CS8904851A3 - Process for preparing novel n-sulfomethyl glycinates - Google Patents
Process for preparing novel n-sulfomethyl glycinates Download PDFInfo
- Publication number
- CS8904851A3 CS8904851A3 CS894851A CS485189A CS8904851A3 CS 8904851 A3 CS8904851 A3 CS 8904851A3 CS 894851 A CS894851 A CS 894851A CS 485189 A CS485189 A CS 485189A CS 8904851 A3 CS8904851 A3 CS 8904851A3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- glycine
- mol
- formaldehyde
- sulfur dioxide
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 28
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000004471 Glycine Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 10
- IWTOEMVHPMYHPE-UHFFFAOYSA-N 2-(sulfomethylamino)acetic acid Chemical compound OC(=O)CNCS(O)(=O)=O IWTOEMVHPMYHPE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 229960004279 formaldehyde Drugs 0.000 claims 2
- 235000019256 formaldehyde Nutrition 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000004009 herbicide Substances 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 abstract description 4
- 239000005562 Glyphosate Substances 0.000 abstract description 3
- 229940097068 glyphosate Drugs 0.000 abstract description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 abstract description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 saturated aliphatic ethers Chemical class 0.000 description 3
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HHOSMYBYIHNXNO-UHFFFAOYSA-N 2,2,5-trimethylhexane Chemical compound CC(C)CCC(C)(C)C HHOSMYBYIHNXNO-UHFFFAOYSA-N 0.000 description 1
- RODFSMLWTZVONC-UHFFFAOYSA-N 2-[ethyl(sulfomethyl)amino]acetic acid Chemical compound C(C)N(CC(=O)O)CS(=O)(=O)O RODFSMLWTZVONC-UHFFFAOYSA-N 0.000 description 1
- UNDXPKDBFOOQFC-UHFFFAOYSA-N 4-[2-nitro-4-(trifluoromethyl)phenyl]morpholine Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCOCC1 UNDXPKDBFOOQFC-UHFFFAOYSA-N 0.000 description 1
- ZMRQAYPQBJNFIT-UHFFFAOYSA-N 4-methylpentan-2-one;1-phenylethanone Chemical compound CC(C)CC(C)=O.CC(=O)C1=CC=CC=C1 ZMRQAYPQBJNFIT-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
-
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Soil Working Implements (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS897168A CS8907168A3 (en) | 1988-08-18 | 1989-08-17 | Process for preparing glyphosphates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8811141A FR2635522B1 (fr) | 1988-08-18 | 1988-08-18 | N-sulfonomethylglycinate procede de preparation, utilisation dans la preparation d'herbicides de type glyphosate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS8904851A3 true CS8904851A3 (en) | 1992-01-15 |
| CS275034B2 CS275034B2 (en) | 1992-01-15 |
Family
ID=9369474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS894851A CS275034B2 (en) | 1988-08-18 | 1989-08-17 | Method of new n-sulphoglycinates production |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5117043A (xx) |
| EP (1) | EP0356353B1 (xx) |
| JP (1) | JPH02101059A (xx) |
| KR (1) | KR900003114A (xx) |
| CN (2) | CN1040362A (xx) |
| AT (1) | ATE82256T1 (xx) |
| AU (1) | AU622212B2 (xx) |
| BG (2) | BG50724A3 (xx) |
| BR (1) | BR8904242A (xx) |
| CS (1) | CS275034B2 (xx) |
| DD (1) | DD283992A5 (xx) |
| DE (1) | DE68903455T2 (xx) |
| DK (1) | DK405389A (xx) |
| FI (1) | FI893866A (xx) |
| FR (1) | FR2635522B1 (xx) |
| GR (1) | GR3006300T3 (xx) |
| HK (1) | HK21693A (xx) |
| HU (1) | HUT51599A (xx) |
| IL (1) | IL91344A0 (xx) |
| MA (1) | MA21612A1 (xx) |
| NZ (1) | NZ230344A (xx) |
| OA (1) | OA09426A (xx) |
| PL (1) | PL284406A1 (xx) |
| PT (1) | PT91483B (xx) |
| RO (1) | RO103740B1 (xx) |
| TR (1) | TR24158A (xx) |
| YU (1) | YU161389A (xx) |
| ZA (1) | ZA896293B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69415829T2 (de) * | 1993-11-18 | 1999-05-20 | Mobil Oil Corp., Fairfax, Va. | Katalysatorzusammensetzung für die copolymerisation von ethylen |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
| US3950402A (en) * | 1972-05-31 | 1976-04-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| US3835000A (en) * | 1972-12-21 | 1974-09-10 | Monsanto Co | Electrolytic process for producing n-phosphonomethyl glycine |
| US3868407A (en) * | 1973-11-21 | 1975-02-25 | Monsanto Co | Carboxyalkyl esters of n-phosphonomethyl glycine |
| JPS5854381B2 (ja) * | 1975-02-17 | 1983-12-05 | 富士写真フイルム株式会社 | カラ−カクサンテンシヤヨウシヤシンザイリヨウ |
| NL7713959A (nl) * | 1976-12-20 | 1978-06-22 | Monsanto Co | Werkwijze voor het bereiden van n-fosfono- methylglycinezouten. |
| DE3068779D1 (en) * | 1979-05-15 | 1984-09-06 | Ici Plc | Pesticidal formulations |
-
1988
- 1988-08-18 FR FR8811141A patent/FR2635522B1/fr not_active Expired - Lifetime
-
1989
- 1989-08-01 US US07/388,570 patent/US5117043A/en not_active Expired - Fee Related
- 1989-08-07 CN CN89105602A patent/CN1040362A/zh active Pending
- 1989-08-10 DE DE8989420302T patent/DE68903455T2/de not_active Expired - Fee Related
- 1989-08-10 AT AT89420302T patent/ATE82256T1/de not_active IP Right Cessation
- 1989-08-10 EP EP89420302A patent/EP0356353B1/fr not_active Expired - Lifetime
- 1989-08-11 KR KR1019890011468A patent/KR900003114A/ko not_active Application Discontinuation
- 1989-08-14 TR TR89/0833A patent/TR24158A/xx unknown
- 1989-08-15 JP JP1210538A patent/JPH02101059A/ja active Pending
- 1989-08-15 MA MA21865A patent/MA21612A1/fr unknown
- 1989-08-16 FI FI893866A patent/FI893866A/fi not_active Application Discontinuation
- 1989-08-16 RO RO141304A patent/RO103740B1/ro unknown
- 1989-08-16 PL PL28440689A patent/PL284406A1/xx unknown
- 1989-08-17 CS CS894851A patent/CS275034B2/cs unknown
- 1989-08-17 ZA ZA896293A patent/ZA896293B/xx unknown
- 1989-08-17 BG BG089562A patent/BG50724A3/xx unknown
- 1989-08-17 NZ NZ230344A patent/NZ230344A/en unknown
- 1989-08-17 AU AU40028/89A patent/AU622212B2/en not_active Ceased
- 1989-08-17 YU YU01613/89A patent/YU161389A/xx unknown
- 1989-08-17 IL IL91344A patent/IL91344A0/xx unknown
- 1989-08-17 BG BG095878A patent/BG60104B2/bg unknown
- 1989-08-17 DK DK405389A patent/DK405389A/da not_active Application Discontinuation
- 1989-08-18 DD DD89331920A patent/DD283992A5/de not_active IP Right Cessation
- 1989-08-18 HU HU894243A patent/HUT51599A/hu unknown
- 1989-08-18 BR BR898904242A patent/BR8904242A/pt unknown
- 1989-08-18 OA OA59625A patent/OA09426A/xx unknown
- 1989-08-18 PT PT91483A patent/PT91483B/pt not_active IP Right Cessation
-
1992
- 1992-04-17 CN CN92102843A patent/CN1064868A/zh active Pending
- 1992-11-20 GR GR920400199T patent/GR3006300T3/el unknown
-
1993
- 1993-03-11 HK HK216/93A patent/HK21693A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4519316B2 (ja) | グルホシネートおよびそのための中間体の製造法 | |
| US5324855A (en) | Preparation of N-acylaminomethylphosphonic acid | |
| EP0112580A1 (en) | Process for preparing phosphonomethylated amino acids | |
| CA2193234A1 (en) | Process for preparing n-phosphonomethylamino carboxylic acids | |
| USRE35389E (en) | Process for the preparation of N-phosphonomethylglycine | |
| CN104812763A (zh) | 用于合成n-(膦酰基甲基)甘氨酸的方法 | |
| CZ286135B6 (cs) | Způsob přípravy distyrylbifenylových sloučenin | |
| CS8904851A3 (en) | Process for preparing novel n-sulfomethyl glycinates | |
| US5679842A (en) | Process for the preparation of aminomethanephosphonic acid and aminomethylphosphinic acids | |
| JPH05194337A (ja) | α−アミノ酸、ｐ−ヒドロキシフェニルグリシン、アミノ酸エステルおよびアミノ酸アミドの製造方法 | |
| JP3111076B2 (ja) | アミノメタンホスホン酸およびアミノメチル―ホスフィン酸の製造方法 | |
| RU2260010C2 (ru) | Способ получения n-фосфонометилглицина и промежуточный продукт для его получения | |
| CA2089652C (en) | Preparation of acylaminomethanephosphonic acids and acylaminomethanephosphinic acids | |
| IE912921A1 (en) | Process for the preparation of aminomethylphosphonic acid¹and aminomethylphosphinic acids from N-hydroxymethylamides | |
| Kisanga et al. | The synthesis of 2, 6, 7‐trioxa‐1, 4‐diphosphabicyclo [2.2. 2] octane revisited: the synthesis of 2, 6, 7‐triphenyl‐2N, 6N, 7N‐triaza‐1, 4‐diphosphabicyclo [2.2. 2] octane and the synthesis of 1λ5‐phosphiranol | |
| US5187292A (en) | N-sulfomethylglycinate, use in the preparation of herbicides of the glyphosate type | |
| US4746755A (en) | Preparation of hydrantoic acids and hydantoins | |
| EP0153261B1 (fr) | Esters de la famille de la N-phosphonométhylglycine et leur utilisation pour la préparation d'herbicides connus | |
| US4504673A (en) | Preparation of tartronic esters | |
| KR900003411B1 (ko) | N-포스포노메틸 글리신의 제조방법 | |
| RU2152397C1 (ru) | Способы получения n-гидроксиалкиламинометилфосфоновой кислоты, n-фосфонометиламинокарбоновой кислоты и n-фосфонометилглицина или их солей | |
| SU1016292A1 (ru) | Способ получени @ -дифенилфосфинокарбоновых кислот | |
| US4645852A (en) | One step conversion of epoxyalkanes to alkyl esters of alkyl and aryl sulfonic acids | |
| SU589756A1 (ru) | Способ получени солей перфторалкилфосфиновых кислот | |
| KR840001484B1 (ko) | 세린 유도체의 제조방법 |