KR840006489A - N-포스포노 메틸글리신의 제법 - Google Patents
N-포스포노 메틸글리신의 제법 Download PDFInfo
- Publication number
- KR840006489A KR840006489A KR1019830004903A KR830004903A KR840006489A KR 840006489 A KR840006489 A KR 840006489A KR 1019830004903 A KR1019830004903 A KR 1019830004903A KR 830004903 A KR830004903 A KR 830004903A KR 840006489 A KR840006489 A KR 840006489A
- Authority
- KR
- South Korea
- Prior art keywords
- phosphonomethylglycine
- acid
- anhydride
- group
- hydantoin
- Prior art date
Links
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 229940091173 hydantoin Drugs 0.000 claims 4
- -1 phosphonomethyl Chemical group 0.000 claims 4
- 229930040373 Paraformaldehyde Chemical class 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 229920002866 paraformaldehyde Chemical class 0.000 claims 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 3
- MZQQHYDUINOMDG-UHFFFAOYSA-N 3-methylimidazolidine-2,4-dione Chemical compound CN1C(=O)CNC1=O MZQQHYDUINOMDG-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 2
- IUPSCXDOKZWYRB-UHFFFAOYSA-N 1,2,3$l^{2}-triphosphirene Chemical compound [P]1P=P1 IUPSCXDOKZWYRB-UHFFFAOYSA-N 0.000 claims 1
- QUIQKYAAGXIAFF-UHFFFAOYSA-N 2-(phosphonoamino)acetic acid Chemical compound OC(=O)CNP(O)(O)=O QUIQKYAAGXIAFF-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Natural products CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 150000001469 hydantoins Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- (a) 하기 구조식의 화합물인 히단토인 또는 3- 치환히단토인과 파라포름알데히드를 1-(히드록시메틸) 유도체를 포함하는 중간 생성물의 혼합체를 생성하기에 충분한 기간 동안 및 온도하에 저분자량의 카르복실산의 존재하에서, 반응시키고 ; (b)상기 반응혼합체에 대하여, (i) 3염화인 및 3취화인으로 구성되는 그루우프에서 선택된 치환인 화합물이거나 또는 (ii) 무수초산, 무수프로피온산, 무수낙산, 또는 유사한 비대칭 무수물로 구성되는 그루우프에서 선택된 인산 및 무수카르복실산을 첨가함에 의하여 상기 1-(히드록시메틸) 유도체를 1-포스포노메틸히단오인으로 변환시키고, 반응완료를 일으키기에 충분한 온도 및 기간동안 상기반응을 계속함에 의하여 1-(포스포노메틸)유도체를 생성하여 ; (c)상기 1-(포스포노메틸) 유도체를 알칼리금속 또는 알칼리 토수산화물로 구성되는 그루우프로부터 선택된 염기의 수용액에 의하여, 가수분해시킴에 의하여 N-포스포노 메틸글리신의 염을 생성하고, 그리고, (d) 상기 염을 강산에 의하여 중화함으로써 N-포스포노메틸글리신을 생성시키는 공정으로 이루어지는 N-포스포노메틸글리신의 제법.식중, R은 수소, 1∼10개의 탄소원자를 가진 아릴, 6∼12개의 탄소원자를 아릴, 알킬 그루우프 이 1∼10개의 탄소원자를 가진 알킬카르보닐, 아릴 그루우프 이 6∼12개의 탄소원자를 가진 아릴카르보닐로 구설된 그루우프로부터 선택된다.
- 치환인 화합물은 3염화인 및 3취화인으로 구성되는 그루우프로부터 선택되는 특허청구의 범위 1기재의 N-포스포노메틸글리신의 제법.
- 전분자량의 카르복실산의 초신, 프로파논산 및 부탄산으로 구성되는 N-포스포노메틸글리신의 제법.
- 히단토인, 파라포름알데히드 및 치환인 화합물은 약 화학량논적 양으로 사용되며, 그리고 카르복신산은 과잉량으로 사용되어지는 N-포스포노메틸글리신의 제법.
- 히단토인 이 3-메틸 히단토인으로 이루어지는 N-포스포노메틸글리신의 제법.
- 파라포름알데히드는 히단토인에 대한 과잉량으로 사용되는 N-포스포노글리신의 제법.
- 산은 염화수소산, 황산, 취화수소산 및 옥화수소산으로 구성되는 그루우프로부터 선택되는 N-포스포노메틸글리신의 제법.
- 공정단계(c)의 염기는 알칼리금속 또는 알칼리로 수산화물로 구성되는 그루우프로부터 선택되는 N-포스포노메틸글리신의 제법.
- 공정단계 (a)에서 염화아세틸 또는 무수초산을 기타 반응물과 함께 첨가되어지는 N-포스포노메틸글리신의 제법.
- 공정단계(b)는 반응혼합물에 대하여 인산 및 무수인산, 무수프로피온산, 무수부티릴산 또는 혼합물로 구성되는 그루우프에서 선택되는 무수물을 첨가함으로서 이루어지는 N-포스포노메틸글리신의 제법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43512282A | 1982-10-18 | 1982-10-18 | |
| US435,122 | 1982-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840006489A true KR840006489A (ko) | 1984-11-30 |
Family
ID=23727074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830004903A KR840006489A (ko) | 1982-10-18 | 1983-10-17 | N-포스포노 메틸글리신의 제법 |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0107464B1 (ko) |
| JP (1) | JPS5989694A (ko) |
| KR (1) | KR840006489A (ko) |
| AT (1) | ATE17357T1 (ko) |
| AU (1) | AU559033B2 (ko) |
| CA (1) | CA1205817A (ko) |
| CS (1) | CS242887B2 (ko) |
| DD (1) | DD215555A5 (ko) |
| DE (1) | DE3361801D1 (ko) |
| DK (1) | DK467083A (ko) |
| ES (1) | ES526547A0 (ko) |
| FI (1) | FI73694C (ko) |
| IL (1) | IL69983A (ko) |
| NO (1) | NO833774L (ko) |
| NZ (1) | NZ205983A (ko) |
| PL (1) | PL140413B1 (ko) |
| RO (1) | RO87968A (ko) |
| YU (1) | YU208983A (ko) |
| ZA (1) | ZA837693B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4804499A (en) * | 1985-09-23 | 1989-02-14 | Monsanto Company | Process for the preparation of N-substituted aminomethylphosphonic acids |
| US4694082A (en) * | 1985-09-23 | 1987-09-15 | Monsanto Company | Compound 1,4-diisopropyl-2,5-diketopiperazine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES444490A1 (es) * | 1975-01-16 | 1977-09-16 | Chinoin Gyogyszer Es Vegyeszet | Procedimiento para la fabricacion de n-fosfono-metilglicina y sus intermedios. |
| US4400330A (en) * | 1982-07-29 | 1983-08-23 | Stauffer Chemical Company | Method for preparation of N-phosphonomethylglycine |
-
1983
- 1983-10-11 DK DK467083A patent/DK467083A/da not_active Application Discontinuation
- 1983-10-13 RO RO83112324A patent/RO87968A/ro unknown
- 1983-10-17 NO NO833774A patent/NO833774L/no unknown
- 1983-10-17 AT AT83306278T patent/ATE17357T1/de not_active IP Right Cessation
- 1983-10-17 KR KR1019830004903A patent/KR840006489A/ko not_active IP Right Cessation
- 1983-10-17 ZA ZA837693A patent/ZA837693B/xx unknown
- 1983-10-17 IL IL69983A patent/IL69983A/xx unknown
- 1983-10-17 NZ NZ205983A patent/NZ205983A/en unknown
- 1983-10-17 CS CS837562A patent/CS242887B2/cs unknown
- 1983-10-17 FI FI833760A patent/FI73694C/fi not_active IP Right Cessation
- 1983-10-17 PL PL1983244184A patent/PL140413B1/pl unknown
- 1983-10-17 AU AU20224/83A patent/AU559033B2/en not_active Ceased
- 1983-10-17 DE DE8383306278T patent/DE3361801D1/de not_active Expired
- 1983-10-17 CA CA000439087A patent/CA1205817A/en not_active Expired
- 1983-10-17 EP EP83306278A patent/EP0107464B1/en not_active Expired
- 1983-10-18 DD DD83255747A patent/DD215555A5/de unknown
- 1983-10-18 JP JP58193559A patent/JPS5989694A/ja active Granted
- 1983-10-18 YU YU02089/83A patent/YU208983A/xx unknown
- 1983-10-18 ES ES526547A patent/ES526547A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| RO87968A (ro) | 1985-12-20 |
| DD215555A5 (de) | 1984-11-14 |
| ATE17357T1 (de) | 1986-01-15 |
| DK467083A (da) | 1984-04-19 |
| NZ205983A (en) | 1986-10-08 |
| IL69983A (en) | 1987-10-20 |
| RO87968B (ro) | 1985-12-01 |
| CS242887B2 (en) | 1986-05-15 |
| JPS5989694A (ja) | 1984-05-23 |
| EP0107464A1 (en) | 1984-05-02 |
| DK467083D0 (da) | 1983-10-11 |
| NO833774L (no) | 1984-04-24 |
| DE3361801D1 (en) | 1986-02-20 |
| YU208983A (en) | 1986-06-30 |
| FI833760A (fi) | 1984-04-19 |
| ZA837693B (en) | 1985-02-27 |
| ES8504830A1 (es) | 1985-04-16 |
| FI833760A0 (fi) | 1983-10-17 |
| AU2022483A (en) | 1984-05-03 |
| PL244184A1 (en) | 1984-09-24 |
| CA1205817A (en) | 1986-06-10 |
| ES526547A0 (es) | 1985-04-16 |
| FI73694B (fi) | 1987-07-31 |
| AU559033B2 (en) | 1987-02-19 |
| FI73694C (fi) | 1987-11-09 |
| CS756283A2 (en) | 1985-08-15 |
| EP0107464B1 (en) | 1986-01-08 |
| JPH0225917B2 (ko) | 1990-06-06 |
| IL69983A0 (en) | 1984-01-31 |
| PL140413B1 (en) | 1987-04-30 |
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