Halogen Containing Patents (Class 568/725)
  • Patent number: 7067704
    Abstract: Bisphenol-A is purified in a process which comprises the following steps: a) cooling a liquid mixture comprising bisphenol-A and water in a bisphenol-A crystallizer to form bisphenol-A crystals in a liquid phase; b) separating the bisphenol-A crystals from the liquid phase; c) dividing at least a portion of the liquid phase into a bisphenol-rich organic phase and a water-rich phase; d) feeding phenol and at least a portion of the bisphenol-rich organic phase into a adduct crystallizer to form a crystalline adduct of phenol and bisphenol-A in a mother liquor, and e) separating the crystalline adduct from the mother liquor. Bisphenol-A of high purity at a high yield is obtained.
    Type: Grant
    Filed: November 12, 2003
    Date of Patent: June 27, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Thomas C. Young, Damian M. Feord, Johann-Wilhelm Frey
  • Patent number: 6613947
    Abstract: A high purity 4,4′-isopropylidine-bis-(2,6-dibromophenol) characterised by ionic bromides less than 10 ppm, colour in alkaline solution from 60-100 HU, HPLC purity about 99.9%, APHA of 20% MeOH solution less than 10.0 HU, Fe less than 1.0 ppm, turbidity of 20% MeOH solution less than 5 NTU, pH of 10% slurry 6.0-7.0, size of the crystal particles, 250 to 280 microns with angle of repose lower than 30°.
    Type: Grant
    Filed: October 21, 2002
    Date of Patent: September 2, 2003
    Assignee: Solaris Chemtech Limited
    Inventors: Shantaram Narayan Naik, Dharma Ratnakar Ramdas Naik, M. Madhusudan Rao
  • Publication number: 20010049456
    Abstract: A method of crystallizing tetrabromobisphenol A is described, which comprises continuously and simultaneously feeding a methanolic tetrabromobisphenol A solution and water separately to a first crystallizer to obtain a slurry in which a part of the tetrabromobisphenol A is crystallized and continuously and simultaneously feeding said slurry and water separately to a second crystallizer to crystallize substantially the whole amount of the tetrabromophisphenol A.
    Type: Application
    Filed: May 15, 2001
    Publication date: December 6, 2001
    Inventors: Hiroshi Fushihara, Hidemasa Suetsugu, Takahiro Matsunaga
  • 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: 6300527
    Abstract: This invention relates, inter alia, to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A and/or underbrominated bisphenol-A, which process features: a water and water-miscible organic solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of both (i) excess unreacted Br2 during the feed of bisphenol-A to the reactor, and (ii) sufficient HBr to protect the tetrabromobisphenol-A produced against undesirable color formation. Tetrabromobisphenol-A precipitates from the reaction mass and is easily recovered. Product of high purity (97% or more) and very low color (APHA of 50 or less) can be produced, even when using large excesses of bromine in the reaction.
    Type: Grant
    Filed: July 12, 2000
    Date of Patent: October 9, 2001
    Assignee: Albemarle Corporation
    Inventors: Thanikavelu Manimaran, Hassan Y. Elnagar, Richard A. Holub, Alvin E. Harkins, Jr., Bonnie G. McKinnie
  • Patent number: 6235946
    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: October 12, 1999
    Date of Patent: May 22, 2001
    Assignee: Albemarle Corporation
    Inventors: Thanikavelu Manimaran, Richard A. Holub, Randall S. Barton
  • Patent number: 6218584
    Abstract: This invention relates, inter alia, to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A and/or underbrominated bisphenol-A, which process features: a water and water-miscible organic solvent reaction medium; a relatively high reaction temperature; and the presence, in the reaction medium, of both (i) excess unreacted Br2 during the feed of bis-phenol-A to the reactor, and (ii) sufficient HBr to protect the tetrabromobisphenol-A produced against undesirable color formation. Tetrabromobisphenol-A precipitates from the reaction mass and is easily recovered. Product of high purity (97% or more) and very low color (APHA of 50 or less) can be produced, even when using large excesses of bromine in the reaction.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: April 17, 2001
    Assignee: Albemarle Corporation
    Inventors: Thanikavelu Manimaran, Hassan Y. Elnagar, Richard A. Holub, Alvin E. Harkins, Jr., Bonnie G. McKinnie
  • Patent number: 6162953
    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: September 28, 1999
    Date of Patent: December 19, 2000
    Assignee: Albemarle Corporation
    Inventors: Bonnie G. McKinnie, Richard A. Holub, Hassan Y. Elnagar
  • 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: 6049014
    Abstract: A process for producing n-propyl bromide during the bromination of bis- or trisphenols uses non-aqueous n-propanol as the bromination solvent, providing salable yields of n-propyl bromide to accompany the brominated bisphenol or trisphlenol.
    Type: Grant
    Filed: February 19, 1998
    Date of Patent: April 11, 2000
    Assignee: Great Lakes Chemical Corporation
    Inventors: Anne P. Noonan, Stephen C. Scherrer
  • Patent number: 5986149
    Abstract: The present invention provides processes for recovering alkanols from fluids comprising the alkanol and aqueous hydrobromic acid without forming excessive amounts of alkyl bromide. In certain aspects of the invention, there are provided distillation systems wherein a fluid comprising an alkanol and aqueous hydrobromic acid is introduced into a distillation column at a point between the bottom and the top of the column to thereby separate the alkanol and the hydrobromic acid without causing the production of a significant amount of alkyl bromide.
    Type: Grant
    Filed: April 3, 1998
    Date of Patent: November 16, 1999
    Assignee: Great Lakes Chemical Corporation
    Inventors: Richard J. DeGroot, James T. Ayers, Karl E. Reineke
  • Patent number: 5841001
    Abstract: The present invention provides an industrially advantageous process for the preparation of an optically active 2-halo-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or as intermediates thereof; and a simple process for the preparation of an optically active substituted styrene oxide or 2-amino-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or intermediates thereof. A 2-halo-1-(substituted phenyl)ethanol represented by the following general formula (I) is allowed to contact, in the presence of a carboxylic anhydride, with an enzyme stereoselectively catalyzing ester interchange to produce an optically active 2-halo-1-(substituted phenyl)ethanol: ##STR1## (wherein X represents a chlorine atom or a bromine atom, and R.sup.1, R.sup.2 and R.sup.3 may be the same or different and each represent a hydrogen atom, a halogen atom, a C.sub.1-5 alkyl group, a C.sub.1-5 haloalkyl group, a C.sub.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: November 24, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Ken Tanaka, Mari Yasuda, Makoto Ueda
  • Patent number: 5723690
    Abstract: This invention relates to a process for the production of tetrabromobisphenol-A by the bromination of bisphenol-A, which process features: a water and water miscible solvent reaction medium; a relatively high reaction temperature; the presence, in the reaction medium, of unreacted Br.sub.2 during the feed of bisphenol-A to the reactor; and the oxidation of co-produced HBr to yield Br.sub.2.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: March 3, 1998
    Assignee: Albemarle Corporation
    Inventor: Bonnie G. McKinnie
  • Patent number: 5710347
    Abstract: This invention relates to a method of producing a high-melting powder of 2,2-bis?4'-(2",3"-dibromopropoxy)-3',5'-dibromophenyl!propane characterized by comprising a step of adding water to a solution of 2,2-bis?4'-(2",3"-dibromopropoxy)-3',5'-dibromophenyl!-propane in an organic solvent in the presence of a surfactant to give a water-in-oil emulsion and a step of removing the organic solvent from the emulsion in the presence of a crystal nucleus to induce crystallization to give an aqueous dispersion of 2,2-bis?4'-(2",3"-dibromopropoxy)-3',5'-dibromophenyl!propane. In accordance with this invention, crystallization is carried out in the state of an emulsion under assistance of a surfactant so that an ordinary stirrer can be used in production without resort to any special high-shear stirring equipment. Moreover, since a high-melting grade of 2,2-bis?4'-(2",3"-dibromopropoxy)-3',5'-dibromophenyl!propane is obtained as an aqueous dispersion, workability and safety in the subsequent processing are improved.
    Type: Grant
    Filed: September 26, 1995
    Date of Patent: January 20, 1998
    Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.
    Inventors: Setsuo Nishibori, Hideaki Ohnishi, Tsuyoshi Furukawa
  • Patent number: 5395994
    Abstract: This invention provides an environmentally acceptable method for recovery of phenolic and brominated phenolic compounds, alcohol solvent, and bromide values from the a reaction medium liquid mixture formed in the production of a tetrabromobisphenol-A predominant product. The process comprises (a) separating the tetrabromobisphenol-A predominant product and alkyl bromide from the reaction medium thereby forming a liquid mixture containing alcohol, phenolic and brominated phenolic compounds, HBr, and water; (b) treating the liquid mixture with a sufficient amount of alkaline or alkaline earth metal hydroxide so as to form a treated aqueous mixture having a pH in the range of from about 9.5 to about 14.0, and containing MBr.sub.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: March 7, 1995
    Assignee: Albemarle Corporation
    Inventors: Robert E. Williams, William J. Cranston, III
  • Patent number: 5208389
    Abstract: The quality of a product predominant in tetrabromobisphenol-A is enhanced by contacting the product with a quality enhancing amount of treated water and heat treating the product for a period of time and at a temperature which are sufficient to obtain a TBBPA predominant product having less than about 20 ppm of ionic impurities.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: May 4, 1993
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Gary L. Sharp
  • 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: 4990321
    Abstract: A method for recovering hydrobromic acid and methanol from a filtrate obtained by brominating bisphenol A in a methanol solvent and filtering off the resulting brominated bisphenol A, which comprises adding water to the filtrate, followed by distillation for purification.
    Type: Grant
    Filed: January 24, 1990
    Date of Patent: February 5, 1991
    Assignee: Tosoh Corporation
    Inventors: Masakatsu Sato, Sadami Shimizu, Hanzo Tamabayashi
  • Patent number: 4612404
    Abstract: Polychlorinated biphenyls present as contaminants in fluids such as petroleum distillates are effectively removed by reacting with sodium or potassium hydroxide in the presence of or through subsequent filtration through an adsorbent such as alumina and/or diatomaceous earth. A mixture of diatomaceous earth, calcium hydroxide and potassium hydroxide in the ratio of 10/1/1 is exposed to the fluid to be decontaminated by stirring a quantity of the mixture in a quantity of the fluid or by passing the fluid through a column packed with the mixture. Alternatively, the contaminated fluid is mixed with the alkali metal hydroxide and then passed through a column of adsorbent such as activated basic alumina. The fluid may be pretreated by storing in a tank over a bed of potassium hydroxide flakes. Ferric oxide may be added to the reaction mixture to enhance the retention of the octachlorodihydroxybiphenyl on the adsorbent material.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: September 16, 1986
    Inventor: Budalur S. Thyagarajan
  • 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: 4291177
    Abstract: Highly pure dihalodiphenols or predetermined, statistical mixtures of unreacted, monohalo- and dihalodiphenols are obtained reacting the diphenol, which is suspended or dissolved in a suitable solvent, with a halogen while concurrently purging the reaction with a gas that is inert to the reaction.
    Type: Grant
    Filed: December 6, 1979
    Date of Patent: September 22, 1981
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles A. Wilson, II
  • Patent number: 4282391
    Abstract: A continuous process for obtaining highly pure, high molecular weight aromatic polycarbonates from highly pure, halogenated diphenols.
    Type: Grant
    Filed: December 10, 1979
    Date of Patent: August 4, 1981
    Assignee: General Electric Company
    Inventors: Clayton B. Quinn, Charles A. Wilson, II
  • Patent number: 4280012
    Abstract: A method of removing an impurity of the group chlorinated dibenzo-p-dioxins, chlorinated dibenzofurans, chlorinated hydroxydiphenylethers and chlorinated diphenylethers from a substance containing the same which comprises contacting said substance with an agent which is hydrazine, acetylene, an acetylene derivative or a compound which under the processing conditions is a source of hydrazine or acetylene.
    Type: Grant
    Filed: March 1, 1979
    Date of Patent: July 21, 1981
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Albino Pastura, Gerhard Kelbch, Hans-Leo Hulsmann
  • Patent number: 4242527
    Abstract: A process for purifying crude diphenols via a water co-solvent system is disclosed.
    Type: Grant
    Filed: May 23, 1979
    Date of Patent: December 30, 1980
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4228308
    Abstract: 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane can be dehydrohalogenated to 1,1-dichloro-2,2-bis(4-hydroxyphenyl) ethylene by treating the former with a dehydrochlorinating agent comprising liquid methyl amine and an effective amount of an additive to accelerate the dehydrochlorinating effect of the liquid methyl amine selected from the class consisting of a certain class of inorganic and organic salts.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: October 14, 1980
    Assignee: General Electric Company
    Inventor: Michael R. Mac Laury
  • Patent number: 4191843
    Abstract: A process for the preparation of bisphenols is described which comprises reacting, in a reaction zone, at least 2 moles of a phenol with a carbonyl compound, at a temperature of from 40.degree. to 95.degree. C., in the presence of an acid ion exchanger, optionally partially modified with a compound having an acidic reacting group and a mercaptan group, and recovering the bisphenols from the reaction zone effluent, characterized in that the reaction zone effluent is contacted with an acid ion exchanger in metal salt form and/or a weak base ion exchanger. As a result, it has been found that the formation of undesirable compounds is substantially reduced.
    Type: Grant
    Filed: November 7, 1978
    Date of Patent: March 4, 1980
    Assignee: Shell Oil Company
    Inventors: Arien Kwantes, Pieter A. Gautier
  • Patent number: 4180684
    Abstract: 4,4'-isopropylidene-bis(2,6-dibromophenol) is produced by reacting 4,4'-isopropylidene diphenol with hydrogen bromide or a mixture of hydrogen bromide with up to an equimolar amount of free bromine in admixture with hydrogen peroxide and in the presence of water and an inert organic liquid.
    Type: Grant
    Filed: January 14, 1977
    Date of Patent: December 25, 1979
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Peter Kleinschmit, Eberhard Walter, Helmut Mechler, Gunter Theis, Brigitte Meiners
  • Patent number: 4137421
    Abstract: Impure 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethylene can be purified by heating the latter either with phenol alone or with a mixture of methylene chloride and phenol, allowing the heated mixture to cool until crystallization occurs and removing the above-identified purified dichloroethylene compound.
    Type: Grant
    Filed: February 21, 1978
    Date of Patent: January 30, 1979
    Assignee: General Electric Company
    Inventors: Ming K. Li, Michael R. MacLaury
  • Patent number: 4110541
    Abstract: A method is provided for making substantially pure 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethylene by dehydrochlorinating 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane with a methanol solution of potassium hydroxide, followed by purifying the crude reaction product with a mixture of a hot aromatic solvent and a polar solvent, such as methanol.
    Type: Grant
    Filed: February 9, 1977
    Date of Patent: August 29, 1978
    Assignee: General Electric Company
    Inventor: Philip L. Kinson
  • Patent number: 4097538
    Abstract: 1,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethane can be dehydrohalogenated to 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethylene by treating the former with liquid ammonia.
    Type: Grant
    Filed: February 23, 1977
    Date of Patent: June 27, 1978
    Assignee: General Electric Company
    Inventors: Arnold Factor, Michael R. MacLaury, Jimmy L. Webb