Hydrogen Halide Reactant Patents (Class 570/248)
  • Patent number: 9040760
    Abstract: This invention provides a process for producing 2,3,3,3-tetrafluoropropene, the process comprising: (1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and is CI or F, a chloropropene represented by Formula (2): CClY2CCl?CH2, wherein each Y is the same or different and is CI or F, and a chloropropene represented by Formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and is CI or F in a gas phase in the absence of a catalyst while heating; and (2) a second reaction step of reacting hydrogen fluoride with a reaction product obtained in the first reaction step in a gas phase in the presence of a fluorination catalyst while heating. According to the process of this invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be obtained with high selectivity, and catalyst deterioration can be suppressed.
    Type: Grant
    Filed: October 27, 2011
    Date of Patent: May 26, 2015
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
  • Publication number: 20150141713
    Abstract: Provided is a method for preparing vinyl chloride with acetylene and dichlorethane for large-scale industrial production. Acetylene, dichlorethane vapor and hydrogen chloride gas at a molar ratio of 1:(0.3-1.0):(0-0.20) are mixed; the raw mixed gas is preheated; the preheated raw mixed gas passes through a reactor containing a catalyst and reacts; the resultant mixed gas is cooled to 30-50° C. and pressurized to 0.4-1.0 MPa, and then cooled to ambient temperature, and further frozen to ?25-15° C. for liquefaction isolation, and unliquefied gas is recycled and reused; liquefied liquid is sent to a rectifying tower for rectification, and vinyl chloride monomers meeting polymerization requirements are obtained. The present invention has the advantages of eliminating mercury contamination completely, simplifying the reactor structure, recycling hydrogen chloride and acetylene, reducing waterwash process, avoiding mass production of waste acid and improving utilization of chlorine.
    Type: Application
    Filed: July 12, 2012
    Publication date: May 21, 2015
    Applicants: Shanghai Advanced Research Institute, Chinese Academy of Sciences, ZHONGKE YIGONG (SHANGHAI) CHEMICAL TECHNOLOGY CO., LTD.
    Inventors: Biao Jiang, Jinguang Zhong
  • Patent number: 9000239
    Abstract: The present invention provides processes for the production of HCFO-1233zd, 1-chloro-3,3,3-trifluoropropene, from the starting material, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf). In a first process, HCFO-1233zd is produced by the isomerization of HCFO-1233xf. In a second process, HCFO-1233zd is produced in a two-step procedure which includes (i) dehydrochlorination of HCFO-1233xf into trifluoropropyne; and (ii) hydrochlorination of the trifluoropropyne into HCFO-1233zd.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: April 7, 2015
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8921625
    Abstract: A method comprising: providing a halogen stream; providing an alkane stream; providing a decoking agent; and reacting at least a portion of the halogen stream with at least a portion of the alkane stream in the presence of a halogenation catalyst and the decoking agent to form a halogenated stream.
    Type: Grant
    Filed: July 17, 2009
    Date of Patent: December 30, 2014
    Assignee: Reaction35, LLC
    Inventors: Sagar Gadewar, Saydul Amin Sardar, Philip Grosso, Aihua Zhang, Vivek Julka, Peter Stolmanov
  • Patent number: 8816140
    Abstract: The present invention provides a process for producing a fluorine-containing alkene of the general formula CF3(CX2)nCF?CH2, wherein X each independently represents F or Cl, and n is an integer of 0 to 2. The process includes a first reaction step of allowing a specific chlorine-containing compound to react with a fluorinating agent under increased pressure in a gas phase in the presence of at least one fluorination catalyst selected from the group consisting of chromium oxide and fluorinated chromium oxide, and a second reaction step of heating the product of the first reaction step in a gas phase under a pressure lower than the pressure in the first reaction step. The process of the present invention can produce a fluorine-containing alkene with a high selectivity with the use of a catalyst that can be easily handled, while suppressing production of by-products that cannot be easily converted into the target or separated.
    Type: Grant
    Filed: February 8, 2011
    Date of Patent: August 26, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Daisuke Karube, Yuzo Komatsu, Atsushi Suzuki
  • Publication number: 20080233043
    Abstract: A process for preparing chlorine by gas-phase oxidation of hydrogen chloride by means of a gas stream comprising molecular oxygen in the presence of a fixed-bed catalyst, wherein the process is carried out in a reactor (1) having heat-exchange plates (2) which are arranged in the longitudinal direction of the reactor (1) and have a spacing between them and through which a heat transfer medium flows, inlet and outlet facilities (3, 4) for the heat transfer medium to the heat-exchange plates (2) and also gaps (5) between the heat-exchange plates (2) in which the fixed-bed catalyst is present and into which the hydrogen chloride and the gas stream comprising molecular oxygen are passed, is described.
    Type: Application
    Filed: December 23, 2004
    Publication date: September 25, 2008
    Applicant: BASF Akiengesellschaft
    Inventors: Gerhard Olbert, Olga Schubert, Martin Sesing, Eckhard Stroefer, Martin Fiene
  • Patent number: 7217849
    Abstract: A method is described for producing n-propyl bromide of a high degree of purity, which contains isopropyl bromide in an amount lower than 0.1% w/w, and usually lower than 0.05%. The method is characterized in that n-propanol is reacted with HBr which is in gas form, preferably dry, and which is in excess over the stoichiometric amount, wherein the excess HBr is at the end of the reaction in an aqueous solution formed from the reaction water. The invention further relates to N-propyl bromide of high purity, containing typically less than 500 ppm of isopropyl bromide.
    Type: Grant
    Filed: November 11, 2002
    Date of Patent: May 15, 2007
    Assignee: Bromine Compounds Ltd.
    Inventors: Aharon Meirom, Arieh Kampf, Dmitri Grinberg, Sarina Grinberg, legal representative, Mark Grinberg, deceased
  • Patent number: 6984763
    Abstract: An oxidative halogenation and optional dehydrogenation process involving contacting a reactant hydrocarbon having three or more carbon atoms, such as propane or propene, or a halogenated derivative thereof, with a source of halogen, and optionally, a source of oxygen in the presence of a rare earth halide or rare earth oxyhalide catalyst, so as to form a halogenated hydrocarbon product, such as allyl chloride, having three or more carbon atoms and having a greater number of halogen substituents as compared with the reactant hydrocarbon, and optionally, an olefinic co-product, such as propene. The less desired of the two products, that is, the halogenated hydrocarbon or the olefin as the case may be, can be recycled to the process to maximize the production of the desired product.
    Type: Grant
    Filed: April 23, 2002
    Date of Patent: January 10, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Albert E. Schweizer, Mark E. Jones, Daniel A. Hickman
  • Patent number: 6977316
    Abstract: A catalytic one-step process for the production of CF3I by reacting, preferably in the presence of a source of oxygen, a source of iodine with a reactant of the formula: CF3R where R is —SH, —S—S—CF3, —S-phenyl, or —S—Si—(CH3)3. The catalyst may be a metal salt such as salts of Cu, Hg, Pt, Pd, Co, Mn, Rh, Ni, V, TI, Ba, Cs, Ca, K and Ge and mixtures thereof, preferably on a support such as MgO, BaO and CaO, BaCO3, CsNO3, Ba (NO3)2, activated carbon, basic alumina, and ZrO2.
    Type: Grant
    Filed: December 8, 2004
    Date of Patent: December 20, 2005
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, HsuehSung Tung
  • Patent number: 5986152
    Abstract: A supported catalyst includes: a) 0.5-15 wt. % of one or more Cu-II compounds, the quantitative amounts referring to copper metal; b) 0.1-8 wt. % of one or more alkali metal compounds, the quantitative amounts referring to alkali metal; c) 0.1-10 wt. % of an oxide mixture including; c1) 80-95 mole % of oxides of cerite rare earths with atomic Nos. 57 to 62, except promethium, and c2) 5-20 mole % of zirconium dioxide, where c1) and c2) must together total 100 mole % and the quantitative amount of c) refers to the oxides of the mixture, and d) the remainder up to 100 wt. % being .gamma. and/or .alpha.-aluminum oxide as support material, wherein e) the support material d) has a total pore volume in the range from 0.65 to 1.2 cm.sup.3 /g, and wherein f) the supported catalyst is present in the form of cylindrical hollow bodies having at least one passage channel, the ratio of height h to external diameter d.sup.e being less than 1.5 for diameters d.sub.e of up to 6 mm, and the ratio h/d.sub.e being less than 0.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: November 16, 1999
    Assignee: Degussa-Huls AG
    Inventors: Herbert Muller, Stefan Bosing, Ludwig Schmidhammer, Albin Frank, Klaus Haselwarter
  • Patent number: 5866731
    Abstract: In a process for producing a halogenated organic compound wherein a hydrogen halide is added to an organic compound having an aliphatic carbon-carbon unsaturated bond, a catalyst is used, which is an organic compound having at least two polar groups in the molecule each containing a heteroatom having an unshared electron pair, and having no aliphatic carbon-carbon unsaturated bond. A typical example of the catalyst is a polyoxyalkylene glycol or a polyol having at least 3 hydroxyl groups.
    Type: Grant
    Filed: May 5, 1997
    Date of Patent: February 2, 1999
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Kiyoshi Watanabe, Tomoo Matsuura
  • Patent number: 5866732
    Abstract: Alkyl bromides are prepared from mixtures comprising aqueous hydrobromic acid and olefins in a process in which there is concentration of the aqueous hydrobromic acid present during the reaction.
    Type: Grant
    Filed: August 22, 1997
    Date of Patent: February 2, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Eiermann, Klaus Ebel
  • Patent number: 5770780
    Abstract: In the preparation of alkyl halides from cycloaliphatic olefins and hydrohalic acids, the reaction is carried out at a temperature below the boiling point of the olefin without the addition of catalyst and without a solvent. At a high olefin conversion rate, alkyl halides are obtained with high selectivity and with very good color quality.
    Type: Grant
    Filed: February 10, 1997
    Date of Patent: June 23, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Josef Metz, Clemens Osterholt
  • Patent number: 5744663
    Abstract: It has been found that cyclopentene and hydrogen bromide can be continuously reacted in a simple manner to give cyclopentyl bromide in good yields and good selectivities if the reaction is carried out in the presence of a heterogeneous catalyst. The reaction can be carried out continuously and unreacted cyclopentene and possibly other constituents can be recirculated to the reaction.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: April 28, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Landscheidt, Alexander Klausener, Matthias Stenger, Paul Wagner
  • Patent number: 5672788
    Abstract: A process is disclosed for producing 1,1-difluoroethane (CH.sub.3 CHF.sub.2 or HFC-152a) in a two-step reaction in a manner that reduces formation of high boiling materials. The first step comprises adding at least one of HCl or HF to chloroethene (CH.sub.2 .dbd.CHCl) in order to obtain at least one of 1,1-dichloroethane (CH.sub.3 CHF.sub.2) or 1-chloro-1-fluoroethane (CH.sub.3 CHClF). The second step comprises converting 1,1-dichloroethane or 1-chloro-1-fluoroethane to 1,1-difluoroethane.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 30, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Klaus Guenter Wuttke
  • Patent number: 5527975
    Abstract: Bromochloro-alkanes are made by reaction of a corresponding chloroalkene with hydrogen bromide by a continuous process carried at -20.degree. to +20.degree. C., preferably in a gas-lift reactor.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: June 18, 1996
    Assignee: Albemarle Corporation
    Inventors: Dominique Cosserat, Francois Stutz
  • Patent number: 5466837
    Abstract: An ethylene stream which contains ethane as an impurity or a propylene stream which contains propane as an impurity is subjected to adsorption at a temperature of 50.degree. to 200.degree. C. in a bed of adsorbent which selectively adsorbs ethylene or propylene, thereby adsorbing substantially all of the ethylene or propylene. The purified ethylene or propylene stream is then subjected to partial oxidation in the presence of oxygen and, optionally ammonia to produce various partial oxidation products. The process is operated on a low per pass conversion with recycle of unreacted ethylene or propylene. In the system of the invention the adsorption unit may be upstream or downstream of the partial oxidation reactor.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: November 14, 1995
    Assignee: The BOC Group, Inc.
    Inventors: Ramakrishnan Ramachandran, Loc H. Dao
  • Patent number: 5345018
    Abstract: The present invention relates to a method of synthesizing 1-chloro-1-iodoethane by reacting hydrogen iodide with vinyl chloride monomer in the presence of an iodine containing catalyst under certain specified conditions. The resulting product of the reaction is a high yield, high purity 1-chloro-1-iodoethane. This 1-chloro-1-iodoethane is useful as a chain transfer agent in the polymerization of vinyl chloride monomer in a process which mimics a pseudo-living radical polymerization.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: September 6, 1994
    Assignee: The Geon Company
    Inventors: Philip L. Bak, Gregory P. Bidinger, Ross J. Cozens, Paul R. Klich
  • Patent number: 5262547
    Abstract: Petrochemicals are produced by the vapor phase reaction of a hydrocarbon with substantially pure oxygen in the presence of a suitable catalyst. In the improved process, the principal product is removed, carbon monoxide, present in the reactor effluent as a byproduct, is oxidized to carbon dioxide and part of the gaseous effluent, comprised mainly of carbon dioxide and unreacted hydrocarbon, is recycled to the reactor. Removal of carbon monoxide from the recycle stream reduces the hazard of a fire or explosion in the reactor or associated equipment. The use of carbon dioxide as the principal diluent increases heat removal from the reactor, thereby increasing the production capacity of the reactor.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: November 16, 1993
    Assignee: The BOC Group, Inc.
    Inventors: Ramakrishnan Ramachandran, Arthur I. Shirley, Lien-Lung Sheu
  • Patent number: 5179215
    Abstract: An improved process is provided for the production of a petrochemical by the vapor phase reaction of a hydrocarbon with an oxygen-containing gas in the presence of a suitable catalyst to produce a flammable gaseous product stream comprising the desired petrochemical, unreacted hydrocarbon, oxygen, carbon monoxide and carbon dioxide. In the improved process, a cooled or liquefied inert gas is injected as a quench fluid into the gaseous product stream exiting the hydrocarbon oxidation reactor, thereby cooling the stream to a temperature below the autoignition temperature of the flammable components of the stream, the petrochemical is recovered from the gaseous product and unreacted hydrocarbon is removed from the gaseous product and recycled to the reactor.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: January 12, 1993
    Assignee: The BOC Group, Inc.
    Inventors: Ramakrishnan Ramachandran, Donald L. MacLean
  • Patent number: 4827060
    Abstract: A catalyst, such as FeCl.sub.3, useful in the production of chlorinated hydrocarbons such as 1,1-dichloroethane is removed from the effluent of a process reactor and recycled. Hydrochloric acid is removed from the process stream resulting in the catalyst present in the process stream in solution precipitating out of solution. Then it can be removed from the process stream by conventional separation techniques. Alternatively, the catalyst present in the process stream as a solid, without the removal of HCl, is separated from the liquid present by means of a cyclone and recycled. In both cases, the catalyst retains its catalytic activity.
    Type: Grant
    Filed: November 9, 1987
    Date of Patent: May 2, 1989
    Assignee: The Dow Chemical Company
    Inventors: Thomas E. Morris, Rae L. Spencer, Gerald A. Gimber
  • Patent number: 4451683
    Abstract: An oxychlorination catalyst contains a copper compound, magnesium oxide and aluminium oxide, and the copper compound is present as a distinct phase on a support in which at least part of the magnesium oxide is in combined form with alumina.
    Type: Grant
    Filed: January 8, 1982
    Date of Patent: May 29, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: Phineas Davies, James R. Jennings, Jack Wolstenholme
  • Patent number: 4388278
    Abstract: The invention is a process for the purification of hydrogen chloride formed during the thermal cracking of 1,2-dichloroethane, by hydrogenating the acetylene impurities with excess hydrogen, at pressures of from 8 to 20 bar absolute and at temperatures of from 120.degree. to 180.degree. C., using platinum or palladium supported catalysts, wherein, according to the invention, carrier materials having a specific surface area of not more than 5 m.sup.2 /g are used, the hydrogen excess used is a function of the acetylene content, the gas mixture, after reaching a temperature of approximately 70.degree. C., is permitted a dwell time of not more than 0.8 second before it enters the catalyst, and the temperature, pressure and volume flow rates are dependent on one another within narrow limits.The purified hydrogen chloride is used for oxychlorination.
    Type: Grant
    Filed: October 29, 1981
    Date of Patent: June 14, 1983
    Assignee: Wacker Chemie GmbH
    Inventors: Ludwig Schmidhammer, Gerhard Dummer, Rudolf Straszer
  • Patent number: 4324940
    Abstract: Processes are provided for conducting selective acid catalyzed reactions involving olefins. Said catalytic reactions comprise isomerization, alkylation, addition, oligomerization, polymerization, aromatization, cracking and hydrocracking. The useful catalysts of this invention are the acidic forms of a novel class of zeolites characterized by a silica to alumina mole ratio of at least 12 and a constraint index in the approximate range of greater than about 2 to about 12. By utilization of such zeolites, smaller olefins are preferentially reacted when in mixed streams with larger olefins. Further of the such smaller olefins, linear olefins are preferentially reacted when in mixed streams with non-linear olefins and lesser branched olefins are preferentially reacted when in mixed streams with more highly branched olefins.
    Type: Grant
    Filed: April 9, 1980
    Date of Patent: April 13, 1982
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau