DE19909200C1 - Verfahren zur Herstellung von N-Phosphonomethyliminodiessigsäure - Google Patents
Verfahren zur Herstellung von N-PhosphonomethyliminodiessigsäureInfo
- Publication number
- DE19909200C1 DE19909200C1 DE1999109200 DE19909200A DE19909200C1 DE 19909200 C1 DE19909200 C1 DE 19909200C1 DE 1999109200 DE1999109200 DE 1999109200 DE 19909200 A DE19909200 A DE 19909200A DE 19909200 C1 DE19909200 C1 DE 19909200C1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- iminodiacetic acid
- formaldehyde
- iminodiacetic
- phosphorous
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 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 claims abstract description 36
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 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 title claims abstract description 21
- 230000001681 protective effect Effects 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000002253 acid Substances 0.000 claims abstract description 12
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 10
- 239000011707 mineral Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 description 13
- XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical group OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000006452 multicomponent reaction Methods 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001291 vacuum drying 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)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1999109200 DE19909200C1 (de) | 1999-03-03 | 1999-03-03 | Verfahren zur Herstellung von N-Phosphonomethyliminodiessigsäure |
| ARP000100924 AR022810A1 (es) | 1999-03-03 | 2000-03-02 | UN PROCEDIMIENTO PARA LA FABRICACIoN DE ÁCIDO N-FOSFONOMETILIMINODIACETICO. |
| AU35538/00A AU3553800A (en) | 1999-03-03 | 2000-03-03 | Method for producing n-phosphonomethyl iminodiacetic acid |
| PCT/EP2000/001896 WO2000052014A2 (fr) | 1999-03-03 | 2000-03-03 | Procede pour la production d'acide n-phosphonomethyl iminodiacetique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1999109200 DE19909200C1 (de) | 1999-03-03 | 1999-03-03 | Verfahren zur Herstellung von N-Phosphonomethyliminodiessigsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19909200C1 true DE19909200C1 (de) | 2000-03-09 |
Family
ID=7899498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1999109200 Expired - Fee Related DE19909200C1 (de) | 1999-03-03 | 1999-03-03 | Verfahren zur Herstellung von N-Phosphonomethyliminodiessigsäure |
Country Status (4)
| Country | Link |
|---|---|
| AR (1) | AR022810A1 (fr) |
| AU (1) | AU3553800A (fr) |
| DE (1) | DE19909200C1 (fr) |
| WO (1) | WO2000052014A2 (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100400543C (zh) * | 2006-09-08 | 2008-07-09 | 四川贝尔实业有限责任公司 | 亚氨基二乙腈水解制备双甘膦的方法 |
| WO2014012986A1 (fr) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Procédé de synthèse d'acide n-phosphonométhyliminodiacétique |
| 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 |
| US10464958B2 (en) | 2012-07-17 | 2019-11-05 | Monsanto Technology Llc | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994015939A1 (fr) * | 1993-01-14 | 1994-07-21 | Zeneca Limited | Procede de production d'acide n-phosphonomethyliminodiacetique |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2154588B (en) * | 1984-02-20 | 1987-10-07 | Sunlead Chemical Industry Co L | A process for preparation of n-phosphonomethyl glycine |
| HU205944B (en) * | 1988-02-08 | 1992-07-28 | Nitrokemia Ipartelepek | Process for producing n-phosphono-methyl-imino-diacetic acid |
| US5312973A (en) * | 1993-03-25 | 1994-05-17 | Finchimica S.P.A. | Process for producing n-phosphono-methyl-imino-diacetic acid |
| US6118022A (en) * | 1998-09-08 | 2000-09-12 | Hampshire Chemical Corp. | Synthesis of phosphonomethyliminodiacetic acid with reduced effluent |
-
1999
- 1999-03-03 DE DE1999109200 patent/DE19909200C1/de not_active Expired - Fee Related
-
2000
- 2000-03-02 AR ARP000100924 patent/AR022810A1/es active IP Right Grant
- 2000-03-03 WO PCT/EP2000/001896 patent/WO2000052014A2/fr active Application Filing
- 2000-03-03 AU AU35538/00A patent/AU3553800A/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994015939A1 (fr) * | 1993-01-14 | 1994-07-21 | Zeneca Limited | Procede de production d'acide n-phosphonomethyliminodiacetique |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100400543C (zh) * | 2006-09-08 | 2008-07-09 | 四川贝尔实业有限责任公司 | 亚氨基二乙腈水解制备双甘膦的方法 |
| WO2014012986A1 (fr) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Procédé de synthèse d'acide n-phosphonométhyliminodiacétique |
| 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 |
|---|---|
| AU3553800A (en) | 2000-09-21 |
| AR022810A1 (es) | 2002-09-04 |
| WO2000052014A3 (fr) | 2002-02-14 |
| WO2000052014A2 (fr) | 2000-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: DEGUSSA AG, 40474 DUESSELDORF, DE |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: MONSANTO TECHNOLOGY LLC, ST. LOUIS, MO., US |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: WEICKMANN & WEICKMANN, 81679 MUENCHEN |
|
| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee |
Effective date: 20111001 |