Disclosed is a process for the preparation of cis-1,1,1,4,4,4-hexafluoro-2-butene comprising contacting 1,1,1-trifluorotrichloroethane with hydrogen in the presence of a catalyst comprising ruthenium to produce a product mixture comprising 1316mxx, recovering said 1316mxx as a mixture of Z- and E-isomers, contacting said 1316mxx with hydrogen, in the presence of a catalyst selected from the group consisting of copper on carbon, nickel on carbon, copper and nickel on carbon and copper and palladium on carbon, to produce a second product mixture, comprising E- or ZCFC-1326mxz, and subjecting said second product mixture to a separation step to provide E- or Z-1326mxz. The E- or Z-1326mxz can be dehydrochlorinated in an aqueous basic solution with an alkali metal hydroxide in the presence of a phase transfer catalyst to produce hexafluoro-2-butyne, which can then be selectively hydrogenated to produce Z-1,1,1,4,4,4-hexafluoro-2-butene using either Lindlar's catalyst, or a palladium catalyst further comprising a lanthanide element or silver.

An apparatus for heat transfer includes a device and a mechanism for transferring heat to or from the device. The mechanism for transferring heat includes a working fluid that includes a hexafluoropropylene trimer having Structural Formula (1) The hexafluoropropylene trimer having Structural Formula (1) is present in the working fluid in an amount of at least 85% by weight, based on the total weight of hexafluoropropylene trimer in the working fluid.

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An apparatus for heat transfer includes a device and a mechanism for transferring heat to or from the device. The mechanism for transferring heat includes a working fluid that includes a hexafluoropropylene trimer having Structural Formula (1) The hexafluoropropylene trimer having Structural Formula (1) is present in the working fluid in an amount of at least 85% by weight, based on the total weight of hexafluoropropylene trimer in the working fluid.

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An apparatus for heat transfer includes a device and a mechanism for transferring heat to or from the device. The mechanism for transferring heat includes a working fluid that includes a hexafluoropropylene trimer having Structural Formula (1) The hexafluoropropylene trimer having Structural Formula (1) is present in the working fluid in an amount of at least 85% by weight, based on the total weight of hexafluoropropylene trimer in the working fluid.

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It is an objet to provide an oil extraction agent that is used in an oil concentration meter, that can be manufactured at low cost, that has a high oil extraction efficiency, and whose burden on the environment is small. Trimeric or higher oligomers of chlorotrifluoroethylene are contained in the overall oil extraction agent in a range between 35% by weight or more and 100% by weight or less.

Disclosed in the present disclosure are a method and system for producing hexafluoro-1,3-butadiene. It includes: under the action of a catalyst, chlorotrifluoroethylene reacting with hydrogen gas in a first reactor to obtain a mixture, the mixture entering a rectification apparatus, trifluoroethylene obtained by rectification entering a second reactor and reacting with bromine under light to obtain 1,2-dibromo-trifluoroethane; in a third reactor pre-loaded with the 1,2-dibromo-trifluoroethane, adding the 1,2-dibromo-trifluoroethane and solid alkali, and performing reaction to obtain bromotrifluoroethylene; and adding the bromotrifluoroethylene to a fourth reactor holding with zinc powder, an initiator and an organic solvent for reaction, so as to obtain a trifluoroethenyl zinc bromide solution, performing filtration, and then adding a coupling agent for a coupling reaction, so as to obtain hexafluoro-1,3-butadiene. The present disclosure has the advantages of high safety, good in catalytic stability and high in process selectivity, and can achieve continuous production.

Disclosed in the present disclosure are a method and system for producing hexafluoro-1,3-butadiene. It includes: under the action of a catalyst, chlorotrifluoroethylene reacting with hydrogen gas in a first reactor to obtain a mixture, the mixture entering a rectification apparatus, trifluoroethylene obtained by rectification entering a second reactor and reacting with bromine under light to obtain 1,2-dibromo-trifluoroethane; in a third reactor pre-loaded with the 1,2-dibromo-trifluoroethane, adding the 1,2-dibromo-trifluoroethane and solid alkali, and performing reaction to obtain bromotrifluoroethylene; and adding the bromotrifluoroethylene to a fourth reactor holding with zinc powder, an initiator and an organic solvent for reaction, so as to obtain a trifluoroethenyl zinc bromide solution, performing filtration, and then adding a coupling agent for a coupling reaction, so as to obtain hexafluoro-1,3-butadiene. The present disclosure has the advantages of high safety, good in catalytic stability and high in process selectivity, and can achieve continuous production.

Chemical processes are disclosed that act to both regenerate and create new catalyst for iron salt catalyzed Kharasch coupling reactions during the process of creating halogenated hydrocarbons. Such processes include loading a reactor with a quantity of Fe(0) metal such as iron wire, supplying CCl.sub.4 to the reactor, supplying a phosphate compound to the reactor, supplying an alkene to the reactor, and supplying a carbonyl of Fe(0) to the reactor.

Chemical processes are disclosed that act to both regenerate and create new catalyst for iron salt catalyzed Kharasch coupling reactions during the process of creating halogenated hydrocarbons. Such processes include loading a reactor with a quantity of Fe(0) metal such as iron wire, supplying CCl.sub.4 to the reactor, supplying a phosphate compound to the reactor, supplying an alkene to the reactor, and supplying a carbonyl of Fe(0) to the reactor.

Disclosed is a process for the preparation of cis-1,1,1,4,4,4-hexafluoro-2-butene comprising contacting 1,1,1-trifluorotrichloroethane with hydrogen in the presence of a catalyst comprising ruthenium to produce a product mixture comprising 1316mxx, recovering said 1316mxx as a mixture of Z- and E-isomers, contacting said 1316mxx with hydrogen, in the presence of a catalyst selected from the group consisting of copper on carbon, nickel on carbon, copper and nickel on carbon and copper and palladium on carbon, to produce a second product mixture, comprising E- or ZCFC-1326mxz, and subjecting said second product mixture to a separation step to provide E- or Z-1326mxz. The E- or Z-1326mxz can be dehydrochlorinated in an aqueous basic solution with an alkali metal hydroxide in the presence of a phase transfer catalyst to produce hexafluoro-2-butyne, which can then be selectively hydrogenated to produce Z-1,1,1,4,4,4-hexafluoro-2-butene using either Lindlar's catalyst, or a palladium catalyst further comprising a lanthanide element or silver.