Patents Examined by Alan Siegel
  • Patent number: 6222079
    Abstract: Disclosed is a method of increasing the percentage of certain isomers made when di or tri-substituted benzenes are chlorinated in the presence of a Friedel-Crafts catalyst. The use of about 0.001 to about 1 wt % a cocatalyst during chlorination alters the isomeric ratio of the product mixture. In particular, the percentage of the 2,5-isomer is increased when said substituted benzene is ortho or meta-substituted, the percentage of the 3,4-isomer is increased when said substituted benzene is para-substituted, and the percentage of the 2,4,5-isomer is increased when said substituted benzene is 2,4-disubstituted, 3,4-disubstituted, or 2,5-disubstituted.
    Type: Grant
    Filed: October 28, 1999
    Date of Patent: April 24, 2001
    Assignee: Occidental Chemical Corporation
    Inventors: Dean R. Lagerwall, Pravin M. Khandare, Hang-Chang Bobby Chen, Mark F. Lechner
  • Patent number: 6218587
    Abstract: Catalytic hydrogenolysis of fluorohalocarbons (e.g., CFCs) and fluorohalohydrocarbons (e.g., HCFCs), using low-phosphorous, low-sulfur catalysts of Re, Co, Ni, Ru, Rh, Pd, Os, Ir, and/or Pt on carbon. Preferred catalysts are acid-washed and also have a low content of potassium, sodium and iron.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: April 17, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: V. N. Mallikarjuna Rao
  • Patent number: 6218586
    Abstract: The invention relates to a method for preparing a fluorinated product that is a first perhalogenated five-membered cyclic compound (e.g., 1,2-dichlorohexafluorocyclopentene and 1,1-dichlorooctafluorocyclopentane). This method includes reacting in a gas phase a starting material that is a second perhalogenated five-membered cyclic compound having at least one unsaturated bond, at substantially the same time with chlorine and hydrogen fluoride, in the presence of a fluorination catalyst containing an activated carbon optionally carrying thereon a metal compound, thereby to decrease the number of the at least one unsaturated bond and to increase the number of fluorine atoms of the second compound. The method is appropriate for the production of the first perhalogenated five-membered cyclic compound in an industrial scale.
    Type: Grant
    Filed: November 5, 1999
    Date of Patent: April 17, 2001
    Assignees: Central Glass Company, Limited, Nippon Zeon Co., Ltd.
    Inventors: Naoto Takada, Masatomi Kanai, Hideaki Imura, Takeo Komata
  • Patent number: 6215032
    Abstract: It has been found possible to separate catalytically-active aminophosphonium catalysts from mixtures composed predominately of aminophosphonium catalyst residue(s) and heavy ends from a halogen exchange reaction conducted in an aprotic solvent/diluent by extracting such mixtures with a neutral or acidic aqueous extraction solvent medium. Various ways of isolating from the halogen exchange reaction product mixture a mixture composed predominately of aminophosphonium catalyst residue(s) and heavy ends are described. Halogen exchange processes in which the catalytically-active aminophosphonium catalysts are separated for reuse are also described. Since aminophosphonium catalysts are expensive, the present process technology fulfills a need which has existed for an effective way of recovering such catalysts in catalytically active form enabling reuse of such materials, especially as halogen exchange catalysts.
    Type: Grant
    Filed: February 10, 1998
    Date of Patent: April 10, 2001
    Assignee: Albemarle Corporation
    Inventors: Chi Hung Cheng, John F. Balhoff, Ronny W. Lin
  • Patent number: 6211420
    Abstract: In a process for preparing a fluorinated olefin having a carbon—carbon double bond, the carbon atoms of which have a fluorine atom, by reacting a halogenated olefin having at least one carbon—carbon double bond, a carbon atom or the carbon atoms of which bond have a chlorine atom or atoms bound thereto, and, in which the carbon atom or atoms with a single bond in the molecule have no halogen atom other than a fluorine atom, with an alkali metal fluoride, said reaction of the halogenated olefin with the alkali metal fluoride is conducted in the presence of an organic halogen-containing compound having a carbon—carbon single bond, a carbon or the carbons of which have at least one halogen atom other than fluorine atom.
    Type: Grant
    Filed: November 13, 1998
    Date of Patent: April 3, 2001
    Assignee: Japan as represented by Director General of Agency of Industrial Science and Technology
    Inventors: Akira Sekiya, Toshiro Yamada, Mitsuru Sugawara
  • Patent number: 6211421
    Abstract: An uncatalyzed liquid phase process is provided for producing 1,1,1-trifluoropropene via the fluorination of 1,1,3-trichloro-1-propene.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: April 3, 2001
    Assignee: Atofina Chemicals, Inc.
    Inventors: Maher Y. Elsheikh, Bin Chen
  • Patent number: 6206819
    Abstract: N,N-disubstituted formamides, wherein the substituents are selected to provide formamides which have low volatility, are useful as halogenation catalysts. Such catalysts are generally less hazardous to use than typical formamide halogenation catalysts because toxic catalyst by-products are also less volatile. Methods for using such catalysts are provided.
    Type: Grant
    Filed: May 15, 2000
    Date of Patent: March 27, 2001
    Assignee: Rohm and Haas Company
    Inventors: Deborah Diane Graves, Thomas Duncan Rose, David James Swank, Charles Chao Wu
  • Patent number: 6207869
    Abstract: The instant invention relates to producing perhalofluorobutanes and perhalofluorohexanes, more particularly it relates to their production by utilizing tetrafluoroethylene (hereinafter referred to as “TFE”) and chlorotrifluoro-ethylene (hereinafter referred to as “CTFE”) with selected perhalofluoroethanes containing 2 to 4 nonfluorine halogen and 2 to 4 fluorine substituents in the presence of a polyvalent metal halide such as an aluminum chloride or chlorofluoride as catalyst.
    Type: Grant
    Filed: March 7, 2000
    Date of Patent: March 27, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Allen Capron Sievert
  • Patent number: 6204418
    Abstract: A process is provided for the chlorination of aliphatic hydrocarbons containing 1 to 4 carbon atoms using hydrogen chloride as the source of chlorine. The process comprises reaction steps operated in tandem in separate zones. First, an unsaturated aliphatic fluorocarbon is oxychlorinated to give the corresponding saturated perchlorofluorocarbon and water, and second, the saturated perchlorofluorocarbon is reacted in the vapor phase with a hydrocarbon to produce the desired chlorinated hydrocarbon, hydrogen chloride and the unsaturated aliphatic fluorocarbon, third, hydrogen chloride and unsaturated aliphatic fluorocarbon are separated from the chlorinated hydrocarbon and recycled to the first step, and fourth, the chlorinated hydrocarbon is further purified by subjecting it to addition chlorination to convert traces of unsaturated aliphatic fluorocarbon to the corresponding saturated perchlorofluorocarbon, which is separated and recycled to the second step.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: March 20, 2001
    Inventor: John E. Stauffer
  • Patent number: 6204419
    Abstract: Process and apparatus for preparing 1,2-Dichloroethane by direct chlorination If in the reaction of ethylene with chlorine to form 1,2-dichloroethane (EDC) the catalyst components sodium chloride and iron(III) chloride are used in a molar ratio of below 0.5, then the EDC is obtained in sufficiently high purity to allow direct conversion to vinyl chloride. With maintenance of the stated molar ratio the reaction can be carried out very advantageously in terms of equipment and energy consumption, for example by vaporizing some of the EDC in an expansion vessel.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 20, 2001
    Assignee: Vinnolit Technologie GmbH & Co. KG
    Inventors: Jürgen Eichler, Reinhard Krumböck, Wenzel Kühn, Peter Schwarzmaier, Thomas Wild, Rudolf Spielmannleitner, Manfred Stöger, Ingolf Mielke
  • Patent number: 6201161
    Abstract: Disclosed is a method of removing about 0.05 to about 20 mole % of a benzaldehyde or benzotrihalide from a mixture with a liquid compound that boils within about −10 to about ±5° C. of the boiling point of the benzaldehyde or benzotrihalide. To the mixture is added a benzotrihalide in an amount about stoichiometric to about 10 mole % in excess of stoichiometric, or, respectively, a benzaldehyde in an amount about stoichiometric with the amount of said benzotrihalide, where said benzaldehyde and said benzotrichloride react to form a benzalhalide and a benzoylhalide. The product mixture is distilled to isolate the products.
    Type: Grant
    Filed: April 17, 2000
    Date of Patent: March 13, 2001
    Assignee: Occidental Chemical Corporation
    Inventors: Pravin M. Khandare, Dean R. Lagerwall, Daniel R. Thielen
  • Patent number: 6198011
    Abstract: A method of fluorinating an organic compound comprising reacting an organic compound with a fluorinating agent characterized in that a perfluorocarbon compound is present in the reaction medium. The perfluorocarbon compound may replace an amount of a solvent which would otherwise be required for the reaction to proceed efficiently. The perfluorocarbon compound is readily recoverable after reaction and may be re-used in subsequent reactions. Additives to the reaction medium, such as 18-crown-6, may increase the amoun of solvent which may be replaced. The method is beneficial where solvent consumption would otherwise be large, or where solvent recovery would otherwise be difficult.
    Type: Grant
    Filed: March 25, 1999
    Date of Patent: March 6, 2001
    Assignee: F2 Chemicals Ltd.
    Inventors: Richard D. Chambers, Andrew R. Edwards
  • Patent number: 6198010
    Abstract: The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes a first step of fluorinating 1-chloro-3,3,3-trifluoropropene in a liquid phase by hydrogen fluoride in the presence of an antimony compound as a catalyst, or a second step of fluorinating 1-chloro-3,3,3-trifluoropropene in a gas phase by hydrogen fluoride in the presence of a fluorination catalyst. If the first step is taken, 1,1,1,3,3-pentafluoropropane can be produced with a high yield. If the second step is taken, 1,1,1,3,3-pentafluoropropane can continuously be easily produced. Therefore, the second step is useful for an industrial scale production thereof. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. This method is useful, because yield of 1-chloro-3,3,3-trifluoropropene is high.
    Type: Grant
    Filed: October 6, 1998
    Date of Patent: March 6, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Satoshi Yoshikawa, Ryouichi Tamai, Fuyuhiko Sakyu, Yasuo Hibino, Yoshihiko Gotoh
  • Patent number: 6194620
    Abstract: Dichloro-tetrafluoro-[2,2]-paracyclophane (formula I), which is a novel compound useful as a material for forming a coating film by chemical vapor deposition, and a process for manufacturing thereof and poly-&agr;&agr;-difluoro-chloro-para-xylylene film prepared therefrom are disclosed. Dichloro-tetrafluoro-[2,2]-paracyclophane is manufactured by chlorinating tetrafluoro-[2,2]-paracyclophane. The film to be formed by chemical vapor deposition of dichloro-tetrafluoro-[2,2]-paracyclophane has remarkably improved thermostability, as compared with the conventional products and is expected to be applied in various fields.
    Type: Grant
    Filed: January 27, 1997
    Date of Patent: February 27, 2001
    Assignee: Daisan Kasei Kabushiki Kaisha
    Inventor: Hiroshi Maruyama
  • Patent number: 6194619
    Abstract: A catalyic process is disclosed for producing fluorine-substituted hydrocarbon products of the formulae RCH2CF2R and RFC═CHR at an elevated temperature, from compounds of the formula RCHFCHFR, where each R is independently selected from the group consisting of —CF3, —CF2CF3 and —CF2CF2CF3 or where both R groups of a formula together are —(CF2)2—, —(CF2)3— or —(CF2)4—. Suitable catalysts include carbon catalysts and catalysts containing at least one compound of a selected metal (e.g., Na, K, Rb, Cs, Y, La, Ce, Pr, Nd, Sm, Cr, Fe, Co, Rh, Ni, Cu, and/or Zn) supported on carbon. The saturated gem-dihydro- products may also be produced by hydrofluorinating the corresponding olefinic product over such catalysts at an elevated temperature, and can be combined with various other miscible solvents to form compositions useful for cleaning.
    Type: Grant
    Filed: September 10, 1993
    Date of Patent: February 27, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: V. N. Mallikarjuna Rao, Frank Julian Weigert, Carl G. Krespan
  • Patent number: 6191329
    Abstract: A process for specific energy saving, especially in processes involving the oxychlorination of ethylene, facilitates recovery of as much sensible heat to be used for other purposes. In the process the gas mixture leaving the oxychlorination reactor is cooled before it enters the quenching column and the heat recovered is then used to preheat the ethylene recycle gas feed stream.
    Type: Grant
    Filed: July 29, 1999
    Date of Patent: February 20, 2001
    Assignee: Krupp Uhde GmbH
    Inventor: Michael Benje
  • Patent number: 6191328
    Abstract: HFC-245fa is effectively separated from the mixture comprising 1,1,1,3,3-pentafluoropropane (HFC-245fa) and HF through a purification process comprising contacting at least one extraction agent selected from the group consisting of (a) a compound corresponds to the general formula (I): CxFyHz, (b) a compound corresponds to the general formula (II): R1R2R3N, (c) an compound corresponds to the general formula (III): R4OR5 and (d) a compound corresponds to the general formula (IV): ClClmHn with a mixture comprising 1,1,1,3,3-pentafluoropropane and hydrogen fluoride so as to form a liquid mixture and separating the liquid mixture into two liquid layers, followed by obtaining an extraction agent phase including HFC-245fa and the extraction agent as the main components, and separatively recovering HFC-245fa from the extraction agent phase.
    Type: Grant
    Filed: December 22, 1998
    Date of Patent: February 20, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Keisuke Kitano, Tatsuo Nakada, Takashi Shibanuma
  • 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: 6187975
    Abstract: Perfluoropropene (PFP) hydrofluorination process in gaseous phase to obtain CF3—CHF—CF3 (A-227ea), characterized in that as catalyst fluorinated alumina containing at least 90% by weight of AlF3, is used, the HF/PFP molar ratios range from about 4:1 to 20:1, the hydrofluorination process temperature being in the range 320°-420° C.
    Type: Grant
    Filed: June 16, 1999
    Date of Patent: February 13, 2001
    Assignee: Ausimont S.p.A.
    Inventors: Letanzio Bragante, Paolo Cuzzato