GB1442908A - - Google Patents
Info
- Publication number
- GB1442908A GB1442908A GB2350274A GB2350274A GB1442908A GB 1442908 A GB1442908 A GB 1442908A GB 2350274 A GB2350274 A GB 2350274A GB 2350274 A GB2350274 A GB 2350274A GB 1442908 A GB1442908 A GB 1442908A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trifluorostyrene
- reaction
- koh
- chloro
- chlorine
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052731 fluorine Chemical group 0.000 abstract 2
- 239000011737 fluorine Chemical group 0.000 abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- YHAGRAVHTLEVRV-UHFFFAOYSA-N 1,3-dichloro-1,2,3,3-tetrafluoro-2-phenylpropan-1-ol Chemical compound ClC(C(C(Cl)(F)F)(C1=CC=CC=C1)F)(O)F YHAGRAVHTLEVRV-UHFFFAOYSA-N 0.000 abstract 1
- BHZQQRBHYIYZMY-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-phenylpropanoic acid Chemical compound OC(=O)C(F)(C(F)(F)F)C1=CC=CC=C1 BHZQQRBHYIYZMY-UHFFFAOYSA-N 0.000 abstract 1
- JQSYIUBMLRKZNR-UHFFFAOYSA-N 2-[chloro(difluoro)methyl]-3,3-difluoro-2-phenyloxirane Chemical compound C=1C=CC=CC=1C1(C(F)(Cl)F)OC1(F)F JQSYIUBMLRKZNR-UHFFFAOYSA-N 0.000 abstract 1
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical class CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal salt Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
- C07C17/363—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/295—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with inorganic bases, e.g. by alkali fusion
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1442908 Production of α,#,#-trifluorostyrene INST ELEMETOORGANICH SOEDIN AKAD NAUK SSSR 28 May 1974 23502/74 Heading C2C A method of preparing α,#,#-trifluorostyrene comprises the following steps: (a) reacting with an alkali at least one chlorine and fluorine substituted 2-phenylpropanol-2 having the general formula where n = 1, 2 or 3, in a solvent medium selected from water and branched aliphatic alcohol in which the branching occurs at the carbinol and/or at the carbon atoms immediately adjacent thereto said reaction being carried out at a temperature of from 40 C. to the boiling point of the solvent medium; (b) isolating from the reaction mixture a solid residue, containing an alkali metal salt of chlorine and fluorine substituted α-phenylpropionic acid; and, (c) dry distilling said solid residue to obtain α,#,#-trifluorostyrene as distillate. Preparations of the following intermediates are given: (a) α-phenyl-tetrafluoropropionic acid by the reaction of 1-chloro-2-phenylpentafluoropropanol-2, KOH and t-butanol (see Example 3); (b) 3 - chloro - 2 - phenyl - 1,2 - epoxytetrafluoropropane by reacting 1,3-dichloro-2-phenyltetrafluoropropanol with KOH at 80-90 C., and dehydrating the resulting compound with MgSO 4 (see Example 5).
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE144398A BE815129A (en) | 1974-05-16 | 1974-05-16 | Alpha, beta, beta-trifluorostyrene prepn - from chlorinated and fluorinated 2-phenylpropan-2-ol(s) and alkali |
| NL7407032A NL7407032A (en) | 1974-05-16 | 1974-05-24 | Alpha, beta, beta-trifluorostyrene prepn - from chlorinated and fluorinated 2-phenylpropan-2-ol(s) and alkali |
| DE19742425550 DE2425550A1 (en) | 1974-05-16 | 1974-05-27 | Alpha, beta, beta-trifluorostyrene prepn - from chlorinated and fluorinated 2-phenylpropan-2-ol(s) and alkali |
| GB2350274A GB1442908A (en) | 1974-05-16 | 1974-05-28 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE144398A BE815129A (en) | 1974-05-16 | 1974-05-16 | Alpha, beta, beta-trifluorostyrene prepn - from chlorinated and fluorinated 2-phenylpropan-2-ol(s) and alkali |
| NL7407032A NL7407032A (en) | 1974-05-16 | 1974-05-24 | Alpha, beta, beta-trifluorostyrene prepn - from chlorinated and fluorinated 2-phenylpropan-2-ol(s) and alkali |
| DE19742425550 DE2425550A1 (en) | 1974-05-16 | 1974-05-27 | Alpha, beta, beta-trifluorostyrene prepn - from chlorinated and fluorinated 2-phenylpropan-2-ol(s) and alkali |
| GB2350274A GB1442908A (en) | 1974-05-16 | 1974-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1442908A true GB1442908A (en) | 1976-07-14 |
Family
ID=89847655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2350274A Expired GB1442908A (en) | 1974-05-16 | 1974-05-28 |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE815129A (en) |
| DE (1) | DE2425550A1 (en) |
| GB (1) | GB1442908A (en) |
| NL (1) | NL7407032A (en) |
-
1974
- 1974-05-16 BE BE144398A patent/BE815129A/en unknown
- 1974-05-24 NL NL7407032A patent/NL7407032A/en unknown
- 1974-05-27 DE DE19742425550 patent/DE2425550A1/en active Pending
- 1974-05-28 GB GB2350274A patent/GB1442908A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2425550A1 (en) | 1975-12-11 |
| NL7407032A (en) | 1975-11-26 |
| BE815129A (en) | 1974-11-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |