Patents Assigned to LaRoche Industries, Inc.
  • Patent number: 6063970
    Abstract: A process is disclosed for the preparation of a chlorofluoro aliphatic hydrocarbon having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.c Cl .sub.3-c-b F.sub.bwherein a and c are 0 or the integer 1 or 2 and b is the integer 1, 2 or 3. The process comprises reacting a chlorinated fluoroolefinic hydrocarbon of the formulaCH.sub.a F.sub.3-a --CH.dbd.CH.sub.c Cl.sub.2-cwherein a and c are as previously described, with anhydrous hydrogen fluoride and a is as described previously. This reaction is catalyzed with a compound that is a metal oxide or metal halide. The metallic part of such compound is arsenic, antimony, tin, boron or is selected from a metal in Group IVb, Vb, VIb, VIIb or VIIIb of the Periodic Table of the Elements. The desired chlorofluoro aliphatic hydrocarbon is then recovered.
    Type: Grant
    Filed: October 8, 1998
    Date of Patent: May 16, 2000
    Assignee: Laroche Industries, Inc.
    Inventors: C. Bradford Boyce, Randolph K. Belter, Terry Parker
  • Patent number: 6034016
    Abstract: A method for removing high molecular weight solid and liquid tars and oligomers from halogenated Lewis acids catalysts is disclosed. The Lewis acids incorporating such tars and oligomers are treated with an oxidizing agent such as chlorine, a halogen fluoride or mixtures thereof for a time and at a temperature sufficient to oxidize said solid tars and oligomers. The oxidation causes such tars and oligomers to form oxidation products, which can be separated from the halogenated Lewis acid.
    Type: Grant
    Filed: May 8, 1998
    Date of Patent: March 7, 2000
    Assignee: LaRoche Industries Inc.
    Inventors: C. Bradford Boyce, Randolph K. Belter
  • Patent number: 6013600
    Abstract: A method of producing activated alumina bodies having alkali or alkaline earth metal compounds incorporated therein, the bodies suitable for adsorption and having increased capacity for adsorption of gases and the like. The method comprises providing a source of activated alumina powder and further providing an aqueous solution having an alkali or alkaline earth metal hydroxide and a water soluble alkali or alkaline earth metal salt of an organic compound dissolved therein. The activated alumina powder is formed into bodies which are treated with the aqueous solution to provide alumina bodies having alkali or alkaline earth metal compounds incorporated therein. The alumina bodies are heated for purposes of activation to provide said activated alumina bodies capable of having increased adsorption capacity.
    Type: Grant
    Filed: May 23, 1997
    Date of Patent: January 11, 2000
    Assignee: LaRoche Industries Inc.
    Inventor: Vladislav I. Kanazirev
  • Patent number: 5981814
    Abstract: A process is disclosed for the preparation of a fluorinated aliphatic hydrocarbon having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-bwherein a is 0 or the integer 1 or 2 and b is 0 or the integer 1, 2 or 3. The reaction occurs in the vapor phase. A chlorofluoro olefin of the formulaCH.sub.c Cl.sub.2-c .dbd.CH--CH.sub.d F.sub.3--dwherein c is 0 or the integer 1 or 2, and d is 0 or the integer 1 or 2 is treated in the vapor phase with hydrogen fluoride. This treating is catalyzed with a compound that is a metal oxide, a metal halide or a mixture thereof. The metallic part of such compound is selected from a metal in Group IIIa, IIIb, IVa, Va, IVb, Vb, VIa, VIb, VIIb and VIII of the Periodic Table of the Elements. The treating is carried out for a time sufficient to form the desired fluorinated aliphatic hydrocarbon which is subsequently recovered from the vapor phase reaction.The process is particularly suitable for the preparation of 1,1,1,3,3-pentafluoropropane.
    Type: Grant
    Filed: March 23, 1998
    Date of Patent: November 9, 1999
    Assignee: LaRoche Industries Inc.
    Inventors: C. Bradford Boyce, Randolph K. Belter
  • Patent number: 5973215
    Abstract: A process is disclosed for the liquid phase separation and recovery of hydrogen fluoride from a mixture comprising hydrogen fluoride and a fluorinated organic hydrocarbon. The process requires that the mixture be treated with a sufficient amount of a coupled phase-separating agent comprising an organic or inorganic salt, an alkanolamine or mixtures thereof and a substituted or unsubstituted aromatic compound to form a first and a second phase. The first phase that is formed is a hydrogen fluoride-rich phase that additionally contains substantially all of said salt, said alkanolamine or mixtures thereof from the coupled phase-separating agent. The second phase comprises substantially all of said aromatic compound and the fluorinated organic hydrocarbon. It is substantially free of hydrogen fluoride. The phases are separated from each other.
    Type: Grant
    Filed: March 16, 1998
    Date of Patent: October 26, 1999
    Assignee: LaRoche Industries Inc
    Inventor: Randolph K. Belter
  • Patent number: 5944962
    Abstract: An improvement in the process for the photochlorination of liquid mixtures of 2 to 6 carbon-containing aliphatic hydrofluorohalocarbons or hydrofluorocarbons and unsaturated hydrocarbons with ultraviolet light is disclosed. The improvement comprises using ultraviolet light emitted from an ultraviolet light source that delivers from about 0.01 to about 0.10 Einsteins per inch of arc at an input power of from about 0.50 to about 4.0 watts per inch of arc at a wavelength that is substantially the same as the wavelength absorption band of chlorine.
    Type: Grant
    Filed: February 3, 1998
    Date of Patent: August 31, 1999
    Assignee: LaRoche Industries, Inc.
    Inventor: C. Bradford Boyce
  • Patent number: 5935894
    Abstract: A method of preparing an alumina-based bodies suitable for use as an adsorbent or catalyst, the method comprising providing a source of activated alumina powder for forming into bodies and providing an aqueous solution containing at least two different alkali metals, at least one alkali metal derived from a soluble carboxylic acid alkali metal salt. As said powder is formed into said bodies, the bodies are contacted or sprayed with the aqueous solution to provide composite bodies containing the alumina powder and the alkali metals and the soluble carboxylic acid alkali metal salt. Alternatively, the alumina bodies may be formed first and then contacted, e.g., soaked in the aqueous solution. Or, a viscous slurry of the activated alumina powder and the aqueous solution may be made. The viscous slurry may be made into bodies by extrusion or by the oil drop method. Thereafter, the bodies are thermally treated to activate alumina therein and remove or decompose the organic part, e.g.
    Type: Grant
    Filed: July 2, 1997
    Date of Patent: August 10, 1999
    Assignee: LaRoche Industries, Inc.
    Inventor: Vladislav I. Kanazirev
  • Patent number: 5910616
    Abstract: A process is disclosed for the preparation of a fluorinated aliphatic hydrocarbon. The process utilizes a C.sub.1 to C.sub.6 hydrocarbon substituted with a halogen selected from the group consisting of chlorine, bromine and iodine as the starting material. The alkyl hydrocarbon is reacted in the vapor phase at a temperature from about 75.degree. to about 150.degree. C. with hydrogen fluoride and a catalytically effective amount of at least one antimony compound having the formulaSb.sub.w.sup.u M.sub.x.sup.v X.sub.y F.sub.z.nHFwhere n is 0 or an integer that is at least 1; M is selected from the group consisting of a metal from Group IIIa, IIIb, IVa, IVb, Va, Vb, VIa, VIb, VIIb and VIII of the Periodic Table of the Elements; X is chloro, bromo or iodo; u is an integer that is the valence of antimony; v is an integer that is the valence of M; w, x and z are an integer of at least 1; y is 0 or an integer of at least 1; and (w.multidot.u)+(x.multidot.
    Type: Grant
    Filed: June 22, 1998
    Date of Patent: June 8, 1999
    Assignee: LaRoche Industries, Inc.
    Inventors: C. Bradford Boyce, Randolph K. Belter
  • Patent number: 5874658
    Abstract: A method is disclosed for separating a mixture of at least one hydrofluorocarbon from hydrogen fluoride. The method comprising treating said mixture with a compound selected from the group consisting of an alkanolamine of formulaNH.sub.a (CH.sub.b R.sub.c).sub.dwhere R is C.sub.1 to C.sub.6 linear or branched alkylene substituted with at least one hydroxy group, wherein a and d are the integers 1 or 2 and a+d=3 and b is 0 or the integer 1 or 2 and b+c=3, C.sub.6 to C.sub.10 aryl unsubstituted or substituted with halo or halo-substituted C.sub.1 to C.sub.6, alkyl, sulfuric acid and sulfuric acid admixed with at least one alkali metal sulfate. The hydrofluorocabon and HF form two separate phases by this treatment. The phases are readily separated.
    Type: Grant
    Filed: September 12, 1997
    Date of Patent: February 23, 1999
    Assignee: LaRoche Industries Inc.
    Inventor: Randolph K. Belter
  • Patent number: 5777185
    Abstract: A process is disclosed for hydrofluorinating an olefinic hydrocarbon of the formulaX --CX'.dbd.CX'--R'where X, X' and X" are the same or different and are hydrogen or halo and R' is hydrogen or C.sub.1 -C.sub.6 alkyl, with hydrogen fluoride. The process is carried out by admixing the olefinic hydrocarbon with hydrogen fluoride in an imidofluoride hydrogen fluoride solvent having the formulaR--(CF.dbd.NH.sub.2).sup.+ F.sup.- .multidot..eta.HFwhere R is C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkyl substituted with halo or C.sub.6 to C.sub.10 aryl either unsubstituted or substituted with alkyl and .eta. is 0 or an integer that is at least 1.
    Type: Grant
    Filed: September 9, 1997
    Date of Patent: July 7, 1998
    Assignee: LaRoche Industries Inc.
    Inventor: Randolph K. Belter
  • Patent number: 5750010
    Abstract: An improvement in the process for the photochlorination of liquid mixtures of 1,1-dichloro-1-fluoroethane and unsaturated hydrocarbons with ultraviolet light is disclosed. The improvement comprises using ultraviolet light emitted from an ultraviolet light source having an ultraviolet radiation efficiency of at least 0.01 Einsteins per inch of arc per 100 watts input at a wavelength that is substantially the same as the wavelength absorption band of chlorine.
    Type: Grant
    Filed: October 3, 1995
    Date of Patent: May 12, 1998
    Assignee: LaRoche Industries, Inc.
    Inventors: C. Bradford Boyce, Guy P. Pittman, Bolivar F. Lewis, III
  • Patent number: 5727394
    Abstract: A method of conditioning a process stream of air in an air conditioning system wherein a process stream of air is dehumidified and cooled to provide a conditioned stream of air for introducing to a conditioned space. The method comprises the steps of providing an adsorption wheel having a multiplicity of passages through which process air can flow for adsorbing moisture therefrom, the wheel capable of adsorption of moisture from the process air and of regeneration on a continuous basis as the wheel rotates. An indirect evaporative cooler is provided having a dry side and a wet side separated by a moisture-impervious wall wherein heat is extracted from said dry side through the wall to the wet side. Cooling in the dry side is achieved by evaporation of water into air passing through the wet side. The process air is passed through the adsorption wheel to remove moisture therefrom to provide a moisture-depleted stream of process air exiting the adsorption wheel.
    Type: Grant
    Filed: April 25, 1996
    Date of Patent: March 17, 1998
    Assignees: LaRoche Industries, Inc., ACMA Limited
    Inventors: William A. Belding, William D. Holeman, Chiang Lam
  • Patent number: 5696309
    Abstract: Disclosed is a method of chlorinating vinylidene chloride contained in a solution 1,1 -dichloro-1-fluoroethane to provide a chlorinated compound having a boiling point different from the 1,1-dichloro-1-fluoroethane to permit separation therefrom. The method comprises providing a solution containing 1,1-dichloro-1-fluoroethane and vinylidene chloride; introducing chlorine to the solution; and contacting the chlorine containing solution with a metal oxide to effect chlorination of the vinylidene chloride to produce one of 1,1,1,2-tetrachloroethane, trichloroethylene and pentachloroethane.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: December 9, 1997
    Assignee: LaRoche Industries, Inc.
    Inventors: Andrew Jackson, C. Bradford Boyce
  • Patent number: 5689020
    Abstract: A process is disclosed for preparing a compound selected from the group consisting of 1,1,3,3-tetrachloropropene and 1,3,3,3-tetrachloropropene. The process comprisesa. admixing a hydrocarbon compound selected from the group consisting of propene, 1-chloropropene, 3-chloropropene, 1,1-dichloropropene, 1,3-dichloropropene, 3,3,-dichloropropene, 1,1-dichloropropane, 11,2-dichloropropane, 1,3-dichloropropane, 1,1,3-trichloropropene, 1,3,3-trichloropropene, 3,3,3-trichloropropene, and mixtures thereof with an inert diluent gas;b. preheating said mixture to from about 300.degree. C. to about 400.degree. C. and then mixing it with chlorine gas; andc. thermally treating the mixture of step b. at a temperature of from about 400.degree. C. to about 600.degree. C.The desired tetrachloropropene is then separated.
    Type: Grant
    Filed: March 11, 1996
    Date of Patent: November 18, 1997
    Assignee: LaRoche Industries Inc.
    Inventor: C. Bradford Boyce
  • Patent number: 5685897
    Abstract: A sensible and latent heat exchange or adsorbent media formed from an improved desiccant or adsorbent paper having higher strength and thinner gauge to provide increased area of media, the media having a multiplicity of passageways therethrough through which an air stream can flow. The improved desiccant or adsorbent paper is comprised of fibrillated and non-fibrillated organic fibers formed to provide an improved support material having improved levels of strength and higher levels of desiccant or adsorbent material contained in the improved fibrous support material to provide the improved paper.
    Type: Grant
    Filed: November 6, 1995
    Date of Patent: November 11, 1997
    Assignee: LaRoche Industries, Inc.
    Inventors: William A. Belding, Marc P. F. Delmas, William D. Holeman, David A. McDonald
  • Patent number: 5684219
    Abstract: A process is disclosed for the preparation of a fluorinated aliphatic olefin having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-bwherein a is 0 or the integer 1 or d and b is 0 or the integer 1, 2 or 3.In the first step of the process, a chlorinated olefinic hydrocarbon of the formulaCH.sub.c Cl.sub.2-c .dbd.CH--CH.sub.d Cl.sub.3-dwherein c is 0 or the integer 1 and d is 0 or the integer 1 or 2 is reacted with anhydrous hydrogen fluoride for a period of time and at a temperature sufficient to form a chlorofluoro olefin of the formulaCH.sub.e Cl.sub.2-e .dbd.CH--CH.sub.f F.sub.3-fwherein e is 0 or the integer 1 and f is 0 or the integer 1 or 2.The chlorofluoro olefin produced in the first step is then reacted with anhydrous hydrogen fluoride in a second reaction. This second reaction is catalyzed with at least one compound that is a metal oxide or metal halide. Mixtures of said metal oxides, metal halides and metal oxides with metal halides may also be used.
    Type: Grant
    Filed: November 5, 1996
    Date of Patent: November 4, 1997
    Assignee: LaRoche Industries Inc.
    Inventors: C. Bradford Boyce, Randolph Kenneth Belter
  • Patent number: 5660048
    Abstract: A method of conditioning a process stream of air in an air conditioning system wherein a process stream of air is dehumidified and cooled to provide a conditioned stream of air for introducing to a conditioned space, the method comprises the steps of providing an enthalpy wheel comprised of an adsorbent contained in a paper web, the enthalpy wheel having a multiplicity of passages through which the process air can flow, the enthalpy wheel capable of regeneration by passing an air stream therethrough having a temperature and humidity lower than the process air. In the method, process air is passed through the enthalpy wheel to remove heat and moisture therefrom, and the enthalpy wheel is regenerated by passing air therethrough to remove heat and moisture therefrom.
    Type: Grant
    Filed: February 16, 1996
    Date of Patent: August 26, 1997
    Assignees: LaRoche Industries, Inc., ACMA Limited
    Inventors: William A. Belding, Chiang Lam, William D. Holeman, Scott L. Janke
  • Patent number: 5650221
    Abstract: A sensible and latent heat exchange or adsorbent media formed from an improved desiccant or adsorbent paper having higher strength and thinner gauge to provide increased area of media, the media having a multiplicity of passageways therethrough through which an air stream can flow. The improved desiccant or adsorbent paper is comprised of fibrillated organic fibers formed to provide an improved support material having improved levels of strength and higher levels of desiccant or adsorbent material contained in the improved fibrous support material to provide the improved paper. The improved desiccant paper is capable of adsorbing or transferring sensible heat from a warm air stream and releasing or transferring the absorbed sensible heat into a cool air stream as the air stream flows though the sensible and latent heat exchange media.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: July 22, 1997
    Assignee: LaRoche Industries, Inc.
    Inventors: William A. Belding, Marc P. F. Delmas, William D. Holeman, David A. McDonald
  • Patent number: 5616819
    Abstract: A process is disclosed for the preparation of a fluorinated aliphatic olefin having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-bwherein a is 0 or the integer 1 or 2 and b is 0 or the integer 1, 2 or 3.In the first step of the process, a chlorinated olefinic hydrocarbon of the formulaCH.sub.c Cl.sub.2-c .dbd.CH--CH.sub.d Cl.sub.3-dwherein c is 0 or the integer 1 and d is 0 or the integer 1 or 2 is reacted with anhydrous hydrogen fluoride for a period of time and at a temperature sufficient to form a chlorofluoro olefin of the formulaCH.sub.e Cl.sub.2-e .dbd.CH--CH.sub.f F.sub.3-fwherein e is 0 or the integer 1 and f is 0 or the integer 1 or 2.The chlorofluoro olefin produced in the first step is then reacted with anhydrous hydrogen fluoride in a second reaction. This second reaction is catalyzed with at least one compound that is a metal oxide or metal halide. Mixtures of said metal oxides, metal halides and metal oxides with metal halides may also be used.
    Type: Grant
    Filed: August 28, 1995
    Date of Patent: April 1, 1997
    Assignee: LaRoche Industries Inc.
    Inventors: C. Bradford Boyce, Randolph K. Belter
  • Patent number: 5580369
    Abstract: An improved adsorbent composition for a natural gas-fired, adsorption cooling system that readily adsorbs moisture from ambient air, while being readily regenerated at high temperatures up to 200.degree.-300.degree. C. in order to provide an enhanced coefficient of performance to the system. Such an adsorbent composition may comprise an A-type zeolite, an X-type zeolite or a chemically modified Y-type zeolite either alone, in conjunction with each other or in conjunction with alumina and/or silica gel. A rotating adsorbent wheel may be fashioned from corrugated paper comprising the adsorbent composition and a slurry of synthetic, organic fibers which are preferably polyaramid fibers. The strength of the wheel may be enhanced by surface treating it with sols or salt solutions of alumina or silica, and a highly temperature-stable epoxy or phenolic resin.
    Type: Grant
    Filed: January 30, 1995
    Date of Patent: December 3, 1996
    Assignee: LaRoche Industries, Inc.
    Inventors: William A. Belding, William D. Holeman, Zalman Lavan, Roger L. Jones