Unsaturated Patents (Class 570/135)
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Publication number: 20110224125Abstract: Disclosed are compositions and systems having utility in numerous situations, including in particular solvent cleaning systems, as well as refrigerant lubricants and/or compatibilizing agents, and to methods which utilize such compositions and systems. More particularly, the present invention in preferred aspects is directed to solvents, blowing agents, heat transfer fluids and compatibilizing agents comprising the compound 3-chloro-1,1,1,6,6,6-hexafluoro-2,4-hexadiene.Type: ApplicationFiled: March 12, 2010Publication date: September 15, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Robert Johnson, Hsueh Sung Tung
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Publication number: 20110041529Abstract: The present invention relates to solvent/cleaner and heat transfer fluid compositions comprising at least one hydrochlorofluoroolefin (HCFO), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), particularly the trans-isomer. The HCFO of the present invention can be used in combination with co-agents including, hydrofluorocarbons (HFCs), hydrofluoroolefins (HFOs), hydrocarbons, ethers including hydrofluoroethers (HFEs), esters, ketones, alcohols, 1,2-transdichloroethylene and mixtures thereof.Type: ApplicationFiled: May 12, 2009Publication date: February 24, 2011Applicant: ARKEMA INC.Inventors: Benjamin Bin Chen, Philippe Bonnet, Maher Y. Elsheikh, Brett L. Van Horn, Laurent Abbas
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Patent number: 7884255Abstract: Chemical Production Processes and Systems. Chemical production processes are provided that include replacing a halogen of an unsaturated halocarbon to produce an unsaturated hydrohalocarbon. Chemical production systems are provided that include a reaction zone coupled to first and second reservoirs, the first reservoir containing an unsaturated halocarbon and the second reservoir containing a hydrogenating reagent with the system being configured to expose the unsaturated halocarbon of the first reservoir to the hydrogenating agent of the second reservoir within the reaction zone.Type: GrantFiled: August 26, 2005Date of Patent: February 8, 2011Inventor: Vicki Hedrick
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Publication number: 20110001080Abstract: The present invention relates to formulated systems of 1-chloro-3,3,3-trifluoropropene (R-1233zd) and/or 2-chloro-3,3,3-trifluoropropene (R-1233xf) that are sufficiently thermally and chemically stable such that they can be effectively used sans additional stabilizers. The formulations of the present invention are particularly useful compositions for refrigeration, heat transfer, and foam pre-mixes.Type: ApplicationFiled: March 6, 2009Publication date: January 6, 2011Applicant: ARKEMA INC.Inventors: Brett L. Van Horn, Maher Y. Elsheikh, Benjamin Bin Chen, Philippe Bonnet
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Publication number: 20100320428Abstract: A dielectric gaseous compound which exhibits the following properties: a boiling point in the range between about ?20° C. to about ?273° C.; non-ozone depleting; a GWP less than about 22,200; chemical stability, as measured by a negative standard enthalpy of formation (dHf<0); a toxicity level such that when the dielectric gas leaks, the effective diluted concentration does not exceed its PEL; and a dielectric strength greater than air.Type: ApplicationFiled: August 30, 2010Publication date: December 23, 2010Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Matthew H. Luly, Robert G. Richard
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Patent number: 7795480Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.Type: GrantFiled: July 24, 2008Date of Patent: September 14, 2010Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh S. Tung
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Publication number: 20100139274Abstract: Aspects of the present invention are directed to working fluids and their use in processes wherein the working fluids comprise compounds having the structure of formula (I): wherein R1, R2, R3, and R4 are each independently selected from the group consisting of: H, F, Cl, Br, and C1-C6 alkyl, at least C6 aryl, at least C3 cycloalkyl, and C6-C15 alkylaryl optionally substituted with at least one F, Cl, or Br, wherein formula (I) contains at least one F and at least one Cl or Br, provided that if any R is Br, then the compound does not have hydrogen. The working fluids are useful in Rankine cycle systems for efficiently converting waste heat generated from industrial processes, such as electric power generation from fuel cells, into mechanical energy or further to electric power. The working fluids of the invention are also useful in equipment employing other thermal energy conversion processes and cycles.Type: ApplicationFiled: December 3, 2009Publication date: June 10, 2010Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Gary Zyhowski, Ryan Hulse, Haridasan K. Nair, David Nalewajek, Rajiv R. Singh
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Publication number: 20100113629Abstract: The present invention relates to blowing agent compositions comprising at least one hydrochlorofluoroolefin (HCFO) used in the preparation of foamable thermoplastic compositions. The HCFOs of the present invention include, but are not limited to, 1-chloro-3, 3,3-trifluoropropene (HCFO-1233zd), particularly the trans-isomer, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), dichloro-fluorinated propenes, and mixtures thereof. The blowing agent compositions of the present invention are used with coblowing agents including carbon dioxide, atmospheric gases, hydrofluorocarbons (HFC), hydrofluoroolefins (HFO), alkanes, hydrofluoroethers (HFE), and mixtures thereof. Preferred HFCs used as coblowing agents in the present invention include, but are not limited to, 1,1,1,2-tetrafluoroethane (HFC-134a), 1,1-difluoroethane (HFC-152a), 1,1,1-trifluoroethane (HFC-143a), pentafluorethane (HFC-125), difluoromethane (HFC-32).Type: ApplicationFiled: March 28, 2008Publication date: May 6, 2010Applicant: Arkema Inc.Inventors: Brett L. Van Horn, Maher Y. Elsheikh, Benjamin Bin Chen, Philippe Bonnet
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Publication number: 20090278076Abstract: Disclosed are the use of fluorine substituted olefins, including tetra- and penta-fluoropropenes, in a variety of applications, including connection with blowing agents, foams, foamable compositions, foaming methods, heat transfer compositions and methods, propellants, and solvating methods.Type: ApplicationFiled: March 26, 2009Publication date: November 12, 2009Applicant: HONEYWELL INTERNATIONAL, INC.Inventors: Rajiv R. Singh, Hang T. Pham, Ian Shankland, David P. Wilson, Gary Knopack, David J. Williams
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Publication number: 20090270522Abstract: Provided are foam blowing agents comprising one or more chlorofluoroolefins selected from 1,2-dichloro-1,2-difluoroethene, 3,3-dichloro-3-fluoropropene, 2-chloro-1,1,1,3,4,4,4-heptafluoro-2-butene, and 2-chloro-1,1,1,4,4,4-hexafluoro-2-butene, as well as foams produced therefrom.Type: ApplicationFiled: April 23, 2009Publication date: October 29, 2009Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Rajiv R. Singh, Ian Shankland, James M. Bowman, David J. Williams
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Publication number: 20090203945Abstract: A method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3(—CX2X2)nCX1?H2??(I) to at least one compound of formula (II): CF3(CX2X2)nCX1?H2??(II), where X1 is Cl, Br or I, each X2 is independently selected from the group consisting of H, Cl, F, Br or J, and n is 0, 1, or 2.Type: ApplicationFiled: August 21, 2008Publication date: August 13, 2009Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Sudip Mukhopadhyay, Cheryl L. Bortz, Kim M. Fleming, Steven D. Phillips, Rajesh K. Dubey
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Patent number: 7538171Abstract: A fluorine-containing copolymer, which comprises a hydroxyl-terminated fluorine-containing vinyl ether, represented by the following general formula: CF2?CFORfCH2OH (where Rf is a fluoroalkylene group, a fluoroalkyl ether group, or a fluoroalkoxyfluoroalkyl ether group, having 1-25 carbon atoms), and at least one of other fluorine-containing unsaturated monomers, where a high-molecular weight fluorine-containing copolymer having a melt viscosity (230° C.) of 0.1-100 g/10 min. is insoluble in a solvent, and can be used suitably for melt molding, whereas a low-molecular weight fluorine-containing copolymer having a glass transition temperature Tg of 20° C., or higher, and a number average molecular weight Mn of 1,000, or more is soluble in a solvent, and can be used suitably for coating agents, etc.Type: GrantFiled: November 18, 2005Date of Patent: May 26, 2009Assignee: Unimatec Co., Ltd.Inventors: Jun Kanega, Ji-Shan Jin, Katsumi Suzuki, Takashi Enokida, Keisuke Kokin
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Patent number: 7501540Abstract: The present invention provides a process for producing compounds useful as raw materials for various fluororesins in high yields in few steps from inexpensive and readily available starting materials. The following compound (1) and the following compound (2) are reacted to form the following compound (3), then the compound (3) is fluorinated in a liquid phase to form the following compound (4), and the ester bonds in the compound (4) are dissociated to form the compound (5), or the compound (5) and the compound (6). HOCH2-Q-O—(CH2)3—OH??(1), CRBCOX??(2), RBCOOCH2-Q-O—(CH2)3—OCORB??(3), RBFCOOCF2-QF-O—(CF2)3—OCORBF??(4), FCO-QF-O—(CF2)2—COF??(5), RBFCOF??(6).Type: GrantFiled: June 29, 2007Date of Patent: March 10, 2009Assignee: Asahi Glass Company, LimitedInventors: Shu-zhong Wang, Takashi Okazoe, Eisuke Murotani, Kunio Watanabe, Daisuke Shirakawa, Kazuya Oharu
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Publication number: 20090030244Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.Type: ApplicationFiled: July 24, 2008Publication date: January 29, 2009Applicant: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh S. Tung
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Publication number: 20080292564Abstract: Various compositons, including particularly aerosol compositions, containing fluorinated olefins, including particularly tetra- and penta-fluorpropenes, in a variety of applications are disclosed.Type: ApplicationFiled: September 4, 2007Publication date: November 27, 2008Applicant: Honeywell International, Inc.Inventors: Rajiv R. Singh, Hang T. Pham, David P. Wilson, Raymond H. Thomas, Mark W. Spatz, David A. Metcalf
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Publication number: 20080171652Abstract: Various compositions, including particularly solvent compositions, containing fluorinated olefins, including particularly tetra- and penta-fluorpropenes, in a variety of applications are disclosed.Type: ApplicationFiled: September 4, 2007Publication date: July 17, 2008Applicant: Honeywell International, Inc.Inventors: Rajiv R Singh, Raymond H. Thomas, Gary Knopeck
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Patent number: 7371904Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene which comprises, in one embodiment, reacting a compound of CF3X1 with a compound of CX2H?CHX3, wherein X1, X2, and X3 are each independently selected from the group consisting of fluorine, chlorine, bromine and iodine, to produce a reaction product comprising a compound of CF3CH?CHX3, wherein X3 is as described above; and when X3 is not fluorine, fluorinating the compound to produce 1,3,3,3-tetrafluoropropene. The process in another embodiment comprises preparing tetrafluoropropene comprising thermally cracking one or more compounds capable of producing a reaction mixture which preferably comprises diflurocarbene radicals and vinylidene fluoride, and converting said reaction mixture into—tetrafluoropropene (1,3,3,3-tetrafluoropropene).Type: GrantFiled: April 29, 2005Date of Patent: May 13, 2008Assignee: Honeywell International Inc.Inventors: Jing Ji Ma, Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
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Publication number: 20080003127Abstract: Disclosed are cover gas compositions comprising fluoroolefins for impeding the oxidation of molten nonferrous metals and alloys, such as magnesium.Type: ApplicationFiled: March 26, 2007Publication date: January 3, 2008Applicant: Honeywell International Inc.Inventors: Matthew H. Luly, Rajiv R. Singh
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Patent number: 7304191Abstract: The present invention relates to a fluorination method for the synthesis of halofluoroorganic compounds which can be used, inter alia, as precursors in the synthesis of 2,3-unsaturated fluoroorganic carbonyl compounds comprising a fluorine substituent in the 2 position.Type: GrantFiled: August 6, 2001Date of Patent: December 4, 2007Assignee: Solvay (Societe Anonyme)Inventors: Véronique Mathieu, Francine Janssens, James Franklin
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Patent number: 7241928Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2?CR3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. New compounds disclosed include CF3CF2CCl2CH2CCl3, CF3CCl2CH2CH2Cl and CF3CCl2CH2CHClF. These compounds are useful as intermediates for producing hydrofluorocarbons.Type: GrantFiled: October 1, 2004Date of Patent: July 10, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur N.Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 7081279Abstract: Liquid crystalline compounds having a large negative ?? low viscosity, a large K33/K11 value, a small ??/?? and mutually excellent solubility even at low temperature, compositions containing at least one of the compounds and liquid crystal display devices containing such a liquid crystal compositions are disclosed.Type: GrantFiled: August 29, 2003Date of Patent: July 25, 2006Assignee: Chisso CorporationInventors: Takashi Kato, Tomoyuki Kondo, Henry Bernhardt, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
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Publication number: 20040127756Abstract: The present invention is to provide a method for producing a highly branched perfluoroolefin conveniently in a high yield, a novel highly branched perfluoroolefin, a method for producing a super-stable perfluoroalkyl radical and a novel super-stable perfluoroalkyl radical.Type: ApplicationFiled: October 16, 2003Publication date: July 1, 2004Applicants: NATIONAL INSTITUTE OF ADVANCED IND. SCIENCE AND TECH., DAIKIN INDUSTRIES, LTD.Inventors: Taizo Ono, Masakazu Nishida, Masaharu Okazaki, Kazumi Toriyama, Tetsuo Shimizu
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Patent number: 6710214Abstract: The present invention is to provide a method for producing a highly branched perfluoroolefin conveniently in a high yield, a novel highly branched perfluoroolefin, a method for producing a super-stable perfluoroalkyl radical and a novel super-stable perfluoroalkyl radical. The present invention is a production method of a perfluoroolefin which comprises reacting a hexafluoropropene trimer with a trialkylperfluoroalkylsilane in an aprotic polar solvent using a fluoride ion as a catalyst.Type: GrantFiled: November 12, 2002Date of Patent: March 23, 2004Assignees: National Institute of Advanced Industrial Science and Technology, Daikin Industries, Ltd.Inventors: Taizo Ono, Masakazu Nishida, Masaharu Okazaki, Kazumi Toriyama, Tetsuo Shimizu
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Patent number: 6692657Abstract: Liquid crystalline compounds having a large negative &Dgr;∈ low viscosity, a large K33/K11 value, a small &Dgr;∈/&Dgr;⊥ and mutually excellent solubility even at low temperature, compositions containing at least one of the compounds and liquid crystal display devices containing such a liquid crystal compositions are disclosed.Type: GrantFiled: June 2, 1999Date of Patent: February 17, 2004Assignee: Chisso CorporationInventors: Takashi Kato, Tomoyuki Kondo, Henry Bernhardt, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6664431Abstract: The present invention relates to a process for producing fluorinated aliphatic compounds by pyrolysis of perfluorocarboxylic acids and their derivatives—halides and esters. The pyrolysis is carried out in the presence of a catalyst consisting of a carrier most preferably selected from the series comprising active carbon, magnesium oxide, calcium oxide, barium oxide, zinc oxide, aluminum oxide, nickel oxide, oxides of silicon promoted with alkali metal halides, selected from the series comprising fluorides, chlorides bromides, iodides of sodium, potassium, rubidium, cesium, at a temperature in the range of from about 100° C. to about 450° C.; with producing fluorinated aliphatic compounds selected from the series comprising perfluoroolefins, polyfluoroolefins and their derivatives; and also in the presence additionally of hydrogen fluoride with the formation of fluorinated aliphatic compounds selected from the series comprising polyfluoroalkanes and their derivatives.Type: GrantFiled: March 14, 2001Date of Patent: December 16, 2003Assignee: Zakrytoe Aktsionernoe Obschestvo Nauchno-Proizvodstvennoe Obiedinenie “Pim-Invest”Inventors: Sergei Mikhailovich Igumnov, Galina Ivanovna Lekontseva
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Publication number: 20030216594Abstract: According to the invention there is proposed a process for the preparation of 4,4,4-trifluoro-3-methylamino-crotonic acid esters by dehydrating trifluoroacetoacetic acid esters and methylamine in the presence of an inert reaction medium and of a C1-C4carboxylic acid, in which process the reaction is carried out at a temperature of from 75 to 100° C. without isolation of intermediates and the water that forms during the reaction is removed continuously from the reaction medium.Type: ApplicationFiled: March 23, 2001Publication date: November 20, 2003Inventors: Reinhard Georg Hanreich, Herng-Tay Wu, Michael Allen Oliver, Dean Kent Hoglen
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Publication number: 20030181615Abstract: Compounds corresponding to formula (I)Type: ApplicationFiled: March 6, 2003Publication date: September 25, 2003Inventors: Bruno Michel Ameduri, Michel armand, Mario Boucher, Abdellatif Manseri
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Patent number: 6255543Abstract: Selected novel partially fluorinated &agr;,&ohgr;-dienes can be free radically (co)polymerized to form polymers in which cyclic structures are present. The polymers are useful for films, coatings and molded parts.Type: GrantFiled: December 5, 2000Date of Patent: July 3, 2001Assignee: E. I. du Pont de Nemours and CompanyInventor: Zhen-Yu Yang
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Patent number: 6229058Abstract: The instant invention relates to producing fluorinated propanes and pentanes. More particularly it relates to producing perhalofluoropropanes and pentanes by reacting dihalodifluoromethanes with polyfluoroethylenes, notably tetrafluoroethylene (TFE) and chlorotrifluoroethylene (CTFE) while in the presence of an aluminum chlorofluoride catalyst.Type: GrantFiled: August 28, 1997Date of Patent: May 8, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Allen Capron Sievert, Mario Joseph Nappa
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Patent number: 6156943Abstract: Processes are disclosed for producing hydrohaloolefins having the formula CF.sub.2 .dbd.C(CH.sub.2 RF)CF.sub.3, the formula FRCF.dbd.C(CH.sub.2 RF)CF.sub.3 or the formula FRCF.dbd.C(CH.sub.2 RF)(CF.sub.2 RF) wherein each R is a difinctional group of the formula --C.sub.2 F.sub.2 XY-- where X and Y are attached to the same carbon, each X is H, Br, Cl or F and each Y is F or CF.sub.3. The processes involve reacting (CF.sub.3).sub.2 C.dbd.CH.sub.2 or certain olefinic adducts thereof with a second olefm of the formula CF.sub.2 .dbd.CXY in the liquid phase in the presence of a Lewis acid catalyst selected from the group consisting of antimony pentafluoride and aluminum chlorofluoride.Also disclosed is 1,1,2,2,-tetrafluoro-3,3-bistrifluoromethylcyclobutane and a process for its production which involves reacting (CF.sub.3).sub.2 C.dbd.CH.sub.2 with CF.sub.2 .dbd.CF.sub.Type: GrantFiled: October 30, 1998Date of Patent: December 5, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: Viacheslav Alexandrovich Petrov
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Patent number: 6072088Abstract: A compound having the formula:CF.sub.3 CH.sub.2-w (H.sub.1-x CH.sub.2-y R.sub.m R'.sub.n CH.sub.1-z).sub.p H.sub.2-q CF.sub.3wherein w=0, 1 or 2; x=0 or 1; y=0, 1 or 2; m=0, 1 or 2; n=0 or 1; z=0 or 1; p=1 or 2; and q=0, 1 or 2; with the provisos that 1.ltoreq.w+x.ltoreq.2, 1.ltoreq.q+z.ltoreq.2, and p.multidot.y=p(m+2n)+(p-1)(x+z)+q+w+x+z-2; and wherein R includes the halogens having an atomic number greater than 9, and radicals having a valence of 1, and wherein R' is a group having a valence of 2, and a process for preparing the compound.Type: GrantFiled: August 10, 1999Date of Patent: June 6, 2000Assignee: Alliedsignal Inc.Inventor: Michael Van Der Puy
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Patent number: 5914423Abstract: A process for the preparation of a compound of formula (I):HetSCH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 (I)wherein Het is an optionally substituted 5- or 6-membered heterocyclic ring, which comprises reacting a compound of formula (II):HetSH (II)with a compound of formula (III):CF.sub.2 .dbd.CHCH.sub.2 CH.sub.2 L (III)wherein L is chlorine or bromine or a group --OSO2R.sup.a wherein R.sup.a is a C1-4 alkyl group or a phenyl group optionally substituted by a C1-4 alkyl group.Type: GrantFiled: November 24, 1997Date of Patent: June 22, 1999Assignee: Zeneca, LimitedInventors: Michael Drysdale Turnbull, Nigel James Willetts, Steven Fitzjohn, Prafula Govind Kholia, Harjindersingh Bansal, Alfred Glyn Williams
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Patent number: 5877357Abstract: The invention relates to a process for preparing perhaloethers from perhaloolefins and to a few "per se" new classes of perhaloethers thereby obtained.The process consists in reacting a perhalomonoolefin with a fluoroxy compound R.sub.x --OF (wherein R.sub.x represents a perhalogenated alkyl radical) at a temperature not exceeding 20.degree. C. in a liquid reaction medium and in the presence of inert gases.Type: GrantFiled: April 7, 1997Date of Patent: March 2, 1999Assignee: Ausimont S.p.A.Inventors: Antonio Marraccini, Antonio Pasquale, Tiziana Fiorani, Walter Navarrini
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Patent number: 5777184Abstract: A process for producing a fluorinated olefin having the formula:CH.sub.3-a F.sub.a CH.dbd.CHClwhere a=1,2 or 3, said process comprising catalytically reacting a chlorinated organic compound with a fluorination agent under conditions sufficient to form said hydrofluorocarbon compound, said chlorinated organic compound having the formula:CH.sub.b Cl.sub.c F.sub.d CH.sub.e CHCl.sub.ewhere b=0, 1 or 2; c=0, 1, 2, or 3; d=0, 1, 2 or 3; and e=1 or 2 with the provisos that b+c+d=3, c+e>1 and b+e<4.Type: GrantFiled: June 25, 1997Date of Patent: July 7, 1998Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, Alagappan Thenappan
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Patent number: 5750808Abstract: A process is disclosed for the dehydrohalogenation of partially halogenated ethanes of the formula C.sub.2 H.sub.a Cl.sub.b F.sub.c where a is an integer from 1 to 4, b is an integer from 0 to 3 and c is an integer form 1 to 5 to produce olefins selected from the group consisting of C.sub.2 H.sub.a-1 Cl.sub.b-1 F.sub.c and C.sub.2 H.sub.a-1 Cl.sub.b F.sub.c-1. The process involves contacting C.sub.2 H.sub.a Cl.sub.b F.sub.c with a zeolite selected from the group consisting of NaX and CsY. Selective reaction of one isomer from a mixture of two isomers is disclosed as a means for purification of the relatively unreactive isomer. Also disclosed is a process for producing perfluorocyclobutane which involves contacting CHF.sub.2 CClF.sub.2 with such zeolites.Type: GrantFiled: July 9, 1996Date of Patent: May 12, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Wendell Richard Cassel, David Richard Corbin, V.N. Mallikarjuna Rao
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Patent number: 5714654Abstract: A method is proposed for producing 1,1,1,3,3-pentafluoropropane, in which 1,1,3,3,3-pentafluoropropene is reduced at a temperature between 40.degree. C. and 300.degree. C. by reacting it with hydrogen in a gas phase in the presence of a palladium catalyst. Further, a method is proposed for producing 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene, in which the raw material 2-chloro-1,1,3,3,3-pentafluoropropene is hydrogenated especially at a temperature between 30.degree. C. and 450.degree. C. in the presence of a catalyst composed of at least one metal selected from palladium, platinum and rhodium. Further, a method is proposed of producing 1,1,3,3,3-pentafluoropropene, in which 1,1,1,3,3-pentafluoro-2,3-dichloropropane is dechlorinated by using hydrogen in the presence of a metal oxide catalyst. Based on these production methods, 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene can thus be produced with high yield rates.Type: GrantFiled: December 8, 1995Date of Patent: February 3, 1998Assignee: Daikin Industries Ltd.Inventors: Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Tatsuo Nakada
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Patent number: 5714649Abstract: Disclosed are compounds suitable for use as raw materials which enable cis-olefin compounds useful as physiologically active substances such as the sex pheromones of various insects, or as intermediates for the synthesis thereof to be prepared on an industrial scale at a reasonable cost, and processes for the preparation of cis-olefin compounds by using the same. For this purpose, novel compounds (i.e., 1-halo-cis-3-tetradecenes) of the general formula (I)CH.sub.3 (CH.sub.2).sub.9 CH.dbd.CH(CH.sub.2).sub.2 X (I)wherein X is a halogen atom, are used as raw materials for the preparation of cis-olefin compounds.Type: GrantFiled: December 20, 1995Date of Patent: February 3, 1998Assignee: Shin-Etsu Chemical CO., Ltd.Inventors: Takehiko Fukumoto, Daisuke Iwai, Shigeo Okano, Hiroshi Suzuki, Mitsuyoshi Oshima
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Patent number: 5681902Abstract: Free radical reaction of unsaturated material, dissolved in a polar, water immiscible organic solvent, & perfluoroalkyl iodide in the presence of buffer or means for adjusting pH of aqueous phase.Type: GrantFiled: January 11, 1996Date of Patent: October 28, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Donald Douglas May
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Patent number: 5654473Abstract: Novel trifluoromethylated intermediates are provided which are useful in synthesizing trifluoromethylated organic compounds. Specifically, compounds of the formula CF.sub.3 CCl.dbd.CHCH.sub.2 X are provided, which compounds are versatile intermediates for the synthesis of a wide variety of trifluoromethylated organic compounds.Type: GrantFiled: March 16, 1995Date of Patent: August 5, 1997Assignee: AlliedSignal Inc.Inventor: Michael Van Der Puy
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Patent number: 5648560Abstract: A process for preparing perhaloethers from perhaloolefins by reacting at least one fluorooxy compound R.sub.x --OF, wherein R.sub.x is a perhaloalkyl radical, with a perfluoroolefin in a liquid phase, optionally containing an organic solvent inert to the perfluoroolefin, while maintaining the temperature of the liquid phase in the range of -30.degree. to -120.degree. C. The process includes continuously feeding to the liquid phase a stream of an inert gas and a gaseous stream of the fluorooxy compound.Type: GrantFiled: December 9, 1994Date of Patent: July 15, 1997Assignee: Ausimont S.p.A.Inventors: Antonio Marraccini, Antonio Pasquale, Tiziana Fiorani, Walter Navarrini
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Patent number: 5585517Abstract: A novel process is described for reacting a perfluoroalkyl iodide with an olefinic compound, which comprises carrying out a free-radical addition reaction of the perfluoroalkyl iodide to the olefin in the presence of azoic or peroxy initiator and a water-soluble salt selected from the group consisting of sulfites, bisulfites, metabisulfites and dithionites. The adducts are obtained in high yield and purity and are useful for the preparation of oil- and water repellent products for use on paper, textiles, metal, wood and the like, or as precursors for fluorinated surfactants.Type: GrantFiled: April 12, 1995Date of Patent: December 17, 1996Assignee: Ciba-Geigy CorporationInventors: Ted Deisenroth, Robert Falk, Juerg Haase
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Patent number: 5557018Abstract: Selected partially fluorinated .alpha.,.omega.-dienes can be (co)polymerized to form polymers in which cyclic structures are present. A novel free radical polymerization process, in which the polymer obtained is dependent on the initiator used, is described. The polymers are useful for films, coatings and molded parts.Type: GrantFiled: September 13, 1995Date of Patent: September 17, 1996Assignee: E. I. du Pont de Nemours and CompanyInventors: Bruce E. Smart, Zhen-Yu Yang
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Processes for the preparation of fluorinated olefins and hydrofluorocarbons using fluorinated olefin
Patent number: 5532419Abstract: The invention relates to a cost effective and convenient process for the manufacture of fluorinated olefins of the formula RCF.sub.2 CH.dbd.CH.sub.2 where R is C.sub.x Cl.sub.y F.sub.z and y+z=2x+1. The invention is also directed to a practical process for converting these olefins to hydrofluorocarbons via the catalyzed fluorination with hydrogen fluoride. Hydrofluorocarbons produced via this process have application as solvents among other uses.Type: GrantFiled: September 15, 1995Date of Patent: July 2, 1996Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung -
Processes for the preparation of fluorinated olefins and hydrofluorocarbons using fluorinated olefin
Patent number: 5481050Abstract: The invention relates to a cost effective and convenient process for the manufacture of fluorinated olefins of the formula RCF.sub.2 CH=CH.sub.2 where R is C.sub.x Cl.sub.y F.sub.z and y+z=2.times.+1. The invention is also directed to a lo practical process for converting these olefins to hydrofluorocarbons via the catalyzed fluorination with hydrogen fluoride. Hydrofluorocarbons produced via this process have application as solvents among other uses.Type: GrantFiled: March 28, 1995Date of Patent: January 2, 1996Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung -
Patent number: 5463149Abstract: Disclosed are compounds suitable for use as raw materials which enable cis-olefin compounds useful as physiologically active substances such as the sex pheromones of various insects, or as intermediates for the synthesis thereof to be prepared on an industrial scale at a reasonable cost, and processes for the preparation of cis-olefin compounds by using the same. For this purpose, novel compounds (i.e., 1-halo-cis-3-tetradecenes) of the general formula (I)CH.sub.3 (CH.sub.2).sub.9 CH.dbd.CH(CH.sub.2).sub.2 X (I)wherein X is a halogen atom, are used as raw materials for the preparation of cis-olefin compounds.Type: GrantFiled: July 12, 1994Date of Patent: October 31, 1995Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takehiko Fukumoto, Daisuke Iwai, Shigeo Okano, Hiroshi Suzuki, Mitsuyoshi Oshima
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Processes for the preparation of fluorinated olefins and hydrofluorocarbons using fluorinated olefin
Patent number: 5446217Abstract: The invention relates to a cost effective and convenient process for the manufacture of fluorinated olefins of the formula RCF.sub.2 CH=CH.sub.2 where R is C.sub.x Cl.sub.y F.sub.z and y+z=2x+1. The invention is also directed to a practical process for converting these olefins to hydrofluorocarbons via the catalyzed fluorination with hydrogen fluoride. Hydrofluorocarbons produced via this process have application as solvents among other uses.Type: GrantFiled: May 16, 1994Date of Patent: August 29, 1995Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung -
Patent number: 5347058Abstract: Fluorinated olefins are produced by thermolysis of a silyl ester of a fluorinated aliphatic carboxylic acid in the presence of a catalyst which provides fluoride ion, such as potassium fluoride. The fluorinated olefins are useful as monomers and chemical intermediates.Type: GrantFiled: December 7, 1993Date of Patent: September 13, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. Farnham
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Patent number: 5342985Abstract: The invention relates to a process for the metathesis of olefins which comprises reacting an olefin of the formula YCZ.dbd.CZ--(CX.sub.2).sub.n R.sup.2 (II) whereinn is an integer from 1 to 28,X represents H or F,Y represents H or alkyl having from 1 to 10 carbon atoms andZ represents H or a non-aromatic hydrocarbon group having from 1 to 6 carbon atoms and R.sup.2 represents H, alkyl, halogen, COOR.sup.3 or OR.sup.4, wherein R.sup.3 and R.sup.4 represent alkyl having from 1 to 15 carbon atoms or phenyl which is unsubstituted or contains from 1 to 3 substituents or wherein R.sup.4 is trialkylsilyl R.sup.5 Si, wherein R.sup.5 represents alkyl having from 1 to 5 carbon atoms, at a catalyst comprising an oxidic carrier charged with a rhenium compound as defined hereinbefore.Type: GrantFiled: August 20, 1990Date of Patent: August 30, 1994Assignee: Hoechst AGInventors: Wolfgang A. Herrmann, Werner Wagner, Ursula Volkhardt
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Patent number: 5276221Abstract: This invention concerns a process for the production of polyfluoroolefins by the catalytic addition of polyfluoroallylic fluorides to fluoroethylenes. 1:1 and 1:2 Adducts such as F-pentene-2 and F-heptene-3 can be formed selectively and reduced further to dihydro- or trihydropolyfluoroalkanes, which are useful as HFC cleaning agents.Type: GrantFiled: January 25, 1993Date of Patent: January 4, 1994Assignee: E. I. du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 5258561Abstract: A chlorofluorination process is disclosed which employs a catalyst comprising chromium oxide for producing halohydrocarbons of the formula CHXFCF.sub.3 (where X is selected from Cl and F). The process is characterized by feeding a combination of components comprising, (i) at least one halohydrocarbon starting compound of the formula CY.sub.3 CH.sub.2 R.sup.1 (where R.sup.1 is selected from the group of H and F and each Y is independently selected from the group of Cl and F), (ii) hydrogen fluoride and (iii) chlorine to a reaction zone; contacting said combination of compounds in said reaction zone with a catalyst comprising chromium oxide at an elevated temperature to produce reaction zone products containing halohydrocarbon reaction products of the formula CHXFCF.sub.3 together with halohydrocarbons of the formula CZ.sub.3 CHR.sup.2 R.sup.3 (wherein R.sup.2 is selected from the group of H and Cl, R.sup.Type: GrantFiled: November 6, 1992Date of Patent: November 2, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Mario J. Nappa, V. N. Mallikarjuna Rao