Organic Peracid Utilized Patents (Class 549/525)
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Patent number: 10809220Abstract: The synthesis of silver nanoparticles (AgNPs)/meso-porous silicon (PSi) nanocomposite and its effective use as efficient chemical sensor and photocatalyst are described. The PSi was prepared via a simple stain etching of Si microparticles in HF/HNO3 aqueous solution, followed by the deposition of AgNPs onto stain etched PSi by the immersion plating technique. The resultant nanocomposite is used successfully for (i) enhanced electro-oxidation and quantification of ascorbic acid (AA) on modified glassy carbon electrode and (ii) for the photo-reduction of hexavalent chromium Cr(VI) to trivalent Cr(III) under direct visible light irradiation in the presence of citric acid.Type: GrantFiled: July 10, 2019Date of Patent: October 20, 2020Assignee: Najran UniversityInventors: Farid A Harraz, Mohd Faisal, Mohammad S Al-Assiri, Ahmed Mohamed El-Toni
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Patent number: 9976013Abstract: 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: GrantFiled: May 15, 2014Date of Patent: May 22, 2018Assignee: TOYO TIRE & RUBBER CO., LTD.Inventor: Nobutomo Kawai
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Patent number: 9969850Abstract: 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: GrantFiled: March 7, 2014Date of Patent: May 15, 2018Assignee: TOYO TIRE & RUBBER CO., LTD.Inventor: Nobutomo Kawai
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Patent number: 9725562Abstract: 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: GrantFiled: December 11, 2013Date of Patent: August 8, 2017Assignee: TOYO TIRE & RUBBER CO., LTD.Inventor: Nobutomo Kawai
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Publication number: 20140357836Abstract: 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: ApplicationFiled: September 4, 2012Publication date: December 4, 2014Applicant: DAICEL CORPORATIONInventors: Kyuhei Kitao, Hideyuki Takai, Michihiro Sugahara
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Publication number: 20140171666Abstract: 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: ApplicationFiled: February 19, 2014Publication date: June 19, 2014Applicant: Momentive Specialty Chemicals Inc.Inventors: Prasad MUPPA, Ron Postma, Bart Van Den Berg, Juergen Stock, Holger Wiederhold, Hans Rausch, Jörg Schallenberg, Stefan Bernhardt
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Publication number: 20130197245Abstract: 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: ApplicationFiled: March 14, 2013Publication date: August 1, 2013Inventors: Shubhangi Bhalchandra Umbarkar, Mohan Keraba Dongare, Ankush Biradar, Vaibhav Ravindrakumar Acham
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Publication number: 20130165676Abstract: 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: ApplicationFiled: December 21, 2011Publication date: June 27, 2013Applicant: CPC Corporation, TaiwanInventors: Karl T. Chuang, Christina Dirk-Faitakis, Tzong-Bin Lin, Hung-Chung Shen
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Patent number: 8466302Abstract: 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: GrantFiled: December 21, 2011Date of Patent: June 18, 2013Assignee: CPC Corporation, TaiwanInventors: Karl T. Chuang, Christina Dirk-Faitakis, Tzong-Bin Lin, Hung-Chung Shen
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Patent number: 8399692Abstract: 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: GrantFiled: June 11, 2008Date of Patent: March 19, 2013Assignee: Solvay (Societe Anonyme)Inventors: Philippe Krafft, Patrick Gilbeau, Dominique Balthasart, Noel Boulos
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Patent number: 8378130Abstract: 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: GrantFiled: June 11, 2008Date of Patent: February 19, 2013Assignee: SOLVAY (Societe Anonyme)Inventors: Noel Boulos, Philippe Krafft, Patrick Gilbeau, Dominique Balthasart
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Publication number: 20130006000Abstract: 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: ApplicationFiled: March 23, 2011Publication date: January 3, 2013Inventors: Gyongyi Gulyas, Robert J. Wright, Martha P. Hernandez, Eric P. Ripplinger
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Patent number: 8318958Abstract: 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: GrantFiled: September 26, 2008Date of Patent: November 27, 2012Assignee: Adeka CorporationInventors: Takaaki Kikuchi, Takehiro Zushi, Hirohisa Nitoh
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Patent number: 8308975Abstract: 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: GrantFiled: October 25, 2011Date of Patent: November 13, 2012Assignee: BASF SEInventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore Michael Smiecinski
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Patent number: 8273879Abstract: 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: GrantFiled: March 24, 2011Date of Patent: September 25, 2012Assignee: AstraZeneca ABInventors: Ulf Larsson, Mattias Magnusson, Tibor Musil, Andreas Palmgren
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Patent number: 8236976Abstract: 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: GrantFiled: March 9, 2005Date of Patent: August 7, 2012Assignee: The Trustees of the University of PennsylvaniaInventors: Patrick Walsh, Alice E. Lurain, Ann R. Kelly, Aaron G. Maestri
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Patent number: 8153746Abstract: 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: GrantFiled: June 2, 2010Date of Patent: April 10, 2012Assignee: Cargill, IncorporatedInventors: Zoran S. Petrovic, Ivan X. Javni, Alisa Zlatanic, Andrew Xiuguang Guo
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Patent number: 8084631Abstract: 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: GrantFiled: May 15, 2008Date of Patent: December 27, 2011Assignee: BASF SEInventors: Yeonsuk Roh, Rajesh Kumar, Cheng-Le Zhao, David Kaczan, Theodore M. Smiecinski
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Publication number: 20110190517Abstract: 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: ApplicationFiled: February 1, 2010Publication date: August 4, 2011Inventors: Beaven S. Mandimutsira, Jay F. Miller
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Patent number: 7932409Abstract: 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: GrantFiled: March 28, 2008Date of Patent: April 26, 2011Assignee: Malaysian Palm Oil BoardInventors: 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
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Patent number: 7786224Abstract: 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: GrantFiled: July 1, 2004Date of Patent: August 31, 2010Assignee: Daicel Chemical Industries, LtdInventor: Hideyuki Takai
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Patent number: 7786239Abstract: 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: GrantFiled: June 24, 2005Date of Patent: August 31, 2010Assignee: Pittsburg State UniversityInventors: Zoran S. Petrovic, Ivan Javni, Alisa Zlatanic, Andrew Guo
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Patent number: 7732627Abstract: 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: GrantFiled: December 27, 2005Date of Patent: June 8, 2010Assignee: Daicel Chemical Industries, Ltd.Inventors: Hideyuki Takai, Hiroto Tanigawa, Katsuya Maruo
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Patent number: 7713906Abstract: 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: GrantFiled: June 21, 2001Date of Patent: May 11, 2010Assignee: Shell Oil CompanyInventors: Paul Blankenstein, Mark Crocker, Carl Johan Gerrit Van Der Grift, Johannes Jacobus Maria Van Vlaanderen
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Patent number: 7550064Abstract: 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: GrantFiled: July 23, 2003Date of Patent: June 23, 2009Assignee: BASF AktiengesellschaftInventors: Peter Bassler, Hans-Georg Goebbel, Joaquim Henrique Teles, Peter Rudolf
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Patent number: 7544763Abstract: 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: GrantFiled: November 7, 2006Date of Patent: June 9, 2009Assignee: Arkema Inc.Inventor: Mohammad Kazemizadeh
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Patent number: 7442843Abstract: 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: GrantFiled: September 15, 2004Date of Patent: October 28, 2008Assignee: Sumitomo Chemical Company, LimitedInventors: Tetsuo Suzuki, Masaru Ishino, Toshio Nakayama
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Patent number: 7381829Abstract: 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: GrantFiled: September 15, 2004Date of Patent: June 3, 2008Assignee: Sumitomo Chemical Company, LimitedInventors: Junpei Tsuji, Masaru Ishino
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Patent number: 7323154Abstract: 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: GrantFiled: February 26, 2003Date of Patent: January 29, 2008Assignee: Showa Denko K.K.Inventors: Takashi Tatsumi, Peng Wu, Katsuyuki Tsuji
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Patent number: 7273941Abstract: 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: GrantFiled: December 4, 2002Date of Patent: September 25, 2007Assignee: Dow Global Technologies Inc.Inventors: Gary R. Strickler, George J. Quarderer, Jr., Joerg P. Lindner
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Patent number: 7153971Abstract: A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.Type: GrantFiled: August 28, 2001Date of Patent: December 26, 2006Assignee: Colorado State University Research FoundationInventor: Yian Shi
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Patent number: 7094915Abstract: 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: GrantFiled: November 26, 2003Date of Patent: August 22, 2006Inventors: Vasant Ramchandra Choudhary, Nilesh Sudhir Patil
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Patent number: 7067680Abstract: 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: GrantFiled: December 17, 2001Date of Patent: June 27, 2006Assignee: Shell Oil CompanyInventor: Carolus Matthias Anna Maria Mesters
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Patent number: 7012120Abstract: 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: GrantFiled: March 27, 2001Date of Patent: March 14, 2006Assignee: Henkel CorporationInventors: Philp T. Klemarczyk, Andrew D. Messana, Afranio Torres-Filho, Erin K. Yaeger, Takahisa Doba
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Patent number: 6906208Abstract: 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: GrantFiled: September 18, 2002Date of Patent: June 14, 2005Assignee: ABB Lummus Global Inc.Inventors: Zhiping Shan, Thomas Maschmeyer, Jacobus Cornelius Jansen
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Patent number: 6770766Abstract: 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: GrantFiled: July 24, 2002Date of Patent: August 3, 2004Assignee: Bayer Chemicals AGInventors: Thomas Geller, Christa Maria Krüger, Hans-Christian Militzer
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Patent number: 6740763Abstract: 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: GrantFiled: June 27, 2003Date of Patent: May 25, 2004Assignee: The C.P. Hall CompanyInventors: James A. Nowak, Thomas A. Zillner, Leslie Patrick Mullin, III
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Patent number: 6686483Abstract: 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: GrantFiled: January 7, 2002Date of Patent: February 3, 2004Assignee: Colorado State University Research FoundationInventor: Yian Shi
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Patent number: 6504040Abstract: 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: GrantFiled: June 7, 2001Date of Patent: January 7, 2003Assignee: Bayer AktiengesellschaftInventors: Peter Vogtel, Ernst-Ulrich Dorf, Gerhard Wegener, Markus Weisbeck
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Patent number: 6482964Abstract: 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: GrantFiled: May 16, 2001Date of Patent: November 19, 2002Assignee: Degussa AGInventors: Steffen Krill, Klaus Huthmacher, Alexander Möller
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Patent number: 6437045Abstract: 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: GrantFiled: October 25, 2000Date of Patent: August 20, 2002Assignee: Vantico Inc.Inventors: Christoph Rickert, François Turpin, Jacques Francois, Mireille Tena
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Publication number: 20020099230Abstract: 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: ApplicationFiled: November 21, 2001Publication date: July 25, 2002Inventors: Nicolas Ramirez-de-Arellano-Aburto, Andres Cohen-Barki, M. Javier Cruz-Gomez
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Patent number: 6409769Abstract: 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: GrantFiled: December 4, 2000Date of Patent: June 25, 2002Assignee: Colorado State University Research FoundationInventor: Yian Shi
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Publication number: 20020038041Abstract: 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: ApplicationFiled: September 5, 2001Publication date: March 28, 2002Applicant: Huntsman Petrochemical CorporationInventors: John H. Clements, Howard P. Klein, Edward T. Marquis
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Patent number: 6348608Abstract: A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.Type: GrantFiled: April 6, 1999Date of Patent: February 19, 2002Inventor: Yian Shi
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Patent number: 6288248Abstract: 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: GrantFiled: November 25, 1998Date of Patent: September 11, 2001Assignee: Solvay (Société Anonyme)Inventors: Michel Strebelle, Patrick Gilbeau, Jean-Pierre Catinat
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Patent number: 6271400Abstract: 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: GrantFiled: October 23, 1998Date of Patent: August 7, 2001Assignee: The Scripps Research InstituteInventors: K. Barry Sharpless, Andrei K. Yudin
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Patent number: 6255500Abstract: 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: GrantFiled: January 21, 2000Date of Patent: July 3, 2001Assignee: Loctite CorporationInventor: Philip T. Klemarczyk
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Patent number: 6228955Abstract: 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: GrantFiled: October 20, 1997Date of Patent: May 8, 2001Assignee: Chirotech Technology, Ltd.Inventors: Stanley Michael Roberts, Brian Michael Adger
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Patent number: 6225482Abstract: 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: GrantFiled: November 30, 1999Date of Patent: May 1, 2001Assignee: Degussa-Huls AktiengesellschaftInventors: Karlheinz Drauz, Stan M. Roberts, John Skidmore