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US5227540A
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Process for the preparation of primary and secondary fluorine-containing alcohols
Assignee: Clariant Produkte Deutschland GmbH
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Filing: 1992-07-24
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Granted: 1993-07-13
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Expires: 2012-07-24
Abstract
Abstract A process is described for the preparation of fluoroalcohols of the formula below ##STR1## in which R f is a perfluoroalkyl radical having 1 to 20 carbon atoms and R is hydrogen or an alkyl radical having 1 to 5 carbon atoms, by reaction of a perfluoroalkylethylene, R f --CH═CH 2 , and an n-C 1 to C 6 -alkanol in the presence of a free radical initiator, the perfluoroalkylethylene, the alkanol and the free radical initiator being used in the molar ratio of 1 to 20-50 to 0.002-0.2. In the novel process, in addition, the reaction is carried out in a specific manner and under specific reaction conditions. The fluoroalcohols given are obtained in high yield.
Inventors
- 👤 Wolfgang Knaup
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 16:01
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/44
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
200 words
A process for the preparation of a primary or secondary fluorine-containing alcohol of the formula 1 below ##STR5## in which R f is perfluoroalkyl radical having 1 to 20 carbon atoms and R is hydrogen or an alkyl radical having 1 to 5 carbon atoms, by reaction of a perfluoroalkylethylene of the formula 2 below R.sub.f --CH═CH.sub.2 in which R f has the meaning given, with an n-C 6 -alkanol in the presence of a free radical initiator, which comprises using the perfluoroalkylethylene compound, the alkanol compound and the free radical initiator in a molar ratio of 1 to 20-50 to 0.002-0.2, wherein said free radical initiator is selected from the group consisting of dialkyl peroxides, diacyl peroxides and peroxycarboxylic esters and carrying out the reaction in such a manner that the alkanol compound is taken first and heated to a temperature which is in the range from 50° C. below to 10° C. above the one-minute halflife temperature of the free radical initiator and is 50° to 230° C. and then at this temperature the perfluoroalkylethylene and the free radical initiator are simultaneously and essentially continuously added to the alkanol in a time period of 1 to 10 hours.
Claim 2
Dependent Claim
200 words
A process for the preparation of a primary or secondary fluorine-containing alcohol of the formula 1 below ##STR5## in which R f is perfluoroalkyl radical having 1 to 20 carbon atoms and R is hydrogen or an alkyl radical having 1 to 5 carbon atoms, by reaction of a perfluoroalkylethylene of the formula 2 below R.sub.f --CH═CH.sub.2 in which R f has the meaning given, with an n-C 6 -alkanol in the presence of a free radical initiator, which comprises using the perfluoroalkylethylene compound, the alkanol compound and the free radical initiator in a molar ratio of 1 to 20-50 to 0.002-0.2, wherein said free radical initiator is selected from the group consisting of dialkyl peroxides, diacyl peroxides and peroxycarboxylic esters and carrying out the reaction in such a manner that the alkanol compound is taken first and heated to a temperature which is in the range from 50° C. below to 10° C. above the one-minute halflife temperature of the free radical initiator and is 50° to 230° C. and then at this temperature the perfluoroalkylethylene and the free radical initiator are simultaneously and essentially continuously added to the alkanol in a time period of 1 to 10 hours.
Claim 3
Dependent Claim
31 words
The process as claimed in claim 1, wherein the perfluoroalkylethylene compound, the alkanol compound and the free radical initiator are used in a molar ratio of 1 to 25-40 to 0.005-0.1.
Claim 4
Dependent Claim
44 words
The process as claimed in claim 1, wherein the alkanol compound is heated to a temperature which is in the range from 50° C. below to 10° C. above the one-minute halflife temperature of the free radical initiator and is 80° to 200° C.
Claim 5
Dependent Claim
29 words
The process as claimed in claim 1, wherein the perfluoroalkylethylene and the free radical initiator are added to the alkanol in a time period of 2 to 8 hours.
Claim 6
Dependent Claim
111 words
The process as claimed in claim 1, wherein the perfluoroalkylethylene compound, the alkanol compound and the free radical initiator are used in a molar ratio of 1 to 25-40 to 0.005-0.1 and the reaction is carried out in such a manner that the alkanol compound is taken first and heated to a temperature which is in the range from 50° C. below to 10° C. above the one-minute halflife temperature of the free radical initiator and is 80° to 200° C. and then at this temperature the perfluoroalkylethylene and the free radical initiator are simultaneously and essentially continuously added to the alkanol in a time period of 2 to 8 hours.
Claim 7
Dependent Claim
28 words
The process as claimed in claim 1, wherein R f is a perfluoroalkyl radical having 6 to 16 carbons atoms and R is hydrogen or CH 3 .
Claim 8
Dependent Claim
24 words
The process of claim 1, wherein the free radical initiator tert-butyl hydroperoxide, di-tert-butyl peroxide, diacetyl peroxide, dilauroyl peroxide, dibenzoyl peroxide, tert-butyl perpivalate tert-butyl perbenzoate.
Claim 9
Dependent Claim
24 words
The process as claimed in claim 1, wherein the free radical initiator is a di-tert-butyl peroxide or a tert-butyl perpivalate or a benzoyl peroxide.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-07-12 | 1997-01-11 | 1997-07-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-07-12 | 2001-01-11 | 2001-07-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-07-12 | 2005-01-11 | 2005-07-13 | $7700.00 | Window Closed / Lapsed |