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

A technology of trifluoroethyl difluoromethyl ether and high yield, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc.

Inactive Publication Date: 2007-11-07
PIRAMAL CRITICAL CARE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with a 1:1 ratio of these reactants, the conversion was only 18% and the yield was 61%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 184 g CF 3 CHClOCHF 2 (1 mole) with 4.4 g of SbF 5 (2.4% by weight) were mixed, and anhydrous hydrogen fluoride was added while stirring the reaction mixture at 15-25°C. The effluent HCl gas formed in the reaction was directed to the water scrubber via a "dry ice" condenser to monitor the progress of the reaction and facilitate the determination of when the reaction was complete. The reaction is a slow but steady endothermic reaction. 12 grams of hydrogen fluoride (0.6 moles) were added over about six hours. At the end of this period, no additional HCl gas was collected in the scrubber, indicating that all the added hydrogen fluoride had reacted. The recovered material was washed with water to give 160 g, which was analyzed by gas chromatography. About 62% CF 3 CHFOCHF 2 and about 38% CF 3 CHClOCHF 2 (ie unreacted raw materials) and four minor components, all at 0.05% or less. CF calculated from gas chromatography 3 CHCFOCHF 2 The molar amount of is 0.59 mol...

Embodiment 2

[0029] 239 g CF 3 CHClOCHF 2 (1.30 mol) with 6 g of SbF 5 (2.5% by weight) were mixed, and anhydrous hydrogen fluoride was added at 15-20°C. The effluent from the reaction was directed via a "dry ice" condenser to a water scrubber in order to collect and titrate the HCl formed in the reaction. The reaction is slow, steady and endothermic. The reaction was terminated after 1.03 moles of HCl (determined by a standard NaOH titration scrubber) were liberated from the reaction. The reaction mixture was washed with ice water to obtain 203 g. It was analyzed by gas chromatography and showed a CF of 76% 3 CHFOCHF 2 and 23% of unreacted starting material (CF 3 CHClOCHF 2 ). The conversion calculated by gas chromatography was 80.5%, and the yield was 87.8%, based on the reacted starting materials. Therefore, the effect of hydrogen fluoride on CF in this example 3 CHClOCHF 2 The ratio of 0.79:1 gave a conversion of 80.5% and a yield of 87.8%. By comparison, U.S. Patent No. 5...

Embodiment 3

[0031] 156 g CF 3 CHClOCHF 2 (0.85 mol) with 3.9 g of SbF 5 (2.5% by weight) were mixed, and anhydrous hydrogen fluoride was added at 0-30°C. The effluent from the reaction was directed via a "dry ice" condenser to a water scrubber in order to collect and titrate the HCl formed in the reaction. The reaction is slow, steady and endothermic. The reaction was terminated after titration with 0.5 molar HCl in the scrubber. The product weighed 140 grams. Standard base titration determined little residual acid in the product. The product was analyzed by gas chromatography, showing a CF of 52% 3 CHFOCHF 2 and 48% of unreacted starting material (CF 3 CHClOCHF 2 ). The conversion calculated from the chromatography was 57% and the yield was 89.3%. In this example the hydrogen fluoride to CF 3 CHClOCHF 2 The ratio of 0.59:1 gave a conversion of 57% and a yield of 89.3%. These results are superior to those reported in U.S. Patent No. 5,026,924, where a 0.5:1 ratio of hydrogen...

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PUM

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Abstract

A method for the preparation of 1,2,2,2-tetrafluoroethyl difluoromethyl ether (CF3CHFOCHF2, Deflurane) is provided, which comprises reacting CF3CHCIOCHF2 (isoflurane) and hydrogen fluoride in the presence of antimony pentafluoride such that deflurane is formed.

Description

[0001] Related Application Cross Reference [0002] Applicants claim priority to U.S. Provisional Application 60 / 628,708, filed November 17, 2004 and entitled "Process for Production of 1,2,2,2-Tetrafluoro Ethyl Difluoro Methyl Ether," the contents of which are incorporated by reference at this. technical field [0003] The present invention relates to the field of inhalational anesthetics. More specifically, the present invention relates to an improved process for the preparation of 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane). Background technique [0004] In general, what plagues the fluorination of alkanes and alkanes-containing compounds is the inability to effectively monofluorinate the reaction substrate at the desired site, thereby reducing the reaction conversion (i.e., the proportion of unreacted substrate) and the yield (the proportion of the reaction substrate undergoing fluorin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/22
CPCC07C41/22C07C43/123C07C41/18
Inventor R·C·特雷尔J·A·乐文森
Owner PIRAMAL CRITICAL CARE
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