CA2203553C - Process for the manufacture of n-phosphonomethylglycine - Google Patents
Process for the manufacture of n-phosphonomethylglycine Download PDFInfo
- Publication number
- CA2203553C CA2203553C CA002203553A CA2203553A CA2203553C CA 2203553 C CA2203553 C CA 2203553C CA 002203553 A CA002203553 A CA 002203553A CA 2203553 A CA2203553 A CA 2203553A CA 2203553 C CA2203553 C CA 2203553C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- phosphonomethylglycine
- alkali metal
- stage
- formaldehyde
- 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
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000008569 process Effects 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 109
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims abstract description 64
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 38
- -1 alkali metal cyanide Chemical class 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 12
- 239000011707 mineral Substances 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 3
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 14
- 238000006460 hydrolysis reaction Methods 0.000 claims description 14
- 239000011734 sodium Substances 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 4
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000005562 Glyphosate Substances 0.000 abstract 1
- 229940097068 glyphosate Drugs 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 47
- 239000000243 solution Substances 0.000 description 29
- 238000007792 addition Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 14
- 239000000376 reactant Substances 0.000 description 13
- 235000010755 mineral Nutrition 0.000 description 9
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 description 6
- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000000750 progressive effect Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical group O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- VFCAUIASFOLMEI-UHFFFAOYSA-L disodium;phosphonatomethanamine Chemical compound [Na+].[Na+].NCP([O-])([O-])=O VFCAUIASFOLMEI-UHFFFAOYSA-L 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000004698 iron complex Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical class C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material 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
-
- 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)]
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9423254.3 | 1994-11-16 | ||
| GB9423254A GB9423254D0 (en) | 1994-11-16 | 1994-11-16 | Process |
| PCT/GB1995/002573 WO1996015135A1 (en) | 1994-11-16 | 1995-11-02 | Process for the manufacture of n-phosphonomethylglycine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2203553A1 CA2203553A1 (en) | 1996-05-23 |
| CA2203553C true CA2203553C (en) | 2005-01-18 |
Family
ID=10764573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002203553A Expired - Fee Related CA2203553C (en) | 1994-11-16 | 1995-11-02 | Process for the manufacture of n-phosphonomethylglycine |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5679843A (h) |
| EP (1) | EP0792277B1 (h) |
| JP (1) | JP3576169B2 (h) |
| KR (1) | KR100362553B1 (h) |
| CN (1) | CN1061982C (h) |
| AR (1) | AR000087A1 (h) |
| AT (1) | ATE181554T1 (h) |
| AU (1) | AU697316B2 (h) |
| BG (1) | BG101523A (h) |
| BR (1) | BR9509691A (h) |
| CA (1) | CA2203553C (h) |
| CZ (1) | CZ149097A3 (h) |
| DE (1) | DE69510466T2 (h) |
| DK (1) | DK0792277T3 (h) |
| ES (1) | ES2133819T3 (h) |
| FI (1) | FI972065L (h) |
| GB (1) | GB9423254D0 (h) |
| GR (1) | GR3030456T3 (h) |
| HU (1) | HU217301B (h) |
| IL (1) | IL115793A (h) |
| MA (1) | MA23714A1 (h) |
| MY (1) | MY112939A (h) |
| NO (1) | NO972240D0 (h) |
| NZ (1) | NZ294891A (h) |
| PL (1) | PL187068B1 (h) |
| SK (1) | SK61297A3 (h) |
| TW (1) | TW296385B (h) |
| WO (1) | WO1996015135A1 (h) |
| ZA (1) | ZA959527B (h) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9515265D0 (en) * | 1995-07-25 | 1995-09-20 | Zeneca Ltd | Chemical process |
| DE19629870A1 (de) * | 1996-07-24 | 1998-01-29 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von N-Phosphonomethylglycin |
| US5948937A (en) * | 1996-09-12 | 1999-09-07 | Monsanto Company | Method for producing N-phosphonomethylglycine and its salts |
| CA2265724C (en) * | 1996-09-12 | 2005-11-15 | Monsanto Company | Method for producing n-phosphonomethylglycine and its salts |
| BR9714197A (pt) * | 1996-12-30 | 2000-03-28 | Monsanto Co | Derivados de ciano fosfonatos e processo para sua preparação |
| WO1998029424A1 (en) * | 1996-12-30 | 1998-07-09 | Monsanto Company | Preparation of cyanophosphonates from phosphates and cyanide |
| AU723149B2 (en) * | 1996-12-30 | 2000-08-17 | Monsanto Company | Cyanophosphorus compounds and their preparation |
| US5859278A (en) * | 1996-12-30 | 1999-01-12 | Monsanto Company | Method for preparing cyanophosphonate derivatives from pyrophosphate or polyphosphate esters and cyanide |
| JP2001507664A (ja) * | 1996-12-30 | 2001-06-12 | モンサント・カンパニー | 無水リン酸およびシアン化物からシアノホスホネート誘導体を調製する方法 |
| JP2001507695A (ja) * | 1996-12-30 | 2001-06-12 | モンサント・カンパニー | シアノホスホネート誘導体の水素化を経由するアミノメチルホスホネート誘導体の調製方法 |
| BR9714116A (pt) * | 1996-12-30 | 2000-03-21 | Monsatto Company | Hidrogenação de derivados de cianofosfonato na presença de um derivado de glicina |
| EP1135398A1 (en) | 1998-12-03 | 2001-09-26 | Monsanto Technology LLC | Cyanophosphonamides and method for preparation |
| WO2001048234A1 (fr) * | 1999-12-27 | 2001-07-05 | Asahi Kasei Kabushiki Kaisha | Procede de production de glycine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4221583A (en) * | 1978-12-22 | 1980-09-09 | Monsanto Company | N-Phosphonomethylglycinonitrile and certain derivatives thereof |
| PL156933B1 (pl) * | 1988-02-16 | 1992-04-30 | Politechnika Wroclawska | Sposób wytwarzania N-(1-fosfonoalkilo) glicyn, zwlaszcza N-(fosfonometylo) glicyny PL |
| CA2053362A1 (en) * | 1990-10-15 | 1992-04-16 | Druce K. Crump | Preparation of aminonitriles |
| JP2525977B2 (ja) * | 1991-10-17 | 1996-08-21 | 昭和電工株式会社 | Ｎ−アシルアミノメチルホスホン酸の製造法 |
| GB9307234D0 (en) * | 1993-04-07 | 1993-06-02 | Zeneca Ltd | Process |
-
1994
- 1994-11-16 GB GB9423254A patent/GB9423254D0/en active Pending
-
1995
- 1995-10-26 TW TW084111300A patent/TW296385B/zh not_active IP Right Cessation
- 1995-10-27 IL IL11579395A patent/IL115793A/xx not_active IP Right Cessation
- 1995-11-02 JP JP51581396A patent/JP3576169B2/ja not_active Expired - Lifetime
- 1995-11-02 FI FI972065A patent/FI972065L/fi unknown
- 1995-11-02 CN CN95196267A patent/CN1061982C/zh not_active Expired - Fee Related
- 1995-11-02 CZ CZ971490A patent/CZ149097A3/cs unknown
- 1995-11-02 BR BR9509691A patent/BR9509691A/pt not_active IP Right Cessation
- 1995-11-02 NZ NZ294891A patent/NZ294891A/xx unknown
- 1995-11-02 DK DK95936013T patent/DK0792277T3/da active
- 1995-11-02 PL PL95321158A patent/PL187068B1/pl not_active IP Right Cessation
- 1995-11-02 KR KR1019970703259A patent/KR100362553B1/ko not_active Expired - Fee Related
- 1995-11-02 AT AT95936013T patent/ATE181554T1/de not_active IP Right Cessation
- 1995-11-02 EP EP95936013A patent/EP0792277B1/en not_active Expired - Lifetime
- 1995-11-02 AU AU38104/95A patent/AU697316B2/en not_active Ceased
- 1995-11-02 HU HU9702181A patent/HU217301B/hu not_active IP Right Cessation
- 1995-11-02 SK SK612-97A patent/SK61297A3/sk unknown
- 1995-11-02 CA CA002203553A patent/CA2203553C/en not_active Expired - Fee Related
- 1995-11-02 DE DE69510466T patent/DE69510466T2/de not_active Expired - Fee Related
- 1995-11-02 ES ES95936013T patent/ES2133819T3/es not_active Expired - Lifetime
- 1995-11-02 WO PCT/GB1995/002573 patent/WO1996015135A1/en active IP Right Grant
- 1995-11-07 AR AR33414295A patent/AR000087A1/es unknown
- 1995-11-07 MA MA24059A patent/MA23714A1/fr unknown
- 1995-11-09 ZA ZA959527A patent/ZA959527B/xx unknown
- 1995-11-13 US US08/556,319 patent/US5679843A/en not_active Expired - Lifetime
- 1995-11-16 MY MYPI95003493A patent/MY112939A/en unknown
-
1997
- 1997-05-15 NO NO972240A patent/NO972240D0/no unknown
- 1997-05-29 BG BG101523A patent/BG101523A/xx unknown
-
1999
- 1999-06-24 GR GR990401362T patent/GR3030456T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |