Liquid Phase Epoxidation Patents (Class 549/524)
  • Patent number: 10428201
    Abstract: The present disclosure is directed to a plasticizer composition, polymeric compositions containing the plasticizer composition, and coated conductors comprising the polymeric composition. The plasticizer composition comprises an epoxidized fatty acid alkyl ester having an APHA color value of less than 100, a triepoxide content of at least 6.5 weight percent, and an oxirane oxygen content of at least 5 grams oxirane per 100 grams of epoxidized fatty acid alkyl ester.
    Type: Grant
    Filed: October 14, 2015
    Date of Patent: October 1, 2019
    Assignee: Dow Global Technologies LLC
    Inventors: Abhijit Ghosh-Dastidar, Manish Mundra
  • Patent number: 9145378
    Abstract: Processes are provided for the formation of an epoxyethyl ether or a glycidyl ether. In one embodiment, a process is provided for the manufacture of an epoxyethyl ether or glycidyl ether including reacting a vinyl ether or an allyl ether with an oxidant in the presence of a water-soluble manganese complex in an aqueous reaction medium, wherein the water-soluble manganese complex comprises an oxidation catalyst, characterized in that the water-soluble manganese complex is a mononuclear complex of the general formula (I): [LMnX3]Y (I), or a binuclear complex of the general formula (II): [LMn(?-X)3MnL](Y)n (II), wherein Mn is a manganese; L or each L independently is a polydentate ligand, each X independently is a coordinating species and each ?-X independently is a bridging coordinating species, Y is a non-coordinating counter ion, and wherein the epoxidation is carried out at a pH in the range of from 1.0 to 6.0. The invention also relates to epoxyethyl ethers.
    Type: Grant
    Filed: January 26, 2011
    Date of Patent: September 29, 2015
    Assignee: HEXION INC.
    Inventors: Prasad Muppa, Ron Postma, Caspar Schoolderman, Sandra Rens, Kostas Stoitsas
  • Patent number: 9024048
    Abstract: Apparatus and methods are provided for forming and processing multiphasic systems. In one embodiment, the invention provides a process for the manufacture of an epoxide, including reacting an olefinically unsaturated compound with an oxidant in the presence of a buffer component and a water-soluble manganese complex disposed in an aqueous phase having a first pH level in a first multiphasic system, adjusting the pH of the aqueous phase to a second pH level less than the first pH level, isolating at least a portion of the aqueous phase from the first multiphasic system, adjusting the pH of the at least a portion of the aqueous phase to a third pH level greater than the second pH level, and introducing the at least a portion of the aqueous phase into a second multiphasic system.
    Type: Grant
    Filed: June 13, 2012
    Date of Patent: May 5, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Mark Kapellen, Bart Van Den Berg, Prasad Muppa, Paul Haesakkers
  • Patent number: 8962872
    Abstract: A method for preparing an epoxide is disclosed. The method for preparing an epoxide includes the step of performing a reaction of an alkene and oxidant in the presence of a Ti—Si molecular sieve as a catalyst, and increases the conversion rate of hydrogen peroxide and the yield of the epoxide.
    Type: Grant
    Filed: September 13, 2012
    Date of Patent: February 24, 2015
    Assignee: China Petrochemical Development Corporation
    Inventors: Yu-Chuan Hsu, Cheng-Fa Hsieh, I-Hui Lin
  • Publication number: 20140309442
    Abstract: A method for the oxidation of ethylene to form ethylene oxide is provided that includes passing an aqueous stream through a guard bed and one or more ion exchange treatment beds. The guard bed and the aqueous stream contain from about 0.2 to 20 wt % ethylene glycol. The guard bed contains a cross-linked polystyrene resin, partially functionalized with quaternary ammonium functional groups and the resin has a surface area of greater than 400 m2/g.
    Type: Application
    Filed: April 15, 2014
    Publication date: October 16, 2014
    Applicant: Scientific Design Company, Inc.
    Inventor: Mansoor Husain
  • Publication number: 20140187806
    Abstract: The present invention relates to a process for producing an olefinic product, comprising (a) preparing a reaction product by converting an oxygenate-comprising feedstock in an oxygenate to olefin process, the reaction product comprising at least C2+ olefins and DME, (b) separating at least part of the reaction product by means of extractive distillation using a butanol solvent into: (i) a first fraction comprising C3? olefins and butanol; and (ii) a second fraction comprising C4+ olefins, DME and butanol; (c) separating the first fraction into: (iii)a C3? olefinic product; and (iv) a third fraction comprising butanol; (d) separating the second fraction into: (v) a DME-comprising C4-C5 olefinic product; and (vi) a fourth fraction comprising butanol and C6+ olefins, wherein at least part of the third and/or fourth fraction are recycled to step (b) together with or as part of the butanol solvent.
    Type: Application
    Filed: December 20, 2013
    Publication date: July 3, 2014
    Applicant: Shell Oil Company
    Inventor: Jeroen VAN WESTRENEN
  • Patent number: 8759552
    Abstract: The present invention provides a continuous process for the epoxidation of an olefinic compound with an oxidant, which process comprises reaction of an olefinic compound with an oxidant in the presence of a catalyst in an apparatus that comprises a reactive distillation column, which column comprises (i) a reactive section, which comprises the catalyst (ii) a rectifying section situated above the reactive section and adapted to allow separation of reagents and/or by-products from products (ix) a stripping section situated below the reactive section and adapted to allow separation of product from reagents and/or by-products (x) a vessel situated below the stripping section and adapted to provide a source of heat for the column and in which initial vaporization of one or more of the reagents can occur, wherein the temperature in the reactive section (i) is a temperature at which the reaction between the olefinic compound and the oxidant takes place and the temperature in the stripping section (iii) is higher
    Type: Grant
    Filed: July 30, 2010
    Date of Patent: June 24, 2014
    Assignee: South Bank University Enterprises Ltd.
    Inventors: Basudeb Saha, Krzysztof Ambroziak, David C. Sherrington, Rene Mbeleck
  • Publication number: 20140171665
    Abstract: The present invention provides a process for removing oxygenate from an olefin stream comprising oxygenate, comprising providing to an oxygenate recovery zone the olefin stream comprising oxygenate and a solvent comprising ethanol, treating the olefin stream comprising oxygenate with the solvent, and retrieving from the oxygenate recovery zone at least one oxygenate-depleted olefinic product stream comprising olefin and a spent solvent comprising at least part of the oxygenate.
    Type: Application
    Filed: December 20, 2013
    Publication date: June 19, 2014
    Applicant: Shell Oil Company
    Inventor: Jeroen VAN WESTRENEN
  • 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
  • Patent number: 8669384
    Abstract: A process for preparing a divinylarene dioxide including (a) reacting at least one divinylarene with hypochlorous acid to form a chlorohydrin; and (b) treating the chlorohydrin formed in step (a) with at least one base, under conditions to form a divinylarene dioxide product.
    Type: Grant
    Filed: March 4, 2011
    Date of Patent: March 11, 2014
    Assignee: Dow Global Technologies Inc.
    Inventors: Eric B. Ripplinger, David Jean, David Burow, Khiet Pham, Maurice Marks, Gyongyi Gulyas
  • Publication number: 20140046079
    Abstract: A method for preparing an epoxide is disclosed. The method for preparing an epoxide includes the step of performing a reaction of an alkene and oxidant in the presence of a Ti—Si molecular sieve as a catalyst, and increases the conversion rate of hydrogen peroxide and the yield of the epoxide.
    Type: Application
    Filed: September 13, 2012
    Publication date: February 13, 2014
    Applicant: China Petrochemical Development Corporation Taipei (Taiwan)
    Inventors: Yu-Chuan Hsu, Cheng-Fa Hsieh, I-Hui Lin
  • Patent number: 8609873
    Abstract: The invention relates to a process for making HOF.RCN and using it to oxidise organic substrates in a quick and safe way. The process comprises passing diluted fluorine through a conduit and RCN in water through another conduit into a microreactor to form HOF.RCN and reacting this with an organic substrates.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: December 17, 2013
    Assignee: The Secretary of State for Defense in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Christopher Murray, Graham Sandford
  • Publication number: 20130150289
    Abstract: The invention relates to crystalline peptide keto epoxide compounds, methods of their preparation, and related pharmaceutical compositions. This invention also relates to methods for the preparation of amino acid keto-epoxides. Specifically, allylic ketones are stereoselectively converted to the desired keto epoxides.
    Type: Application
    Filed: February 1, 2013
    Publication date: June 13, 2013
    Applicant: Onyx Therapeutics, Inc.
    Inventor: Onyx Therapeutics, Inc.
  • 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: 20130023680
    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: January 26, 2011
    Publication date: January 24, 2013
    Inventors: Prasad Muppa, Ron Postma, Bart Van Den Berg, Juergen Stock, Holger Wiederhold, Hans Rausch, Jorg Schallenberg, Stefan Bernhardt
  • Publication number: 20130006001
    Abstract: The invention relates to a process for the manufacture of an epoxyethyl carboxylate or glycidyl carboxylate, including reacting a vinyl carboxylate or an allyl carboxylate using an oxidant and a water-soluble manganese complex in an aqueous reaction medium, and the water-soluble manganese complex comprises an oxidation catalyst, characterized in that the water-soluble manganese complex is a mononuclear species of the general formula (I) [LMnX3]Y (I), or a binuclear species of the general formula (II): [LMn(??X)3MnL]Yn (II), wherein Mn is a manganese; L is a ligand and each L is independently a polydentate ligand, each X is independently a coordinating species and each ??X is independently a bridging coordinating species, Y is a non-coordinating counter ion, and wherein the epoxidation is carried out at a pH in the range of from 1.0 to 7.
    Type: Application
    Filed: January 26, 2011
    Publication date: January 3, 2013
    Inventors: Prasad Muppa, Ron Postma, Caspar Schoolderman, Sandra Rens, Kostas Stoitsas
  • Publication number: 20120330042
    Abstract: Processes and compositions are provided for epoxidizing an olefinically unsaturated compound. In one embodiment, a process is provided for reacting an olefinically unsaturated compound with an oxidant in the presence of a catalyst at acidic conditions, wherein the catalyst is activated prior to the reaction at a pH that is higher than the pH during the reaction.
    Type: Application
    Filed: January 26, 2011
    Publication date: December 27, 2012
    Inventors: Prasad Muppa, Mark Kapellen, Caspar Schoolderman
  • 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
  • Publication number: 20120203015
    Abstract: An integrated process for preparing alkylene oxides and alkylene glycols is described. For this purpose, an alkylene oxide plant and an alkylene glycol plant are combined with one another and the water originating from the alkylene oxide plant and also other constituents of the reaction mixture are introduced into the alkylene glycol plant. In this way, alkylene glycols which have been produced in the alkylene oxide plant can be recovered as materials of value and the water circulation into the alkylene glycol plant can be eliminated or drastically reduced. In addition, the energy-intensive treatment of the process water from the alkylene oxide plant can be dispensed with. The integration of the two processes leads overall to better energy efficiency and conservation of resources in the work-up of residues from the process.
    Type: Application
    Filed: August 12, 2010
    Publication date: August 9, 2012
    Inventor: Ferdinand Rudolf Reif
  • 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
  • Publication number: 20120136165
    Abstract: The present invention provides a continuous process for the epoxidation of an olefinic compound with an oxidant, which process comprises reaction of an olefinic compound with an oxidant in the presence of a catalyst in an apparatus that comprises a reactive distillation column, which column comprises (i) a reactive section, which comprises the catalyst (ii) a rectifying section situated above the reactive section and adapted to allow separation of reagents and/or by-products from products (ix) a stripping section situated below the reactive section and adapted to allow separation of product from reagents and/or by-products (x) a vessel situated below the stripping section and adapted to provide a source of heat for the column and in which initial vaporisation of one or more of the reagents can occur, wherein the temperature in the reactive section (i) is a temperature at which the reaction between the olefinic compound and the oxidant takes place and the temperature in the stripping section (iii) is higher
    Type: Application
    Filed: July 30, 2010
    Publication date: May 31, 2012
    Applicant: SOUTH BANK UNIVERSITY ENTERPRISES LTD.
    Inventors: Basudeb Saha, Krzysztof Ambroziak, David C. Sherrington, Rene Mbeleck
  • Patent number: 8173823
    Abstract: Process for preparing an epoxide, wherein halogenated ketones are formed as by-products and there is at least one treatment intended to remove at least part of the halogenated ketones formed.
    Type: Grant
    Filed: May 19, 2006
    Date of Patent: May 8, 2012
    Assignee: Solvay (Société Anonyme)
    Inventor: Patrick Gilbeau
  • Patent number: 8017794
    Abstract: A process for the preparation of alkylene oxide, which process involves mixing fresh feed containing organic hydroperoxide and alkene with a recycle stream to obtain a reaction mixture containing of from 5 to 80% wt of alcohol, based on total amount of reaction mixture, contacting the reaction mixture with a heterogeneous epoxidation catalyst to obtain a stream containing alkylene oxide and alcohol, and recycling of from 30 to 95% wt of the stream obtained in step (ii) to step (i).
    Type: Grant
    Filed: October 13, 2010
    Date of Patent: September 13, 2011
    Assignee: Shell Oil Company
    Inventors: Ingmar Hubertus Josephina Ploemen, Eduardus Petrus Simon Schouten, Alexander Jan Van Der Veen
  • Patent number: 7981951
    Abstract: A process for producing an epoxide such as a cycloaliphatic diepoxide by the reaction of an olefin such as a cycloaliphatic diene with hydrogen peroxide (H2O2) as an oxidant in the presence of a catalytic system under pH control for example at a pH of less than about 5. The present invention is advantageously used for the epoxidation of olefinic compounds such as olefins and aliphatic or aromatic dienes.
    Type: Grant
    Filed: June 19, 2007
    Date of Patent: July 19, 2011
    Inventors: Anna Forlin, Massimo Bergamo, Wells Carter, David Jean
  • Publication number: 20110137054
    Abstract: The invention relates to a process for the manufacture of a 1,2-epoxide by catalytic oxidation of a terminal olefin with hydrogen peroxide wherein the catalytic oxidation is performed in a biphasic system comprising an organic phase and an aqueous reaction medium, wherein a water-soluble manganese complex is used as oxidation catalyst, wherein a terminal olefin is used with a solubility at 20° C. of at least 0.01 to 100 g in 1 liter water, and wherein the molar ratio of terminal olefin to hydrogen peroxide is in the range of from 1:0.1 to 1:2.
    Type: Application
    Filed: July 9, 2009
    Publication date: June 9, 2011
    Inventors: Ron Postma, Prasad Muppa
  • Publication number: 20110040092
    Abstract: The invention relates to a process for making HOF.RCN and using it to oxidise organic substrates in a quick and safe way. The process comprises passing diluted fluorine through a conduit and RCN in water through another conduit into a microreactor to form HOF.RCN and reacting this with an organic substrates.
    Type: Application
    Filed: September 5, 2008
    Publication date: February 17, 2011
    Applicant: THE SECRETARY OF STATE FOR DEFENSE
    Inventors: Christopher Murray, Graham Sandford
  • Publication number: 20100228040
    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: Application
    Filed: September 26, 2008
    Publication date: September 9, 2010
    Inventors: Takaaki Kikuchi, Takehiro Zushi, Hirohisa Nitoh
  • Publication number: 20100197945
    Abstract: There is disclosed a method for producing propylene oxide, which includes: reacting propylene, oxygen, and hydrogen in the presence of a noble metal catalyst and a titanosilicate catalyst in a liquid phase containing a polycyclic compound, which is unsubstituted or substituted with at least one substituent selected from Group B below, wherein the polycyclic compound is composed of two or more identical or different ring compounds selected from Group A below and the ring compounds are fused, directly bonded, or bonded by a linkage group selected from the group consisting of an oxygen atom, carbon chain, and a group composed of oxygen atom(s) and a carbon chain, provided that said polycyclic compound is not a polycyclic compound having hydroxy groups or oxo groups at para or. ortho positions. Group A consisting of benzene, cyclopentadiene, cycloheptatriene, furane, pyrane, cyclopentene, cyclopentane, cyclohexane, cyclohexene, cyclohexadiene, cycloheptane, cycloheptene, and cycloheptadiene.
    Type: Application
    Filed: June 19, 2008
    Publication date: August 5, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Hiroaki Abekawa, Tomonori Kawabata, Makoto Yako
  • Publication number: 20100160654
    Abstract: A supported catalyst and a catalyst mixture, useful for the direct epoxidation of olefins, are disclosed. The supported catalyst comprises a noble metal, lead, and a carrier that has been treated by contacting with nitric acid. The catalyst mixture comprises a titanium or vanadium zeolite and the supported catalyst. The invention also includes a process for producing an epoxide comprising reacting an olefin, hydrogen and oxygen in the presence of the catalyst mixture. The process results in significantly reduced alkane byproduct formed by the hydrogenation of olefin.
    Type: Application
    Filed: December 18, 2008
    Publication date: June 24, 2010
    Inventor: Roger A. Grey
  • Patent number: 7723549
    Abstract: A process for preparing at least one target product by partial oxidation and/or ammoxidation of propylene, in which the propylene source used is a propane dehydrogenation, the propane used therein being obtained by a rectificative prepurification of crude propane.
    Type: Grant
    Filed: April 27, 2006
    Date of Patent: May 25, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Armin Diefenbacher, Claus Hechler, Christoph Adami, Martin Dieterle
  • Publication number: 20100081808
    Abstract: [Problems] To provide an efficient process for producing an optically active epoxy compound. [Means For Solving Problems] The process for producing an optically active epoxy compound comprises asymmetrically epoxidizing an unsaturated compound with an oxidizing agent in the presence of an optically active titanium-salen complex, an optically active titanium-salalen complex or an optically active titanium-salan complex, with addition of a buffering agent or a buffer solution. The process can inhibit catalyst degradation, reduce the amount of the catalyst used in the reaction, and inhibit a by-product, compared with the prior art, and can provide an optically active epoxy compound in high chemical yield and optical yield and with high quality, and therefore is an industrially useful process.
    Type: Application
    Filed: March 10, 2008
    Publication date: April 1, 2010
    Inventors: Shoichi Kondo, Yuya Shimada
  • Publication number: 20100048925
    Abstract: A method for producing propylene oxide in which the concentration of an organic peroxide in a reaction solution after an epoxidation step is from 20 to 5,000 ppm by weight based on the amount excluding propylene in the reaction solution, the method comprising an epoxidation step of reacting an organic peroxide with propylene in the presence of a catalyst to obtain propylene oxide and an alcohol, a propylene recovery step of recovering the unreacted propylene in the epoxidation step and recycling the resulting propylene as a raw material of the epoxidation step, and a propylene oxide purification step of distilling the propylene oxide obtained in the epoxidation step to obtain purified propylene oxide.
    Type: Application
    Filed: March 21, 2008
    Publication date: February 25, 2010
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Jun Yamamoto, Shigeru Goto
  • Patent number: 7642365
    Abstract: A unique reactor configuration especially suitable for interphase mass transfer and mixing of multiple phases, i.e. gas(es), liquid(s), and solid(s) where reaction is catalyzed by a solid catalyst comprises a draught tube reactor wherein the solid catalyst particles are maintained in an annular space between the draught tube of the reactor and an annulus-defining wall by means of filter elements positioned downstream and optionally also upstream from the catalyst bed.
    Type: Grant
    Filed: August 3, 2007
    Date of Patent: January 5, 2010
    Assignee: Lyndell Chemical Technology, L.P.
    Inventor: Prakash G. Balan
  • Publication number: 20090287007
    Abstract: Disclosed is a method for making a partially hydrogenated, fully epoxidized vegetable oil derivative. The method includes fully epoxidizing a partially hydrogenated vegetable oil having an iodine value of 70 to 100 g I2/100 grams oil to obtain a partially hydrogenated, fully-epoxidized vegetable oil derivative exhibiting a iodine value less than 4 g I2/100 gram, an acid number less than 1 mg KOH/gram, an EOC from 4.0 to 5.7% and a Gardner Color value of 1 or less.
    Type: Application
    Filed: May 13, 2009
    Publication date: November 19, 2009
    Applicant: CARGILL, INCORPORATED
    Inventors: Timothy Walter Abraham, Charles Michael Tanger
  • Publication number: 20090163728
    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: Application
    Filed: March 9, 2005
    Publication date: June 25, 2009
    Applicant: THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA
    Inventors: Patrick Walsh, Alice E. Lurain, Ann R. Kelly, Aaron G. Maestri
  • Patent number: 7544818
    Abstract: Process for the continuous recirculation of the olefin which has not been reacted in the oxidation of olefins by means of hydroperoxide to give oxiranes and is present in the offgas stream formed during the oxidation, which comprises the steps (i) to (iii) (i) separating the olefin from the offgas stream by absorption in a hydrocarbon, (ii) desorbing the olefin from the hydrocarbon, (iii) recirculating the olefin obtained in step (ii) to the oxidation process.
    Type: Grant
    Filed: October 23, 2003
    Date of Patent: June 9, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Bassler, Hans-Georg Goebbel, Joaquim Henrique Teles, Peter Rudolf
  • Publication number: 20090131693
    Abstract: A process for the selective oxidation of olefins to epoxides comprising the step of contacting the olefin (propylene or ethylene) with an oxidant (hydrogen peroxide) in the presence of a Lewis acid oxidation catalyst (MTO), organic base (pyridine or its N-oxide), in a solvent system comprising an organic water-miscible solvent (methanol). The system is pressurized using either the olefin itself or by adding an inert pressurizing gas (nitrogen) to increase the pressure between 230 and 700 psi at a temperature between 0.7 and 1.3 times the critical temperature of the olefin. The resulting increased solubility of the olefin in the organic solvent system increases the selectivity and yield of the desired epoxide (propylene oxide or ethylene oxide).
    Type: Application
    Filed: September 8, 2008
    Publication date: May 21, 2009
    Inventors: Daryle H. Busch, Bala Subramaniam, Hyun-Jin Lee, Tie-Pan Shi
  • Patent number: 7482478
    Abstract: Diastereoselective epoxidation of allylically substituted alkenes using metalloporphyrins as catalyst provides high trans-selectivities (i.e., trans-:cis-epoxide ratio). A diversity of cycloalkenes bearing different allylic substituents are shown to be efficiently epoxidized to afford the corresponding trans-epoxides with excellent trans-selectivities (up to >98%) and good yields (up to 99%). Acyclic allylic alkenes bearing different allylic substituents are efficiently epoxidized to afford the corresponding erythro-epoxides with good erythro-selectivities. The metalloporphyrin-catalyzed reactions exhibit up to 20 times higher trans-selectivities than the conventional method using m-chloroperoxybenzoic acid as oxidant.
    Type: Grant
    Filed: March 16, 2005
    Date of Patent: January 27, 2009
    Assignee: The University of Hong Kong
    Inventors: Chi-Ming Che, Man-Kin Wong
  • Publication number: 20080154052
    Abstract: The present invention relates to an improved epoxidation process and an improved epoxidation reactor. The present invention makes use of a reactor which comprises a plurality of microchannels. Such process microchannels may be adapted such that the epoxidation and optionally other processes can take place in the microchannels and that they are in a heat exchange relation with channels adapted to contain a heat exchange fluid. A reactor comprising such process microchannels is referred to as a “microchannel reactor”. The invention also provides a method of installing an epoxidation catalyst in a microchannel reactor. The invention also provides a method of preparing an epoxidation catalyst. The invention also provides an epoxidation catalyst. The invention also provides a certain process for the epoxidation of an olefin and a process for the preparation of a chemical derivable from an olefin oxide. The invention also provides a microchannel reactor.
    Type: Application
    Filed: December 20, 2006
    Publication date: June 26, 2008
    Inventors: Jeroen Willem Bolk, Alouisius Nicolaas Renee Bos, Wayne Errol Evans, John Robert Lockemeyer, Paul Michael McAllister, Bernardus Franciscus Josef Marie Ramakers, Dominicus Maria Rekers, Mathias Jozef Paul Slapak
  • Publication number: 20080154051
    Abstract: The present invention relates to an improved epoxidation process and an improved epoxidation reactor. The present invention makes use of a reactor which comprises a plurality of microchannels. Such process microchannels may be adapted such that the epoxidation and optionally other processes can take place in the microchannels and that they are in a heat exchange relation with channels adapted to contain a heat exchange fluid. A reactor comprising such process microchannels is referred to as a “microchannel reactor”. The invention also provides a method of installing an epoxidation catalyst in a microchannel reactor. The invention also provides a method of preparing an epoxidation catalyst. The invention also provides an epoxidation catalyst. The invention also provides a certain process for the epoxidation of an olefin and a process for the preparation of a chemical derivable from an olefin oxide. The invention also provides a microchannel reactor.
    Type: Application
    Filed: December 20, 2006
    Publication date: June 26, 2008
    Inventors: Jeroen Willem Bolk, Alouisius Nicolaas Renee Bos, Wayne Errol Evans, John Robert Lockemeyer, Paul Michael Mcallister, Bernardus Franciscus Josef Marie Ramakers, Dominicus Maria Rekers, Mathias Jozef Paul Slapak
  • Publication number: 20080132717
    Abstract: In a propylene oxide process wherein propylene is oxidized in a reaction mixture comprised of a solid catalyst slurried in a solvent and wherein propane and propylene are separated by distillation in a C3 splitter, the improvement of removing exothermic heat of reaction by indirect heat exchange with propane, separating the heated propane into a liquid and a vapor fraction and heating the C3 splitter distillation with the said propane vapor.
    Type: Application
    Filed: December 4, 2006
    Publication date: June 5, 2008
    Inventors: Bernard Cooker, John H. Speidel
  • Patent number: 7301038
    Abstract: A process for the preparation of alkylene oxide, which process involves passing a feed containing an organic hydroperoxide and alkene through a bank of at least two serially connected reactors containing epoxidation catalyst and withdrawing a product stream having alkylene oxide and an alcohol as reaction products, in which bank of reactors the temperature of the feed is controlled such that during operation the outlet temperature of the final reactor is at least 4° C. higher than the outlet temperature of the first reactor.
    Type: Grant
    Filed: May 3, 2002
    Date of Patent: November 27, 2007
    Assignee: Shell Oil Company
    Inventors: Johannes Petrus Van Der Linden, Ingmar Hubertus Josephina Ploemen, Augustinus Santen, Alexander Jan Van Der Veen
  • 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: 7153986
    Abstract: A method is provided for producing propylene oxide, wherein propylene is reacted with hydrogen peroxide in the presence of an organic solvent and a crystalline titanosilicate catalyst having an MWW structure containing Ti, the Ti having been incorporated during crystallization.
    Type: Grant
    Filed: February 28, 2003
    Date of Patent: December 26, 2006
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroaki Abekawa, Masaru Ishino
  • 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: 7049450
    Abstract: A process for the purification of a crude propene oxide containing methanol and acetaldehyde by a continuously operated extractive distillation using an extraction solvent lowering the volatility of methanol and feeding a compound containing an unsubstituted NH2 group capable of reacting with acetaldehyde to a distillation column at a point above the feeding point of the crude propene oxide to give a purified propene oxide containing less than 100 ppm methanol and less than 100 ppm acetaldehyde. There is also disclosed a process for the catalytic epoxidation of propene that includes this purification stage.
    Type: Grant
    Filed: November 26, 2003
    Date of Patent: May 23, 2006
    Assignees: Degussa AG, UHDE GmbH
    Inventors: Willi Hofen, Thomas Haas, Wolfgang Wöll, Georg Thiele
  • Patent number: 7030255
    Abstract: Catalysts useful for oxidation reactions are disclosed. The catalysts comprise a titanium zeolite, a transition metal, and a polymer, wherein at least one of the titanium zeolite or transition metal is encapsulated within a thin layer of the polymer. The catalysts are easy to prepare and use, they are easy to recover and reuse, and they provide good conversions in a variety of important oxidation processes, including propylene epoxidation. The invention includes a process which comprises oxidizing an organic compound in the presence of hydrogen, oxygen, and the catalyst, wherein the transition metal catalyzes formation of hydrogen peroxide in situ.
    Type: Grant
    Filed: March 9, 2004
    Date of Patent: April 18, 2006
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Roger A. Grey, Bi Le-Khac
  • Patent number: 6884898
    Abstract: Propylene oxide is formed by reaction of propylene with molecular oxygen in a high boiling solvent containing slurried solid catalyst, the light components are flashed and the remaining liquid containing slurried catalyst is recycled.
    Type: Grant
    Filed: December 8, 2003
    Date of Patent: April 26, 2005
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Jay F. Miller
  • Patent number: 6838572
    Abstract: A continuous process for the epoxidation of olefins with hydrogen peroxide in the presence of a heterogeneous catalyst promoting the epoxidation reaction, whereby the aqueous reaction mixture contains i) an olefin; ii) hydrogen peroxide; iii) less than 100 wppm of alkali metals, earth alkali metals, both irrespective whether in ionic, complex or covalently bonded form, bases or cations of bases having a pkB of less than 4.5, or combinations thereof; and, iv) at least 100 wppm of bases or cations of bases having a pkB of at least 4.5 or combinations thereof, whereby the wppm are based on the total weight of hydrogen peroxide in the reaction mixture.
    Type: Grant
    Filed: September 24, 2003
    Date of Patent: January 4, 2005
    Assignees: Degussa AG, Uhde GmbH
    Inventors: Thomas Haas, Claudia Brasse, Guido Stochniol, Willi Hofen, Wolfgang Wöll, Georg Thiele