Unsaturated Patents (Class 570/135)
  • Patent number: 10343962
    Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, particularly, 1,1,2,3-tetrachloropropene (1230xa), oligomerization/polymerization of such starting reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that providing one or more organic co-feed to the fluooolefin starting stream reduces such oligomerization/polymerization and improves catalystic stability.
    Type: Grant
    Filed: March 21, 2017
    Date of Patent: July 9, 2019
    Assignee: Honeywell International Inc.
    Inventors: Selma Bektesevic, Daniel C. Merkel, Mario Joseph Nappa, Xuehui Sun, Hsueh Sung Tung, Haiyou Wang
  • Patent number: 10119055
    Abstract: A stable composition (CS) including at least x wt.-% 2,3,3,3-tetrafluoropropene (99.8 ÿ x<100), at most y wt.-% unsaturated compound(s) (Ia) (0<y ÿ 0.2) selected from among 3,3,3-trifluoropropene (HFO-1243zf) and the positional isomers of 2,3,3,3-tetrafluoropropene, such as 1,3,3,3-tetrafluoropropene (isomers Z and E) and 1,1,2,3-tetrafluoropropene, and, optionally, at most 500 ppm of 3,3,3-trifluoropropyne and/or at most 200 ppm 1,1,1,2,3-pentafluoropropene (HFO-1225ye).
    Type: Grant
    Filed: January 7, 2016
    Date of Patent: November 6, 2018
    Assignee: ARKEMA FRANCE
    Inventor: Beatrice Boussand
  • Patent number: 10053405
    Abstract: The present invention provides a method for producing a fluorine-containing haloolefin compound, said method being able to reduce the generation of overly fluorinated compounds as by-products in the production of the fluorine-containing haloolefin compound and produce the target product of high purity at a high yield. The invention also provides a halogenated hydrocarbon composition. The method for producing a haloolefin compound through the step of fluorinating a starting material containing at least one of a pentachloropropane or a tetrachloropropene in the presence of a fluorinating agent in a reactor, according to the present invention, includes the step of adding hydrogen chloride to the reactor. The composition according to the present invention contains: at least one member selected from the group consisting of a pentachloropropane and a tetrachloropropene; and hydrogen chloride.
    Type: Grant
    Filed: October 7, 2015
    Date of Patent: August 21, 2018
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Daisuke Karube, Masayuki Kishimoto, Yuzo Komatsu, Takehiro Chaki
  • Patent number: 10047023
    Abstract: This invention provides a method for producing 2,3,3,3-tetrafluoropropene or 2-chloro-1,1,1,2-tetrafluoropropane, which is a precursor of 2,3,3,3-tetrafluoropropene, in two or three reaction steps, using at least one chlorine-containing compound selected from the group consisting of 1,1,1,2,3-pentachloropropane, 2,3-dichloro-1,1,1-trifluoropropane, and 1,1,2,3-tetrachloropropene as a starting material, the reaction products of at least two of the steps being supplied to the same distillation apparatus to subject the products to a separation operation simultaneously. With this method, 2,3,3,3-tetrafluoropropene or 2-chloro-1,1,1,2-tetrafluoropropane, which is a precursor of 2,3,3,3-tetrafluoropropene, can be efficiently produced with reduced energy and equipment costs in an economically advantageous manner.
    Type: Grant
    Filed: June 23, 2016
    Date of Patent: August 14, 2018
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Takehiro Chaki, Kazuhiro Takahashi, Tatsuya Takakuwa
  • Patent number: 10023510
    Abstract: This invention provides a method for producing 2,3,3,3-tetrafluoropropene or 2-chloro-1,1,1,2-tetrafluoropropane, which is a precursor of 2,3,3,3-tetrafluoropropene, in two or three reaction steps, using at least one chlorine-containing compound selected from the group consisting of 1,1,1,2,3-pentachloropropane, 2,3-dichloro-1,1,1-trifluoropropane, and 1,1,2,3-tetrachloropropene as a starting material, the reaction products of at least two of the steps being supplied to the same distillation apparatus to subject the products to a separation operation simultaneously. With this method, 2,3,3,3-tetrafluoropropene or 2-chloro-1,1,1,2-tetrafluoropropane, which is a precursor of 2,3,3,3-tetrafluoropropene, can be efficiently produced with reduced energy and equipment costs in an economically advantageous manner.
    Type: Grant
    Filed: June 23, 2016
    Date of Patent: July 17, 2018
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Takehiro Chaki, Kazuhiro Takahashi, Tatsuya Takakuwa
  • Patent number: 10022576
    Abstract: Hydrofluoroolefins and hydrochlorofluoroolefins contaminated with acid and/or iron compounds are purified and stabilized by contacting the haloolefin with a solid adsorbent such as alumina and then combining the purified haloolefin with one or more stabilizers such as an epoxide. The purified, stabilized haloolefins thus obtained are useful in a wide variety of end-use applications, including, for example, as refrigerants, propellants, foaming agents, fire suppression or extinguishing agents, and solvents.
    Type: Grant
    Filed: February 28, 2014
    Date of Patent: July 17, 2018
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet
  • Patent number: 9938209
    Abstract: This invention provides a method for producing 2,3,3,3-tetrafluoropropene or 2-chloro-1,1,1,2-tetrafluoropropane, which is a precursor of 2,3,3,3-tetrafluoropropene, in two or three reaction steps, using at least one chlorine-containing compound selected from the group consisting of 1,1,1,2,3-pentachloropropane, 2,3-dichloro-1,1,1-trifluoropropane, and 1,1,2,3-tetrachloropropene as a starting material, the reaction products of at least two of the steps being supplied to the same distillation apparatus to subject the products to a separation operation simultaneously. With this method, 2,3,3,3-tetrafluoropropene or 2-chloro-1,1,1,2-tetrafluoropropane, which is a precursor of 2,3,3,3-tetrafluoropropene, can be efficiently produced with reduced energy and equipment costs in an economically advantageous manner.
    Type: Grant
    Filed: June 23, 2016
    Date of Patent: April 10, 2018
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Takehiro Chaki, Kazuhiro Takahashi, Tatsuya Takakuwa
  • Patent number: 9902671
    Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.
    Type: Grant
    Filed: January 10, 2017
    Date of Patent: February 27, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9670117
    Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, particularly, 1,1,2,3-tetrachloropropene (1230xa), oligomerization/polymerization of such starting reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that providing one or more organic co-feed to the fluoroolefin starting stream reduces such oligomerization/polymerization and improves catalystic stability.
    Type: Grant
    Filed: November 2, 2012
    Date of Patent: June 6, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Selma Bektesevic, Daniel C. Merkel, Mario Joseph Nappa, Xuehui Sun, Hsueh Sung Tung, Haiyou Wang
  • Patent number: 9493384
    Abstract: The present invention relates, in part, to the discovery that the presence of HF in a HCFC-244bb feedstream in a reaction for the preparation of HFO-1234yf results in selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing HF, it is shown that the selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is improved.
    Type: Grant
    Filed: September 29, 2012
    Date of Patent: November 15, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20150148570
    Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.
    Type: Application
    Filed: January 30, 2015
    Publication date: May 28, 2015
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Patent number: 9035111
    Abstract: A method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3(—CX2X2)nCX1?H2??(I) to at least one compound of formula (II): CF3(CX2X2)nCX1?H2??(II), where X1 is Cl, Br or I, each X2 is independently selected from the group consisting of H, Cl, F, Br or J, and n is 0, 1, or 2.
    Type: Grant
    Filed: August 21, 2008
    Date of Patent: May 19, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Sudip Mukhopadhyay, Cheryl L. Bortz, Kim M. Fleming, Steven D. Phillips, Rajesh K. Dubey
  • Patent number: 9035112
    Abstract: Disclosed is a process for producing 2-chloro-1,3,3,3-tetrafluoropropene (1224), including a first step of separating 2,3-dichloro-1,1,1,3-tetrafluoropropane (234da) into erythro form and threo form, and a second step of bringing the separated erythro form or threo form in contact with a base to obtain 2-chloro-1,3,3,3-tetrafluoropropene (1224). The first step is a step of separating 234da by distillation to achieve a separation into a fraction containing mainly erythro form and a fraction containing mainly threo form. In the second step, 1224 cis form is obtained from the erythro form, and 1224 trans form is obtained from the threo form. By this process, it is possible to selectively and efficiently produce cis form or trans form of 2-chloro-1,3,3,3-tetrafluoropropene (1224).
    Type: Grant
    Filed: May 8, 2014
    Date of Patent: May 19, 2015
    Assignee: Central Glass Company, Ltd.
    Inventors: Hideaki Imura, Yoshio Nishiguchi, Masamune Okamoto, Tatsuya Hayasaka, Minako Oomura, Satoru Okamoto, Naoto Takada
  • 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: 9000238
    Abstract: The present disclosure relates to a process for separating a fluoroolefin from a mixture comprising hydrogen fluoride and fluoroolefin, comprising azeotropic distillation both with and without an entrainer. In particular are disclosed processes for separating any of HFC-1225ye, HFC-1234ze, HFC-1234yf or HFC-1243zf from HF.
    Type: Grant
    Filed: August 16, 2012
    Date of Patent: April 7, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: Jeffrey P. Knapp, Barry Asher Mahler, Donald J. Toton
  • Publication number: 20150065746
    Abstract: To address the problem of insufficient biodegradability of perfluorinated surfactants, the present invention provides biodegradable fluorosurfactants derived from olefins having —CHR, —CHRf, —CHF, and/or —CH2 groups, where R is an alkyl group and Rf is a perfluoro or fluroroalkyl group. Preferably, the —CHR, —CHRf, —CHF, and/or —CH2 groups are contained within partially fluorinated alkenes.
    Type: Application
    Filed: August 14, 2014
    Publication date: March 5, 2015
    Inventors: Haridasan K. Nair, Yian Zhai, Andrew J. Poss, Rajiv R. Singh, David Nalewajek
  • Publication number: 20150011803
    Abstract: Provided is a purification method for efficiently reducing an undesirable organic compound or compound in (E)-1-chloro-3,3,3-trifluoropropene and thereby obtaining (E)-1-chloro-3,3,3-trifluoropropene with high purity. The purification method of OF-1233E according to the present invention is characterized by bringing a composition containing OF-1233E and at least one organic compound selected from the group consisting of HCFC-142 isomers, HCFC-244fa, HFC-245fa, OF-1234E, OF-1234Z and OF-1233Z into contact with a solid adsorbent.
    Type: Application
    Filed: January 24, 2013
    Publication date: January 8, 2015
    Applicant: Central Glass Company, Limited
    Inventors: Hideaki Imura, Naoto Takada, Masamune Okamoto
  • Publication number: 20140366540
    Abstract: Aspects of the present invention are directed to working fluids and their use in processes wherein the working fluids comprise compounds having the structure of formula (I): wherein R1, R2, R3, and R4 are each independently selected from the group consisting of: H, F, Cl, Br, and C1-C6 alkyl, at least C6 aryl, at least C3 cycloalkyl, and C6-C15 alkylaryl optionally substituted with at least one F, Cl, or Br, wherein formula (I) contains at least one F and at least one Cl or Br, provided that if any R is Br, then the compound does not have hydrogen. The working fluids are useful in Rankine cycle systems for efficiently converting waste heat generated from industrial processes, such as electric power generation from fuel cells, into mechanical energy or further to electric power. The working fluids of the invention are also useful in equipment employing other thermal energy conversion processes and cycles.
    Type: Application
    Filed: September 2, 2014
    Publication date: December 18, 2014
    Inventors: Gary Zyhowski, Ryan J. Hulse, Haridasan K. Nair, David Nalewajek, Rajiv R. Singh
  • Patent number: 8889925
    Abstract: The present invention provides a process of fluorination in liquid phase in a solvent medium of a compound of formula (II) CX1X2?CZCX3X4X5, in which Z represents H, Cl or F, and each X1 represents independently hydrogen or chlorine, given that at least one of the X1 represents a chlorine.
    Type: Grant
    Filed: March 10, 2010
    Date of Patent: November 18, 2014
    Assignee: Arkema France
    Inventor: Anne Pigamo
  • Publication number: 20140264174
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,3,3,3-tetrachloroprop-1-ene (HCO-1230zd) and hydrogen fluoride. Such compositions are useful as a feed stock in the production of HFC245fa and HCFO1233zd.
    Type: Application
    Filed: March 13, 2013
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Haiyou Wang, Hsueh Sung Tung, Ryan Hulse, Hang T. Pham
  • Publication number: 20140131614
    Abstract: To provide a working medium for heat cycle which has inflammability suppressed, which has less influence over the ozone layer, which has less influence over global warming and which provides a heat cycle system excellent in the cycle performance (efficiency), and a heat cycle system whereby safety is secured and which is excellent in the cycle performance (efficiency). A working medium for heat cycle comprising 1,1-dichloro-2,3,3,3-tetrafluoropropene is employed for a heat cycle system (such as a Rankine cycle system, a heat pump cycle system, a refrigerating cycle system 10 or a heat transport system).
    Type: Application
    Filed: January 22, 2014
    Publication date: May 15, 2014
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventor: Masato FUKUSHIMA
  • Publication number: 20140077122
    Abstract: To provide a working medium for heat cycle, of which combustibility is suppressed, which has less influence over the ozone layer, which has less influence over global warming and which provides a heat cycle system excellent in the cycle performance (efficiency and capacity), and a heat cycle system, of which the safety is secured, and which is excellent in the cycle performance (efficiency and capacity). A working medium for heat cycle comprising 1-chloro-2,3,3,3-tetrafluoropropene is employed for a heat cycle system (such as a Rankine cycle system, a heat pump cycle system, a refrigerating cycle system 10 or a heat transport system).
    Type: Application
    Filed: November 19, 2013
    Publication date: March 20, 2014
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventor: Masato FUKUSHIMA
  • Publication number: 20140073139
    Abstract: The present invention is a plasma etching gas comprising a fluorocarbon having 3 or 4 carbon atoms, the fluorocarbon including at least one unsaturated bond and/or ether linkage, and including a bromine atom, and a plasma etching method comprising subjecting a silicon oxide film on a substrate to plasma etching through a mask using a process gas, the process gas being the plasma etching gas. This plasma etching gas exhibits excellent etching selectivity, and has a short atmospheric lifetime and a low environmental impact. This plasma etching method makes it possible to selectively subject a silicon oxide film to plasma etching at a high etching rate without causing an increase in surface roughness.
    Type: Application
    Filed: March 14, 2012
    Publication date: March 13, 2014
    Applicant: ZEON CORPORATION
    Inventor: Takefumi Suzuki
  • Publication number: 20140057826
    Abstract: The present invention relates to solvent/cleaner and heat transfer fluid compositions comprising at least one hydrochlorofluoroolefin (HCFO), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), particularly the trans-isomer. The HCFO of the present invention can be used in combination with co-agents including, hydrofluorocarbons (HFCs), hydrofluomolefins (HFOs), hydrocarbons, ethers including hydrofluoroethers (HFEs), esters, ketones, alcohols, 1,2-transdichloroethylene and mixtures thereof.
    Type: Application
    Filed: February 21, 2013
    Publication date: February 27, 2014
    Applicant: Arkema Inc.
    Inventors: Benjamin Bin Chen, Philippe Bonnet, Maher Y. Elsheikh, Brett L. Van Horn, Laurent Abbas
  • Patent number: 8618340
    Abstract: Disclosed is a process for the manufacture of HFO-1234yf from TCP in three integrated steps that include hydrofluorination of TCP (tetrachloropropene) to HCFC-1233xf in the vapor phase followed by hydrofluorination of HCFC-1233xf to HCFC-244bb in the liquid phase which is then followed by dehydrochlorination in liquid or vapor phase to produce HFO-1234yf. The vapor phase hydrofluorination is carried out at a higher pressure than the liquid phase hydrofluorination, thereby eliminating the need for compression and/or intermediate recovery. Also, any HCl generated from this reaction is fed to the liquid phase hydrofluorination section to promote agitation and mixing. This results in a more economical process from an initial capital and operating cost versus conducting the 3-steps sequentially.
    Type: Grant
    Filed: November 3, 2009
    Date of Patent: December 31, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Kevin Uhrich
  • Patent number: 8609907
    Abstract: One or more hydrochlorofluoroalkenes can be produced by dehydrofluorination of a hydrochlorofluoroalkane over a X-ray amorphous high surface metal fluoride or a X-ray amorphous or weakly crystalline metal oxide fluoride wherein the metal is selected from the 2nd, 3rd or 4th main group or any subgroup of the periodic system of elements. High-surface aluminum fluoride or aluminum oxide fluoride are especially suitable as catalysts. For example, CF3CH2CHClF is reacted to produce CF3CH?CHCl, and CF3CH2CClFCH3 is reacted to form CF3CH2CCl?CH2 and/or CF3CH?CClCH3.
    Type: Grant
    Filed: November 20, 2009
    Date of Patent: December 17, 2013
    Assignee: Solvay Fluor GmbH
    Inventors: Johannes Eicher, Wolfgang Kalbreyer, Ercan Uenveren
  • Patent number: 8541634
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Grant
    Filed: January 14, 2013
    Date of Patent: September 24, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T Pham
  • Publication number: 20130228714
    Abstract: Compositions and methods based on the use of fluoroalkene containing from 3 to 4 carbon atoms and at least one carbon-carbon double bond, such as HFO-1214, HFO-HFO-1233, or HFO-1354, having properties highly beneficial in foaming and blowing agent applications, articles and methods.
    Type: Application
    Filed: April 15, 2013
    Publication date: September 5, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: ROBERT C. JOHNSON, HSUEH S. TUNG, RAJIV R. SINGH, IAN SHANKLAND
  • Publication number: 20130091843
    Abstract: Aspects of the present invention are directed to working fluids and their use in processes wherein the working fluids comprise compounds having the structure of formula (I): wherein R1, R2, R3, and R4 are each independently selected from the group consisting of: H, F, Cl, Br, and C1-C6 alkyl, at least C6 aryl, at least C3 cycloalkyl, and C6-C15 alkylaryl optionally substituted with at least one F, Cl, or Br, wherein formula (I) contains at least one F and optionally at least one Cl or Br, provided that if any R is Br, then the compound does not have hydrogen. The working fluids are useful in Rankine cycle systems for efficiently converting waste heat generated from industrial processes, such as electric power generation from fuel cells, into mechanical energy or further to electric power. The working fluids of the invention are also useful in equipment employing other thermal energy conversion processes and cycles.
    Type: Application
    Filed: November 30, 2012
    Publication date: April 18, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: Honeywell International Inc.
  • Patent number: 8378158
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: February 19, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham
  • Publication number: 20130023703
    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: Application
    Filed: March 31, 2011
    Publication date: January 24, 2013
    Applicant: SOLVAY SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • Patent number: 8357828
    Abstract: To provide a simple and economical process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, which does not require purification of the raw material component obtained in the form of a mixture of isomers, and a process for producing 2,3,3,3-tetrafluoropropene from the product thereby obtained. A process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, characterized by bringing a mixture of dichloropentafluoropropane isomers which contains 1,1-dichloro-2,2,3,3,3-pentafluoropropane into contact with an aqueous alkali solution in the presence of a phase transfer catalyst, and thereby selectively dehydrofluorinating only the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture, and a process for producing 2,3,3,3-tetrafluoropropene from the 1,1-dichloro-2,3,3,3-tetrafluoropropene thereby obtained.
    Type: Grant
    Filed: June 20, 2011
    Date of Patent: January 22, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Hidekazu Okamoto, Yasuyuki Sasao
  • Publication number: 20120296127
    Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.
    Type: Application
    Filed: May 15, 2012
    Publication date: November 22, 2012
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Patent number: 8299309
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF?CHR from halofluorocarbons of the structure RfCFX2. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(?O)R?.
    Type: Grant
    Filed: October 11, 2011
    Date of Patent: October 30, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Patent number: 8293953
    Abstract: To provide a method for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) at a high content ratio, which is useful as e.g. a starting material to obtain 1,1-dichloro-2,3,3,3-tetrafluoropropene (R1214ya). The method comprises subjecting a starting material comprising one isomer or a mixture of at least two isomers of dichloropentafluoropropane (HCFC-225) and having a HCFC-225ca content of less than 60 mol %, to an isomerization reaction in the presence of a Lewis acid catalyst or a metal oxide catalyst so as to increase the HCFC-225ca content in the product to be higher than the content in the starting material.
    Type: Grant
    Filed: March 21, 2011
    Date of Patent: October 23, 2012
    Assignee: Asahi Glass Company, Limited
    Inventor: Hidekazu Okamoto
  • Patent number: 8273928
    Abstract: The present disclosure relates to a process for separating a fluoroolefin from a mixture comprising hydrogen fluoride and fluoroolefin, comprising azeotropic distillation both with and without an entrainer. In particular are disclosed processes for separating any of HFC-1225ye, HFC-1234ze, HFC-1234yf or HFC-1243zf from HF.
    Type: Grant
    Filed: August 24, 2007
    Date of Patent: September 25, 2012
    Assignee: E I Du Pont de Nemours and Company
    Inventors: Jeffrey P. Knapp, Barry Asher Mahler, Donald J. Toton
  • Publication number: 20120172636
    Abstract: The present invention discloses high purity E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and methods to produce the same. More specifically, the present invention discloses the methods of making 1233zd(E) essentially free of toxic impurities (e.g. 2-chloro-3,3,3-trifluoropropene (1233xf), chlorotetrafluoro-propene (1224), and 3,3,3-trifluoropropyne). The present invention further provides methods for making high purity 1233zd(E) with concentration of 1233xf and 1224 at or below 200 parts per million (ppm) and 3,3,3-trifluoropropyne impurities at or below 20 ppm. Formation of 1233xf impurity can be avoided if pure 1,1,1,3,3-pentachloropropane is used as a starting material. It was also found that formation of 1233xf is avoided if a liquid phase manufacturing process is used.
    Type: Application
    Filed: January 4, 2011
    Publication date: July 5, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Konstantin A. Pokrovski, Rajiv Ratna Singh, Ian Shankland, Hsueh Sung Tung
  • Publication number: 20120172476
    Abstract: The present invention relates to a method of producing more uniformly distributed polyurethane form using blowing agents. More particularly, the present invention relates to a method of producing more uniformly distributed polyurethane foam for an application in which flow of liquid polyurethane foam prior to solidification is important to its performance using a hydrochlorofluoroolefin (HCFO), such as 1233zd.
    Type: Application
    Filed: September 1, 2010
    Publication date: July 5, 2012
    Applicant: Arkema Inc.
    Inventors: Joseph S. Costa, Benjamin Bin Chen, Philippe Bonnet
  • Patent number: 8188323
    Abstract: The present invention relates to compositions and processes of using perfluoropolyether to maintain or improve the oil return, lubrication, cooling capacity or energy efficiency of the refrigeration, air conditioning and heat transfer system.
    Type: Grant
    Filed: July 11, 2007
    Date of Patent: May 29, 2012
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Thomas J. Leck, Thomas Frank Saturno, Gregory A. Bell
  • Publication number: 20120107513
    Abstract: Disclosed is a solvent composition for silicone compounds, containing 1-chloro-3,3,3-trifluoropropene, or a solvent composition for silicone compounds, containing (A) 1-chloro-3,3,3-trifluoropropene and (B) a compound made up of at least one selected from the group consisting of 1,1,2,2-tetrafluoro-1-methoxyethane, 1,1,1,3,3-pentafluorobutane, and 1,1,2,2-tetrafluoro-1-(2,2,2-trifluoroethoxy)ethane. This solvent composition has characteristics of nonflammability and low toxicity, and handling is extremely easy. Coating properties of the silicone compound become good by mixing this solvent composition and the silicone compound.
    Type: Application
    Filed: July 9, 2010
    Publication date: May 3, 2012
    Applicant: Central Glass Company, Limited
    Inventors: Ryoichi Tamai, Yasuo Hibino, Kanako Osafune
  • Publication number: 20120101177
    Abstract: The present invention relates to blowing agent compositions comprising at least one hydrochlorofluoroolefin (HCFO) used in the preparation of foamable thermoplastic compositions. The HCFOs of the present invention include, but are not limited to, 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), particularly the trans-isomer, 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), dichloro-fluorinated propenes, and mixtures thereof. The blowing agent compositions of the present invention are used with coblowing agents including carbon dioxide, atmospheric gases, hydrofluorocarbons (HFC), hydrofluoroolefins (HFO), alkanes, hydrofluoroethers (HFE), and mixtures thereof. Preferred HFCs used as coblowing agents in the present invention include, but are not limited too, 1,1,1,2-tetrafluoroethane (HFC-134a), 1,1-difluoroethane (HFC-152a), 1,1,1-trifluoroethane (HFC-143a), pentafluorethane (HFC-125), difluoromethane (HFC-32).
    Type: Application
    Filed: January 3, 2012
    Publication date: April 26, 2012
    Applicant: Arkema Inc.
    Inventors: Brett L. Van Horn, Maher Y. Elsheikh, Benjamin Bin Chen, Philippe Bonnet
  • Patent number: 8133407
    Abstract: Provided is a composition comprising (a) at least one halogenated compound selected from the group consisting of C3-C5 hydrofluoroolefin, CF3I, and combinations thereof, and (b) an effective stabilizing amount of a sesquiterpene selected from the group consisting of farnesol, farnesene, and mixtures thereof.
    Type: Grant
    Filed: May 15, 2009
    Date of Patent: March 13, 2012
    Assignee: Honeywell International Inc.
    Inventors: Gary Zyhowski, Rajiv Ratna Singh, Raymond H. Thomas, Mark W. Spatz, Roy P. Robinson, George J. Samuels, Gregory J. Shafer, Michael Van Der Puy, David P. Wilson, John L. Welch, Ronald P. Vogl, Samuel F. Yana Motta
  • Publication number: 20120053369
    Abstract: The invention is directed to a ternary azeotrope-like mixture consisting essentially of effective amounts of 1,1,1,3,3-pentafluoropropane, 1-chloro-3,3,3-trifluoropropene, and hydrogen fluoride.
    Type: Application
    Filed: November 8, 2011
    Publication date: March 1, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: RYAN HULSE, RAJIV R. SINGH, HSUEH S. TUNG, IAN SHANKLAND
  • Publication number: 20110313214
    Abstract: A subject of the invention is a compound of formula (I) XCFzR3-z in which: in which X represents a branched or linear unsaturated hydrocarbon radical having up to 5 carbon atoms, unsubstituted or substituted, R represents Cl, F, Br, I or H, Z is equal to 1, 2 or 3, and the bio-carbon content of which is at least 1%. A subject of the invention is also processes for the preparation of this compound.
    Type: Application
    Filed: July 9, 2009
    Publication date: December 22, 2011
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Patent number: 8067649
    Abstract: Disclosed is a process for producing tetrafluoropropene comprising: (a) catalytically fluorinating at least one tetrafluoropropene in a first reactor to produce HCFO-1233xf; (b) reacting said HCFO-1233xf with hydrogen fluoride in a second reactor to produce HCFC-244bb; (c) recycling at least a portion of said HCFC-244bb back to said first reactor as recycled HCFC-244bb; and (d) catalytically dehydrochlorinating said recycled HCFC-244bb in said first reactor to produce HFO-1234yf.
    Type: Grant
    Filed: May 14, 2009
    Date of Patent: November 29, 2011
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Hsueh Sung Tung
  • Patent number: 8058488
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH, comprising reacting a halofluorocarbon of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol.
    Type: Grant
    Filed: November 20, 2008
    Date of Patent: November 15, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Patent number: 8058486
    Abstract: A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising (a) providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III: CX2?CCl—CH2X??(Formula I) CX3—CCl?CH2??(Formula II) CX3—CHCl—CH2X??(Formula III) wherein X is independently selected from F, Cl, Br, and I, provided that at least one X is not fluorine; (b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct; (c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane and a second chlorine-containing byproduct; and (d) catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene.
    Type: Grant
    Filed: March 13, 2009
    Date of Patent: November 15, 2011
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Selma Bektesevic, Robert C. Johnson, Haiyou Wang
  • Publication number: 20110269861
    Abstract: Compositions and methods based on the use of fluoroalkene containing from 3 to 4 carbon atoms and at least one carbon-carbon double bond, such as HFO-1214, HFO-HFO-1233, or HFO-1354, having properties highly beneficial in foaming and blowing agent applications, articles and methods.
    Type: Application
    Filed: July 7, 2011
    Publication date: November 3, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: ROBERT C. JOHNSON, HSUEH SUNG TUNG, RAJIV RATNA SINGH, IAN SHANKLAND
  • Patent number: 8049046
    Abstract: The present invention relates to compositions and processes of using perfluoropolyether to maintain or improve the oil return, lubrication, cooling capacity, or energy efficiency of a refrigeration, air conditioning or heat transfer system.
    Type: Grant
    Filed: June 9, 2010
    Date of Patent: November 1, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Thomas J. Leck, Thomas Frank Saturno, Gregory A. Bell
  • Publication number: 20110224125
    Abstract: Disclosed are compositions and systems having utility in numerous situations, including in particular solvent cleaning systems, as well as refrigerant lubricants and/or compatibilizing agents, and to methods which utilize such compositions and systems. More particularly, the present invention in preferred aspects is directed to solvents, blowing agents, heat transfer fluids and compatibilizing agents comprising the compound 3-chloro-1,1,1,6,6,6-hexafluoro-2,4-hexadiene.
    Type: Application
    Filed: March 12, 2010
    Publication date: September 15, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert Johnson, Hsueh Sung Tung