Unsaturated Patents (Class 570/135)
  • Publication number: 20110224125
    Abstract: 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: Application
    Filed: March 12, 2010
    Publication date: September 15, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert Johnson, Hsueh Sung Tung
  • Publication number: 20110041529
    Abstract: 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: Application
    Filed: May 12, 2009
    Publication date: February 24, 2011
    Applicant: ARKEMA INC.
    Inventors: Benjamin Bin Chen, Philippe Bonnet, Maher Y. Elsheikh, Brett L. Van Horn, Laurent Abbas
  • Patent number: 7884255
    Abstract: 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: Grant
    Filed: August 26, 2005
    Date of Patent: February 8, 2011
    Inventor: Vicki Hedrick
  • Publication number: 20110001080
    Abstract: 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: Application
    Filed: March 6, 2009
    Publication date: January 6, 2011
    Applicant: ARKEMA INC.
    Inventors: Brett L. Van Horn, Maher Y. Elsheikh, Benjamin Bin Chen, Philippe Bonnet
  • Publication number: 20100320428
    Abstract: 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: Application
    Filed: August 30, 2010
    Publication date: December 23, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Matthew H. Luly, Robert G. Richard
  • Patent number: 7795480
    Abstract: 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: Grant
    Filed: July 24, 2008
    Date of Patent: September 14, 2010
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Publication number: 20100139274
    Abstract: 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: Application
    Filed: December 3, 2009
    Publication date: June 10, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Gary Zyhowski, Ryan Hulse, Haridasan K. Nair, David Nalewajek, Rajiv R. Singh
  • Publication number: 20100113629
    Abstract: 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: Application
    Filed: March 28, 2008
    Publication date: May 6, 2010
    Applicant: Arkema Inc.
    Inventors: Brett L. Van Horn, Maher Y. Elsheikh, Benjamin Bin Chen, Philippe Bonnet
  • Publication number: 20090278076
    Abstract: 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: Application
    Filed: March 26, 2009
    Publication date: November 12, 2009
    Applicant: HONEYWELL INTERNATIONAL, INC.
    Inventors: Rajiv R. Singh, Hang T. Pham, Ian Shankland, David P. Wilson, Gary Knopack, David J. Williams
  • Publication number: 20090270522
    Abstract: 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: Application
    Filed: April 23, 2009
    Publication date: October 29, 2009
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Rajiv R. Singh, Ian Shankland, James M. Bowman, David J. Williams
  • Publication number: 20090203945
    Abstract: 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: Application
    Filed: August 21, 2008
    Publication date: August 13, 2009
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Sudip Mukhopadhyay, Cheryl L. Bortz, Kim M. Fleming, Steven D. Phillips, Rajesh K. Dubey
  • Patent number: 7538171
    Abstract: 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: Grant
    Filed: November 18, 2005
    Date of Patent: May 26, 2009
    Assignee: Unimatec Co., Ltd.
    Inventors: Jun Kanega, Ji-Shan Jin, Katsumi Suzuki, Takashi Enokida, Keisuke Kokin
  • Patent number: 7501540
    Abstract: 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: Grant
    Filed: June 29, 2007
    Date of Patent: March 10, 2009
    Assignee: Asahi Glass Company, Limited
    Inventors: Shu-zhong Wang, Takashi Okazoe, Eisuke Murotani, Kunio Watanabe, Daisuke Shirakawa, Kazuya Oharu
  • Publication number: 20090030244
    Abstract: 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: Application
    Filed: July 24, 2008
    Publication date: January 29, 2009
    Applicant: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Publication number: 20080292564
    Abstract: Various compositons, including particularly aerosol compositions, containing fluorinated olefins, including particularly tetra- and penta-fluorpropenes, in a variety of applications are disclosed.
    Type: Application
    Filed: September 4, 2007
    Publication date: November 27, 2008
    Applicant: Honeywell International, Inc.
    Inventors: Rajiv R. Singh, Hang T. Pham, David P. Wilson, Raymond H. Thomas, Mark W. Spatz, David A. Metcalf
  • Publication number: 20080171652
    Abstract: Various compositions, including particularly solvent compositions, containing fluorinated olefins, including particularly tetra- and penta-fluorpropenes, in a variety of applications are disclosed.
    Type: Application
    Filed: September 4, 2007
    Publication date: July 17, 2008
    Applicant: Honeywell International, Inc.
    Inventors: Rajiv R Singh, Raymond H. Thomas, Gary Knopeck
  • Patent number: 7371904
    Abstract: 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: Grant
    Filed: April 29, 2005
    Date of Patent: May 13, 2008
    Assignee: Honeywell International Inc.
    Inventors: Jing Ji Ma, Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
  • Publication number: 20080003127
    Abstract: Disclosed are cover gas compositions comprising fluoroolefins for impeding the oxidation of molten nonferrous metals and alloys, such as magnesium.
    Type: Application
    Filed: March 26, 2007
    Publication date: January 3, 2008
    Applicant: Honeywell International Inc.
    Inventors: Matthew H. Luly, Rajiv R. Singh
  • Patent number: 7304191
    Abstract: 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: Grant
    Filed: August 6, 2001
    Date of Patent: December 4, 2007
    Assignee: Solvay (Societe Anonyme)
    Inventors: Véronique Mathieu, Francine Janssens, James Franklin
  • Patent number: 7241928
    Abstract: 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: Grant
    Filed: October 1, 2004
    Date of Patent: July 10, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur N.Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 7081279
    Abstract: 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: Grant
    Filed: August 29, 2003
    Date of Patent: July 25, 2006
    Assignee: Chisso Corporation
    Inventors: Takashi Kato, Tomoyuki Kondo, Henry Bernhardt, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
  • Publication number: 20040127756
    Abstract: 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: Application
    Filed: October 16, 2003
    Publication date: July 1, 2004
    Applicants: NATIONAL INSTITUTE OF ADVANCED IND. SCIENCE AND TECH., DAIKIN INDUSTRIES, LTD.
    Inventors: Taizo Ono, Masakazu Nishida, Masaharu Okazaki, Kazumi Toriyama, Tetsuo Shimizu
  • Patent number: 6710214
    Abstract: 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: Grant
    Filed: November 12, 2002
    Date of Patent: March 23, 2004
    Assignees: National Institute of Advanced Industrial Science and Technology, Daikin Industries, Ltd.
    Inventors: Taizo Ono, Masakazu Nishida, Masaharu Okazaki, Kazumi Toriyama, Tetsuo Shimizu
  • Patent number: 6692657
    Abstract: 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: Grant
    Filed: June 2, 1999
    Date of Patent: February 17, 2004
    Assignee: Chisso Corporation
    Inventors: Takashi Kato, Tomoyuki Kondo, Henry Bernhardt, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
  • Patent number: 6664431
    Abstract: 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: Grant
    Filed: March 14, 2001
    Date of Patent: December 16, 2003
    Assignee: Zakrytoe Aktsionernoe Obschestvo Nauchno-Proizvodstvennoe Obiedinenie “Pim-Invest”
    Inventors: Sergei Mikhailovich Igumnov, Galina Ivanovna Lekontseva
  • Publication number: 20030216594
    Abstract: 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: Application
    Filed: March 23, 2001
    Publication date: November 20, 2003
    Inventors: Reinhard Georg Hanreich, Herng-Tay Wu, Michael Allen Oliver, Dean Kent Hoglen
  • Publication number: 20030181615
    Abstract: Compounds corresponding to formula (I)
    Type: Application
    Filed: March 6, 2003
    Publication date: September 25, 2003
    Inventors: Bruno Michel Ameduri, Michel armand, Mario Boucher, Abdellatif Manseri
  • Patent number: 6255543
    Abstract: 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: Grant
    Filed: December 5, 2000
    Date of Patent: July 3, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Zhen-Yu Yang
  • Patent number: 6229058
    Abstract: 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: Grant
    Filed: August 28, 1997
    Date of Patent: May 8, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Allen Capron Sievert, Mario Joseph Nappa
  • Patent number: 6156943
    Abstract: 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: Grant
    Filed: October 30, 1998
    Date of Patent: December 5, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Viacheslav Alexandrovich Petrov
  • Patent number: 6072088
    Abstract: 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: Grant
    Filed: August 10, 1999
    Date of Patent: June 6, 2000
    Assignee: Alliedsignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5914423
    Abstract: 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: Grant
    Filed: November 24, 1997
    Date of Patent: June 22, 1999
    Assignee: Zeneca, Limited
    Inventors: Michael Drysdale Turnbull, Nigel James Willetts, Steven Fitzjohn, Prafula Govind Kholia, Harjindersingh Bansal, Alfred Glyn Williams
  • Patent number: 5877357
    Abstract: 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: Grant
    Filed: April 7, 1997
    Date of Patent: March 2, 1999
    Assignee: Ausimont S.p.A.
    Inventors: Antonio Marraccini, Antonio Pasquale, Tiziana Fiorani, Walter Navarrini
  • Patent number: 5777184
    Abstract: 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: Grant
    Filed: June 25, 1997
    Date of Patent: July 7, 1998
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Alagappan Thenappan
  • Patent number: 5750808
    Abstract: 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: Grant
    Filed: July 9, 1996
    Date of Patent: May 12, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Wendell Richard Cassel, David Richard Corbin, V.N. Mallikarjuna Rao
  • Patent number: 5714654
    Abstract: 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: Grant
    Filed: December 8, 1995
    Date of Patent: February 3, 1998
    Assignee: Daikin Industries Ltd.
    Inventors: Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Tatsuo Nakada
  • Patent number: 5714649
    Abstract: 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: Grant
    Filed: December 20, 1995
    Date of Patent: February 3, 1998
    Assignee: Shin-Etsu Chemical CO., Ltd.
    Inventors: Takehiko Fukumoto, Daisuke Iwai, Shigeo Okano, Hiroshi Suzuki, Mitsuyoshi Oshima
  • Patent number: 5681902
    Abstract: 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: Grant
    Filed: January 11, 1996
    Date of Patent: October 28, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Donald Douglas May
  • Patent number: 5654473
    Abstract: 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: Grant
    Filed: March 16, 1995
    Date of Patent: August 5, 1997
    Assignee: AlliedSignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5648560
    Abstract: 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: Grant
    Filed: December 9, 1994
    Date of Patent: July 15, 1997
    Assignee: Ausimont S.p.A.
    Inventors: Antonio Marraccini, Antonio Pasquale, Tiziana Fiorani, Walter Navarrini
  • Patent number: 5585517
    Abstract: 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: Grant
    Filed: April 12, 1995
    Date of Patent: December 17, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Ted Deisenroth, Robert Falk, Juerg Haase
  • Patent number: 5557018
    Abstract: 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: Grant
    Filed: September 13, 1995
    Date of Patent: September 17, 1996
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Bruce E. Smart, Zhen-Yu Yang
  • Patent number: 5532419
    Abstract: 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: Grant
    Filed: September 15, 1995
    Date of Patent: July 2, 1996
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung
  • Patent number: 5481050
    Abstract: 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: Grant
    Filed: March 28, 1995
    Date of Patent: January 2, 1996
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung
  • Patent number: 5463149
    Abstract: 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: Grant
    Filed: July 12, 1994
    Date of Patent: October 31, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takehiko Fukumoto, Daisuke Iwai, Shigeo Okano, Hiroshi Suzuki, Mitsuyoshi Oshima
  • Patent number: 5446217
    Abstract: 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: Grant
    Filed: May 16, 1994
    Date of Patent: August 29, 1995
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, G. V. Bindu Madhavan, Alagappan Thenappan, Hsueh S. Tung
  • Patent number: 5347058
    Abstract: 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: Grant
    Filed: December 7, 1993
    Date of Patent: September 13, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5342985
    Abstract: 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: Grant
    Filed: August 20, 1990
    Date of Patent: August 30, 1994
    Assignee: Hoechst AG
    Inventors: Wolfgang A. Herrmann, Werner Wagner, Ursula Volkhardt
  • Patent number: 5276221
    Abstract: 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: Grant
    Filed: January 25, 1993
    Date of Patent: January 4, 1994
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 5258561
    Abstract: 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: Grant
    Filed: November 6, 1992
    Date of Patent: November 2, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Mario J. Nappa, V. N. Mallikarjuna Rao