FR2529197A1 - Procede de preparation de phenates substitues par des groupes halogenes ou des phenols correspondants - Google Patents
Procede de preparation de phenates substitues par des groupes halogenes ou des phenols correspondants Download PDFInfo
- Publication number
- FR2529197A1 FR2529197A1 FR8211616A FR8211616A FR2529197A1 FR 2529197 A1 FR2529197 A1 FR 2529197A1 FR 8211616 A FR8211616 A FR 8211616A FR 8211616 A FR8211616 A FR 8211616A FR 2529197 A1 FR2529197 A1 FR 2529197A1
- Authority
- FR
- France
- Prior art keywords
- halogen atom
- formula
- hydroxide
- compound
- atom
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000002367 halogens Chemical group 0.000 title abstract description 8
- 150000002989 phenols Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 150000004679 hydroxides Chemical class 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 2
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical group 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 238000001033 granulometry Methods 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- WIMFOMTYQPDJBK-UHFFFAOYSA-N 3-chloro-2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(Cl)=C1C(F)(F)F WIMFOMTYQPDJBK-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 235000011118 potassium hydroxide Nutrition 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XILPLWOGHPSJBK-UHFFFAOYSA-N 1,2-dichloro-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C(Cl)=C1 XILPLWOGHPSJBK-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- XZGIHWAIIZHXKX-UHFFFAOYSA-N 2-(2-ethoxyethoxy)-n,n-bis[2-(2-ethoxyethoxy)ethyl]ethanamine Chemical compound CCOCCOCCN(CCOCCOCC)CCOCCOCC XZGIHWAIIZHXKX-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- YNWKEXMSQQUMEL-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1Cl YNWKEXMSQQUMEL-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical class [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 229910052751 metal Chemical group 0.000 description 1
- 239000002184 metal Chemical group 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8211616A FR2529197A1 (fr) | 1982-06-29 | 1982-06-29 | Procede de preparation de phenates substitues par des groupes halogenes ou des phenols correspondants |
| US06/509,062 US4504689A (en) | 1982-06-29 | 1983-06-29 | Process for the preparation of phenates substituted by halogen groups or of the corresponding phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8211616A FR2529197A1 (fr) | 1982-06-29 | 1982-06-29 | Procede de preparation de phenates substitues par des groupes halogenes ou des phenols correspondants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2529197A1 true FR2529197A1 (fr) | 1983-12-30 |
| FR2529197B1 FR2529197B1 (OSRAM) | 1984-12-07 |
Family
ID=9275616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8211616A Granted FR2529197A1 (fr) | 1982-06-29 | 1982-06-29 | Procede de preparation de phenates substitues par des groupes halogenes ou des phenols correspondants |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4504689A (OSRAM) |
| FR (1) | FR2529197A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0173993A1 (en) * | 1984-09-03 | 1986-03-12 | Toyo Soda Manufacturing Co., Ltd. | Tert-butyl-halophenol |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3921449A1 (de) * | 1989-06-30 | 1991-01-03 | Hoechst Ag | Verfahren zur herstellung von 1,4-bis-(4-hydroxybenzolyl)-benzol |
| BR112019017945A2 (pt) | 2017-04-04 | 2020-05-19 | Adama Agan Ltd | processo para separar o composto (i), ou um sal do mesmo, de uma mistura, método para obter o composto (i), composto (i) e composição |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1408502A (fr) * | 1963-09-19 | 1965-08-13 | Ici Ltd | Procédé de fabrication de nouveaux dérivés de fluorochlorobenzènes |
| GB1110232A (en) * | 1964-02-21 | 1968-04-18 | Mini Of Technology | Fluoro-organic compounds |
| US3481991A (en) * | 1963-06-03 | 1969-12-02 | Dover Chem Corp | Preparation of chlorinated hydroxy compounds |
| DE2042569A1 (en) * | 1970-08-27 | 1972-03-02 | Biller, Efim, Freiburg (Schweiz) | Phenol mixtures contg m-dioxybenzene prepn - by reacting o-or p-chlorophenol with alkali hydroxide under an hydrous conditions |
| US3651154A (en) * | 1968-01-29 | 1972-03-21 | American Cyanamid Co | Process for preparing polyhalonaphthols |
| EP0019388A1 (en) * | 1979-05-02 | 1980-11-26 | Rohm And Haas Company | Preparation of trifluoromethyl-substituted phenols and phenates and the preparation, from these phenols and phenates, of nitro- and trifluoromethyl-substituted diphenyl ethers |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2733682A1 (de) * | 1977-07-26 | 1979-02-08 | Bayer Ag | Verfahren zur herstellung von trifluormethylphenolen |
| US4122288A (en) * | 1977-11-16 | 1978-10-24 | Uop Inc. | Hydrolysis of alkyl substituted dihalobenzene compounds |
| US4259510A (en) * | 1979-05-02 | 1981-03-31 | Rohm And Haas Company | Preparation of trifluoromethylphenyl nitrophenylethers |
-
1982
- 1982-06-29 FR FR8211616A patent/FR2529197A1/fr active Granted
-
1983
- 1983-06-29 US US06/509,062 patent/US4504689A/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3481991A (en) * | 1963-06-03 | 1969-12-02 | Dover Chem Corp | Preparation of chlorinated hydroxy compounds |
| FR1408502A (fr) * | 1963-09-19 | 1965-08-13 | Ici Ltd | Procédé de fabrication de nouveaux dérivés de fluorochlorobenzènes |
| GB1110232A (en) * | 1964-02-21 | 1968-04-18 | Mini Of Technology | Fluoro-organic compounds |
| US3651154A (en) * | 1968-01-29 | 1972-03-21 | American Cyanamid Co | Process for preparing polyhalonaphthols |
| DE2042569A1 (en) * | 1970-08-27 | 1972-03-02 | Biller, Efim, Freiburg (Schweiz) | Phenol mixtures contg m-dioxybenzene prepn - by reacting o-or p-chlorophenol with alkali hydroxide under an hydrous conditions |
| EP0019388A1 (en) * | 1979-05-02 | 1980-11-26 | Rohm And Haas Company | Preparation of trifluoromethyl-substituted phenols and phenates and the preparation, from these phenols and phenates, of nitro- and trifluoromethyl-substituted diphenyl ethers |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0173993A1 (en) * | 1984-09-03 | 1986-03-12 | Toyo Soda Manufacturing Co., Ltd. | Tert-butyl-halophenol |
Also Published As
| Publication number | Publication date |
|---|---|
| US4504689A (en) | 1985-03-12 |
| FR2529197B1 (OSRAM) | 1984-12-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |