Preparing By Increasing The Number Of Carbons In The Compound Patents (Class 570/257)
  • Patent number: 11731925
    Abstract: Disclosed herein is a process comprising contacting a haloalkane reactant with an olefin in the presence of a catalyst system that consists of metallic iron and a phosphine to produce a haloalkane insertion product, wherein said haloalkane reactant is an alkane substituted with at least one halogen selected from the group consisting of F, Cl, and combinations thereof. Also disclosed herein is a process comprising contacting CF3CCl3 with CH2?CHX in the presence of a catalyst system that consists of metallic iron and a phosphine to make CF3CCl2CH2CHClX, wherein X?F or Cl. Also disclosed are further reactions in a sequence to produce HFO-1336ze and HCFO-1335zd. Also disclosed herein is a new composition comprising the compound CF3CF2CH?CHCl.
    Type: Grant
    Filed: July 24, 2017
    Date of Patent: August 22, 2023
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Sheng Peng, Mario Joseph Nappa, Andrew Jackson, Robert D. Lousenberg
  • Patent number: 10207969
    Abstract: The invention first relates to a composition comprising at least 99 wt. % of 1,1,1,3,3-pentachloropropane and at least one compound selected from a list of additional compounds consisting of dichloropropanes, trichloropropanes, tetrachloropropanes, pentachloropropanes different from 1,1,1,3,3-pentachloropropane, hexachloropropanes, heptachloropropanes, chloropropenes, dichloropropenes, trichloropropenes, tetrachloropropenes, pentachloropropenes and hexachloropropene, the weight content of said compound in the composition being lower than or equal to 500 ppm.
    Type: Grant
    Filed: October 7, 2015
    Date of Patent: February 19, 2019
    Assignee: ARKEMA FRANCE
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger, Bertrand Collier
  • Patent number: 9738577
    Abstract: A process for the manufacture of haloalkanes, or more particularly to a process for the manufacture of 1,1,1,3,3-pentachloropropane (HCC-240fa) and/or 1,1,1,3-tetrachloropropane (HCC-250fb). The process includes (a) mixing a catalyst, co-catalyst and a haloalkane starting material under conditions suitable to produce a homogeneous mixture; (b) reacting the homogeneous mixture with a haloalkene and/or alkene starting material under conditions suitable to produce a haloalkane product stream; and (c) recovering a haloalkane product from said product stream.
    Type: Grant
    Filed: October 9, 2007
    Date of Patent: August 22, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Hsueh Sung Tung, Ian Shankland
  • Patent number: 9512049
    Abstract: Processes for the production of alkenes are provided. The processes make use of methane as a low cost starting material.
    Type: Grant
    Filed: December 21, 2012
    Date of Patent: December 6, 2016
    Assignee: Dow Global Technologies LLC
    Inventors: Max Markus Tirtowidjojo, Brien A. Stears, William J. Kruper, Jr., Kurt F. Hirsekorn, Debashis Chakraborty
  • Patent number: 9090531
    Abstract: This invention is directed to a method for mitigating HCl generation during 1230xa purification, which comprises the steps of; (a) adding a chelating agent into 1230xa crude, and (b) conducting the 1230xa purification in the presence of said chelating agent at a quantity sufficient to reduce or prevent 1230xa decomposition. Examples of chelating agent include tributyl phosphate (TBP), tripropyl phosphate (TPP), and triethyl phosphate (TEP). The concentration of chelating agent in 1230xa crude can range from 0.001 to 20 wt %, preferably from 0.01 to 10 wt %, and more preferably from 0.1 to 5 wt %.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: July 28, 2015
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Huseh Sung Tung, Selma Bektesevic
  • Patent number: 9067858
    Abstract: Processes for isolating 1,1,1,2,3-pentachloropropane from a crude product stream containing the 1,1,1,2,3-pentachloropropane and ferric chloride. The processes may include deep distillation of the crude, treatment of the crude with a reagent that deactivates the ferric chloride followed by distillation on the deactivated crude stream, aqueous washing of the crude product stream to remove ferric chloride followed by distillation on the deactivated crude stream. Other embodiments simultaneously prepare 1,1,2,3-tetrachloroprene and 1,1,1,2,3-pentachloroprane.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: June 30, 2015
    Assignee: Occidental Chemical Corporation
    Inventors: John Lee Dawkins, Darrell Gene Hollis, Rodney L. Klausmeyer, Keith S. Kramer, Michael Andrew Garmon
  • Publication number: 20150023861
    Abstract: A method of forming chloro-substituted silanes from the reaction of an alkoxysilane with a chlorinating agent in the optional presence of a catalyst is provided. More specifically, chloro-substituted silanes, including but not limited to silicon tetrachloride, are formed by reacting a chlorinating agent, such as thionyl chloride, with an alkylalkoxysilane having the formula (R?O)4-xSiRx, where R and R? are independently selected alkyl groups comprising one or more carbon atoms and x is 0, 1, 2, or 3. The catalyst may be dimethylformamide, (chloromethylene)dimethyliminium chloride, or triethylamine, among others. The chloro-substituted silane formed in the reaction along with several by-products has the formula (R?O)4-x-ySiRxCly; where x is 0, 1, 2, or 3 and y is 1, 2, 3, or 4. One of the by-products of the reaction is an alkyl chloride.
    Type: Application
    Filed: March 16, 2012
    Publication date: January 22, 2015
    Applicants: DOW CORNING CORPORATION, CASE WESTERN RESERVE UNIVERSITY
    Inventors: Dimitris E Katsoulis, Malcolm E Kenney, Plousia E Vassilaras
  • Patent number: 8889927
    Abstract: This invention relates to a method to improve 1,1,3-trichloropropene (HCC-1240za) and/or 3,3,3-trichloropropene (HCC-1240zf) selectivity in the dehydrochlorination of 1,1,1,3-tetrachloropropane (HCC-250fb). In normal practice, FeCl3 is used as the catalyst for the dehydrochlorination of HCC-250fb to produce 1,1,3-trichloropropene and/or 3,3,3-trichloropropene. Here the improvement comprises, using as the starting material, a mixture comprising HCC-250fb and Heavies generated from the reaction of CCl4 and ethylene to produce HCC-250fb, wherein the Heavies comprise one or more tetrachloropentane isomers. These compounds reduce or eliminate the formation of unwanted high boiling compounds (HBCs).
    Type: Grant
    Filed: March 12, 2013
    Date of Patent: November 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Terris Yang, Joshua Close, Hsueh Sung Tung
  • Publication number: 20140275656
    Abstract: Provided are (Z,Z,E)-1-chloro-6,10,12-pentadecatriene that can be synthesized without an oxidation reaction and a method for preparing (Z,Z,E)-7,11,13-hexadecatienal by using (Z,Z,E)-1-chloro-6,10,12-pentadecatriene while not using an oxidation reaction. More specifically, provided is a method for preparing (Z,Z,E)-7,11,13-hexadecatrienal including a step of reacting a Grignard reagent into which (Z,Z,E)-1-chloro-6,10,12-pentadecatriene is converted with ethyl orthoformate to obtain (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene, and a step of treating the (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene with an acid to obtain (Z,Z,E)-7,11,13-hexadecatrienal.
    Type: Application
    Filed: February 25, 2014
    Publication date: September 18, 2014
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuki Miyake, Miyoshi Yamashita, Takehiko Fukumoto, Naoki Ishibashi
  • Patent number: 8835702
    Abstract: Disclosed is a process for the manufacture of haloalkane compounds, and more particularly, an improved process for the manufacture of the compound 1,1,1,3,3-penta-chloropropane (HCC-240fa), which mitigates the formation of by-products from vinyl chloride (CH2?CHCl). The present invention is also useful in the manufacture of other haloalkane compounds such as HCC-250 and HCC-360. One embodiment of the invention comprises a method for mitigating 1,1,3,3,5,5-hexachloropentane and 1,1,1,3,5,5-hexachloropentane formation in the HCC-240fa manufacturing process, in which FeCl3, is introduced to a reactor only after the start-up phase has ended and a continuous operation has started. In a preferred embodiment, “pre-chelated” FeCl3, which is concentrated in a catalyst recovery column, is introduced to reactor after the continuous operation has started.
    Type: Grant
    Filed: May 25, 2012
    Date of Patent: September 16, 2014
    Assignee: Honeywell International Inc.
    Inventors: Joshua Close, Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8722946
    Abstract: Disclosed is a process for the manufacture of haloalkane compounds, and more particularly, to an improved process for the manufacture of the compound 1,1,1,3,3-pentachloropropane (HCC-240fa), which mitigates the formation of by-products. The present invention is also useful in the manufacture of other haloalkane compounds such as HCC-250 and HCC-360. One embodiment of the process comprises a method and system for avoiding the formation of polyvinyl chloride during the production of HCC-240fa from CCl4, in which vinyl chloride (VCM) is fed into a reactor as a vapor instead of as a liquid, using a diffusing device to further increase the contact surface between VCM vapor and CCl4.
    Type: Grant
    Filed: May 25, 2012
    Date of Patent: May 13, 2014
    Assignee: Honeywell International Inc.
    Inventors: Joshua Close, Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8664424
    Abstract: Provided is a method for preparing 2,5-dimethylphenylacetic acid, wherein p-xylene is mixed with paraformaldehyde and concentrated hydrochloric acid in a solvent of ion liquid to obtain 2,5-dimethyl benzyl chloride by the chloromethylation reaction. Then, 2,5-dimethyl benzyl chloride is introduced into a reactor with an acid binding agent and a solvent, the carbonylation and hydrolysis reaction is conducted in the presence of a catalyst to obtain 2,5-dimethylphenylacetic acid. The present process has new route, less synthesis steps, simple operation, lower cost, increased yield, and is friendly to the environment. Therefore, the method is suitable for industrial production.
    Type: Grant
    Filed: June 7, 2011
    Date of Patent: March 4, 2014
    Assignees: Lianhe Chemical Technology Co., Ltd, Jiangsu Lianhe Chemical Technology Co., Ltd.
    Inventors: Ping Wang, Xiaobin Fan, Xingjun Lin, Zhaohui He
  • Publication number: 20140011973
    Abstract: The invention discloses a compound having branching alkyl chains, the method for preparing the same and use thereof in photoelectric devices. By applying the branching alkyl chains as the solubilizing group to the preparation of organic conjugated molecules (for example, organic conjugated polymers), the number of methylenes between the resultant alky side chains and the backbone, i.e., m>1, which can effectively reduce the effect of the alkyl chains on the backbone ?-? stacking, thereby ensuring the solubility of the organic conjugated molecule while greatly increasing the mobility of their carriers. It is suitable for an organic semiconductor material in photoelectric devices such as organic solar cells, organic light emitting diodes and organic field effect transistors, etc.
    Type: Application
    Filed: July 5, 2013
    Publication date: January 9, 2014
    Inventors: Jian PEI, Ting LEI, Jinhu DOU
  • Patent number: 8350099
    Abstract: Disclosed are fluorovinyl ether functionalized aromatic diesters and derivatives thereof. The compounds disclosed have utility as functionalized monomers and comonomers in polyesters, polyamides, and the like. It has been found that incorporation of the monomers into polymers provides improved soil resistance to shaped articles produced from the polymers.
    Type: Grant
    Filed: September 1, 2010
    Date of Patent: January 8, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Neville Everton Drysdale, Surbhi Mahajan, Kenneth Gene Moloy, Fredrik Nederberg, Joel M. Pollino, Joachim C. Ritter
  • Patent number: 8304589
    Abstract: A process of making a chlorinated hydrocarbon through a thermal dehydrochlorination step in which an unsaturated compound represented by the following general formula (2) is obtained by thermally decomposing a saturated compound represented by the following general formula (1). CCl3—CCl2-mHm—CCl3-nHn??(1) CCl2?CCl2-mHm-1—CCl3-nHn??(2) (in the above formulas, m is 1 or 2, and n is an integer of 0 to 3.).
    Type: Grant
    Filed: February 27, 2012
    Date of Patent: November 6, 2012
    Assignee: Tokuyama Corporation
    Inventors: Tadahiro Fukuju, Kikuo Yamamoto, Masayuki Moriwaki, Yasutaka Komatsu, Akihiro Saito, Shunsuke Hosaka, Dai Tsunoda, Jun Kawakami
  • Publication number: 20120157723
    Abstract: A process of making a chlorinated hydrocarbon through a thermal dehydrochlorination step in which an unsaturated compound represented by the following general formula (2) is obtained by thermally decomposing a saturated compound represented by the following general formula (1). CCl3—CCl2-mHm—CCl3-nHn??(1) CCl2?CCl2-mHm-1—CCl3-nHn??(2) (in the above formulas, m is 1 or 2, and n is an integer of 0 to 3.
    Type: Application
    Filed: February 27, 2012
    Publication date: June 21, 2012
    Inventors: Tadahiro FUKUJU, Kikuo YAMAMOTO, Masayuki MORIWAKI, Yasutaka KOMATSU, Akihiro SAITO, Shunsuke HOSAKA, Dai TSUNODA, Jun KAWAKAMI
  • Patent number: 8115038
    Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride ethylene, and chlorine.
    Type: Grant
    Filed: December 17, 2008
    Date of Patent: February 14, 2012
    Assignee: Occidental Chemical Corporation
    Inventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
  • Patent number: 7947856
    Abstract: A telomerisation process is described whereby haloalkanes like tetrachloromethane are added to halogenated olefins like 2-chloroprop-1-ene in the presence of an iron catalyst and a phosphite. The reaction products, e.g. 1,1,1,3,3-pentachlorobutane, can be fluorinated.
    Type: Grant
    Filed: October 5, 2007
    Date of Patent: May 24, 2011
    Assignee: SOLVAY (Societe Anonyme)
    Inventors: Veronique Mathieu, Francine Janssens
  • Publication number: 20110105810
    Abstract: A process for the insertion of a fluorinated olefin into a fluorinated iodide in the presence of a nickel catalyst at a temperature of a maximum of 150° C. with an initial rate of 0.04 mole/hour without loss of selectivity is disclosed.
    Type: Application
    Filed: November 4, 2009
    Publication date: May 5, 2011
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Sheng Peng, Kenneth Gene Moloy
  • Patent number: 7872161
    Abstract: A process is disclosed for making CF3CF?CH2 The process involves (i) contacting CHCl2CF2CF3 in a reaction zone in the presence of a catalytically effective amount of a dehydrofluorination catalyst to produce CCl2?CFCF3; (ii) contacting CCl2?CFCF3 with H2 formed in (i) in a reaction zone in the presence of a catalyst comprising a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina fluorided alumina, aluminum fluoride and mixtures thereof, to produce a product mixture comprising CF3CF?CH2, wherein the mole ratio of H2 to CCl2?CFCF3 fed to the reaction zone is between about 1:1 and about 4:1 and (iii) recovering CF3CF?CH2 from the product mixture formed in (ii).
    Type: Grant
    Filed: November 15, 2007
    Date of Patent: January 18, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20090247794
    Abstract: A telomerisation process is described whereby haloalkanes like tetrachloromethane are added to halogenated olefins like 2-chloroprop-1-ene in the presence of an iron catalyst and a phosphite. The reaction products, e.g. 1,1,1,3,3-pentachlorobutane, can be fluorinated.
    Type: Application
    Filed: October 5, 2007
    Publication date: October 1, 2009
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventors: Veronique Mathieu, Francine Janssens
  • Publication number: 20080091053
    Abstract: A process for the manufacture of haloalkanes, or more particularly to a process for the manufacture of 1,1,1,3,3-pentachloropropane (HCC-240fa) and/or and/or 1,1,1,3-tetrachloropropane (HCC-250fb). The process includes (a) mixing a catalyst, co-catalyst and a haloalkane starting material under conditions suitable to produce a homogeneous mixture; (b) reacting the homogeneous mixture with a haloalkene and/or alkene starting material under conditions suitable to produce a haloalkane product stream; and (c) recovering a haloalkane product from said product stream.
    Type: Application
    Filed: October 9, 2007
    Publication date: April 17, 2008
    Inventors: Hsueh Sung Tung, Ian Shankland
  • Patent number: 7102042
    Abstract: A method for preparing a composition of the formula in a yield greater than 50% where R1 is C 1-20 comprising the steps of combining fluorene or dibromo flourene, an excess of alkali metal hydroxide and a halogenated alkyl in the presence of a phase transfer catalyst but in the absence of a polar aprotic solvent; heating the combination; and separating the dialkylated fluorene or dialylated dibromo fluorene. If the flourene is not brominated prior to alkylation, the dialkylated fluorene is then brominated.
    Type: Grant
    Filed: December 19, 2002
    Date of Patent: September 5, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Timothy J. Adaway, Michael A. Gonzalez, Weishi Wu
  • Patent number: 7094936
    Abstract: Methods and materials are provided for the production and purification of halogenated compounds and intermediates in the production of 1,1,1,3,3-pentafluoropropane. In a preferred embodiment, the process steps include: (1) reacting carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane; (2) dehydrochlorinating the 1,1,1,3,3-pentachloropropane with a Lewis acid catalyst to produce 1,1,3,3-tetrachloropropene; (3) fluorinating the 1,1,3,3-tetrachloropropene to produce 1-chloro-3,3,3-trifluoropropene; (4) fluorinating the 1-chloro-3,3,3-trifluoropropene to produce a product mixture containing 1,1,1,3,3-pentafluoropropane; and (5) separating 1,1,1,3,3-pentafluoropropane from by-products.
    Type: Grant
    Filed: October 16, 2003
    Date of Patent: August 22, 2006
    Assignee: Great Lakes Chemical Corporation
    Inventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
  • Patent number: 6861566
    Abstract: There is provided an industrially advantageous process for producing a 1-chloro-4-arylbutane represented by the general formula (2): wherein R represents hydrogen, lower alkyl, or lower alkoxy, characterized by reacting 1-bromo-3-chloropropane with a compound represented by the general formula (1): wherein R is as defined above; and X represents chlorine, bromine, or iodine, in a solvent.
    Type: Grant
    Filed: March 11, 2002
    Date of Patent: March 1, 2005
    Assignees: Sumitomo Chemical Company, Limited, Ono Pharmaceutical Co., Ltd.
    Inventors: Hiroaki Hibino, Susumu Ohtsuka, Yasunobu Miyamoto, Itsuo Okumoto
  • Patent number: 6858763
    Abstract: The present invention relates to a process for preparing an elastomeric ethylene-hexafluoropropylene copolymer with excellent vulcanization properties, which comprises emulsion polymerizing ethylene, hexafluoropropylene and when in demand, a monomer copolymerizable therewith in a aqueous medium at a low temperature of ?20° C. to 40° C. using a radical polymerization initiator.
    Type: Grant
    Filed: September 19, 2001
    Date of Patent: February 22, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Mitsuo Tsukamoto, Masao Otsuka, Mitsuhiro Otani, Tatsuya Morikawa, Hideya Saito
  • Patent number: 6806396
    Abstract: The present invention relates to the co-pyrolysis of fluoroform and chlorodifluoromethane to form a mixture of useful fluoroolefin and saturated HFCs, notably, tetrafluoroethylene and hexafluoropropylene and CF3CHF2 and CF3CHFCF3, respectively.
    Type: Grant
    Filed: December 16, 2002
    Date of Patent: October 19, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Peter Gideon Gelblum, Velliyur Nott Mallikarjuna Rao, Charles Joseph Noelke, Norman Herron
  • Publication number: 20040116755
    Abstract: A method for the synthesis of cyclobuta aromatic compounds by cyclizing two ortho dibromoalkyl substituents is described. Using a mediator, such as nickel metal, and continuous removal of product from contact with the mediator, high product yields are achieved. A method for bromination of ortho alkyl substituents of aromatic compounds is also described.
    Type: Application
    Filed: September 22, 2003
    Publication date: June 17, 2004
    Inventor: Amnon Stanger
  • Patent number: 6720466
    Abstract: A process for economically producing 1,1,1,3,3-pentachloropropane under conditions which preserve the activity of the catalyst. In a preferred embodiment, a two-stage distillation process is employed. In the two-stage process, the size of the equipment, temperature and vacuum are varied.
    Type: Grant
    Filed: April 17, 2002
    Date of Patent: April 13, 2004
    Assignee: Vulcan Chemicals Division of Vulcan Materials Company
    Inventors: Richard L. Wilson, John L. Dawkins, Rodney L. Klausmeyer, James J. Weller
  • Publication number: 20030028057
    Abstract: Methods and materials are provided for the production and purification of halogenated compounds and intermediates in the production of 1,1,1,3,3-pentafluoropropane. In a preferred embodiment, the process steps include: (1) reacting carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane; (2) dehydrochlorinating the 1,1,1,3,3-pentachloropropane with a Lewis acid catalyst to produce 1,1,3,3-tetrachloropropene; (3) fluorinating the 1,1,3,3-tetrachloropropene to produce 1-chloro-3,3,3-trifluoropropene; (4) fluorinating the 1-chloro-3,3,3-trifluoropropene to produce a product mixture containing 1,1,1,3,3-pentafluoropropane; and (5) separating 1,1,1,3,3-pentafluoropropane from by-products.
    Type: Application
    Filed: April 26, 2002
    Publication date: February 6, 2003
    Inventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
  • Publication number: 20030009066
    Abstract: A process is provided by which addition of water is used to enhance the production of any hydrochlorocarbon feedstock through the use of Kharasch chemistry, i.e. the combination of a polychlorinated alkane with an olefin to produce a chlorinated or hydrochlorinated alkane with the use of a transition metal compound in homogeneous solution as catalyst. Preferably, water is added to increase the production of 1,1,1,3,3-pentachloropropane by the reaction of carbon tetrachloride and vinyl chloride in the presence of a catalyst mixture of organo phosphate solvent, iron metal and ferric chloride.
    Type: Application
    Filed: June 14, 2001
    Publication date: January 9, 2003
    Inventor: Lloyd B. Branam
  • Patent number: 6500993
    Abstract: Process for preparing halogenated hydrocarbons, comprising at least 3 carbon atoms, by catalytic telomerization between a haloalkane and an olefin in the presence of an amine with a high boiling point as co-catalyst. 1,1,1,3,3-Pentachloropropane and 1,1,1,3,3-pentachlorobutane are thus prepared under mild conditions in good yield and the catalyst/co-catalyst system can be easily separated by distillation and recycled.
    Type: Grant
    Filed: November 3, 1999
    Date of Patent: December 31, 2002
    Assignee: Solvay (Societe Anonyme)
    Inventors: Véronique Mathieu, Jean-Paul Schoebrechts
  • Patent number: 6500995
    Abstract: A process is provided by which addition of water is used to enhance the production of any hydrochlorocarbon feedstock through the use of Kharasch chemistry, i.e. the combination of a polychlorinated alkane with an olefin to produce a chlorinated or hydrochlorinated alkane with the use of a transition metal compound in homogeneous solution as catalyst. Preferably, water is added to increase the production of 1,1,1,3,3-pentachloropropane by the reaction of carbon tetrachloride and vinyl chloride in the presence of a catalyst mixture of organo phosphate solvent, iron metal and ferric chloride.
    Type: Grant
    Filed: June 14, 2001
    Date of Patent: December 31, 2002
    Assignee: Vulcan Chemicals
    Inventor: Lloyd B. Branam
  • 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: 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: 6313360
    Abstract: A process is provided for the production of 1,1,1,3,3-pentachloropropane. The process comprises: (a) producing a product mixture in a reactor by reacting carbon tetrachloride and vinyl chloride in the presence of a catalyst mixture comprising organophosphate solvent, iron metal and ferric chloride under conditions sufficient to produce 1,1,1,3,3-pentachloropropane; (b) subjecting the 1,1,1,3,3-pentachloropropane containing product mixture from step (a) to evaporation such that a fraction enriched in 1,1,1,3,3-pentachloropropane is separated from the product mixture and a bottoms fraction results which comprises the iron metal/ferric chloride catalyst components and heavy end by-products; and (c) recycling at least a portion of the bottoms fraction from step (b) to the reactor.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: November 6, 2001
    Assignee: Vulcan Materials Company
    Inventors: Richard Wilson, Rodney Klausmeyer, Lloyd Branam, Derrek Burrows, Jim Strathe, John Dawkins, Theo Lichtenstein, Joseph Weller, John Tummons
  • 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: 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: 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: 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: 5792893
    Abstract: A novel method for manufacturing 1,1,1,3,3,3-hexachloropropane. Tetrachloromethane is reacted with 1,1-dichloroethene in the presence of a catalyst comprising copper and a solvent selected from a C3 to a C5 alkanenitrile. The 1,1,1,3,3,3-hexachloropropane can be separated from the reaction by-products, unconsumed reactants and catalyst and solvent, which components can be recovered and recycled back to the reactor.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: August 11, 1998
    Assignee: Vulcan Materials Company
    Inventors: Richard Leroy Wilson, Charles Richard Cupit, Rodney Lee Klausmeyer
  • Patent number: 5633413
    Abstract: A process for the continuous production of telomers CCl.sub.3 (CH.sub.2 CCl.sub.2).sub.n Cl where n=1-3 (Formula I) by the continuous reaction of CCl.sub.4 and vinylidene chloride in the presence of a solvent and a catalyst. The reaction to form CCl.sub.3 (CH.sub.2 CCl.sub.2)Cl proceeds at a reaction rate constant k.sub.1. If n=1, CCl.sub.3 (CH.sub.2 CCl.sub.2)Cl is continuously removed from the reactor. If n=2, the removed CCl.sub.3 (CH.sub.2 CCl.sub.2)Cl reacts similarly with CCl.sub.4 and CH.sub.2 .dbd.CCl.sub.2 in a second reactor to form and remove CCl.sub.3 (CH.sub.2 CCl.sub.2).sub.2 Cl under conditions to have a reaction rate constant k.sub.2, wherein the ratio of the molar amounts of CCl.sub.4 to CCl.sub.3 (CH.sub.2 CCl.sub.2)Cl reacted is greater than the ratio k.sub.2 /k.sub.1. If n=3, the removed CCl.sub.3 (CH.sub.2 CCl.sub.2).sub.2 Cl similarly reacts in a third reactor with CCl.sub.4 and CH.sub.2 .dbd.CCl.sub.2 to form CCl.sub.3 (CH.sub.2 CCl.sub.2).sub.
    Type: Grant
    Filed: August 8, 1995
    Date of Patent: May 27, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Timothy R. Demmin, David E. Bradley
  • Patent number: 5426252
    Abstract: Chloromethane compounds including carbon tetrachloride and the chlorofluoromethane compounds, such as dichlorodifluoromethane, can be catalytically hydrodechlorinated, e.g., in the case of dichlorodifluoromethane to monochlorodifluoromethane and/or difluoromethane, by treatment with hydrogen in the presence of a transition metal carbide catalyst, for example, a Group IVB metal carbide, such as tungsten carbide, supported on an oxidic support, such as alumina, optionally with a passivating layer of ceramic, such as silicon carbide, between the oxidic support and catalyst. The catalyst preferably has a surface area of no less than about 1 m.sup.2 /gm.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: June 20, 1995
    Assignee: Akzo Nobel NV
    Inventor: Fawzy G. Sherif
  • Patent number: 5352812
    Abstract: The metathesis of functionalized and unfunctionalized acyclic olefins using catalyst compositions containing iridium and silver in a molar ration of 3 to 1.
    Type: Grant
    Filed: July 8, 1993
    Date of Patent: October 4, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Jerald Feldman, Marcia B. France
  • Patent number: 5334782
    Abstract: The present invention relates to a method for producing a hydrogen-containing chloromethane such as chloroform at high selectivity in good yield by reducing a polychloromethane such as carbon tetrachloride in the presence of a reduction catalyst.In the present invention, it is important to conduct the reduction reaction in a liquid phase, whereby formation of impurities such as polymers which deactivate the catalyst, can effectively be suppressed, and the high selectivity and high activity of the reduction catalyst can adequately be obtained.As the reduction catalyst, at least one member selected from elements of Groups 8, 9 and 10, such as ruthenium, rhodium, palladium and platinum, may suitably be employed. Also a catalyst comprising, as the main component, such an element and having at least one member of Group 11 elements such as copper, silver and gold added thereto, may also suitably be employed.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: August 2, 1994
    Assignee: AG Technology Co., Ltd.
    Inventors: Shinsuke Morikawa, Masaru Yoshitake, Shin Tatematsu
  • Patent number: 5138109
    Abstract: A halogenated alkyl of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each is a lower alkyl group, X is chlorine atom or a bromine atom and Y is a hydrogen atom or a halogen atom is prepared in high conversion and high selectivity by reacting a tertiary halogenated alkyl of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and X are the same as defined above with an ethylene derivative of the formula:CH.sub.2 .dbd.CH--Y (III)wherein Y is the same as defined above in the presence of a liquid catalyst comprising aluminum chloride and an alkylbenzene of the formula: ##STR3## wherein R.sub.4, R.sub.5 and R.sub.6 are the same or different and each is a lower alkyl group or a hydrogen atom provided that at least one of them is a lower alkyl group.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: August 11, 1992
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Michio Yamamoto, Masaru Ishino, Motoo Hazama, Shigefumi Tokumasu
  • Patent number: 5097081
    Abstract: The highly chlorinated methanes, e.g., carbon tetrachloride, are improvedly dechlorinated by reacting same with hydrogen in the presence of oxygen or an oxygen-containing gas, e.g., air, and a catalytically effective amount of a metal of the copper or precious metal Groups of the Periodic Table, typically in the form of a fixed or fluidized bed thereof, and advantageously in the gaseous phase.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: March 17, 1992
    Assignee: Atochem
    Inventors: Yves Correia, Joseph Nowocien