Utilizing Unsaturated Compound Patents (Class 570/172)
  • Publication number: 20040034259
    Abstract: A method of simultaneous and selective perpararation of hexafluoropropylene and octafluorocyclebutane comprising the steps of:
    Type: Application
    Filed: August 14, 2002
    Publication date: February 19, 2004
    Inventors: Dong Ju Moon, Moon Jo Chung, Young Soo Kwon, Byoung Sung Ahn
  • Patent number: 6518467
    Abstract: A method of producing hydrofluorocarbons and/or hydrochlorofluorocarbons by using halogenated alkanes as a principal reactant. Generally, the method comprises the step of: (a) reacting a starting halogenated alkane corresponding to the formula (I): H3C—CX3  (I) wherein X is independently fluorine or chlorine, with a hydrohalocarbon adduct in the presence of a catalyst to form a hydrofluorocarbon and/or hydrochlorofluorocarbon.
    Type: Grant
    Filed: December 29, 2000
    Date of Patent: February 11, 2003
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Michael Van Der Puy
  • Patent number: 6472574
    Abstract: CF3CHFCHF2 production is disclosed which involves reacting CF3CF═CHF with HF at an elevated temperature over a catalyst selected from the group consisting of aluminum fluoride, fluorided alumina, metals supported on aluminum fluoride, metals supported on fluorided alumina and catalysts comprising trivalent chromium. Also disclosed is enrichment of CF3CF═CHF from a starting mixture containing CF3CF═CHF and CF3CH═CF2 which involves reacting said starting mixture with HF at an elevated temperature over a catalyst consisting essentially carbon, a catalyst consisting essentially of metal halides supported on carbon, a catalyst consisting essentially of Cr2O3, or mixtures thereof (provided that when Cr2O3 is present the temperature is about 250° C. or less) to produce a product mixture containing CF3CH2CF3 and unreacted CF3CF═CHF wherein the mole ratio of CF3CF═CHF to CF3CH═CF2 is greater than the ratio thereof in the starting mixture.
    Type: Grant
    Filed: March 11, 2002
    Date of Patent: October 29, 2002
    Assignee: E. I. du Pont Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Francis John Walczak
  • Patent number: 6452057
    Abstract: Halohydrocarbons comprising at least 3 carbon atoms are obtained by batchwise reaction between a haloalkane and an olefin in the presence of a catalyst and a co-catalyst. The addition of at least some of the co-catalyst is carried out gradually. At least some of the co-catalyst is recovered with a view to its re-use.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: September 17, 2002
    Assignee: Solvay (Societe Anonyme)
    Inventors: Alain Lambert, Véronique Mathieu, Charles-Marie Anciaux
  • Patent number: 6448452
    Abstract: A polymer which contains monomer units formed by polymerization of a fluorine-containing diene of formula 1: CF2═CF(CF2)nCXYOCF═CF2 Wherein X and Y are hydrogen and chlorine, hydrogen and-bromine, hydrogen and iodine, fluorine and chlorine, fluorine and bromine, fluorine and iodine, chlorine and bromine, chlorine and iodine, bromine and bromine, bromine and iodine, or iodine and iodine and n is an integer from 1 to 3.
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: September 10, 2002
    Assignee: Asahi Glass Company Limited
    Inventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
  • Patent number: 6441256
    Abstract: Halohydrocarbons comprising at least 3 carbon atoms are obtained by reaction between a haloalkane and a haloolefin, in the substantial absence of nitrile, and by introducing the reactants in a molar ratio between the haloalkane and the haloolefin of less than 2. 1,1,1,3,3-Pentachloropropane can thus be obtained in good voluminal yield.
    Type: Grant
    Filed: March 20, 2000
    Date of Patent: August 27, 2002
    Assignee: Solvay (Societe Anonyme)
    Inventors: Véronique Mathieu, Francine Janssens
  • Patent number: 6417413
    Abstract: A process for preparing halogenated ethanes, particularly pentafluoroethane, from a mixture produced by the reaction of perchloroethylene, hydrogen fluoride and a recycle stream. The preferred process utilizes phase separation techniques to ensure that less than the azzeotropic amount of HF is included in the product stream, thereby minimizing the hydrogen fluoride that is carried off with the desired products after they are separated from the reaction mixture, and at the same time prevents undesirable byproducts from being recycled to the reaction.
    Type: Grant
    Filed: November 3, 1999
    Date of Patent: July 9, 2002
    Assignee: AlliedSignal Inc.
    Inventors: Gustavo Cerri, Yuon Chiu, Biju Z. Perincheril
  • Patent number: 6399839
    Abstract: Halohydrocarbons comprising at least 3 carbon atoms are obtained by reaction between a haloalkane and an olefin in the presence of an organocopper compound as catalyst, a solvent and/or a cocatalyst. 1,1,1,3,3-Penta-chloropropane can thus be obtained in good yield under mild conditions.
    Type: Grant
    Filed: November 3, 1999
    Date of Patent: June 4, 2002
    Assignee: Solvay (Societe Anonyme)
    Inventors: Véronique Mathieu, Francine Janssens
  • Patent number: 6399840
    Abstract: 1,1,1,3,3-pentachlorobutane is obtained by reacting carbon tetrachloride with 2-chloro-1-propene in the presence of at least one copper (I) or (II) compound as telomerization catalyst. Advantageously, a polar compound can be present in the reaction mixture as solvent, and an amine, an amide or a trialkylphosphine oxide can be present as cocatalyst.
    Type: Grant
    Filed: December 30, 1999
    Date of Patent: June 4, 2002
    Assignee: Solvay (Societe Anonyme)
    Inventors: Jean-Paul Schoebrechts, Véronique Mathieu, Francine Janssens
  • Patent number: 6369285
    Abstract: Halohydrocarbons containing at least 3 carbon atoms are obtained by reaction between a haloalkane and an olefin in the presence of a catalyst in a reaction medium which is essentially free of water.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: April 9, 2002
    Assignee: Solvay (Societe Anonyme)
    Inventors: Véronique Mathieu, Charles-Marie Anciaux
  • Patent number: 6365676
    Abstract: The invention concerns a process for the reaction of a perfluoroalkyl iodide of the formula CF3(CF2)h—I, where h is an integer from 4 to 18, with a compound having a terminal olefinic group, which comprises conducting said reaction in an aqueous medium containing 5 to 40% by weight of a water-soluble solvent and in the presence of from 0.02 to 0.5 equivalents of dithionite ion, based on the perfluoroalkyl iodide, at a temperature of from 0 to 40° C. and at a pH greater than 7.0.
    Type: Grant
    Filed: October 16, 2000
    Date of Patent: April 2, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: John Jennings, Ted Deisenroth, Marlon Haniff
  • Patent number: 6300532
    Abstract: A process for catalytic addition of haloalkanes to alkenes involving the step of reacting the haloalkane with the alkene in the presence of a catalyst. The catalyst is an organophosphite compound represented by the following formula: P(ORa)(ORb)(ORc), where Ra, Rb, and Rc are each an alkyl group or an aralkyl group.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: October 9, 2001
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Timothy Rech Demmin
  • Patent number: 6291730
    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═C3R4 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: January 28, 1998
    Date of Patent: September 18, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ralph Thomas Baker, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 6191327
    Abstract: The present invention relates to a simple method for producing 3,3-dichloro-1,1,1,2,2-pentafluoropropane (R225ca) and 1,3-dichloro-1,1,2,2,3-pentafluoropropane (R225cb) in good yield and at high selectivity by reacting tetrafluoroethylene (C2F4) and dichlorofluoromethane (R21) in the presence of a certain specific catalyst. The specific catalyst in the present invention is (1) a catalyst comprising halogenated oxide containing at least one element of Group 4, Group 5 and Group 13 such as Ti, Zr, Hf, V, B and Ga, or (2) a catalyst comprising halogenated oxide containing at least one element selected from Group 4, Group 5 and Group 13 such as Ti, Zr, Hf, V, B, Al and Ga and at least one element selected from Group 2, Group 6, Group 12 and Group 14 such as Ba, W, Zn, Si, Bi and P.
    Type: Grant
    Filed: November 26, 1993
    Date of Patent: February 20, 2001
    Assignee: Asahi Glass Company Ltd.
    Inventors: Shinsuke Morikawa, Keiichi Ohnishi, Hidekazu Okamoto, Toshihiro Tanuma
  • Patent number: 6187978
    Abstract: A process for preparing a haloalkane comprising: (a) contacting a haloalkane starting material with a haloalkene starting material in the presence of an effective amount of a catalyst complex under conditions effective to facilitate an addition reaction and to form a product stream comprising a haloalkane product from said addition reaction, wherein said catalyst complex has a boiling point higher than that of said haloalkane product; and (b) recovering said haloalkane product from said product stream.
    Type: Grant
    Filed: May 12, 1999
    Date of Patent: February 13, 2001
    Assignee: AlliedSignal Inc.
    Inventors: Tedeusz P. Rygas, Hsuch Sung Tung
  • Patent number: 6184426
    Abstract: A process is disclosed for forming adducts of the formula: RR1R2CCR1R2F or (FR1R2CCRR2CH2)2 where R is CH3, CH2F, or F(CF2)nCH2CH2 (where n is an integer from 1 to 10) each R1 is H, Cl, F or CF3 and each R2 is H, F or CF3. The process in reacting a saturated compound of the formula RF with an olefin of the formula R1R2C═CR1R2 in the liquid phase in the presence of antimony pentafluoride catalyst (provided that when (FR1R2CCR1R2CH2)2 is formed, the saturated compound is CH3CHF2 or CH2FCH2F and anhydrous HF is present).
    Type: Grant
    Filed: September 21, 1999
    Date of Patent: February 6, 2001
    Assignee: DISA
    Inventors: Gennadii G. Belen'Kill, Viacheslav A. Petrov, Paul R. Resnick
  • Patent number: 6153803
    Abstract: Halohydrocarbons comprising at least 3 carbon atoms are obtained by reaction between a haloalkane and a haloolefin in the presence of an organonickel compound as catalyst, and optionally in the presence of a solvent. 1,1,1,3,3-Pentachlorobutane can thus be obtained in good yield under mild conditions.
    Type: Grant
    Filed: June 1, 1998
    Date of Patent: November 28, 2000
    Assignee: Solvay Societe Anonyme
    Inventor: Jean-Paul Schoebrechts
  • Patent number: 6150565
    Abstract: A process is disclosed for making diiodofluorinated compounds of the formula ICF.sub.2 (A).sub.n I wherein n is an integer of at least 1 and each A is CXYCQZ wherein each X, Y, Q, and Z are each independently selected from the group consisting of H, F, Cl, R.sub.F and OR.sub.F, and R.sub.F is a perfluoroalkyl group or perfluorinated polyether group wherein one or more of the fluorines is optionally replaced by a substituent selected from the group consisting of chlorine, bromine, iodine, hydrogen, sulfonyl fluoride, nitrile, ester, acyl chloride and acyl fluoride. The process involves reacting an olefin of the formula CXY.dbd.CQZ with CF.sub.2 I.sub.2 at a temperature in the range of from about 120.degree. C. to 240.degree. C.Diiodofluorinated compounds of the formula ICF.sub.2 CH.sub.2 CHR.sub.F I are also disclosed.
    Type: Grant
    Filed: September 8, 1998
    Date of Patent: November 21, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Zhen-Yu Yang
  • Patent number: 6040487
    Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula: CAR.sup.1 R.sup.2 CBR.sup.3 R.sup.4 (where, A, B, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR.sup.1 R.sup.2 .dbd.CR.sup.3 R.sup.4, in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper, and (ii) a promoter selected from aromatic or aliphatic hetercyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, hydrofluorocarbons may be formed therefrom by reacting the hydrochlorofluorocarbons with HF.
    Type: Grant
    Filed: January 28, 1998
    Date of Patent: March 21, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ralph Thomas Baker, Viacheslav Alexandrovich Petrov, Velliyurnott Mallikarjuna Rao
  • Patent number: 5902914
    Abstract: A process for the preparation of halogenated alkanes is provided. In particular, a process is provided for the highly selective preparation of haloalkanes, including 1,1,1,3,3-pentachloropropane, pentachlorobutane, and hepatchlorohexane, in good yield.
    Type: Grant
    Filed: August 14, 1995
    Date of Patent: May 11, 1999
    Assignee: AlliedSignal Inc.
    Inventors: Tadeusz Piotr Rygas, Hsueh Sung Tung, Addison Miles Smith
  • Patent number: 5650545
    Abstract: The invention relates to a continuous process for the preparation of perfluoroalkyl iodides by thermal telomerization, in the gas phase, of tetrafluoroethylene with pentafluoroethyl iodide or heptafluoroisopropyl iodide in a tubular reactor.To improve the selectivity for a telomer of the desired extent, the telomers of lesser extent are recycled to at least one point in the reactor, which is situated between one-twentieth and three-quarters the length of the tube.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: July 22, 1997
    Assignee: Elf Atochem S.A.
    Inventors: Rene Bertocchio, Patrick Lambert, Georges Lacote
  • Patent number: 5639923
    Abstract: The selectivity of copper as the catalyst for the reaction of short-chain perfluoroalkyl iodides with tetrafluoroethylene is increased if a further transition metal is employed as a cocatalyst.
    Type: Grant
    Filed: December 21, 1995
    Date of Patent: June 17, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Konrad Von Werner
  • Patent number: 5608126
    Abstract: A process for preparing 1,1,1,3,3-pentafluoropropane, which comprises reacting 1,1-difluoroethylene with dichlorofluoromethane in the presence of a Lewis acid catalyst to form 1,2,2-trihydrodichlorotrifluoropropane and fluorinating the 1,2,2-trihydrodichlorotrifluoropropane with hydrogen fluoride.
    Type: Grant
    Filed: June 23, 1995
    Date of Patent: March 4, 1997
    Assignee: AG Technology Co., Ltd.
    Inventors: Shinsuke Morikawa, Hidekazu Okamoto, Keiichi Ohnishi, Shin Tatematsu
  • Patent number: 5574193
    Abstract: This invention relates to the telomerization of polyfluoroalkyl iodides with polyfluoroolefins in the presence of strong fluorooxidizer initiators. The products obtained are useful in the production of surfactants and oil repellants.
    Type: Grant
    Filed: April 4, 1995
    Date of Patent: November 12, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Carl G. Krespan, Viacheslav A. Petrov, Bruce E. Smart
  • Patent number: 5557019
    Abstract: A new 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane as a precursor of alternatives of refrigerants, etc.A method to obtain the target products at high yield and high selectivity by reacting tetrafluoroethylene and difluorodichloromethane under the Lewis acid catalyst to produce the new compound and an economical method in a continuous reaction state.A production method of 1,1,1,2,2,4,4,5,5,5-decafluoropentane at high yield by reducing 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane.
    Type: Grant
    Filed: August 24, 1994
    Date of Patent: September 17, 1996
    Assignee: Daikin Industries Ltd.
    Inventors: Hirokazu Aoyama, Satoru Kohno, Satoshi Koyama
  • Patent number: 5488189
    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: December 14, 1993
    Date of Patent: January 30, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Allen C. Sievert, Mario J. Nappa
  • 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: 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: 5434321
    Abstract: A method for producing a dichloropentafluoropropane, which comprises reacting dichlorofluoromethane (R21) with tetrafluoroethylene (4F) in the presence of a Lewis acid catalyst for addition reaction to obtain dichloropentafluoropropane, wherein a halide containing at least one element selected from the group consisting of Sb, Nb, Ta, B, Ga, In, Zr, Hf and Ti, or AlBr.sub.3, or AlI.sub.3, is used as the Lewis acid.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: July 18, 1995
    Assignee: Asahi Glass Company Ltd.
    Inventors: Keiichi Ohnishi, Hidekazu Okamoto, Toshihiro Tanuma, Koichi Yanase, Toru Kawasaki, Ryutaro Takei
  • Patent number: 5395997
    Abstract: The invention relates to a process for preparing hydrofluorocarbons of the formulas CF.sub.3 (CH.sub.2 CF.sub.2).sub.n F comprising reacting at least one reactant selected from CCl.sub.3 (CH.sub.2 CCl.sub.2).sub.n Cl, CCl.sub.3 (CH.sub.2 CF.sub.2).sub.n Cl or CCl.sub.2 [(CH.sub.2 CF.sub.2)Cl].sub.2, where n=1 to 3, with hydrogen fluoride at a temperature of from about 25.degree. to about 200.degree. C.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: March 7, 1995
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, G. V. Bindu Madhavan, Timothy R. Demmin
  • Patent number: 5326913
    Abstract: A fluorinated compound of the formula:R--CCl.sub.2 CF.sub.2 CF.sub.3 (I)in which R is a perfluoroalkyl group, a perchloroalkyl group, a polyfluoroalkyl group, a polychloroalkyl group or a polychloropolyfluoroalkyl group, each having at least one carbon atom is prepared at a high selectivity and a high yield by reacting tetrafluoroethylene with a compound of the formula:R--CFCl.sub.2 (II)in which R is the same as defined above in the presence of a Lewis acid.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: July 5, 1994
    Assignee: Daikin Industries Ltd.
    Inventors: Hirokazu Aoyama, Satoshi Koyama
  • Patent number: 5254773
    Abstract: A process is disclosed wherein a telomer having the formula BrCH.sub.2 CH.sub.2 (CF.sub.2 CFX).sub.n CH.sub.2 CH.sub.2 Br is prepared by reacting a telogen of the formula Br(CF.sub.2 CFX).sub.n CH.sub.2 CH.sub.2 Br with ethylene in the presence of an organic free-radical generator, wherein X is fluorine or a trifluoromethyl radical and n is an integer having a value of 1-5. It has been found that, when at least 0.05 mole of said free-radical generator is used for each mole of said telogen, the conversion of the telogen to the telomer is surprisingly increased.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: October 19, 1993
    Assignee: Dow Corning Corporation
    Inventor: Antony P. Wright
  • Patent number: 5227547
    Abstract: A method for producing a dichloropentafluoropropane, which comprises reacting dichlorofluoromethane (R21) with tetrafluoroethylene (4F) in the presence of a Lewis acid catalyst for addition reaction to obtain dichloropentafluoropropane, wherein a halide containing at least one element selected from the group consisting of Sb, Nb, Ta, B, Ga, In, Zr, Hf and Ti, or AlBr.sub.3, or AlI.sub.3, is used as the Lewis acid.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: July 13, 1993
    Assignee: Asahi Glass Company Ltd.
    Inventors: Keiichi Ohnishi, Hidekazu Okamoto, Toshihiro Tanuma, Koichi Yanase, Toru Kawasaki, Ryutaro Takei
  • Patent number: 5220084
    Abstract: A method for producing a dichloropentafluoropropane, which comprises reacting dichlorofluoromethane (R21) with tetrafluoroethylene (4F) in the presence of a Lewis acid catalyst for addition reaction to obtain dichloropentafluoropropane, wherein a halide containing at least one element selected from the group consisting of Sb, Nb, Ta, B, Ga, In, Zr, Hf and Ti, or AlBr.sub.3, or AlI.sub.3, is used as the Lewis acid.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: June 15, 1993
    Assignee: Asahi Glass Company Ltd.
    Inventors: Keiichi Ohnishi, Hidekazu Okamoto, Toshihiro Tanuma, Koichi Yanase, Toru Kawasaki, Ryutaro Takei
  • Patent number: 5185483
    Abstract: 1,1,1,2,2-Pentafluoro-3,3-dichloropropane and 1,1,2,2,3-pentafluoro-1,3-dichloropropane are prepared in pure forms by reacting dichlorofluoromethane and tetrafluoroethylene, or chloroform, difluorochloromethane and tetrafluoroethylene in the presence of a catalyst comprising a halogenated zirconium of the formula:ZrCl.sub.x F.sub.y (I)wherein x and y are numbers which satisfy the relationships x+y=4, 0<x.ltoreq.4 and 0.ltoreq.y<4.
    Type: Grant
    Filed: December 23, 1991
    Date of Patent: February 9, 1993
    Assignee: Daikin Industries, Ltd.
    Inventors: Hirokazu Aoyama, Takashi Yasuhara, Satoru Kono, Satoshi Koyama, Souichi Ueda
  • Patent number: 5177274
    Abstract: 1,1,1,2,2-Pentafluoro-3,3-dichloropropane and 1,1,2,2,3-pentafluoro-1,3-dichloropropane are prepared by reacting dichlorofluoromethane and tetrafluoroethylene in a solvent in the presence of a catalyst with improved conversion and selectivity.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: January 5, 1993
    Assignee: Daikin Industries Ltd.
    Inventors: Hirokazu Aoyama, Satoru Kono, Satoshi Koyama
  • Patent number: 5157171
    Abstract: A process for the preparation of chlorofluoropropanes of the formula C.sub.3 HCl.sub.2 F.sub.5 by contacting monofluorodichloromethane with tetrafluoroethylene in the presence of a modified aluminum chloride catalyst at a temperature of 0.degree. to 150.degree. C. The novel compound CF.sub.3 CCl.sub.2 CHF.sub.2 is also disclosed.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: October 20, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Allen C. Sievert, Carl G. Krespan, Frank J. Weigert
  • Patent number: 5087765
    Abstract: In the process for preparing chlorotrifluoroethylene telomers by reaction of chlorotrifluoroethylene with CF.sub.3 CF or R.sub.x --CF.sub.2 OF (wherein R.sub.x may be also a perfluoroalkyl radical having 1 to 10 carbon atoms), the content of telomers with end groups --F is increased or mixtures of telomers containing species with end groups --Cl are obtained by adding F.sub.2, according to particular modalities, to the reaction medium.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: February 11, 1992
    Assignee: Ausimont S.r.L.
    Inventors: Antonio Marraccini, Antonio Pasquale, Marco Vincenti
  • Patent number: 5087745
    Abstract: Process, which is feasible on a commercial scale, for the production of gamma-butyrobetaine. For this purpose, butyrolactone with hydrogen chloride and an alcohol is converted to the chlorobutyric acid ester, the trimethylammonium butyric acid salt is formed with trimethylamine and then saponified to the end product.
    Type: Grant
    Filed: March 12, 1991
    Date of Patent: February 11, 1992
    Assignee: Lonza Ltd.
    Inventors: Peter Hardt, Andrej Stravs, Pius Abgottspon
  • Patent number: 5087777
    Abstract: Novel partially fluorinated alkenes having the Formula: ##STR1## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkenyl or fluoroalkenyl group having 1 to 6 carbon atoms have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.
    Type: Grant
    Filed: December 4, 1990
    Date of Patent: February 11, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Chien C. Li, Kane D. Cook, Rajat S. Basu
  • Patent number: 5059728
    Abstract: Novel partially fluorinated alkanes having the Formula: ##STR1## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms with the proviso that when each R is CF.sub.3, R' is not CF.sub.3 (CF.sub.2).sub.2 -, CH.sub.3 CF.sub.2 -, or CF.sub.3 have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: October 22, 1991
    Assignee: Allied-Signal Inc.
    Inventors: Chien C. Li, Bernard Sukornick
  • Patent number: 5017718
    Abstract: 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: Grant
    Filed: January 26, 1984
    Date of Patent: May 21, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Iwao Ojima, Takamasa Fuchikami
  • Patent number: 4937398
    Abstract: The present invention provides a process for the preparation of luorinated alkanes. The process comprises the step of: reacting an alkene with carbon having fluorine absorbed therein at a temperature and for a time sufficient to form fluorinated alkanes. The alkene used is not perhalogenated at the double-bonded carbons. Preferably, the alkene used is vinylidene fluoride or ethylene.The process produces products such as 1,1,1,2-tetrafluoroethane (known in the art as 134a) which may be used as a refrigerant and 1,1,1-trifluoroethane (known in the art as R143a) and 1,2-difluoroethane (known in the art as R152) which may be used as blowing agents or solvents.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: June 26, 1990
    Assignee: Allied-Signal Inc.
    Inventors: Hsueh S. Tung, Richard E. Eibeck, Bernard Sukornick
  • Patent number: 4873382
    Abstract: A mixture of telomers prepared by reacting chlorotrifluoroethylene with 1,1,2-trichlorotrifluoroethane (CCl.sub.2 FCF.sub.2 Cl) is purified by reacting the telomer mixture with potassium hydroxide in the presence of a quarternery ammonium compound and, optionally, a glycol, separating and removing impurities from the telomer mixture, subsequently reacting the telomer with potassium permanganate in the presence of the quarternery ammonium compound in a solvent, and recovering a purified telomer mixture.If additional purity is required, the purified telomer mixture can be heated to a temperature of from about 150.degree. C. to about 250.degree. C. for at least 12 hours, and impurities formed during the thermal treatment are removed.The purified telomers of this invention find uses in applications requiring the use of non-flammable hydraulic fluids.
    Type: Grant
    Filed: August 22, 1988
    Date of Patent: October 10, 1989
    Assignee: Occidential Chemical Corporation
    Inventors: Bobby F. Dannels, Deborah J. Olsen, John Forcucci
  • Patent number: 4849556
    Abstract: Telomers are prepared by reacting chlorotrifluoroethylene with 1,1,2-trichlorotrifluoroethane (CCl.sub.2 FCF.sub.2 Cl) in the presence of metallic iron or stainless steel, and optionally, a halide-containing compound selected from the group consisting of tetrabutyl ammonium bromide, tetramethyl ammonium chloride, n-chlorosuccinimide, triethylamine hydrochloride, LiCl, MoCl.sub.5 and FeCl.sub.3. The reaction is conducted at a temperature of from about 150.degree. C. to about 200.degree. C. in a nitrile group-containing solvent selected from the group consisting of acetonitrile, propionitrile and ethyl cyanoacetate. Preferably, the CCl.sub.2 FCF.sub.2 Cl and chlorotrifluoroethylene are present in a mole ratio of from about 1:1 to about 3:1. respectively, to minimize the amount of high molecular weight species formed during the reaction. The telomers of this invention are useful for preparing non-flammable hydraulic fluids.
    Type: Grant
    Filed: November 5, 1987
    Date of Patent: July 18, 1989
    Assignee: Occidental Chemical Corporation
    Inventors: Bobby F. Dannels, Deborah J. Olsen
  • Patent number: 4740640
    Abstract: Novel perchlorofluorinated hydrocarbons of the general formula:Cl-(CFX-CF.sub.2).sub.m -CCl.sub.2 -(CF.sub.2 -CFY).sub.n -Clwherein X and Y represent chlorine or fluorine atoms, and m and n are integers from 1 to 5, together with a process for preparing such perchlorofluorocarbons by reacting chlorotrifluoroethylene or tetrafluoroethylene with carbon tetrachloride or a telomer having the formula Cl.sub.3 C-(CF.sub.2 -CFX).sub.m -Cl in a polar solvent at a temperature of at least 120.degree. C. in the presence of copper or a copper salt.
    Type: Grant
    Filed: October 30, 1985
    Date of Patent: April 26, 1988
    Assignee: Atochem
    Inventors: Bernard Boutevin, Yves Hervaud
  • Patent number: 4650913
    Abstract: Reaction of a perfluorinated iodide with an olefin initiated by a sulfinate salt to prepare fluorinated iodide and diiodide monomers and surface active agents.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: March 17, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Andrew E. Feiring
  • Patent number: 4587366
    Abstract: A process is described for preparing fluoroalkyl-substituted iodoalkanes by reacting a fluorinated alkyl iodide with a substituted or unsubstituted alkene under heat in the presence of a catalyst. The catalyst is at least one metal which, in the periodic table of the elements, has one of the atomic numbers 24 to 30, 42 to 48 or 74 to 79 and is in finely divided form. The products of the process according to the invention are addition compounds of the fluorinated alkyl iodide with the substituted or unsubstituted alkene and, in known processes, can be used as useful intermediates for preparing fluorine-containing polymers, textile finishes, fire-extinguishing agents or surfactants.
    Type: Grant
    Filed: October 19, 1984
    Date of Patent: May 6, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Konrad von Werner
  • Patent number: 4478760
    Abstract: The process for making a fluorinated product comprising reacting a perfluoroalkyl iodide and an olefin in the presence of a finely divided zinc and an acidic solvent.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: October 23, 1984
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Hubert Blancou, Auguste Commeyras, Robert Teissedre
  • Patent number: 4377717
    Abstract: Perfluoro-2-methylpentene-2 may be prepared by heating hexafluoropropylene at elevated temperatures in the presence of activated carbon. The activated carbon serves as a catalyst for the dimerization of the hexafluoropropylene.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: March 22, 1983
    Assignee: Allied Corporation
    Inventors: Louis G. Anello, Richard F. Sweeney