Patent US5196600A successfully refreshed from Google Patents.
US5196600A
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Synthesis of fluorinated dimethyl ethers
Assignee: Hampshire Chemical Corp
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Filing: 1992-03-25
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Granted: 1993-03-23
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Expires: 2012-03-25
Abstract
Abstract A novel process is disclosed for the synthesis of fluorinated dimethyl ethers of the formula CF 2 HOCCl x F y H 3- (x+y) wherein x is 0, 1 or 2; y is 1, 2 or 3; and wherein the total x+y is 1, 2 or 3. The process involves chlorination of methyl difluoromethyl ether to form a chlorinated reaction product, including at least one compound of the formula CF 2 HOCH 3-z Cl z , wherein z is 1, 2 or 3, which compound is then fluorinated with HF and/or an antimony salt and with or without separation from the chlorinated reaction product, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.
Inventors
- 👤 Gerald J. O'Neill
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 07:16
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/18; C07C41/22; C07C41/16
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
137 words
A process for the preparation of fluorinated dimethyl ethers of the formula CF 2 HOCCl x F y H 3- (x+y), wherein x is 0, 1 or 2 and y is 1, 2 or 3 and wherein the total x+y is 1, 2 or 3, said process comprising: chlorinating CHF 2 OCH 3 by reacting said CHF 2 OCH 3 with chlorine to form a chlorinated admixture containing at least one compound of the formula CF 2 HOCH 3-z Cl z , wherein z is 1, 2 or 3; and fluorinating said at least one compound of the formula CF 2 HOCH 3-z Cl z , with hydrogen fluoride in the absence of a catalyst to obtain a fluorinated admixture containing at least one compound of a formula CF 2 HOCH 3-z F y Cl z-y .
Claim 2
Dependent Claim
137 words
A process for the preparation of fluorinated dimethyl ethers of the formula CF 2 HOCCl x F y H 3- (x+y), wherein x is 0, 1 or 2 and y is 1, 2 or 3 and wherein the total x+y is 1, 2 or 3, said process comprising: chlorinating CHF 2 OCH 3 by reacting said CHF 2 OCH 3 with chlorine to form a chlorinated admixture containing at least one compound of the formula CF 2 HOCH 3-z Cl z , wherein z is 1, 2 or 3; and fluorinating said at least one compound of the formula CF 2 HOCH 3-z Cl z , with hydrogen fluoride in the absence of a catalyst to obtain a fluorinated admixture containing at least one compound of a formula CF 2 HOCH 3-z F y Cl z-y .
Claim 3
Dependent Claim
32 words
A process in accordance with claim 1 wherein said chlorination step occurs in either a vapor or liquid phase and the chlorine is in the form of a liquid or a gas.
Claim 4
Dependent Claim
26 words
A process in accordance with claim 2 wherein said chlorination step is in the vapor phase and the chlorine is in the form of a gas.
Claim 5
Dependent Claim
28 words
A process in accordance with claim 1 wherein the hydrogen fluoride is selected from the group consisting of anhydrous hydrogen fluoride and hydrogen fluoride in an organic solvent.
Claim 6
Dependent Claim
42 words
A process in accordance with claim 1 wherein said at least one compound of the formula CF 2 HOCH 3-z Cl z is CF 2 HOCHCl 2 and said fluorinated reaction product includes CF 2 HOCF 2 H and CF 2 HOCHFCl.
Claim 7
Dependent Claim
65 words
A process in accordance with claim 1 wherein said at least one compound of the formula CF 2 HOCH 3-z Cl z is CHF 2 OCHCl 2 and said at least one compound of the formula CF 2 HOCCl x F y H 3- (x+y) is CHF 2 OCHF 2 and further comprising separating and recovering said CHF 2 OCHF 2 from said fluorinated admixture.
Claim 8
Dependent Claim
84 words
A process in accordance with claim 1 wherein said at least one compound of the formula CF 2 HOCH 3-z Cl z is CF 2 HOCCl 3 , and said at least one compound of the formula CF 2 HOCCl x F y H 3- (x+y) is selected from the group consisting of CF 2 HOCF 2 Cl and CF 2 HOCFCl 2 and further comprising separating and recovering said CF 2 HOCF 2 Cl and/or CF 2 HOCFCl 2 from said fluorinated mixture.
Claim 9
Dependent Claim
20 words
A process in accordance with claim 7 wherein said fluorinating involves reacting said CF 2 HOCCl 3 with anhydrous HF.
Claim 10
Dependent Claim
29 words
A process in accordance with claim 1 wherein said chlorination is conducted at a temperature and pressure sufficient to maintain said CF 2 HOCH 3 in a gaseous state.
Claim 11
Dependent Claim
29 words
A process in accordance with claim 1 further comprising reacting CHF 2 Cl with an alkali metal methoxide in solvent solution to form said CHF 2 OCH 3 .
Claim 12
Dependent Claim
24 words
A process in accordance with claim 6 wherein an admixture of CF 2 HOCH 3 and CHF 2 Cl is subjected to said chlorinating.
Claim 13
Dependent Claim
20 words
A process in accordance with claim 1 wherein the hydrogen fluoride is is hydrogen fluoride diluted with an organic solvent.
Claim 14
Dependent Claim
18 words
The process of claim 1 further comprising the chlorination step occurs in the presence of a reaction aid.
Claim 15
Dependent Claim
23 words
The process of claim 13 wherein the reaction aid is selected from the group consisting of light, heat, catalysts and free radical initiators.
Claim 16
Dependent Claim
61 words
A process for the preparation of fluorinated dimethyl ethers of the formula CF 2 HOCCl x F y H 3- (x+y), wherein x and y are each independently 0, 1, 2 or 3 and wherein the fluorination comprises reacting at least one compound of the formula CF 2 HOCH 3-z Cl z with hydrogen fluoride in the absence of a catalyst.
Claim 17
Dependent Claim
61 words
A process for the preparation of fluorinated dimethyl ethers of the formula CF 2 HOCCl x F y H 3- (x+y), wherein x and y are each independently 0, 1, 2 or 3 and wherein the fluorination comprises reacting at least one compound of the formula CF 2 HOCH 3-z Cl z with hydrogen fluoride in the absence of a catalyst.
Claim 18
Dependent Claim
15 words
A process in accordance with claim 15 wherein the hydrogen fluoride is in anhydrous form.
Claim 19
Dependent Claim
17 words
A process in accordance with claim 15 wherein the hydrogen fluoride is diluted with an organic solvent.
Claim 20
Dependent Claim
70 words
A process for the process for the preparation of fluorinated dimethyl ethers of the formula CF 2 HOCCl x F y H 3- (x+y), wherein x and y are each independently 0, 1, 2 or 3 and wherein the fluorination comprises reacting at least one compound of the formula CF 2 HOCH 3-z Cl z wherein z is 1, 2 or 3; with hydrogen fluoride diluted in an organic solvent.
Claim 21
Dependent Claim
70 words
A process for the process for the preparation of fluorinated dimethyl ethers of the formula CF 2 HOCCl x F y H 3- (x+y), wherein x and y are each independently 0, 1, 2 or 3 and wherein the fluorination comprises reacting at least one compound of the formula CF 2 HOCH 3-z Cl z wherein z is 1, 2 or 3; with hydrogen fluoride diluted in an organic solvent.
Claim 22
Dependent Claim
26 words
The process of claim 18 wherein the fluorination of CF 2 HOCH 3-z Cl z with the hydrogen fluoride occurs in the absence of a catalyst.
Claim 23
Dependent Claim
13 words
The process of claim 18 wherein the organic solvent is an aprotic solvent.
Claim 24
Dependent Claim
11 words
The process of claim 20 wherein the solvent is methyl pyrrolidone.
Claim 25
Dependent Claim
137 words
A process for the preparation of fluorinated dimethyl ethers of the formula CF 2 HOCCl x F y H 3- (x+y), wherein x is 0, 1 or 2 and y is 1, 2 or 3 and wherein the total x+y is 1, 2 or 3, said process comprising: chlorinating CHF 2 OCH 3 by reacting said CHF 2 OCH 3 with chlorine to form a chlorinated admixture containing at least one compound of the formula CF 2 HOCH 3-z Cl z , wherein z is 1, 2 or 3; and fluorinating said at least one compound of the formula CF 2 HOCH 3-z Cl z , with hydrogen fluoride in the absence of a catalyst to obtain a fluorinated admixture containing at least one compound of a formula CF 2 HOCH 3-z F y Cl z-y .
Claim 26
Dependent Claim
137 words
A process for the preparation of fluorinated dimethyl ethers of the formula CF 2 HOCCl x F y H 3- (x+y), wherein x is 0, 1 or 2 and y is 1, 2 or 3 and wherein the total x+y is 1, 2 or 3, said process comprising: chlorinating CHF 2 OCH 3 by reacting said CHF 2 OCH 3 with chlorine to form a chlorinated admixture containing at least one compound of the formula CF 2 HOCH 3-z Cl z , wherein z is 1, 2 or 3; and fluorinating said at least one compound of the formula CF 2 HOCH 3-z Cl z , with hydrogen fluoride in the absence of a catalyst to obtain a fluorinated admixture containing at least one compound of a formula CF 2 HOCH 3-z F y Cl z-y .
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) | 1996-03-22 | 1996-09-21 | 1997-03-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-03-22 | 2000-09-21 | 2001-03-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-03-22 | 2004-09-21 | 2005-03-23 | $7700.00 | Window Closed / Lapsed |