Preparing Alkyl Esters From Olefins Patents (Class 560/247)
  • Publication number: 20140303398
    Abstract: The present invention discloses a method for producing vinyl acetate. Inert gas is introduced into cycling gas to improve the explosion limit of oxygen, enlarge a stable area of a reaction system and improve the oxygen concentration of the reaction system, thus reducing the reaction temperature, prolonging the service life of a catalyst, and improving the selectivity of the vinyl acetate. The inert gas is nitrogen or a mixture of nitrogen and methane. The concentration of the inert gas at the inlet of a reactor is 8 to 30 mol %. The molar concentration of the oxygen at the inlet of the reactor is 10.5 to 12 mol %.
    Type: Application
    Filed: November 6, 2012
    Publication date: October 9, 2014
    Applicants: Tianjin University
    Inventors: Minhua Zhang, Xiuqin Dong, Minli Tao, Cheng Liu, Shengli Ouyang, Haoxi Jiang, Jing Ma, Guiming Li
  • Publication number: 20140194649
    Abstract: Yield and selectivity of olefin acetoxylation are improved through the use of successive catalyst zones of different reactivities, the successive zones contained in one or more reaction tubes arranged is parallel.
    Type: Application
    Filed: August 23, 2012
    Publication date: July 10, 2014
    Applicant: WACKER CHEMIE AG
    Inventors: Anja Roscher, Hans-Juergen Eberle, Roland Heidenreich, Herbert Jung
  • Publication number: 20130338378
    Abstract: The invention relates to a shaped catalyst body for the catalytic conversion of organic and inorganic components in fixed-bed reactors, wherein the shaped catalyst body is formed as cylinder with a base, a cylinder surface, a cylinder axis and at least one continuous opening running parallel to the cylinder axis, and the base of the cylinder has at least four corners.
    Type: Application
    Filed: November 22, 2011
    Publication date: December 19, 2013
    Inventors: Andreas Reitzmann, Willi Michael Brandstädter, Leopold Streifinger, Marvin Estenfelder
  • Patent number: 8586780
    Abstract: A shell catalyst for producing vinyl acetate monomer (VAM), comprising an oxidic porous catalyst support, formed as a shaped body, with an outer shell in which metallic Pd and Au are contained. To provide a shell catalyst for producing VAM which has a relatively high activity and can be obtained at relatively low cost, the catalyst support is doped with at least one oxide of an element selected from the group consisting of Li, P, Ca, V, Cr, Mn, Fe, Sr, Nb, Ta, W, La and the rare-earth metals.
    Type: Grant
    Filed: May 30, 2008
    Date of Patent: November 19, 2013
    Assignee: Sued-Chemie IP GmbH & Co. KG
    Inventors: Alfred Hagemeyer, Gerhard Mestl, Peter Scheck
  • Publication number: 20130210984
    Abstract: The invention relates to secondary alcohols produced by contacting an olefin and a carboxylic acid with a zeolite, esters made therefrom, and to plasticizer compositions comprising the esters.
    Type: Application
    Filed: June 3, 2011
    Publication date: August 15, 2013
    Applicant: ExxonMobil Chemical Patents Inc.
    Inventors: Karla S. Colle, Allen D. Godwin
  • Patent number: 8440855
    Abstract: An integrated process for the production of acetic acid, ethylene and vinyl acetate monomer comprising the steps of: (a) evaporating at least part of an ethanol feed stock (b) producing in a first reaction zone a first product stream comprising acetic acid by oxidative or partly oxidative dehydrogenation of ethanol feed stock; (c) producing in a second reaction zone a second product stream comprising ethylene from an ethanol feed stock; (d) reacting in a third reaction zone an acetic acid reaction stream containing at least a portion of the acetic acid from the first reaction zone with an ethylene reaction stream containing at least a portion of the ethylene product from the second reaction zone and with oxygen to a third product stream comprising vinyl acetate monomer; (e) passing at least a portion of the third product stream to a distillation section and isolating at least a portion of the vinyl acetate monomer; (f) supplying at least part of reaction heat from the third reaction zone to provide heat for
    Type: Grant
    Filed: December 8, 2010
    Date of Patent: May 14, 2013
    Assignee: Haldor Topsoe A/S
    Inventors: Bodil Voss, Rachid Mabrouk, Claus Hviid Christensen
  • Publication number: 20120264970
    Abstract: A process is disclosed for the production of vinyl acetate where a mixture of ethylene, acetic acid, and oxygen is reacted in the presence of a catalyst to produce a product mixture of vinyl acetate, ethylene, carbon dioxide, acetic acid, water, ethyl acetate, and ethylene glycol diacetate. The product mixture contains both a gaseous phase and a liquid phase, which are separated. The gas phase contains at least carbon dioxide, which is removed via gas stream. The crude vinyl acetate stream is removed via a liquid stream. The crude vinyl acetate is then further separated to isolate a stream containing at the majority of the ethylene glycol diacetate. The ethylene glycol diacetate stream is then methanolyzed in the presence of a methanolyzing catalyst, to recover methyl acetate, which can be optionally recycled as a feed stock to an acetic acid plant.
    Type: Application
    Filed: April 15, 2011
    Publication date: October 18, 2012
    Inventors: Brian SALISBURY, Michael E. Fitzpatrick, Wayne Joseph Brtko, Noel C. Hallinan
  • Publication number: 20120053361
    Abstract: The invention relates to a method for producing vinyl acetate in a heterogeneously catalyzed, continuous gas-phase process by reacting ethylene with acetic acid and oxygen in a reactor, and a) separating the product gas flow essentially containing ethylene, vinyl acetate, acetic acid, water, carbon dioxide, and other inert gases, and b) feeding a circulating gas flow containing ethylene and CO2 back into the reactor, c) the circulating gas flow being compressed in a circulating gas compressor before being fed back into the reactor, and d) a partial flow of the circulating gas is branched off on the suction side or the pressure side of the circulating gas compressor and is fed to a CO2 scrubbing process, and e) is scrubbed in a water scrubber before the CO2 scrubbing process, characterized in that f) after the CO2 scrubbing process, the partial flow, together with ethylene as a propellant, is fed, by means of a jet compressor, to the circulating gas on the pressure side of the circulating gas compressor and do
    Type: Application
    Filed: April 22, 2010
    Publication date: March 1, 2012
    Applicant: Wacker Chemie AG
    Inventors: Willibald Dafinger, Peter Holl, Johann Wagner
  • Patent number: 7491843
    Abstract: Acetic acid and/or vinyl acetate are produced by an integrated process which comprises the steps: (a) contacting in a first reaction zone a gaseous feedstock comprising ethylene and/or ethane and optionally steam with a molecular oxygen-containing gas in the presence of a catalyst active for the oxidation of ethylene to acetic acid and/or ethane to acetic acid and ethylene to produce a first product stream comprising acetic acid, water and ethylene (either as unreacted ethylene and/or as co-produced ethylene) and optionally also ethane, carbon monoxide, carbon dioxide and/or nitrogen; (b) contacting in a second reaction zone in the presence or absence of additional ethylene and/or acetic acid at least a portion of the first gaseous product stream comprising at least acetic acid and ethylene and optionally also one or more of water, ethane, carbon monoxide, carbon dioxide and/or nitrogen with a molecular oxygen-containing gas in the presence of a catalyst active for the production of vinyl acetate to produce
    Type: Grant
    Filed: November 2, 2001
    Date of Patent: February 17, 2009
    Assignee: BP Chemicals Limited
    Inventors: Simon Jobson, Derrick John Watson
  • Patent number: 7446221
    Abstract: A practical, economical process for making tricyclodecenyl esters is disclosed. After reacting a lower carboxylic acid and a dicyclopentadiene in the presence of triflic acid to form the ester, the reaction mixture is distilled in the presence of a base to isolate a fragrance-quality tricyclodecenyl ester. Adding enough base to neutralize the triflic acid enables a distillation-only purification, facilitates starting material recovery, and avoids drawbacks of a basic workup.
    Type: Grant
    Filed: June 5, 2007
    Date of Patent: November 4, 2008
    Assignee: Equistar Chemicals, LP
    Inventor: Mikhail Y. Lebedev
  • Patent number: 7390918
    Abstract: An integrated process for the production of an alkenyl carboxylate, such as vinyl acetate which process comprises the steps of (a) contacting in an oxidation reaction zone a C2 to C4 alkane, such as ethane, a molecular oxygen-containing gas, optionally the corresponding alkene and optionally water, in the presence of a catalyst to produce a stream comprising alkene, carboxylic acid and water; (b) separating at least a portion of the stream from step (a) into a fraction comprising the alkene and a fraction comprising the carboxylic acid and water; (c) contacting in a second reaction zone at least a portion of said alkene fraction produced in step (b), a carboxylic acid and a molecular oxygen-containing gas, in the presence of a catalyst to produce a product stream comprising an alkenyl carboxylate, water and carboxylic acid; (d) separating at least a portion of the product stream from step (c) and at least a portion of the carboxylic acid and water fraction produced in step (b) by azeotropic distillation into
    Type: Grant
    Filed: December 4, 2002
    Date of Patent: June 24, 2008
    Assignee: BB Chemicals Limited
    Inventors: Robert William Clarke, Mark Stephen Roberts
  • Patent number: 7153996
    Abstract: This invention relates to a process for producing a mixture of levulinic acid esters and formic acid esters from biomass and olefins, and the composition prepared therefrom. This invention also relates to usage of the mixture of these esters as fuel and as fuel additives for gasoline fuel, diesel fuel, and biofuel.
    Type: Grant
    Filed: April 1, 2003
    Date of Patent: December 26, 2006
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Paul Joseph Fagan, Leo Ernest Manzer
  • Patent number: 6998026
    Abstract: A tert-C4–C8-alkyl (meth)acrylate is prepared by reacting (meth)acrylic acid with an olefin of the formula where R1 and R2, which may be identical or different, are methyl or ethyl and R3 is H, methyl or ethyl, in homogeneous phase in the presence of an acidic catalyst and isolating the tert-C4–C8-alkyl (meth)acrylate from the reaction mixture, by a process in which the catalyst is separated off as residue by a two-stage distillation of the reaction mixture and the tert-C4–C8-alkyl (meth)acrylate is isolated from the distillates. The novel process makes it possible to use acetic acid-containing (meth)acrylic acid. The danger of cleavage of the ester and of polymerization of (meth)acrylic compounds is reduced.
    Type: Grant
    Filed: July 27, 2001
    Date of Patent: February 14, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Ruprecht Kroker, Gerhard Nestler, Werner Schmitt, Winfried Schumm
  • Patent number: 6949671
    Abstract: Process for treating a mixed C4 stream comprising iso-butene and 1,3-butadiene by (a) reacting the stream with acetic acid in an addition reactor, (b) withdrawing product comprising iso-butene acetate, sec-butenyl acetate, n-butenyl acetate and t-butyl acetate, and recovering n-butenyl acetate from the product and separating and recycling t-butyl acetate to the addition reactor. The process provides increased efficiency of acetic acid utilisation together with useful products, e.g. n-butenyl and sec-butenyl acetates which can be separated and sold as such or converted to other products. The unreacted isobutene can be separated and used as such, or recycled and allowed to dimerise to di-isobutene, another useful product.
    Type: Grant
    Filed: August 28, 2002
    Date of Patent: September 27, 2005
    Assignee: The University of Southern Mississippi Research Foundation
    Inventors: Benjamin Patrick Gracey, Nicholas John Hazel
  • Patent number: 6946570
    Abstract: This invention relates to a process for the production of lower aliphatic esters by reacting a lower olefin with a saturated lower aliphatic mono-carboxylic acid in the vapor phase in the presence of a heteropolyacid catalyst in a plurality of reactors set up in series such that the reactant gases exiting from a first reactor are fed as the feed gas to a second reactor and those exiting from the second reactor are fed as the feed gas to a third reactor and so on for the subsequent reactors. An aliquot of the reactant monocarboxylic acid is introduced into the feed gas to the second and subsequent reactors so as to maintain the olefin to monocarboxylic acid ratio in the feed gas to each of the second and subsequent reactors within a pre-determined range.
    Type: Grant
    Filed: February 25, 2004
    Date of Patent: September 20, 2005
    Assignee: BP Chemicals Limited
    Inventors: Stanley John Becker, Geoffrey Bryne, Simon Frederick Thomas Froom, Stephen Robert Hodge
  • Patent number: 6849759
    Abstract: A process for producing an ester comprising reacting a carboxylic acid and ethylene in the presence of an acid catalyst in a vapor phase, wherein the concentration of olefin having 3 or more carbon atoms in the starting materials is controlled to 10,000 ppm or less in terms of the molar ratio to the total of the olefin and ethylene. The deterioration of the catalyst can be remarkably prevented from proceeding and a continuous and stable operation can be performed for a long time.
    Type: Grant
    Filed: October 24, 2000
    Date of Patent: February 1, 2005
    Assignee: Showa Denko K.K.
    Inventors: Hiroshi Uchida, Tomoyoshi Higashi, Etsuko Kadowaki, Takashige Miyanari, Wataru Oguchi
  • Patent number: 6825149
    Abstract: A shell impregnated catalyst of Pd-Au produced on a silica support to have a Pd loading of 1.8 g/L of catalyst to about 7.2 g/L and a Au to Pd weight ratio of 0.3 to 2.0 by impregnating the support with aqueous solutions of palladium and gold salts or acids and thereafter precipitating water insoluble compounds of Pd and Au on the with alkali metal silicate or hydroxide solutions, then dried, and the surface precipitated compounds of Pd and Au are then reduced by reaction with ethylene or hydrogen at a temperature of greater than 150° C. up to 310° C. or with hydrogen up to 299° C. until substantially all of the Pd and Au contents are reduced to a free metal state, after which the support is impregnated with potassium acetate to an extent of 6 to 7 weight percent of the weight of the total catalyst.
    Type: Grant
    Filed: June 19, 2002
    Date of Patent: November 30, 2004
    Assignee: Saudi Basic Industries Corporation
    Inventor: Alla Konstantin Khanmamedova
  • Patent number: 6809218
    Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity.
    Type: Grant
    Filed: October 7, 2003
    Date of Patent: October 26, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6794535
    Abstract: Process for the production of lower aliphatic esters comprising reacting a lower olefin with a saturated lower aliphatic monocarboxylic acid in the vapor phase in the presence of a heteropolyacid catalyst. The reaction is carried out in a plurality of reactors set up in series, and the feedstock is rendered substantially free of metallic or metal compound impurities prior to being brought into contact with the heteropolyacid catalyst.
    Type: Grant
    Filed: January 3, 2001
    Date of Patent: September 21, 2004
    Assignee: BP Chemicals Limited
    Inventors: Simon Frederick Thomas Froom, Stephen Robert Hodge, Witold Franciszek Pacynko
  • Patent number: 6770791
    Abstract: Disclosed is an olefin containing stream from an oxygenate to olefin process, and a process for making olefin dimer and oligomer product from the olefin containing stream using a nickel based oligomerization catalyst. The dimer/oligomer product is optionally converted to hydroformylated product. The olefin containing stream that is used to make the higher olefin product has low levels of impurities including nitrogen, sulfur and/or chlorine.
    Type: Grant
    Filed: April 29, 2003
    Date of Patent: August 3, 2004
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Georges Mathys, John Stephen Godsmark, Marcel Janssen, Luc Roger Martens, Hubertus Joseph Beckers, Eddy Theophile Andrea Van Driessche, Raphael Frans Ivo Caers, John Richard Shutt
  • Patent number: 6696598
    Abstract: A process for producing a lower aliphatic carboxylic acid ester by a gas phase esterification reaction starting from a lower aliphatic carboxylic acid and a lower olefin, comprising adding a lower alcohol corresponding to a hydrate of a lower olefin to the gas phase reaction product, condensing a lower aliphatic carboxylic acid and the lower alcohol and while allowing the conversion into a lower aliphatic carboxylic acid ester to proceed, separating the lower aliphatic carboxylic acid ester. Productivity is increased due to the improvement of the conversion of a lower aliphatic carboxylic acid.
    Type: Grant
    Filed: December 14, 2001
    Date of Patent: February 24, 2004
    Assignee: Showa Denko K.K.
    Inventors: Ayumu Fujita, Etsuko Kadowaki, Meiko Saihata, Hiroshi Uchida
  • Patent number: 6696597
    Abstract: The present invention relates to metathesis syntheses for insect sex-attractant pheromones or their components, such as E-5-decenyl acetate, the major component of the Peach Twig Borer pheromone; (5R,6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone; E9,Z11-hexadecadienal, the pecan nut casebearer moth pheromone; 9-tetradecenyl formate, an analog of the Diamondback Moth (DBM) pheromone; 11-tetradecenyl acetate, the Omnivorous Leafroller (OLR) pheromone; E-4-tridecenyl acetate, the major component of the Tomato Pinworm (TPW) pheromone; E,E-8,10-dodecadienol, the Codling Moth (CM) pheromone. The syntheses preferably employ a Class I-IV metathesis catalyst, entail few reaction steps, use generally commercially available starting materials, and have relatively short process times. These syntheses produce good yields without the need for expensive or sophisticated equipment.
    Type: Grant
    Filed: April 10, 2001
    Date of Patent: February 24, 2004
    Assignee: TillieChem, Inc.
    Inventors: Richard L. Pederson, Robert H. Grubbs
  • Patent number: 6624325
    Abstract: A catalyst for producing lower fatty acid esters through esterification of a lower aliphatic carboxylic acid with a lower olefin, comprising a heteropoly acid or a, salt thereof held on a carrier, and having a specific surface area of the catalyst, as measured by a BET method, of 65 m2/g-350 m2/g. A process for producing the catalyst and a process for producing a lower fatty acid ester by using the catalyst are also provided.
    Type: Grant
    Filed: June 29, 2000
    Date of Patent: September 23, 2003
    Assignee: Showa Denko K. K.
    Inventors: Tomoyoshi Higashi, Kousuke Narumi, Hideyuki Kamei, Hiroshi Uchida
  • Patent number: 6465683
    Abstract: Process for making a butyl ester from butadiene, comprising (a) reacting butadiene with a saturated aliphatic monocarboxylic acid to form a mixture of n-butenyl and secondary butenyl esters, (b) separating the n-butenyl ester from the secondary butenyl ester, and (c) hydrogenating the n-butenyl ester separated in step (b) in the presence of a catalyst to the corresponding n-butyl ester.
    Type: Grant
    Filed: April 30, 2001
    Date of Patent: October 15, 2002
    Assignee: BP Chemicals Limited
    Inventors: Benjamin Patrick Gracey, Norbert Walter Josef Kamp
  • Patent number: 6420308
    Abstract: A shell impregnated catalyst of Pd—Au produced on a silica support to have a Pd loading of 1.8 g/L of catalyst to about 7.2 g/L and a Au to Pd weight ratio of 0.3 to 2.0 by impregnating the support with aqueous solutions of palladium and gold salts or acids and thereafter precipitating water insoluble compounds of Pd and Au on the with alkali metal silicate or hydroxide solutions, then dried, and the surface precipitated compounds of Pd and Au are then reduced by reaction with ethylene or hydrogen at a temperature of greater than 150° C. up to 310° C. or with hydrogen up to 299° C. until substantially all of the Pd and Au contents are reduced to a free metal state, after which the support is impregnated with potassium acetate to an extent of 6 to 7 weight percent of the weight of the total catalyst.
    Type: Grant
    Filed: July 7, 2000
    Date of Patent: July 16, 2002
    Assignee: Saudi Basic Industries Corp
    Inventor: Alla Konstantin Khanmamedova
  • Publication number: 20020028965
    Abstract: 1.
    Type: Application
    Filed: November 2, 2001
    Publication date: March 7, 2002
    Applicant: BP Chemicals Limited
    Inventors: Simon Jobson, Derrick John Watson
  • Patent number: 6333430
    Abstract: A process for preparing a tert-alkyl carboxylic acid ester represented by the formula (III): wherein R1 is an organic group; and each of R2 and R3 is independently an alkyl group having 1 to 4 carbon atoms, comprising reacting a carboxylic acid represented by the formula (I): R1—COOH  (I) wherein R1 is as defined above, with a vinylidene compound represented by the formula (II): wherein R2 and R3 are as defined above, in the presence of a phosphorus halide. The tert-alkyl carboxylic acid ester can be used as intermediates for pharmaceuticals such as antibiotics.
    Type: Grant
    Filed: May 2, 2000
    Date of Patent: December 25, 2001
    Assignee: Sumika Fine Chemicals Co., Ltd.
    Inventors: Tetsuya Shintaku, Kiyoshi Sugi, Tadashi Katsura, Nobushige Itaya
  • Publication number: 20010047107
    Abstract: This invention relates to a process for the production of lower aliphatic esters, said process comprising reacting a lower olefin with saturated lower aliphatic mono-carboxylic acid in the vapour phase in the presence of a heteropolyacid catalyst, characterised in that the reactants are rendered substantially free of basic nitrogenous compounds prior to being brought into contact with the heteropolyacid catalyst.
    Type: Application
    Filed: January 3, 2001
    Publication date: November 29, 2001
    Inventors: Eric Nicholas Coker, Simon Frederick Thomas Froom, Warren John Smith
  • Publication number: 20010029307
    Abstract: Process for the production of lower aliphatic esters comprising reacting a lower olefin with a saturated lower aliphatic monocarboxylic acid in the vapor phase in the presence of a heteropolyacid catalyst. The reaction is carried out in a plurality of reactors set up in series, and the feedstock is rendered substantially free of metallic or metal compound impurities prior to being brought into contact with the heteropolyacid catalyst.
    Type: Application
    Filed: January 3, 2001
    Publication date: October 11, 2001
    Inventors: Simon Frederick Thomas Froom, Stephen Robert Hodge, Witold Franciszek Pacynko
  • Patent number: 6242640
    Abstract: A tertiary olefin such as isobutylene is reacted with a lower unsaturated carboxylic acid to produce the ester in the presence of a large pore zeolite catalyst such as Zeolite Y, Zeolite beta or Zeolite X, the reaction can be illustrated by the equation
    Type: Grant
    Filed: October 7, 1999
    Date of Patent: June 5, 2001
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Lawrence J. Karas
  • Patent number: 6194602
    Abstract: A tertiary olefin such as isobutylene is reacted with a lower carboxylic acid to produce the ester in the presence of a large pore zeolite catalyst such as Zeolite Y, Zeolite beta or Zeolite X.
    Type: Grant
    Filed: April 16, 1998
    Date of Patent: February 27, 2001
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Lawrence J. Karas
  • Patent number: 6187949
    Abstract: Process for the production of lower aliphatic esters by bringing together in an addition reaction a lower olefin and a saturated, lower aliphatic, mono-carboxylic acid in the vapor phase into contact with a heterpolyacid catalyst. The reactant olefin and acids and any recycled feeds are rendered substantially free of aldehydes impurities prior to being brought into contact with the heterpolyacid catalyst. Acetaldehyde is a catalyst poison and removal of these from the feeds prolongs life and activity of the heteropolyacid catalyst.
    Type: Grant
    Filed: January 22, 1999
    Date of Patent: February 13, 2001
    Assignee: BP Chemicals Limited
    Inventors: Simon Frederick Thomas Froom, Stephen Robert Hodge, Bhushan Sharma
  • Patent number: 6090986
    Abstract: Esters of branched C.sub.9 alcohols suitable as plasticizers are formed by esterification of a C.sub.9 alcohol produced by the aldol condensation from propanal and a C.sub.6 aldehyde and hydrogenation, the propanal optionally having been made from natural gas streams.
    Type: Grant
    Filed: October 27, 1997
    Date of Patent: July 18, 2000
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Allen David Godwin, Richard Henry Schlosberg, Frank Hershkowitz, Michael G. Matturro, Gabor Kiss, Kirk Christian Nadler, Philippe Louis Buess, Richard C. Miller, Paul William Allen, Harry William Deckman, Raf Caers, Edmund John Mozeleski, Robert P Reynolds, Francis Joseph Healy
  • Patent number: 6049011
    Abstract: A dilute ethylene stream, e.g., one produced by steam cracking, is oxonated to yield propanal, without the need to separate other lower hydrocarbons.
    Type: Grant
    Filed: October 15, 1997
    Date of Patent: April 11, 2000
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Gabor Kiss, Michael G Matturro, Harry William Deckman, Frank Hershkowitz, David R. Lumgair, Jr., Gary F Janda, Daniel N King
  • Patent number: 6018076
    Abstract: An olefin such as isobutylene is reacted with a carboxylic acid to produce the ester in the presence of an alkanol modifying agent effective to suppress olefin polymerization, at least part of the modifying agent being formed in situ by reaction of the olefin and water.
    Type: Grant
    Filed: February 25, 1998
    Date of Patent: January 25, 2000
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Michael J. Szady, Ahmad Soltani-Ahmadi
  • Patent number: 5994578
    Abstract: An olefin such as isobutylene is reacted with a carboxylic acid to produce the ester in the presence of a modifying agent effective to suppress olefin polymerization, the feed to the reaction containing not more than 0.7 mols water per mol of olefin.
    Type: Grant
    Filed: February 11, 1998
    Date of Patent: November 30, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Lawrence J. Karas
  • Patent number: 5973193
    Abstract: A method of producing ethyl acetate by reacting acetic acid with ethylene in the presence of a solid acidic catalyst comprising a zeolite selected from the group consisting of MCM-22, MCM-49, MCM-56, ZSM-5 and zeolite-Beta.
    Type: Grant
    Filed: July 16, 1998
    Date of Patent: October 26, 1999
    Assignee: Mobil Oil Corporation
    Inventors: Robert A. Crane, Stephen H. Brown, Lorenzo De Caul
  • Patent number: 5866714
    Abstract: An olefin such as isobutylene is reacted with a carboxylic acid to produce the ester in the presence of an alkanol modifying agent effective to suppress olefin polymerization, at least part of the modifying agent being formed in situ by reaction of the olefin and water.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: February 2, 1999
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Michael J. Szady, Ahmad Soltani-Ahmadi
  • Patent number: 5861530
    Abstract: This invention relates to a process for the production of lower aliphatic esters by reacting a lower olefin with a saturated lower aliphatic mono-carboxylic acid in the vapor phase in the presence of a heteropolyacid catalyst characterized in that an amount of water in the range from 1-10 mole % based on the total of the olefin, aliphatic mono-carboxylic acid and water is added to the reaction mixture during the reaction. The presence of water enhances the yield of the desired ester. The reaction mixture may optionally contain a di-ether to minimize the by-products.The process is particularly suitable for producing ethyl acetate from ethylene and acetic acid in the presence of water.
    Type: Grant
    Filed: July 26, 1996
    Date of Patent: January 19, 1999
    Assignee: BP Chemicals Limited
    Inventors: Martin Philip Atkins, Bhushan Sharma
  • Patent number: 5827939
    Abstract: Use of at least one heteropolyacid H.sub.n A.sub.a D.sub.c O.sub.y.xH.sub.2 O where A is phosphorus, boron, silicon, germanium, tin, arsenic, antimony, copper, nickel, cobalt, iron, cerium, thorium, chromium and mixtures thereof; D is molybdenum, tungsten, vanadium and combinations thereof; a is 0.1-10; c is 6-18; n is the number of acidic hydrogens in the heteropolyacid and is a number above 1; y is the number of oxygens in the heteropolyacid and is a number of 10-70; and x is the number of moles of water of crystal-lisation and is a number of 0-40, as catalyst in the preparation of esters of unsaturated carboxylic acids by direct esterification of acids with alcohols or by transesterification, these reactions being carried out in the liquid phase.
    Type: Grant
    Filed: December 22, 1993
    Date of Patent: October 27, 1998
    Assignee: Atochem
    Inventor: Eric Paumard
  • Patent number: 5789609
    Abstract: Disclosed are an optically active diphosphine represented by formula: ##STR1## wherein R represents a lower alkyl group having 1 to 4 carbon atoms; Ar represents a phenyl group which may be substituted with a lower alkyl group having 1 to 4 carbon atoms and/or a lower alkoxy group having 1 to 4 carbon atoms, a transition metal complex containing the diphosphine as a ligand, and a process for producing an optically active .delta.-oxo-.alpha.-cyano ester using the transition metal complex as a catalyst.
    Type: Grant
    Filed: October 22, 1997
    Date of Patent: August 4, 1998
    Assignee: Takasago International Corporation
    Inventors: Kyoko Tamao, Koji Inagaki, Noboru Sayo
  • Patent number: 5681803
    Abstract: There is disclosed a detergent composition containing, as an essential ingredient, at least one member selected from three types of .alpha.-sulfo-fatty acid derivatives as represented by following formulas (1), (2) and (3): ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each an alkyl group or an alkenyl group, each having from 6 to 24 carbon atoms;R.sub.5 is an alkyl group having from 1 to 4 carbon atoms;M.sub.1, M.sub.2, M.sub.3 and M.sub.4 are each a hydrogen atom or a cation capable of forming a salt;AO is an oxyalkylene group or a polyvalent alcohol residue; andp, m and n are each a positive number.The detergent compositions are very low in irritability to the body and have a low critical micelle concentration and a low Krafft point. Further, they are highly soluble in water and they can be used in the form of powder or liquid.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: October 28, 1997
    Assignee: Lion Corporation
    Inventors: Tomomichi Okano, Masahiro Fukuda, Junko Tanabe, Masato Ono, Yasuhiro Akabane, Hisao Takahashi, Naoyuki Egawa, Takenobu Sakatani, Hirofumi Kanao, Yuji Yoneyama
  • Patent number: 5527949
    Abstract: A method for making an amine includes the steps of heating a reaction mixture including a nitrile, an acid, water and a substrate compound capable of generating a carbonium ion by reaction with the acid to generate a first reaction intermediate; treating the first reaction intermediate with an acid in the presence of a primary alkanol to form a second reaction intermediate and an alkyl ester; separating the alkyl ester from the second reaction intermediate; and treating the second reaction intermediate with a base to form the amine.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: June 18, 1996
    Assignee: Rohm and Haas Company
    Inventors: Sudhir K. Agarwal, Rajiv M. Banavali, Bharati D. Chheda, Samuel F. Reed, Jr.
  • Patent number: 5384426
    Abstract: Disclosed is an improved process for the refinement of isopropyl acetate, whereby there can be effectively prepared isopropyl acetate having a high purity of, for example, approximately 99.9%, in which a distillate fraction having a carbon number of 3 obtained by catalytically cracking petroleums such as naphtha or a crude propylene by-produced in a process for the preparation of isobutene by the dehydrogenation of isobutane.
    Type: Grant
    Filed: December 7, 1993
    Date of Patent: January 24, 1995
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kyuichi Ohyama, Giichi Shimada, Yuichi Tokumoto, Kazuo Sakamoto
  • Patent number: 5352812
    Abstract: The metathesis of functionalized and unfunctionalized acyclic olefins using catalyst compositions containing iridium and silver in a molar ration of 3 to 1.
    Type: Grant
    Filed: July 8, 1993
    Date of Patent: October 4, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Jerald Feldman, Marcia B. France
  • Patent number: 5241106
    Abstract: Ethyl acetate is produced in good yield by reacting ethylene with acetic acid in the presence of a catalyst comprising a tungstophosphoric acid of which 10-90% of the total amount of proton is replaced with a member selected from the group consisting of (a) cesium metal cation, (b) a combination of cesium metal cation and at least one cation selected from alkali metal cations other than cesium cation, and (c) a combination of cesium metal cation and at least one cation of iron group metal cations.
    Type: Grant
    Filed: October 19, 1992
    Date of Patent: August 31, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kaoru Inoue, Masao Iwasaki, Kazuaki Matsui
  • Patent number: 5235094
    Abstract: A halogenated ester is prepared by addition of a halogenated nucleophile to a diester at a temperature less than 15.degree. C. but greater than -25.degree. C.
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: August 10, 1993
    Assignee: The Dow Chemical Company
    Inventors: Kevin P. Darst, Marius W. Sorenson
  • Patent number: 5114624
    Abstract: In a process for the preparation of higher alkyl acrylic acid esters which comprises reacting one or more C.sub.10+ olefins with one or more alkyl acrylic acid esters in the presence of a halogen containing catalyst, the invention is the improvement which comprises contacting the reaction product mixture with an aqueous acid solution to extract catalyst residues therefrom and distilling the extracted product mixture to remove unreacted olefin.
    Type: Grant
    Filed: April 17, 1990
    Date of Patent: May 19, 1992
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried
  • Patent number: RE38864
    Abstract: Process for making a butyl ester from butadiene, comprising (a) reacting butadiene with a saturated aliphatic monocarboxylic acid to form a mixture of n-butenyl and secondary butenyl esters, (b) separating the n-butenyl ester from the secondary butenyl ester, and (c) hydrogenating the n-butenyl ester separated in step (b) in the presence of a catalyst to the corresponding n-butyl ester.
    Type: Grant
    Filed: September 29, 2004
    Date of Patent: November 1, 2005
    Assignee: The University of Southern Mississippi Research Foundation
    Inventors: Benjamin Patrick Gracey, Norbert Walter Josef Kamp
  • Patent number: RE41341
    Abstract: This invention relates to a process for the production of lower aliphatic esters by reacting a lower olefin with a saturated lower aliphatic mono-carboxylic acid in the vapor phase in the presence of a heteropolyacid catalyst characterized in that an amount of water in the range from 1-10 mole % based on the total of the olefin, aliphatic monocarboxylic acid and water is added to the reaction mixture during the reaction. The presence of water enhances the yield of the desired ester. The reaction mixture may optionally contain a di-ether to minimize the by-products. The process is particularly suitable for producing ethyl acetate from ethylene and acetic acid in the presence of water.
    Type: Grant
    Filed: February 28, 2007
    Date of Patent: May 18, 2010
    Assignee: Ineos Europe Limited
    Inventors: Martin P. Atkins, Bhushan Sharma