公开(公告)号：US20160347694A1

公开(公告)日：2016-12-01

申请号：US15114944

申请日：2015-02-06

Applicant: THE CHEMOURS COMPANY FC, LLC

Inventor： IVAN SERGEYEVICH BALDYCHEV ,  STEPHAN M. BRANDSTADTER ,  PATRICIA CHEUNG ,  MARIO JOSEPH NAPPA ,  SHENG PENG ,  DONALD J. TOTON

IPC: C07C17/25 ,  C07C17/354 ,  C07C17/281

CPC classification number: C07C17/25 ,  C07C17/23 ,  C07C17/281 ,  C07C17/354 ,  Y02P20/125 ,  Y02P20/582 ,  C07C21/18

Abstract: 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.

Abstract translation: 公开了一种制备顺式-1,1,1,4,4,4-六氟-2-丁烯的方法，其包括在包含钌的催化剂存在下使1,1,1-三氟三氯乙烷与氢气接触以产生产物 混合物，其包含1316mxx，以Z和E异构体的混合物回收所述1316mxx，使所述1316mxx与氢气在选自碳上的镍，碳上的镍，碳上的铜和镍的碳的存在下接触，以及 铜和钯碳，以产生包含E-或Z-CFC-1326mxz的第二产物混合物，并使所述第二产物混合物进行分离步骤以提供E-或Z-1326mxz。 在相转移催化剂存在下，E-或Z-1326mxz可以在碱金属氢氧化物水溶液中脱氯化氢以产生六氟-2-丁炔，然后可以选择性氢化生成Z-1,1， 1,4,4,4-六氟-2-丁烯，或者使用林德拉尔催化剂或进一步包含兰丹尼特元素或银的钯催化剂。

公开(公告)号：US20170369403A1

公开(公告)日：2017-12-28

申请号：US15699067

申请日：2017-09-08

Applicant: THE CHEMOURS COMPANY FC, LLC

Inventor： IVAN SERGEYEVICH BALDYCHEV ,  STEPHAN M. BRANDSTADTER ,  PATRICIA CHEUNG ,  MARIO JOSEPH NAPPA ,  SHENG PENG ,  DONALD J. TOTON

IPC: C07C17/25 ,  C07C17/281 ,  C07C17/23 ,  C07C17/354

CPC classification number: C07C17/25 ,  C07C17/23 ,  C07C17/281 ,  C07C17/354 ,  Y02P20/125 ,  Y02P20/582 ,  C07C21/18

Abstract: 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.