida) |
| CN101208348A (zh) | 2005-04-25 | 2008-06-25 | 孟山都技术公司 | 改变n-(膦酰甲基)亚氨基二乙酸的晶体尺寸分布以改进过滤和产物质量 |
| US9315528B2 (en) | 2009-10-27 | 2016-04-19 | Straitmark Holding Ag | Method for the manufacture of phosphonoalkyl iminodiacetic acid |
| CN102706986B (zh) * | 2010-11-22 | 2014-01-22 | 重庆紫光化工股份有限公司 | 一种双甘膦母液中亚氨基二乙酸成分的分析方法 |
| CN102033066B (zh) * | 2010-11-22 | 2013-02-13 | 重庆紫光化工股份有限公司 | 一种双甘膦母液成分的分析方法 |
| CN102706985B (zh) * | 2010-11-22 | 2014-01-22 | 重庆紫光化工股份有限公司 | 一种双甘膦母液中双甘膦成分的分析方法 |
| CN102706987B (zh) * | 2010-11-22 | 2014-01-22 | 重庆紫光化工股份有限公司 | 一种双甘膦母液成分的分析方法 |
| PL2875037T3 (pl) | 2012-07-17 | 2017-06-30 | Straitmark Holding Ag | Sposób syntezy N-(fosfonometylo)glicyny |
| EP2875036A1 (en) | 2012-07-17 | 2015-05-27 | Straitmark Holding AG | Method for the synthesis of aminoalkylenephosphonic acid |
| BR112015000993B1 (pt) | 2012-07-17 | 2020-04-28 | Monsanto Technology Llc | método para a síntese de um ácido alfaaminoalquileno fosfônico ou de um éster do mesmo |
| RU2015103314A (ru) | 2012-07-17 | 2016-09-10 | Страйтмарк Холдинг Аг | Способ синтеза N-фосфонометилиминодиуксусной кислоты |
| CN104098602B (zh) * | 2014-07-08 | 2016-08-24 | 重庆紫光化工股份有限公司 | 一种双甘膦的节能清洁生产方法 |
| CN104447863A (zh) * | 2014-12-09 | 2015-03-25 | 安徽工业大学 | 一种双甘膦的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU205944B (en) * | 1988-02-08 | 1992-07-28 | Nitrokemia Ipartelepek | Process for producing n-phosphono-methyl-imino-diacetic acid |
| GB9300641D0 (en) * | 1993-01-14 | 1993-03-03 | Zeneca Ltd | Process |
| US5312973A (en) * | 1993-03-25 | 1994-05-17 | Finchimica S.P.A. | Process for producing n-phosphono-methyl-imino-diacetic acid |
| CA2223287C (en) * | 1995-06-07 | 2001-05-15 | Monsanto Company | Process for preparing n-phosphonomethyliminodiacetic acid |
-
1999
- 1999-03-30 DE DE19914375A patent/DE19914375A1/de not_active Withdrawn
-
2000
- 2000-03-22 AR ARP000101270A patent/AR023123A1/es unknown
- 2000-03-29 WO PCT/EP2000/002762 patent/WO2000059915A1/de not_active Application Discontinuation
- 2000-03-29 AU AU45405/00A patent/AU4540500A/en not_active Abandoned
- 2000-03-29 EP EP00926772A patent/EP1165572A1/de not_active Withdrawn
-
2002
- 2002-06-24 HK HK02104671.6A patent/HK1042903A1/zh unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO0059915A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000059915A1 (de) | 2000-10-12 |
| HK1042903A1 (zh) | 2002-08-30 |
| AU4540500A (en) | 2000-10-23 |
| DE19914375A1 (de) | 2000-10-05 |
| AR023123A1 (es) | 2002-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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| 17P | Request for examination filed |
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| 17Q | First examination report despatched |
Effective date: 20020125 |
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| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: DEGUSSA AG |
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| GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
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| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: MONSANTO COMPANY |
|
| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: MONSANTO TECHNOLOGY LLC |
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| STAA | Information on the status of an ep patent application or granted ep patent |
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| 18D | Application deemed to be withdrawn |
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