Oxirane Ring And Chalcogen, Cyano, Nitrogen, Or Halogen Are Bonded Directly To The Same Carbon (e.g., Glycidyl Ester Formed, Etc.) Patents (Class 549/521)
  • Patent number: 9963436
    Abstract: A process for manufacturing epoxy monomers and/or epoxides in high yields and useful quality and chemical stability by dehydrochlorination of the corresponding chlorohydrins with an alkaline agent, producing the corresponding side product dry salt in a high purity, characterized in that the process comprises the following steps: a. Reaction of the chlorohydrins with the alkaline agent to form corresponding epoxides and the corresponding precipitated chloride salt; b. Dehydration, and optionally completing the reaction, of the reaction mixture of step (a), by use of an azeotropic agent, added to step (b) or generated in situ in step (a), resulting in the producing of a dehydrated reaction mixture; c. Separating the resulting chloride salt by filtration from the dehydrated reaction mixture (b) and d. Isolating the epoxide from the filtered liquid fraction.
    Type: Grant
    Filed: February 8, 2017
    Date of Patent: May 8, 2018
    Assignee: SPOLEK PRO CHEMICKOU A HUTNI VYROBU
    Inventors: Pavel Kubicek, Bedrich Nemecek, Petr Sladek
  • Patent number: 8975449
    Abstract: A method of preparing chlorohydrins and a method of preparing epichlorohydrin by using chlorohydrins prepared using the method are provided. The method of preparing chlorohydrins by reacting polyhydroxy aliphatic hydrocarbon with a chlorination agent in the presence of a catalyst includes at least one combination of a series of unit operations including a first reaction step, a water removal step, and a second reaction step, in that respective order, and after mixing at least a portion of a reaction mixture discharged from at least one reaction steps from among the plurality of reaction steps with an additional chlorination agent, recirculating the resulting mixture to the reaction step from which the reaction mixture was discharged. The method of preparing epichlorohydrin includes a step of reacting chlorohydrins prepared using the method of preparing chlorohydrins, with an alkaline agent.
    Type: Grant
    Filed: June 8, 2011
    Date of Patent: March 10, 2015
    Assignee: Samsung Fine Chemicals Co., Ltd.
    Inventors: Won Seob Song, Sung Yul Woo, Boo Weon Song, Seong Han Park, Myoung Suk Kwon
  • Patent number: 8969601
    Abstract: Disclosed are a method for preparing chlorohydrins composition and a method for preparing epichlorohydrin using chlorohydrins prepared thereby. The disclosed method for preparing chlorohydrins composition reacts polyhydroxy aliphatic hydrocarbon with a chlorination agent in the presence of a catalyst, comprises at least one combination of a series of unit operations including a first reaction step, a water removal step, and a second reaction step in the respective order, and additionally comprises a step for reacting the chlorohydrins composition derived from a plurality of reaction mixtures discharged from the plurality of reaction steps with an alkaline chemical, and removing the catalyst included in the chlorohydrins composition in the form of an alkali metal salt. The disclosed method for preparing epichlorohydrin includes a step for contacting the chlorohydrins composition, which was prepared using the method for preparing chlorohydrins composition, with an alkaline chemical.
    Type: Grant
    Filed: June 8, 2011
    Date of Patent: March 3, 2015
    Assignee: Samsung Fine Chemicals Co., Ltd.
    Inventors: Won Seob Song, Sung Yul Woo, Boo Weon Song, Seong Han Park, Myoung Suk Kwon
  • Patent number: 8969631
    Abstract: A method of preparing a chlorohydrin composition and a method of preparing epichlorohydrin by using a chlorohydrin composition prepared by using the method are provided. The method of preparing a chlorohydrin composition in which a polyhydroxy aliphatic hydrocarbon is reacted with a chlorination agent in the presence of a catalyst includes performing at least one combination of a series of unit operations comprising a first reaction step, a water removal step, and a second reaction step in this stated order, wherein the method further includes mixing a chlorohydrin concentrate obtained by purifying the reaction mixture discharged from the final reaction step from among the plurality of reaction steps and a water-rich layer discharged from the water-removal step. The method of preparing epichlorohydrin includes contacting the chlorohydrin composition prepared by using the method of preparing a chlorohydrin composition with an alkaline agent.
    Type: Grant
    Filed: June 8, 2011
    Date of Patent: March 3, 2015
    Assignee: Samsung Fine Chemicals Co., Ltd.
    Inventors: Won Seob Song, Sung Yul Woo, Boo Weon Song, Seong Han Park, Myoung Suk Kwon
  • Patent number: 8921585
    Abstract: The present invention provides an efficient method of synthesizing and purifying dianhydrohexitols such as dianhydrogalactitol. In general, as applied to dianhydrogalactitol, the method comprises: (1) reacting dulcitol with a concentrated solution of hydrobromic acid at a temperature of about 80° C. to produce dibromogalactitol; (2) reacting the dibromogalactitol with potassium carbonate in t-butanol to produce dianhydrogalactitol; and (3) purifying the dianhydrogalactitol using a slurry of ethyl ether to produce purified dianhydrogalactitol. Another method produces dianhydrogalactitol from dulcitol; this method comprises: (1) reacting dulcitol with a reactant to convert the 1,6-hydroxy groups of dulcitol to an effective leaving group to generate an intermediate; and (2) reacting the intermediate with an inorganic weak base to produce dianhydrogalactitol through an intramolecular SN2 reaction. Other methods for the synthesis of dianhydrogalactitol from dulcitol are described.
    Type: Grant
    Filed: July 2, 2013
    Date of Patent: December 30, 2014
    Assignee: Del Mar Pharmaceuticals
    Inventor: Dennis M. Brown
  • Publication number: 20130281721
    Abstract: Processes and apparatus for purifying brine are provided including (1) providing an aqueous brine solution comprising one or more inorganic salts and one or more organic compounds and (2) conducting at least one unit operation for removing organic compounds from the brine solution to obtain a purified brine solution.
    Type: Application
    Filed: June 20, 2013
    Publication date: October 24, 2013
    Inventors: Bruce Hook, Dan Tirtowidjojo, Anil Mehta
  • Patent number: 8563758
    Abstract: The present invention provides an efficient method of synthesizing and purifying dianhydrohexitols such as dianhydrogalactitol. In general, as applied to dianhydrogalactitol, the method comprises: (1) reacting dulcitol with a concentrated solution of hydrobromic acid at a temperature of about 80° C. to produce dibromogalactitol; (2) reacting the dibromogalactitol with potassium carbonate in t-butanol to produce dianhydrogalactitol; and (3) purifying the dianhydrogalactitol using a slurry of ethyl ether to produce purified dianhydrogalactitol.
    Type: Grant
    Filed: August 17, 2011
    Date of Patent: October 22, 2013
    Assignee: Del Mar Pharmaceuticals
    Inventor: Dennis M. Brown
  • Patent number: 8558021
    Abstract: The present invention relates to a process for the catalytic halogenation of an organic compound comprising at least one vicinal diol moiety, said process comprising a step of bringing the organic compound comprising at least one vicinal diol moiety into contact with a hydrogen halide in the presence of a catalyst, characterized in that the catalyst is an organic compound comprising a ?-diketone moiety or a ?-keto aldehyde moiety.
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: October 15, 2013
    Assignee: Akzo Nobel N.V.
    Inventors: Antoon Jacob Berend Ten Kate, Richard Herman Woudenberg, Eilertdina Henderika Renkema, Luc Louis Theophile Vertommen, Carolina Anna Maria Christina Dirix, Tim Baks
  • Publication number: 20130211111
    Abstract: The present invention provides an efficient method of synthesizing and purifying dianhydrohexitols such as dianhydrogalactitol. In general, as applied to dianhydrogalactitol, the method comprises: (1) reacting dulcitol with a concentrated solution of hydrobromic acid at a temperature of about 80° C. to produce dibromogalactitol; (2) reacting the dibromogalactitol with potassium carbonate in t-butanol to produce dianhydrogalactitol; and (3) purifying the dianhydrogalactitol using a slurry of ethyl ether to produce purified dianhydrogalactitol.
    Type: Application
    Filed: August 17, 2011
    Publication date: August 15, 2013
    Applicant: Del Mar Pharmaceuticals
    Inventor: Dennis M. Brown
  • Publication number: 20130090485
    Abstract: A method of preparing chlorohydrins and a method of preparing epichlorohydrin by using chlorohydrins prepared using the method are provided. The method of preparing chlorohydrins by reacting polyhydroxy aliphatic hydrocarbon with a chlorination agent in the presence of a catalyst includes at least one combination of a series of unit operations including a first reaction step, a water removal step, and a second reaction step, in that respective order, and after mixing at least a portion of a reaction mixture discharged from at least one reaction steps from among the plurality of reaction steps with an additional chlorination agent, recirculating the resulting mixture to the reaction step from which the reaction mixture was discharged. The method of preparing epichlorohydrin includes a step of reacting chlorohydrins prepared using the method of preparing chlorohydrins, with an alkaline agent.
    Type: Application
    Filed: June 8, 2011
    Publication date: April 11, 2013
    Inventors: Won Seob Song, Sung Yul Woo, Boo Weon Song, Seong Han Park, Myoung Suk Kwon
  • Patent number: 8389777
    Abstract: Continuous process for producing a chlorohydrin, wherein a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof is reacted with a chlorinating agent and an organic acid in a liquid reaction medium whose steady-state composition comprises the polyhydroxylated aliphatic hydrocarbon and esters of the polyhydroxylated aliphatic hydrocarbon whose sum content, expressed as moles of polyhydroxylated aliphatic hydrocarbon, is greater than 1.1 mol % and less than or equal to 30 mol %, the percentage being based on the organic part of the liquid reaction medium.
    Type: Grant
    Filed: May 19, 2006
    Date of Patent: March 5, 2013
    Assignee: Solvay (Société Anonyme)
    Inventor: Patrick Gilbeau
  • Publication number: 20130053557
    Abstract: Processes and intermediates for preparing linezolid, and pharmaceutically acceptable salts thereof, are described herein.
    Type: Application
    Filed: April 28, 2011
    Publication date: February 28, 2013
    Applicant: INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION
    Inventor: James R. McCarthy
  • Patent number: 8304563
    Abstract: The present invention relates to a process for converting a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin, by contacting the multihydroxylated-aliphatic hydrocarbon or ester thereof starting material with a source of hydrogen chloride at superatmospheric, atmospheric and subatmospheric pressure conditions for a sufficient time and at a sufficient temperature, preferably wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; said process carried out without a step undertaken to specifically remove volatile chlorinated hydrocarbon by-products or chloroacetone, wherein the combined concentration of volatile chlorinated hydrocarbon by-products and chloroacetone is less than 2000 ppm throughout any stage of the said process.
    Type: Grant
    Filed: January 31, 2011
    Date of Patent: November 6, 2012
    Assignee: Dow Global Technologies LLC
    Inventors: William J. Kruper, Tina Arrowood, Bruce M. Bell, John Briggs, Robert M. Campbell, Bruce D. Hook, Anh Nguyen, Curt Theriault, Ralf Fitschen
  • Patent number: 8236975
    Abstract: A process for converting a crude glycerol, crude mixtures of naturally derived multihydroxylated-aliphatic hydrocarbons or esters thereof to a chlorohydrin, by contacting the crude glycerol, crude mixtures of naturally derived multihydroxylated-aliphatic hydrocarbons or esters thereof starting material with a source of a superatmospheric partial pressure of hydrogen chloride for a sufficient time and at a sufficient temperature, and wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; wherein said crude glycerol, said ester of crude glycerol, or mixture thereof is derived from a renewable raw material. Chlorohydrins made by the process of the present invention are useful in preparing epoxides such as epichlorohydrins.
    Type: Grant
    Filed: February 9, 2011
    Date of Patent: August 7, 2012
    Inventors: Bruce D. Hook, John Briggs, Robert M. Campbell, William J. Kruper, David J. Schreck, Richard D. Varjian, Jeffrey G. Hippler
  • Publication number: 20120004432
    Abstract: The present invention relates to a process for the catalytic halogenation of an organic compound comprising at least one vicinal diol moiety, said process comprising a step of bringing the organic compound comprising at least one vicinal diol moiety into contact with a hydrogen halide in the presence of a catalyst, characterized in that the catalyst is an organic compound comprising a ?-diketone moiety or a ?-keto aldehyde moiety.
    Type: Application
    Filed: March 17, 2010
    Publication date: January 5, 2012
    Applicant: AKZO NOBEL N.V.
    Inventors: Antoon Jacob Berend Ten Kate, Richard Herman Woudenberg, Eilertdina Henderika Renkema, Luc Louis Theophile Vertommen, Carolina Anna Maria Christina Dirix, Tim Baks
  • Patent number: 8067645
    Abstract: Process for producing a chlorohydrin by reaction between a multihydroxylated-aliphatic hydrocarbon, an ester of a multihydroxylated-aliphatic hydrocarbon, or a mixture thereof, and a chlorinating agent, according to which the multihydroxylated-aliphatic hydrocarbon, the ester of a multihydroxylated-aliphatic hydrocarbon, or the mixture thereof used contains at least one solid or dissolved metal salt, the process comprising a separation operation to remove at least part of the metal salt.
    Type: Grant
    Filed: May 19, 2006
    Date of Patent: November 29, 2011
    Assignee: Solvay (Societe Anonyme)
    Inventors: Patrick Gilbeau, Ivan de Andolenko, Philippe Krafft, Freddy Gielen
  • Patent number: 7985867
    Abstract: A process for producing epoxides, the process including: (a) feeding at least one aqueous alkali and at least one halohydrin to a reactive distillation column, wherein the reactive distillation column includes a feed zone, a top zone disposed above the feed zone, and a bottom zone disposed below the feed zone; (b) concurrently in the reactive distillation column: (i) reacting at least a portion of the halohydrin with the alkali to form an epoxide; and (ii) stripping water and the epoxide from a basic aqueous residue; (c) recovering the water and the epoxide from the reactive distillation column as an overheads fraction; (d) condensing and phase separating the overheads fraction to form an organic overheads fraction including the epoxide and an aqueous overheads fraction including water; and (e) maintaining a liquid holdup per plate in the feed zone at a residence time of 10 seconds or less.
    Type: Grant
    Filed: July 23, 2009
    Date of Patent: July 26, 2011
    Assignee: Dow Global Technologies LLC
    Inventors: William W. Fan, Christian D. Kneupper, Sascha Noormann, Renate Patrascu
  • Publication number: 20110178315
    Abstract: A process for converting a crude glycerol, crude mixtures of naturally derived multihydroxylated-aliphatic hydrocarbons or esters thereof to a chlorohydrin, by contacting the crude glycerol, crude mixtures of naturally derived multihydroxylated-aliphatic hydrocarbons or esters thereof starting material with a source of a superatmospheric partial pressure of hydrogen chloride for a sufficient time and at a sufficient temperature, and wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; wherein said crude glycerol, said ester of crude glycerol, or mixture thereof is derived from a renewable raw material. Chlorohydrins made by the process of the present invention are useful in preparing epoxides such as epichlorohydrins.
    Type: Application
    Filed: February 9, 2011
    Publication date: July 21, 2011
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Bruce D. Hook, John Briggs, Robert M. Campbell, William J. Kruper, JR., David J. Schreck, Richard D. Varjian, Jeffrey G. Hippler
  • Patent number: 7982061
    Abstract: A process for producing epoxides, the process including: (a) feeding at least one aqueous alkali and at least one halohydrin to a reactive distillation column; (b) concurrently in the reactive distillation column: (i) reacting at least a portion of the halohydrin with the alkali to form an epoxide; and (ii) stripping water and the epoxide from a basic aqueous residue; (c) recovering the water and the epoxide from the reactive distillation column as an overheads fraction; and, (d) condensing and phase separating the overheads fraction at a temperature of 50° C. or less to form an organic overheads fraction including the epoxide and an aqueous overheads fraction including water.
    Type: Grant
    Filed: July 23, 2009
    Date of Patent: July 19, 2011
    Inventors: William W. Fan, Christian D. Kneupper, Sascha Noormann, Renate Patrascu
  • Publication number: 20110166369
    Abstract: Process for purifying hydrogen chloride, comprising at least one step of bringing said hydrogen chloride into contact with a scrubbing agent containing at least one chlorohydrin.
    Type: Application
    Filed: September 11, 2009
    Publication date: July 7, 2011
    Applicant: SOLVAY SA
    Inventors: Philippe Krafft, Patrick Gilbeau
  • Publication number: 20110124892
    Abstract: The present invention relates to a process for converting a multihydroxylated-aliphatic hydrocarbon or ester thereof to a chlorohydrin, by contacting the multihydroxylated-aliphatic hydrocarbon or ester thereof starting material with a source of hydrogen chloride at superatmospheric, atmospheric and subatmospheric pressure conditions for a sufficient time and at a sufficient temperature, preferably wherein such contracting step is carried out without substantial removal of water, to produce the desired chlorohydrin product; wherein the desired product or products can be made in high yield without substantial formation of undesired overchlorinated byproducts; said process carried out without a step undertaken to specifically remove volatile chlorinated hydrocarbon by-products or chloroacetone, wherein the combined concentration of volatile chlorinated hydrocarbon by-products and chloroacetone is less than 2000 ppm throughout any stage of the said process.
    Type: Application
    Filed: January 31, 2011
    Publication date: May 26, 2011
    Inventors: William J. Kruper, JR., Tina Arrowood, Bruce Michael Bell, John Briggs, Robert M. Campbell, Bruce D. Hook, Anh Nguyen, Curt Theriault, Ralf Fitschen
  • Patent number: 7931946
    Abstract: Disclosed are a novel liquid crystal compound containing a sulfone group, a liquid crystal composition comprising the same, and an optical film using the same liquid crystal composition. More particularly, there are provided a liquid crystal material for a viewing angle compensation film with high quality characteristics, which can improve a contrast ratio measured at a tilt angle to the front and minimize variations in color with viewing angles in a black state, a liquid crystal composition comprising the same liquid crystal material, and a compensation film obtained from the same liquid crystal composition.
    Type: Grant
    Filed: January 22, 2008
    Date of Patent: April 26, 2011
    Assignee: LG Chem, Ltd.
    Inventors: Jae-Ho Cheong, Min-Jin Ko, Myung-Sun Moon, Bum-Gyu Choi, Dae-Ho Kang, Ki-Youl Lee, Yun-Bong Kim
  • Patent number: 7906691
    Abstract: Process for preparing a chlorohydrin, comprising a step in which a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof is subjected to reaction with a chlorinating agent containing hydrogen chloride and at least one other step, carried out in apparatus made from or covered with materials which are resistant to the chlorinating agent under the conditions in which this step is realized.
    Type: Grant
    Filed: May 19, 2006
    Date of Patent: March 15, 2011
    Assignee: Solvay (Societe Anonyme)
    Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Valentine Smets, Christian Franck
  • Publication number: 20100331555
    Abstract: A process and apparatus are disclosed for the purification of epichlorohydrin. The process includes distilling and/or fractionating a feed stream containing epichlorohydrin, dichlorohydrin(s), and one or more other substances, subjecting at least a portion of the liquid phase effluent to a dichlorohydrin dehydrochlorination process for converting residual dichlorohydrin(s) in the liquid phase effluent to epichlorohydrin, and recovering purified epichlorohydrin from the vapor phase effluent in which the distillation/fractionation pressure and/or temperature of step (1) is adjusted to retain at least 5 weight-percent epichlorohydrin in the liquid phase effluent. The apparatus for making purified epichlorohydrin includes a dehydrochlorination apparatus, a first liquid-vapor contacting apparatus, and a second liquid-vapor contacting apparatus connected to the dehydrochlorination apparatus for recycling a distillate to the dehydrochlorination apparatus.
    Type: Application
    Filed: January 22, 2009
    Publication date: December 30, 2010
    Inventors: Christian D. Kneupper, Perry S. Basile, William W. Fan, Sascha Noormann
  • Publication number: 20100029959
    Abstract: A process for producing epoxides, the process including: (a) feeding at least one aqueous alkali and at least one halohydrin to a reactive distillation column, wherein the reactive distillation column includes a feed zone, a top zone disposed above the feed zone, and a bottom zone disposed below the feed zone; (b) concurrently in the reactive distillation column: (i) reacting at least a portion of the halohydrin with the alkali to form an epoxide; and (ii) stripping water and the epoxide from a basic aqueous residue; (c) recovering the water and the epoxide from the reactive distillation column as an overheads fraction; (d) condensing and phase separating the overheads fraction to form an organic overheads fraction including the epoxide and an aqueous overheads fraction including water; and (e) maintaining a liquid holdup per plate in the feed zone at a residence time of 10 seconds or less.
    Type: Application
    Filed: July 23, 2009
    Publication date: February 4, 2010
    Applicant: DOW GLOBAL TECHNOLOGIES INC.
    Inventors: William W. Fan, Christian D. Kneupper, Sascha Noormann, Renate Patrascu
  • Publication number: 20090275726
    Abstract: Process for producing epichlorohydrin comprising subjecting to a dehydrochlorination operation, dichloropropanol produced from glycerol comprising aldehydes.
    Type: Application
    Filed: July 14, 2009
    Publication date: November 5, 2009
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventors: Philippe KRAFFT, Patrick Gilbeau, Benoît Gosselin, Sara Claessens
  • Publication number: 20090270588
    Abstract: Process for producing dichloropropanol wherein glycerol is reacted with at least one chlorinating agent in a reactor made of or coated with materials selected from enamelled steel, polyolefins, fluorinated polymers, phenolic resins, tantalum, and silver.
    Type: Application
    Filed: July 14, 2009
    Publication date: October 29, 2009
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventors: Philippe KRAFFT, Patrick Gilbeau, Benoit Gosselin, Sara Claessens
  • Patent number: 7582781
    Abstract: The present invention provides an industrially safe, easily operable process for producing an optically active epoxy alcohol derivative useful as an intermediate for pharmaceuticals from inexpensively available materials, and also provides a novel halohydrin derivative serving as an important intermediate for the epoxy alcohol derivative. Furthermore, the present invention provides a process for producing an intermediate for a triazole antifungal agent by allowing a halohydrin to react with a triazole sulfonamide, the process including a small number of steps.
    Type: Grant
    Filed: July 5, 2004
    Date of Patent: September 1, 2009
    Assignee: Kaneka Corporation
    Inventors: Kazumi Okuro, Tatsuyoshi Tanaka, Masaru Mitsuda, Kenji Inoue
  • Publication number: 20080207930
    Abstract: Process for producing a chlorohydrin by reaction between a multihydroxylated-aliphatic hydrocarbon, an ester of a multihydroxylated-aliphatic hydrocarbon, or a mixture thereof, and a chlorinating agent, according to which the multihydroxylated-aliphatic hydrocarbon, the ester of a multihydroxylated-aliphatic hydrocarbon, or the mixture thereof used contains at least one solid or dissolved metal salt, the process comprising a separation operation to remove at least part of the metal salt.
    Type: Application
    Filed: May 19, 2006
    Publication date: August 28, 2008
    Inventors: Patrick Gilbeau, Ivan de Andolenko, Philippe Krafft, Freddy Gielen
  • Patent number: 7405312
    Abstract: The present invention relates to a method for preparing hexafluoropropylene oxide with high yield, and particularly to a method for preparing hexafluoropropylene oxide comprising the step of performing a two-phase interfacial reaction between an organic phase containing hexafluoropropylene and an aqueous phase containing a hypochlorite oxidant in the presence of a phase-transfer catalyst and a non-ionic surfactant to improve the degree of emulsification and dispersion of the organic phase and to increase the contact interfacial area, thereby increasing the efficiency and the yield of the reaction.
    Type: Grant
    Filed: February 5, 2007
    Date of Patent: July 29, 2008
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Soo Bok Lee, In Jun Park, Dong-Kwon Kim, Jeong-Hoon Kim, Jong-Wook Ha, Bong-Jun Chang, Kwang-won Lee, Kwang-Han Kim, Jaewon Kim
  • Patent number: 6946566
    Abstract: A process for preparing regioselectively an optically active 1-halogeno-2-hydroxypropyl compound of the following formula; wherein X is halogen atom and Nu is a heteroatom having a substituent, and an optically active glycidyl compound of the formula; which comprises reacting an optically active epihalohydrin of the formula; with a neucleophilic agent, in the presence of a metal complex of the formula; wherein n is an integer of 0, 1 or 2, Y1, Y2 and Y3 are hydrogen atom, etc., and Y2 and Y3 may form a ring such as benzene, A is a counterion and M is a metal ion, and further subjecting the compound (4) to reaction with a base to prepare the optically active glycidyl compound (5).
    Type: Grant
    Filed: July 30, 2003
    Date of Patent: September 20, 2005
    Assignee: Daiso Co., Ltd.
    Inventors: Keisuke Yaegashi, Yoshiro Furukawa
  • Patent number: 6765100
    Abstract: The invention relates to a method for industrially producing highly pure (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoepoxide (crystal) or (2R, 3S)- or (2S, 3R)-N-carbamate-protected &bgr;-aminoalcohol.
    Type: Grant
    Filed: October 10, 2001
    Date of Patent: July 20, 2004
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tomoyuki Onishi, Naoko Hirose, Yasuyuki Otake, Takashi Nakano, Yutaka Honda, Masakazu Nakazawa, Kunisuke Izawa
  • Patent number: 6764545
    Abstract: The present invention provides a production method including adding water to a solution of (2R,3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane ((2R,3S)-epoxide compound) or (2S,3R)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane ((2S,3R)-epoxide compound) in a polar solvent to allow crystallization, whereby to produce crystals of the (2R,3S)-epoxide compound or the (2S,3R)-epoxide compound conveniently in a high yield by an industrial production method without requiring an extremely low temperature.
    Type: Grant
    Filed: December 11, 2001
    Date of Patent: July 20, 2004
    Assignee: Ajinomoto Co., Inc.
    Inventors: Yuichi Suzuki, Naoko Hirose, Tomoyuki Onishi, Kunisuke Izawa
  • Patent number: 6639085
    Abstract: A process for producing propylene oxide, which comprises steps described below, wherein the concentration of water in a solution containing isopropylbenzene hydroperoxide to be supplied to the epoxidation step is 1% by weight or less: oxidation step; a step in which isopropylbenzene is oxidized to obtain isopropylbenzene hydroperoxide, epoxidation step; a step in which isopropylbenzene hydroperoxide obtained in the oxidation step is reacted with propylene to obtain propylene oxide and cumyl alcohol, and hydrogenolysis step; a step in which cumyl alcohol obtained in the epoxidation step is subjected to hydrogenolysis to obtain isopropylbenzene, and said isopropylbenzene is recycled to the oxidation step as a raw material for the oxidation step.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: October 28, 2003
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junpei Tsuji, Jun Yamamoto
  • Patent number: 6586607
    Abstract: A process for the preparation of diglycidylether of alkoxylated resorcinol using novel catalysts is disclosed. In particular, it has been found that antimony, indium and tellurium halides are effective catalysts for preparation of the diglycidylether of alkoxylated resorcinol.
    Type: Grant
    Filed: April 11, 2002
    Date of Patent: July 1, 2003
    Assignee: Indspec Chemical Corporation
    Inventors: Raj B. Durairaj, Gary A. Jesionowski
  • Publication number: 20010018532
    Abstract: A process for producing (2R,3S)-3-amino-4-phenylbutane-1,2-epoxide compounds which comprises treating a (2S,3S)-3-amino-1-halo-2-hydroxy-4-phenylbutane compound a (2S,3S)-3-amino-4-phenylbutane-1,2-epoxide with a carboxylic acid quaternary ammonium salt or a carboxylic acid metal salt a quaternary ammonium salt and a quaternary ammonium salt, to give a (2S,3S)-1-acyloxy-3-amino-2-hydroxy-4-phenylbutane compound, further treating the same with a sulfonic acid halide in the presence of an organic base to give a (2S,3S)-1-acyloxy-3-amino-2-sulfonyloxy-4-phenylbutane compound furthermore treating said compound with an inorganic base.
    Type: Application
    Filed: May 11, 2001
    Publication date: August 30, 2001
    Applicant: KANEKA CORPORATION
    Inventors: Kazumi Okuro, Kenji Inoue
  • Patent number: 5965753
    Abstract: A process for preparation of a glycidyl sulfonate derivative with high purity and in high yield, which is characterized in reacting glycidol which is prepared from treating 3-chloro-1,2-propanediol in an aqueous solvent in the basic condition, without isolating the resulting glycidol with a sulfonyl halide in a two phase solvent consisting of an organic solvent and water in the presence of an inorganic base and a tertiary amine or a pyridine derivative.
    Type: Grant
    Filed: July 20, 1998
    Date of Patent: October 12, 1999
    Assignee: Daiso Co., LTd.
    Inventors: Midori Masaki, Yoshiro Furukawa, Keishi Takenaka
  • Patent number: 5936104
    Abstract: The present invention provides a process for producing 1,2-epoxy-3-amino-4-phenylbutane derivatives which comprises treating a 1-halo-2-hydroxy-3-amino-4-phenylbutane derivative with a base in an aprotic polar organic solvent or a mixed solvent composed of an aprotic polar organic solvent and water and then causing the resulting epoxide to crystallize out from a mixed solvent composed of an aprotic polar organic solvent and water.
    Type: Grant
    Filed: August 8, 1997
    Date of Patent: August 10, 1999
    Assignee: Kaneka Corporation
    Inventors: Akira Nishiyama, Tadashi Sugawa, Hajime Manabe, Kenji Inoue, Noritaka Yoshida
  • Patent number: 5847169
    Abstract: A process for preparing oxiranemethane derivatives which are useful as intermediates for preparing aspartyl protease inhibitors comprising the steps of activating an aminodiol, acylating the aminodiol and reacting the acylated aminodiol with a base to form an epoxy compound.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: December 8, 1998
    Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.
    Inventors: Laurence J. Nummy, Denis P. Byrne
  • Patent number: 5824821
    Abstract: The invention provides a process for the production of a 2,3-dihydroxypropylamino compound, said process comprising the reaction steps of:(i) obtaining an allylamino compound;(ii) epoxidizing said allylamino compound to yield an epoxypropylamino compound; and(iii) hydrolysing said epoxypropylamino compound to yield a 2,3-dihydroxypropylamino compound.This process may be used to produce simple 2,3-dihydroxypropylamino compounds such as APD or complex ones such as BAPD (an intermediate in the production of iohexol).
    Type: Grant
    Filed: February 7, 1997
    Date of Patent: October 20, 1998
    Assignee: Nycomed Imaging AS
    Inventors: David Redick Lane, Janis Vasilevskis
  • Patent number: 5637740
    Abstract: The reaction mixture obtained in the production of 2,3-epoxypropyltrialkylammonium chlorides by treatment of chlorohydroxypropyltrialkylammonium chlorides with alkaline acting materials in aqueous medium containing impurities which create problems in the subsequent use of the 2,3-epoxypropyltrialkylammonium chloride. According to the invention the reaction mixture is freed from these impurities by separating it from undissolved impurities by employing at least about 0.2 mole of 2,3-epoxypropyltrialkylammonium chloride per mole of water.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: June 10, 1997
    Assignee: Degussa Aktiengesellschaft
    Inventors: Wolfgang Fischer, Manfred Langer, Gert Roessler
  • Patent number: 5589554
    Abstract: An adhesive composition is here disclosed which comprises a 2-cyanoacrylate and at least one of compounds (a) and (b):(a) an addition reaction product of an epoxy group and a compound having a cyano group and a carboxylic acid group in its molecule, and(b) a compound having a cyano group and a carboxylic acid group in its molecule. A process for preparing the adhesive composition is also disclosed herein. According to the present invention, the 2-cyanoacrylate-based adhesive composition can be obtained which is excellent in storage stability and hardening properties of thick films and which has a high hardening rate and remarkably improved surface hardening properties of the adhesive composition itself bulged from between adherends. Particularly, the 2-cyanoacrylate bulged from between the adherends can harden rapidly, so that the vaporization of the 2-cyanoacrylate can be minimized.
    Type: Grant
    Filed: September 16, 1994
    Date of Patent: December 31, 1996
    Assignee: Three Bond Co., Ltd.
    Inventor: Soichiro Hiraoka
  • Patent number: 5532389
    Abstract: A process of preparing alkylene oxides comprises steps of: (1) optionally forming a hypochlorite solution; (2) contacting chlorine with a solution of a hypochlorite below about 60.degree. C., and a pH of less than about 5.5, with sufficient micromixing to achieve a product hypochlorous acid in a yield of at least about 80 percent; (3) separating at least a portion the hypochlorous acid from an aqueous metal chloride solution wherein the solution is sprayed as droplets; (4) distilling the remaining liquid phase; (5) absorbing the hypochlorous acid and dichlorine monoxide in low-chlorides water to produce a low-chlorides aqueous hypochlorous acid solution; (6) contacting the low-chlorides aqueous hypochlorous acid solution with an olefin in a continuous process to form a olefin chlorohydrin; (7) optionally contacting the olefin chlorohydrin with a base to form a alkylene oxide and a salt solution; and (8) optionally separating the alkylene oxide from the salt solution.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: July 2, 1996
    Assignee: The Dow Chemical Company
    Inventors: David L. Trent, George J. Quarderer, Kim G. Bargeron, Douglas C. Greminger, David J. Koranek, Erik J. Stewart, Curtis N. Swisher, Cheryl A. Tirtowidjojo, Danil Tirtowidjojo
  • Patent number: 5523425
    Abstract: In a process for producing a chlorohydrin an olefinically unsaturated compound is reacted with chlorine in the presence of water. Water is applied as a film on a solid support in a reaction zone and/or water droplets are dispersed in the reaction zone. The reaction is conducted at a pressure of up to about 10 bar.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: June 4, 1996
    Assignee: The Dow Chemical Company
    Inventors: Gunther A. Pech, Werner J. Witzl
  • Patent number: 5486627
    Abstract: Described herein is a method for producing epoxides which is continuous, inhibits formation of chlorinated byproducts, and eliminates or substantially reduces waste water discharge. The method includes:(a) forming a low chlorides aqueous hypochlorous acid solution;(b) contacting the low chlorides aqueous hypochlorous acid solution with at least one unsaturated organic compound to form an aqueous organic product comprising at least olefin chlorohydrin;(c) contacting at least the olefin chlorohydrin with an aqueous alkali metal hydroxide to form an aqueous salt solution product containing at least epoxide; and(d) isolating the epoxide from the aqueous salt solution;wherein water is recovered from the product of at least Step (b) and recycled into Step (a) for use in forming the low chlorides aqueous hypochlorous acid solution.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: January 23, 1996
    Assignee: The Dow Chemical Company
    Inventors: George J. Quarderer, Jr., Curtis N. Swisher, David L. Trent
  • Patent number: 5466764
    Abstract: There are here disclosed an adhesive composition obtained by adding a fluorine-containing carboxylic acid epoxy adduct to a 2-cyanoacrylate, and a process for preparing the adhesive composition. This 2-cyanoacrylate-based adhesive composition is excellent in storage stability and particularly excellent in adhesive force and impact resistance and has a high hardening rate. In particular, the adhesive strength of the 2-cyanoacrylate-based adhesive composition can be remarkably increased without lowering the hardening rate, and so the 2-cyanoacrylate-based adhesive composition can exert a sufficient resistance to impact and the like at the time of the adhesion of metals, rubbers, plastics and lumbers and the reliability of adherends can be improved.
    Type: Grant
    Filed: September 16, 1994
    Date of Patent: November 14, 1995
    Assignee: Three Bond Co., Ltd.
    Inventor: Soichiro Hiraoka
  • Patent number: 5428180
    Abstract: A method is provided for oxidizing alkenes to epoxides by treating the alkene with a transition metal ion complex which includes a salen or salophen derivative and peroxymonosulfate ion or hypochlorite ion in a two phase system with a phase transfer catalyst, a water phase having a pH from about 6 to about 12.9 and an inorganic solvent phase in which the complex is sufficiently soluble.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: June 27, 1995
    Assignee: The Research Foundation of State University of New York
    Inventors: Cynthia Burrows, Thomas R. Wagler, Heungsik Yoon
  • Patent number: 5344945
    Abstract: Process for the production of epichlorohydrin in which the chloroaliphatic impurities formed at the hypochlorination of allyl chloride to dichloropropanols are removed from the crude aqueous solution of dichloropropanols before dehydrochlorination, by extraction with a recycled organic solvent which is rich in 1,2,3-trichloropropane.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: September 6, 1994
    Assignee: Solvay (Societe Anonyme)
    Inventor: Frans Grunchard
  • Patent number: 5245048
    Abstract: A process for the production of a glycidyl ether of an alcohol, comprising reacting an alcohol with epichlorohydrin, in substantially the stoichiometric proportions required to produce the 1:1 adduct, in the presence, as catalyst, of a salt of perchloric acid or trifluoromethane sulphonic acid with a metal of Group IIIA of the Periodic Table of Elements (according to the IUPAC 1970 convention); and then dehydrochlorinating the product so obtained.
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: September 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: William M. Rolfe, Michael R. Thoseby
  • Patent number: 5245057
    Abstract: A continuous horizontal reactor system and process for employing such a system. In one embodiment, a reactor system having a cylindrical multi-compartment vessel, the compartments intercommunicating via a common overhead space or separated spaces from which vapor with reaction product or by-products may be removed, and from which liquid effluent with reaction products or by-products may be removed and reactants and catalyst flowable into each compartment and agitators in each compartment. Such a reactor system for producing liquid epoxy resins. Processes using such a reactor to produce reaction products, e.g. liquid epoxy resins.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: September 14, 1993
    Assignee: The Dow Chemical Company
    Inventor: Robert P. Shirtum