Preparing Esters From Hydrocarbons Patents (Class 560/241)
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Publication number: 20020049351Abstract: 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: ApplicationFiled: April 30, 2001Publication date: April 25, 2002Inventors: Benjamin Patrick Gracey, Norbert Walter Josef Kamp
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Patent number: 6376706Abstract: 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: GrantFiled: May 21, 1999Date of Patent: April 23, 2002Assignee: BP Chemical Ltd.Inventors: Simon James Kitchen, Daiyi Qin
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Publication number: 20020045778Abstract: 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: ApplicationFiled: July 18, 2001Publication date: April 18, 2002Inventors: Shun-Ichi Murahashi, Naruyoshi Komiya, Yukiko Hayashi
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Publication number: 20020028965Abstract: 1.Type: ApplicationFiled: November 2, 2001Publication date: March 7, 2002Applicant: BP Chemicals LimitedInventors: Simon Jobson, Derrick John Watson
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Publication number: 20020019562Abstract: 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: ApplicationFiled: December 21, 2000Publication date: February 14, 2002Inventors: Lance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
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Patent number: 6333430Abstract: 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: GrantFiled: May 2, 2000Date of Patent: December 25, 2001Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Shintaku, Kiyoshi Sugi, Tadashi Katsura, Nobushige Itaya
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Patent number: 6288269Abstract: 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: GrantFiled: December 16, 1999Date of Patent: September 11, 2001Assignee: BP Chemicals LimitedInventor: Derek Alan Colman
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Patent number: 6232491Abstract: 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: GrantFiled: April 26, 1999Date of Patent: May 15, 2001Assignee: BP Chemicals LimitedInventors: Malcolm J. Cunnington, Mohammed Hussain Khan, Witold Franciszek Pacynko
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Patent number: 6194602Abstract: 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: GrantFiled: April 16, 1998Date of Patent: February 27, 2001Assignee: ARCO Chemical Technology, L.P.Inventor: Lawrence J. Karas
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Patent number: 6118021Abstract: 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: GrantFiled: October 5, 1998Date of Patent: September 12, 2000Assignee: Membrane Technology and Research, Inc.Inventors: Douglas Gottschlich, Richard W. Baker
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Patent number: 6093857Abstract: 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: GrantFiled: September 12, 1997Date of Patent: July 25, 2000Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rolf Pinkos, Norbert Rieber, Michael Schulz, Joaquim Henrique Teles
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Patent number: 6013834Abstract: 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: GrantFiled: March 4, 1999Date of Patent: January 11, 2000Assignee: Celanese International CorporationInventor: Philip M. Colling
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Patent number: 5859287Abstract: 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: GrantFiled: October 30, 1997Date of Patent: January 12, 1999Assignee: Celanese International CorporationInventors: Ioan Nicolau, Philip M. Colling
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Patent number: 5476963Abstract: 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: GrantFiled: February 27, 1995Date of Patent: December 19, 1995Assignee: Hoechst AGInventors: Peter Wirtz, Friedrich Wunder, Karl-Fred Worner
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Patent number: 5457228Abstract: 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: GrantFiled: October 27, 1994Date of Patent: October 10, 1995Assignees: Daicel Chemical Industries, Ltd., Nippon Petrochemicals Company, LimitedInventors: Yuichi Tokumoto, Kazuo Sakamoto, Kikuo Sasaki, Isoo Shimizu
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Patent number: 5395960Abstract: 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: GrantFiled: April 28, 1994Date of Patent: March 7, 1995Assignee: BASF AktiengesellschaftInventors: Marc Heider, Thomas Ruehl, Jochem Henkelmann
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Patent number: 5258544Abstract: 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: GrantFiled: March 5, 1991Date of Patent: November 2, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Laurence W. Reilly, Jr., Ching T. Tsuei, Walter Rodriquez, Thomas Goetzen
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Patent number: 5254721Abstract: 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: GrantFiled: January 5, 1993Date of Patent: October 19, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Kaoru Inoue, Masao Iwasaki, Kazuaki Matsui
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Patent number: 5194676Abstract: 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: GrantFiled: March 26, 1991Date of Patent: March 16, 1993Assignee: AtochemInventors: Yves Castanet, Christophe Legrand, Andre Mortreux, Francis Petit
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Patent number: 5183931Abstract: 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: GrantFiled: February 10, 1992Date of Patent: February 2, 1993Assignee: Phillips Petroleum CompanyInventors: Chung C. Tso, Robert L. Wynn
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Patent number: 4900871Abstract: 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: GrantFiled: June 26, 1987Date of Patent: February 13, 1990Assignee: Sun Refining and Marketing CompanyInventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
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Patent number: 4895682Abstract: 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: GrantFiled: January 2, 1987Date of Patent: January 23, 1990Assignee: Sun Refining and Marketing CopanyInventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
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Patent number: 4895680Abstract: 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: GrantFiled: January 2, 1987Date of Patent: January 23, 1990Assignee: Sun Refining and Marketing CompanyInventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
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Patent number: 4736063Abstract: Butadiene and acetic acid are reacted with metal ion oxidant to prepare acetoxyhexenoic acids which are then converted to sorbic acid.Type: GrantFiled: January 2, 1981Date of Patent: April 5, 1988Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins
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Patent number: 4645863Abstract: 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: GrantFiled: January 12, 1983Date of Patent: February 24, 1987Assignee: BASF AktiengesellschaftInventors: Walter Rebafka, Helmut Nickels
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Patent number: 4612387Abstract: 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: GrantFiled: January 4, 1982Date of Patent: September 16, 1986Assignee: Air Products and Chemicals, Inc.Inventor: David Feitler
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Patent number: 4564689Abstract: 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: GrantFiled: June 13, 1983Date of Patent: January 14, 1986Assignee: Monsanto CompanyInventors: James P. Coleman, Dudley E. McMackins
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Patent number: 4560775Abstract: 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: GrantFiled: June 13, 1983Date of Patent: December 24, 1985Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins, Charles R. Penquite, Steven R. Auvil
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Patent number: 4526990Abstract: 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: GrantFiled: June 13, 1983Date of Patent: July 2, 1985Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher, Thomas E. Rogers, Dudley E. McMackins
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Patent number: 4508918Abstract: 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: GrantFiled: November 20, 1979Date of Patent: April 2, 1985Assignee: Toray Industries, Inc.Inventors: Yutaka Yasuhara, Masaki Nishino, Seikichi Matsuhisa
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Patent number: 4499298Abstract: 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: GrantFiled: December 20, 1979Date of Patent: February 12, 1985Assignee: National Distillers and Chemical CorporationInventors: John A. Scheben, James A. Hinnenkamp
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Patent number: 4460787Abstract: 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: GrantFiled: December 21, 1981Date of Patent: July 17, 1984Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher
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Patent number: 4450287Abstract: 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: GrantFiled: May 21, 1982Date of Patent: May 22, 1984Assignee: Shell Oil CompanyInventor: Timm E. Paxson
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Patent number: 4450288Abstract: 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: GrantFiled: May 21, 1982Date of Patent: May 22, 1984Assignee: Shell Oil CompanyInventor: Timm E. Paxson
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Patent number: 4450286Abstract: 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: GrantFiled: May 21, 1982Date of Patent: May 22, 1984Assignee: Shell Oil CompanyInventor: Timm E. Paxson
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Patent number: 4450289Abstract: 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: GrantFiled: May 21, 1982Date of Patent: May 22, 1984Assignee: Shell Oil CompanyInventor: Paxson, Timm E.
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Patent number: 4410461Abstract: 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: GrantFiled: September 18, 1981Date of Patent: October 18, 1983Assignee: Ashland Oil, Inc.Inventor: Peter E. Throckmorton
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Patent number: 4409396Abstract: 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: GrantFiled: September 3, 1981Date of Patent: October 11, 1983Assignees: Wacker-Chemie GmbH, Hoechst AktiengesellschaftInventors: Dominik Dempf, Ludwig Schmidhammer, Gerhard Dummer, Gunter Roscher, Karl-Heinz Schmidt, Ernst Selbertinger, Rudolf Strasser
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Patent number: 4365084Abstract: 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: GrantFiled: December 19, 1980Date of Patent: December 21, 1982Assignee: Mobil Oil CorporationInventor: Lewis B. Young
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Patent number: 4365083Abstract: 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: GrantFiled: December 19, 1980Date of Patent: December 21, 1982Assignee: Mobil Oil CorporationInventor: Lewis B. Young
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Patent number: 4356317Abstract: 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: GrantFiled: January 2, 1981Date of Patent: October 26, 1982Assignee: Monsanto CompanyInventors: James P. Coleman, Richard C. Hallcher, Dudley E. McMackins
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Patent number: 4323698Abstract: 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: GrantFiled: January 21, 1980Date of Patent: April 6, 1982Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4277633Abstract: 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: GrantFiled: July 12, 1979Date of Patent: July 7, 1981Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
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Patent number: 4263448Abstract: 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: GrantFiled: March 30, 1979Date of Patent: April 21, 1981Assignee: Halcon Research and Development Corp.Inventor: James Leacock
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Patent number: 4260808Abstract: 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: GrantFiled: November 3, 1978Date of Patent: April 7, 1981Assignee: Suntech, Inc.Inventors: James E. Lyons, George Suld, Robert W. Shinn
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Patent number: 4250330Abstract: 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: GrantFiled: January 30, 1980Date of Patent: February 10, 1981Assignee: Montedison S.p.A.Inventors: Giuseppe Costantini, Mauro Serafini, Pietro Paoli
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Patent number: 4237310Abstract: 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: GrantFiled: November 3, 1978Date of Patent: December 2, 1980Assignee: Suntech, Inc.Inventors: George Suld, James E. Lyons, Robert W. Shinn
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Patent number: 4233230Abstract: 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: GrantFiled: May 4, 1978Date of Patent: November 11, 1980Assignee: Rhone-Poulenc IndustriesInventor: Jean Otton
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Patent number: 4229587Abstract: 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: GrantFiled: December 26, 1978Date of Patent: October 21, 1980Assignee: National Distillers and Chemical CorporationInventor: Jawad H. Murib
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Patent number: 4225728Abstract: 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: GrantFiled: November 3, 1978Date of Patent: September 30, 1980Assignee: Suntech, Inc.Inventors: James E. Lyons, George Suld, Robert W. Shinn