US4804773A
Expired / Lapsed
US
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Production of gem-disubstituted cyclohexadienones
Assignee: Albemarle Corp
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Filing: 1988-04-04
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Granted: 1989-02-14
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Expires: 2008-04-04
Abstract
Abstract Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using an aminopyridine as catalyst. The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsilyloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.
Inventors
- 👤 G. Patrick Stahly
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 12:24
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/188
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
29 words
A process which comprises reacting under essentially anhydrous conditions a quinone with a perfluoroalkyltrihydrocarbylsilane in the presence of an active aminopyridine catalyst so that a gem-disubstituted cyclohexadienone is produced.
Claim 2
Dependent Claim
29 words
A process which comprises reacting under essentially anhydrous conditions a quinone with a perfluoroalkyltrihydrocarbylsilane in the presence of an active aminopyridine catalyst so that a gem-disubstituted cyclohexadienone is produced.
Claim 3
Dependent Claim
12 words
A process of claim 1 conducted in a liquid phase reaction medium.
Claim 4
Dependent Claim
11 words
A process of claim 1 wherein the quinone is a 1,4-quinone.
Claim 5
Dependent Claim
12 words
A process of claim 3 wherein the 1,4-quinone is a mononuclear 1,4-quinone.
Claim 6
Dependent Claim
12 words
A process of claim 3 wherein the 1,4-quinone is a polynuclear 1,4-quinone.
Claim 7
Dependent Claim
14 words
A process of claim 3 wherein the 1,4-quinone is a polynuclear fused ring 1,4-quinone.
Claim 8
Dependent Claim
11 words
A process of claim 1 wherein the quinone is a 1,2-quinone.
Claim 9
Dependent Claim
12 words
A process of claim 7 wherein the 1,2-quinone is a mononuclear 1,2-quinone.
Claim 10
Dependent Claim
14 words
A process of claim 7 wherein the 1,2-quinone is a polynuclear fused ring 1,2-quinone.
Claim 11
Dependent Claim
11 words
A process of claim 1 wherein the perfluoroalkyltrihydrocarbylsilane is a perfluoroalkyltrialkylsilane.
Claim 12
Dependent Claim
11 words
A process of claim 1 wherein the perfluoroalkyltrihydrocarbylsilane is a trifluoromethyltrihydrocarbylsilane.
Claim 13
Dependent Claim
11 words
A process of claim 1 wherein the perfluoroalkyltrihydrocarbysilane is a trifluoromethyltrialkylsilane.
Claim 14
Dependent Claim
14 words
A process of claim 1 wherein the catalyst is an alkylamino- or dialkylaminopyridine .
Claim 15
Dependent Claim
11 words
A process of claim 1 wherein the catalyst is a dimethylaminopyridine.
Claim 16
Dependent Claim
10 words
A process of claim 1 wherein the catalyst is 4-dimethylaminopyridine.
Claim 17
Dependent Claim
17 words
A process of claim 1 wherein the reaction is performed in a liquid dipolar aprotic reaction medium.
Claim 18
Dependent Claim
21 words
A process of claim 1 wherein the reaction is performed in a liquid reaction medium comprising N,N-dimethylformamide, N,N-dimethylacetamide, sulfolane or acetonitrile.
Claim 19
Dependent Claim
26 words
A process of claim 1 wherein the reaction is performed in a liquid reaction medium consisting essentially of acetonitrile and wherein the catalyst is a dialkylaminopyridine.
Claim 20
Dependent Claim
25 words
A process of claim 1 wherein the reaction is performed in a liquid reaction medium consisting essentially of acetonitrile and wherein the catalyst is 4-dimethylaminopyridine.
Claim 21
Dependent Claim
25 words
A process of claim 1 wherein the temperature is maintained in the range of about 0° to about 25° C. throughout substantially the entire reaction.
Claim 22
Dependent Claim
37 words
A process which comprises reacting under essentially anhydrous conditions in a liquid phase reaction medium a 1,2- or 4-quinone with a trifluoromethyltrihydrocarbylsilane in the presence of an active aminopyridine catalyst so that a gem-disubstituted cyclohexadienone is produced.
Claim 23
Dependent Claim
37 words
A process which comprises reacting under essentially anhydrous conditions in a liquid phase reaction medium a 1,2- or 4-quinone with a trifluoromethyltrihydrocarbylsilane in the presence of an active aminopyridine catalyst so that a gem-disubstituted cyclohexadienone is produced.
Claim 24
Dependent Claim
16 words
A process of claim 21 wherein said catalyst is an alkylamino- or a dialkylaminopyridine, or both.
Claim 25
Dependent Claim
16 words
A process of claim 21 wherein the reaction medium consist essentially of a dipolar aprotic solvent.
Claim 26
Dependent Claim
15 words
A process of claim 21 wherein the reaction medium comprises N,N-dimethylformamide, N,N-dimethylacetamide, sulfolane or acetonitrile.
Claim 27
Dependent Claim
25 words
A process of claim 21 wherein the temperature is maintained in the range of about 0° to about 25° C. throughout substantially the entire reaction.
Claim 28
Dependent Claim
50 words
A process of claim 21 wherein the trifluoromethyltrihydrocarbylsilane is a trifluoromethyltrialkylsilane; wherein said catalyst is a dimethylaminopyridine; wherein the reaction medium consist essentially of N,N-dimethylformamide, N,N-dimethylacetamide, sulfolane or acetonitrile; and wherein the temperature is maintained in the range of about 0° to about 25° C. throughout substantially the entire reaction.
References Cited (Backward Citations)
US2920092A
Cited
US3472888A
Cited
US4210596A
Cited
US4238401A
Cited
US4360686A
Cited
US4375548A
Cited
US4448980A
Cited
US4634787A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-02-14 | 1992-08-15 | 1993-02-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-02-14 | 1996-08-15 | 1997-02-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-02-14 | 2000-08-15 | 2001-02-14 | $7700.00 | Window Closed / Lapsed |