IP Library Patent Application 11281294
Patent Application
App. No. 11/281,294

Process for production of 1,2,2,2-tetrafluoro ethyl difluoro methyl ether

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Patent No.
US None
App. No.
11/281,294
Abstract

A method for the preparation of 1,2,2,2-tetrafluoroethyl difluoromethyl ether (CF 3 CHFOCHF 2 , Desflurane) is provided, which comprises reacting CF 3 CHClOCHF 2 (isoflurane) and hydrogen fluoride in the presence of antimony pentafluoride such that desflurane is formed.

Claims (26)

1 . A process for the preparation of Desflurane, said process comprising forming a mixture comprising 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether (CF 3 CHClOCHF 2 ), hydrogen fluoride and antimony pentafluoride, such that Desflurane is formed.

2 . A process as in claim 1 , wherein hydrogen fluoride is added in molar amounts in the range of from 0.1:1 to 1.5:1 moles of hydrogen fluoride per mole of (CF 3 CHClOCHF 2 ) charged to the reaction vessel.

3 . A process as in claim 1 , wherein the temperature of the reaction is in the range of about −10° C. to 30° C.

4 . A process as in claim 1 , wherein the temperature of the reaction is in the range of from about −7° C. to 18° C.

5 . A process as in claim 1 , wherein the mixture is formed by a process comprising:

a) combining said CF 3 CHClOCHF 2 with said antimony pentafluoride; and

b) adding hydrogen fluoride to said combined CF 3 CHClOCHF 2 and antimony pentafluoride while stirring.

6 . A process as in claim 1 , wherein the yield of Desflurane is 60% or greater.

7 . A process as in claim 6 , wherein the reaction conversion is 60% or greater.

8 . A process for the preparation of Desflurane comprising combining CF 3 CHClOCHF 2 , hydrogen fluoride and antimony pentafluoride, wherein the molar amount of hydrogen fluoride added per mole of CF 3 CHClOCHF 2 is in the range of from 0.1:1 to 1.5:1 and the quantity of antimony pentafluoride is preferably in the range of from 0.1 to 10 weight percent relative to the weight of CF 3 CHCIOCHF 2 ; wherein desflurane is formed.

9 . A process as in claim 8 wherein the molar amount of hydrogen fluoride added per mole of CF 3 CHClOCHF 2 is in the range of from 0 of 0.7:1 to 1.1:1 and the quantity of antimony pentafluoride is preferably in the range of from 2 to 2.5 weight % relative to the weight of CF 3 CHClOCHF 2 .

10 . A process as in claim 8 wherein the mixture is formed by a process comprising

a) combining said CF 3 CHClOCHF 2 with said antimony pentafluoride; and

b) adding hydrogen fluoride to said combined CF 3 CHClOCHF 2 and antimony pentafluoride while stirring.

11 . A process as in claim 8 wherein Desflurane is separated out from the reaction mixture.

12 . A process for the preparation of Desflurane comprising:

a) forming a mixture comprising CF 3 CHClOCHF 2 , and antimony pentafluoride; and hydrogen fluoride; and

b) adding hydrogen fluoride to the mixture at a rate approximately equal to or less than the rate at which the hydrogen fluoride reacts with the CF 3 CHClOCHF 2 to form Desflurane.

13 . A process as in claim 12 wherein the temperature of the reaction is in the range of from about −10 to 30° C.

14 . A process as in claim 12 wherein the temperature of the reaction is in the range of from about 15 to 25° C.

15 . A process as in claim 12 wherein the hydrogen fluoride is added at a rate in the range of from about 0.10 to 0.30 moles per hour per mole isoflurane charged to the reaction vessel.

16 . A process as in claim 12 wherein the HF is added at a rate in the range of from about 0.15 to 0.25 moles per hour per mole isoflurane charged to the reaction vessel.

17 . A process as in claim 12 , wherein the yield of Desflurane is 60% or greater.

18 . A process as in claim 12 , wherein the reaction conversion is 60% or greater.

19 . A process as in claim 12 wherein both yield and conversion are above 70%

20 . Desflurane formed by the process of claim 11.

Assignments (14)
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 10272794 PREVIOUSLY RECORDED AT REEL: 028427 FRAME: 0056. ASSIGNOR(S) HEREBY CONFIRMS THE RELEASE BY SECURED PARTY. Recorded Jul 10, 2015
From: CREDIT AGRICOLE CORPORATE AND INVESTMENT BANK, SINGAPORE
To: PIRAMAL CRITICAL CARE, INC.
Reel/Frame 036089/0033 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NAME OF THE ASSIGNEE PREVIOUSLY RECORDED AT REEL: 025599 FRAME: 0742. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 19, 2015
From: STANDARD CHARTERED BANK
To: PIRAMAL CRITICAL CARE, INC. AS SUCCESSOR BY MERGER TO MINRAD, INC.
Reel/Frame 036130/0555 →
RELEASE OF SECURITY INTEREST Recorded Jun 22, 2012
From: CREDIT AGRICOLE CORPORATE AND INVESTMENT BANK, SINGAPORE
To: PIRAMAL CRITICAL CARE, INC.
Reel/Frame 028427/0056 →
CHANGE OF NAME Recorded Feb 13, 2012
From: MINRAD INC.
To: PIRAMAL CRITICAL CARE, INC.
Reel/Frame 027695/0312 →
SECURITY INTEREST Recorded Jan 23, 2012
From: PIRAMAL CRITICAL CARE, INC.
To: CREDIT AGRICOLE CORPORATE AND INVESTMENT BANK SINGAPORE
Reel/Frame 027637/0840 →
RELEASE OF SECURITY INTEREST Recorded Dec 2, 2010
From: STANDARD CHARTERED BANK
To: PIRAMAL HEALTHCARE, INC., AS SUCCESSOR BY MERGER TO MINRAD, INC.
Reel/Frame 025599/0742 →
THIS IS A CORRECTIVE ASSIGNMENT FOR INTELLECTUAL SECURITY AGREEMENT DATED AS OF MARCH 23, 2009 BETWEEN MINRAD INC. AS GRANTOR AND STANDARD CHARTERED BANK AS SECURITY TRUSTEE FILED IN REEL 022440 AND FRAME 0478 ON MARCH 24, 2009. PATENT APPLICATION NUMBER 11/218,293 WAS INCORRECTLY ASSIGNED. THE CORRECT PATENT APPLICATION NUMBER SHOULD BE 11/281,293 Recorded Feb 10, 2010
From: MINRAD INC.
To: STANDARD CHARTERED BANK
Reel/Frame 023937/0402 →
SECURITY AGREEMENT Recorded Mar 24, 2009
From: MINRAD INC.
To: STANDARD CHARTERED BANK
Reel/Frame 022440/0478 →
RELEASE OF SECURITY INTEREST Recorded Dec 16, 2008
From: FIRST NIAGARA BANK
To: MINRAD INC.
Reel/Frame 021985/0117 →
TERMINATION OF SECURITY INTEREST IN PATENTS Recorded May 23, 2008
From: LAMINAR DIRECT CAPITAL, L.P.
To: MINRAD INC.
Reel/Frame 020986/0543 →
NOTICE OF GRANT OF SECURITY INTEREST Recorded Feb 25, 2008
From: MINRAD INC.
To: LAMINAR DIRECT CAPITAL L.P., AS AGENT
Reel/Frame 020550/0950 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE FROM ASSIGNMENT TO SECURITY AGREEMENT, PREVIOUSLY RECORDED ON REEL 019605 FRAME 0862. ASSIGNOR(S) HEREBY CONFIRMS THE COLLATERAL ASSIGNMENT OF PATENTS. Recorded Aug 8, 2007
From: MINRAD INC.
To: FIRST NIAGARA BANK
Reel/Frame 019658/0648 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2007
From: MINRAD INC.
To: FIRST NIAGARA BANK
Reel/Frame 019605/0862 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2006
From: TERRELL, ROSS C.; LEVINSON, JOSHUA A.
To: MINRAD INC.; MINRAD INC.
Reel/Frame 017903/0045 →