Patents Represented by Attorney, Agent or Law Firm E. E. Spielman, Jr.
  • Patent number: 6110387
    Abstract: This invention describes a method for stabilizing bromine biocides in water. A water-soluble bromide salt and a sulfamate source are added to a body of water, and then an oxidant is added to the body of water to form the biocidal bromine species.
    Type: Grant
    Filed: April 22, 1999
    Date of Patent: August 29, 2000
    Assignee: Albemarle Corporation
    Inventors: Pranab Choudhury, Robert L. Davis, Michael J. Sanders, David N. Roark
  • Patent number: 6103926
    Abstract: Direct preparation of benzylically halogenated alkylbenzoic acid ester from an alkylbenzoic acid ester in which the alkyl group is a primary or secondary alkyl group is carried out. The ester group of the starting ester (i) is devoid of non-aromatic unsaturation and (ii) if an aromatic group, is devoid of ring substitution that would undergo benzylic halogenation. The process comprises slowly feeding halogen continuously and/or intermittently to an agitated solution of the alkylbenzoic acid ester in a liquid halogen-containing solvent maintained at a thermal halogenation temperature such that when the alkyl group of the alkylbenzoic acid ester is a primary alkyl group and monohalogenation is desired, the total amount of halogen fed does not exceed about 0.8 mole of halogen per mole of alkylbenzoic acid ester. If the alkylbenzoic acid ester is a toluic acid ester and dihalogenation is desired, the amount of halogen fed is over 1 mole but no more than about 1.8 moles per mole of the toluic acid ester.
    Type: Grant
    Filed: March 12, 1999
    Date of Patent: August 15, 2000
    Assignee: Albemarle Corporation
    Inventor: Hassan Y. Elnagar
  • Patent number: 6096680
    Abstract: Liquid clathrate compositions useful as reusable aluminum catalysts in Friedel-Crafts reactions are described. In one embodiment, the liquid clathrate composition is formed from constituents comprising (i) at least one aluminum trihalide, (ii) at least one salt selected from alkali metal halide, alkaline earth metal halide, alkali metal pseudohalide, quaternary ammonium salt, quaternary phosphonium salt, or ternary sulfonium salt, or a mixture of any two or more of the foregoing, and (iii) at least one aromatic hydrocarbon compound.
    Type: Grant
    Filed: April 22, 1998
    Date of Patent: August 1, 2000
    Assignee: Albemarle Corporation
    Inventor: Won S. Park
  • Patent number: 6086746
    Abstract: Operating efficiency of an electrobromination device providing disinfectant to an aqueous medium such as a swimming pool, spa, or water-cooled refrigeration unit is achieved by passing electric current across an undivided cell through which is flowing an aqueous medium containing bromide ions and a nitrogen-containing electrobromination-enhancing adjuvant such that bromide ions are electrolytically oxidized to bromine in the aqueous medium under conditions enabling formation in situ of hypobromous acid, dissociated hypobromous acid, or both.
    Type: Grant
    Filed: March 27, 1998
    Date of Patent: July 11, 2000
    Assignee: Albemarle Corporation
    Inventor: Christopher J. Nalepa
  • Patent number: 6084137
    Abstract: This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features the addition of bisphenol-A to a reaction mass containing unreacted Br.sub.2 and 30 to 85 wt. % water and an alcohol solvent, the reaction mass being at a relatively high temperature.
    Type: Grant
    Filed: October 21, 1997
    Date of Patent: July 4, 2000
    Assignee: Albemarle Corporation
    Inventors: Bonnie G. McKinnie, Richard A. Holub, Hassan Y. Elnagar
  • Patent number: 6084136
    Abstract: This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features: (a) feeding to a reaction mass (i) bisphenol-A and (ii) a stream of gaseous bromine, the gaseous stream having a Reynold's No. .gtoreq.40,000; (b) the reaction mass containing from about 50 to about 20,000 ppm unreacted bromine and less than 20 wt % HBr; and (c) the reaction mass having precipitated therefrom tetrabromobisphenol-A, all of (a)(ii), (b) and (c) occurring during the bisphenol-A feed.
    Type: Grant
    Filed: June 11, 1998
    Date of Patent: July 4, 2000
    Assignee: Albmarle Corporation
    Inventors: Richard A. Holub, Steven R. Alferi, Bonnie G. McKinnie, Hassan Y. Elnagar
  • Patent number: 6080889
    Abstract: Exothermic oxidation of tertiary amine with aqueous hydrogen peroxide in an aqueous reaction medium formed or being formed from tertiary amine, aqueous hydrogen peroxide, carbon dioxide, and optionally chelating agent and/or additional water, is initiated at about 15 to about 25.degree. C., and while agitating the reaction mixture, the temperature is allowed to rise adiabatically to a temperature in the range of about 50 to about 100.degree. C. In this way, it is possible to produce tertiary amine oxides with very low levels, if any, of nitrosamine impurity, without addition of metal and/or phosphorus-containing components recommended in the prior art. Even though a substantial portion of the reaction is performed at temperatures in the range of about 50-100.degree. C., nitrosamine content, if any, in the resultant tertiary amine oxide product can be well below 30 ppb.
    Type: Grant
    Filed: April 1, 1998
    Date of Patent: June 27, 2000
    Assignee: Albemarle Corporation
    Inventors: Rebecca S. Cochran, Andrea P. Wight, Douglas H. Krzystowczyk, Dustin H. Thomas
  • Patent number: 6068861
    Abstract: Described is a process of producing a concentrated liquid biocide formulation. Mixed together are (a) bromine chloride or bromine and (b) an aqueous solution of alkali metal salt of sulfamic acid having a pH of at least about 7, in amounts such that (i) the active bromine content of the solution is at least about 100,000 ppm (wt/wt), and (ii) the atom ratio of nitrogen to active bromine from (a) and (b) is greater than 1 when bromine is used and is greater than 0.93 when bromine chloride is used. Use of bromine chloride as the source of the active bromine in the process is preferred because in the resulting aqueous compositions, all of the bromine of the bromine chloride is made available as active bromine in solution. In other words, the chlorine of the bromine chloride is converted in the process to dissolved alkali metal chloride salt, thereby liberating all of the bromine as the active bromine content of the biocidal composition.
    Type: Grant
    Filed: June 1, 1998
    Date of Patent: May 30, 2000
    Assignee: Albemarle Corporation
    Inventors: Robert M. Moore, Jr., Christopher J. Nalepa
  • Patent number: 6063852
    Abstract: Novel brominated polyphenylmethanes, such as poly(tetrabromobenzyl bromide), are provided in a one step process by reacting a benzyl halide and bromine in the presence of a Friedel Crafts catalyst. The brominated polyphenylmethanes can be added to flammable organic polymers to make flame retardant polymer compositions.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: May 16, 2000
    Assignee: Albermarle Corporation
    Inventor: Saadat Hussain
  • Patent number: 6037497
    Abstract: A process is described in which tertiary amine is oxidized with hydrogen peroxide in the presence of carbon dioxide until the reaction mass contains (i) about 0.5 to about 6.5%, and preferably about 1 to about 2.5%, of unreacted free amine, (ii) carbon dioxide, and (iii) unreacted hydrogen peroxide. At this point individual portions of the reaction mass are dispensed into a plurality of shipping containers, or alternatively, the reaction mass is transferred to a cooling vessel, cooled therein, and then dispensed into a plurality of shipping containers. Thereafter the reaction is allowed to slowly continue to completion at ambient temperature in the shipping containers with venting of off-gases, as required. The process makes it possible to produce amine oxides with increased plant throughput without need for additional plant reaction equipment such as glass-lined reactors, and the consequent substantial additional capital investment.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: March 14, 2000
    Assignee: Albemarle Corporation
    Inventors: Dustin H. Thomas, Douglas H. Krzystowczyk, Luc G. Six
  • Patent number: 6010996
    Abstract: A quaternary ammonium compound is combined with a water-soluble anionic surfactant having a hydrophile/lipophile balance (HLB) of 14 or above to form a biocidal/surfactant composition in which the amount of (ii) is up to 50 wt % of the total weight of these components. In the presence of water or other suitable aqueous media, such compositions appear to form a soluble charge complex. But whatever actually happens in the aqueous medium, the surfactant properties of the quaternary ammonium compound are improved without jeopardizing or impairing its germicidal properties.
    Type: Grant
    Filed: October 1, 1998
    Date of Patent: January 4, 2000
    Assignee: Albemarle Corporation
    Inventors: Patrick C. Hu, Joe D. Sauer, Deborah A. Quebedeaux, Conrad J. Langlois, Jr.
  • Patent number: 6002050
    Abstract: This invention relates to a process for the production of tetrabromobisphenol-A, which process features: a water and water miscible solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of unreacted Br.sub.2 during the feed of bisphenol-A to the reactor.
    Type: Grant
    Filed: September 8, 1998
    Date of Patent: December 14, 1999
    Assignee: Albemarle Corporation
    Inventor: Bonnie G. McKinnie
  • Patent number: 5990071
    Abstract: Silver tarnishing is inhibited when using ether stabilized, n-propyl bromide based cleaning compositions by including a small amount of an acetylenic compound in the compositions.
    Type: Grant
    Filed: June 25, 1998
    Date of Patent: November 23, 1999
    Assignee: Albemarle Corporation
    Inventor: Ronald L. Shubkin
  • Patent number: 5965731
    Abstract: In an aqueous reaction medium, phenol is brominated with bromine under conditions forming an aqueous hydrobromic acid phase and an organic phase consisting essentially of molten 2,4,6-tribromophenol. The aqueous hydrobromic acid phase and the molten 2,4,6-tribromophenol are separated from each other, and optionally the molten 2,4,6-tribromophenol is washed with an aqueous decolorizing solution. An alkali metal base and water are mixed with the 2,4,6-tribromophenol to form an alkali metal salt of tribromophenol. Then, in a mixture consisting essentially of water and at least one liquid ketone, cyanuric chloride is reacted with at least a portion of the alkali metal 2,4,6-tribromophenolate of such that tris(2,4,6-tribromophenoxy)-s-1,3,5-triazine is produced.
    Type: Grant
    Filed: September 3, 1998
    Date of Patent: October 12, 1999
    Assignee: Albemarle Corporation
    Inventors: Meng-Sheng Ao, Billie B. Dadgar, Phillip R. Beaver, Mark W. Beltz
  • Patent number: 5916978
    Abstract: This invention relates to the bromination of styrenic polymers by contacting same with a brominating agent in the presence of a bromination catalyst and, as a reaction solvent, bromochloromethane.
    Type: Grant
    Filed: March 13, 1998
    Date of Patent: June 29, 1999
    Assignee: Albemarle Corporation
    Inventors: Meng-Sheng Ao, Billie B. Dadgar, Charles H. Kolich, Donald E. Balhoff, Homer C. Lin, David R. Brackenridge, Thorsten W. Brockmann
  • Patent number: 5907069
    Abstract: In producing nabumetone or precursor thereof, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl bromide or methyl chloride, in a halogen-free liquid solvent comprising at least about 40% by weight of one or more compounds of the formula RZ where R is a hydrogen atom or an alkyl group, and Z is a hydroxyl group or a cyanide group with the proviso that if Z is a cyanide group, R is an alkyl group, and in the presence of at least one strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: May 25, 1999
    Assignee: Albemarle Corporation
    Inventors: Brian F. Becnel, Mahmood Sabahi, Kevin J. Theriot
  • Patent number: 5907063
    Abstract: Activated aromatic compounds are more economically ring brominated by reacting the compounds with a sulfoxide/HBr brominating agent while removing water from the reaction mixture. The water removal provides high conversions and yields when employing stoichiometric quantities of reactants.
    Type: Grant
    Filed: March 24, 1998
    Date of Patent: May 25, 1999
    Assignee: Albemarle Corporation
    Inventor: Kevin J. Theriot
  • Patent number: 5900512
    Abstract: An oxidation process for organic compounds employs stabilized bromine chloride solutions as the oxidizing agent. Organic compounds which contain an oxidizable moiety, such as thioanisole and triphenylphosphine, are rapidly converted to sulfoxides and phosphine oxides, respectively, without over-oxidation.
    Type: Grant
    Filed: September 11, 1997
    Date of Patent: May 4, 1999
    Assignee: Albemarle Corporation
    Inventors: Hassan Y. Elnagar, Robert L. Davis
  • Patent number: 5874619
    Abstract: Existing coloration of a liquid ring-polyalkyl-substituted aromatic primary diamine is reduced by blending into such diamine a color-reducing amount of at least one dihydrocarbylhydroxylamine. Preferably, the resultant product is stored in a closed container under an inert atmosphere.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: February 23, 1999
    Assignee: Albemarle Corporation
    Inventors: Paul L. Wiggins, Gregory H. Lambeth, William R. Brown
  • Patent number: 5874659
    Abstract: A crude bromotoluene mixture comprising at least 70 wt % of a mixture of p-bromotoluene and o-bromotoluene, and wherein the weight ratio of p-bromotoluene:o-bromotoluene is in the range of 50:50 to 99:1 is cooled to a temperature at which crystals of product enriched in p-bromotoluene are formed in a first residual mother liquor. After removing the residual mother liquor from the crystals of product enriched in p-bromotoluene, the crystals are partially melted to form a mixture of residual higher purity p-bromotoluene in the form of crystals, and a second mother liquor having a higher content of o-bromotoluene than said first residual mother liquor. This higher purity p-bromotoluene and the second mother liquor are separated from each other. The entire procedure starting with the above cooling step can be repeated as a second stage and again as a third stage each time using as the initial feed the residual higher purity p-bromotoluene that is separated from the second mother liquor of the preceding stage.
    Type: Grant
    Filed: May 13, 1998
    Date of Patent: February 23, 1999
    Assignee: Albemarle Corporation
    Inventor: Christophe-Henri Pierre Lusson