From Acetylenically Unsaturated Compound Patents (Class 570/154)
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Patent number: 11904301Abstract: A method of chlorinating a antimony fluorohalide catalyst is disclosed. In one embodiment the method comprises contacting an antimony fluorohalide catalyst that contains one or more fluorines with a regenerating agent chosen from 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,3-tetrachloropropane (250fb), 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and combinations of 1233xf, 250fb, and 244bb, under conditions effective to exchange at least one fluorine in the antimony fluorohalide catalyst with chlorine. The method can be used to regenerate spent antimony fluorohalide catalyst, for example regenerating SbCl5 from SbF5.Type: GrantFiled: September 6, 2019Date of Patent: February 20, 2024Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Xuehui Sun, Mario Joseph Nappa, Karl Krause
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Patent number: 10227276Abstract: 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.Type: GrantFiled: August 23, 2018Date of Patent: March 12, 2019Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Ivan Sergeyevich Baldychev, Stephan M. Brandstadter, Patricia Cheung, Mario Joseph Nappa
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Patent number: 9216932Abstract: The present invention is related to making hydrofluorocarbons (HCFCs), more specifically, 3,3,3-trifluoropropyne (TFP), from trans-1-chloro-3,3,3-trifluoropropene (trans-1233zd) by contacting the trans-1233zd with a base. Preferably, the base is potassium hydroxide or potassium tert-butoxide, which may or may not be dissolved in as solvent.Type: GrantFiled: May 5, 2014Date of Patent: December 22, 2015Assignee: Honeywell International Inc.Inventors: Yian Zhai, Andrew J. Poss, Rajiv R. Singh
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Patent number: 8901360Abstract: Disclosed is a process for preparing cis-1,1,1,4,4,4-hexafluorobutene comprising the steps of (a) reacting CCl4 with a compound having the formula CF3CX?CXH, where each X is independently halogen or hydrogen, to form a compound having the formula CF3CXClCXHCCl3; (b) fluorinating the compound formed in step (a) to form a compound having the formula CF3CXHCXHCF3; (c) converting the compound formed in step (b) by a reaction selected from the group consisting of dehydrohalogenation, dehalogenation and both reactions, to form a compound having the formula CF3C?CCF3; and (d) catalytically reducing the compound formed in step (c) with hydrogen to form the compound having the formula:Type: GrantFiled: May 19, 2011Date of Patent: December 2, 2014Assignee: Honeywell International Inc.Inventors: Andrew Joseph Poss, David Nalewajek, Haridasan K. Nair, Michael Van Der Puy
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Patent number: 8877988Abstract: In accordance with the present invention, processes for producing bromofluoropropenes in commercial quantities by reacting 3,3,3-trifluoropropyne with hydrogen bromide at elevated temperatures are provided.Type: GrantFiled: December 6, 2013Date of Patent: November 4, 2014Assignee: Honeywell International Inc.Inventors: Yian Zhai, Andrew J. Poss, Rajiv R. Singh
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Publication number: 20140179960Abstract: In accordance with the present invention, processes for producing bromofluoropropenes in commercial quantities by reacting 3,3,3-trifluoropropyne with hydrogen bromide at elevated temperatures are provided.Type: ApplicationFiled: December 6, 2013Publication date: June 26, 2014Applicant: Honeywell International Inc.Inventors: Yian Zhai, Andrew J. Poss, Rajiv R. Singh
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Patent number: 8653310Abstract: Disclosed is a process for making cis-1-chloro-3,3,3-trifluoropropene comprising reacting 3,3,3-trifluoropropyne with HCl in a reaction vessel at a yield of at least about 80%.Type: GrantFiled: November 12, 2012Date of Patent: February 18, 2014Assignee: Honeywell International Inc.Inventors: Yian Zhai, Andrew Joseph Poss, Rajiv Ratna Singh
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Publication number: 20130310614Abstract: The present invention provides processes for the production of HCFO-1233zd, 1-chloro-3,3,3-trifluoropropene, from the starting material, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf). In a first process, HCFO-1233zd is produced by the isomerization of HCFO-1233xf. In a second process, HCFO-1233zd is produced in a two-step procedure which includes (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne; and (ii) hydrochlorination of the trifluoropropyne into HCFO-1233zd.Type: ApplicationFiled: March 14, 2013Publication date: November 21, 2013Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20130158304Abstract: An object is to provide a method for producing 1,1,1,4,4,4-hexafluoro-2-butene with high efficiency, which is suitable for a flow reaction, and cis-1,1,1,4,4,4-hexafluoro-2-butene can be efficiently obtained when isomerization of hexafluoro-1,3-butadiene is conducted using a catalyst and the resultant mixture is successively subjected to catalytic hydrogenation to produce cis-1,1,1,4,4,4-hexafluoro-2-butene, wherein the whole process is performed by a flow catalytic reaction.Type: ApplicationFiled: June 13, 2011Publication date: June 20, 2013Inventors: Heng-dao Quan, Masanori Tamura, Junji Mizukado, Akira Sekiya
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Publication number: 20130150633Abstract: Disclosed is a process for making cis-1-chloro-3,3,3-trifluoropropene comprising reacting 3,3,3-trifluoropropyne with HCl in a reaction vessel at a yield of at least about 80%.Type: ApplicationFiled: November 12, 2012Publication date: June 13, 2013Applicant: Honeywell International Inc.Inventor: Honeywell International Inc.
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Patent number: 8198491Abstract: The present invention provides a process for preparing 2,3,3,3-tetrafluoropropene represented by CF3CF?CH2 and 1,3,3,3-tetrafluoropropene represented by CF3CH?CHF, in which 3,3,3-trifluoropropyne represented by the chemical formula CF3C?CH is reacted with hydrogen fluoride under heating. The process of the present invention is a simple, effective and industrially applicable process for preparing 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene.Type: GrantFiled: July 21, 2009Date of Patent: June 12, 2012Assignee: Daikin Industries, Ltd.Inventors: Nose Masatoshi, Komatsu Yuzo, Sugiyama Akinari, Shibanuma Takashi
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Publication number: 20110288346Abstract: Disclosed is a process for preparing cis-1,1,1,4,4,4-hexafluoropropene comprising the steps of (a) reacting CCl4 with a compound having the formula CF3CX?CXH, where each X is independently halogen or hydrogen, to form a compound having the formula CF3CXClCXHCCl3; (b) fluorinating the compound formed in step (a) to form a compound having the formula CF3CXHCXHCF3; (c) converting the compound formed in step (b) by a reaction selected from the group consisting of dehydrohalogenation, dehalogenation and both reactions, to form a compound having the formula CF3C?CCF3; and (d) catalytically reducing the compound formed in step (c) with hydrogen to form the compound having the formula:Type: ApplicationFiled: May 19, 2011Publication date: November 24, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Andrew Joseph Poss, David Nalewajek, Haridasan K. Nair, Michael Van Der Puy
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Publication number: 20110201851Abstract: The present invention provides a process for preparing 2,3,3,3-tetrafluoropropene comprising the steps of: (a) reacting 3,3,3-trifluoropropyne with hydrogen fluoride while heating to obtain a product containing 2,3,3,3-tetrafluoropropene; (b) separating the product obtained in Step (a) into Component A containing 2,3,3,3-tetrafluoropropene and 3,3,3-trifluoropropyne, and Component B containing 1,3,3,3-tetrafluoropropene; (c) separating 2,3,3,3-tetrafluoropropene and 3,3,3-trifluoropropyne contained in Component A obtained in Step (b) into each compound; (d) conducting a dehydrofluorination reaction by heating Component B obtained in Step (b) in the presence of a catalyst; (e) separating the product obtained in Step (d) into Component C containing 2,3,3,3-tetrafluoropropene and 3,3,3-trifluoropropyne, and Component D containing 1,3,3,3-tetrafluoropropene; (f) separating 2,3,3,3-tetrafluoropropene and 3,3,3-trifluoropropyne contained in Component C obtained in Step (e) into each compound; and (g) conducting a dType: ApplicationFiled: October 13, 2009Publication date: August 18, 2011Inventors: Masatoshi Nose, Kazuhiro Takahashi, Yuzo Komatsu, Akinari Sugiyama, Takashi Shibanuma
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Publication number: 20110137090Abstract: The present invention provides a process for preparing 2,3,3,3-tetrafluoropropene represented by CF3CF?CH2 and 1,3,3,3-tetrafluoropropene represented by CF3CH?CHF, in which 3,3,3-trifluoropropyne represented by the chemical formula CF3C?CH is reacted with hydrogen fluoride under heating. The process of the present invention is a simple, effective and industrially applicable process for preparing 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene.Type: ApplicationFiled: July 21, 2009Publication date: June 9, 2011Inventors: Masatoshi Nose, Yuzo Komatsu, Akinari Sugiyama, Takashi Shibanuma
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Patent number: 7951981Abstract: A process for producing a perfluoroalkyne compound includes an addition reaction step of adding Cl2, Br2, or I2 to a compound shown by the formula (1) CH3C?CR1 to obtain a compound shown by the formula (2) CH3CX2CX2R1, a fluorination reaction step of reacting the compound shown by the formula (2) with fluorine gas to obtain a compound shown by the formula (3) CF3CX2CX2R2, and a dehalogenation reaction step of contacting the compound shown by the formula (3) with a metal or an organometallic compound to obtain a perfluoroalkyne compound shown by the formula (4) CF3C?CR2. According to the present invention, a perfluoroalkyne compound can be produced at high productivity and high yield using starting raw materials which are environmentally friendly and industrially available. In the above formulas, R1 represents a methyl group or an ethyl group, X represents Cl, Br, or I, and R2 represents a trifluoromethyl group or a pentafluoroethyl group.Type: GrantFiled: March 30, 2007Date of Patent: May 31, 2011Assignee: Zeon CorporationInventor: Tatsuya Sugimoto
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Publication number: 20100292516Abstract: A process for producing a perfluoroalkyne compound includes an addition reaction step of adding Cl2, Br2, or I2 to a compound shown by the formula (1) CH3C?CR1 to obtain a compound shown by the formula (2) CH3CX2CX2R1, a fluorination reaction step of reacting the compound shown by the formula (2) with fluorine gas to obtain a compound shown by the formula (3) CF3CX2CX2R2, and a dehalogenation reaction step of contacting the compound shown by the formula (3) with a metal or an organometallic compound to obtain a perfluoroalkyne compound shown by the formula (4) CF3C?CR2. According to the present invention, a perfluoroalkyne compound can be produced at high productivity and high yield using starting raw materials which are environmentally friendly and industrially available. In the above formulas, R1 represents a methyl group or an ethyl group, X represents Cl, Br, or I, and R2 represents a trifluoromethyl group or a pentafluoroethyl group.Type: ApplicationFiled: March 30, 2007Publication date: November 18, 2010Applicant: Zeon CorporationInventor: Tatsuya Sugimoto
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Patent number: 7435700Abstract: A chromium-containing catalyst is disclosed which includes both ZnCr2O4 and crystalline ?-chromium oxide. The ZnCr2O4 contains between about 10 atom percent and 67 atom percent of the chromium in the composition and at least about 70 atom percent of the zinc in the composition, and at least about 90 atom percent of the chromium present as chromium oxide in the composition is present as ZnCr2O4 or crystalline ?-chromium oxide. Also disclosed are a method for preparing this composition comprising ZnCr2O4 and crystalline ?-chromium oxide; and a chromium-containing catalyst composition prepared by treatment of the composition comprising ZnCr2O4 and crystalline ?-chromium oxide with a fluorinating agent.Type: GrantFiled: October 13, 2004Date of Patent: October 14, 2008Assignee: E.I. du Pont de Nemars and CompanyInventors: Tammy Georgette Amos, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert, Shekhar Subramoney
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Patent number: 6784327Abstract: A process for the production of a fluorinated organic compound, characterized by fluorinating an organic compound having a hydrogen atoms using IF5; and a novel fluorination process for fluorinating an organic compound having a hydrogen atoms by using a fluorinating agent containing IF5 and at least one member selected from the group consisting of acids, bases, salts and additives.Type: GrantFiled: December 10, 2002Date of Patent: August 31, 2004Assignee: Daikin Industries, Ltd.Inventors: Norihiko Yoneda, Tsuyoshi Fukuhara, Kazuhiro Shimokawa, Kenji Adachi, Satoshi Oishi
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Patent number: 6251843Abstract: A detergent composition which is suitable for making into bars for personal washing comprises: (a) 10 to 60% wt. of a synthetic, non-soap detergent; (b) 20 to 60% wt. of water soluble material which is neither soap nor a non-soap detergent and which has a melting point in the range 40° C. to 100° C.; and (c) 5 to 50% wt. of water insoluble material which is neither soap nor a non-soap detergent and which has a melting point in the range 40° C. to 100° C. The content of water, if any does not exceed 20% wt. of the composition and better is less than 15% wt. The materials (b) and (c) serve to give structure to the bars. The compositions can be prepared by melting together the above mentioned components at a temperature of 50-100° C., without the conventional energetic working. Desirably the molten mixture contains less than 20% wt. material, other than synthetic, non-soap detergent, which does not enter the liquid phase.Type: GrantFiled: September 28, 1999Date of Patent: June 26, 2001Assignee: Unilever Home & Personal Care USA, division of Conopco, Inc.Inventors: John George Chambers, Bryan Stuart Joy, Melissa Iva Katz, John Gerrard Sheehan
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Patent number: 5334788Abstract: Substrate compounds are reacted by passing them through an eductor with fluorine gas optionally in the presence of a liquid medium and preferably in a loop reactor with cooling means thereby providing rapid but controlled reaction suitable for industrial scale production. Vinylidene chloride, for example, smoothly produces dichlorodifluoroethane and dichlorotrifluoroethane in good yield.Type: GrantFiled: May 1, 1992Date of Patent: August 2, 1994Assignee: PCR Group, Inc.Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
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Patent number: 5177275Abstract: Substrate compounds are reacted by passing them through an eductor with fluorine gas optionally in the presence of a liquid medium and preferably in a loop reactor with cooling means thereby providing rapid but controlled reaction suitable for industrial scale production. Vinylidene chloride, for example, smoothly produces dichlorodifluoroethane and dichlorotrifluoroethane in good yield.Type: GrantFiled: May 1, 1989Date of Patent: January 5, 1993Assignee: PCR Group, Inc.Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
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Patent number: 5017718Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.Type: GrantFiled: January 26, 1984Date of Patent: May 21, 1991Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Takamasa Fuchikami
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Patent number: 4967022Abstract: Processes for the preparation of perfluoroalkyl substituted allenes and novel bis-allenyl substituted perfluoroalkanes are disclosed.Type: GrantFiled: November 29, 1989Date of Patent: October 30, 1990Assignee: E. I. du Pont de Nemours and CompanyInventor: Ming-Hong Hung
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Patent number: 4816180Abstract: A novel tolan type liquid crystal compound having a large optical anisotropy value, a high N-I transistion temperature and also a low viscosity, and a liquid crystal composition containing the same are provided, which compound is a 4-(trans-4"-alkylcyclohexyl-1"-ethyl)-3',4'-substituted- or 4-(trans-4"-alkylcyclohexyl-1'-ethyl)-4'-substituted-tolan expressed by the formula ##STR1## wherein R' represents an alkyl group of 1 to 10 carbon atoms, X' represents a halogen atom of F, Cl or Br and X" represents hydrogen atom or a halogen atom of F, Cl or Br.Type: GrantFiled: December 11, 1987Date of Patent: March 28, 1989Assignee: Chisso CorporationInventors: Yasuyuki Goto, Tetsuya Ogawa
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Patent number: 4734534Abstract: Novel alumina-supported nickel boride catalysts prepared by the borohydride promoted reduction of nickel arsenate are described. Method of catalyst preparation and process for hydrogenation of acetylenic and diolefinic compounds employing the invention catalysts are also described.Type: GrantFiled: February 5, 1986Date of Patent: March 29, 1988Assignee: Phillips Petroleum CompanyInventor: Ted H. Cymbaluk
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Patent number: 4438088Abstract: The invention disclosed herein is a method for preparing antimony trifluorodichloride whereby antimony trifluoride is dispersed in a liquid organic medium to form a slurry and contacted with chlorine. The invention further comprises a process for fluorinating a fluorinatable hydrocarbon or halocarbon whereby a fluorinatable hydrocarbon or halocarbon is contacted with the antimony trifluorodichloride prepared in the above process, and the fluorinated product is distilled off.Type: GrantFiled: March 11, 1982Date of Patent: March 20, 1984Assignee: The Dow Chemical CompanyInventor: John D. Weaver