GB1110232A - Fluoro-organic compounds - Google Patents
Fluoro-organic compoundsInfo
- Publication number
- GB1110232A GB1110232A GB736064A GB736064A GB1110232A GB 1110232 A GB1110232 A GB 1110232A GB 736064 A GB736064 A GB 736064A GB 736064 A GB736064 A GB 736064A GB 1110232 A GB1110232 A GB 1110232A
- Authority
- GB
- United Kingdom
- Prior art keywords
- salts
- nonafluoro
- carbon atoms
- substituted
- alkaline
- 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
Links
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000001153 fluoro group Chemical group F* 0.000 abstract 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 5
- 239000003513 alkali Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- -1 alkaline-earth metal salts Chemical class 0.000 abstract 3
- 150000002989 phenols Chemical group 0.000 abstract 3
- HZQGKHUTYHEFBT-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenol Chemical class OC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F HZQGKHUTYHEFBT-UHFFFAOYSA-N 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 159000000001 potassium salts Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- USPWUOFNOTUBAD-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F USPWUOFNOTUBAD-UHFFFAOYSA-N 0.000 abstract 1
- LALVQFXNRXDTGV-UHFFFAOYSA-N 1,2,3,5-tetrafluoro-4,6-bis(trifluoromethyl)benzene Chemical group FC1=C(F)C(C(F)(F)F)=C(F)C(C(F)(F)F)=C1F LALVQFXNRXDTGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/44—Metal derivatives of an hydroxy group bound to a carbon atom of 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
- C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
- C07C37/66—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring by conversion of hydroxy groups to O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises p-linked polymers containing repeating units of the formula -Ar-C(F)(R)-O-, in which Ar is a p-phenylene group, which may be substituted by one or more perfluoroalkyl groups of 1-3 carbon atoms and/or by one or more nuclear fluorine atoms, and R is fluorine or a perfluoroalkyl group of 1-3 carbon atoms. The polymers are prepared by polymerizing alkali or alkaline-earth metal salts of phenols substituted in the nucleus with one or more perfluoroalkyl groups of 1-3 carbon atoms and optionally substituted in addition by one or more nuclear fluorine atoms (see Division C2), polymerization being effected by heating the salts with water. Examples are given in which the potassium salts of heptafluoro-p-cresol, nonafluoro-p-ethyl-phenol, nonafluoro - 2,4 - dimethylphenol are polymerized by heating in water to 70-100 DEG C. Some of the products yield elastomers when heated in vacuo to 180-250 DEG C. with an alkali or alkaline-earth metal salt.ALSO:The invention comprises alkali and alkaline-earth metal salts of phenols substituted in the nucleus with one or more perfluoroalkyl groups of 1-3 carbon atoms and optionally substituted in addition by one or more nuclear fluorine atoms. The salts may be prepared by the action of an alkali or alkaline-earth metal hydroxide, in the presence of a solvent, on a benzene hydrocarbon substituted with at least one nuclear fluorine atom and at least one perfluoroalkyl group of 1-3 carbon atoms. Examples are given of the manufacture of the potassium salts of heptafluoro-p-cresol, nonafluoro-p-ethyl-phenol nonafluoro - 3,4 - (or 2,5) - dimethylphenol and nonafluoro-2,4-dimethylphenol by the action of potassium hydroxide on octafluorotoluene, decafluoro-p-ethylbenzene, decafluoro-o-(or p-)xylene and decafluoro-m-xylene, respectively. The free phenols can be recovered by acidifying the salts. The salts are polymerizable (see Division C3).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB736064A GB1110232A (en) | 1964-02-21 | 1964-02-21 | Fluoro-organic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB736064A GB1110232A (en) | 1964-02-21 | 1964-02-21 | Fluoro-organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1110232A true GB1110232A (en) | 1968-04-18 |
Family
ID=9831622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB736064A Expired GB1110232A (en) | 1964-02-21 | 1964-02-21 | Fluoro-organic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1110232A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2529197A1 (en) * | 1982-06-29 | 1983-12-30 | Rhone Poulenc Agrochimie | PROCESS FOR THE PREPARATION OF PHENATES SUBSTITUTED BY HALOGEN GROUPS OR CORRESPONDING PHENOLS |
-
1964
- 1964-02-21 GB GB736064A patent/GB1110232A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2529197A1 (en) * | 1982-06-29 | 1983-12-30 | Rhone Poulenc Agrochimie | PROCESS FOR THE PREPARATION OF PHENATES SUBSTITUTED BY HALOGEN GROUPS OR CORRESPONDING PHENOLS |
| US4504689A (en) * | 1982-06-29 | 1985-03-12 | Serge Veracini | Process for the preparation of phenates substituted by halogen groups or of the corresponding phenols |
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