GB904263A - Perfluoroalkyl alkanols - Google Patents
Perfluoroalkyl alkanolsInfo
- Publication number
- GB904263A GB904263A GB1628462A GB1628462A GB904263A GB 904263 A GB904263 A GB 904263A GB 1628462 A GB1628462 A GB 1628462A GB 1628462 A GB1628462 A GB 1628462A GB 904263 A GB904263 A GB 904263A
- Authority
- GB
- United Kingdom
- Prior art keywords
- perfluorooctyl
- reduced
- give
- acid
- alcohol
- 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
- 125000005010 perfluoroalkyl group Chemical group 0.000 title 1
- 230000002829 reductive effect Effects 0.000 abstract 5
- -1 sulphonyl halide Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- FQTWAKFTSLUFFS-UHFFFAOYSA-N 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecan-1-ol Chemical compound OCCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FQTWAKFTSLUFFS-UHFFFAOYSA-N 0.000 abstract 1
- HCZYZQOSKMVJNT-UHFFFAOYSA-N 4-chloro-6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-heptadecafluorotridecanoic acid Chemical compound ClC(CCC(=O)O)CC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F HCZYZQOSKMVJNT-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 abstract 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 abstract 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005233 alkylalcohol group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 238000005695 dehalogenation reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- JVHJRIQPDBCRRE-UHFFFAOYSA-N ethyl 2,2,3,3,4,4,4-heptafluorobutanoate Chemical compound CCOC(=O)C(F)(F)C(F)(F)C(F)(F)F JVHJRIQPDBCRRE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 abstract 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 abstract 1
- 229940090181 propyl acetate Drugs 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
- C08F20/24—Esters containing halogen containing perhaloalkyl radicals
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 the compounds Rf(CH2)mOH, where Rf is a perfluoroalkyl radical having 3-12 carbon atoms and m is 3-12. These compounds may be prepared by the desulphonylative addition of a perfluoroalkane sulphonyl halide to a terminally unsaturated alcohol, esterified alcohol, or carboxylic acid, followed by reductive dehalogenation to replace halogen by chlorine, and hydrolysis if an esterified alcohol was used or reduction if an acid was used. In Examples, (1) C8F17SO2Cl is reacted with 4-pentenoic acid to give 4-chloro-5-(perfluorooctyl)-pentanoic acid, which is hydrogenated to 5-perfluorooctyl pentanoic acid, and this is reduced to 5-perfluorooctyl-pentanol; (2) C8F17SO2Cl is reacted with alkyl acetate to give 2-chloro-3-(perfluorooctyl) propyl acetate, which is dehydrohalogenated to 3-(perfluorooctyl) alkyl alcohol, and this is reduced to 3-(perfluorooctyl) propanol; (3) ethyl perfluorobutyrate is condensed with methyl acetate to give C3F7COCH2COOCH3, this is reduced to C3F7CHOHCH2COOCH3, which is dehydrated to C3F7CH:CHCOOCH3; this is hydrogenated to the saturated ester, which is reduced to C3F7(CH2)3OH.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1628462A GB904263A (en) | 1958-08-11 | 1958-08-11 | Perfluoroalkyl alkanols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1628462A GB904263A (en) | 1958-08-11 | 1958-08-11 | Perfluoroalkyl alkanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB904263A true GB904263A (en) | 1962-08-29 |
Family
ID=10074548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1628462A Expired GB904263A (en) | 1958-08-11 | 1958-08-11 | Perfluoroalkyl alkanols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB904263A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1214660B (en) * | 1963-10-09 | 1966-04-21 | Du Pont | Process for the preparation of fluoroalkanols |
| US4098806A (en) * | 1976-03-05 | 1978-07-04 | Produits Chimiques Ugine Kuhlmann | Process for functionalizing perfluorohalogenoalkanes |
| US5852148A (en) * | 1991-07-10 | 1998-12-22 | Minnesota Mining & Manufacturing Company | Perfluoroalkyl halides and derivatives |
| US6048952A (en) * | 1991-07-10 | 2000-04-11 | 3M Innovative Properties Company | Perfluoroalkyl halides and derivatives |
| WO2001058833A1 (en) * | 2000-02-11 | 2001-08-16 | Rhodia Chimie | Method for functionalising a double bond |
-
1958
- 1958-08-11 GB GB1628462A patent/GB904263A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1214660B (en) * | 1963-10-09 | 1966-04-21 | Du Pont | Process for the preparation of fluoroalkanols |
| US4098806A (en) * | 1976-03-05 | 1978-07-04 | Produits Chimiques Ugine Kuhlmann | Process for functionalizing perfluorohalogenoalkanes |
| US5852148A (en) * | 1991-07-10 | 1998-12-22 | Minnesota Mining & Manufacturing Company | Perfluoroalkyl halides and derivatives |
| US6048952A (en) * | 1991-07-10 | 2000-04-11 | 3M Innovative Properties Company | Perfluoroalkyl halides and derivatives |
| US6365769B1 (en) | 1991-07-10 | 2002-04-02 | 3M Innovative Properties Company | Perfluoroalkyl halides and derivatives |
| WO2001058833A1 (en) * | 2000-02-11 | 2001-08-16 | Rhodia Chimie | Method for functionalising a double bond |
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