Three Or More Halogens Bonded Directly To The Ring Patents (Class 568/776)
  • Patent number: 7935853
    Abstract: A composition comprising a 2,4,-disubstituted phenol derivative in its micronized form and its use in the treatment of leukotriene-mediated diseases, gastrointestinal-inflammatory diseases or pulmonary fibrosis. More particularly, 2,4,6-triiodophenol can be used for the treatment of pulmonary fibrosis and arthritis.
    Type: Grant
    Filed: October 8, 2009
    Date of Patent: May 3, 2011
    Assignee: Bobelium S.L.
    Inventors: José Antonio Matji Tuduri, Juan Lopez Belmonte Pascual
  • Patent number: 7696389
    Abstract: A method for reducing contaminants during synthesis of pentachlorophenol includes providing a phenol-based starting material and a catalyst, which form a reaction mixture. A chlorine flow is introduced so that it is in contact with the reaction mixture, and the starting material and chlorine are reacted via a temperature-programmed reaction. The chlorine flow is terminated at a predetermined temperature prior to an end of the temperature-programmed reaction and/or at a point where the yield of pentachlorophenol is less than about 95%.
    Type: Grant
    Filed: October 31, 2008
    Date of Patent: April 13, 2010
    Assignee: The Regents of The University of Michigan
    Inventors: Phillip E. Savage, Jianli Yu
  • Publication number: 20090054699
    Abstract: A method for reducing contaminants during synthesis of pentachlorophenol includes providing a phenol-based starting material and a catalyst, which form a reaction mixture. A chlorine flow is introduced so that it is in contact with the reaction mixture, and the starting material and chlorine are reacted via a temperature-programmed reaction. The chlorine flow is terminated at a predetermined temperature prior to an end of the temperature-programmed reaction and/or at a point where the yield of pentachlorophenol is less than about 95%.
    Type: Application
    Filed: October 31, 2008
    Publication date: February 26, 2009
    Inventors: Phillip E. Savage, Jianli Yu
  • Patent number: 7446235
    Abstract: A method for reducing contaminants during synthesis of pentachlorophenol includes providing a phenol-based starting material and a catalyst, which form a reaction mixture. A chlorine flow is introduced so that it is in contact with the reaction mixture, and the starting material and chlorine are reacted via a temperature-programmed reaction. The chlorine flow is terminated at a predetermined temperature prior to an end of the temperature-programmed reaction and/or at a point where the yield of pentachlorophenol is less than about 95%.
    Type: Grant
    Filed: March 24, 2006
    Date of Patent: November 4, 2008
    Assignee: The Regents of The University of Michigan
    Inventors: Phillip E. Savage, Jianli Yu
  • Patent number: 6740253
    Abstract: The present invention relates to a non-hazardous brominating reagent from an aqueous alkaline bromine byproduct solution obtained from bromine recovery plant and containing 25 to 35% bromine dissolved in aqueous lime or sodium hydroxide containing alkali bromide and alkali bromate mixture having bromide to bromate stoichiometric ratio in the range of 5:1 to 5.1:1 or 2:1 to 2.1:1 and a pH ranging between 8-12 and also relates to a method for borminating aromatic compounds by using the above brominating agent.
    Type: Grant
    Filed: January 23, 2002
    Date of Patent: May 25, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Rajinder Nath Vohra, Pushpito Kumar Ghosh, Maheshkumar Ramniklal Gandhi, Himanshu Labhshanker Joshi, Hasina Hajibhai Deraiya, Rohit Harshadray Dave, Koushik Halder, Kishorkumar Manmohandas Majeethia, Sohan Lal Daga, Vadakke Puthoor Mohandas, Rahul Jasvantrai Sanghavi
  • Patent number: 6313355
    Abstract: Tetrabromobisphenol-A is produced in a bromination process where no bromine or only a very small proportion of bromine is fed to the reactor. In the process aqueous hydrobromic acid, is the sole source or a major source of the bromine. In the process there are at least three concurrent continuous feeds to the reactor. One is composed of bisphenol-A and/or underbrominated bisphenol-A and a water-miscible organic solvent. The second is gaseous hydrogen bromide or preferably, aqueous hydrobromic acid, and the third is aqueous hydrogen peroxide. Optionally a small additional continuous feed of bromine can be employed. The feeds are proportioned to maintain a liquid phase containing (i) from above about 15 to about 85 wt % water, based upon the amount of water and water-miscible organic solvent in such liquid phase, and (ii) an amount of unreacted bromine that is in excess over the stoichiometric amount theoretically required to convert the bisphenol-A and/or underbrominated bisphenol-A to tetrabromobisphenol-A.
    Type: Grant
    Filed: July 12, 2000
    Date of Patent: November 6, 2001
    Inventors: Thanikavelu Manimaran, Richard A. Holub, Randall S. Barton
  • 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: 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: 5849959
    Abstract: The present invention relates to compounds of the formula (1) ##STR1## where R is H, a straight-chain or branched alkyl radical with 1 to 6 carbons, a fluorinated straight-chain or branched alkyl radical with 1 to 6 carbons, a benzyl radical, or a benzyl radical substituted by an alkyl group or alkoxy group with 1 to 4 carbons each, or by halogen, X is H, Cl, Br or I, and X is different from R, and a process for their preparation.
    Type: Grant
    Filed: December 11, 1996
    Date of Patent: December 15, 1998
    Assignee: Clariant GmbH
    Inventors: Ralf Pfirmann, Rainer Wingen
  • Patent number: 5696302
    Abstract: A highly concentrated aqueous tribromophenolate solution containing a non-hydrophillic solvent and a reducing agent is prepared by dissolving an alkali and a reducing agent in water, adding a non-hydropillic solvent and adding tribromophenol.
    Type: Grant
    Filed: December 27, 1995
    Date of Patent: December 9, 1997
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Setsuo Nishibori, Hideto Kondo
  • Patent number: 5446212
    Abstract: A reduced methyl bromide process for making tetrabromobisphenol A in methanol, including: dissolving bisphenol-A in a methanol solvent to form a bisphenol-A methanol solution, adding bromine to the bisphenol-A methanol solution to brominate bisphenol-A and form tetrabromobisphenol A and hydrogen bromide, exposing the bisphenol-A methanol solution to an amount of a hydrogen peroxide agent to reduce the amount of methyl bromide co-product resulting from the bromination of bisphenol-A in methanol by reducing the amount of hydrogen bromide co-product available to react with the methanol, and collecting the resulting tetrabromobisphenol A product thus formed after the bromination is substantially complete.
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: August 29, 1995
    Assignee: Great Lakes Chemical Corp.
    Inventors: Dave C. Sanders, Arthur G. Mack, Larry D. Timberlake
  • Patent number: 5283375
    Abstract: This invention relates to a process for preparing a flame retardant product predominant in tetrabromobisphenol-A. The process comprises: (a) dissolving bisphenol-A in a methanol solvent containing up to about 5 weight percent water, wherein the ratio of methanol to bisphenol-A ranges from about 25 to about 43 moles of methanol per mole of bisphenol-A based on the total amount of methanol used and the total amount of bisphenol-A to be brominated; (b) adding to the solution in (a) from about 3.9 to about 4.2 moles of bromine per mole of bisphenol-A to be brominated while maintaining a reaction temperature in the range of from about 0.degree. to about 40.degree. C.; (c) after the bromination is substantially complete, adding water to precipitate the tetrabromobisphenol-A thus formed; and (d) purifying the precipitated tetrabromobisphenol-A so as to obtain a product predominant in tetrabromobisphenol-A containing less than about 20 ppm total ionic impurity.
    Type: Grant
    Filed: December 15, 1992
    Date of Patent: February 1, 1994
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Gary L. Sharp, Robert E. Williams
  • Patent number: 5177268
    Abstract: A process for hydrodehalogenating halogenated aromatics present in a contaminated aqueous environmental source in which the halogenated aromatics are reacted with hydrogen gas or a source of hydrogen gas in the presence of a basic proton acceptor and a catalyst of palladium on carbon.
    Type: Grant
    Filed: April 6, 1992
    Date of Patent: January 5, 1993
    Assignee: Engelhard Corporation
    Inventors: Edward N. Balko, Jeffrey B. Hoke, Gary A. Gramiccioni
  • Patent number: 5026926
    Abstract: The polychlorophenols, e.g., 2,6-dichlorophenol (a known agrochemical intermediate), are effectively prepared by chlorinating ortho-chlorophenol with gaseous chlorine, optionally in the presence of other chlorophenols, characteristically in the molten state, and in the presence of a catalytically effective amount of a primary, secondary or tertiary amine.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: June 25, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Claude Leblanc, Serge Ratton, Bernard Besson, Jean-Roger Desmurs
  • Patent number: 5017728
    Abstract: Tetrabromobisphenol-A is made in high purity and increased yield by adding a methanol-bromine solution to a methanol bisphenol-A solution with vigorous agitation. The amount of methanol in the reaction vessel is adjusted to yield a ratio of tetrabromobisphenol-A to methanol when the reaction is substantially complete that provides a lower amount of Hbr impurity in the tetrabromobisphenol-A product. An increased recovery of tetrabromobisphenol-A product is achieved by adjusting the water added to the reaction vessel when the bromination reaction is essentially complete.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: May 21, 1991
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Daniel A. Wood
  • Patent number: 4954662
    Abstract: Ortho-substituted phenolic compounds, e.g., 2,6-dichlorophenol, are selectively chlorinated, e.g., into 2,4,6-trichlorophenol, with gaseous chlorine in either the molten state or in a solvent medium, in the presence of a selectivity-enhancing effective amount of an organic cation.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: September 4, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Bernard Besson, Isabelle Jouve
  • Patent number: 4927956
    Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.
    Type: Grant
    Filed: June 2, 1989
    Date of Patent: May 22, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 4885408
    Abstract: The ortho-substituted phenols, e.g., 2,6-dichlorophenol, are reacted with gaseous chlorine, in the presence of a catalytically effective amount of a strong or Lewis acid, to produce, e.g., a more pure 2,4,6-trichlorophenol in good yield.
    Type: Grant
    Filed: July 2, 1987
    Date of Patent: December 5, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Serge Ratton, Jean-Roger Desmurs
  • Patent number: 4855513
    Abstract: The chlorophenols, e.g., 2,4,6-trichlorophenol, are efficiently prepared by chlorinating an ortho-/para-substituted phenolic compound with gaseous chlorine, whether in molten state or in a solvent reaction medium, in the presence of a catalytically effective amount of a primary, secondary or tertiary amine.
    Type: Grant
    Filed: March 7, 1988
    Date of Patent: August 8, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Bernard Besson, Jean-Roger Desmurs, Isabelle Jouve
  • Patent number: 4783556
    Abstract: Tetrabromobisphenol-A is made in high purity by adding a methanol-bromine solution to a methanol-bisphenol-A solution with vigorous agitation. Use of the bromine-methanol solution reduces the amount of by-products compared to the use of liquid bromine feed to a methanol-bisphenol-A solution. The process is readily adapted to large scale equipment by circulating the reaction mixture from the reaction vessel through an external closed loop which includes an impingement mixer. The bromine-methanol feed is pumped at the proper rate and ratio into the impingement mixture whereby it impinges with the circulating reaction mixture. The resultant bromination mixture is then returned to the reaction vessel.
    Type: Grant
    Filed: November 27, 1987
    Date of Patent: November 8, 1988
    Assignee: Ethyl Corporation
    Inventors: Olan W. Mitchell, Bonnie G. McKinnie
  • Patent number: 4740629
    Abstract: A process for partially brominating non-condensing ring aromatics (e.g. diphenyl ether) in the absence of a solvent by adding the polyaromatic to a stoichiometric excess of liquid bromine containing a zirconium halide catalyst. Product containing three bromine atoms per benzene ring (e.g., hexabromodiphenyl ether) is formed in high selectivity by keeping the reaction mixture below a threshold temperature at which higher bromine substitution occurs.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: April 26, 1988
    Assignee: Ethyl Corporation
    Inventors: David R. Brackenridge, Bonnie G. McKinnie
  • Patent number: 4670610
    Abstract: 2,5-Dichlorophenol is readily and facilely prepared from 2,5-dichloro-4-hydroxybenzenesulfonic acid or salt thereof, said sulfonic acid/sulfonate itself being characteristically produced by hydrolysis of a precursor trichlorobenzenesulfonic acid, by cleaving the sulfo/sulfonate moiety therefrom by treatment, e.g., under reflux, with a constant boiling point hydrobromic acid.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: June 2, 1987
    Assignee: Sandoz, Inc.
    Inventor: Richard H. Sehring
  • Patent number: 4564714
    Abstract: A novel process for the preparation of 2,4,5-trichlorophenol which comprises selectively chlorinating 2,5-dichlorophenol under acidic conditions.
    Type: Grant
    Filed: October 30, 1984
    Date of Patent: January 14, 1986
    Assignee: Givaudan Corporation
    Inventors: Joseph A. Virgilio, Joachim E. Freudewald
  • Patent number: 4431847
    Abstract: A process for forming a substantially insoluble solid polymer from halogeneated phenolic compounds dissolved in a liquid medium using an oxidizing agent. NaOCl and NaOBr are used as oxidizing agents to initiate the polymerization reaction among the halogenated phenolic compounds. The polymer precipitates from the system to form a claylike solid. The solid is environmentally safe and may be disposed of in a sanitary landfill.
    Type: Grant
    Filed: July 29, 1982
    Date of Patent: February 14, 1984
    Assignee: Ethyl Corporation
    Inventors: Joseph A. Bossier, Julio J. Vega
  • Patent number: 4400556
    Abstract: The invention covers the use of novel co-catalysts as inhibitors that reduce the formation of undesirable chlorinated dioxins during the preparation of pentachlorophenol and tetrachlorophenol from phenol or lower chlorinated phenols.
    Type: Grant
    Filed: June 22, 1981
    Date of Patent: August 23, 1983
    Assignee: Reichhold Chemicals, Incorporated
    Inventors: William H. Wetzel, Hsi-Lung Pan, Robert J. Goodwin, John E. Wilkinson
  • Patent number: 4376220
    Abstract: The invention covers the use of novel co-catalysts as inhibitors that reduce the formation of undesirable chlorinated dioxins during the preparation of pentachlorophenol and tetrachlorophenol from phenol or lower chlorinated phenols.
    Type: Grant
    Filed: June 22, 1981
    Date of Patent: March 8, 1983
    Assignee: Reichhold Chemicals, Incorporated
    Inventors: William H. Wetzel, Hsi-Lung Pan, Robert J. Goodwin, John E. Wilkinson
  • Patent number: 4346248
    Abstract: A process for the preparation of 2,4,5-trichlorophenol and 2,4,5-trichlorophenoxyacetic acid free of 2,3,7,8-tetrachloro-dibenzo-p-dioxin contamination by the steps of nitrating 1,2,4-trichlorobenzene, reducing the resulting 1,2,4-trichloro-5-nitrobenzene, diazotizing the resulting 2,4,5-trichloroaniline, hydrolyzing the resulting 2,4,5-trichlorobenzenediazonium salt and recovering 2,4,5-trichlorophenol. The 2,4,5-trichlorophenol is reacted with monochloroacetic acid to give 2,4,5-trichlorophenoxyacetic acid. Both the 2,4,5-trichlorophenol and the 2,4,5-trichlorophenoxyacetic acid produced by the process are analytically free of 2,3,7,8-tetrachloro-dibenzo-p-dioxin in analytical tests sensitive to 1 part per billion.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: August 24, 1982
    Assignee: Vertac Chemical Corporation
    Inventors: Dennis L. Deavenport, Kenneth J. Howard, Albert E. Sidwell
  • Patent number: 4345097
    Abstract: The process for the chlorination of aromatic compounds of the formula: ##STR1## wherein R is a member selected from the group consisting of hydrogen, carboxymethyl, and carboxyethyl and R.sub.x is a member selected from the group consisting of hydrogen, 2-methyl, 2,5-dichloro, and 2-chloro, with the proviso that when R is hydrogen, R.sub.x is 2,5-dichloro, consisting of reacting said aromatic compound with sulfuryl chloride in the presence of elemental sulfur or certain sulfur compounds as a catalyst, optionally together with the presence of a Friedel-Crafts acid catalyst and/or an inert organic solvent at temperatures of from 30.degree. C. to 150.degree. C., and recovering a para chlorinated compound.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: August 17, 1982
    Assignee: Vertac Chemical Corporation
    Inventors: Kenneth J. Howard, Albert E. Sidwell
  • Patent number: 4306098
    Abstract: A method of producing 2,4,5-trichlorophenol with low levels of the impurity 2,3,7,8-tetrachlorodibenzo-.rho.-dioxin.
    Type: Grant
    Filed: July 7, 1980
    Date of Patent: December 15, 1981
    Assignee: Ivon Watkins-Dow Limited
    Inventor: Edgar G. Brooker
  • Patent number: 4294996
    Abstract: The invention covers the use of novel co-catalysts as inhibitors that reduce the formation of undesirable chlorinated dioxins during the preparation of pentachlorophenol and tetrachlorophenol from phenol or lower chlorinated phenols.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: October 13, 1981
    Assignee: Reichhold Chemicals, Incorporated
    Inventors: William H. Wetzel, Hsi-Lung Pan, Robert J. Goodwin, John E. Wilkinson
  • Patent number: 4289587
    Abstract: Chlorinated phenols, e.g. pentachlorophenol, are stabilized against degradation, including degradation to chlorinated dibenzo-p-dioxins, caused by heat and other adverse conditions, by combining with them stabilizing amounts of at least one stabilizer selected from the group consisting of high-boiling epoxides and epoxidized oils, drying oils, unsaturated fatty acids and unsaturated esters of fatty acids.
    Type: Grant
    Filed: April 29, 1980
    Date of Patent: September 15, 1981
    Assignee: Vulcan Materials Company
    Inventor: Ray C. Christena
  • Patent number: 4287373
    Abstract: A process for the perbromination of phenol and diphenyl ether by brominating the corresponding compound in bromine as the sole reaction medium using metal and metal-containing catalysts at an elevated initial reaction temperature of at least about 35.degree. C., preferably at least about 45.degree. C., substantially enhances reaction productivity without adversely affecting product yield or quality.
    Type: Grant
    Filed: October 1, 1979
    Date of Patent: September 1, 1981
    Assignee: Great Lakes Chemical Corporation
    Inventors: John A. Garman, Rastko I. Mamuzic, Robert B. McDonald, John L. Sands, Gregory Thompson
  • Patent number: 4272636
    Abstract: In an improved process for preparing chlorinated phenol by the reaction of molten phenol with chlorine in the presence of a Friedel-Crafts catalyst, the improvement comprises adding to the molten chlorinated phenol product, immediately on completion of the chlorination process, at least 0.5 weight percent of a glycol ether thereby inhibiting dioxin formation, inhibiting decomposition of the technical grade chlorinated phenol and most importantly, imparting mold release properties to the final product which is cast in corrosion-resistant molds, preferably stainless steel or plastic-lined steel molds.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: June 9, 1981
    Assignee: The Dow Chemical Company
    Inventors: Leonard R. Thompson, J. Kevin Kearney
  • Patent number: 4272635
    Abstract: A molten substituted phenol and an aqueous caustic solution are reacted at temperatures from 170.degree. C. to 190.degree. C. under superatmospheric pressure to form an aqueous solution of an alkali metal phenate. By employing a rapid drying process such as flashing the water vapor from the reactor to cool the mixture, alkali metal phenate solids are produced with low levels of toxic by-products.
    Type: Grant
    Filed: July 26, 1979
    Date of Patent: June 9, 1981
    Assignee: The Dow Chemical Company
    Inventors: Sanford A. Siegel, Masao Yoshimine, Che-I Kao
  • Patent number: 4255593
    Abstract: In the process for the manufacture of salts of halogenated phenols the economy is improved and health and pollution hazards are reduced by mixing an alkaline agent and the halogenated phenol with a small amount of a liquid medium that is solvent for the alkaline agent, conducting a reaction between the components in a closed system until a dry or almost dry product is obtained, agitating the mixture during at least a part of the liquid medium removal step and discharging the product in particulate form from the closed system.
    Type: Grant
    Filed: February 21, 1980
    Date of Patent: March 10, 1981
    Assignee: Chapman Chemical Company
    Inventor: Fritz J. Nagel
  • Patent number: 4246188
    Abstract: Aryl sulfonic acid esters of the formula ##STR1## wherein R.sup.1 represents hydrogen, alkyl groups of 1 to 8 carbon atoms, bromine or chlorine, R.sup.2 represents R.sup.1 or the group ##STR2## Hal represents bromine or chlorine, x the numbers 2 to 4, n the numbers 3 to 5, y the numbers 4-x; m=5-n, R.sup.3 represents bromine, chlorine or the group ##STR3## and Z represents --O--, --S--, ##STR4## alkylene with 1 to 4 carbon atoms, or alkylidene; a process for their product and their use as a flame retardant, especially for polyolefins.
    Type: Grant
    Filed: October 2, 1978
    Date of Patent: January 20, 1981
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Egon N. Peterson, Hermann Richtzenhain
  • Patent number: 4237321
    Abstract: A method of making 2,4,5-trichlorophenol by chlorinating 2,5-dichlorophenol is characterized by reacting 2,5-dichlorophenol with chlorine in the presence of a liquid inert polar aprotic reaction medium such as nitrobenzene or a chlorinated hydrocarbon reaction medium, particularly 1,2-dichloroethane, and preferable a Lewis acid catalyst, particularly aluminium chloride. The product contains a higher ratio of 2,4,5-trichlorophenol to 2,3,6-trichlorophenol than has been obtainable previously.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: December 2, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Eric Cuthbertson
  • Patent number: 4216342
    Abstract: A novel process for the purification of 2,4,5-trichlorophenol which comprises selectively reacting the major impurities with formaldehyde.
    Type: Grant
    Filed: March 30, 1979
    Date of Patent: August 5, 1980
    Assignee: Givaudan Corporation
    Inventors: Joseph A. Virgilio, Joachim E. Freudewald
  • Patent number: 4196132
    Abstract: 3,4,5,6-Tetrachloro-3,5-cyclohexadiene-1,2-dione (o-chloranil), a valuable organic oxidant used particularly in the photographic industry, has now been found to be synthesizable by an improved, continuous flow process from catechol.
    Type: Grant
    Filed: August 11, 1978
    Date of Patent: April 1, 1980
    Assignee: The Upjohn Company
    Inventors: Fredric G. Bader, Howard J. Burke
  • Patent number: 4160114
    Abstract: In a process for producing relatively pure commercially acceptable pentachlorophenol, comprising reacting, at a temperature ranging from about 10.degree. to about 190.degree. C., (A) a phenol consisting essentially of raw or commercial phenol which may contain, as impurities from other processes, some lower chlorophenols such as mono and dichlorophenols and mixtures thereof, and (B) chlorine, in the presence of (C) an acid catalyst from about 0.005 moles to about 0.
    Type: Grant
    Filed: July 20, 1977
    Date of Patent: July 3, 1979
    Assignee: Reichhold Chemicals, Inc.
    Inventors: Frederic J. Shelton, William H. Wetzel, John E. Wilkinson, Robert J. Goodwin
  • Patent number: 4160112
    Abstract: A process for isolating crude pentabromophenol containing occluded bromine and hydrogen bromide as impurities comprising the steps of contacting the crude pentabromophenol with a strong acid such as hydrobromic acid, sulfuric acid, hydrochloric acid and phosphoric acid; heating the mixture in order to remove excess bromine; and recovering of the pentabromophenol, whereby formation of carbonyl-group-containing impurities during isolation is minimized.
    Type: Grant
    Filed: February 13, 1978
    Date of Patent: July 3, 1979
    Assignee: Great Lakes Chemical Corporation
    Inventors: Robert P. Levek, Rastko I. Mamuzic, John L. Sands