Preparing Esters From Hydrocarbons Patents (Class 560/241)
  • Publication number: 20020049351
    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: Application
    Filed: April 30, 2001
    Publication date: April 25, 2002
    Inventors: Benjamin Patrick Gracey, Norbert Walter Josef Kamp
  • Patent number: 6376706
    Abstract: A catalyst for use in the production of vinyl acetate which comprises (1) a catalyst support, (2) palladium, (3) an acid, (4) at least one acetic acid catalyst promoter and (5) at least one vinyl acetate promoter and/or co-promoter. A process for the production of vinyl acetate from ethylene and an oxygen-containing gas using the catalyst.
    Type: Grant
    Filed: May 21, 1999
    Date of Patent: April 23, 2002
    Assignee: BP Chemical Ltd.
    Inventors: Simon James Kitchen, Daiyi Qin
  • Publication number: 20020045778
    Abstract: A method for oxidizing an alkane, comprising the step of oxidizing said alkane with oxygen in the presence of an aldehyde, a copper-based catalyst and a nitrogen-containing compound. This method may be used to convert alkanes to corresponding alcohols and ketone having pharmaceutical activities, etc.
    Type: Application
    Filed: July 18, 2001
    Publication date: April 18, 2002
    Inventors: Shun-Ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
  • 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
  • Publication number: 20020019562
    Abstract: Long chain alcohols and acids or other similar oxygenates such as esters are produced from paraffins of similar carbon number by a process comprising paraffin dehydrogenation, carbonylation, and separation. Preferably a mixture of paraffins extending over several carbon numbers and recovered from a kerosene fraction is processed, and unconverted paraffins are recycled to a dehydrogenation zone. Alternative reaction zone configurations, catalyst systems and product recovery methods are disclosed.
    Type: Application
    Filed: December 21, 2000
    Publication date: February 14, 2002
    Inventors: Lance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
  • 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
  • Patent number: 6288269
    Abstract: Apparatus for introducing a fluid into a process stream such as promoter into the feed stream of a reactor for manufacturing vinyl acetate comprises: (a) a process stream pipe having a bend and (b) a nozzle for introducing the fluid into the process stream downstream of the bend characterised in that the pipe has a flow-correction device downstream of the bend and the nozzle is mounted downstream of the flow-correction device to an end of a support arm which extends into the pipe in a direction substantially parallel to the direction of the pipe downstream of the bend.
    Type: Grant
    Filed: December 16, 1999
    Date of Patent: September 11, 2001
    Assignee: BP Chemicals Limited
    Inventor: Derek Alan Colman
  • Patent number: 6232491
    Abstract: This invention is a process for the removal of acetaldehyde impurities from ethyl acetate formed by reacting acetic acid with ethylene over a catalyst by refining a crude mixture of ethyl acetate, diethyl ether, acetaldehye and water in a column (C) so as to remove (a) refined ethyl acetate as a base product to be further purified, and (b) light ends mixture comprising diethyl ether and acetaldehyde overhead to be fed to an aldehyde removal column; a purge comprising acetaldehyde is removed at or near the top of the aldehyde removal column. The process is a very important step in the commercial manufacture of ethyl acetate because the presence of acetaldehyde is detrimental to the esterification catalyst.
    Type: Grant
    Filed: April 26, 1999
    Date of Patent: May 15, 2001
    Assignee: BP Chemicals Limited
    Inventors: Malcolm J. Cunnington, Mohammed Hussain Khan, Witold Franciszek Pacynko
  • 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: 6118021
    Abstract: A process and apparatus for vinyl acetate production. A membrane unit containing a membrane selectively permeable to ethylene over argon is used to recover ethylene from the argon purge stream.
    Type: Grant
    Filed: October 5, 1998
    Date of Patent: September 12, 2000
    Assignee: Membrane Technology and Research, Inc.
    Inventors: Douglas Gottschlich, Richard W. Baker
  • Patent number: 6093857
    Abstract: A process for preparing cyclopentyl formates of the formula (II) ##STR1## by reacting cyclopentenes of the formula (I) ##STR2## where R.sup.1, R.sup.2 and R.sup.3, independently of one another, are hydrogen atoms or C.sub.1-8 -alkyl,with formic acid in the presence of an acid catalyst.
    Type: Grant
    Filed: September 12, 1997
    Date of Patent: July 25, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Rolf Pinkos, Norbert Rieber, Michael Schulz, Joaquim Henrique Teles
  • Patent number: 6013834
    Abstract: A process for the production of vinyl acetate (VA) by reaction in the vapor phase of ethylene, oxygen and acetic acid as reactants, comprising passing at a temperature sufficient to initiate the reaction, a feed gas comprising said reactants and continuously or intermittently containing liquid acetic acid and/or non-volatile components, through a filter and distribution bed of inert material having throughout its volume substantial intercommunicating open spaces among the solid portions, and thence through a plurality of tubes each containing a bed of catalyst for the reaction, and withdrawing a product gas comprising VA. The filter and distribution bed acts to filter out the liquid acetic acid and/or non-volatile components and distribute more evenly the feed gas into the tubes.
    Type: Grant
    Filed: March 4, 1999
    Date of Patent: January 11, 2000
    Assignee: Celanese International Corporation
    Inventor: Philip M. Colling
  • Patent number: 5859287
    Abstract: A catalyst for the production of vinyl acetate by reaction of ethylene, oxygen and acetic acid as reactants comprising a porous support on the porous surfaces of which is deposited catalytically effective amounts of metallic palladium and gold and a third metal selected from the group consisting of magnesium calcium, barium, zirconium and cerium, as its oxide or mixture of oxide and metal, said catalyst having been prepared by either of two specified methods (A) or (B). Use of the catalyst results in a reaction of relatively high activity and/or low heavy ends selectivity.
    Type: Grant
    Filed: October 30, 1997
    Date of Patent: January 12, 1999
    Assignee: Celanese International Corporation
    Inventors: Ioan Nicolau, Philip M. Colling
  • Patent number: 5476963
    Abstract: Supported catalyst, process for its preparation and its use for the preparation of vinyl acetateThe invention relates to improved Pd/K/Au, Pd/K/Ba and Pd/K/Cd supported catalysts, their preparation and their use for the preparation of vinyl acetate from ethylene, acetic acid and oxygen in the gas phase. The stated catalysts are prepared by atomizing a solution of corresponding metal salts by means of ultrasonics and then applying them in such limited amounts and within such a limited time to the carrier particles, and beginning to dry them, so that the catalytically active metal salts cannot penetrate into the carrier particles as far as the core but only into a larger or smaller outer part.
    Type: Grant
    Filed: February 27, 1995
    Date of Patent: December 19, 1995
    Assignee: Hoechst AG
    Inventors: Peter Wirtz, Friedrich Wunder, Karl-Fred Worner
  • Patent number: 5457228
    Abstract: A method for producing a lower alkyl acetate in which undesirable polymerization of the starting material of olefin and deterioration of catalyst can be avoided, a higher catalytic efficiency and a higher reaction rate are attained, the installation of reaction equipment is inexpensive and the operation of the reaction can be carried out without difficulty. The method of the invention comprises the steps of feeding acetic acid and an olefin both in a liquid state and in cocurrent through a continuous flow type fixed bed reactor containing an acidic ion exchange resin catalyst(s) under the conditions that the molar ratio of acetic acid to the olefin in a feed current is in the range of 1.0 to 2.0 and an LHSV of acetic acid relative to the catalyst layer is 0.1 to 10.0 with maintaining the inlet of the catalyst bed at 70.degree. C. to 120.degree. C.; cooling the obtained reaction mixture to a temperature not lower than 70.degree. C.; and recycling it to the catalyst bed.
    Type: Grant
    Filed: October 27, 1994
    Date of Patent: October 10, 1995
    Assignees: Daicel Chemical Industries, Ltd., Nippon Petrochemicals Company, Limited
    Inventors: Yuichi Tokumoto, Kazuo Sakamoto, Kikuo Sasaki, Isoo Shimizu
  • Patent number: 5395960
    Abstract: Preparation of vinyl carboxylates by the reaction of a carboxylic acid with acetylene in the presence of a platinum metal complex catalyst, which contains as ligands carbon monoxide or a nitrile (I), a tertiary nitrogen base (II), a tertiary phosphorus compound (III) having C-organic and/or O-organic radicals or mixtures of said compounds.The end products serve as monomers or comonomers for polymer dispersions.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: March 7, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Marc Heider, Thomas Ruehl, Jochem Henkelmann
  • Patent number: 5258544
    Abstract: Disclosed is a process for the preparation of 2-aryl-1-cyclohexene-1-carboxaldehydes from 1-arylcyclohexenes which are intermediates for trans-6-[(2-arylsubstituted cycloalkenyl and substituted cycloalkyl)alkenyl and alkyl]-3,4,5,6-tetrahydro-2H-pyran-2-ones.
    Type: Grant
    Filed: March 5, 1991
    Date of Patent: November 2, 1993
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Laurence W. Reilly, Jr., Ching T. Tsuei, Walter Rodriquez, Thomas Goetzen
  • Patent number: 5254721
    Abstract: Cyclohexyl acetate is produced by reacting acetic acid with cyclohexene in the presence of a heteropolyacid mainly composed of oxides of tungsten as a catalyst. The heteropolyacid may have water of crystallization adjusted to the amount of average 3.0 molecules or less per one molecule of the heteropolyacid. Cyclohexyl acetate can be produced in high selectivity and high conversion. The catalyst is effective even at a low temperature and stable even at a high temperature.
    Type: Grant
    Filed: January 5, 1993
    Date of Patent: October 19, 1993
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Kaoru Inoue, Masao Iwasaki, Kazuaki Matsui
  • Patent number: 5194676
    Abstract: Saturated carboxylic esters are produced from alkyl formate and an olefin, without the presence of substantial amounts of carbon monoxide, at a temperature of 120.degree. to 280.degree. C., under a pressure of 1 to 3,000 bars, in the presence of a catalyst based on ruthenium coordinated by ligands selected from carbon monoxide, halogen atoms and amines, and in the presence of an amide as a solvent. The catalyst is selected from catalysts consisting essentially of RuCl.sub.3.3H.sub.2 O; catalysts consisting essentially of the combination of an RuCl.sub.3.3H.sub.2 O together with at least one stabilizer selected from iodine, covalent iodides and quaternary ammonium halides; catalysts comprising Ru.sub.3 (CO).sub.12 together with at least one stabilizer such as is mentioned above; and catalysts selected from RuI.sub.3, [RuCl.sub.2 (CO).sub.3 ].sub.2, Ru(NH.sub.3).sub.6 Cl.sub.3 and [Ru(NH.sub.3).sub.5 Cl]Cl.sub.2, comprising, where appropriate, in addition, at least one stabilizer such as is mentioned above.
    Type: Grant
    Filed: March 26, 1991
    Date of Patent: March 16, 1993
    Assignee: Atochem
    Inventors: Yves Castanet, Christophe Legrand, Andre Mortreux, Francis Petit
  • Patent number: 5183931
    Abstract: Oxidation of alkylaromatics having a benzylic hydrogen atom is catalyzed by a catalyst comprising a palladium salt, a metal persulfate, a third metal salt, and a tin salt in a carboxylic acid for a period of time sufficient to convert the alkylaromatics to their corresponding oxidized derivatives. The catalyst is prepared by preheating the palladium salt and the metal persulfate at a temperature sufficient to provide the desired catalytic activity followed by additon of the third metal salt and the tin salt.
    Type: Grant
    Filed: February 10, 1992
    Date of Patent: February 2, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Chung C. Tso, Robert L. Wynn
  • Patent number: 4900871
    Abstract: Hydrocarbons, and particularly lower molecular weight alkanes and cycloalkanes, may readily be oxidized with air or O.sub.2 to form such products as alcohols, ketones, and the like selectively high yields when there is employed as the catalyst a coordination complex containing an iron center and a halogenated ligand having the structure ##STR1## where Fe is iron; " .circle. " is a ligand; X is a halogen substituent of the ligand; and A is an anion.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: February 13, 1990
    Assignee: Sun Refining and Marketing Company
    Inventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
  • Patent number: 4895680
    Abstract: Hydrocarbon, and particularly lower molecular weight alkanes and cycloalkanes, may readily be oxidized with air or O.sub.2 to form such products as alcohols, ketones, and the like in high yields when there is employed as the catalyst a highly active nitride-activated metal coordination complex having the structure ##STR1## where M is a transition metal; " " is a ligand; and X is a nitride. Certain dimeric forms of the above catalyst are also employed herein. It has also been discovered that Group IV through VIII transition metal nitrides are also highly effective oxidation catalysts for lower molecular weight hydrocarbons such as alkanes.
    Type: Grant
    Filed: January 2, 1987
    Date of Patent: January 23, 1990
    Assignee: Sun Refining and Marketing Company
    Inventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
  • Patent number: 4895682
    Abstract: Hydrocarbons, and particularly lower molecular weight alkanes and cycloalkanes, may readily be oxidixed with air or O.sub.2 to form such products as alcohols, ketones, and the like selectively in high yields when there is employed as the catalyst a highly active azide-activated metal coordination complex having the structure ##STR1## where M is a transition metal; " " is a ligand; and X is azide. The invention is also directed to certain novel azide-activated metal coordination complex catalysts per se.
    Type: Grant
    Filed: January 2, 1987
    Date of Patent: January 23, 1990
    Assignee: Sun Refining and Marketing Copany
    Inventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
  • Patent number: 4736063
    Abstract: Butadiene and acetic acid are reacted with metal ion oxidant to prepare acetoxyhexenoic acids which are then converted to sorbic acid.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: April 5, 1988
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins
  • Patent number: 4645863
    Abstract: Process for the preparation of unsaturated alcohols and/or esters thereof by reacting conjugated dienes with water and/or aqueous carboxylic acid solutions in the presence of a macroporous acid ion exchanger and suitable solvents. The diene has the general formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are hydrogen or a methyl group and R.sup.2 also can represent an aliphatic hydrocarbon radical having 2 to 6 carbon atoms which may contain a double bond which is not in a conjugated position relative to the double bonds of the diene, and preferably R.sup.1 and R.sup.3 each represent groups CH.sub.3 or CH.sub.2 --CH.sub.3. Said diene is reacted in a homogeneous or quasi-homogeneous phase in the presence of said macroporous acid ion exchanger.
    Type: Grant
    Filed: January 12, 1983
    Date of Patent: February 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Rebafka, Helmut Nickels
  • Patent number: 4612387
    Abstract: A method for making monocarboxylic acids and esters comprising contacting carbon monoxide and a monohydric alcohol containing 1 to 4 carbon atoms in the presence of a crystalline aluminosilicate zeolite having a silica to alumina ratio at least about 6 and a constraint index within the approximate range of 1 to 12 under a pressure of at least one atmosphere. Also coproduced are hydrocarbons, particularly ethylene and "gasoline".
    Type: Grant
    Filed: January 4, 1982
    Date of Patent: September 16, 1986
    Assignee: Air Products and Chemicals, Inc.
    Inventor: David Feitler
  • Patent number: 4564689
    Abstract: In processes for reacting acetic acid with butadiene in solvent to prepare acetoxyhexenoic acid and .gamma.-vinyl-.gamma.-butyrolactone, involving electrolytic regeneration of a metal ion oxidant such as trivalent manganese, the product separation is facilitated by using low melting electrolyte salts and separating product from salts maintained in a molten state.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: January 14, 1986
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Dudley E. McMackins
  • Patent number: 4560775
    Abstract: Butadiene and acetic acid are reacted with a metal salt oxidant in molten salt medium to form .gamma.-vinyl-.gamma.-butyrolactone. The process includes electrolytic regeneration of the oxidant and provides a simple reaction system which permits product recovery and reactant recycle without extensive solvent handling. A high surface area reactor can be employed.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: December 24, 1985
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins, Charles R. Penquite, Steven R. Auvil
  • Patent number: 4526990
    Abstract: In the process of preparing acetoxyhexenoic acids from butadiene, acetic acid and acetic anhydride, selectivity is improved by converting the acetoxyhexenoic acids to .gamma.-vinyl-.gamma.-butyrolactone before isolation. Copper and platinum are useful catalysts in the conversion.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: July 2, 1985
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Thomas E. Rogers, Dudley E. McMackins
  • Patent number: 4508918
    Abstract: Cyclohexane derivatives such as cyclohexanol and cyclohexyl carboxylates are produced directly from aromatic hydrocarbons. The reaction may be carried out, under hydrogenation conditions, by reacting an aromatic hydrocarbon with hydrogen and a reagent selected from the group consisting of water, and carboxylic acids in the presence of a strong acid and a hydrogenation catalyst.
    Type: Grant
    Filed: November 20, 1979
    Date of Patent: April 2, 1985
    Assignee: Toray Industries, Inc.
    Inventors: Yutaka Yasuhara, Masaki Nishino, Seikichi Matsuhisa
  • Patent number: 4499298
    Abstract: A process is described for the preparation of aryl esters such as benzyl acetate by reacting an aryl alkyl compound such as toluene with a carboxylic acid such as acetic acid and oxygen in the presence of a catalytically effective amount of a catalyst comprising palladium metal, gold metal and a metal of Group VA of the Periodic Table of the Elements such as bismuth.
    Type: Grant
    Filed: December 20, 1979
    Date of Patent: February 12, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventors: John A. Scheben, James A. Hinnenkamp
  • Patent number: 4460787
    Abstract: The acid conversion of certain precursors, e.g. .gamma.-vinyl-.gamma.-butyrolactone, to sorbic acid is improved by presence of copper or silver ions along with the acid.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: July 17, 1984
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher
  • Patent number: 4450288
    Abstract: A process for producing butenyl acetate which comprises reacting butadiene and acetic acid in the presence of a catalyst comprising a sulfonic acid ion exchange resin modified with an alkyl pyridinium salt.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: May 22, 1984
    Assignee: Shell Oil Company
    Inventor: Timm E. Paxson
  • Patent number: 4450286
    Abstract: A process for producing butenyl acetate which comprises reacting butadiene and acetic acid in the presence of a catalyst comprising a sulfonic acid ion exchange resin modified with a quaternary ammonium and/or phosphonium substituted ferrocenyl salt.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: May 22, 1984
    Assignee: Shell Oil Company
    Inventor: Timm E. Paxson
  • Patent number: 4450289
    Abstract: A process for producing butenyl acetate which comprises reacting butadiene and acetic acid in the presence of a catalyst comprising a sulfonic acid ion exchange resin modified with a quaternary phosphonium salt.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: May 22, 1984
    Assignee: Shell Oil Company
    Inventor: Paxson, Timm E.
  • Patent number: 4450287
    Abstract: A process for producing butenyl acetate which comprises reacting butadiene and acetic acid in the presence of a catalyst comprising a sulfonic acid ion exchange resin modified with a quaternary ammonium salt.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: May 22, 1984
    Assignee: Shell Oil Company
    Inventor: Timm E. Paxson
  • Patent number: 4410461
    Abstract: A catalytic homogeneous liquid phase process for effecting the acyloxylation of toluene to produce the corresponding benzylic ester. The catalyst system comprises Pd(II) and Pb(II) values wherein the palladous element component is associated with a catalytic amount of a tertiary phosphine as a complexed ligand. The indicated catalyst system uniquely facilitates the advantageous use of normally immiscible carboxylic acid reactants for carrying out the underlying benzylic oxidation reaction.
    Type: Grant
    Filed: September 18, 1981
    Date of Patent: October 18, 1983
    Assignee: Ashland Oil, Inc.
    Inventor: Peter E. Throckmorton
  • Patent number: 4409396
    Abstract: The invention relates to a process for the manufacture of unsaturated carboxylic acid esters by the reaction of olefins or cyclo-olefins with oxygen and carboxylic acids in the gaseous phase, in the presence of a catalyst which contains elements of the subsidiary group VIII of the periodic system and/or compounds thereof, and an alkali metal acetate, at temperatures of from 100.degree. to 250.degree. C. and pressures of from 0.5 to 21 bar absolute, wherein from 1 to 8000 parts per million (by weight), calculated on the carboxylic acid used, of organic chlorine compounds are added to the reaction mixture.
    Type: Grant
    Filed: September 3, 1981
    Date of Patent: October 11, 1983
    Assignees: Wacker-Chemie GmbH, Hoechst Aktiengesellschaft
    Inventors: Dominik Dempf, Ludwig Schmidhammer, Gerhard Dummer, Gunter Roscher, Karl-Heinz Schmidt, Ernst Selbertinger, Rudolf Strasser
  • Patent number: 4365084
    Abstract: A method for preparation of alkyl carboxylate compounds, and especially .alpha.-methylalkyl carboxylate compounds, by reaction of an olefin and a carboxylic acid compound in the presence of a particular type of zeolite catalyst. The zeolites are characterized by a silica to alumina mole ratio of at least 12 and a constraint index of 1 to 12. Zeolites ZSM-5 and ZSM-12 are particularly preferred.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: December 21, 1982
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4365083
    Abstract: A method for preparation of alkyl carboxylate compounds, and especially methylalkyl carboxylate compounds, by reaction of an olefin and a carboxylic acid compound in the presence of a mordenite catalyst.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: December 21, 1982
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4356317
    Abstract: Acyloxyhexenoic acids are produced by reaction of butadiene and acetic acid with metal salt oxidants in a process involving electrolytic regeneration of the metal oxidants during the reaction.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: October 26, 1982
    Assignee: Monsanto Company
    Inventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins
  • Patent number: 4323698
    Abstract: This specification discloses an insoluble resin-metal compound complex, the method for its preparation, and its use in carrying out a catalyzed reaction. The complex is a weak base anion exchange resin which has been contacted with a solution of a coordination compound having at least two ligands connected to at least one central metal atom to bond chemically the resin to the metal atom by replacement of at least one of the ligands of the coordination compound by a functional group of the weak base anion exchange resin. The complex can be used as a catalyst for hydrogenation, carbon monoxide insertion, polymerization, isomerization, vinyl ester exchange, and ethylene oxidation reactions, among others.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: April 6, 1982
    Assignee: Mobil Oil Corporation
    Inventors: Werner O. Haag, Darrell D. Whitehurst
  • Patent number: 4277633
    Abstract: The palladium complex disclosed herein is bis[tri(ortho-tolyl)phosphine] :palladium which is produced by reacting a palladium salt with tri(ortho-tolyl)phosphine and reducing the resultant bis[tri(ortho-tolyl)phosphine] palladium salt with an alcoholic alkali. This complex is useful as a catalyst for the production of 1,3-diene oligomers.
    Type: Grant
    Filed: July 12, 1979
    Date of Patent: July 7, 1981
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
  • Patent number: 4263448
    Abstract: An oxidizable hydrocarbon is oxidized in a reaction zone at elevated temperature in the presence of a liquid reaction medium by introducing the hydrocarbon and a feed stream containing molecular oxygen to the reaction zone under conditions sufficient to oxidize at least a portion of the hydrocarbon; withdrawing at least a portion of the liquid reaction medium from the reaction zone; passing at least a portion of the withdrawn liquid reaction medium to an oxygen injection zone located external to the reaction zone; contacting the liquid in said oxygen-injection zone with a gas stream containing molecular oxygen under conditions sufficient to form a two-phase gas/liquid mixture; and passing said two-phase gas/liquid mixture to the reaction zone as the feed of molecular oxygen thereto.
    Type: Grant
    Filed: March 30, 1979
    Date of Patent: April 21, 1981
    Assignee: Halcon Research and Development Corp.
    Inventor: James Leacock
  • Patent number: 4260808
    Abstract: Equimolar amounts of phenol and formaldehyde may be prepared from oxygen and toluene. The catalytic oxidation of toluene, when carried out in the presence of acetic anhydride, forms phenyl acetate and methylene diacetate. Pyrolysis of these two intermediates yields phenol and formaldehyde.Significant improvements in this process are achieved when the first stage of the reaction is carried out in the presence of MoO.sub.3.In a further embodiment of this invention it has been found that Group VIII dithiosemibenzil compounds, particularly nickel dithiosemibenzil, serves as a superior promoter for the toluene oxidation reaction.In still a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for the toluene oxidation reaction.In a like manner, hydroquinone or resorcinol may be obtained from cresyl acetates.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: April 7, 1981
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, George Suld, Robert W. Shinn
  • Patent number: 4250330
    Abstract: The invention refers to an improved process for the recovery of the solvent and of the by-produced methylacetate in the synthesis of terephthalic acid, said synthesis being usually consisting of an oxidation of paraxylene with air, in the presence of a catalyst system composed by cobalt, manganese and bromine, in a solvent consisting of acetic acid, according to the equation (1):C.sub.6 H.sub.4 (CH.sub.3).sub.2 +3 O.sub.2 .fwdarw.C.sub.6 H.sub.4 (COOH).sub.2 =2 H.sub.
    Type: Grant
    Filed: January 30, 1980
    Date of Patent: February 10, 1981
    Assignee: Montedison S.p.A.
    Inventors: Giuseppe Costantini, Mauro Serafini, Pietro Paoli
  • Patent number: 4237310
    Abstract: The oxidation of methyl benzenes, such as toluene, with air or oxygen in the presence of acetic anhydride and sulfuric acid catalyst to form a phenolic acetate and methylene diacetate may be carried out under mild conditions when small amounts of benzaldehyde are added to the reaction.The resulting acetates may then be pyrolyzed to yield phenolic compounds and formaldehyde, respectively.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: December 2, 1980
    Assignee: Suntech, Inc.
    Inventors: George Suld, James E. Lyons, Robert W. Shinn
  • Patent number: 4233230
    Abstract: A process for preparing esters and halides is disclosed comprising the step of reacting a cyclic olefin having the formula I ##STR1## wherein R.sub.1 and R.sub.4 are the same or different from each other and each represents hydrogen, methyl, or ethyl;R.sub.2 and R.sub.3 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms; andn represents a whole number from 2 to 12, with an acyclic olefin having the formula II ##STR2## wherein R.sub.5 represents hydrogen, methyl, ethyl or the group ##STR3## wherein R.sub.12 and R.sub.13 are the same or different from each other and each represents hydrogen or alkyl containing 1 to 5 carbon atoms;Y represents halogen; an acyloxy group R.sub.14 --CO--O wherein R.sub.14 represents alkyl containing 1-12 carbon atoms, phenyl or phenyl alkyl containing 7-12 carbon atoms, or an oxycarbonyl group R.sub.15 --O--CO wherein R.sub.
    Type: Grant
    Filed: May 4, 1978
    Date of Patent: November 11, 1980
    Assignee: Rhone-Poulenc Industries
    Inventor: Jean Otton
  • Patent number: 4229587
    Abstract: A process for preparing aromatic esters by oxyacylation which comprises contacting benzene or an aryl alkyl compound with a carboxylic acid and oxygen in the vapor phase in the presence of a catalytically effective amount of a catalyst comprising an oxide of uranium and at least one oxide selected from the group consisting of arsenic, antimony and bismuth oxide.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: October 21, 1980
    Assignee: National Distillers and Chemical Corporation
    Inventor: Jawad H. Murib
  • Patent number: 4225728
    Abstract: Equimolar amounts of vinyl acetate and phenol may be prepared by oxidation of ethyl benzene. The catalytic oxidation, of ethyl benzene, when carried out in the presence of acetic anhydride, forms phenyl acetate and ethylidene diacetate. Pyrolysis of these two intermediates yields vinyl acetate and phenol.In a further embodiment of this invention it has been found that persulfate promoters such as potassium persulfate, persulfuric acid, or Caro's dry acid are particularly effective promoters for this oxidation reaction.
    Type: Grant
    Filed: November 3, 1978
    Date of Patent: September 30, 1980
    Assignee: Suntech, Inc.
    Inventors: James E. Lyons, George Suld, Robert W. Shinn