US4968848A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process of the prparation of perfluoroalkyl compounds, and pentafluoroethyltrimethylsilane
Assignee: Hoechst AG
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Filing: 1989-02-21
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Granted: 1990-11-06
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Expires: 2009-02-21
Abstract
Abstract A process for the preparation of perfluoroalkyl compounds which comprises reacting a perfluoroalkyl-trimethylsilane of the general formula (CH 3 ) 3 Si-C n F 2n+1 (I), wherein the group C n F 2n+1 represents a perfluoroalkyl group having from 1 to 6 carbon atoms, with a carbonyl compound of the general formula F 1 --CO--R 2 (II), wherein R 1 represents a hydrocarbon group or hydrogen and R 2 represents a hydrocarbon group, a perfluoroalkyl group or a perfluoroaryl group, but wherein R 1 and R 2 together may also be part of an alicyclic ring system, in the presence of a salt-like fluoride--which is at least partially soluble in the reaction medium--as a catalyst to yield a silylether of the formula ##STR1## and isolating this compound or hydrolyzing it to yield an alcohol of the formula IV ##STR2## The invention also relates to pentafluoroethyl trimethylsilane (CH 3 ) 3 Si--CF 2 CF 3 and a process for the preparation of this compound.
Inventors
- 👤 Alfred Kruse
- 👤 Gunter Siegemund
- 👤 Axel Schumann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 21:33
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/132; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/188; C07F7/0803; C07F7/081; C07F7/0825; C07F7/0827
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
139 words
A process for the preparation of perfluoroalkyl compounds which comprises reacting a perfluoroalkyltrimethylsilane of the general formula (CH 3 ) 3 Si--C n F 2n+1 (I), wherein the group C n F 2n+a represents a perfluoroalkyl group having from 1 to 6 carbon atoms, with a carbonyl compound of the general formula R 1 --CO--R 2 (II), wherein R 1 represents a hydrocarbon group or hydrogen and R 2 represents a hydrocarbon group, a perfluoroalkyl group or a perfluoroaryl group, but wherein R 1 and R 2 together may also be part of an alicyclic ring system, in the presence of a fluoride salt--which is at least partially soluble in the reaction medium--as a catalyst to yield a silylether of the formula ##STR12## and isolating this compound of hydrolyzing it to yield an alcohol of the formula IV ##STR13##
Claim 2
Dependent Claim
139 words
A process for the preparation of perfluoroalkyl compounds which comprises reacting a perfluoroalkyltrimethylsilane of the general formula (CH 3 ) 3 Si--C n F 2n+1 (I), wherein the group C n F 2n+a represents a perfluoroalkyl group having from 1 to 6 carbon atoms, with a carbonyl compound of the general formula R 1 --CO--R 2 (II), wherein R 1 represents a hydrocarbon group or hydrogen and R 2 represents a hydrocarbon group, a perfluoroalkyl group or a perfluoroaryl group, but wherein R 1 and R 2 together may also be part of an alicyclic ring system, in the presence of a fluoride salt--which is at least partially soluble in the reaction medium--as a catalyst to yield a silylether of the formula ##STR12## and isolating this compound of hydrolyzing it to yield an alcohol of the formula IV ##STR13##
Claim 3
Dependent Claim
17 words
A process as claimed in claim 1, wherein the fluoride is an alkali fluoride or alkali bifluoride.
Claim 4
Dependent Claim
16 words
A process as claimed in claim 2, wherein the fluoride is potassium fluoride or cesium fluoride.
Claim 5
Dependent Claim
27 words
A process as claimed in claim 1, wherein the catalyst is applied in an amount of from 2 to 30 mol-%, referred to the carbonyl compound II.
Claim 6
Dependent Claim
27 words
A process as claimed in claim 4, wherein the catalyst is applied in an amount of from 10 to 25 mol-%, referred to the carbonyl compound II.
Claim 7
Dependent Claim
40 words
A process as claimed in claim 1, which is carried out under anyhydrous conditions in the presence of a solvent or diluent which under the reaction conditions is inert towards the reactants and has a solvent capacity for the catalyst.
Claim 8
Dependent Claim
23 words
A process as claimed in claim 1, which is carried out at a temperature in the range of from 0° to 100° C.
Claim 9
Dependent Claim
23 words
A process as claimed in claim 7, which is carried out at a temperature in the range of from 20° to 60° C.
Claim 10
Dependent Claim
37 words
A process as claimed in claim 1, wherein the silane I is applied in an amount at least equivalent to the carbonyl compound and at most in an amount up to 25 mol-% above the equivalent amount.
Claim 11
Dependent Claim
26 words
A process as claimed in claim 1, wherein R 1 and R 2 in the carbonyl compound II each have from 1 to 10 carbon atoms.
Claim 12
Dependent Claim
26 words
A process as claimed in claim 1, wherein R 1 and R 2 in the carbonyl compound II each have from 1 to 6 carbon atoms.
Claim 13
Dependent Claim
52 words
A process as claimed in claim 6, wherein the solvent is an ether selected from the group consisting of tetrahydrofuran and a polyester of the formula CH 3 --O--[CH 2 --alk--O] n --CH 3 wherein n is an integer from 1 to 4 and alk represents CH--CH 3 or CH 2 .
Claim 14
Dependent Claim
12 words
A process as claimed in claim 6, wherein the solvent is dimethylflormamide.
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-11-05 | 1994-05-07 | 1994-11-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-11-05 | 1998-05-07 | 1998-11-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-11-05 | 2002-05-07 | 2002-11-06 | $7700.00 | Window Closed / Lapsed |