Perfluoroolefin-hydrocarbon hybrid compound, method of producing the same and method of producing perfluoroalkyl radical

A method for producing the perfluoroolefin-hydrocarbon hybrid compound as defined by the following general formula (1) or by the following general formula (2):

• [(CF3)2CX] [(CF3)2CY]C═C(CF3)Z (1)
• wherein X, Y and Z may be the same or different, and independently represent F or R, except that all of X, Y and Z are F, wherein R represents straight chain or branched alkyl having from 1 to 15 carbon atoms and aryl groups having from 1 to 15 carbon atoms;
• or
• [(CF3)2CX] [(CF3)YZ]C═C(CF3)2 (2)
• wherein X, Y and Z may be the same or different, and independently represent F or R, except that all of X, Y and Z are −F, wherein R represents straight chain or branched alkyl having from 1 to 15 carbon atoms and aryl groups having from 1 to 15 carbon atoms, wherein a hexafluoropropene trimer is reacted with an organometallic compound of alkali metal or alkali earth metal, said organometallic compound being represented by the following general formula (3):
• RG (3)
• wherein R represents a straight chain or branched alkyl and aryl group having from 1 to 15 carbon atoms;
• and G represents at least one of Li, Na, K, MgX, ZnX and CdX, wherein X represents Cl, Br and I.

A method for producing a perfluoroalkyl radical, wherein a perfluoroolefin-hydrocarbon hybrid compound, as defined by the following general formula (1) or by the following general formula (2):

• [(CF3)2CX][(CF3)2CY]C═C(CF3)Z (1)
• wherein X, Y and Z may be the same or different, and independently represent F or R, except that all of X, Y and Z are F, wherein R represents straight chain or branched alkyl having from 1 to 15 carbon atoms and aryl groups having from 1 to 15 carbon atoms;
• or
• [(CF3)2CX] [(CF3)YZ]C═C(CF3)2 (2)
• wherein X, Y and Z may be the same or different, and independently represent F or R, except that all of X, Y and Z are F, wherein R represents straight chain or branched alkyl having from 1 to 15 carbon atoms and aryl groups having from 1 to 15 carbon atoms, is fluorinated to form a highly stable perfluoroalkyl radical represented by the following general formula (1R):
• [(CF3)2CRf1] [(CF3)2CRf2]Ra—CF(CF3)Rf3 (1R)
• wherein Ra represents a carbon atom having one unpaired electron;
• and Rf1, Rf2 and Rf3 may be the same or different, and independently represent F or Rf, except that all of Rf1, Rf2 and Rf3 are F, wherein Rf represents a perfluoroalkyl group having from 1 to 15 carbon atoms or perfluorocycloalkyl group having from 1 to 15 carbon atoms.

A method for producing a perfluoroalkyl radical, wherein said perfluoroolefin-hydrocarbon hybrid compound as defined by the following general formula (1) or by the following general formula (2):

• [(CF3)2CX] [(CF3)2CY]C═C(CF3)Z (1)
• wherein X, Y and Z may be the same or different, and independently represent F or R, excepting that all of X, Y and Z are F, wherein R represents straight chain or branched alkyl having from 1 to 15 carbon atoms and aryl groups having from 1 to 15 carbon atoms;
• or
• [(CF3)2CX] [(CF3)YZ]C═C(CF3)2 (2)
• wherein X, Y and Z may be the same or different, and independently represent F or R, except that all of X, Y and Z are F, wherein R represents straight chain or branched alkyl having from 1 to 15 carbon atoms and aryl groups having from 1 to 15 carbon atoms, is, fluorinated to form a highly. stable perfluoroalkyl radical represented by the following general formula (2R):
• [(CF3)2CRf1][(CF3)CRf2Rf3]Ra—CF(CF3)2 (2R)
• wherein Ra represents a carbon atom having one unpaired electron;
• and Rf1, Rf2 and Rf3 may be the same or different, and independently represent F or Rf, except that all of Rf1, Rf2 and Rf3 are F, wherein Rf represents a perfluoroalkyl group having from 1 to 15 carbon atoms or perfluorocycloalkyl group having from 1 to 15 carbon atoms.