Organic Peracid Utilized Patents (Class 549/525)
  • Patent number: 9976013
    Abstract: Acido-basic properties of a system containing a polymer fragment obtained by oxidative cleavage of a carbon-carbon double bond of a diene rubber polymer and a functional molecule having in a structure thereof an alkoxysilyl group and at least one functional group selected from the group consisting of an aldehyde group and a carbonyl group are changed such that the system becomes basic when acidic, and becomes acidic when basic, thereby combining the polymer fragment with the functional molecule to form a modified diene rubber polymer having an alkoxysilyl group incorporated therein. A silane monomer comprising tetraalkoxysilane and/or alkyl trialkoxysilane is added to the system containing the modified diene rubber polymer, followed by condensation polymerization, thereby forming silica.
    Type: Grant
    Filed: May 15, 2014
    Date of Patent: May 22, 2018
    Assignee: TOYO TIRE & RUBBER CO., LTD.
    Inventor: Nobutomo Kawai
  • Patent number: 9969850
    Abstract: Acido-basic properties of a system containing a polymer obtained by decomposing by oxidative cleavage of a carbon-carbon double bond, and a trifunctional molecule having an alkoxysilyl group in the structure as represented by the formula (A) are changed such that the system is changed into a basic system when the system is acidic and the system is changed into an acidic system when the system is basic to combine the decomposed polymer and the trifunctional molecule, thereby introducing the alkoxysilyl group into the main chain. Furthermore, acido-basic properties of a system containing a polymer obtained by decomposing by oxidative cleavage of a carbon-carbon double bond to decrease the molecular weight, and a functional molecule having an alkoxysilyl group as represented by the formula (a) are changed in the same manner as above to combine the decomposed polymer and the functional molecule, thereby introducing the alkoxysilyl group in a molecular terminal.
    Type: Grant
    Filed: March 7, 2014
    Date of Patent: May 15, 2018
    Assignee: TOYO TIRE & RUBBER CO., LTD.
    Inventor: Nobutomo Kawai
  • Patent number: 9725562
    Abstract: A modified diene polymer is obtained by decomposing a diene polymer having a carbon-carbon double bond in a main chain by oxidative cleavage of the carbon-carbon double bond to reduce a molecular weight, changing acido-basic properties of a system containing polymer fragments obtained such that the system is changed into a basic system when the system is acidic and the system is changed into an acidic system when the system is basic to combine the polymer fragments, thereby obtaining an intermediate polymer having an altered structure, and epoxidizing a carbon-carbon double bond moiety of a main chain of the intermediate polymer.
    Type: Grant
    Filed: December 11, 2013
    Date of Patent: August 8, 2017
    Assignee: TOYO TIRE & RUBBER CO., LTD.
    Inventor: Nobutomo Kawai
  • Publication number: 20140357836
    Abstract: Provided are: a novel triepoxy compound capable of forming, through polymerization, a cured article having excellent heat resistance; a production method thereof; a curable composition including the triepoxy compound; and a cured article obtained by curing the curable composition. The triepoxy compound according to the present invention is represented by Formula (1). The triepoxy compound represented by Formula (1) may be obtained typically by oxidizing a compound represented by Formula (2) with an oxidizing agent. In Formulae (1) and (2), R1 to R2° are the same as or different from one another and each represent hydrogen atom, methyl group, or ethyl group.
    Type: Application
    Filed: September 4, 2012
    Publication date: December 4, 2014
    Applicant: DAICEL CORPORATION
    Inventors: Kyuhei Kitao, Hideyuki Takai, Michihiro Sugahara
  • Publication number: 20140171666
    Abstract: Apparatus and processes are provided for forming epoxide compounds. In one embodiment, a process for the manufacture of an epoxide is provided including adding an oxidant, a water-soluble manganese complex and a terminal olefin to form a multiphasic reaction mixture, reacting the terminal olefin with the oxidant in the multiphasic reaction mixture having at least one organic phase in the presence of the water-soluble manganese complex, separating the reaction mixture into the at least one organic phase and an aqueous phase, and reusing at least part of the aqueous phase. The invention is also related to a device for performing the above process.
    Type: Application
    Filed: February 19, 2014
    Publication date: June 19, 2014
    Applicant: Momentive Specialty Chemicals Inc.
    Inventors: Prasad MUPPA, Ron Postma, Bart Van Den Berg, Juergen Stock, Holger Wiederhold, Hans Rausch, Jörg Schallenberg, Stefan Bernhardt
  • Publication number: 20130197245
    Abstract: An organometallic molybdenum acetylide dioxo complex of formula (?5-C5H5)MoO2(—Cs?CPh) and provides a simple, short, efficient process for the synthesis of organometallic molybdenum dioxo complex which is used as catalyst for a number of oxidation reactions.
    Type: Application
    Filed: March 14, 2013
    Publication date: August 1, 2013
    Inventors: Shubhangi Bhalchandra Umbarkar, Mohan Keraba Dongare, Ankush Biradar, Vaibhav Ravindrakumar Acham
  • Publication number: 20130165676
    Abstract: A continuous epoxidation process for the production of high purity propylene oxide by the reaction of propylene with an oxidant that is a per-acid, such as peracetic acid (PAA), in a reactive distillation (RD) column. The RD column provides excellent heat integration and temperature control, and the process has the advantage of lower investment cost for capital equipment. The process operates at mild temperatures and pressures. A ferric acetylacetonate homogeneous catalyst and/or stabilizer may be included as part of the PAA feed to the process to increase PAA conversion and selectivity to propylene oxide. A pre-reactor can be incorporated upsteam of the RD column to increase the residence time at lower temperatures to enhance productivity.
    Type: Application
    Filed: December 21, 2011
    Publication date: June 27, 2013
    Applicant: CPC Corporation, Taiwan
    Inventors: Karl T. Chuang, Christina Dirk-Faitakis, Tzong-Bin Lin, Hung-Chung Shen
  • Patent number: 8466302
    Abstract: A continuous epoxidation process for the production of high purity propylene oxide by the reaction of propylene with an oxidant that is a per-acid, such as peracetic acid (PAA), in a reactive distillation (RD) column. The RD column provides excellent heat integration and temperature control, and the process has the advantage of lower investment cost for capital equipment. The process operates at mild temperatures and pressures. A ferric acetylacetonate homogeneous catalyst and/or stabilizer may be included as part of the PAA feed to the process to increase PAA conversion and selectivity to propylene oxide. A pre-reactor can be incorporated upstream of the RD column to increase the residence time at lower temperatures to enhance productivity.
    Type: Grant
    Filed: December 21, 2011
    Date of Patent: June 18, 2013
    Assignee: CPC Corporation, Taiwan
    Inventors: Karl T. Chuang, Christina Dirk-Faitakis, Tzong-Bin Lin, Hung-Chung Shen
  • Patent number: 8399692
    Abstract: Product containing epichlorohydrin, wherein the amount of trichloropropane is of less than 0.01 g of trichloropropane per kg of product, a process for manufacturing the product and its use in various applications.
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: March 19, 2013
    Assignee: Solvay (Societe Anonyme)
    Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Noel Boulos
  • Patent number: 8378130
    Abstract: Product containing epichlorohydrin and at least one alkyl glycidyl ether in an amount of less than 0.1 g/kg of product. Use of the product containing epichlorohydrin in the manufacture of epoxy resins, of glycidyl ethers, of glycidyl esters, of glycidyl amides, of glycidyl imides, of products that will be used in food and drink applications, of cationization agents, and of flame retardants, of products which will be used as detergent ingredient and of epichlorohydrin oligomers.
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: February 19, 2013
    Assignee: SOLVAY (Societe Anonyme)
    Inventors: Noel Boulos, Philippe Krafft, Patrick Gilbeau, Dominique Balthasart
  • Publication number: 20130006000
    Abstract: A process for preparing a divinylarene dioxide including reacting (a) at least one divinylarene; and (b) at least one peracid oxidant compound, under conditions to form a divinylarene dioxide product; wherein the peracid oxidant compound is capable of providing an increased yield of a divinylarene dioxide product.
    Type: Application
    Filed: March 23, 2011
    Publication date: January 3, 2013
    Inventors: Gyongyi Gulyas, Robert J. Wright, Martha P. Hernandez, Eric P. Ripplinger
  • Patent number: 8318958
    Abstract: Disclosed is a method for epoxidizing olefins, which enables an epoxy compound containing no halogen atom with high yield. Specifically disclosed is an oxidizing agent composition for epoxidation of olefins, which is characterized by containing peroxide which exhibits basicity when dissolved in water and an acid anhydride.
    Type: Grant
    Filed: September 26, 2008
    Date of Patent: November 27, 2012
    Assignee: Adeka Corporation
    Inventors: Takaaki Kikuchi, Takehiro Zushi, Hirohisa Nitoh
  • Patent number: 8308975
    Abstract: A polyol includes the reaction product of an epoxidized oil and an organic acid. The epoxidized oil and the organic acid are reacted in the presence of a Lewis base catalyst including at least one of a phosphorous atom or a nitrogen atom. The polyol is formed by a method that includes the step of reacting the epoxidized oil with the organic acid in the presence of the Lewis base catalyst.
    Type: Grant
    Filed: October 25, 2011
    Date of Patent: November 13, 2012
    Assignee: BASF SE
    Inventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore Michael Smiecinski
  • Patent number: 8273879
    Abstract: The present invention relates to a pyrimidine compound (I) useful as a pharmaceutical intermediate, to a process for preparing said pyrimidine compound, to intermediates used in said process, and to the use of said pyrimidine compound in the preparation of pharmaceuticals.
    Type: Grant
    Filed: March 24, 2011
    Date of Patent: September 25, 2012
    Assignee: AstraZeneca AB
    Inventors: Ulf Larsson, Mattias Magnusson, Tibor Musil, Andreas Palmgren
  • Patent number: 8236976
    Abstract: The inventive subject matter relates to novel processes for making an epoxy alcohol from an aldehyde, comprising the steps of: (a) adding (i) an organozinc compound or (ii) divinylzinc compound and an diorganozinc compound to said aldehyde in the presence of a first catalyst to form an allylic alkoxide compound; and (b) epoxidizing said allylic alkoxide compound in the presence of an oxidant and a second catalyst.
    Type: Grant
    Filed: March 9, 2005
    Date of Patent: August 7, 2012
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Patrick Walsh, Alice E. Lurain, Ann R. Kelly, Aaron G. Maestri
  • Patent number: 8153746
    Abstract: Methods of making unsaturated modified vegetable oil-based polyols are described. Also described are methods of making oligomeric modified vegetable oil-based polyols. An oligomeric composition having a modified fatty acid triglyceride structure is also described. Also, methods of making a polyol including hydroformylation and hydrogenation of oils in the presence of a catalyst and support are described.
    Type: Grant
    Filed: June 2, 2010
    Date of Patent: April 10, 2012
    Assignee: Cargill, Incorporated
    Inventors: Zoran S. Petrovic, Ivan X. Javni, Alisa Zlatanic, Andrew Xiuguang Guo
  • Patent number: 8084631
    Abstract: A polyol includes the reaction product of an epoxidized oil and an organic acid. The epoxidized oil and the organic acid are reacted in the presence of a Lewis base catalyst including at least one of a phosphorous atom or a nitrogen atom. The polyol is formed by a method that includes the step of reacting the epoxidized oil with the organic acid in the presence of the Lewis base catalyst.
    Type: Grant
    Filed: May 15, 2008
    Date of Patent: December 27, 2011
    Assignee: BASF SE
    Inventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore M. Smiecinski
  • Publication number: 20110190517
    Abstract: Titanium-MWW zeolite is prepared by heating a gel formed from a titanium compound, a silicon source, a boron source, an MWW-templating agent, and water at a temperature in the range of 35° C. to 75° C. for a period of 8 to 30 hours to form a pre-crystallized gel, and heating the pre-crystallized gel to a temperature in the range of 160° C. to 190° C. for a period of 5 or more days to form the titanium-MWW zeolite. The zeolite, after it is contacted with an acid, is useful in olefin epoxidation with hydrogen peroxide.
    Type: Application
    Filed: February 1, 2010
    Publication date: August 4, 2011
    Inventors: Beaven S. Mandimutsira, Jay F. Miller
  • Patent number: 7932409
    Abstract: A process for producing oleochemical polyols comprises the steps of epoxidizing unsaturated oil using an organic acid together with oxygenated water or a per-acid to obtain epoxidized oil; washing the epoxidized oil with salt water to remove unused organic acid together with oxygenated water or a per-acid; neutralizing acidic condition of the washed epoxidized oil with a base; washing the neutralized epoxidized oil with a salt solution until the pH of the neutralized epoxidized oil reaching 6.5 to 7.5 to removed the base residue; drying the washed neutralized epoxidized oil under vacuum; and reacting the washed neutralized dried epoxidized oil with polyhydric alcohol in the presence of boron trifluoride-diethylether complex to produce the oleochemical polyols. The oleochemical polyols are then subjected to the same washing, neutralizing, washing and drying process as in preparing the washed neutralized dried epoxidized oil.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: April 26, 2011
    Assignee: Malaysian Palm Oil Board
    Inventors: Hazimah Abu Hassan, Tuan Noor Maznee Tuan Ismail, Mohd Norhisham Sattar, Seng Soi Hoong, Tian Lye Ooi, Salmiah Ahmad, Kosheela Devi a/p Poo Palam, Mei Yee Cheong
  • Patent number: 7786224
    Abstract: A liquid epoxy resin composition of an epoxy resin, a curing agent, and a curing accelerator, where the epoxy resin is an alicyclic epoxy compound present in an amount from 100 to 30% by weight. The alicyclic epoxy compound is preferably produced by using a percarboxylic acid having a water content of 2% by weight. The curing agent is preferably a liquid acid anhydride.
    Type: Grant
    Filed: July 1, 2004
    Date of Patent: August 31, 2010
    Assignee: Daicel Chemical Industries, Ltd
    Inventor: Hideyuki Takai
  • Patent number: 7786239
    Abstract: Methods of making unsaturated modified vegetable oil-based polyols are described. Also described are methods of making oligomeric modified vegetable oil-based polyols. An oligomeric composition having a modified fatty acid triglyceride structure is also described. Also, methods of making a polyol including hydroformylation and hydrogenation of oils in the presence of a catalyst and support are described.
    Type: Grant
    Filed: June 24, 2005
    Date of Patent: August 31, 2010
    Assignee: Pittsburg State University
    Inventors: Zoran S. Petrovic, Ivan Javni, Alisa Zlatanic, Andrew Guo
  • Patent number: 7732627
    Abstract: A high-purity cycloaliphatic diepoxy compound of General Formula (II) is an epoxidized product of a cycloaliphatic diolefinic compound of General Formula (I) having an isomer content as detected in gas chromatography (GC) of 15% or less: wherein X represents a bivalent group selected from the group consisting of, for example, O, S, —SO—, —SO2—, —CH2—, and —C(CH3)2—; and R1 to R18 may be the same as or different from each other and each represent hydrogen atom, a halogen atom, a hydrocarbon group which may contain oxygen atom or a halogen atom, or an alkoxy group which may be substituted. Such a high-purity cycloaliphatic diepoxy compound is prepared by producing the cycloaliphatic diolefinic compound through distillation, epoxidizing the compound with an aliphatic percarboxylic acid containing substantially no water, carrying out desolvation, and further purifying the epoxidized compound through distillation.
    Type: Grant
    Filed: December 27, 2005
    Date of Patent: June 8, 2010
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hideyuki Takai, Hiroto Tanigawa, Katsuya Maruo
  • Patent number: 7713906
    Abstract: A catalyst composition comprising titanium incorporated into a silica support, characterized in that the silica support is a shaped extrudate of silica powder. The catalyst composition is useful in the epoxidation of olefins into alkylene oxides using organic hydroperoxides. The composition can be prepared by extruding silica powder into an extrudate having a selected shape; calcining the extrudate; impregnating the extrudate with a titanium-containing impregnating agent; and drying and calcining the impregnated extrudate.
    Type: Grant
    Filed: June 21, 2001
    Date of Patent: May 11, 2010
    Assignee: Shell Oil Company
    Inventors: Paul Blankenstein, Mark Crocker, Carl Johan Gerrit Van Der Grift, Johannes Jacobus Maria Van Vlaanderen
  • Patent number: 7550064
    Abstract: The invention relates to a continuously operated process for the purification by distillation of the oxirane formed in the oxirane synthesis by reaction of a hydroperoxide with an organic compound, wherein the crude oxirane is separated in a dividing wall column into low-, intermediate- and high-boiling fractions and the oxirane is taken off as intermediate boiler at the side offtake in a concentration of at least 99.9%.
    Type: Grant
    Filed: July 23, 2003
    Date of Patent: June 23, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Bassler, Hans-Georg Goebbel, Joaquim Henrique Teles, Peter Rudolf
  • Patent number: 7544763
    Abstract: The present invention relates to a manufacturing process for producing a polyol from a fatty acid ester in-situ. The process does not use any added organic or inorganic acid catalyst. The polyol produced by the process is essentially free of any cation or anion. The fatty acid ester oil epoxidation and hydroxylation reactions can occur progressively in the same reactor for essentially a one-pot reaction. The polyol produced by the process is essentially free of any cation or anion. The polyol can be used to produce polyurethanes having improved properties.
    Type: Grant
    Filed: November 7, 2006
    Date of Patent: June 9, 2009
    Assignee: Arkema Inc.
    Inventor: Mohammad Kazemizadeh
  • Patent number: 7442843
    Abstract: A process for producing cumene by subjecting cumyl alcohol to hydrogenolysis or hydrogenation subsequent to dehydration, which comprises using a palladium-based catalyst as a catalyst for the hydrogenolysis or the hydrogenation, and using hydrogen having a carbon monoxide concentration of 0.1 to 10% by volume as hydrogen.
    Type: Grant
    Filed: September 15, 2004
    Date of Patent: October 28, 2008
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tetsuo Suzuki, Masaru Ishino, Toshio Nakayama
  • Patent number: 7381829
    Abstract: A process for producing propylene oxide, which comprises the following steps: oxidation step: a step of obtaining cumene hydroperoxide by oxidizing cumene; epoxidation step: a step of obtaining propylene oxide and cumyl alcohol by reacting cumene hydroperoxide obtained in the oxidation step with propylene; and converting step: a step of converting cumyl alcohol obtained in the epoxidation step into cumene in the presence of a solid catalyst and recycling said cumene to the oxidation step, wherein a concentration of methylbenzyl alcohol in a liquid containing cumene recycled to the oxidation step, is 1% by weight or less.
    Type: Grant
    Filed: September 15, 2004
    Date of Patent: June 3, 2008
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junpei Tsuji, Masaru Ishino
  • Patent number: 7323154
    Abstract: A titanosilicate represented by the following compositional formula (1), wherein in the infrared absorption spectrum measured in the dehydrated state, the absorption spectrum has an absorption band having a relative maximum value at 930±15 cm?1: xTiO2.(1?x)SiO2??Compositional Formula (1) (wherein x is from 0.0001 to 0.2).
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: January 29, 2008
    Assignee: Showa Denko K.K.
    Inventors: Takashi Tatsumi, Peng Wu, Katsuyuki Tsuji
  • Patent number: 7273941
    Abstract: A process of preparing an olefin oxide, preferably propylene oxide, and an alcohol, such as ?-ethylphenyl alcohol, the process involving contacting an olefin, such as propylene, and an organic hydroperoxide, such as ethylbenzene hydroperoxide, in the presence of an epoxidation catalyst, preferably, a homogeneous molybdenum catalyst, in a single reactor system or in a multi-reactor system containing a plurality of sequentially interconnected reactors. Each reactor in the single or multi-reactor system is preferably divided into a plurality of reaction zones designed to facilitate plug flow behavior. The olefin is fed to a first reaction zone in the single reactor system or to a first reactor in the multi-reactor system. The organic hydroperoxide feed is split into a plurality of split organic hydroperoxide feedstreams, and the split feedstreams are distributed throughout the reaction zones, or the reactors, or both.
    Type: Grant
    Filed: December 4, 2002
    Date of Patent: September 25, 2007
    Assignee: Dow Global Technologies Inc.
    Inventors: Gary R. Strickler, George J. Quarderer, Jr., Joerg P. Lindner
  • Patent number: 7153971
    Abstract: A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.
    Type: Grant
    Filed: August 28, 2001
    Date of Patent: December 26, 2006
    Assignee: Colorado State University Research Foundation
    Inventor: Yian Shi
  • Patent number: 7094915
    Abstract: The present invention relates to a biphasic process for the epoxidation of an organic compound by organic compound by organic hydroperoxide. More particularly, the present invention relates to a biphasic process for the epoxidation of an organic compound by organic hydroperoxide to the corresponding epoxide, using chromate or dichromate anions as the catalyst in aqueous medium.
    Type: Grant
    Filed: November 26, 2003
    Date of Patent: August 22, 2006
    Inventors: Vasant Ramchandra Choudhary, Nilesh Sudhir Patil
  • Patent number: 7067680
    Abstract: A process for preparing organic hydroperoxide having a reduced content of contaminants, which process involves: (a) oxidation of an organic compound to obtain reaction product containing an organic hydroperoxide; (b) contacting at least part of the organic hydroperoxide containing reaction product with a basic aqueous solution; (c) separating the hydrocarbonaceous phase containing organic hydroperoxide from the aqueous phase; (d) washing at least part of the separated hydrocarbonaceous phase containing organic hydroperoxide; and (e) contacting at least part of the hydrocarbonaceous phase containing organic hydroperoxide with a guard bed having solid adsorbent with a void content of from 50% to 98% by volume.
    Type: Grant
    Filed: December 17, 2001
    Date of Patent: June 27, 2006
    Assignee: Shell Oil Company
    Inventor: Carolus Matthias Anna Maria Mesters
  • Patent number: 7012120
    Abstract: This invention relates to thermosetting resin compositions useful for mounting onto a circuit board semiconductor devices, such as CSPs, BGAs, LGAs and the like, each of which having a semiconductor chip, such as LSI, on a carrier substrate. The compositions of this invention are reworkable when subjected to appropriate conditions.
    Type: Grant
    Filed: March 27, 2001
    Date of Patent: March 14, 2006
    Assignee: Henkel Corporation
    Inventors: Philp T. Klemarczyk, Andrew D. Messana, Afranio Torres-Filho, Erin K. Yaeger, Takahisa Doba
  • Patent number: 6906208
    Abstract: A material especially useful for the selective oxidation of hydrocarbons and other organic compounds includes a non-crystalline, porous inorganic oxide having at least 97 volume percent mesopores based on micropores and mesopores, and at least one catalytically active metal selected from the group consisting of one or more transition metal and one or more noble metal.
    Type: Grant
    Filed: September 18, 2002
    Date of Patent: June 14, 2005
    Assignee: ABB Lummus Global Inc.
    Inventors: Zhiping Shan, Thomas Maschmeyer, Jacobus Cornelius Jansen
  • Patent number: 6770766
    Abstract: The invention relates to a novel process that makes it possible to epoxidize &agr;,&bgr;-unsaturated enones or &agr;,&bgr;-unsaturated sulfones with high conversions and enantiomeric excesses in the presence of a water-soluble base, an oxidant, a diastereomer- and enantiomer-enriched homo-polyamino acid as catalyst, water, an organic solvent that is immiscible or has only limited miscibility with water, and a specific phase-transfer catalyst as cocatalyst.
    Type: Grant
    Filed: July 24, 2002
    Date of Patent: August 3, 2004
    Assignee: Bayer Chemicals AG
    Inventors: Thomas Geller, Christa Maria Krüger, Hans-Christian Militzer
  • Patent number: 6740763
    Abstract: A method of epoxidizing an unsaturated compound having a carbon-to-carbon double bond to form an oxirane ring across the double bond comprising adding to said unsaturated compound (a) an organic acid capable of being oxidized to form a peracid; (b) an oxidizing agent selected from hydrogen peroxide or acetaldehyde monoperacetate, or a combination thereof; and (c) with or without an acid catalyst selected from a mineral acid or styrene sulfonic acid, or a combination thereof to form a reactant mixture; and forming the reactant mixture in a film against a wall of a thin-film reactor that is at a temperature sufficient to form a peracid from the organic acid, and contacting the film of reactant mixture against the film reactor wall for a time sufficient for reaction of a portion of the peracid with the unsaturated compound to form an oxirane ring across a double bond of the unsaturated compound. In another embodiment, preformed peracid and unsaturated compound are added directly to the thin-film reactor.
    Type: Grant
    Filed: June 27, 2003
    Date of Patent: May 25, 2004
    Assignee: The C.P. Hall Company
    Inventors: James A. Nowak, Thomas A. Zillner, Leslie Patrick Mullin, III
  • Patent number: 6686483
    Abstract: The present invention provides a variety of methods that are based on stereoselective epoxidation of an olefin by an epoxidizing agent derived from a reaction between an oxidizing agent and a chiral ketone. For example, present invention provides methods for producing an epoxide from an olefin, for increasing a relative concentration of at least one stereoisomer of an olefin, and for stereoselectively producing an &agr;-acyloxy carbonyl compound. Preferably, the chiral ketone is of the formula: or a derivative thereof which is capable of converting to the chiral ketone of Formula I under the reaction conditions, where a, b, n, X, R1, R2, R3, R4, R5 and R6 are those defined herein.
    Type: Grant
    Filed: January 7, 2002
    Date of Patent: February 3, 2004
    Assignee: Colorado State University Research Foundation
    Inventor: Yian Shi
  • Patent number: 6504040
    Abstract: The invention relates to an integrated process for the preparation of epoxidised olefins. In the first stage, dilute hydrogen peroxide solutions are prepared from the elements hydrogen and oxygen and are reacted in a subsequent liquid-phase epoxidation with olefin in the presence of titanium silicalite to form epoxidised olefins, and the solvents are returned to the H2O2 process again.
    Type: Grant
    Filed: June 7, 2001
    Date of Patent: January 7, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Vogtel, Ernst-Ulrich Dorf, Gerhard Wegener, Markus Weisbeck
  • Patent number: 6482964
    Abstract: Process for the selective preparation of &bgr;-isophorone epoxide by epoxidation of &bgr;-isophorone with organic percarboxylic acids at a water content of less than 5 wt. %.
    Type: Grant
    Filed: May 16, 2001
    Date of Patent: November 19, 2002
    Assignee: Degussa AG
    Inventors: Steffen Krill, Klaus Huthmacher, Alexander Möller
  • Patent number: 6437045
    Abstract: Powder coating compositions comprise a binder selected from carboxyl-group-containing polyesters, carboxyl-group-containing poly(meth)acrylates and mixtures of the said substances, and one or more epoxy compounds, wherein the epoxy compounds comprise at least one compound of formula (I) that is solid at 25° C.
    Type: Grant
    Filed: October 25, 2000
    Date of Patent: August 20, 2002
    Assignee: Vantico Inc.
    Inventors: Christoph Rickert, François Turpin, Jacques Francois, Mireille Tena
  • Publication number: 20020099230
    Abstract: The present invention is related to an improved process for obtaining oleochemical polyols from oils, principally of a vegetable origin. The polyols obtained consist of a mixture of ethers, esters, primary and secondary alcohols and have the characteristic of being self-compatible with the new blowing agents: hydrochlorofluorocarbons, HCFC's, hydrofluorocarbons, HFC's and hydrocarbons, HC's of a low molecular weight and low boiling point. The process of this invention is characterized because it uses Lewis type acids in such a way that they do not form precipitates and therefore it is not necessary to remove precipitates from the polyol. The process of the present invention makes it possible to obtain polyols with high functionality and controlled reactivity. These characteristics render the product suitable for use as a raw material in the production process of rigid foams, such as polyurethane for spraying, refrigeration and imitation wood, coatings, among others.
    Type: Application
    Filed: November 21, 2001
    Publication date: July 25, 2002
    Inventors: Nicolas Ramirez-de-Arellano-Aburto, Andres Cohen-Barki, M. Javier Cruz-Gomez
  • Patent number: 6409769
    Abstract: A method for kinetically resolving a stereoisomer mixture of compounds using asymmetric epoxidation is provided. Compounds contain an olefin moiety providing one stereoisomer to be epoxidized at a higher rate than the other stereoisomer using a chiral ketone and an oxidizing agent.
    Type: Grant
    Filed: December 4, 2000
    Date of Patent: June 25, 2002
    Assignee: Colorado State University Research Foundation
    Inventor: Yian Shi
  • Publication number: 20020038041
    Abstract: A method of preparing novel alkyl glycidyl carbonate compositions comprising reacting a metal alkoxide with a cyclic organic carbonate in the presence of a solvent under conditions suitable for producing an alkyl glycidyl carbonate. Novel alkyl glycidyl carbonate compositions are also disclosed.
    Type: Application
    Filed: September 5, 2001
    Publication date: March 28, 2002
    Applicant: Huntsman Petrochemical Corporation
    Inventors: John H. Clements, Howard P. Klein, Edward T. Marquis
  • Patent number: 6348608
    Abstract: A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.
    Type: Grant
    Filed: April 6, 1999
    Date of Patent: February 19, 2002
    Inventor: Yian Shi
  • Patent number: 6288248
    Abstract: Epichlorohydrin-based product containing at least 99.9% by weight of epichlorohydrin and a total amount of chloro impurities of less than or equal to 150 ppm by weight, and process for manufacturing this product by reaction of allyl chloride with a peroxide compound in the presence of water, a catalyst and a diluent in at least one reactor, and separation of the epichlorohydrin formed.
    Type: Grant
    Filed: November 25, 1998
    Date of Patent: September 11, 2001
    Assignee: Solvay (Société Anonyme)
    Inventors: Michel Strebelle, Patrick Gilbeau, Jean-Pierre Catinat
  • Patent number: 6271400
    Abstract: An process for epoxidizing diversely functionalized olefins by oxorhenium catalysis employs conditions which control water concentration. By controlling water concentration, one can maximize monoperoxo complex formation and increase turnover which subsequently reduces diol side products obtained from epoxide ring opening and increases the yield of the desired epoxide product. The optimal range of water concentrations is 0.50-80.0 mol %. Using less than 0.5 mol % water does not result in practical turnovers and 1.0 equivalent of water (or more) is detrimental to the lifetime of the active catalytic species formed.
    Type: Grant
    Filed: October 23, 1998
    Date of Patent: August 7, 2001
    Assignee: The Scripps Research Institute
    Inventors: K. Barry Sharpless, Andrei K. Yudin
  • Patent number: 6255500
    Abstract: Process for the preparation of aliphatic diene ester diepoxides comprising the steps of a) reacting an aliphalic diene ester with a peracid at a temperature at or below 15° C. in the absence of a pH control agent to epoxidize the double bonds of the diene ester; and b) isolating the epoxidized diene ester form the resulting reaction mixture.
    Type: Grant
    Filed: January 21, 2000
    Date of Patent: July 3, 2001
    Assignee: Loctite Corporation
    Inventor: Philip T. Klemarczyk
  • Patent number: 6228955
    Abstract: A process for preparing an optically-enriched chiral epoxide of formula I wherein R1, R2 and R3 are each independently selected from H, R, R—CO— and R—O—CO—, each R independently being substantially a hydrocarbon group of up to 20 carbon atoms, and X is an alkyl or cycloalkyl group of up to 10 carbon atoms, provided that —CO—X is not enolisable, which comprises the asymmetric epoxidation of a corresponding prochiral alkene of formula II R1R2C═CR3—CO—X  (II) by reaction with an oxidant in the presence of a chiral catalyst. Many optically-enriched epoxides (I) are novel.
    Type: Grant
    Filed: October 20, 1997
    Date of Patent: May 8, 2001
    Assignee: Chirotech Technology, Ltd.
    Inventors: Stanley Michael Roberts, Brian Michael Adger
  • Patent number: 6225482
    Abstract: A process for the enantioselective epoxidation of C═C double bonds and use of the epoxides. The present invention provides a process for the enantioselective epoxidation of compounds of the formula I by means of a diastereomer and enantiomer enriched homopolyamino acid and an oxidizing agent. The epoxides prepared according to the invention are used as intermediates in organic syntheses.
    Type: Grant
    Filed: November 30, 1999
    Date of Patent: May 1, 2001
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Karlheinz Drauz, Stan M. Roberts, John Skidmore
  • Patent number: 6107433
    Abstract: A vegetable oil-based polyol is made by adding a peroxyacid to vegetable oil wherein said peroxyacid reacts with said vegetable oil to form epoxidized vegetable oil and adding said epoxidized vegetable oil to a mixture of an alcohol, water, and a catalytic amount of fluoboric acid so as to form a vegetable oil-based polyol. A further embodiment of the present invention involves making a vegetable oil-based polyol using an epoxidized vegetable oil as the starting material. The epoxidized vegetable oil undergoes hydroxylation by the same process as outlined above. According to another aspect of the present invention, the vegetable oil-based polyol formed by the novel methods of this invention may be reacted with an isocyanate to form a polyurethane. Alternatively, a filler such as silica may be combined with the vegetable oil-based polyol before it is reacted with the isocyanate. These polyurethanes made from vegetable oil-based polyols may be used to form electroinsulating casting resins.
    Type: Grant
    Filed: November 6, 1998
    Date of Patent: August 22, 2000
    Assignee: Pittsburg State University
    Inventors: Zoran Petrovic, Andrew Guo, Ivan Javni