The Chemours Company Fc, LLC

E.i. Dupont De Nemours and Company

Patricia Cheung

Mario Joseph Nappa

Concetta Lamarca

Stephan M Brandstadter

Ivan Sergeyevich Baldychev

Allen Capron Sievert

Sheng Peng

Karl Robert Krause

Stuart M Thomas

Donald J Toton

Michael A Sisk

Gregory Paul Shankwitz

Ming Woei Lau

Ivan Sergeyvich Baldychev

Ryan Eric Warner

Bradley Curt Fox

Joseph Michael Selby

A hydrogenation process is disclosed. The process involves reacting a fluoroolefin with Hin a reaction zone in the presence of a palladium catalyst to produce a hydrofluoroalkane product, wherein the palladium catalyst comprises palladium supported on a carrier wherein the palladium concentration is from about 0.001 wt % to about 0.2 wt % based on the total weight of the palladium and the carrier. Also disclosed is a palladium catalyst composition consisting essentially of palladium supported on &#x3b1;-AlOwherein the palladium concentration is from about 0.001 wt % to about 0.2 wt % based on the total weight of the palladium and the &#x3b1;-AlO. Also disclosed is a hydrogenation process comprising (a) passing a mixture comprising fluoroolefin and Hthrough a bed of palladium catalyst in a reaction zone wherein the palladium catalyst comprises palladium supported on a carrier; and (b) producing a hydrofluoroalkane product; characterized by: the palladium catalyst in the front of the bed having lower palladium concentration than the palladium catalyst in the back of the bed.

Catalytic hydrogenation of fluoroolefins, alpha-alumina supported palladium compositions and their use as hydrogenation catalysts

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 Z&#x2014;CFC-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.

Integrated process for the production of Z-1,1,1,4,4,4-hexafluoro-2-butene

A hydrogenation process is disclosed. The process involves reacting a fluoroolefin with Hin a reaction zone in the presence of a palladium catalyst to produce a hydrofluoroalkane product, wherein the palladium catalyst comprises palladium supported on a carrier wherein the palladium concentration is from about 0.001 wt % to about 0.2 wt % based on the total weight of the palladium and the carrier. Also disclosed is a palladium catalyst composition consisting essentially of palladium supported on &#x3b1;-AlOwherein the palladium concentration is from about 0.001 wt % to about 0.2 wt % based on the total weight of the palladium and the &#x3b1;-AlO. Also disclosed is a hydrogenation process comprising reacting a fluoroolefin with Hin a reaction zone in the presence of a palladium catalyst to produce a hydrofluoroalkane product, characterized by: the palladium catalyst consisting essentially of palladium supported on &#x3b1;-AlOwherein the palladium concentration is from about 0.001 wt % to about 0.2 wt % based on the total weight of the palladium and the &#x3b1;-AlO. Also disclosed is a hydrogenation process comprising (a) passing a mixture comprising fluoroolefin and Hthrough a bed of palladium catalyst in a reaction zone wherein the palladium catalyst comprises palladium supported on a carrier; and (b) producing a hydrofluoroalkane product; characterized by: the palladium catalyst in the front of the bed having lower palladium concentration than the palladium catalyst in the back of the bed.

Catalytic hydrogenation of fluoroolefins, alhpa-alumina supported palladium compositions and their use as hydrogenation catalysts

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 Z-CFC-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 lantanide element or silver.

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 Z-CFC-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 using either Lindlar's catalyst, or a palladium catalyst further comprising a lantanide element or silver.

A process is disclosed for reducing the amount of monofluoroacetate. The process involves (a) contacting a hydrofluorocarbon with a reactant basic aqueous solution to produce an organic phase solution containing a hydrofluoroolefin and an aqueous phase solution containing a monofluoroacetate; and (b) heating the aqueous phase solution to an effective temperature to reduce the amount of monofluoroacetate in the aqueous phase solution, wherein fluoride concentration in the aqueous phase solution is substantially high. Another process is disclosed for reducing the amount of monofluoroacetate. The process involves (a) contacting a first batch of hydrofluorocarbon with a first batch of reactant basic aqueous solution to produce a first batch of organic phase solution containing a hydrofluoroolefin and a first batch of aqueous phase solution containing a monofluoroacetate; (b) separating the first batch of organic phase solution from the first batch of aqueous phase solution; (c) mixing a second batch of hydrofluorocarbon and a second batch of reactant basic aqueous solution with the separated first batch of organic phase solution to produce a second batch of organic phase solution containing a hydrofluoroolefin and a second batch of aqueous phase solution containing a monofluoroacetate; (d) combining the first batch of aqueous phase solution with the second batch of aqueous phase solution; and (e) heating the combined aqueous phase solutions to an effective temperature to reduce the amount of monofluoroacetate in the combined aqueous phase solutions, wherein fluoride concentration in the combined aqueous phase solutions is substantially high.

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Glen Mills, PA, United States of America

Patricia Cheung