By Dehydrohalogenation Of A Halohydrin Or By Reacting A Hypohalite Or Hypohalous Acid With An Ethylenically Unsaturated Compound At The Site Of Unsaturation Patents (Class 549/520)
  • Patent number: 8921584
    Abstract: A composition is provided that contains an intermediate for a water-soluble monomer, wherein this intermediate is suitable for producing a water-soluble polyalkylene glycol-type monomer that has a polymerizable terminal double bond, and suitable for the production of water-soluble polymer, and moreover allows the high-yield production of water-soluble polymer. A process of producing this composition and a water-soluble monomer-containing composition obtained therefrom are also provided. A water-soluble monomer is also provided that can be used as a starting material for a water-soluble polymer that even at high hardnesses exhibits an excellent capacity to capture metal ions such as the calcium ion and magnesium ion, an excellent anti-gelation performance, an excellent anti-soil redeposition performance, a better anti-dye transfer performance than in the past, and also an excellent compatibility with surfactants.
    Type: Grant
    Filed: December 3, 2010
    Date of Patent: December 30, 2014
    Assignee: Nippon Shokubai Co, Ltd
    Inventors: Atsuro Yoneda, Makoto Saito, Aki Tsukajima, Daisuke Michitaka, Mitsuaki Makino
  • Publication number: 20140371475
    Abstract: An object of the present invention is to provide a method for producing a sulfur-containing epoxy compound producing no scum-like insoluble matter. According to the present invention, a sulfur-containing halohydrin compound is dripped into and reacted with a mixed solvent containing an organic solvent and a basic compound to provide the method for producing the sulfur-containing epoxy compound. According to aspects of the present invention, the organic solvent is at least one type of compound selected from toluene and benzene, the basic compound is at least one type of compound selected from sodium hydroxide, potassium hydroxide and calcium hydroxide, and the reaction temperature is between ?5° C. and 30° C.
    Type: Application
    Filed: April 12, 2013
    Publication date: December 18, 2014
    Applicant: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takashi Aoki, Hiroshi Horikoshi
  • Publication number: 20140364635
    Abstract: The present disclosure provides a preparation method of glycidylester of tertiary carbonic acid. The synthesis is performed in two steps: first, the tertiary carbonic acid reacts with a halo substituted epoxide under a catalyst to produce tertiary carbonic halo substituted alcohol ester; after dehydrohalogenation of the halo substituted alcohol ester of tertiary carbonic acid, the glycidylester of tertiary carbonic acid is formed. In the first step of preparing the halo substituted alcohol ester of tertiary carbonic acid through synthesis, the reaction between the tertiary carbonic acid and the halo substituted epoxide is only performed in the existence of water and the catalyst, and the water comprises water added before the reaction. The present disclosure significantly increases the product output in the unit volume, and is particularly suitable for industrial production of glycidylester of tertiary carbonic acid having the low cost, high purity, low color and stable color.
    Type: Application
    Filed: December 26, 2012
    Publication date: December 11, 2014
    Applicant: Tianjin Sheild Specialty Chemicals Co., Ltd.
    Inventors: Lanbo Sun, Tao Yang, Honghai Li, Yingchun Lou
  • Publication number: 20140155638
    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: Application
    Filed: July 2, 2013
    Publication date: June 5, 2014
    Inventor: DENNIS M. BROWN
  • Patent number: 8664413
    Abstract: An epoxy compound of high-purity N,N,N?,N?-tetraglycidyl-3,4?-diaminodiphenyl ether is produced by: an addition reaction step of reacting 3,4?-diaminodiphenyl ether with epichlorohydrin in a polar protic solvent at 65 to 100° C. for 12 hours or longer to form N,N,N?,N?-tetrakis(3-chloro-2-hydroxypropyl)-3,4?-diaminodiphenyl ether; and a cyclization reaction step of reacting the N,N,N?,N?-tetrakis(3-chloro-2-hydroxypropyl)-3,4?-diaminodiphenyl ether with an alkali compound for dehydrochlorination.
    Type: Grant
    Filed: March 2, 2011
    Date of Patent: March 4, 2014
    Assignee: Toray Fine Chemicals Co., Ltd.
    Inventors: Michiya Ishikawa, Hidetoshi Kato, Jiro Nakatani, Atsuhito Arai, Hiroaki Sakata, Hiroshi Taiko
  • 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: 20130217901
    Abstract: The invention relates to a method of producing optically active 4-chloro-3-hydroxybutanal compound (2) by reacting chloroacetaldehyde with aldehyde compound (1) in the presence of optically active pyrrolidine compound (5). wherein each symbol is as defined in the specification.
    Type: Application
    Filed: October 19, 2011
    Publication date: August 22, 2013
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Yujiro Hayashi
  • Patent number: 8420871
    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: September 21, 2011
    Date of Patent: April 16, 2013
    Assignee: Solvay (Societe Anonyme)
    Inventors: Patrick Gilbeau, Ivan De Andolenko, Philippe Krafft, Freddy Gielen
  • Publication number: 20130012730
    Abstract: An epoxy compound of high-purity N,N,N?,N?-tetraglycidyl-3,4?-diaminodiphenyl ether is produced by: an addition reaction step of reacting 3,4?-diaminodiphenyl ether with epichloro-hydrin in a polar protic solvent at 65 to 100° C. for 12 hours or longer to form N,N,N?,N?-tetrakis(3-chloro-2-hydroxypropyl)-3,4?-diaminodiphenyl ether; and a cyclization reaction step of reacting the N,N,N?,N?-tetrakis(3-chloro-2-hydroxypropyl)-3,4?-diaminodiphenyl ether with an alkali compound for dehydrochlorination.
    Type: Application
    Filed: March 2, 2011
    Publication date: January 10, 2013
    Applicant: TORAY FINE CHEMICALS CO., LTD.
    Inventors: Michiya Ishikawa, Hidetoshi Kato, Jiro Nakatani, Atsuhito Arai, Hiroaki Sakata, Hiroshi Taiko
  • Patent number: 8338627
    Abstract: A process for producing epoxide, the process including contacting an organic phase including at least one halohydrin(s) with at least one aqueous phase including a base in a plug-flow mixer/reactor system to disperse the organic phase in the aqueous phase via a mixing device imparting a power-to-mass ratio of at least 0.2 W/kg to convert at least a portion of the at least one halohydrin to an epoxide.
    Type: Grant
    Filed: July 30, 2009
    Date of Patent: December 25, 2012
    Assignee: Dow Global Technologies LLC
    Inventors: William W. Fan, Christian D. Kneupper, Sascha Noormann, Ranate Patrascu, Bruce D. Hook, Charles W. Lipp, Michael D. Cloeter, Heinz Groenewald
  • Patent number: 8298500
    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: Grant
    Filed: January 22, 2009
    Date of Patent: October 30, 2012
    Assignee: Dow Global Technologies LLC
    Inventors: Christian D. Kneupper, Perry S. Basile, William W. Fan, Sascha Noormann
  • Patent number: 8039650
    Abstract: A diamine and an epihalohydrin are subjected to ring-opening addition reaction in the presence of water, to thereby produce a tetrahalohydrinamino compound (i.e., halohydrin compound). Thereafter, the halohydrin compound is reacted with an alkali metal hydroxide in the co-presence of a phase-transfer catalyst, to thereby allow cyclization reaction to proceed. An alkali metal halide by-produced during the cyclization reaction is dissolved in water and removed through phase separation. The resultant organic layer is washed with water for phase separation. Then, a crude tetraglycidylamino compound obtained by recovering unreacted epihalohydrin through evaporation is dissolved in an organic solvent and washed with water for phase separation. Subsequently, the organic solvent is recovered through evaporation under reduced pressure with heating, to thereby isolate a tetraglycidylamino compound (i.e., a product of interest).
    Type: Grant
    Filed: May 8, 2008
    Date of Patent: October 18, 2011
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hideharu Kurashima, Tsutomu Numoto, Jyunichi Hisae
  • 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
  • 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: 20110028683
    Abstract: A composition comprising glycerol and at least one cyclic oligomer of glycerol, a process for obtaining the composition, and its use in the manufacture of dichloropropanol and of derived products such as epichlorohydrin and epoxy resins.
    Type: Application
    Filed: March 31, 2009
    Publication date: February 3, 2011
    Applicant: SOLVAY S.A.
    Inventors: Patrick Gilbeau, Bruno Jestin
  • 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: 20100029958
    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: 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: 20090198041
    Abstract: The invention relates to a crude glycerol-based product comprising glycerol alkyl ethers, to a purification process comprising a treatment of evaporative concentration, of evaporative crystallization, of distillation, of fractional distillation, of stripping, or of liquid-liquid extraction and to the use of the purified product in the manufacture of dichloropropanol.
    Type: Application
    Filed: June 12, 2007
    Publication date: August 6, 2009
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart
  • Publication number: 20080200642
    Abstract: Process for preparing a chlorohydrin from a polyhydroxylated aliphatic hydrocarbon, from an ester of a polyhydroxylated aliphatic hydrocarbon or from a mixture thereof, and from a chlorinating agent, the chlorinating agent comprising at least one of the following compounds: nitrogen, oxygen, hydrogen, chlorine, an organic hydrocarbon compound, an organic halogen compound, an organic oxygen compound and a metal.
    Type: Application
    Filed: May 19, 2006
    Publication date: August 21, 2008
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventor: Philippe Krafft
  • Publication number: 20080194850
    Abstract: Process for preparing an epoxide, wherein a reaction medium resulting from the reaction of a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof with a chlorinating agent, the reaction medium containing at least 10 g of chlorohydrin per kg of reaction medium, is subjected to a subsequent chemical reaction without intermediate treatment.
    Type: Application
    Filed: May 19, 2006
    Publication date: August 14, 2008
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Valentine Smets
  • Publication number: 20080194851
    Abstract: Continuous process for producing a chlorohydrin, wherein a polyhydroxylated baliphatic 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: Application
    Filed: May 19, 2006
    Publication date: August 14, 2008
    Applicant: Solvay (Societe Anonyme)
    Inventor: Patrick Gilbeau
  • Publication number: 20080194849
    Abstract: Process for preparing a chlorohydrin, comprising the following steps: (a) a polyhydroxylated aliphatic hydrocarbon, an ester of a polyhydroxylated aliphatic hydrocarbon or a mixture thereof whose alkali metal and/or alkaline earth metal content is less than or equal to 5 g/kg, a chlorinating agent and an organic acid are reacted so as to give a mixture containing at least chlorohydrin and by-products (b) at least part of the mixture obtained in step (a) is subjected to one or more treatments in steps subsequent to step (a) (c) at least one of the steps subsequent to step (a) consists in oxidation at a temperature greater than or equal to 800° C.
    Type: Application
    Filed: May 19, 2006
    Publication date: August 14, 2008
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Valentine Smets
  • 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
  • Publication number: 20080154050
    Abstract: Process for preparing an epoxide, wherein halogenated ketones are formed as by-products and there is at least one treatment intended to remove at least part of the halogenated ketones formed.
    Type: Application
    Filed: May 19, 2006
    Publication date: June 26, 2008
    Applicants: Solvay (Societe Anonyme)
    Inventor: Patrick Gilbeau
  • Patent number: 7361790
    Abstract: Epichlorohydrin is produced from acetone by (1) chlorinating acetone to form monochloroacetone; (2) disproportionating the monochloroacetone in the presence of a platinum catalyst, a strong acid and preferably a chloride source (for example, added as a salt or from hydrolysis of monochloroacetone) and some water to produce acetone and 1,3-dichloroacetone; (3) hydrogenating the 1,3-dichloroacetone in the presence of a catalyst to produce 1,3-dichlorohydrin; and (4) cyclizing the 1,3-dichlorohydrin with a base to produce epichlorohydrin.
    Type: Grant
    Filed: March 24, 2005
    Date of Patent: April 22, 2008
    Assignee: Dow Global Technologies Inc.
    Inventors: Marvin L. Dettloff, Marty J. Null
  • Patent number: 7049388
    Abstract: A process for manufacturing an ?-dihydroxy derivative from an aryl allyl ether wherein such ?-dihydroxy derivative can be used to prepare an ?-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an ?-halohydrin intermediate produced from a halide substitution of an ?-dihydroxy derivative which has been obtained by a dihydroxylation reaction of an aryl allyl ether in the presence of an oxidant or in the presence of an oxidant and a catalyst.
    Type: Grant
    Filed: September 9, 2003
    Date of Patent: May 23, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Clinton J. Boriack, Zeng K. Liao, Thomas H. Kalantar
  • Patent number: 6849750
    Abstract: Disclosed are intermediates and processes for preparing epoxides of the formula: where R and PROT are defined herein. These epoxides are useful as intermediates in the production of biologically active compounds, i.e., in the production of pharmaceutical agents.
    Type: Grant
    Filed: April 23, 2002
    Date of Patent: February 1, 2005
    Assignee: Pharmacia & UpJohn Company LLC
    Inventor: Michael R. Reeder
  • Publication number: 20040259943
    Abstract: The present invention relates to a novel and efficient chemoenzymatic process of preparation of optically active trans alkyl phenylglycidates. The invention particularly discloses a novel process for the chemoenzymatic synthesis of two enantiomers of trans alkyl phenylglycidate i.e. alkyl(2S,3R)-phenylglycidate and alkyl(2R,3S)-phenylglycidate of formulae 7 and 8 respectively.
    Type: Application
    Filed: March 10, 2004
    Publication date: December 23, 2004
    Applicant: COUNCIL OF SCIENTIFIC AND INDUSTRIAL
    Inventors: Naveen Anand, Munish Kapoor, Subhash Chandra Taneja, Surrinder Koul, Rattan Lal Sharma, Ghulam Nabi Oazi
  • 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: 6667422
    Abstract: A process for preparing an &agr;-haloketone of the formula (1) where R1 is an optionally heteroatom-containing and optionally substituted hydrocarbon radical, R2 is a hydrogen, alkyl, aralkyl or aryl radical, and X is a halogen radical, by reacting a carboxylic acid derivative of the general formula (2) where L is a leaving group, with a mono- or dienolate of a silyl ester of the formula (3) where R3 and R4 are identical or different alkyl, aryl, alkenyl or aralkyl radicals; and hydrolyzing the reaction product immediately afterwards by adding acid and decarboxylating to (1). The product &agr;-haloketone may be reduced to the corresponding &agr;-haloalcohol.
    Type: Grant
    Filed: September 3, 2002
    Date of Patent: December 23, 2003
    Assignee: Consortium fuer Elektrochemische Industrie GmbH
    Inventors: Dieter Heldmann, Juergen Stohrer
  • Patent number: 6646102
    Abstract: A process for manufacturing an &agr;-dihydroxy derivative from an aryl allyl ether wherein such &agr;-dihydroxy derivative can be used to prepare an &agr;-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an &agr;-halohydrin intermediate produced from a halide substitution of an &agr;-dihydroxy derivative which has been obtained by a dihydroxylation reaction of an aryl allyl ether in the presence of an oxidant or in the presence of an oxidant and a catalyst.
    Type: Grant
    Filed: July 5, 2001
    Date of Patent: November 11, 2003
    Assignee: Dow Global Technologies Inc.
    Inventors: Clinton J. Boriack, Zeng K. Liao, Thomas H. Kalantar
  • Publication number: 20030171603
    Abstract: The invention concerns a process for the production of optically active epoxides useful as pharmaceutical intermediates, particularly in the field of HIV protease inhibitors. The optically active epoxides are produced in commercially acceptable yields from an optically active alcohols by a Mitsunobu reaction and a cyclisation step, preferably comprising an intermediate recrystallisation step. The stereochemistry of the alcohol is inverted during the Mitsunobu reaction to produce the desired epoxide.
    Type: Application
    Filed: January 10, 2003
    Publication date: September 11, 2003
    Inventor: David Edward Justice
  • Patent number: 6570028
    Abstract: Process for the manufacture of diglycidylesters of &agr;,&agr;′-branched dicarboxylic acids, comprising (a) the reaction of the &agr;,&agr;′-branched dicarboxylic acid with a halo substituted monoepoxide such as an epihalohydrin, in a 1.1-20 acid equivalent ratio relative to the &agr;,&agr;′-branched aliphatic dicarboxylic acid, optionally in the presence of water and water-miscible solvent, and in the presence of a catalyst in an amount of at most 45 mol % of the acid equivalent amount of the &agr;,&agr;′-branched aliphatic dicarboxylic acid, at a temperature in the range of from 30 to 110° C., during a period in the range of from 0.5 to 2.5 hr, (b) addition of alkali metal hydroxide or alkali metal alkanolate up to an acid equivalent ratio as to the &agr;,&agr;′-branched aliphatic dicarboxylic acid in the range of from 0.9:1 to 1.2:1, and reaction at a temperature of from 0 to 80° C.
    Type: Grant
    Filed: October 31, 2000
    Date of Patent: May 27, 2003
    Assignee: Resolution Performance Products LLC
    Inventors: Denis Marie Charles Heymans, Leo Wim Van Noort, Jozef Jacobus Titus Smits, Hendrik Stichter
  • Patent number: 6534621
    Abstract: A process for manufacturing an &agr;-halohydrin intermediate and an epoxy resin prepared therefrom including epoxidizing an &agr;-halohydrin intermediate produced from an in situ halide substitution-deesterification of an &agr;-hydroxy ester derivative which has been obtained by the coupling reaction of a phenol or a mixture of phenols and a glycidyl ester optionally in the presence of a catalyst.
    Type: Grant
    Filed: May 9, 2001
    Date of Patent: March 18, 2003
    Assignee: Dow Global Technologies Inc.
    Inventors: Clinton J. Boriack, Zeng K. Liao
  • Patent number: 6531549
    Abstract: A crystallized epoxy resin which is easy to blend with a hardener or the like is a crystallized product of an epoxy resin derived from 4,4′-dihydroxy-3,3′,5,5′-tetramethylbiphenyl and an epihalohydrin, and the ratio of an endotherm between 50° C. and 130° C. to an endotherm between 80° C. and 125° C., measured by raising the temperature at a rate of 10° C. per minute using a DSC device, is 1.03 or more.
    Type: Grant
    Filed: December 12, 2001
    Date of Patent: March 11, 2003
    Assignee: Japan Epoxy Resins Co., Ltd.
    Inventors: Yasuyuki Murata, Masayuki Tsutsumi, Kiyotaka Ikebata, Ken Tanaka
  • Patent number: 6525207
    Abstract: This invention provides a process for producing an epoxy compound industrially advantageously at low cost in a short process. Furthermore, this invention provides a novel fruity, camphoric, floral, amber or woody fragrance-, flavor- or scent-imparting composition containing said epoxy compound, and foods & drinks, perfumes, cosmetics and tobaccos containing said composition. The epoxy compound can be produced by letting an &agr;-halocyclododecanone and an organic magnesium compound react with each other for Grignard reaction, hydrolyzing to obtain a halohydrin and letting the halohydrin and a base react with each other in the presence of an phase transfer catalyst or adding an aprotic polar solvent for reaction.
    Type: Grant
    Filed: April 17, 2002
    Date of Patent: February 25, 2003
    Assignee: Soda Aromatic Co., Ltd.
    Inventors: Nobuhiko Ito, Motoo Higashi, Yuki Konno, Hideaki Takaoka
  • Publication number: 20020072621
    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: Application
    Filed: October 10, 2001
    Publication date: June 13, 2002
    Applicant: Ajinomoto Co., Inc.
    Inventors: Tomoyuki Onishi, Naoko Hirose, Yasuyuki Otake, Takashi Nakano, Yutaka Honda, Masakazu Nakazawa, Kunisuke Izawa
  • Patent number: 6316233
    Abstract: An industrial and economical method for obtaining a (S)-3-halogeno-1,2-propanediol, which comprises cultivating a microorganism belonging to the genus. Pseudomonas which has an ability to assimilate (R)-3-halogeno-1,2-propanediol and can grow by assimilating (R)-3-halogeno-1,2-propanediol as a single carbon source, in a culture medium containing a racemic 3-halogeno-1,2-propanediol as a substrate, and isolating the (S)-3-halogeno-1,2-propanediol from the culture medium.
    Type: Grant
    Filed: November 29, 2000
    Date of Patent: November 13, 2001
    Assignee: Daiso Co., Ltd.
    Inventors: Toshio Suzuki, Hideaki Idogaki, Atsushi Nakagawa, Naoya Kasai
  • Patent number: 6284902
    Abstract: This invention relates to a process for manufacturing an optically active (S)-3,4-epoxybutyric acid salt and more particularly, to a method for manufacturing (S)-3,4-epoxybutyric acid salt expressed by the following formula 1, wherein an optically active (S)-3-hydroxybutyrolactone is employed to undergo an economical ring-opening reaction and epoxvdation so that its chiral center is maintained in an original form, Wherein, R1 represents alkali metal atom, alkaline earth metal atom, alkylamine group or quarternary amine group.
    Type: Grant
    Filed: February 21, 2001
    Date of Patent: September 4, 2001
    Assignee: Samsung Fine Chemicals Co., Ltd.
    Inventors: Ho Sung Yu, Jae Young Bae, Yik Haeng Cho, Young Mi Park, Il Suk Byun
  • Patent number: 6278002
    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 or 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: Grant
    Filed: September 1, 2000
    Date of Patent: August 21, 2001
    Assignee: Kaneka Corporation
    Inventors: Kazumi Okuro, Kenji Inoue
  • Patent number: 6268533
    Abstract: A method is disclosed for the preparation of optically pure isomers of formoterol by the reaction of an optically pure 4-benzyloxy-3-formamidostyrene oxide with an optically pure 4-methoxy-&agr;-methyl-N-(phenylmethyl)benzeneethanamine followed by debenzylation. Useful intermediates in the process are also disclosed, as are the novel L-tartrate salt of R,R-formoterol and pharmaceutical compositions thereof.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: July 31, 2001
    Assignee: Sepracor Inc.
    Inventors: Yun Gao, Robert Hett, Kevin Q. Fang, Stephen A. Wald, Chris Hugh Senanayake
  • Patent number: 6160136
    Abstract: A compound having the formula: ##STR1## wherein: R is fluorine, hydrogen, an unsubstituted or substituted aliphatic or unsubstituted or substituted aromatic radical;R.sub.1 is an unsubstituted or substituted aliphatic radical, or unsubstituted or substituted aromatic radical; andR.sub.2 is hydrogen, an unsubstituted or substituted aliphatic radical, or unsubstituted or substituted aromatic radical.
    Type: Grant
    Filed: December 13, 1999
    Date of Patent: December 12, 2000
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Haridasan K. Nair
  • 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: 5929284
    Abstract: Processes for efficiently producing .alpha.-halo ketones, .alpha.-halohydrins and epoxides on an industrial scale. The prosesses include one for producing an .alpha.-halo ketone of general formula (3) by decarboxylating a product of reaction between a carboxilic acid derivative of general formula (1) and a metal enolate prepared from an .alpha.-haloacetic acid of general formula (2) or an acceptable salt thereof, one for producing an by reducing the .alpha.-halo ketone (3), and one for producing an epoxide (13) by treating the .alpha.-halohydrin (11) with a base to effect ring closure. The above prosesses are particularly suitable for producing optically active .alpha.-halo ketones, .alpha.-halohydrins and epoxides from the corresponding .alpha.-amino acid derivatives.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: July 27, 1999
    Assignee: Kaneka Corporation
    Inventors: Akira Nishiyama, Tadashi Sugawa, Hajime Manabe, Kenji Inoue, Noritaka Yoshida
  • 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: 5451689
    Abstract: There is provided a method of preparing an epoxide (1a) or (1b) shown below: ##STR1## where R.sup.1, R.sup.2, R.sup.3, and R.sup.4 represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, an alkoxy group, an aryloxy group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, allalkyl group, a silyl group, and a silyloxy group; the groups may be bonded with each other to form rings in the case where these groups can be bivalent; these groups may be the same or different, may have substituting groups, or may be branched; and each form (isomer) has a structure in which one side of the plane constituted by double bonds, R.sup.1, R.sup.2, R.sup.3 and R.sup.4, is more seterically hindered in comparison with the other side;characterized in that:an olefin represented by the formula (2) below, is reacted with iodine in the presence of compound generating acyloxy ion, ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: September 19, 1995
    Assignee: Japan Tobacco, Inc.
    Inventors: Katsuya Matsumoto, Takashi Ebata, Koshi Koseki, Koji Okano, Hiroshi Kawakami, Hajime Matsushita
  • 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: 5239093
    Abstract: The present invention relates to the preparation of di-secondary alcohols comprising the reaction of an alcohol and a diglycidyl ether of a dihydric phenol in the presence of a catalyst of the formula (IV):MX (IV)wherein M is a metal from Groups IB to VIIIB or a metal or metalloid from Groups IIA to VA of the Periodic Chart of Elements or an ammonium ion or H.sup.+ or a hydronium ion and X is an anion selected from the group consisting of BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, AlF.sub.4.sup.-, TiF.sub.6.sup.2-, SiF.sub.6.sup.2- and ZrF.sub.6.sup.2- to produce the di-secondary alcohol, which can then be subjected to glycidylation to produce a glycidyl ether; orthe reaction of an alcohol or diol and epichlorohydrin in the presence of the foregoing catalyst, followed by ring closure employing an alkali to produce a mono- or polyglycidyl ether.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: August 24, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Chi-Wen F. Cheng
  • Patent number: 5149841
    Abstract: A process for the preparation of compounds of the formula I ##STR1## in which R is glycidyl, R.sub.1 and R.sub.3 independently of one another are C.sub.1 -C.sub.6 alkyl and R.sub.2 and R.sub.4 independently of one another are hydrogen or methyl, wherein(i) a diamine of the formula II ##STR2## in which R.sub.1,R.sub.2,R.sub.3 and R.sub.4 are as defined above, is reacted with epichlorohydrin in a molar ratio of 1:12 to 1:40 at a temperature of 80.degree. to 115.degree. C. and(ii) a phase transfer catalyst is mixed with the reaction mixture, the epichlorohydrin is subjected to distillation while being circulated and at the same time the dehydrochlorination is carried out with the addition of a concentrated, aqueous alkali metal of alkaline earth metal hydroxide solution and simultaneous removal of the water distilled off azeotropically.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: September 22, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Werner Schaffner
  • Patent number: 5126464
    Abstract: A 13 or 14 member macrocyclic compound having the following ring nucleus: ##STR1## wherein: n=0 or 1;m=0 or 1;n+m>0;X.sub.1, X.sub.2, Z.sub.1 and Z.sub.2 independently represent H.sub.2 or O;Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 independently represent H, lower alkyl or CH.sub.2 COOH;L.sub.1 and L.sub.2 independently represent side chains of alpha amino acids, except that L.sub.1 and L.sub.2 do not both represent H; andR.sub.1 and R.sub.2 independently represent H or OH forms stable complexes with transition metal ions that may be used as catalysts for oxidizing alkenes to epoxides with oxidizing agents.
    Type: Grant
    Filed: October 29, 1990
    Date of Patent: June 30, 1992
    Assignee: The Research Foundation of State University of New York
    Inventors: Cynthia Burrows, Thomas R. Wagler, Heungsik Yoon