Processes Patents (Class 560/96)
  • Patent number: 9018408
    Abstract: The present invention generally relates to a condensed process for producing terephthalic acid and terephthalic esters from a dialkyl cyclohexane-2,5-dione-1,4-dicarboxylate; a chemoselective process for preparing a substantially bicyclic-lactone-free dialkyl cyclohexane-2,5-diol-1,4-dicarboxylate; and compositions of matter prepared thereby.
    Type: Grant
    Filed: January 10, 2012
    Date of Patent: April 28, 2015
    Assignee: Dow Global Technologies LLC
    Inventors: William Kruper, Jr., Cynthia L. Rand, David C. Molzahn
  • Publication number: 20150025263
    Abstract: 3,4-Dicarboalkoxybiphenyl-3?,4?-dicarboxylic acid represented by the general formula (1): in which R11 and R12 each represents an alkyl group having 1 to 4 carbon atoms, and n represents the number of waters of hydration that is 0 or 1, and the corresponding anhydride.
    Type: Application
    Filed: October 1, 2014
    Publication date: January 22, 2015
    Inventors: Yasushi Yamamoto, Yasutaka Yoshida, Hikaru Yatabe, Yoshihiro Yamauchi, Tetsurou Tsuji
  • Publication number: 20150025186
    Abstract: Disclosed are a method for preparing an ester plasticizer and an ester plasticizer prepared by the method. More specifically, disclosed are a method for preparing an ester plasticizer comprising trans-esterifying 100 parts by weight of dioctyl terephthalate with 0.1 to 89.9 parts by weight of butyl alcohol, and an ester plasticizer prepared by the method. Advantageously, provided are a novel method for preparing an ester plasticizer and an ester plasticizer with superior physical properties, prepared by the method.
    Type: Application
    Filed: October 9, 2014
    Publication date: January 22, 2015
    Inventors: Hyun Kyu KIM, Da Won JUNG, Mi Yeon LEE, Dong Hyun KO
  • Publication number: 20140364631
    Abstract: The present disclosure is related to silica-based Lewis acid catalysts, being essentially devoid of strong Brønsted acid character, and their ability to effect the [4+2] cycloaddition and dehydrative aromatization of dienes and dienophiles containing oxygenated substituents to form substituted benzene products. In some embodiments, the processes comprise contacting biomass-derived substrates with ethylene to form terephthalic acid and its derivatives.
    Type: Application
    Filed: May 20, 2014
    Publication date: December 11, 2014
    Inventors: MARK E. DAVIS, JOSHUA PACHECO
  • Patent number: 8871966
    Abstract: A method for preparing 1,4-biscarboxylic acid esters of benzene is provided.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: October 28, 2014
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: George A. Kraus, Jennifer J. Lee
  • Publication number: 20140275608
    Abstract: A method for preparing 1,4-biscarboxylic acid esters of benzene is provided.
    Type: Application
    Filed: March 15, 2013
    Publication date: September 18, 2014
    Inventors: George A. Kraus, Jennifer J. Lee
  • Patent number: 8772529
    Abstract: A catalyst for alkylation contains an inorganic structural material having an ion-exchange ability and a metal ion having a valency of 2 or more. The metal ion is supported on the inorganic structural material. The inorganic structural material is preferably a zeolite. The metal ion is preferably a lanthanide metal. The catalyst for alkylation imparts industrially satisfiable activity and selectivity and can be readily separated, collected and recycled. Furthermore, the process for producing an alkylaromatic hydrocarbon compound includes reacting an aromatic hydrocarbon compound and a compound having an unsaturated bond in the presence of the catalyst for alkylation.
    Type: Grant
    Filed: June 3, 2011
    Date of Patent: July 8, 2014
    Assignee: UBE Industries, Ltd
    Inventors: Yasushi Yamamoto, Hikaru Yatabe
  • Publication number: 20140155632
    Abstract: The invention relates to a process for preparing aryl- and heteroarylacetic acids and derivatives thereof by reaction of aryl or heteroaryl halides with malonic diesters in the presence of a palladium catalyst, of one or more bases and optionally of a phase transfer catalyst. This process enables the preparation of a multitude of functionalized aryl- and heteroarylacetic acids and derivatives thereof, especially also the preparation of arylacetic acids with sterically demanding substituents.
    Type: Application
    Filed: February 27, 2012
    Publication date: June 5, 2014
    Inventors: Thomas Himmler, Lukas J. Goossen, Felix Rudolphi, Bingrui Song
  • Publication number: 20130345467
    Abstract: The present invention generally relates to a condensed process for producing terephthalic acid and terephthalic esters from a dialkyl cyclohexane-2,5-di-one-1,4-dicarboxylate; a chemoselective process for preparing a substantially bicyclic-lactone-free dialkyl cyclohexane-2,5-diol-1,4-dicarboxylate; and compositions of matter prepared thereby.
    Type: Application
    Filed: January 10, 2012
    Publication date: December 26, 2013
    Inventors: William Kruper, JR., Cynthia L. Rand, David C. Molzahn
  • Publication number: 20130041174
    Abstract: A catalyst for alkylation contains an inorganic structural material having an ion-exchange ability and a metal ion having a valency of 2 or more. The metal ion is supported on the inorganic structural material. The inorganic structural material is preferably a zeolite. The metal ion is preferably a lanthanide metal. The catalyst for alkylation imparts industrially satisfiable activity and selectivity and can be readily separated, collected and recycled. Furthermore, the process for producing an alkylaromatic hydrocarbon compound includes reacting an aromatic hydrocarbon compound and a compound having an unsaturated bond in the presence of the catalyst for alkylation.
    Type: Application
    Filed: June 3, 2011
    Publication date: February 14, 2013
    Applicant: UBE INDUESTRIES, LTD.
    Inventors: Yasushi Yamamoto, Hikaru Yatabe
  • Patent number: 8367858
    Abstract: The present invention relates to novel substituted and unsubstituted terephthalic acid and carboxylate derivatives and products prepared therefrom having a significant renewable content. The invention also relates to processes for preparing substituted and unsubstituted terephthalic and carboxylate derivatives thereof wherein a portion of the starting materials utilized is derived from renewable resources. The invention also relates to novel cyclohexene based intermediates prepared in these processes and to conversion of these intermediates to substituted and unsubstituted cyclohexane-1,4-dicarboxylates and carboxylate derivatives thereof and novel forms of the resulting products having renewable content. The invention also relates to products prepared from substituted and unsubstituted terephthalic acid and carboxylate derivatives thereof derived from starting materials derived from renewable resources.
    Type: Grant
    Filed: June 16, 2010
    Date of Patent: February 5, 2013
    Assignee: Amyris, Inc.
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui, Douglas A. Wicks
  • Publication number: 20110288311
    Abstract: The present invention relates to novel substituted and unsubstituted terephthalic acid and carboxylate derivatives and products prepared therefrom having a significant renewable content. The invention also relates to processes for preparing substituted and unsubstituted terephthalic and carboxylate derivatives thereof wherein a portion of the starting materials utilized is derived from renewable resources. The invention also relates to novel cyclohexene based intermediates prepared in these processes and to conversion of these intermediates to substituted and unsubstituted cyclohexane-1,4-dicarboxylates and carboxylate derivatives thereof and novel forms of the resulting products having renewable content. The invention also relates to products prepared from substituted and unsubstituted terephthalic acid and carboxylate derivatives thereof derived from starting materials derived from renewable resources.
    Type: Application
    Filed: June 16, 2010
    Publication date: November 24, 2011
    Applicant: Draths Corporation
    Inventors: John W. Frost, Adeline Miermont, Dirk Schweitzer, Vu Bui, Douglas A. Wicks
  • Patent number: 8034970
    Abstract: Methods and systems for the production of phthalic acid diesters are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and mixing of a phthalic acid derivative with alcohol. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time with existing catalysts.
    Type: Grant
    Filed: June 23, 2008
    Date of Patent: October 11, 2011
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Publication number: 20110213116
    Abstract: The invention provides methods and systems for manufacturing low-acid polyalkylene terephthalate, for example, polybutylene terephthalate (PBT). The invention also provides methods and systems for preparing macrocyclic polyester oligomer (MPO) from low-acid polyalkylene terephthalate. Finally, the invention provides methods and systems for preparing MPO via reaction of a diol and a dialkyl ester in an organic solvent to form non-isolated, low-acid polyalkylene terephthalate which undergoes cyclization (depolymerization) to form MPO.
    Type: Application
    Filed: July 29, 2010
    Publication date: September 1, 2011
    Inventors: Peter D. Phelps, Gary R. Faler
  • Publication number: 20110009548
    Abstract: Oxo-diesters of cyclic olefins, methods of making them and their use as plasticizers in polymer compositions are disclosed.
    Type: Application
    Filed: July 6, 2010
    Publication date: January 13, 2011
    Applicant: ExxonMobil Research and Engineering Company
    Inventors: Jihad Mohammed DAKKA, Edmund Joseph Mozeleski, Lisa Saunders Baugh, Allen David Godwin, Diana S. Smirnova
  • Publication number: 20100168441
    Abstract: Disclosed is a process for production of a substituted benzene, which comprises intramolecularly and/or intermolecularly trimerizing a triple bond in an alkyne in the presence of a transition metal catalyst to yield a substituted benzene compound. In the process, the transition metal catalyst is prepared from an iminomethylpyridine represented by the formula (1) or (2), a transition metal salt or a hydrate thereof, and a reducing agent in a reaction system and is used to perform the trimerization. The process can be used in any one of the intramolecular cyclization of a triyne compound, the cyclization of a diyne compound or an alkyne compound and the intermolecular cyclization of three molecules of an alkyne compound, is excellent in economic effectiveness and operability, and is practically advantageous.
    Type: Application
    Filed: January 9, 2007
    Publication date: July 1, 2010
    Inventor: Sentaro Okamoto
  • Publication number: 20100137630
    Abstract: Acetals are formed from an aldehyde hydrogenation product mixture comprising alcohols and at most 2% of alde-hydes and the product is distilled to yield purified alcohols and a second stream containing acetals and/or unsaturated ethers.
    Type: Application
    Filed: February 27, 2008
    Publication date: June 3, 2010
    Inventors: Ronald Dean Garton, Corey W. Reed, Rao Krishna Kulai, Bruce D. Lilly, Ramzi Yanni Saleh, Raphael Frans Caers
  • Patent number: 7696125
    Abstract: A catalyst and a process for preparing carboxylic acid esters from an aldehyde and an alcohol in the presence of molecular oxygen are disclosed. The catalyst comprises metals supported on a silica-containing support, wherein the metals consist essentially of palladium, lead, an alkali or alkaline earth metal, and at least one of niobium and zirconium. The process for preparing a carboxylic acid ester comprises reacting an aldehyde with an alcohol in the presence of molecular oxygen and the aforementioned catalyst.
    Type: Grant
    Filed: July 6, 2005
    Date of Patent: April 13, 2010
    Assignee: Lee Chang Yung Chemical Industry Corporation
    Inventors: Kindtoken Hwaider Liu, Man-Yin Lo, Wen-Chyi Lin, Mei-Yuan Chang
  • Publication number: 20100056820
    Abstract: The present invention relates to a process for preparing substituted 2-arylmalonic esters of the general formula I in which R is C1-C6-alkyl or C1-C4-alkoxy-C1-C4-alkyl; Ar is phenyl or a heteroaromatic 5- or 6-membered ring; where each carbon atom present in the radicals mentioned above optionally carries a substituent RA; RA is F, Cl, CN, NO2, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, etc., or two adjacent substituents RA together with the carbon atoms to which they are attached form a ring; and where a malonic ester is reacted with a base and an aryl bromide in the presence of a copper salt, which comprises employing from 0.1 to 0.65 molar equivalents of the base per molar equivalent of the malonic ester.
    Type: Application
    Filed: January 21, 2008
    Publication date: March 4, 2010
    Applicant: BASF SE
    Inventors: Volker Maywald, Christian Ott, Bernd Wolf, Manfred Ehresmann, Michael Rack, Michael Keil, Sebastian Peer Smidt
  • Publication number: 20090281348
    Abstract: The present invention relates to a method of regenerating a ruthenium catalyst suitable for hydrogenation, which comprises flushing the catalyst with inert gas in a regeneration step until the original activity or part of the original activity has been attained. The method is particularly useful for ruthenium catalysts which are used for the hydrogenation of aromatics.
    Type: Application
    Filed: July 18, 2007
    Publication date: November 12, 2009
    Applicant: BASF SE
    Inventors: Jochem Henkelmann, Michael Becker, Daniela Mirk, Felix Richter, Thomas Schäfer
  • Publication number: 20090275772
    Abstract: An object of the present invention is to provide a method capable of producing a 1,2-phenylethane compound with extremely high yield in a short amount of time.
    Type: Application
    Filed: March 16, 2007
    Publication date: November 5, 2009
    Inventor: Takeshi Niitani
  • Publication number: 20090216017
    Abstract: A process for producing a biaryl compound, characterized by reacting an arylhydrazine compound, hydrogen peroxide and an aryl compound. When the reaction is conducted in the presence of a given metal or a compound of the metal or in the presence of a metal oxide obtained by reacting the given metal or a compound of the metal with hydrogen peroxide, then the yield of the biaryl compound is improved.
    Type: Application
    Filed: May 1, 2009
    Publication date: August 27, 2009
    Inventor: Koji HAGIYA
  • Publication number: 20090143595
    Abstract: A process for the preparation of a multi-dimensional microporous metal-organic compound comprising the steps of providing a first reactant which includes at least one metal in ionic form, providing a second reactant which includes a bridging organic ligand, grinding the first and second reactants together, wholly or substantially in the absence of solvent.
    Type: Application
    Filed: August 25, 2006
    Publication date: June 4, 2009
    Applicant: The Queen's University of Belfast
    Inventors: Stuart Lloyd James, Ana Lazuen-Garay, Anne Pichon
  • Patent number: 7425603
    Abstract: A polymer comprising structural units derived from a polycyclic dihydroxy compound of Formula (I) wherein R1, R2 and R3 are independently at each occurrence selected from the group consisting of a cyano functionality, a halogen, an aliphatic functionality having 1 to 10 carbons, a cycloaliphatic functionality having 3 to 10 carbons, and an aromatic functionality having 6 to 10 carbons; wherein each occurrence of “n”, “m”, and “p” independently has a value of 0, 1, 2, 3, or 4; and wherein the polymer is substantially linear.
    Type: Grant
    Filed: November 29, 2005
    Date of Patent: September 16, 2008
    Assignee: General Electric Company
    Inventors: T. Tilak Raj, Radhakrishna Arakali Srinivasarao, Jan-Pleun Lens, Subrahmanya Bhat K., Umesh Hasyagar, Subash Scindia
  • Publication number: 20080154035
    Abstract: The present invention relates to a coupling method between intramolecular carbon using the intramolecular cyclization reaction in situ of an allyl-indium compound derived from an allyl derivative containing an unsaturated hydrocarbon compound and indium, in presence of a transition metal compound catalyst. More particularly, the present invention relates to a coupling method between intramolecular carbon for preparing a cyclic compound having a vinyl group as a substituent by bonding a carbon in an allyl derivative containing an unsaturated hydrocarbon compound and a carbon in the unsaturated hydrocarbon compound via intramolecular cyclization reaction in situ of an allyl-indium compound as a coupling agent derived from the allyl derivative containing the unsaturated hydrocarbon and indium (In), in presence of a palladium catalyst.
    Type: Application
    Filed: July 17, 2007
    Publication date: June 26, 2008
    Applicant: PHIL HO LEE
    Inventors: Phil Ho LEE, Kooyeon LEE, Dong SEOMOON, Hyunseok KIM
  • Publication number: 20080132672
    Abstract: A composition and a process for producing an ester or polyester are provided. The composition comprises a titanium compound and clay or a dispersion of clay. The process comprises contacting a carbonyl compound, in the presence of a catalyst, with a glycol in which the catalyst comprises a titanium compound and clay or a dispersion of clay.
    Type: Application
    Filed: February 4, 2008
    Publication date: June 5, 2008
    Applicant: E.I. du Pont de Nemours and company
    Inventor: Donald Edward Putzig
  • Patent number: 7381786
    Abstract: Disclosed herein is a process for preparing a polymer comprising structural units derived from polycyclic dihydroxy compound having Formula (I), wherein R1 is selected from the group consisting of a cyano functionality, a nitro functionality, an aliphatic functionality having 1 to 10 carbons, an aliphatic ester functionality having 2 to 10 carbons, a cycloaliphatic ester functionality having 4 to 10 carbons and an aromatic ester functionality having 4 to 10 carbons; R2 is selected from the group consisting of a cyano functionality, a nitro functionality, an aliphatic ester functionality having 2 to 10 carbons, a cycloaliphatic ester functionality having 4 to 10 carbons and an aromatic ester functionality having 4 to 10 carbons; and each R3 and R4, at each occurrence, can be the same or different and are independently at each occurrence an aliphatic functionality having 1 to 10 carbons or a cycloaliphatic functionality having 3 to 10 carbons, “n” is an integer having a value 0 to 4 and “m” is an integer ha
    Type: Grant
    Filed: March 29, 2007
    Date of Patent: June 3, 2008
    Assignee: General Electric Company
    Inventors: Jan Henk Kamps, Jan-Pleun Lens, James A. Mahood, Arakali Srinivasarao Radhakrishna, T. Tilak Raj, Ravindra Vikram Singh
  • Patent number: 7361779
    Abstract: Mixtures of terephthalate diesters having lowered freezing points and methods of making the terephthalic acid diesters. The method includes contacting a first alcohol, a second different alcohol and dimethyl terephthalate in the presence of a catalyst to thereby form the terephthalate diesters.
    Type: Grant
    Filed: April 18, 2007
    Date of Patent: April 22, 2008
    Assignee: Eastman Chemical Company
    Inventors: Mark Holt, Phillip Wayne Turner, Steven Leroy Cook, Martin James Stimpson
  • Patent number: 7326763
    Abstract: A polymer comprises structural units derived from a polycyclic dihydroxy compound of Formula (I) wherein R1 is selected from the group consisting of a cyano functionality, a nitro functionality, an aliphatic functionality having 1 to 10 carbons, an aliphatic ester functionality having 2 to 10 carbons, a cycloaliphatic ester functionality having 4 to 10 carbons and an aromatic ester functionality having 4 to 10 carbons; R2 is selected from the group consisting of a cyano functionality, a nitro functionality, an aliphatic ester functionality having 2 to 10 carbons, a cycloaliphatic ester functionality having 4 to 10 carbons and an aromatic ester functionality having 4 to 10 carbons; and R3 and R4 are independently at each occurrence a hydrogen, an aliphatic functionality having 1 to 10 carbons or a cycloaliphatic functionality having 3 to 10 carbons.
    Type: Grant
    Filed: October 28, 2005
    Date of Patent: February 5, 2008
    Assignee: General Electric Company
    Inventors: Jan Henk Kamps, Jan-Pleun Lens, James A. Mahood, Radhakrishna Arakali Srinivasarao, T. Tilak Raj, Ravindra Vikram Singh
  • Patent number: 7307183
    Abstract: A method for preparing tetrabromobenzoate ester from a tetrabromophthalic anhydride including the steps of reacting the tetrabromophthalic anhydride with a catalyst and an alcohol at a temperature that favors partial esterification over complete esterification of the tetrabromophthalic anhydride to form a tetrabromophthalate half-ester reaction mixture; and feeding the half-ester reaction mixture to at least one reactor having and maintaining a temperature that favors decarboxylation over esterification to produce a tetrabromobenzoate ester-containing product. The temperature favoring partial esterification of the tetrabromophthalic anhydride is between about 70° C. and 130° C. The temperature favoring decarboxylation over esterification is between about 190° C. and 205° C. The tetrabromobenzoate ester-containing product comprises at least about 85% tetrabromobenzoate ester. The at least one reactor may include two or more reactors connected to one another in series.
    Type: Grant
    Filed: July 29, 2003
    Date of Patent: December 11, 2007
    Assignee: Great Lakes Chemical Corporation
    Inventors: David W. Bartley, James D. Siebecker, Stephen B. Falloon
  • Patent number: 7271281
    Abstract: 2,3,3?,4?-Biphenyltetracarboxylic acid tetraester is predominantly produced by a process in which a phthalic acid diester is subjected to oxidative-coupling reaction in the presence of molecular oxygen and a catalyst comprising a rhodium-containing compound.
    Type: Grant
    Filed: October 25, 2004
    Date of Patent: September 18, 2007
    Assignee: Ube Industries, Ltd.
    Inventors: Tetsuro Tsuji, Yasushi Yamamoto, Shinji Yasuda
  • Patent number: 7247742
    Abstract: A process for preparing a dialkylester of a naphthalenedicarboxylic acid comprising directing a liquid phase reaction mixture comprising a low molecular weight alcohol, a naphthalenedicarboxylic acid, a dialkylester of a naphthalenedicarboxylic acid, and a polyethylene naphthalate containing material, at a given temperature and pressure through series arranged reaction zones and subsequently removing a product comprising a dialkylester formed by the reaction of the naphthalenedicarboxylic acid and the polyethylene naphthalate containing material with the low molecular weight alcohol from a reaction zone. This invention is also directed to a process for preparing a purified dialkylester of a naphthalenedicarboxylic acid comprising a series of crystallization and distillation steps, and combinations thereof.
    Type: Grant
    Filed: May 20, 2004
    Date of Patent: July 24, 2007
    Assignee: BP Corporation North America Inc.
    Inventors: Rosemary F. McMahon, John A. Macek, Gregory P. Hussmann, Michael J. Panzer, Raymond J. Eifert, David A. Young, Allen B. Mossman, J. Deven Cleckler
  • Patent number: 7208620
    Abstract: A dihydroxy aromatic compound having a Formula (I) wherein R1 is selected from the group consisting of a cyano functionality, a nitro functionality, an aliphatic functionality having 1 to 10 carbons, an aliphatic ester functionality having 2 to 10 carbons, a cycloaliphatic ester functionality having 4 to 10 carbons and an aromatic ester functionality having 4 to 10 carbons; R2 is selected from the group consisting of a cyano functionality, a nitro functionality, an aliphatic ester functionality having 2 to 10 carbons, a cycloaliphatic ester functionality having 4 to 10 carbons and an aromatic ester functionality having 4 to 10 carbons; and each R3 and R4, at each occurrence, can be the same or different and are independently at each occurrence an aliphatic functionality having 1 to 10 carbons or a cycloaliphatic functionality having 3 to 10 carbons, “n” is an integer having a value 0 to 4 and “m” is an integer having a value 0 to 4.
    Type: Grant
    Filed: October 28, 2005
    Date of Patent: April 24, 2007
    Assignee: General Electric Company
    Inventors: Jan Henk Kamps, Jan-Pleun Lens, A. S. Radhakrishna, T. Tilak Raj, Ravindra Vikram Singh
  • Patent number: 7030264
    Abstract: Bis-?-hydroxyethyl terephthalate having an optical density measured in a 10 wt % methanol solution at a measurement wavelength of 380 nm and a cell optical path length of 10 mm of 0.000 to 0.006. The present invention makes it clear that purified BHET having an optical density of 0.006 or less provides high-quality PET having excellent purity, whiteness and transparency.
    Type: Grant
    Filed: July 31, 2000
    Date of Patent: April 18, 2006
    Assignee: Aies Co. Ltd.
    Inventors: Shuji Inada, Kikuchi Sato
  • Patent number: 6914154
    Abstract: A production process, especially a continuous production process, for a biphenyltetracarboxylic acid tetraester characterized by carrying out, in parallel, a step of preliminarily mixing a phthalic acid diester and a palladium compound-containing catalyst to prepare a starting mixture, a step of continuously or intermittently supplying the starting mixture to a reactor, a step of conducting oxidative dimerization reaction of the phthalic acid diester in a temperature range of from 140° C. and lower than 250° C. while supplying molecular oxygen to the reactor to form a reaction mixture in the reactor, and a step of continuously or intermittently removing a portion of the reaction mixture from the reactor.
    Type: Grant
    Filed: August 12, 2003
    Date of Patent: July 5, 2005
    Assignee: Ube Industries, Ltd.
    Inventors: Yasushi Yamamoto, Tetsuro Tsuji, Jun Haruta, Kikuo Ataka, Noboru Kakeya
  • Patent number: 6867323
    Abstract: Improved methods for generating a —C—C— bond by cross-coupling of a transferable group with an acceptor group. The transferable group is a substituent of an organosilicon nucleophile and the acceptor group is provided as an organic electrophile. The reaction is catalyzed by a Group 10 transition metal complex (e.g., Ni, Pt or Pd), particularly by a palladium complex. Certain methods of this invention use improved organosilicon nucleophiles which are readily prepared, can give high product yields and exhibit high stereoselectivity. Methods of this invention employ activating ions such as halides, hydroxide, hydride and silyloxides. In specific embodiments, organosilicon nucleophilic reagents of this invention include siloxanes, particularly cyclic siloxanes. The combination of the cross-coupling reactions of this invention with ring-closing metathesis, hydrosilylation and intramolecular hydrosilylation reactions provide useful synthetic strategies that have wide application.
    Type: Grant
    Filed: June 6, 2001
    Date of Patent: March 15, 2005
    Assignee: The Board of Trustees of the University of Illinois
    Inventors: Scott E. Denmark, Jun Young Choi, Daniel Wehrli, Zhicai Wu, Luc Neuville, Weitao Pan, Ramzi F. Sweis, Zhigang Wang, Shyh-Ming Yang
  • Patent number: 6867322
    Abstract: An ester-forming monomer obtained by depolymerization of polytrimethylene terephthalate and having an acrolein content of no greater than 0.5 wt %. Polymers obtained using the monomer and fibers, films and molded articles comprising the polymers. The ester-forming monomer is obtained by reacting polytrimethylene terephthalate with at least one compound selected from among monoalcohols, 1,3-propanediol and water in the presence of a basic substance. When the recovered ester-forming monomer is used as the starting material for production of a polymer, it is possible to produce a molding polymer for fibers, films and the like with quality equivalent to or higher than that obtained using virgin monomer.
    Type: Grant
    Filed: September 13, 2000
    Date of Patent: March 15, 2005
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Jinichiro Kato, Katsuhiro Fujimoto
  • Patent number: 6855844
    Abstract: Disclosed are polyester-ether polyols and their use in urethane prepolymers, urethane foams and non-foam urethane coatings, adhesives, sealants and/or elastomers. Methods for producing such polyester-ether polyols using double metal cyanide catalysts are disclosed, along with methods for producing urethane prepolymers. The polyester-ether polyols of the instant invention are preferably the reaction product of phthalic anhydride, diethylene glycol, and propylene oxide. These polyester-ether polyols are useful as either the primary polyol in urethane compositions or in combination with conventional auxiliary polyester- and/or polyether-based polyols. The polyester-ether polyols impart greatly improved solubility and compatibility to mixtures of either polyether and/or polyester polyols. The polyester-ether polyols of the instant invention are desirably of lower viscosity than their precursor intermediate polyester polyols and are generally soluble in either polyester- and/or polyether-based polyols.
    Type: Grant
    Filed: October 25, 2000
    Date of Patent: February 15, 2005
    Assignee: Stepan Company
    Inventors: Eric J. Geiger, Douglas K. Hillshaffer
  • Publication number: 20040127737
    Abstract: Carboxylic acid benzyl esters can be prepared by reacting dibenzyl ethers with carboxylic anhydrides in the presence of acid, optionally applied to a support, as catalyst.
    Type: Application
    Filed: September 17, 2003
    Publication date: July 1, 2004
    Inventors: Pieter Ooms, Bernd-Ulrich Schenke
  • Patent number: 6710202
    Abstract: To provide a process for producing a high-purity bis-&bgr;-hydroxyethyl terephthalate from crude terephthalic acid.
    Type: Grant
    Filed: August 5, 2002
    Date of Patent: March 23, 2004
    Assignee: Aies Co., Ltd.
    Inventors: Shuji Inada, Kikuchi Sato
  • Publication number: 20040024240
    Abstract: The present invention provides a process for the preparation of homophthlate esters useful in the preparation of homophthalic anhydride reactants.
    Type: Application
    Filed: July 28, 2003
    Publication date: February 5, 2004
    Inventors: William E. Bauta, William R. Cantrell, Dennis P. Lovett
  • Patent number: 6664380
    Abstract: Free perfluorosulfonylmethide compounds and metal salts thereof show strong catalytic activity in carbon-carbon bond formation reactions, in amounts as low as 0.1 mole %. Fluorous media may be used, especially biphasic fluorous media enabling ready recycling of the catalyst. The formula thereof is: M[C(SO2R1)3−(m+q)(SO2R2)m(SO2R3)q]x where M is H, Sc, Y, La, Ce, Pr, Nd, Sm Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, Al, Ga, In or Tl, x is the common oxidation state of a said metal M, R1, R2 and R3 are perfluorinated or polyfluoronated hydrocarbon, ether or amine moieties or mixtures thereof and m+q=0, 1, 2 or 3 (m and q being zero or integers).
    Type: Grant
    Filed: February 19, 2002
    Date of Patent: December 16, 2003
    Assignee: The Institute of Applied Catalysis
    Inventors: Anthony Gerard Martin Barrett, David Christopher Braddock, David Chadwick
  • Patent number: 6630601
    Abstract: An aromatic polyester is pre-decomposed by heating together with bis-&bgr;-hydroxyethyl terephthalate and/or a low condensate thereof and then, reacted with ethylene glycol to convert the terephthalic acid component of the pre-decomposed product into bis-&bgr;-hydroxyethyl terephthalate and/or a low condensate thereof. The thus obtained solution composition, that is, bis-&bgr;-hydroxyethyl terephthalate solution composition containing ethylene glycol, bis-&bgr;-hydroxyethyl terephthalate and cations and/or anions as impurities is brought into contact with a cation exchanger and/or an anion exchanger to remove cations and anions as impurities to produce bis-&bgr;-hydroxyethyl terephthalate having a small content of ions.
    Type: Grant
    Filed: August 17, 2000
    Date of Patent: October 7, 2003
    Assignee: Aies Company Limited
    Inventors: Shuji Inada, Kikuchi Sato
  • Patent number: 6569352
    Abstract: Disclosed are polyester-ether polyols and their use in urethane prepolymers, urethane foams and non-foam urethane coatings, adhesives, sealants and/or elastomers. Methods for producing such polyester-ether polyols are disclosed, along with methods for producing urethane prepolymers. The polyester-ether polyols of the instant invention are preferably the reaction product of phthalic anhydride, diethylene glycol, and propylene oxide. These polyester-ether polyols are useful as either the primary polyol in urethane compositions or in combination with conventional auxiliary polyester- and/or polyether-based polyols. The polyester-ether polyols impart greatly improved solubility and compatibility to mixtures of either polyether and/or polyester polyols. The polyester-ether polyols of the instant invention are desirably of lower viscosity than their precursor intermediate polyester polyols and are generally soluble in either polyester- and/or polyether-based polyols.
    Type: Grant
    Filed: October 25, 1999
    Date of Patent: May 27, 2003
    Assignee: Stepan Company
    Inventors: Douglas K. Hillshafer, George Magnus
  • Patent number: 6566548
    Abstract: Novel molecular compounds containing carboxylic acid derivatives represented by general formula (I) or (II) as the constituent compound and exhibiting excellent performances in various technical fields including selective separation of useful substances, chemical stabilization, nonvolatilization, prolongation of release and powderization, wherein X is (CH2)n or p-phenylene; n is 0, 1, 2 or 3; R1 to R8 and R13 to R20 are each hydrogen, C1-C6 alkyl, C2-C4 alkenyl, phenyl optionally substituted with C1-C6 alkyl, halogeno or C1-C6 alkoxy; and R9 to R12 and R21 to R24 are each hydrogen, C1-C6 alkyl, C2-C4 alkenyl, C11-C12 aralkyl or an alkali metal.
    Type: Grant
    Filed: March 29, 2001
    Date of Patent: May 20, 2003
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Satoru Abe, Hiroshi Suzuki
  • Patent number: 6472557
    Abstract: A process for producing high quality TPA suitable for PET feedstock material from recycled polyester. The process includes the steps of depolymerizing the polyester to form DMT; separating the DMT from secondary materials; and hydrolyzing the DMT to form TPA. In a preferred embodiment of the invention the recycled polyester is contacted with a component monomer or oligomer thereof to liquefy the polyester prior to depolymerizing the polyester.
    Type: Grant
    Filed: November 12, 1999
    Date of Patent: October 29, 2002
    Assignee: Eastman Chemical Company
    Inventors: Thomas Michael Pell, Jr., Michael Paul Ekart, David Dunlap Cornell, Damon Brian Shackelford, Donald Lee Carver
  • Patent number: 6462223
    Abstract: 6-Alkoxycarbonylmethyl-4H-1,3-dioxin-4-one derivatives are produced by reacting a 6-halomethyl-4H-1,3-dioxin-4-one derivative with carbon monoxide and an alcohol or water, and 3-oxopentanedicarboxylic acid esters are further produced by reacting the above derivatives with an alcohol or water. Such a process can produce 3-oxopentanedicarboxylic acid esters in an easy and simple and efficient manner.
    Type: Grant
    Filed: May 1, 2001
    Date of Patent: October 8, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Mitsuru Ohno, Noritsugu Yamasaki, Satoru Nose
  • Patent number: 6355702
    Abstract: Compounds containing unsaturated aliphatic moieties which are linked to each other by a tertiary oxycarbonyl containing acyclic moiety are basis for compositions which are cured to polymer networks which are thermally decomposable to provide residue which can be dissolved to allow repair of inoperative assemblies by replacement of inoperative components or recovery or recycling of operative elements which are affixed in assemblies by the cured compositions.
    Type: Grant
    Filed: February 2, 2000
    Date of Patent: March 12, 2002
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Kenji Ogino
  • Patent number: 6310236
    Abstract: There is herein disclosed a process for efficiently preparing, from an &agr;-hydroxycarboxylic amide and an alcohol in an industrially advantageous manner, an &agr;-hydroxycarboxylate which is useful as any of raw materials for solvents, food additives, perfumes, various organic medicines and the like. According to the present invention, there is provided a process for preparing an &agr;-hydroxycarboxylate which comprises the step of reacting an &agr;-hydroxycarboxylic amide and an alcohol in the presence of a catalyst in a liquid phase, while an ammonia concentration in a reaction solution is maintained at 0.1% by weight or less by discharging generated ammonia as a gas into a gaseous phase.
    Type: Grant
    Filed: March 23, 1999
    Date of Patent: October 30, 2001
    Assignee: Mitsubishi Gas Chemical Company
    Inventors: Kenichi Nakamura, Futoshi Kawataka, Kazuhiro Yamada, Wataru Ueno
  • Patent number: 6310233
    Abstract: A pressure process for preparing a hydroxyalkyl ester monomer and oligomer that can be used to prepare a polyester such as polyethylene terephthalate (PET) is disclosed. The process includes the steps of reacting, by ethoxylation, dicarboxylic acid and alkylene oxide in the presence of a compressed gas medium to form a specified mixture of monohydroxyalkyl ester and bishydroxyalkyl ester. The reaction pressure is such that the density of the gas medium is greater than or equal to half the critical density of the compressed gas medium. The mole ratio of the alkylene oxide to the dicarboxylic acid is less than about 2:1, and preferably 1.1:1.2. The DP of all reaction products is less than 5. The reactant product may be polymerized into a polyester. The process may optionally employ catalysts such as amines or amino acids. The compressed gas medium can be a solvent and an optional cosolvent. The temperature of reaction is from about 100° C. to 240° C. at a pressure of 50-5000 psi.
    Type: Grant
    Filed: November 4, 1998
    Date of Patent: October 30, 2001
    Assignee: Arteva North America S.A.R.L.
    Inventors: Charles J. Maurer, Gordon Shaw, Vicky S. Smith