Provided is a novel compound that is expected to be used as a solvent, a cleaning agent, a blowing agent, an intermediate for a functional material, and so forth, as well as a production method therefor and uses thereof As the novel compound, 1,2-dichoro-1-(2,2,2-trifluoroethoxy)ethylene is provided. This compound can be produced, for example, by allowing an addition reaction between 2,2,2-trifluoroethanol and trichloroethylene in the presence of a base.

Provided is a novel compound that is expected to be used as a solvent, a cleaning agent, a blowing agent, an intermediate for a functional material, and so forth, as well as a production method therefor and uses thereof As the novel compound, 1,2-dichoro-1-(2,2,2-trifluoroethoxy)ethylene is provided. This compound can be produced, for example, by allowing an addition reaction between 2,2,2-trifluoroethanol and trichloroethylene in the presence of a base.

A hydrofluoroolefin ether represented by the general Formula (I), compositions that include such compounds, and apparatuses and methods for use that include such compositions and compounds, wherein Formula (I) is represented by: R.sub.f—O—CH.sub.2CH═CHCH.sub.2—O—R.sub.f (I) wherein each Rf group is independently a linear, branched, and/or cyclic perfluoroalkyl group having 2 to 9 carbon atoms and optionally further including 1 to 3 nitrogen and/or oxygen catenary heteroatoms.

R.sub.f—O—CH.sub.2CH═CHCH.sub.2—O—R.sub.f   (I)

A hydrofluoroolefin ether represented by the general Formula (I), compositions that include such compounds, and apparatuses and methods for use that include such compositions and compounds, wherein Formula (I) is represented by: R.sub.f—O—CH.sub.2CH═CHCH.sub.2—O—R.sub.f (I) wherein each Rf group is independently a linear, branched, and/or cyclic perfluoroalkyl group having 2 to 9 carbon atoms and optionally further including 1 to 3 nitrogen and/or oxygen catenary heteroatoms.

R.sub.f—O—CH.sub.2CH═CHCH.sub.2—O—R.sub.f   (I)

A hydrofluoroolefin ether represented by the general Formula (I), compositions that include such compounds, and apparatuses and methods for use that include such compositions and compounds, wherein Formula (I) is represented by: R.sub.f—O—CH.sub.2CH═CHCH.sub.2—O—R.sub.f (I) wherein each Rf group is independently a linear, branched, and/or cyclic perfluoroalkyl group having 2 to 9 carbon atoms and optionally further including 1 to 3 nitrogen and/or oxygen catenary heteroatoms.

R.sub.f—O—CH.sub.2CH═CHCH.sub.2—O—R.sub.f   (I)

The invention discloses a method for preparation of alkylated, fluoro alkylated, chloro alkylated and fluorochloro alkylated compounds by a heterogeneous Co-catalysed alkylation or fluoro, chloro and fluorochloro alkylation with alkyl halides, fluoro alkyl halides, chloro alkyl halides or fluorochloro alkyl halides respectively.

The invention discloses a method for preparation of alkylated, fluoro alkylated, chloro alkylated and fluorochloro alkylated compounds by a heterogeneous Co-catalysed alkylation or fluoro, chloro and fluorochloro alkylation with alkyl halides, fluoro alkyl halides, chloro alkyl halides or fluorochloro alkyl halides respectively.

A compound represented by the following formula (A1) or (A2):

G.sup.1-(CH.sub.2).sub.m1CHX.sup.1(CH.sub.2).sub.n1-M Formula (A1)

M-(CH.sub.2).sub.n2CHX.sup.1(CH.sub.2).sub.m2-G.sup.2(CH.sub.2).sub.m3CHX.sup.1(CH.sub.2).sub.n3-M Formula (A2).

Where in the formula (A1) and (A2), G.sup.1, G.sup.2, X.sup.1, M, n1, n2, n3, m1, m2, and m3 are as defined in the disclosure. A method for producing a compound represented by the following formula (B1) or (B2), where M in the compound of formula (A1) or (A2) is converted into a hydrogen or hydrocarbon group represented by R.sup.3:

G.sup.1-(CH.sub.2).sub.m1CHX.sup.1(CH.sub.2).sub.n1R.sup.3 Formula (B1)

R.sup.3(CH.sub.2).sub.n2CHX.sup.1(CH.sub.2).sub.m2-G.sup.2-(CH.sub.2).sub.m3CHX.sup.1(CH.sub.2).sub.n3R.sup.3 Formula (B2).

Where in the formulas B1 and B2, G.sup.1, G.sup.2, X.sup.1, R.sup.3, n1, n2, n3, m1, m2, and m3 are as defined in the disclosure.

An object is to provide a method for producing a fluorine-containing compound by using an easily available compound under relatively mild reaction conditions to produce a fluorine-containing compound, and a method for producing a surface treatment agent using the fluorine-containing compound obtained by the production method.

A method for producing a fluorine-containing compound represented by the following formula (C1) or (C2), the method including: reacting a compound represented by the following formula (A1) or (A2) with a compound represented by the following formula (B1) or (B2).

G.sup.1-L.sup.1-CR.sup.1R.sup.2X.sup.1Formula (A1)

X.sup.2CR.sup.3R.sup.4-L.sup.2-G.sup.2-L.sup.3-CR.sup.5R.sup.6X.sup.2Formula (A2)

R.sup.11ZnR.sup.12Formula (B1)

R.sup.11BR.sup.13R.sup.14Formula (B2)

G.sup.1-L.sup.1-CR.sup.1R.sup.2R.sup.11Formula (C1)

R.sup.11CR.sup.3R.sup.4-L.sup.2-G.sup.2-L.sup.3-CR.sup.5R.sup.6R.sup.11Formula (C2) where, each reference sign in the formula is as described in the specification.

The present invention relates to an unsaturated fluorinated ether or amine compound of formula (I) with low global warming potential and method of making the compound (I), where R.sub.H.sup.1 is and R.sub.H.sup.2 are independently selected from H or CH.sub.3, wherein when R.sub.H.sup.1 is CH.sub.3 then R.sub.H.sup.2 is H and when R.sub.H.sup.2 is CH.sub.3, then R.sub.H.sup.1 is H; X is O or N and when X is O, then n is 1 and R.sub.f is a linear or branched perfluorinated alkyl group comprising 1-10 carbon atoms and optionally comprising at least one catenated O or N atom; X is N, then n is 2 and (i) each R.sub.f is independently selected from a linear or branched perfluorinated alkyl group comprising 1-8 carbon atoms and optionally comprising at least one catenated O or N atom, or (ii) the two R.sub.f's are bonded together to form a ring structure optionally comprising at least one catenated O or N atom, wherein the ring of the ring structure consists of 5-7 atoms, no more than 10 carbon atoms, and is perfluorinated. The applications of the compound include solvent cleaning, electrolyte solvents or additives, heat transfer, and vapour phase soldering.