The present application provides a hydrodefluorination process for the preparation of hydrofluoroalkenes by catalyzed substitution of one or more F atoms of a C2-C30 fluoroalkene, or a C2-C10 fluoroalkene, with one or more H atoms using a hydride source, such as a silane, and copper catalyst. During this process at least one CF bond in the fluoroakene is converted to a CH bond. The process is useful in the manufacture of hydrofluoroalkenes, such as hydrofluoroalkenes employed as, for example, refrigerants and blowers. Also provided are precatalyst compositions for performing the process, and formulations manufactured from hydrofluoroalkenes produced using the process.

A hydrofluoroolefin compound is represented by the following general formula (I): where R.sub.f is a linear or branched perfluorinated alkyl group containing 2-10 carbon atoms and optionally contains (i) at least one catenated heteroatom selected from O or N; or (ii) a ring structure having 3 to 6 ring carbon atoms that optionally contains one or more catentated heteroatoms selected from O or N.

##STR00001##

A hydrofluoroolefin compound is represented by the following general formula (I): where R.sub.f is a linear or branched perfluorinated alkyl group containing 2-10 carbon atoms and optionally contains (i) at least one catenated heteroatom selected from O or N; or (ii) a ring structure having 3 to 6 ring carbon atoms that optionally contains one or more catentated heteroatoms selected from O or N.

##STR00001##

A hydrofluoroolefin compound represented by the following general formula (I): where, Rh is CHCH.sub.2 or C(CH.sub.3)CH.sub.2; and (i) x is O; n is 1; Y is F; Rf.sub.2 is F; and Rf.sub.1 is a linear or branched fluorinated alkyl group having 1-10 carbon atoms and optionally includes one or more catenated heteroatoms selected from O, N, and S; or ({umlaut over ()}) x is N, n is 2, Y is F or CF.sub.3; Rf.sub.2 is F or CF.sub.3; and (a) each Rf.sub.1 is bonded to x, and is independently a linear or branched fluorinated alkyl group having 1-8 carbon atoms and optionally includes one or more catenated heteroatom selected from O, N or S; or (e) the Rf.sub.1 groups are bonded together to form a ring structure having 4 to 8 carbon atoms that optionally includes one or more catenated heteroatoms selected from O, N, or S; with the proviso that when YCF.sub.3, then Rf.sub.2F. ##STR00001##

A hydrofluoroolefin compound represented by the following general formula (I): where, Rh is CHCH.sub.2 or C(CH.sub.3)CH.sub.2; and (i) x is O; n is 1; Y is F; Rf.sub.2 is F; and Rf.sub.1 is a linear or branched fluorinated alkyl group having 1-10 carbon atoms and optionally includes one or more catenated heteroatoms selected from O, N, and S; or ({umlaut over ()}) x is N, n is 2, Y is F or CF.sub.3; Rf.sub.2 is F or CF.sub.3; and (a) each Rf.sub.1 is bonded to x, and is independently a linear or branched fluorinated alkyl group having 1-8 carbon atoms and optionally includes one or more catenated heteroatom selected from O, N or S; or (e) the Rf.sub.1 groups are bonded together to form a ring structure having 4 to 8 carbon atoms that optionally includes one or more catenated heteroatoms selected from O, N, or S; with the proviso that when YCF.sub.3, then Rf.sub.2F. ##STR00001##

This disclosure relates generally to fluorinated ether compounds and the synthesis thereof. More particularly, this disclosure relates to fluorinated ether based thermal management fluids suitable for use managing heat in battery systems through direct cooling, such as lithium-ion batteries used in electric vehicles, electric motors, and power electronics, methods of using such thermal management fluids, and systems including such thermal management systems.

This disclosure relates generally to fluorinated ether compounds and the synthesis thereof. More particularly, this disclosure relates to fluorinated ether based thermal management fluids suitable for use managing heat in battery systems through direct cooling, such as lithium-ion batteries used in electric vehicles, electric motors, and power electronics, methods of using such thermal management fluids, and systems including such thermal management systems.

Described herein is an unsaturated fluorinated compound of formula (I) where X is O or N; Y is F or H; Z is F or CF.sub.3; and A is F or CF.sub.3 wherein when X is O, then n is 1, Y is H, Z is F, A is F, and Rf is a linear or branched perfluorinated alkyl group comprising 1 to 10 carbon atoms and optionally comprising at least one catenated O or N; and when X is N, then n is 2 and each Rf group are (i) independently selected from a linear or branched perfluorinated alkyl group comprising 1 to 8 carbon atoms and optionally comprising at least one catenated O or N; or (ii) bonded together to form a ring structure comprising 4 to 8 carbon atoms and optionally comprising at least one catenated O or N with the proviso that when Z is CF.sub.3 then A is F and when A is CF.sub.3 then Z is F and methods of making and using the same.

##STR00001##

Described herein is an unsaturated fluorinated compound of formula (I) where X is O or N; Y is F or H; Z is F or CF.sub.3; and A is F or CF.sub.3 wherein when X is O, then n is 1, Y is H, Z is F, A is F, and Rf is a linear or branched perfluorinated alkyl group comprising 1 to 10 carbon atoms and optionally comprising at least one catenated O or N; and when X is N, then n is 2 and each Rf group are (i) independently selected from a linear or branched perfluorinated alkyl group comprising 1 to 8 carbon atoms and optionally comprising at least one catenated O or N; or (ii) bonded together to form a ring structure comprising 4 to 8 carbon atoms and optionally comprising at least one catenated O or N with the proviso that when Z is CF.sub.3 then A is F and when A is CF.sub.3 then Z is F and methods of making and using the same.

##STR00001##

Disclosed is a fluoropolyether compound comprising a C.sub.4-10 aliphatic hydrocarbon chain present in the middle of the fluoropolyether compound and at least two perfluoropolyethers.