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Highly branched perfluoroolefins, super-stable perfluoroalkyl radicals and production methods thereof

a perfluoroalkyl radical, superstable technology, applied in the field of high-branched perfluoroolefins, superstable perfluoroalkyl radicals and production methods thereof, can solve the problems of difficult to synthesize sterically complex perfluoroolefins, no other methods for perfluorosynthesis, and inapplicability of synthesis methods

Inactive Publication Date: 2004-07-01
NAT INST OF ADVANCED IND SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This method allows for the high-yield production of highly branched perfluoroolefins and super-stable perfluoroalkyl radicals, enhancing their stability and applicability as polymerization catalysts and in various industrial applications.

Problems solved by technology

However, perfluoro(2,4-dimethyl-3-isopropyl-3-pentyl) is obtained only in a trace amount by the synthesis method employing perfluoro(2,4-dimethyl-3-ethyl-3-pentyl), therefore this synthesis method is not practical.
No other methods for synthesizing perfluoro(2,4-dimethyl-3-isopropyl-3-pentyl) has hitherto been known.
Nevertheless, such a highly branched and sterically complicated perfluoroolefin is regarded to be very difficult to be synthesized, and no methods for synthesizing the same has hitherto been known.

Method used

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  • Highly branched perfluoroolefins, super-stable perfluoroalkyl radicals and production methods thereof
  • Highly branched perfluoroolefins, super-stable perfluoroalkyl radicals and production methods thereof
  • Highly branched perfluoroolefins, super-stable perfluoroalkyl radicals and production methods thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Perfluoro(2,4-dimethyl-3-isopropyl-2-pentene)

[0103] 1 mmol (450 mg) of a hexafluoropropene trimer mixture (containing 10% by weight of perfluoro(3-ethyl-2,4-dimethyl-2-pentene)) whose main component was perfluoro(4-methyl-3-isopropyl-2-pentene) and 1.1 mmol (23.4 mg) of trifluoromethyltrimethylsilane were weighed into a 10-ml fluororesin-made reaction container, and 1 ml of dimethyl formamide and 0.3 mmol of acidic potassium fluoride (KHF.sub.2) were added. A fluororesin-made magnetic stirrer was placed therein, and the mixture was stirred vigorously for 1 hour at room temperature. The transparent lower perfluorocarbon layer was separated into each component by preparative gas chromatography (using a column whose mobile phase was Fomblin), and the structure was identified by .sup.19F-NMR. The yield of a main product perfluoro(2,4-dimethyl-3-isopropyl-2-pentene) calculated on the basis of the ratio of the peak areas in the gas chromatography using a capillary column (NB-...

example 2

Synthesis of Perfluoro(2,4-dimethyl-3-isopropyl-2-pentene)

[0111] 1 mmol (450 mg) of a hexafluoropropene trimer mixture (containing 10% by weight of perfluoro(3-ethyl-2,4-dimethyl-2-pentene)) whose main component was perfluoro(4-methyl-3-isopropyl-2-pentene) and 4.0 mmol (568.8 mg) of trifluoromethyltrimethylsilane were weighed into a 10-ml fluororesin-made reaction container, and 1 ml of dimethyl formamide and 0.1 mmol of acidic potassium fluoride (KHF.sub.2, 7.8 mg) were added. A fluororesin-made magnetic stirrer was placed therein, and the mixture was stirred vigorously for 1 hour at room temperature. The transparent lower perfluorocarbon layer was analyzed by gas chromatography using a capillary column (NB-1, 0.25 .mu.m, 1.5 mm ID.times.60 m). The yields of the main product perfluoro(2,4-dimethyl-3-isopropyl-2-pentene) and perfluoro(2,4,4-trimethyl-3-isopropyl-2-pentene) were 63.5% by weight and 36.5% by weight, respectively.

[0112] Accordingly, it was revealed that the reaction c...

example 3

Selective Synthesis of Perfluoro(2,4-dimethyl-3-isopropyl-2-pentene)

[0113] 1 mmol (450 mg) of a hexafluoropropene trimer mixture (containing 10% by weight of perfluoro(3-ethyl-2,4-dimethyl-2-pentene)) whose main component was perfluoro(4-methyl-3-isopropyl-2-pentene) and 2.0 mmol (284.4 mg) of trifluoromethyltrimethylsilane were weighed into a 10-ml fluororesin-made reaction container, then 1 ml of 1,3-dimethyl-2-imidazol-idinone and 0.1 mmol of acidic potassium fluoride (KHF.sub.2, 7.8 mg) were added therein. A fluororesin-made magnetic stirrer was placed and the mixture was stirred vigorously for 1 hour at room temperature, and then 1.0 mmol of trifluoromethyltrimethylsilane (142.2 mg) and 0.1 mmol of acidic potassium fluoride (KHF.sub.2, 7.8 mg) were added and the mixture was further stirred vigorously for 1 hour at room temperature. After completion of the reaction, the transparent lower perfluorocarbon layer was analyzed by gas chromatography using a capillary column (NB-1, 0.2...

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Abstract

The present invention is to provide a method for producing a highly branched perfluoroolefin conveniently in a high yield, a novel highly branched perfluoroolefin, a method for producing a super-stable perfluoroalkyl radical and a novel super-stable perfluoroalkyl radical. The present invention is a production method of a perfluoroolefin which comprises reacting a hexafluoropropene trimer with a trialkylperfluoroalkylsilane in an aprotic polar solvent using a fluoride ion as a catalyst.

Description

[0001] The present invention relates to a highly branched perfluoroolefin, a production method of the highly branched perfluoroolefin comprising reacting a hexafluoropropene trimer with a trialkylperfluoroalkylsilane, a super-stable perfluoroalkyl radical and a method for producing a super-stable perfluoroalkyl radical by fluorinating the highly branched perfluoroolefin.PRIOR ART[0002] As a super-stable perfluoroalkyl radical which is highly stable, Japanese Kokai Publication Hei-1-29175, for example, discloses perfluoro(2,4-dimethyl-3-isopropyl-3-pentyl) and the like.[0003] In this gazette, it is described that perfluoro(2,4-dimethyl-3-isop-ropyl-3-pentyl) generates a free trifluoromethyl radical by, for example, heating, and this free trifluoromethyl radical can be employed, for example, as a polymerization catalyst.[0004] A super-stable perfluoroalkyl radical is known to be obtained, for example, by fluorinating a corresponding perfluoroolefin. In this case, the perfluoroolefin a...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07B61/00C07C17/04C07C17/26C07C17/263C07C19/08C07C21/18
CPCC07C17/04C07C17/263C07C19/08C07C21/18
Inventor ONO, TAIZONISHIDA, MASAKAZUOKAZAKI, MASAHARUTORIYAMA, KAZUMISHIMIZU, TETSUO
Owner NAT INST OF ADVANCED IND SCI & TECH
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