Patents Represented by Attorney Richard J. Hammond
  • 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: 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: 5910595
    Abstract: A process is disclosed for the preparation of an imidazolone and the pharmaceutically acceptable salts thereof having the formula ##STR1## wherein R1 and R2 are the same or different and are C1 to C6 alkyl, C2 to C6 alkenyl, C1 to C6 cycloalkyl, aryl either unsubstituted or substituted with at least one substituent selected from the group consisting of C1 to C6 alkyl, C1 to C6 alkoxy and halo or heteroaryl either unsubstituted or substituted with C1 to C6 alkyl or halo;or R1 and R2 taken together with the carbon atom in the imidazolone ring form a carbocyclic or heterocyclic ring having from three to seven members and is saturated or is at least mono unsaturated;R3 is C1 to C6 alkyl, C2 to C6 alkenyl, C3 to C6 cycloalkyl, aryl either unsubstituted or substituted with at least one substituent selected from the group consisting of C1 to C6 alkyl, C1 to C6 alkoxy and halo or heteroaryl either unsubstituted or substituted with C1 to C6 alkyl or halo; and A- is an anion of an organic or inorganic acid.
    Type: Grant
    Filed: June 26, 1998
    Date of Patent: June 8, 1999
    Assignee: Salsbury Chemicals, Inc.
    Inventor: J. Robert Durrwachter
  • 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: 5830763
    Abstract: A process for the preparation of organic and inorganic deuterium-tagged compounds is disclosed. The process comprises heating a deuterium oxide-solution of an organic or inorganic compound, the solution having a pH of from about 10 to about 1 to a temperature and pressure so that a supercritical reaction mass forms and one or more deuterium atoms of the deuterium oxide solvent exchanges with one or more protons of the organic or inorganic compound. After cooling the reaction solution formed from the supercritical reaction, the organic or inorganic deuterium-tagged compound is separated.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: November 3, 1998
    Inventors: Thomas Junk, W. James Catallo
  • 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: 5696310
    Abstract: A process for producing a substantially pure polyfluorinated aliphatic hydrocarbon from a crude reaction solution thereof containing unsaturated hydrocarbon and halogenated saturated and unsaturated aliphatic hydrocarbon impurities is disclosed. The process comprises, as a first step, treating said crude reaction solution with a dehydrohalogenation agent that does not substantially react with the polyfluorinated aliphatic hydrocarbon. The treatment converts the halogenated aliphatic impurities into olefinic impurities.As a second step to the process of this invention, the solution formed from the first step is further treated with an agent that transforms the olefinic hydrocarbon impurities into compounds that have a boiling point than the desired polyfluorinated aliphatic hydrocarbon. The transformed impurities are then separated from the polyfluorinated aliphatic hydrocarbon.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: December 9, 1997
    Inventors: Andrew Jackson, Randolph Kenneth Belter
  • 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: 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: 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: 5424349
    Abstract: Tertiary amides have been developed which have low volatility and good thermal stability and which are effective in stabilizing organic materials that are normally susceptible to oxidative deterioration. The novel antioxidants are tertiary amides corresponding to the formula: ##STR1## wherein R is a mono-, di-, or trivalent aromatic or saturated aliphatic hydrocarbon group containing 1-20 carbons; n is an integer of 1-3 which is equal to the valence of R; R' is phenyl, benzyl, or C.sub.1 -C.sub.6 alkyl; m is an integer of 1-3; R" is a C.sub.1 -C.sub.4 alkylene group; Z and Z' are independently selected from hydrogen and alkyl; and Q is carbonyl or sulfonyl.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: June 13, 1995
    Assignee: Albemarle Corporation
    Inventor: Vincent J. Gatto
  • Patent number: 5399747
    Abstract: A new process for preparing aryl-substituted aliphatic carboxylic acids is provided. Aryl-substituted aliphatic ether or thioether compound is reacted with carbon monoxide in aqueous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An acid such as hydrochloric acid may be added. As catalyst, a mixture of palladium or a palladium compound and a copper compound with at least one acid-stable ligand are present.
    Type: Grant
    Filed: January 27, 1994
    Date of Patent: March 21, 1995
    Assignee: Albemarle Corporation
    Inventors: Kannappan Chockalingam, Tse-Chong Wu
  • Patent number: 5399279
    Abstract: Ester oils that (1) correspond to the formula ROOC-CH.sub.2 CH.sub.2 -(ROOC-CHCH.sub.2).sub.m -C(COOR).sub.2 -(CH.sub.2 CHCOOR).sub.n -CH.sub.2 CH.sub.2 COOR in which the R's represent alkyl groups of 1-30 carbons and the sum of m and n in the molecules is an average of 0-30 and (2) have viscosities suitable for refrigeration lubricants can be given excellent miscibility with fluorohydrocarbon refrigerants, such as R-134a, when at least 10% of the R groups contain 1-4 carbons.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: March 21, 1995
    Assignee: Albemarle Corporation
    Inventors: Mahmood Sabahi, Matthew L. Hurst
  • Patent number: 5396013
    Abstract: A process for making an .alpha.-olefin oligomer comprises contacting a C.sub.6 to C.sub.20 .alpha.-olefin monomer with a catalyst which includes boron trifluoride, a protic promotor and a polyether.
    Type: Grant
    Filed: July 12, 1993
    Date of Patent: March 7, 1995
    Assignee: Albemarle Corporation
    Inventor: Kevin J. Theriot
  • Patent number: 5393806
    Abstract: An improved liquid matrix system for producing fibre-reinforced plastic components is disclosed. The system comprises (i) a liquid diglycidyl ether of a halogenated bisphenol or a mixture of liquid polyglycidyl ether bisphenols at least one of which being a polyglycidyl ether halogenated bisphenol; and (ii) a curing agent that is a sterically hindered aromatic diamine containing two primary amino groups attached to the carbon atoms in the aromatic nucleus, said carbon atoms not adjacent to each other, and at least one C.sub.1 to C.sub.6 linear or branched alkyl or thioalkyl substituent; the improvement comprising adding to said system a curing accelerator composition containing a mixture of a boron halide and an imidazole unsubstituted or substituted with at least one C.sub.1 to C.sub.6 linear or branched alkyl or C.sub.6 to C.sub.10 aryl.
    Type: Grant
    Filed: December 26, 1991
    Date of Patent: February 28, 1995
    Assignee: Albemarle Corporation
    Inventor: Farah D. Azarnia