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Process for the preparation of perfluorinated cis-alkene

A cis-alkene, perfluorinated technology, applied in chemical instruments and methods, halogenated hydrocarbon preparation, organic chemistry, etc., can solve the problems of quinoline affecting results, undesired toxicity, etc.

Inactive Publication Date: 2011-06-29
HONEYWELL INT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The amines, while commonly used to increase reaction selectivity, are undesirable from the standpoint of their toxicity
The quality of the quinoline used may also affect the results

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] A 1 liter autoclave was charged with 2.0 g of catalyst (5% palladium on calcium carbonate, poisoned with 3.5% lead) and 160 mL of ethanol. The autoclave contents were then cooled to -78°C. Air was removed by pressurizing to 60 psi (434 kPa) with nitrogen followed by evacuation. This sequence is repeated two more times. Hexafluoro-2-butyne (32 g) was then added and the contents were heated to 25°C. Hydrogen was added to a pressure of 90 psig (651 kPa) and this pressure was maintained at a reaction temperature of 25-28°C for about 20 hours. The autoclave contents were cooled again with the aid of a -78°C bath before hydrogen evolution. The autoclave contents were distilled to obtain 31.6 g of 97% pure cis-hexafluoro-2-butene (97.5% yield). Three such preparations were performed and the combined material was redistilled to obtain the desired butene, bp 30-32° C., with a purity greater than 99.9% (H NMR: 6.56 ppm; F NMR: -60.17 ppm).

Embodiment 2

[0032] Example 2 was performed in a manner similar to Example 1, except that the ratio of hexafluoro-2-butyne to catalyst was doubled, and the hydrogen pressure was reduced to a maximum of 60 psig (434 kPa). Got similar results.

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Abstract

A process for the preparation of perfluorinated cis-alkene comprises: reducing a perfluorinated alkyne with hydrogen over a palladium catalyst in the presence of a non-aromatic amine catalyst modifier to form a product which comprises a perfluorinated cis-alkene, wherein the perfluorinated alkynes has a general formula structure Rf-C C-Rf, wherein Rf is a perfluorinated alkyl group having a carbon number in the range between about 1 to 6.

Description

technical field [0001] This disclosure relates to processes for the preparation of perfluorinated cis-alkenes, and more particularly, to the preparation of cis-1,1,1,4,4,4-hexafluoro-2-butene method. Background technique [0002] Fluorocarbon-based fluids have found widespread use in industry in a number of applications, including as refrigerants, aerosol propellants, blowing agents, heat transfer media, and gaseous dielectrics. Due to the suspected environmental concerns associated with the use of some of these fluids, including the relatively high global warming potentials (GWP) associated therewith, it is desirable to use fluids with the lowest possible greenhouse warming potential and zero ozone depletion Potential (ODP) of the fluid. Therefore, there is considerable interest in developing more environmentally friendly materials for the above-mentioned applications. [0003] Fluorinated butenes, which have zero ozone depletion and low global warming potential, have be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/354B01J23/44C07C21/18B01J23/04B01J23/745
CPCC07C21/18B01J23/58C07C17/354B01J23/628B01J23/04B01J23/44
Inventor M·范德皮尤J-J·马
Owner HONEYWELL INT INC