KR840000478A - 페녹시벤조산 유도체의 정제방법 - Google Patents
페녹시벤조산 유도체의 정제방법 Download PDFInfo
- Publication number
- KR840000478A KR840000478A KR1019820003347A KR820003347A KR840000478A KR 840000478 A KR840000478 A KR 840000478A KR 1019820003347 A KR1019820003347 A KR 1019820003347A KR 820003347 A KR820003347 A KR 820003347A KR 840000478 A KR840000478 A KR 840000478A
- Authority
- KR
- South Korea
- Prior art keywords
- phenoxy
- benzoic acid
- trifluoromethyl
- chloro
- crude
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 10
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 title claims 8
- 239000008096 xylene Substances 0.000 claims 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- -1 chloro hydrocarbon Chemical class 0.000 claims 2
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical class C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 150000003738 xylenes Chemical class 0.000 claims 2
- YIIKKZDSWBKXEX-UHFFFAOYSA-N 2-chloro-1-(3-methyl-4-nitrophenoxy)-4-(trifluoromethyl)benzene Chemical compound C1=C([N+]([O-])=O)C(C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 YIIKKZDSWBKXEX-UHFFFAOYSA-N 0.000 claims 1
- ZGGSVBWJVIXBHV-UHFFFAOYSA-N 2-chloro-1-(4-nitrophenoxy)-4-(trifluoromethyl)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl ZGGSVBWJVIXBHV-UHFFFAOYSA-N 0.000 claims 1
- PACJZZBTXITTDS-UHFFFAOYSA-N 3-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1[N+]([O-])=O PACJZZBTXITTDS-UHFFFAOYSA-N 0.000 claims 1
- ONKRUAQFUNKYAX-UHFFFAOYSA-N 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 ONKRUAQFUNKYAX-UHFFFAOYSA-N 0.000 claims 1
- ZVGWXYRRDWYHQL-UHFFFAOYSA-N 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2,4-dinitrobenzoic acid Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1[N+]([O-])=O ZVGWXYRRDWYHQL-UHFFFAOYSA-N 0.000 claims 1
- GLBSCOYWQNMMPR-UHFFFAOYSA-N 5-[2-chloro-5-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC=C(C=2)C(F)(F)F)Cl)=C1 GLBSCOYWQNMMPR-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims 1
- 229940100630 metacresol Drugs 0.000 claims 1
- 150000004767 nitrides Chemical class 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 하기식의 페녹시 벤조산 유도체 또는 그의 염을, 바람직하지 못한 이성체 및/또는 부생물을 선택적으로 용해할 수 있는 불활성 용매와 접촉시킨 다음, 바람직하지 못한 이성체 및/또는 부생물의 용액으로 부터 페녹시벤조산 유도체 또는 그의 염을 분리함을 특징으로 하는 1종 이상의 이성체 및/또는 부생물과 하기의 조페녹시벤조산 유도체 또는 그의 염의 혼합물로부터 하기 일반식의 조페녹시벤조산 유도체를 회수하여 정제하는 방법.상기식에서, X1,X2및 X3는 수소, 플루오르, 염소 또는 브롬원자, CF3,OCF2CHZ2(Z는 플루오르, 염소 또는 브롬원자임), OCF3,CN,COOR(R은 저급알킬기임), 페닐, 알콕시, NO2또는 알킬술포닐일 수 있으며, X1,X2및 X3중의 하나 이상이 수소 이외의 의미를 가진다.
- 제1항에 있어서, 페녹시벤조산 유도체가 아시플루오르 펜임을 특징으로 하는 방법.
- 제1 또는 2항에 있어서, 불활성 용매가 탄화수소 또는 클로로 탄화수소임을 특징으로 하는 방법.
- 제3항에 있어서, 탄화수소가 크실렌 또는 크실렌류의 혼합물임을 특징으로 하는 방법.
- 제4항에 있어서, 조 아시플루오르펜의 크실렌/물이 0.35~0.45몰로 사용됨을 특징으로 하는 방법.
- 제 1~5항중의 하나에 있어서, 접촉 온도가 65~122℃임을 특징으로 하는 방법.
- 제 1~6항중의 하나에 있어서, 중간 물질 메타-크레졸레이트를 얻기 위하여 메타-크레졸을 알칼리금속 수산화물과 반응시키고, 이 메타-크레졸레이트를 하기 식의 혼합물과 반응시켜 하기식의 중간물질 페녹시톨루엔 유도체를 얻음으로써 조페녹시 벤조산유도체를 제조함에 있어서, 하기 식의 중간물질 페녹시벤조산 유도체를 얻기 위하여 상기의 중간 물질 페녹시톨루엔 유도체가 산화 촉매 존재하 산소와 반응하고 상기의 조페녹시벤조산 유도체를 얻기 위하여 이 중간 물질을 질화함을 특징으로 하는 방법.식중, X1,X2및 X3는 수소, 플루오르, 염소 또는 브롬원자, CF3,OCF2CHZ2(Z는 플루오르, 염소 또는 브롬 원자임), OCF3,CN,COOR(R은 저급 알킬기임), 페닐, 알콕시, NO2또는 알킬술포닐일 수 있으며, X1,X2및 X3중의 하나 이상이 수소 이외의 의미를 가지며, X4는 할로겐 원자이다.
- 제 7항에 있어서,인 화합물이어서 최종 페녹시벤조산 유도체가 아시플루오르펜임을 특징으로 하는 방법.
- 제8항에 있어서, 조 아시플루오르펜이 3-[2-클로로-5-트리플루오로메틸)-페녹시]-벤조산, 3-[2-클로로-4-(트리플루오로메틸)-페녹시]-벤조산, 4-[2-클로로-4-(트리플루오로메틸)페녹시]니트로벤젠,2-니트로-5-[2클로로-4-(트리플루오로메틸)-페녹시]-톨루엔,4-니트로-5-[2-클로로-4-(트리플루오로메틸-페녹시]-벤조산,2-니트로-5-[2-클로로-5-(트리플루오로메틸)-페녹시]-벤조산, 2-니트로3-[2-클로로-4-(트리플루오로메틸)페녹시]-벤조산 및 2,4-디니트로-5-[2-클로로-4-(트리플루오로메틸)-페녹시]-벤조산으로 이루어진 군으로부터 선택된 1종 이상의 화합물을 포함함을 특징으로 하는 방법.
- 제8 또는 9항에 있어서, 용매가 크실렌 또는 크실렌류의 혼합물임이 특징인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/286,996 US4405805A (en) | 1981-07-27 | 1981-07-27 | Process for recovering and purifying herbicidal phenoxybenzoic acid derivatives |
| US286996 | 1981-07-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840000478A true KR840000478A (ko) | 1984-02-22 |
| KR890001806B1 KR890001806B1 (ko) | 1989-05-23 |
Family
ID=23101031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8203347A KR890001806B1 (ko) | 1981-07-27 | 1982-07-27 | 페녹시벤조산 유도체의 정제방법 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4405805A (ko) |
| JP (1) | JPS5838235A (ko) |
| KR (1) | KR890001806B1 (ko) |
| BE (1) | BE893942A (ko) |
| BR (1) | BR8204352A (ko) |
| CA (1) | CA1203811A (ko) |
| CH (1) | CH652710A5 (ko) |
| DD (1) | DD202423A5 (ko) |
| DE (1) | DE3227846A1 (ko) |
| DK (1) | DK333582A (ko) |
| ES (2) | ES8400386A1 (ko) |
| FR (1) | FR2510102B1 (ko) |
| GB (1) | GB2103214B (ko) |
| HU (1) | HU190694B (ko) |
| IE (1) | IE54596B1 (ko) |
| IL (1) | IL66357A (ko) |
| IT (1) | IT1156314B (ko) |
| LU (1) | LU84297A1 (ko) |
| NL (1) | NL8202995A (ko) |
| PL (1) | PL144334B1 (ko) |
| PT (1) | PT75324B (ko) |
| RO (1) | RO85386B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3129826A1 (de) * | 1981-07-29 | 1983-04-28 | Grillo-Werke Ag, 4100 Duisburg | Zinksalz der hydrolisierten tricarbonsaeure aus diels-alder-addukten von maleinsaeureanhydrid an undecylensaeure, verfahren zur herstellung derselben und ihre verwendung |
| US5446197A (en) * | 1994-10-04 | 1995-08-29 | Basf Corporation | Method of purifying acifluorfen |
| US5910604A (en) * | 1995-09-13 | 1999-06-08 | Zeneca Limited | Purification process |
| US6028219A (en) * | 1995-09-13 | 2000-02-22 | Zeneca Limited | Process for the nitration of diphenylethers |
| GB9518704D0 (en) | 1995-09-13 | 1995-11-15 | Zeneca Ltd | Chemical process |
| GB9518705D0 (en) * | 1995-09-13 | 1995-11-15 | Zeneca Ltd | Chemical process |
| GB9930369D0 (en) * | 1999-12-22 | 2000-02-09 | Zeneca Ltd | Chemical process |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928416A (en) * | 1972-03-14 | 1975-12-23 | Rohm & Haas | Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers |
| US3798276A (en) * | 1972-03-14 | 1974-03-19 | H Bayer | Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers |
| US4046798A (en) * | 1973-02-12 | 1977-09-06 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4'nitrodiphenyl ethers |
| CA1079303A (en) * | 1973-02-12 | 1980-06-10 | Horst O. Bayer | Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers |
| US3979437A (en) * | 1973-09-19 | 1976-09-07 | Mobil Oil Corporation | Substituted phenoxybenzoic acids and derivatives thereof |
| US4031131A (en) * | 1975-09-29 | 1977-06-21 | Rohm And Haas Company | Process for preparing phenoxybenzoic acids |
| DE3071736D1 (en) * | 1979-06-22 | 1986-10-09 | Rhone Poulenc Agrochimie | Process for preparing 2-nitro-5-(substituted-phenoxy) benzoic acids and salts thereof |
| EP0023100B1 (en) * | 1979-07-18 | 1982-11-10 | Imperial Chemical Industries Plc | Herbicidal compositions comprising a diphenyl ether compound in admixture with another herbicide |
-
1981
- 1981-07-27 US US06/286,996 patent/US4405805A/en not_active Expired - Fee Related
-
1982
- 1982-07-02 FR FR8211791A patent/FR2510102B1/fr not_active Expired
- 1982-07-20 IL IL66357A patent/IL66357A/xx unknown
- 1982-07-23 PL PL1982237635A patent/PL144334B1/pl unknown
- 1982-07-23 IT IT22547/82A patent/IT1156314B/it active
- 1982-07-26 HU HU822398A patent/HU190694B/hu not_active IP Right Cessation
- 1982-07-26 LU LU84297A patent/LU84297A1/fr unknown
- 1982-07-26 DK DK333582A patent/DK333582A/da not_active Application Discontinuation
- 1982-07-26 CA CA000408050A patent/CA1203811A/en not_active Expired
- 1982-07-26 BR BR8204352A patent/BR8204352A/pt unknown
- 1982-07-26 ES ES514354A patent/ES8400386A1/es not_active Expired
- 1982-07-26 GB GB08221571A patent/GB2103214B/en not_active Expired
- 1982-07-26 JP JP57130218A patent/JPS5838235A/ja active Pending
- 1982-07-26 IE IE1784/82A patent/IE54596B1/en unknown
- 1982-07-26 DE DE19823227846 patent/DE3227846A1/de not_active Withdrawn
- 1982-07-26 PT PT75324A patent/PT75324B/pt unknown
- 1982-07-26 CH CH4540/82A patent/CH652710A5/fr not_active IP Right Cessation
- 1982-07-26 BE BE0/208678A patent/BE893942A/fr not_active IP Right Cessation
- 1982-07-26 NL NL8202995A patent/NL8202995A/nl not_active Application Discontinuation
- 1982-07-27 RO RO108285A patent/RO85386B/ro unknown
- 1982-07-27 KR KR8203347A patent/KR890001806B1/ko active
- 1982-07-27 DD DD82241978A patent/DD202423A5/de unknown
-
1983
- 1983-06-16 ES ES523320A patent/ES8500210A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE821784L (en) | 1983-01-27 |
| FR2510102A1 (fr) | 1983-01-28 |
| ES523320A0 (es) | 1984-10-01 |
| US4405805A (en) | 1983-09-20 |
| BR8204352A (pt) | 1983-07-19 |
| CA1203811A (en) | 1986-04-29 |
| PL144334B1 (en) | 1988-05-31 |
| GB2103214B (en) | 1986-07-02 |
| ES8500210A1 (es) | 1984-10-01 |
| NL8202995A (nl) | 1983-02-16 |
| DK333582A (da) | 1983-01-28 |
| PL237635A1 (en) | 1984-08-13 |
| DD202423A5 (de) | 1983-09-14 |
| DE3227846A1 (de) | 1983-02-10 |
| JPS5838235A (ja) | 1983-03-05 |
| ES514354A0 (es) | 1983-10-16 |
| GB2103214A (en) | 1983-02-16 |
| HU190694B (en) | 1986-10-28 |
| IL66357A (en) | 1986-04-29 |
| RO85386A (ro) | 1984-11-25 |
| PT75324A (fr) | 1982-08-01 |
| IT1156314B (it) | 1987-02-04 |
| ES8400386A1 (es) | 1983-10-16 |
| IT8222547A1 (it) | 1984-01-23 |
| RO85386B (ro) | 1984-11-30 |
| IE54596B1 (en) | 1989-12-06 |
| IL66357A0 (en) | 1982-11-30 |
| BE893942A (fr) | 1983-01-26 |
| KR890001806B1 (ko) | 1989-05-23 |
| PT75324B (fr) | 1985-11-29 |
| LU84297A1 (fr) | 1984-03-22 |
| CH652710A5 (fr) | 1985-11-29 |
| FR2510102B1 (fr) | 1985-10-11 |
| IT8222547A0 (it) | 1982-07-23 |
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