Catalyst Utilized Patents (Class 570/227)
  • Patent number: 11338276
    Abstract: A catalyst for preparing chloroethylene by cracking 1,2-dichloroethane and a preparation and regeneration method thereof are disclosed in the present application. A catalyst for preparing chloroethylene by cracking 1,2-dichloroethane includes a carrier and a nitrogen-containing carbon as an active component of the catalyst with the nitrogen-containing carbon being loaded on the carrier. The method for preparing the catalyst includes: supporting an organic matter on an inorganic porous carrier and then performing a carbonization-nitridation process by pyrolysis in an atmosphere containing the nitrogen-containing compound. The method for regenerating the catalyst includes: calcinating the catalyst with deactivated carbon deposit in an oxidizing atmosphere to remove all the carbonaceous portions on the surface, and repeating the above preparation process of the catalyst.
    Type: Grant
    Filed: April 30, 2019
    Date of Patent: May 24, 2022
    Assignees: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES, FORMOSA PLASTICS CORPORATION
    Inventors: Jinming Xu, Sisi Fan, Yanqiang Huang, Fao Zhang, Chin Lien Huang, Wan Tun Hung, Tu Cheng Chen, Chien Hui Wu, Ya Wen Cheng, Ming Hsien Wen, Chao Chin Chang, Tsao Cheng Huang
  • Patent number: 11247951
    Abstract: The present invention aims to provide an efficient method for obtaining a desired isomer of HFO-1132 from a composition comprising trans-1,2-difluoroethylene (HFO-1132(E)) and cis-1,2-difluoroethylene (HFO-1132(Z)). The present invention provides, as a means for solving the problem, a method for producing HFO-1132(E) and/or HFO-1132(Z), comprising steps (1) to (3): (1) supplying a composition comprising HFO-1132(E) and/or HFO-1132(Z) to a reactor filled with a catalyst to perform an isomerization reaction between the HFO-1132(E) and the HFO-1132(Z); (2) separating the reaction product obtained in step (1) into a first stream comprising the HFO-1132(E) as a main component, and a second stream comprising the HFO-1132(Z) as a main component; and (3) recycling the first stream or the second stream obtained in step (2) to the reactor, to subject the first stream or the second stream to the isomerization reaction.
    Type: Grant
    Filed: January 29, 2021
    Date of Patent: February 15, 2022
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Takashi Usui, Tsubasa Nakaue, Yuzo Komatsu, Kazuhiro Takahashi, Takehiro Chaki, Megumi Kushida
  • Patent number: 10851033
    Abstract: A process for producing a reaction mixture comprising a plurality of C3 chlorinated alkane isomers comprising chlorinating a C3 chlorinated alkane starting material in a chlorination zone to produce the plurality of C3 chlorinated alkane isomers, the plurality of C3 chlorinated alkane isomers each having at least one more chlorine atom than the C3 chlorinated alkane starting material, wherein the concentration of the C3 chlorinated alkane starting material is controlled such that conversion of the C3 chlorinated alkane starting material to the plurality of C3 chlorinated alkane isomers, represented by the molar ratio of the C3 chlorinated alkane starting material:C3 chlorinated alkane isomers in the reaction mixture present in the chlorination zone, does not exceed about 40:60.
    Type: Grant
    Filed: June 21, 2018
    Date of Patent: December 1, 2020
    Assignee: SPOLEK PRO CHEMICKOU A HUTNI VYROBU A.S.
    Inventors: Zdenek Ondrus, Pavel Kubicek, Petr Sladek
  • Patent number: 10807925
    Abstract: A process for making a fluorinated olefin having the step of dehydrochlorinating a hydrochlorofluorocarbon having at least one hydrogen atom and at least one chlorine atom on adjacent carbon atoms, preferably carried out in the presence of a catalyst selected from the group consisting of (i) one or more metal halides, (ii) one or more halogenated metal oxides, (iii) one or more zero-valent metals/metal alloys, (iv) a combination of two or more of the foregoing.
    Type: Grant
    Filed: May 26, 2015
    Date of Patent: October 20, 2020
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 10611707
    Abstract: Disclosed is a process for preparing a highly pure 1,1,1,2,3-pentachloropropane product, comprising 1-a) providing a reaction mixture comprising ethylene, carbon tetrachloride and a catalyst in a principal alkylation zone to produce 1,1,1,3-tetrachloropropane in the reaction mixture, and 1-b) treating the reaction mixture obtained in step 1-a) to obtain a 1,1,1,3-tetrachloropropane feedstock; 2-a) contacting the 1,1,1,3-tetrachloropropane feedstock with a catalyst in a dehydrochlorination zone to produce a reaction mixture comprising 1,1,1,3-tetrachloropropane and 1,1,3-trichloropropene, and 2-b) treating the reaction mixture obtained in step 2-a) to obtain a 1,1,3-trichloropropene feedstock; 3-a) contacting the 1,1,3-trichloropropene feedstock with chlorine in a reaction zone to produce a reaction mixture containing 1,1,1,2,3-pentachloropropane and 1,1,3-trichloropropene, the reaction zone being different from the dehydrochlorination zone, and 3-b) treating the reaction mixture obtained in step 3-a) to ob
    Type: Grant
    Filed: December 8, 2017
    Date of Patent: April 7, 2020
    Assignee: SPOLEK PRO CHEMICKOU A HUTNI VYROBU A.S.
    Inventors: Zdenek Ondrus, Pavel Kubicek, Karel Filas, Petr Sladek
  • Patent number: 10294179
    Abstract: Disclosed is a process for producing a chlorinated C3-6 alkane comprising providing a reaction mixture comprising an alkene and carbon tetrachloride in a principal alkylation zone to produce chlorinated C3-6 alkane in the reaction mixture, and extracting a portion of the reaction mixture from the principal alkylation zone, wherein: a) the concentration of the chlorinated C3-6 alkane in the reaction mixture in the principal alkylation zone is maintained at a level such that the molar ratio of chlorinated C3-6 alkane:carbon tetrachloride in the reaction mixture extracted from the alkylation zone does not exceed 95:5 when the principal alkylation zone is in continuous operation; and/or b) the reaction mixture extracted from the principal alkylation zone additionally comprises alkene and the reaction mixture is subjected to a dealkenation step in which at least about 50% or more by weight of the alkene present in the reaction mixture is extracted therefrom and at least about 50% of the extracted alkene is fed b
    Type: Grant
    Filed: December 29, 2017
    Date of Patent: May 21, 2019
    Assignee: SPOLEK PRO CHEMICKOU A HUTNI VYROBU A.S.
    Inventors: Karel Filas, Pavel Kubicek, Zdenek Ondrus, Petr Sladek
  • Patent number: 10189759
    Abstract: Disclosed is a process for preparing a chlorinated alkene, comprising contacting a chlorinated alkane with a catalyst in a dehydrochlorination zone to produce a liquid reaction mixture comprising the chlorinated alkane and the chlorinated alkene, and extracting chlorinated alkene from the reaction mixture, wherein the concentration of the chlorinated alkene in the reaction mixture present in the dehydrochlorination zone is controlled such that the molar ratio of chlorinated alkene:chlorinated alkane is from 1:99 to 50:50.
    Type: Grant
    Filed: March 30, 2017
    Date of Patent: January 29, 2019
    Assignee: SPOLEK PRO CHEMICKOU A HUNTI VYROBU A.S.
    Inventors: Zdenek Ondrus, Pavel Kubicek, Karel Filas, Petr Sladek
  • Patent number: 9969664
    Abstract: A process for the manufacture of 1,1,3,3-tetrachloropropene, the process comprising dehydrochlorinating 1,1,1,3,3-pentachloropropane.
    Type: Grant
    Filed: May 14, 2015
    Date of Patent: May 15, 2018
    Assignee: Occidental Chemical Corporation
    Inventors: Rodney L. Klausmeyer, Darrell G. Hollis, Keith S. Kramer, John L. Dawkins, Derrek Rae Burrows
  • Patent number: 9475740
    Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of 1,2-dichloropropane, a by-product in the production of chlorohydrin, as a low cost starting material. 1,1,1,2,2-pentachloropropane produced by the process is subjected to catalytic dehydrochlorination and build-up of the same within the process is avoided.
    Type: Grant
    Filed: December 17, 2013
    Date of Patent: October 25, 2016
    Assignee: BLUE CUBE IP LLC
    Inventors: Max M. Tirtowidjojo, David S. Laitar, Barry B. Fish, William J. Kruper, Jr.
  • Patent number: 9233896
    Abstract: Processes for the production of chlorinated propenes are provided wherein a dehydrochlorination reaction occurs prior to a first chlorination reaction. The present processes make use of at least one reactor twice, i.e., at least two reactions occur in the same reactor. Cost and time savings are thus provided. Additional savings can be achieved by conducting more than two chlorination reactions, or all chlorination reactions, in one chlorination reactor, and/or by conducting more than two dehydrochlorination reactions, or all dehydrochlorination reactions, within a single dehydrochlorination reactor.
    Type: Grant
    Filed: August 4, 2012
    Date of Patent: January 12, 2016
    Assignee: Blue Cube IP LLC
    Inventors: Max M. Tirtowidjojo, Barry B. Fish, David S. Laitar
  • Publication number: 20150126786
    Abstract: The invention provides a process for preparing a C3-7 (hydro)fluoroalkene comprising dehydrohalogenating a C3-7 hydro(halo)fluoroalkane in the presence of a catalyst comprising a metal oxide supported on alumina, wherein the catalyst has a sodium content of less than about 800 ppm.
    Type: Application
    Filed: May 1, 2013
    Publication date: May 7, 2015
    Inventors: Andrew P Sharratt, Claire E McGuinness, Sheryl C Carolan
  • Patent number: 9018428
    Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: April 28, 2015
    Assignee: Honeywell International Inc.
    Inventor: Stephen A. Cottrell
  • Patent number: 9012702
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCFClCH2X with a catalyst in a reaction zone to produce a product mixture comprising RfCF?CHX, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, X ?H, F, Cl, Br or I, M=K, Na or Cs, and Y?F, Cl or Br.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: April 21, 2015
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • 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: 8993816
    Abstract: Disclosed is a process for the synthesis of 1,1,2,3-tetrachloropropene (HCC-1230xa) using 1,1,3-trichloropropene (HCC-1240za) and/or 3,3,3-trichloropropene (HCC-1240zf) and Cl2 gas as the reactants, wherein the process takes place in a single reactor system. Before this invention, HCC-1230xa was made in a two-step process using HCC-1240za/HCC-1240zf and Cl2 gas, and the processing was conducted using two separate reactors.
    Type: Grant
    Filed: October 7, 2014
    Date of Patent: March 31, 2015
    Assignee: Honeywell International Inc.
    Inventors: Terris Yang, Hsueh Sung Tung
  • Patent number: 8921622
    Abstract: A process for the selective dehydrofluorination of hydrochlorofluoroalkanes and novel hydrochlorofluoroalkenes is described wherein an effective amount of a catalytically active metal compound is applied which is selected from the group consisting of AlF3??, MgAlxF2+3x?? and MgZryF2+4y??, wherein x and y have, independently of one another, values in the range of from 0 to 0.33 and ? has a value in the range of from 0 to 0.1. Certain hydrofluorochloroalkenes are also described, as well as their use as intermediates in chemical reactions.
    Type: Grant
    Filed: March 31, 2011
    Date of Patent: December 30, 2014
    Assignee: Solvay SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • Patent number: 8912371
    Abstract: A method of producing a chlorinated hydrocarbon having 3 carbon atoms, comprising a conversion step for converting a chloropropane represented by the following formula (1) into a chloropropane represented by the following formula (2) by reacting it with chlorine in the presence of anhydrous aluminum chloride. CCl3—CCl(2-m)Hm—CCl(3-n)Hn??(1) (In the above formula (1), m is 1 or 2, and n is an integer of 0 to 3.) CCl3—CCl(3-m)H(m-1)—CCl(3-n)Hn??(2) (In the above formula (2), m and n are the same integers as in the formula (1), respectively.
    Type: Grant
    Filed: December 1, 2011
    Date of Patent: December 16, 2014
    Assignee: Tokuyama Corporation
    Inventors: Shunsuke Hosaka, Yasutaka Komatsu, Masayuki Moriwaki, Kikuo Yamamoto, Naoya Okada
  • Patent number: 8912369
    Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes bringing a composition containing a compound of the general formula (1): CF3—CH2—CHClX (where X is a fluorine atom or a chlorine atom) into contact with a solid catalyst in the presence of hydrogen chloride. In this production method, the composition containing ozone depleting HCFC such as 3-chloro-1,1,1,3-tetraluoforpropane or 3,3-dichloro-1,1,1-trifluoropropane can be efficiently converted to the 1-chloro-3,3,3-trifluoropropene, which has less influence on the global environment and is useful as a solvent, a cleaning agent, a coolant, a working fluid, a propellant, a raw material for fluorinated resins etc.
    Type: Grant
    Filed: June 27, 2013
    Date of Patent: December 16, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Hideaki Imura, Naoto Takada
  • Patent number: 8912372
    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: November 15, 2013
    Date of Patent: December 16, 2014
    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: 8907147
    Abstract: The present invention provides an improved process for producing 1,1,2,3-tetrachloropropene. By using a first reactive distillation column for HCC-250fb dehydrochlorination, and a second reactive distillation column for HCC-240db dehydrochlorination/HCC-1230xf isomerization, the 1,1,2,3-tetrachloropropene manufacturing process can be greatly simplified, resulting in reduced equipment use, energy use, as well as increased productivity.
    Type: Grant
    Filed: January 30, 2014
    Date of Patent: December 9, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Joshua Close, Terris Tianxue Yang
  • Patent number: 8889928
    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. The present invention demonstrates that when using FeCl3 as the catalyst for 1,1,1,3-tetrachloropropane dehydrochlorination, the reaction product contains significant amounts of high boiling compounds, such as pentachlorocyclohexene and/or hexachlorocyclohexane species. The addition of one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system, inhibits the formation of these high boiling compounds and improves selectivity to the desired product.
    Type: Grant
    Filed: March 12, 2013
    Date of Patent: November 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Terris Yang, Hsueh Sung Tung
  • Patent number: 8889929
    Abstract: Disclosed is a process for the synthesis of 1,1,2,3-tetrachloropropene (HCC-1230xa) using 1,1,3-trichloropropene (HCC-1240za) and/or 3,3,3-trichloropropene (HCC-1240zf) and Cl2 gas as the reactants, wherein the process takes place in a single reactor system. Before this invention, HCC-1230xa was made in a two-step process using HCC-1240za/HCC-1240zf and Cl2 gas, and the processing was conducted using two separate reactors.
    Type: Grant
    Filed: February 17, 2014
    Date of Patent: November 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Terris Yang, Hsueh Sung Tung
  • 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
  • Patent number: 8884082
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a carbon catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein Rf is a perfluorinated alkyl group.
    Type: Grant
    Filed: February 16, 2012
    Date of Patent: November 11, 2014
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Patent number: 8841493
    Abstract: The subject matter of the invention is a process for preparing fluoroolefin compounds. The invention relates more particularly to a process for producing a (hydro)fluoroolefin compound, which comprises (i) bringing at least one compound comprising from three to six carbon atoms, at least two fluorine atoms and at least one hydrogen atom, on the condition that at least one hydrogen atom and one fluorine atom are located on adjacent carbon atoms, into contact with a solid reactant comprising calcium hydroxide.
    Type: Grant
    Filed: May 4, 2010
    Date of Patent: September 23, 2014
    Assignee: Arkema France
    Inventors: Dominique Guillet, Michel Devic
  • Publication number: 20140275658
    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: Application
    Filed: March 12, 2013
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Terris Yang, Joshua Close, Hsueh Sung Tung
  • Publication number: 20140275659
    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. The present invention demonstrates that when using FeCl3 as the catalyst for 1,1,1,3-tetrachloropropane dehydrochlorination, the reaction product contains significant amounts of high boiling compounds, such as pentachlorocyclohexene and/or hexachlorocyclohexane species. The addition of one or more UV-stabilizer and/or anti-oxidant compounds, or mixtures thereof, into the dehydrochlorination reaction system, inhibits the formation of these high boiling compounds and improves selectivity to the desired product.
    Type: Application
    Filed: March 12, 2013
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Terris Yang, Hsueh Sung Tung
  • 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: 20140235907
    Abstract: This invention relates to a method to improve 1,1,3-trichloropropene selectivity in HCC-250fb (1,1,1,3-tetrachloropropane) dehydrochlorination. In normal practice, FeCl3 is used as the catalyst for the dehydrochlorination of HCC-250fb to produce 1,1,3-tri-chloropropene. In this invention as source of water is added into the reaction system to inhibit the formation of high boiling compounds such as pentachlorocyclohexene and/or hexachlorocyclohexane. Once source of water is H2O itself. Another source of water is one or more hydrated metal halides.
    Type: Application
    Filed: February 17, 2014
    Publication date: August 21, 2014
    Applicant: Honeywell International Inc.
    Inventors: Terris Yang, Hsueh Sung Tung, Robert Johnson, Joshua Close
  • Publication number: 20140100394
    Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of a feedstream comprising 1,2-dichloropropane, a by-product in the production of chlorohydrin, as a low cost starting material, alone or in combination with 1,2,3-trichloropropane. Selectivity of the process is enhanced over conventional processes employing successive chlorinations and/or dehydrochlorinations, by conducting at least one chlorination in the presence of an ionic chlorination catalyst. The present processes may also generate anhydrous HCl as a byproduct that can be removed from the process and used as a feedstock for other processes, providing further time and cost savings.
    Type: Application
    Filed: May 18, 2012
    Publication date: April 10, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES, LLC
    Inventors: Max M. Tirtowidjojo, William J. Kruper, JR., Barry B. Fish, David S. Laitar
  • Patent number: 8614363
    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: August 17, 2012
    Date of Patent: December 24, 2013
    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: 8586804
    Abstract: Disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising contacting 1,1,1,3,tetrachloropropane in the vapor phase in a reaction zone with a catalyst comprising iron, to produce a product mixture comprising 1,1,3-trichloro-1-propene; and recovering said 1,1,3-trichloro-1-propene from the product mixture produced. Also disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising heating 1,1,1,3-tetrachloropropane in the liquid phase to produce a mixture comprising 1,1,3-trichloro-1-propene, cooling said mixture, separating hydrogen chloride from said mixture and recovering 1,1,3-trichloro-1-propene.
    Type: Grant
    Filed: October 21, 2011
    Date of Patent: November 19, 2013
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Robert D. Lousenberg, Andrew Jackson
  • Publication number: 20130204052
    Abstract: The present invention discloses a catalyst used in preparing vinyl chloride, its method of preparation, and its applications. Said catalyst used in making vinyl chloride comprises activated carbon as a support, a barium compound and a phosphorus compound supported thereon. The barium compound accounts for 0.2% to 20% of the total mass of the catalyst and the phosphorus compound accounts for 0% to 10% of the total mass of the catalyst based on the mass percentage. A water-soluble barium compound, a water-soluble phosphorus compound, an aqueous polymer monomer, and water are mixed to form a solution or emulsion A. The activated carbon is added into the solution or emulsion A. The activated carbon is removed from water after impregnation, spin-dried, and then the monomers are polymerized. The activated carbon, after polymerization step, is heated to remove water and to decompose and carbonize the polymer. The catalyst after carbonization was activated to obtain a catalyst used in making vinyl chloride.
    Type: Application
    Filed: October 26, 2011
    Publication date: August 8, 2013
    Applicants: Zhongke Yigong (Xiamen) Chemical Technology Co. Ltd., Shanghai CAS Advanced Research Institute
    Inventors: Biao Jiang, Jinguang Zhong
  • Publication number: 20130165705
    Abstract: A method of producing a chlorinated hydrocarbon having 3 carbon atoms, comprising a conversion step for converting a chloropropane represented by the following formula (1) into a chloropropane represented by the following formula (2) by reacting it with chlorine in the presence of anhydrous aluminum chloride. CCl3—CCl(2-m)Hm—CCl(3-n)Hn??(1) (In the above formula (1), m is 1 or 2, and n is an integer of 0 to 3.) CCl3—CCl(3-m)H(m-1)—CCl(3-n)Hn??(2) (In the above formula (2), m and n are the same integers as in the formula (1), respectively.
    Type: Application
    Filed: December 1, 2011
    Publication date: June 27, 2013
    Applicant: TOKUYAMA CORPORATION
    Inventors: Shunsuke Hosaka, Yasutaka Komatsu, Masayuki Moriwaki, Kikuo Yamamoto, Naoya Okada
  • Publication number: 20130012743
    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: Application
    Filed: August 17, 2012
    Publication date: January 10, 2013
    Inventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
  • Patent number: 8258355
    Abstract: Provided is a continuous process for preparing 1,1,2,3-tetrachloro-1-propene having the steps of catalytically dehydrochlorinating CH2ClCCl2CH2Cl in the gas phase to produce CHCl?CClCH2Cl; chlorinating the CHCl?CClCH2Cl to form CHCl2CCl2CH2Cl; and catalytically dehydrochlorinating the CHCl2CCl2CH2Cl in the gas phase to form CCl2?CClCH2Cl.
    Type: Grant
    Filed: July 24, 2008
    Date of Patent: September 4, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung, Michael Van Der Puy, Jing Ji Ma
  • Publication number: 20120142981
    Abstract: A production method of 1,1,3-trichloro-1-propene comprising the following steps A and B; Step A: 1,1,1,3-tetrachloropropane is dehydrochlorinated at a temperature between 30° C. and 50° C. in the presence of at least one base selected from the group consisting of alkali metal hydroxides and alkaline earth metal hydroxides, and a phase transfer catalyst, Step B: 3,3,3-trichloro-1-propene obtained in the step A is isomerized into 1,1,3-trichloro-1-propene in the presence of a metal catalyst.
    Type: Application
    Filed: August 27, 2010
    Publication date: June 7, 2012
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Hiroshi Souda, Koji Hagiya
  • Publication number: 20120142980
    Abstract: Disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising contacting 1,1,1,3,tetrachloropropane in the vapor phase in a reaction zone with a catalyst comprising iron, to produce a product mixture comprising 1,1,3-trichloro-1-propene; and recovering said 1,1,3-trichloro-1-propene from the product mixture produced. Also disclosed is a process for the dehydrochlorination of 1,1,1,3-tetrachloropropane comprising heating 1,1,1,3-tetrachloropropane in the liquid phase to produce a mixture comprising 1,1,3-trichloro-1-propene, cooling said mixture, separating hydrogen chloride from said mixture and recovering 1,1,3-trichloro-1-propene.
    Type: Application
    Filed: October 21, 2011
    Publication date: June 7, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: MARIO JOSEPH NAPPA, ROBERT D. LOUSENBERG, ANDREW JACKSON
  • Patent number: 8178466
    Abstract: The present disclosure provides methods for pre-treating activated carbon before it is used in a dehydrochlorination process. The methods can comprise mixing the activated carbon with an acid, an oxidizing agent in a liquid phase, or an oxidizing agent in a gas phase. Activated carbons undergoing one or more of these methods can exhibit improved stability during the dehydrochlorination process.
    Type: Grant
    Filed: January 14, 2011
    Date of Patent: May 15, 2012
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh S. Tung
  • Publication number: 20120053374
    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: June 17, 2010
    Publication date: March 1, 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
  • Publication number: 20120035402
    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: Application
    Filed: October 13, 2011
    Publication date: February 9, 2012
    Applicant: OCCIDENTAL CHEMICAL CORPORATION
    Inventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
  • Patent number: 8030531
    Abstract: 2,3-dichlorobutadiene-1,3 of high purity is produced from 1,2,3,4-tetrachlorobutane by a process comprising the steps of dehydrochlorination, chlorination of the reaction product obtained in the dehydrochlorination step and subsequent separation of a 2,3-dichlorobutadiene-1,3 composition from the reaction product of the chlorination step.
    Type: Grant
    Filed: December 16, 2008
    Date of Patent: October 4, 2011
    Assignee: Dupont Performance Elastomers LLC
    Inventor: Terry Wayne Redwine
  • Patent number: 8026400
    Abstract: Purified chlorinated alkenes are produced by a process in which a mixture of i) a first chlorinated alkene that has at least one beta-chlorine substituent and no alpha-chlorine substituents and ii) a second chlorinated alkene that has at least one alpha-chlorine substituent is contacted with chlorine in an amount sufficient to further chlorinate the second chlorinated alkene, but which is insufficient to cause conversion of more than 20% of the first chlorinated alkene.
    Type: Grant
    Filed: December 16, 2008
    Date of Patent: September 27, 2011
    Assignee: Dupont Performance Elastomers LLC
    Inventor: Terry Wayne Redwine
  • Publication number: 20090312586
    Abstract: Methods and systems for the hydrogenation of multi-brominated alkanes are provided herein. An embodiment of the present invention comprises a method, the method comprising: reacting at least hydrogen and multi-brominated alkanes in the presence of a catalyst to form a hydrogenated stream comprising brominated alkanes having fewer bromine substituents than the multi-brominated alkanes reacted with the hydrogen. Embodiments of the method further may comprise forming brominated alkanes. Embodiments of the method further may comprising forming product hydrocarbons from brominated alkanes.
    Type: Application
    Filed: June 13, 2008
    Publication date: December 17, 2009
    Applicant: MARATHON GTF TECHNOLOGY, LTD.
    Inventors: John J. Waycuilis, William J. Turner
  • Publication number: 20090163745
    Abstract: 2,3-dichlorobutadiene-1,3 of high purity is produced from 1,2,3,4-tetrachlorobutane by a process comprising the steps of dehydrochlorination, chlorination of the reaction product obtained in the dehydrochlorination step and subsequent separation of a 2,3-dichlorobutadiene-1,3 composition from the reaction product of the chlorination step.
    Type: Application
    Filed: December 16, 2008
    Publication date: June 25, 2009
    Inventor: TERRY WAYNE REDWINE
  • Publication number: 20090118555
    Abstract: An integrated process for the manufacture of HFO trans-1,3,3,3-tetrafluoropropene (HFO trans-1234ze) by first catalytically dehydrofluorinating 1,1,1,3,3-pentafluoropropane to thereby produce a mixture of cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and hydrogen fluoride. Then optionally recovering hydrogen fluoride, catalytically isomerizing cis-1234ze into trans-1234ze, and recovering trans-1,3,3,3-tetrafluoropropene.
    Type: Application
    Filed: January 5, 2009
    Publication date: May 7, 2009
    Inventors: Haiyou Wang, Hsueh Sung Tung, Yuon Chiu, Gustavo Cerri, Stephen A. Cottrell
  • Publication number: 20090030249
    Abstract: Provided is a continuous process for preparing 1,1,2,3-tetrachloro-1-propene having the steps of catalytically dehydrochlorinating CH2ClCCl2CH2Cl in the gas phase to produce CHCl?CClCH2Cl; chlorinating the CHCl?CClCH2Cl to form CHCl2CCl2CH2Cl; and catalytically dehydrochlorinating the CHCl2CCl2CH2Cl in the gas phase to form CCl2?CClCH2Cl.
    Type: Application
    Filed: July 24, 2008
    Publication date: January 29, 2009
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh S. Tung, Michael Van Der Puy, Jing Ji Ma
  • Publication number: 20080242902
    Abstract: Described are compositions adapted to catalyze the vapor phase dehydrohalogenation of 1,1,2-trihaloethane to 1,1-dihaloethylene, e.g., 1,1,2-trichloroethane to vinylidene chloride. These materials include activated carbon and at least one benzimidazole-containing material defined herein as including benzimidazole, a derivative thereof, a salt thereof or mixtures thereof. Also described are methods for producing and using these catalytic compositions.
    Type: Application
    Filed: June 3, 2005
    Publication date: October 2, 2008
    Applicant: PPG INDUSTRIES OHIO, INC
    Inventors: Yurii Oleksiyovych Serhuchev, Yurii Vasyliyovych Bilokopytov, Igorlvanovych Chernobaev
  • Patent number: 7135601
    Abstract: A process for producing a producing a product of the formula: R—CF?CHR1 wherein R is F or CF3 and R1 is F when R is F and is H when R is CF3 by reacting a reactant of the formula: CF3—R2 wherein R2 is selected from and wherein R3 is H, F or Cl and R4 is H or Cl, in the presence of a suitable catalyst, with a reducing agent selected from methane, methyl chloride and mixtures thereof, in a gas phase reaction.
    Type: Grant
    Filed: March 28, 2005
    Date of Patent: November 14, 2006
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, HsuehSung Tung