Halogen Containing Patents (Class 568/726)
  • Patent number: 8969629
    Abstract: Disclosed are: a cyclic compound which has high solubility in a safe solvent, is highly sensitive, enables the formation of a resist pattern having a good shape, and rarely causes resist pattern collapse; a process for producing the cyclic compound; a radiation-sensitive composition containing the cyclic compound; and a resist pattern formation method using the composition. Specifically disclosed are: a cyclic compound having a specific structure; a process for producing the cyclic compound; a radiation-sensitive composition containing the compound; and a resist pattern formation method using the composition.
    Type: Grant
    Filed: November 25, 2010
    Date of Patent: March 3, 2015
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masaaki Takasuka, Masatoshi Echigo, Yu Okada
  • Patent number: 8889744
    Abstract: Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are hexafluoro-honokiol analogs. The compounds and compositions can be used to treat and/or prevent a wide variety of cancers, including drug resistant cancers. Representative hexafluoro-honokiol analogs include hexafluoro-honokiol, analogs in which one or both hydroxy groups are replaced with dichloroacetate esters, and analogs with increased fluorination. The compounds are believed to function, at least, by inhibiting angiogenesis and/or inducing apoptosis. Thus, the compounds are novel therapeutic agents for a variety of cancers.
    Type: Grant
    Filed: June 22, 2010
    Date of Patent: November 18, 2014
    Inventor: Jack L. Arbiser
  • Patent number: 8846292
    Abstract: A radiation-sensitive composition containing a resist compound having a high sensitivity, a high resolution, a high etching resistance, and a low outgas which forms a resist pattern with good shape and a method of forming a resist pattern and novel compositions for forming a photoresist under coat film which is excellent in optical properties and etching resistance and contains substantially no sublimable substance and an under coat film formed by the composition. Radiation-sensitive composition containing a solvent and a cyclic compound having, e.g., a cyclic compound (A) having a molecular weight of 700 to 5000 which is synthesized by the condensation reaction of a compound having 2 to 59 carbon atoms and 1 to 4 formyl groups with a compound having 6 to 15 carbon atoms and 1 to 3 phenolic hydroxyl groups, and a cyclic compound for use in the radiation-sensitive composition.
    Type: Grant
    Filed: December 29, 2011
    Date of Patent: September 30, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masatoshi Echigo, Dai Oguro
  • Patent number: 8748078
    Abstract: A cyclic compound represented by formula (1): wherein L, R1, R?, and m are as defined in the specification. The cyclic compound of formula (1) is highly soluble to a safety solvent, highly sensitive, and capable of forming resist patterns with good profile. Therefore, the cyclic compound is useful as a component of a radiation-sensitive composition.
    Type: Grant
    Filed: August 30, 2010
    Date of Patent: June 10, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hiromi Hayashi, Masatoshi Echigo, Dai Oguro
  • Publication number: 20130035304
    Abstract: This invention relates to compounds which selectively bind to the survival protein MCL-1 with high affinity and selectivity, pharmaceutical compositions containing such compounds and the use of those compounds or compositions for modulating MCL-1 activity and for treating hyperproliferative disorders, angiogenesis disorders, cell cycle regulation disorders, autophagy regulation disorders, inflammatory disorders, and/or infectious disorders and/or for enhancing cellular engraftment and/or wound repair, as a sole agent or in combination with other active ingredients.
    Type: Application
    Filed: January 31, 2011
    Publication date: February 7, 2013
    Inventors: Loren D. Walensky, Michelle L. Stewart, Nicole Cohen
  • Patent number: 8357701
    Abstract: Therapeutic agents for treatment of Galactosemia and disorders thereof, and other enzyme related disorders thereof are identified. The compounds inhibit galactokinase (GALK) and other kinase activity and are identified by a high throughput screening assay.
    Type: Grant
    Filed: August 14, 2008
    Date of Patent: January 22, 2013
    Assignee: University of Miami
    Inventors: Kent Lai, Klass Jan Wierenga, Manshu Tang
  • Patent number: 8350096
    Abstract: A radiation-sensitive composition containing 1 to 80% by weight of a solid component and 20 to 99% by weight of a solvent. The solid component contains a compound B which has (a) a structure derived from a polyphenol compound A by introducing an acid-dissociating group to at least one phenolic hydroxyl group of the polyphenol compound A which is synthesized by a condensation between a di- to tetrafunctional aromatic ketone or aromatic aldehyde each having 5 to 36 carbon atoms with a compound having 1 to 3 phenolic hydroxyl groups and 6 to 15 carbon atoms, and (b) a molecular weight of 400 to 2000. The composition containing the compound B is useful as an acid-amplified, non-polymeric resist material, because it is highly sensitive to radiation such as KrF excimer lasers, extreme ultraviolet rays, electron beams, and X-rays, and provides resist patterns with a high resolution, high heat resistance, and high etching resistance.
    Type: Grant
    Filed: March 18, 2011
    Date of Patent: January 8, 2013
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masatoshi Echigo, Dai Oguro
  • Publication number: 20120165406
    Abstract: Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are hexafluoro-honokiol analogs. The compounds and compositions can be used to treat and/or prevent a wide variety of cancers, including drug resistant cancers. Representative hexafluoro-honokiol analogs include hexafluoro-honokiol, analogs in which one or both hydroxy groups are replaced with dichloroacetate esters, and analogs with increased fluorination. The compounds are believed to function, at least, by inhibiting angiogenesis and/or inducing apoptosis. Thus, the compounds are novel therapeutic agents for a variety of cancers.
    Type: Application
    Filed: June 22, 2010
    Publication date: June 28, 2012
    Applicant: Jack L. Arbiser
    Inventor: Jack L. Arbiser
  • Patent number: 8110334
    Abstract: A radiation-sensitive composition containing a resist compound having a high sensitivity, a high resolution, a high etching resistance, and a low outgas which forms a resist pattern with a good shape is described. Further described is a method of forming a resist pattern using the radiation-sensitive composition. Still further described are a novel composition for forming a photoresist under coat film which is excellent in optical properties and etching resistance and contains substantially no sublimable substance and an under coat film formed by the composition.
    Type: Grant
    Filed: November 1, 2007
    Date of Patent: February 7, 2012
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masatoshi Echigo, Dai Oguro
  • Publication number: 20110251236
    Abstract: Therapeutic agents for treatment of Galactosemia and disorders thereof, and other enzyme related disorders thereof are identified. The compounds inhibit galactokinase (GALK) and other kinase activity and are identified by a high throughput screening assay.
    Type: Application
    Filed: August 14, 2008
    Publication date: October 13, 2011
    Applicant: University of Miami
    Inventors: Kent Lai, Klass Jan Wierenga, Manshu Tang
  • Publication number: 20110110886
    Abstract: Autotaxin (ATX) is a prometastatic enzyme initially isolated from the conditioned media of human melanoma cells that stimulates a myriad of biological activities including angiogenesis and the promotion of cell growth, survival, and differentiation through the production of lysophosphatidic acid (LPA). ATX increases the aggressiveness and invasiveness of transformed cells, and ATX levels directly correlate with tumor stage and grade in several human malignancies. To study the role of ATX in the pathogenesis of malignant melanoma, we developed antibodies and small molecule inhibitors against recombinant human protein. Immunohistochemistry of paraffin embedded human tissue demonstrates that ATX levels are markedly increased in human primary and metastatic melanoma relative to benign nevi. Chemical screens identified several small molecule inhibitors with binding constants ranging from nanomolar to low micromolar.
    Type: Application
    Filed: June 15, 2009
    Publication date: May 12, 2011
    Inventor: Demetrios Braddock
  • Patent number: 7932014
    Abstract: A photosensitive compound has two or more structural units, in a molecule, represented by the following general formula (1): wherein R1 to R8 are selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an acetoxy group, a phenyl group, a naphthyl group, and an alkyl group in which some or all of the hydrogen atoms are optionally replaced by fluorine atoms; R9 is a hydrogen atom or a hydroxyl group; X is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalene group; and Y is an oxygen atom or a single bond.
    Type: Grant
    Filed: February 14, 2008
    Date of Patent: April 26, 2011
    Assignee: Canon Kabushiki Kaisha
    Inventor: Toshiki Ito
  • Patent number: 7834221
    Abstract: A process for preparing tetrabromobisphenol A, which comprises: i) reacting bisphenol A and bromine in dichloromethane in the presence of aqueous hydrogen peroxide at a temperature in the range of room temperature to the reflux temperature, wherein said dichloromethane is present in an amount sufficient for substantially dissolving brominated derivatives of said bisphenol A formed thereby, ii) separating the substantially solid-free reaction mixture obtained in step i) into aqueous and organic phases, precipitating tetrabromobisphenol A from the organic phase and isolating said precipitated tetrabromobisphenol A from said organic phase.
    Type: Grant
    Filed: July 3, 2006
    Date of Patent: November 16, 2010
    Assignee: Bromine Compounds Ltd.
    Inventor: Joseph Zilberman
  • Publication number: 20100010274
    Abstract: A process for preparing tetrabromobisphenol A, which comprises: i) reacting bisphenol A and bromine in dichloromethane in the presence of aqueous hydrogen peroxide at a temperature in the range of room temperature to the reflux temperature, wherein said dichloromethane is present in an amount sufficient for substantially dissolving brominated derivatives of said bisphenol A formed thereby, ii) separating the substantially solid-free reaction mixture obtained in step i) into aqueous and organic phases, precipitating tetrabromobisphenol A from the organic phase and isolating said precipitated tetrabromobisphenol A from said organic phase.
    Type: Application
    Filed: July 3, 2006
    Publication date: January 14, 2010
    Inventor: Joseph Zilberman
  • Publication number: 20090221702
    Abstract: The present invention provides the use of a compound of the Formula: (I) wherein R1 is C1-5 alkoxy, OCOC1-3Alkyl, O(CH2)2O(CH2)2O(CH2)2OMe, O(CH2)2O(CH2)2O(CH2)2OH or OH; R2 is H, (CH2)nOH, OCH3, Hal or (II) or (III) R3 is H or (CH2)nOH; and R4 is C1-6 alkyl, optionally substituted by one or more of Hal, OH, COCH3, NH2, NHCH3, NHMe, NMe2, OCOCH3, CO2H or esters or amides thereof where n is 1-5; and pharmaceutically acceptable salts thereof, in the manufacture of a medicament for use in modulating PKB activity.
    Type: Application
    Filed: March 17, 2006
    Publication date: September 3, 2009
    Inventors: Rudiger Woscholski, Helen Hailes, Macba Numbere, Erika Rosivatz
  • Patent number: 6906226
    Abstract: Hydroxymethyl-substituted polyfunctional phenols, expressed by the following structure: General structure (I) (wherein X represents: bivalent group (a) expressed by the following structure: General structure (II) (wherein R1, R2, R3 and R4 each independently represent a hydrogen atom or an alkyl group with a carbon atom number of 1 through 4); quadrivalent group (b) expressed by the following structure: General structure (III) (wherein R5 and R6 each independently represent a hydrogen atom or an alkyl group with a carbon atom number of 1 through 4); or bivalent group (c) expressed by the following structure: General structure (IV) (wherein R7 and R8 each independently represent a hydrogen atom or a monofluoromethyl, difluoromethyl or trifluoromethyl group; however, R7 and R8 cannot be both hydrogen atoms); wherein n takes 2 when X is bivalent group (a), takes 4 when X is quadrivalent group (b), or takes 2 when X is bivalent group (c)).
    Type: Grant
    Filed: April 3, 2003
    Date of Patent: June 14, 2005
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Kazuya Matsuishi, Takayuki Ohno, Taiichi Shiomi
  • 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: 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
  • Patent number: 6610890
    Abstract: Medicaments for treating diabetic complications contain a compound of formula (A), wherein at least one Y or one Y′ is OH, and the remainder are selected from H, Hal, OH, OMe and NO2; X is O, S, keto or a direct link
    Type: Grant
    Filed: January 7, 2002
    Date of Patent: August 26, 2003
    Assignee: O.N.C.E.-(Organizacion Nacional De Cicgos)
    Inventors: Teresa Garcia de Quesada Fort, Jesús A De La Fuente Blanco, Ma Jesús Martin Lopez, Isabel Reymundo Cuesta
  • Patent number: 6365786
    Abstract: A highly pure and colorless tetrabromobisphenol-A (TBBPA) possessing melting point in the range of 178-182° C. is prepared in yields of 50-70% in first batch and 90-100% when the spent organic layer is recycled. In this method, the corrosive liquid bromine is displaced by sodium bromide/hydrobromic acid as brominating agent. Further, sodium bromate is used as an oxidizing as well as brominating agent to utilize the hydrobromic acid that is produced during the bromination of bisphenol-A (BPA). The reaction is conducted at 10-15° C. in a mixture of methylene chloride-water or carbon tetrachloride-water in the presence of hydrochloric acid and sodium lauryl sulfate. The crystalline product settled at the bottom of the reaction vessel is filtered, washed, dried and weighed. The spent organic layer is recycled in subsequent batches to maximize the overall yield of product recovered directly as solid and to minimize generation of organic effluent.
    Type: Grant
    Filed: January 22, 2001
    Date of Patent: April 2, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Gadde Ramachandraiah, Pushpito Kumar Ghosh, Aditya Shantilal Mehta, Rajesh Popatlal Pandya, Ashok Dahyabhai Jethva, Sanjay Shambhubhai Vaghela, Sudhindra Nath Misra
  • 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: 6245950
    Abstract: The invention relates to a process for the preparation of high quality tetrabromobisphenol-A by reacting bisphenol-A with bromine and hydrogen peroxide as an oxidant in the presence of a heterogeneous catalyst in a biphase system consisting of water and water immiscible organic solvents.
    Type: Grant
    Filed: March 30, 2000
    Date of Patent: June 12, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Mannepalli Lakshmi Kantam, Katuri Jeevaratnam, Boyapati Manoranjan Choudary, Chinta Reddy Venkat Reddy, Kondapuram Vijaya Raghavan, Lanka Venkata Sivaji, Thumma Someshwar
  • 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: 6147264
    Abstract: Bisphenol-A or preferably, a mixture of bisphenol-A and underbrominated bisphenol-A, is brominated in a liquid phase reaction medium in which tetrabromobisphenol-A is relatively insoluble, using a stoichiometric deficiency of bromine to thereby form in the reaction mass a precipitate (i.e., a solids phase) composed of 50-95 wt % of tetrabromobisphenol-A and 50-5 wt % of underbrominated bisphenol-A. The precipitate is separated from the reaction mass, preferably during the bromination, and tetrabromobisphenol-A is recovered from the precipitate. Preferably underbrominated bisphenol-A is recycled as feed to the bromination. The process technology of this invention has the capability of producing high quality tetrabromobisphenol-A (high purity, good color, low ionic halide content) with efficient raw material utilization, minimized waste product formation, and minimized waste disposal costs.
    Type: Grant
    Filed: April 8, 1999
    Date of Patent: November 14, 2000
    Assignee: Albemarle Corporation
    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: 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: 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: 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: 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: 5847232
    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: June 27, 1997
    Date of Patent: December 8, 1998
    Assignee: Albemarle Corporation
    Inventor: Bonnie G. McKinnie
  • Patent number: 5817888
    Abstract: A bromination process for organic compounds employs stabilized bromine chloride solutions as the brominating agent. Activated aromatic compounds such as anisole can be selectively monobrominated in the para-position in high purity and yield.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: October 6, 1998
    Assignee: Albemarle Corporation
    Inventors: Hassan Y. Elnagar, Robert L. Davis, Mahmood Sabahi
  • 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: 5527971
    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: April 24, 1995
    Date of Patent: June 18, 1996
    Assignee: Albemarle Corporation
    Inventor: Bonnie G. McKinnie
  • Patent number: 5475153
    Abstract: A process for the preparation of 4,4'-isopropylidene bis(2,6-dibromophenol), also known as tetrabrombisphenol A, that dramatically reduces the formation of alkyl bromide by-products. Bisphenol A is brominated with a C.sub.3 to C.sub.5 n-alcohol in a water mixture to suppress the formation of alkyl bromides. The bisphenol A is brominated between 15.degree. C. and 25.degree. C. and then heated at a 55.degree. C. to 70.degree. C. to insure bromination is complete. The tetrabrombisphenol A is then filtered from the reaction mixture and dried. Tetrabromobisphenol A produced from this process typically has a melting point of 180.degree. C. or higher, and is typically greater than 98% pure. Hydrogen peroxide is optionally combined with the reactants to reduce the amount of added bromine necessary for the bromination of the tetrabromobisphenol A.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: December 12, 1995
    Assignee: Great Lakes Chemical Corp.
    Inventor: Stuart Armstrong
  • 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: 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: 5313008
    Abstract: The invention relates to a process for the conversion of 8-hydroxymenthenes into 8-hydroxycymenes by treating the 8-hydroxymenthenes in the vapour phase with an alkaline dehydrogenation catalyst, e.g. palladium on an alkaline support. The process is carried out above 145.degree. C. The hydroxymenthene vapour is preferably passed through the catalyst system at a pressure below 8 kPa and/or with the aid of an inert gas or vapour. Oxygen may be present as a hydrogen acceptor. The process is particularly suitable for converting 8-hydroxy-p-menth-1-ene into 8-hydroxy-p-cymene. The reaction products are of value as intermediates in the preparation of musk fragrance chemicals.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: May 17, 1994
    Assignee: Unilever Patent Holdings B.V.
    Inventor: Christopher P. Newman
  • Patent number: 5302761
    Abstract: Single crystals of tetrabromobisphenol A having an average particle size of from 150 to 500 .mu.m, each having a polyhedral shape.
    Type: Grant
    Filed: May 19, 1993
    Date of Patent: April 12, 1994
    Assignee: Tosoh Corporation
    Inventors: Hanzo Tamabayashi, Shinji Kakimoto, Tetsuto Mizui, Akihiko Nomura, Koji Kunimoto
  • 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: 5237112
    Abstract: This invention relates to a process for preparing tetrabromobisphenol-A in high yield and high purity comprising: (a) forming a reaction solvent from at least one non-polar solvent and an amount of aqueous hydrogen peroxide; (b) charging an amount of alkylidenediphenol to the reaction solvent to form a reaction mass; (c) feeding an amount of bromine to the reaction mass at a temperature and for a period of time sufficient to tetra-brominate substantially all of the alkylidenediphenol thus charged; (d) maintaining during step (c) the amount of hydrogen peroxide less than an amount required to convert substantially all of the HBr which forms to elemental bromine; and (e) heat treating the formed product whereby a product having less than about 20 ppm ionic impurities is produced.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: August 17, 1993
    Assignee: Ethyl Corporation
    Inventor: David E. LaRose
  • 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: 5138103
    Abstract: A process for producing tetrabromobisphenol A of high quality, which comprises brominating bisphenol A with bromine, wherein a solvent mixture comprising a hydrohalogenic acid and an alcohol, is used as the solvent for reaction. Also disclosed is a process for producing tetrabromobisphenol A of high quality, which comprises brominating bisphenol A with bromine in an alcohol, wherein the reaction temperature is set at a level of from -10.degree. to +20.degree. C., and water is added in an aging step.
    Type: Grant
    Filed: August 16, 1991
    Date of Patent: August 11, 1992
    Assignee: Tosoh Corporation
    Inventors: Hisao Eguchi, Masashige Kubo, Noritaka Nagasaki, Koji Kunimoto
  • Patent number: 5136110
    Abstract: The invention is a process for the preparation of triaromatic bisphenols reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl, excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene and a large portion of the yield is para isomer.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: August 4, 1992
    Assignee: The Dow Chemical Company
    Inventors: Marlin E. Walters, W. Frank Richey, Emmett L. Tasset
  • Patent number: 5107035
    Abstract: The quality of a product predominant in tetrabromobisphenol-A is enhanced by 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 50 ppm of hydrohalide impurities.
    Type: Grant
    Filed: November 15, 1990
    Date of Patent: April 21, 1992
    Assignee: Ethyl Corporation
    Inventors: Harold W. Hines, Daniel A. Wood
  • Patent number: 5068463
    Abstract: A process for the production of tetrabromo-4,4'-alkylidenediphenols, especially tetrabromobisphenol A (TBBA), from the corresponding alkylidenediphenols by oxidative bromination with Br.sub.2, HBr.sub.3 or HBr and aqueous hydrogen peroxide in the presence of an organic solvent. The process is characterized by washing the organic phase containing dissolved tetrabromo-4,4'-alkylidenediphenol with an aqeuous alkali sulphite solution, preferably at 50.degree. to 90.degree. C. Through this washing treatment, the tetrabromo compound is obtained in higher purity; in addition, the mother liquor can be recycled without difficulty.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: November 26, 1991
    Inventor: Eberhard Walter
  • Patent number: 5064518
    Abstract: Inorganic and organic hypohalites are used to obtain good selectivity to alpha halogenation of alkyl aromatic compounds. Alkali and alkaline earth hypohalites must be used in conjunction with a phase transfer medium. Useful organic hypohalites are the tertiary alkyl hypohalites, which are employed in the presence of free radical generating media such as light or compounds which produce free radicals thermally. At least one mole of hypohalite reactant must be used for every alpha hydrogen in the alkyl aromatic compound.A new bisphenol which contains biphenyl functionality has been made as well as an aromatic polyester derived therefrom.
    Type: Grant
    Filed: November 1, 1990
    Date of Patent: November 12, 1991
    Assignee: The Dow Chemical Company
    Inventors: Marlin E. Walters, George M. St. George, W. Frank Richey