CS272248B2 - Method of phosphonomethylliminodacetic acid's and c 1-4 carboxyl acid's chloride simultaneous preparation - Google Patents
Method of phosphonomethylliminodacetic acid's and c 1-4 carboxyl acid's chloride simultaneous preparation Download PDFInfo
- Publication number
- CS272248B2 CS272248B2 CS89842A CS84289A CS272248B2 CS 272248 B2 CS272248 B2 CS 272248B2 CS 89842 A CS89842 A CS 89842A CS 84289 A CS84289 A CS 84289A CS 272248 B2 CS272248 B2 CS 272248B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- carboxylic acid
- phosphorous
- chloride
- trichloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 239000002253 acid Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 27
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 26
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 23
- 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 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 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 description 7
- 239000008098 formaldehyde solution Substances 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 7
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- KKHJQZVEUKJURX-UHFFFAOYSA-N 2-(carboxymethylamino)acetic acid;hydrochloride Chemical compound Cl.OC(=O)CNCC(O)=O KKHJQZVEUKJURX-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- -1 carboxylic acid chlorides Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis 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
- 239000005562 Glyphosate Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- 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)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU88561A HU205944B (en) | 1988-02-08 | 1988-02-08 | Process for producing n-phosphono-methyl-imino-diacetic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS84289A2 CS84289A2 (en) | 1990-03-14 |
| CS272248B2 true CS272248B2 (en) | 1991-01-15 |
Family
ID=10950166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS89842A CS272248B2 (en) | 1988-02-08 | 1989-02-08 | Method of phosphonomethylliminodacetic acid's and c 1-4 carboxyl acid's chloride simultaneous preparation |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPH01228995A (it) |
| CN (1) | CN1035294A (it) |
| AU (1) | AU2886089A (it) |
| BE (1) | BE1002135A5 (it) |
| BR (1) | BR8900622A (it) |
| CS (1) | CS272248B2 (it) |
| DE (1) | DE3903716A1 (it) |
| DK (1) | DK39689A (it) |
| ES (1) | ES2010126A6 (it) |
| FR (1) | FR2626884B1 (it) |
| GB (1) | GB2215721B (it) |
| GR (1) | GR890100071A (it) |
| HU (1) | HU205944B (it) |
| IT (1) | IT1228299B (it) |
| NL (1) | NL8900279A (it) |
| NZ (1) | NZ227702A (it) |
| PL (1) | PL277611A1 (it) |
| PT (1) | PT89577B (it) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5312973A (en) * | 1993-03-25 | 1994-05-17 | Finchimica S.P.A. | Process for producing n-phosphono-methyl-imino-diacetic acid |
| DE19909200C1 (de) * | 1999-03-03 | 2000-03-09 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von N-Phosphonomethyliminodiessigsäure |
| DE19914375A1 (de) * | 1999-03-30 | 2000-10-05 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von N-Phosphonomethyliminodiessigsäure |
| WO2014012987A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of aminoalkylenephosphonic acid |
| WO2014012991A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of n-(phosphonomethyl)glycine |
| IN2015DN01082A (it) | 2012-07-17 | 2015-06-26 | Straitmark Holding Ag | |
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE251806C (it) * | 1900-01-01 | |||
| HU177486B (en) * | 1978-04-11 | 1981-10-28 | Nitrokemia Ipartelepek | Process for preparing phosphonic acid derivatives |
| US4724103A (en) * | 1984-02-27 | 1988-02-09 | Monsanto Company | Process for preparing N,N-diacetic acid aminomethylenephosphonic acid |
-
1988
- 1988-02-08 HU HU88561A patent/HU205944B/hu not_active IP Right Cessation
-
1989
- 1989-01-24 NZ NZ227702A patent/NZ227702A/xx unknown
- 1989-01-27 DK DK039689A patent/DK39689A/da not_active Application Discontinuation
- 1989-01-27 AU AU28860/89A patent/AU2886089A/en not_active Abandoned
- 1989-01-27 GB GB8901807A patent/GB2215721B/en not_active Expired - Fee Related
- 1989-01-31 PT PT89577A patent/PT89577B/pt active IP Right Grant
- 1989-02-01 FR FR898901267A patent/FR2626884B1/fr not_active Expired - Fee Related
- 1989-02-03 BE BE8900120A patent/BE1002135A5/fr not_active IP Right Cessation
- 1989-02-03 BR BR898900622A patent/BR8900622A/pt unknown
- 1989-02-03 CN CN89100721.0A patent/CN1035294A/zh active Pending
- 1989-02-06 NL NL8900279A patent/NL8900279A/nl not_active Application Discontinuation
- 1989-02-06 GR GR890100071A patent/GR890100071A/el unknown
- 1989-02-07 ES ES8900422A patent/ES2010126A6/es not_active Expired
- 1989-02-07 IT IT8919339A patent/IT1228299B/it active
- 1989-02-07 JP JP1028530A patent/JPH01228995A/ja active Pending
- 1989-02-07 PL PL27761189A patent/PL277611A1/xx unknown
- 1989-02-08 CS CS89842A patent/CS272248B2/cs unknown
- 1989-02-08 DE DE3903716A patent/DE3903716A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT1228299B (it) | 1991-06-07 |
| GB8901807D0 (en) | 1989-03-15 |
| NL8900279A (nl) | 1989-09-01 |
| DK39689D0 (da) | 1989-01-27 |
| AU2886089A (en) | 1989-08-10 |
| BE1002135A5 (fr) | 1990-07-24 |
| IT8919339A0 (it) | 1989-02-07 |
| FR2626884B1 (fr) | 1991-11-08 |
| DE3903716A1 (de) | 1989-08-17 |
| DK39689A (da) | 1989-08-09 |
| BR8900622A (pt) | 1989-10-10 |
| JPH01228995A (ja) | 1989-09-12 |
| GB2215721A (en) | 1989-09-27 |
| HU205944B (en) | 1992-07-28 |
| HUT49359A (en) | 1989-09-28 |
| GR890100071A (el) | 1994-03-31 |
| FR2626884A1 (fr) | 1989-08-11 |
| CN1035294A (zh) | 1989-09-06 |
| GB2215721B (en) | 1991-06-26 |
| PT89577B (pt) | 1994-01-31 |
| PL277611A1 (en) | 1989-09-18 |
| PT89577A (pt) | 1989-10-04 |
| CS84289A2 (en) | 1990-03-14 |
| ES2010126A6 (es) | 1989-10-16 |
| NZ227702A (en) | 1990-10-26 |
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