Of Hydrocarbon Patents (Class 562/521)
  • Patent number: 12060311
    Abstract: The present invention can provide a method for producing an aromatic nitrile in which a fixed-bed reactor including a plurality of reaction tubes is used to subject a gaseous mixture comprising an aromatic hydrocarbon, ammonia, and oxygen by contact catalytic reaction on a catalyst to thereby produce the corresponding aromatic nitrile, wherein the catalyst is composed of an oxide containing vanadium, chromium, and boron and one or more supports selected from among alumina, silica-alumina, zirconia, and titania. One of the reaction tubes is filled with the catalyst of one kind and examined as to where a hot spot lies therein. An inert substance is filled into that portion of each of the plurality of reaction tubes which corresponds at least to the hot spot, and the catalyst is filled into the remaining portions.
    Type: Grant
    Filed: March 18, 2019
    Date of Patent: August 13, 2024
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yutaka Kanbara, Yuta Oomori, Yoichi Kyuuko, Tomoo Tsujimoto, Kazunari Yamamoto, Tsuyoshi Hatakeyama
  • Patent number: 9822197
    Abstract: A process for producing water-absorbing polymer particles, comprising the steps of thermal cracking of bionaphtha in the presence of steam, removing propene and at least some of the propane, gas phase oxidation to give acrylic acid and polymerization to give water-absorbing polymer particles.
    Type: Grant
    Filed: November 18, 2013
    Date of Patent: November 21, 2017
    Assignee: BASF SE
    Inventors: Klaus Dieter Hörner, Jürgen Schröder, Rüdiger Funk, Renate Wüstefeld
  • Patent number: 9174915
    Abstract: The disclosure relates to processes and systems utilizing one or more extraction towers in the recovery and recycle of acid catalysts used in the production of carboxylic acids. The carboxylic acids may be neo-acids produced through the hydrocarboxylation of olefins or olefin mixtures.
    Type: Grant
    Filed: May 4, 2011
    Date of Patent: November 3, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventor: Carl R. Beck
  • Publication number: 20150057458
    Abstract: Process for the production of a chemical compound from a carbon dioxide starting material, comprising the steps of a) providing a feed stream consisting mainly of carbon dioxide; b) electrolysing in an electrolysis stage the carbon dioxide in the feed stream to a first gas stream containing carbon monoxide and a second gas stream containing oxygen, wherein the molar ratio between carbon monoxide and oxygen is about 1:0.5 in an electrolysis stage; c) adjusting the composition of the first gas stream or the second gas stream or both gas streams to include carbon dioxide, either by operating at less than full conversion of CO2 or by sweeping one or both gas streams with a gas containing CO2 or by at some stage between the electrolysis cell and the oxidative carbonylation reactor diluting one or both gas streams with a gas containing CO2; all while maintaining an overall molar ratio of carbon monoxide to oxygen of about 1:0.
    Type: Application
    Filed: April 11, 2013
    Publication date: February 26, 2015
    Applicant: Haldor Topsøe A/S
    Inventors: Niels Christian Schjødt, John Bøgild Hansen, Claus Friis Pedersen
  • Patent number: 8642803
    Abstract: A process for preparing an alkali metal or alkaline earth metal salt of an ?,?-ethylenically unsaturated carboxylic acid, wherein a) an alkene, carbon dioxide and a carboxylation catalyst are converted to an alkene/carbon dioxide/carboxylation catalyst adduct, b) the adduct is decomposed to release the carboxylation catalyst with an auxiliary base to give the auxiliary base salt of the ?,?-ethylenically unsaturated carboxylic acid, c) the auxiliary base salt of the ?,?-ethylenically unsaturated carboxylic acid is reacted to release the auxiliary base with an alkali metal or alkaline earth metal base to give the alkali metal or alkaline earth metal salt of the ?,?-ethylenically unsaturated carboxylic acid. Salts of ?,?-ethylenically unsaturated carboxylic acids, such as sodium acrylate in particular, are required in large amounts, for example, for production of water-absorbing resins.
    Type: Grant
    Filed: March 3, 2011
    Date of Patent: February 4, 2014
    Assignee: BASF SE
    Inventors: Michael Limbach, Jeremie Miller, Stephan Schunk
  • Publication number: 20140031583
    Abstract: This invention relates to improvements in the fast pyrolysis of biomass. In this invention, olefins are separated from the effluent stream of a pyrolysis reactor and at least a portion of the olefins are treated and the resulting treated stream recycled to the pyrolysis reactor for further conversion to valuable, useful products.
    Type: Application
    Filed: July 29, 2013
    Publication date: January 30, 2014
    Inventors: Terry Mazanec, Jeff Whiting, Fred Pesa, Greg Norenberg
  • Patent number: 8058472
    Abstract: The present invention concerns a new efficient method for the selective transformation, under mild conditions and in aqueous medium, of gaseous (ethane, propane and n-butane) and liquid (n-pentane, n-hexane, cyclopentane and cyclohexane) alkanes into carboxylic acids bearing one more carbon atom, characterized by a single-pot low-temperature (25-60° C.) reaction of the alkane with carbon monoxide in water/acetonitrile liquid medium, either in the absence or in the presence of a metal catalyst, in systems containing also an oxidant (a peroxodisulphate salt).
    Type: Grant
    Filed: January 17, 2008
    Date of Patent: November 15, 2011
    Assignee: Instituto Superior Tecnico
    Inventors: Armando Pombeiro, Marina Kirillova, Alexander Kirillov, Jose Armando Silva, Joao Frausto Da Silva
  • Patent number: 7629491
    Abstract: Disclosed is a hydrocarboxylation process for the production of carboxylic acid from olefins wherein an olefin, water, a Group VIII metal hydrocarboxylation catalyst, an onium salt compound are combined in a reaction zone and contacted with carbon monoxide under hydrocarboxylation conditions of pressure and temperature The process does not require or utilize the addition of a hydrogen halide or an alkyl halide exogenous or extraneous to the hydrocarboxylation process.
    Type: Grant
    Filed: June 26, 2006
    Date of Patent: December 8, 2009
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Mary Kathleen Moore
  • Publication number: 20090131630
    Abstract: A process for the preparation of a dicarboxylic acid, comprising the steps of (a) contacting a conjugated diene with carbon monoxide and water in the presence of a catalyst system including a source of palladium, a source of an anion and a bidentate phosphine ligand, to obtain a mixture containing an ethylenically unsaturated acid and one or more reversible adduct of the conjugated diene and the ethylenically unsaturated acid; and (b) removing unreacted conjugated diene, and the reversible adducts of the conjugated diene from the reaction mixture; and (c) reacting the mixture obtained in step (b) containing the ethylenically unsaturated acid further with carbon monoxide and water to obtain the dicarboxylic acid.
    Type: Application
    Filed: February 10, 2006
    Publication date: May 21, 2009
    Inventors: Johannes Adrianus Maria Van Broekhoven, Eit Drent, Rene Ernst, Willem Wabe Jager, Cornelia Alida Krom
  • Publication number: 20080300414
    Abstract: A process for recharging the reaction tubes of a tube bundle reactor with a new fixed catalyst bed, in which a heterogeneously catalyzed partial gas phase oxidation of an organic compound had been performed beforehand in a preceding fixed catalyst bed comprising Mo-comprising multielement oxide active compositions to form a steam-comprising product gas mixture, in which, before the recharge, solid deposit which had been deposited on the tube inner walls and comprises molybdenum oxide and/or molybdenum oxide hydrate is brushed away with the aid of a brush.
    Type: Application
    Filed: May 30, 2008
    Publication date: December 4, 2008
    Applicant: BASF SE
    Inventors: Volker SCHLIEPHAKE, Klaus BOTT, Rolf-Dieter BECHER, Klaus Joachim MULLER-ENGEL, Jochen PETZOLDT, Ulrich CREMER, Andreas RAICHLE
  • Patent number: 7449597
    Abstract: A catalyst useful for carbonylation of olefins has been developed. The catalyst comprises a palladium compound, e.g. PdIm4Cl2, where Im is imidazole and HCl dissolved in water or an alcohol. Carbonylation using this catalyst involves contacting an olefin stream preferably in a solvent such as o-xylene with the catalyst and carbon monoxide at carbonylation conditions to provide a carboxylic acid or an ester. When the catalyst solvent is water one can obtain an acid as the product, but when the catalyst solvent is an alcohol one obtains an ester as the product.
    Type: Grant
    Filed: October 19, 2004
    Date of Patent: November 11, 2008
    Assignee: UOP LLC
    Inventors: Irina Galperin, legal representative, Paul T. Barger, Robert H. Jensen, Albert L. Lapidus, Oleg L. Eliseev, Leonid B. Galperin
  • Patent number: 7381838
    Abstract: Process for carrying out catalytic multiphase reactions in a tubular reactor, in which at least three reactants are present in three different phases, wherein the process is carried out in at least one tubular reactor, and the catalyst is present in a continuous phase, at least one reactant is present in this continuous phase, and at least two reactants are present dispersed in the continuous phase and the loading factor B of the tubular reactor is equal to or greater than 0.2. In particular, the multiphase reaction is a hydrocarboxylation of at least one olefin to a carboxylic acid.
    Type: Grant
    Filed: March 4, 2005
    Date of Patent: June 3, 2008
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Klaus-Diether Wiese, Wilfried Bueschken
  • Patent number: 7381837
    Abstract: A method comprises continuously supplying an alcohol to a pressurized reaction system, pressurizing carbon monoxide with a compressor 8 attached to a first feed line 22, for continuously supplying carbon monoxide to the reaction system via a second feed line 23 with a reference flow rate F, and converging excess carbon monoxide in the reaction system in the first feed line via a branched circulation line 24 for allowing to react alcohol with carbon monoxide. The reference flow rate F in the second feed line 23 is a total rate of a reference consumption flow rate Fcs in the reaction and a flow rate F1 in excess rate over a fluctuation consumption flow rate ?Fcv in the reaction system (F=Fcs+F1, F1>?Fcv).
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: June 3, 2008
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hidehiko Nakajima, Yoshiyuki Harano, Manabu Yamada
  • Patent number: 7183428
    Abstract: A method for producing acrylic acid by using an acrylic acid-containing solution of high concentration without azeotropic distillation is provided. This method of producing acrylic acid comprises introducing an acrylic acid-containing gas obtained by catalytic gas phase oxidation reaction into an absorption column and supplying the acrylic acid-containing solution to crystallization step thereby separating the solution into acrylic acid and residual mother liquid, and distilling at least part of the residual mother liquid and circulating the distillate obtained by the distillation to the absorption column.
    Type: Grant
    Filed: June 2, 2004
    Date of Patent: February 27, 2007
    Assignee: Nippon Shokubai Co., Inc.
    Inventors: Kouji Ueno, Harunori Hirao, Naoki Serata, Takeshi Yokogoshiya
  • Patent number: 7161044
    Abstract: An object of the present invention is to provide a catalytic gas phase oxidation reaction in which: even under reaction conditions of a higher gas pressure, a higher concentration of the raw material gas and a larger space velocity of a reaction gas, the thermal accumulation at the hot spot portion can be sufficiently suppressed with ease and at low costs, so that the reaction can be continued for a long time while a high yield is maintained.
    Type: Grant
    Filed: October 4, 2004
    Date of Patent: January 9, 2007
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Daisuke Nakamura, Michio Tanimoto
  • Patent number: 6984668
    Abstract: A liquid-phase chemical reaction medium comprises one or more reactants, optionally in the presence of a reaction product(s) and one or more solvents, diluents or other form of liquid carrier, a catalyst system comprising at least a metal or metal compound and optionally further compounds such as ligands or complexing agents; characterized in that the reaction medium further comprises a polymeric dispersant dissolved in said liquid carrier, said polymeric dispersant being capable of stabilizing a colloidal suspension of particles of said metal or metal compound within the liquid carrier. The presence of the polymeric dispersant enables metal formed by catalyst deactivation to be more easily recovered and recycled. Preferably, the polymeric dispersant has sufficiently acidic or basic functionality to stabilize the colloidal suspension of said metal or metal compound.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: January 10, 2006
    Assignee: Lucite International UK Limited
    Inventors: Graham Ronald Eastham, Raymond Anthony Hadden, David William Johnson
  • Patent number: 6916954
    Abstract: The invention relates to a catalyst system for carbonylating olefinically or acetylenically unsaturated compounds with carbon monoxide and a nucleophile compound, containing (a) palladium; (b) a phosphine and (c) a polymer containing nitrogen which is soluble in the reaction mixture, with the exception of polyvinyl polymers with aromatic radicals containing nitrogen on the polymer chain. The invention also relates to a method for carbonylation in the presence of one such catalyst system.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: July 12, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Schäfer, Michael Slany, Edgar Zeller, Michael Röper, Michael Schulz, Günther Grimm
  • Patent number: 6852893
    Abstract: The invention relates to a method for oxidizing substrates such as hydrocarbons, waxes or soot. The method involves the use of a compound of formula (I) in which: R1 and R2 represent H, an aliphatic or aromatic alkoxy radical, carboxyl radical, alkoxycarbonyl radical or hydrocarbon radical, each having 1 to 20 hydrocarbon atoms, SO3H, NH2, OH, F, Cl, Br, I and/or NO2, whereby R1 and R2 designate identical or different radicals or R1 and R2 can be linked to one another via a covalent bonding; Q1 and Q2 represent C, CH, N, CR5, each being the same or different; X and Z represent C, S, CH2, each being the same or different; Y represents O and OH; k=0, 1, 2; l=0, 1, 2; m=1 to 3, and; R5 represents one of the meanings of R1. Said compound is used as a catalyst in the presence of a radical initiator, whereby the molar ratio of the catalyst to the hydrocarbon is less than 10 mol %. Peroxy compounds or azo compounds can be used as the radical initiator. Preferred substrates are aliphatic or aromatic hydrocarbons.
    Type: Grant
    Filed: March 22, 2001
    Date of Patent: February 8, 2005
    Assignee: Creavis Gesellschaft fuer Technologie and Innovation mbH
    Inventors: Adolf Kühnle, Mark Duda, Carsten Jost, Guido Fries, Jochen Kirchhoff, Thomas Schiffer, Roger Arthur Sheldon, Sasidharan Manickam, Isabella W. C. E. Arends
  • Patent number: 6787671
    Abstract: An osmium-assisted process for the oxidative cleavage of oxidizable organic compounds such as unsaturated organic compounds, including alkenes and olefins into aldehydes, carboxylic acids, esters, or ketones. The process uses a metal catalyst comprising osmium and a peroxy compound selected from the group consisting of peroxymonosulfuric acid and salts thereof to oxidatively cleave the oxidizable organic compound. In particular, the process enables aldehydes, carboxylic acids, esters, or ketones to be selectively produced from the corresponding mono-, 1,1-di-, 1,2-di-, tri-, or tetra-substituted olefins in a reaction that produces the result of ozonolysis but with fewer problems. The present invention further provides a process for oxidizing an aldehyde alone or with the osmium in an interactive solvent to produce an ester or carboxylic acid.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: September 7, 2004
    Assignee: Board of Trustees of Michigan State University
    Inventors: Babak Borhan, Benjamin R. Travis, Jennifer M. Schomaker
  • Patent number: 6717010
    Abstract: A method for production of pivalic acid comprising the steps of: (a) reacting isobutylene, carbon monoxide, and a first catalyst to produce a reaction mixture; (b) contacting the reaction mixture with water, thereby producing a crude acid product having pivalic acid and oligomeric neo-carboxylic acid; (c) then separating the pivalic acid and the oligomeric neo-carboxylic acid from the crude acid product; (d) then reacting the oligomeric neo-carboxylic acid with a source of carbon monoxide at a temperature of less than 200° C. in the presence of a second catalyst to produce a C5 carbocation product, wherein the first and second catalyst are either the same or different; and (e) reacting the C5 carbocation product with water; thereby producing pivalic acid having an overall yield of at least 80 wt. %.
    Type: Grant
    Filed: May 9, 2003
    Date of Patent: April 6, 2004
    Inventors: Edmund J. Mozeleski, Richard H. Schlosberg, Dennis J. Davoren, Carl Robert Beck, Linda J. Broadbelt, Ned C. Haubein
  • Publication number: 20040024247
    Abstract: Process for the carbonylation of optionally substituted ethylenically unsaturated compounds by reaction with carbon monoxide and a coreactant in the presence of a catalyst system.
    Type: Application
    Filed: July 31, 2002
    Publication date: February 5, 2004
    Inventor: Eit Drent
  • Publication number: 20040015011
    Abstract: A process for preparing hydroformylation products of propylene and for preparing acrylic acid and/or acrolein comprises a) feeding a propylene-containing feed in which from 2 to 40% by weight of propane is present and also carbon monoxide and hydrogen into a reaction zone and reacting this mixture in the presence of a hydroformylation catalyst to form hydroformylation products of propane, b) separating a stream consisting essentially of unreacted propylene and propane from the output from the reaction zone, and c) subjecting the stream consisting essentially of propylene and propane to a catalytic gas-phase oxidation in the presence of molecular oxygen to form acrylic acid and/or acrolein.
    Type: Application
    Filed: December 26, 2002
    Publication date: January 22, 2004
    Inventors: Roland Krokoszinski, UIrich Hammon, Kevin Todd
  • Patent number: 6677481
    Abstract: A method for production of pivalic acid comprising the steps of: (a) reacting isobutylene, carbon monoxide, and a first catalyst to produce a reaction mixture; (b) contacting the reaction mixture with water, thereby producing a crude acid product having pivalic acid and oligomeric neo-carboxylic acid; (c) then separating the pivalic acid and the oligomeric neo-carboxylic acid from the crude acid product; (d) then reacting the oligomeric neo-carboxylic acid with a source of carbon monoxide at a temperature of less than 200° C. in the presence of a second catalyst to produce a C5 carbocation product, wherein the first and second catalyst are either the same or different; and (e) reacting the C5 carbocation product with water; thereby producing pivalic acid having an overall yield of at least 80 wt. %.
    Type: Grant
    Filed: July 9, 2001
    Date of Patent: January 13, 2004
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Edmund J. Mozeleski, Richard H. Schlosberg, Dennis J. Davoren, Carl Robert Beck, Linda J. Broadbelt, Ned C. Haubein
  • Patent number: 6646159
    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: Grant
    Filed: December 21, 2000
    Date of Patent: November 11, 2003
    Assignee: UOP LLC
    Inventors: Lance A. Baird, Leonid B. Galperin, R. Joe Lawson, Robert H. Jensen, Oleg L. Eliseev, Albert L. Lapidus, Aduard G. Ostapenco
  • Patent number: 6602476
    Abstract: Apparatus and process for heat exchange with fluid beds comprises heat-exchange tubes located longitudinally with respect to the axis of a fluidization zone with a rectangular pitch, one side of which having a length at least one and a half times the length of the other side and/or with a triangular pitch, having two sides each at least one and a half times the length of the shortest side reduces the impact of the heat-exchange tubes on the fluidization characteristics of the fluid bed. The invention is particularly suitable for oxidation reactions using molecular oxygen-containing gas in the presence of a fluid bed of fluidizable catalyst, such as (a) the acetoxylation of olefins, (b) the oxidation of ethylene to acetic acid and/or the oxidation of ethane to ethylene and/or acetic acid, (c) the ammoxidation of propylene and/or propane to acrylonitrile and (d) the oxidation of C4's to maleic anhydride.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: August 5, 2003
    Assignee: BP Chemicals Limited
    Inventors: Stanley John Becker, Timothy Crispin Bristow, Michele Fiorentino, David Newton, Bruce Leo Williams
  • Publication number: 20020177730
    Abstract: A process is proposed for preparing C5 acetate for Vitamin A synthesis by hydroformylation of 3,4-diacetoxybut-1-ene (3,4-DABE), according to which a 3,4-DABE is used which is obtained by acetoxylation of 1,3-butadiene with acetic acid and air in the presence of a catalyst and removing by distillation the 3,4-DABE formed in this case as by-product.
    Type: Application
    Filed: March 27, 2002
    Publication date: November 28, 2002
    Inventors: Udo Rheude, Maximilian Vicari, Werner Aquila, Gunter Wegner, Jorg Niekerken
  • Patent number: 6452043
    Abstract: A method for producing esters, carboxylic acids and mixtures thereof includes contacting, under carbonylation conditions, lower alkyl alcohols, ethers, lower alkyl alcohol derivatives and mixtures thereof and carbon monoxide with a catalyst having a catalytically effective amount a metal selected from iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, tin and mixtures thereof associated with a carbonized polysulfonated divinylbenzene-styrene copolymer matrix. In a preferred aspect of the invention the method is called out under vapor-phase conditions.
    Type: Grant
    Filed: April 5, 2000
    Date of Patent: September 17, 2002
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Andy Hugh Singleton, Gerald Charles Tustin, Donald Lee Carver
  • Patent number: 6407287
    Abstract: In a method for producing acrylic acid by the steps of a reaction of catalytic gas phase oxidation, absorbing the acrylic acid with an absorbent, and dehydrating the acrylic acid-containing aqueous solution, the method is characterized that the step of dehydration comprises adding and an azeotropic solvent, distilling the resultant mixture, and adjusting the acrylic acid concentration at the top of the column in the range of 0.06-0.80 wt. %, thereby preventing the bottoms of the azeotropic dehydration column from substantially containing the azeotropic solvent and water. As results, the acrylic acid is kept from forming a polymer in any of the distillation columns involved in the production, and effective utilization of acrylic acid.
    Type: Grant
    Filed: March 7, 2001
    Date of Patent: June 18, 2002
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yukihiro Matsumoto, Takeshi Nishimura, Kazuhiko Sakamoto, Hidefumi Haramaki
  • 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: 6326455
    Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: December 4, 2001
    Assignee: RPC Inc.
    Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
  • Patent number: 6294691
    Abstract: A process for manufacture of branched carboxylic acids from branched olefins by means of reaction with carbon monoxide and a solid acid catalyst, characterized in that a branched olefin, or a precursor thereof, is reacted in a batch reactor or a plug flow reactor with carbon monoxide and water, in the presence of an acidic ion exchanger, having sufficient acid groups to provide requisite protons for conversion of said olefin or a precursor of it, and carbon monoxide into branched carboxylic acids, and in the presence of a polar non-coordinating organic solvent.
    Type: Grant
    Filed: June 22, 1998
    Date of Patent: September 25, 2001
    Inventor: Jean-Paul Lange
  • Publication number: 20010023285
    Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.
    Type: Application
    Filed: April 5, 2001
    Publication date: September 20, 2001
    Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
  • Patent number: 6239325
    Abstract: The invention provides process for oxidative dehydrogenation of lower alkanes, by vapor phase oxidative dehydrogenation of C2-C5 lower alkanes in the presence of a catalyst and molecular oxygen to produce the corresponding olefins, in which the catalyst has a composition expressed by a general formula (1) below: A&agr;Sb&bgr;W&ggr;D&dgr;Ox   (1) in which A is at least one metal selected from the group consisting of molybdenum and chromium; Sb is antimony; W is tungsten; O is oxygen; and D is at least one metal selected from the group consisting of V, Nb, Ta, Fe, Co, Ni, Cu, Ag, Zn, B, Tl, Sn, Pb, Te, Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce and Sm; &agr;, &bgr;, &ggr;, &dgr; and x denote atomic numbers of A, Sb, W, D and O, respectively, where when &agr;=1, &bgr;=0.5-10, &ggr;=0.1-10 and &dgr;=0-3; and x is a numerical value determined by the state of oxidation of those elements other than oxygen.
    Type: Grant
    Filed: May 18, 1999
    Date of Patent: May 29, 2001
    Assignee: Nippon Shokubai Co Ltd
    Inventors: Nobuji Kishimoto, Etsushige Matsunami
  • Patent number: 6211406
    Abstract: A process for manufacture of &agr;,&agr;-branched carboxylic acids from linear olefins by means of reaction with carbon monoxide and an acid catalyst, characterized in that a linear olefin containing from 2 to 5 carbon atoms, or a precursor thereof, is reacted in a batch reactor or a continuous reactor, with carbon monoxide and water, in the presence of a catalyst having sufficient acid groups to provide requisite protons for the formation of Koch acid, and in the presence of a polar non-coordinating organic solvent.
    Type: Grant
    Filed: October 20, 1999
    Date of Patent: April 3, 2001
    Assignee: Shell Oil Company
    Inventors: Jean-Paul Lange, Vincent Otten, Hans Arie Stil
  • Patent number: 5981796
    Abstract: A process is provided for manufacture of branched carboxylic acids from branched olefins by means of reaction with carbon monoxide and a solid acid catalyst. In this process, a branched olefin, or a precursor thereof, is reacted in continuously backmixed reactor, with continuously supplied carbon monoxide and water, while continuously an effluent is withdrawn comprising branched carboxylic acid, non-converted olefin, carbon monoxide and water, in the presence of an acidic ion exchanger, having sufficient acid groups to provide requisite protons for conversion of the olefin or a precursor of it, and carbon monoxide into branched carboxylic acids.
    Type: Grant
    Filed: February 25, 1998
    Date of Patent: November 9, 1999
    Assignee: Shell Oil Company
    Inventors: Anthonius Johannes Maria Breed, Rene Johan Haan, Jean-Paul Lange, Leonardus Petrus
  • Patent number: 5962732
    Abstract: Process for making 3-pentenoic acid by reacting butadiene with carbon monoxide in the presence of nickel and an iodide source.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: October 5, 1999
    Assignees: E. I. du Pont de Nemours and Company, DSM N.V.
    Inventor: Patrick Michael Burke
  • Patent number: 5936117
    Abstract: Disclosed is a process for the preparation of aliphatic carbonyl compounds selected from aliphatic carboxylic acids, alkyl esters of aliphatic carboxylic acids and anhydrides of aliphatic carboxylic acids by the carbonylation of olefins in the presence of a catalyst system comprising (1) a primary component selected from at least one Group 6 metal, i.e., chromium, molybdenum, and/or tungsten and (2) a secondary component selected from at least one of certain halides and tertiary and quaternary compounds of a Group 15 element, i.e., nitrogen, phosphorus and/or arsenic. The process constitutes and improvement over known processes since it can be carried out at moderate carbonylation conditions without the necessity of using an expensive noble metal catalyst, volatile, toxic materials such as nickel tetracarbonyl, formic acid or a formate ester.
    Type: Grant
    Filed: July 28, 1995
    Date of Patent: August 10, 1999
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Elizabeth MacGowan West, Horace Lawrence Browning, Jr., George Geiger Mayfield
  • Patent number: 5919978
    Abstract: This invention relates in part to processes for producing one or more substituted or unsubstituted aldehyde acids or salts, e.g., 5-formylvaleric acid or salt, which comprises subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and optionally neutralization with a base to produce one or more substituted or unsubstituted unsaturated acids or salts, e.g., pentenoic acid or salt, and subjecting said one or more substituted or unsubstituted unsaturated acids or salts to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted aldehyde acids or salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: July 6, 1999
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Diane Lee Packett, Thomas Carl Eisenschmid, Michael Allen Brammer, John Michael Maher
  • Patent number: 5808143
    Abstract: Catalysts of the formula I?A.sub.a B.sub.b O.sub.x !.sub.p ?C.sub.c D.sub.d Fe.sub.e Co.sub.f E.sub.i F.sub.j O.sub.y !.sub.q I,whereA is bismuth, tellurium, antimony, tin and/or copper,B is molybdenum and/or tungsten,C is an alkali metal, thallium and/or samarium,D is an alkaline earth metal, nickel, copper, cobalt, manganese, zinc, tin, cerium, chromium, cadmium, molybdenum, bismuth and/or mercury,E is phosphorus, arsenic, boron and/or antimony,F is a rare-earth metal, vanadium and/or uranium,a is from 0.01 to 8,b is from 0.1 to 30,c is from 0 to 4,d is from 0 to 20,e is from 0 to 20,f is from 0 to 20,i is from 0 to 6,j is from 0 to 15,x and y are numbers determined by the valency and frequency of the elements other than oxygen in I, and p and q are numbers whose ratio p/q is in the range from 0.001 to 0.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: September 15, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Karrer, Hans-Peter Neumann, Hans-Dieter Eichhorn, Robin Stuart Jarret
  • Patent number: 5783735
    Abstract: A process for preparing polymeric amides is disclosed. The process comprises sequentially reacting a hydrocarbon polymer functionalized (e.g., via the Koch reaction) to contain acid, ester, thioacid and/or thioester groups with a heavy polyamine to form a partially derivatized product in which at least about 85% of the functional groups are converted to heavy (thio)amide groups, and then reacting the partially derivatized product with an excess of light amine to complete the derivatization by converting substantially all of the remaining functional groups to light (thio)amide groups. Products of the foregoing process are also disclosed, which products are useful as additives in fuels and in lubricants.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: July 21, 1998
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Jacob I. Emert, Joseph V. Cusumano, David C. Dankworth, William D. Diana, William B. Eckstrom, Keith R. Gorda, Antonio Gutierrez, Jon E. Stanat, Warren A. Thaler, Stephen Zushma
  • Patent number: 5760284
    Abstract: Disclosed is an improved catalyst system and process for preparing aliphatic carbonyl compounds such as aliphatic carboxylic acids, alkyl esters of aliphatic carboxylic acids and anhydrides of aliphatic carboxylic acids by carbonylating olefins in the presence of a catalyst system comprising (1) a first component selected from at least one Group 6 metal, i.e., chromium, molybdenum, and/or tungsten and (2) a second component selected from at least one of certain halides and tertiary and quaternary compounds of a Group 15 element, i.e., nitrogen, phosphorus and/or arsenic, and (3) as a third component, a polar, aprotic solvent. The process employing the improved catalyst system is carried out under carbonylating conditions of pressure and temperature discussed herein.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: June 2, 1998
    Assignee: Eastman Chemical Company
    Inventor: Joseph Robert Zoeller
  • Patent number: 5731486
    Abstract: A method for producing 3-methyl-2-pentene which is substantially free of any other C.sub.6 olefin, except 2-ethyl-1-butene, by first producing a stream that contains 2-ethyl-1-butene from the trimerization of ethylene, and second by recovering the 2-ethyl-1-butene as 3-methyl-2-pentene via etherification, separation of the ether, and decomposition of the ether back to predominantly 3-methyl-2-pentene with some 2-ethyl-1-butene.
    Type: Grant
    Filed: July 17, 1995
    Date of Patent: March 24, 1998
    Assignee: Exxon Chemical Patents Inc
    Inventors: Dan E. Hendriksen, Gerald G. McGlamery, Michael J. Keenan, Derrick D. Pete
  • Patent number: 5710326
    Abstract: A process for controlling the regeneration of boron trifluoride catalyst complexes in the production of carboxylic acids and other products using boron trifluoride hydrates as a catalyst. Catalyst strength is determined by measuring the electrical conductivity of the catalyst recovered from hydrolysis. If the conductivity is greater than a predetermined value, the hydrolysis water rate is reduced and if the conductivity is leas than a predetermined value, the hydrolysis water rate is increased. Conductivity is determined by a toroidal conductivity sensor and a control valve responsive to operation of the conductivity sensor serves to increase or decrease the flow rate accordingly.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: January 20, 1998
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Carl R. Beck
  • Patent number: 5710323
    Abstract: A process for producing a monocarboxylic acid and/or a dicarboxylic acid by the reaction of a starting compound selected from among saturated hydrocarbons, .alpha.-olefins of 6 to 20 carbon atoms, saturated monocarboxylic acids and esters of the acids either with both of carbon monoxide and water at the same time or first with carbon monoxide and then with water, wherein the reaction of the starting compound either with both of carbon monoxide and water or with carbon monoxide alone is conducted in a strong acid solution containing a trifluoromethane-sulfonic acid catalyst and an alcohol and/or an olefin of 3 to 5 carbon atoms.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: January 20, 1998
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Ryoichi Okuda, Tadashi Kato, Yoshio Okada
  • Patent number: 5466874
    Abstract: A carbonylation catalyst useful for the carbonylation of methanol to acetic acid, acetic anhydride or both comprises a polymer support containing pendant pyrrolidone groups which support a rhodium species. Other polymeric supports capable of withstanding carbonylation temperatures of at least 150.degree. C. are disclosed for the carbonylation reaction in which rhodium levels in the reaction medium of greater than 500 ppm are contemplated.
    Type: Grant
    Filed: August 24, 1993
    Date of Patent: November 14, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Mark O. Scates, R. Jay Warner, G. Paull Torrence
  • Patent number: 5463157
    Abstract: A method for producing 3-methyl-2-pentene which is substantially free of any other C.sub.6 olefin, except 2-ethyl-1-butene, by first producing a stream that contains 2-ethyl-1-butene from the trimerization of ethylene, and second by recovering the 2-ethyl-1-butene as 3-methyl-2-pentene via etherification, separation of the ether, and decomposition of the ether back to predominantly 3-methyl-2-pentene with some 2-ethyl-1-butene.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: October 31, 1995
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Dan E. Hendriksen, Gerald G. McGlamery, Michael J. Keenan, Derrick D. Pete
  • Patent number: 5342979
    Abstract: In a process for the production of tertiary carboxylic acids, especially by "Koch synthesis", the byproducts, e.g., a dimer of tripropene, are removed from the reaction mixture by azeotropic rectification with alkanediols, e.g., 1,3-butanediol, as entrainers, thus obtaining the tertiary carboxylic acids in pure form.
    Type: Grant
    Filed: March 17, 1993
    Date of Patent: August 30, 1994
    Assignee: Huels Aktiengesellschaft
    Inventors: Wolfgang H. E. Mueller, Manfred Hartmann
  • Patent number: 5281752
    Abstract: Lower carboxylic acids such as acetic acid, are produced efficiently from inexpensive lower alkanes such as methane by allowing the lower alkanes to react with carbon monoxide in the presence of palladium and/or copper catalysts and salts of peroxy acids.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: January 25, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuzo Fujiwara, Ken Takaki
  • Patent number: 5241112
    Abstract: This invention is a process for the production of trialkyl acetic acids, particularly of pivalic acid, from branched olefins, particularly isobutene, and carbon monoxide using a solid acid catalyst and optionally with minor amounts of a Lewis acid such as boron trifluoride.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: August 31, 1993
    Assignee: Catalytica, Inc.
    Inventors: William A. Sanderson, Michael A. Richard
  • Patent number: 5227521
    Abstract: This invention is a process for the production of trialkyl acetic acids, particularly of pivalic acid, from branched olefins, particularly isobutene, and carbon monoxide using catalytic amounts of a Lewis acid such as boron trifluoride.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: July 13, 1993
    Assignee: Catalytica Inc.
    Inventors: Michael A. Richard, William A. Sanderson