Alkane Patents (Class 562/549)
  • Patent number: 6346647
    Abstract: A metal oxide catalyst which can produce acrylic acid by a vapor phase catalytic oxidation of propane in high yield and has excellent abrasion resistance is disclosed. The metal oxide catalyst comprises Mo, V, Sb, A (A represents Nb or Ta) and optionally other metals, and is prepared through the following steps (1) and (2): (1) Step of reacting V+5 and Sb+3 at a temperature of 70° C. or higher in the presence of Mo+6 in an aqueous medium, and bubbling an oxygen-containing gas into the reaction solution during or after the reaction; and (2) Step of adding to the reaction product obtained in step (1) a solution containing a compound comprising A and an aqueous solution of nitric acid or ammonium nitrate, uniformly stirring these components, and then calcining the resulting mixture.
    Type: Grant
    Filed: April 9, 2001
    Date of Patent: February 12, 2002
    Assignee: Toagosei Co., Ltd.
    Inventors: Xinlin Tu, Mamoru Takahashi, Madoka Furuta, Hiroshi Niizuma
  • Patent number: 6320075
    Abstract: A process and an apparatus are for preparing saturated carboxylic acids having from one to four carbon atoms by gas-phase oxidation at a reaction temperature of from 100° C. to 400° C. and pressures of from 1.2×105 to 51×105 Pa in the presence of saturated or unsaturated C4-hydrocarbons and mixtures thereof. Also present in the reactor are an oxygen-containing gas and water vapor and in the presence of at least one catalyst, with part of the reactor outlet gas being recirculated in a reaction gas circuit. The acid concentration in the recirculated portion is reduced by means of a separation step, and the crude acid is separated from the reactor outlet gas by means of a countercurrent scrubber.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: November 20, 2001
    Assignee: Consortium für elektrochemische Industrie GmbH
    Inventors: Christoph Ruedinger, Hans-Juergen Eberle, Michael Hallmann
  • Patent number: 6310241
    Abstract: An oxide catalyst comprising the elements Mo, V, Nb and Pd. The novel catalytic system provides both higher selectivity and yield of acetic acid in the low temperature one step vapor phase direct oxidation of ethane with molecular oxygen containing gas without production of side products such as ethylene and CO. The feed gas is contacted with a catalyst containing Mo, V, Nb, Pd and O in the ratio a:b:c:d:x where a is 1 to 5; b is 0 to 0.5; c is 0.01 to 0.5; d is 0 0.2 and x is a number determined by the valence of the other elements in the catalyst.
    Type: Grant
    Filed: December 14, 1999
    Date of Patent: October 30, 2001
    Assignee: Saudi Basic Industries Corporation
    Inventors: Khalid Karim, Edouard Mamedov, Mohammed H. Al-Hazmi, Anis H. Fakeeha, Mustaf A. Soliman, Yousef S. Al-Zeghayer, Ahmed S. Al-Fatish, Abdulsalm A. Al-Arify
  • Patent number: 6274765
    Abstract: A process is disclosed for selectively preparing acetic acid from a gaseous feed of ethane, ethylene or mixtures thereof, as well as oxygen, at an increased temperature, on a catalyst which contains the elements W, X, Y and Z in the gram-atom ratio a:b:c:d, associated with oxygen. In the formula WaXbYcZd (I), X stands for one or several elements selected from the group Pd, Pt, Ag and/or Au; Y stands for one or several elements selected from the group V, Nb, Cr, Mn, Fe, Sn, Sb, Cu, Zn, U, Ni and/or Bi; Z stands for one or several elements selected from the group Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, Sc, Y, La, Ti, Zr, Hf, Ru, Os, Co, Rh, Ir, B, Al, Ga, In, Tl, Si, Ge, Pb, P, As and/or Te; a equals 1, b is a number higher than 0, c is a number higher than 0, and d is a number from 0 to 2. Also disclosed is said catalyst.
    Type: Grant
    Filed: November 10, 1999
    Date of Patent: August 14, 2001
    Assignee: Hoechst Research & Technology Deutschland GmbH & Co. KG
    Inventors: Holger Borchert, Uwe Dingerdissen, Ranier Roesky
  • Patent number: 6258992
    Abstract: Lower hydrocarbons are converted to carboxylic acids and/or dehydrogenated hydrocarbon product by contacting a feed mixture containing lower hydrocarbons, oxygen source, diluent, and sulfur-containing compound, with a multifunctional, mixed metal catalyst at a temperature from about 150° C. up to about 400° C. The lower hydrocarbons include C2-C4, and the presence of sulfur compound in the feed mixture results in increased yield of carboxylic acid and/or dehydrogenated hydrocarbon product.
    Type: Grant
    Filed: September 17, 1999
    Date of Patent: July 10, 2001
    Assignee: Saudi Basic Industries Corporation
    Inventors: Khalid Karim, Asad Khan
  • Patent number: 6252122
    Abstract: In an industrial process for the heterogeneously catalyzed gas-phase oxidation of propane with molecular oxygen to give acrolein, the feed gas mixture having an initial undiluted molar ratio of the reactants propane:O2 of 7:3 is diluted with the reactant propane and, if desired, inert gases in such a way that the feed gas mixture comprises more than 70% by volume of propane and at least 5% by volume of O2.
    Type: Grant
    Filed: December 4, 1998
    Date of Patent: June 26, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Tenten, Theo Proll, Hans-Peter Schildberg
  • Patent number: 6180825
    Abstract: A process for preparing a catalyst comprises: admixing metal compounds, at least one of which is an oxygen containing compound, and at least one solvent to form a solution; removing the solvent from the solution to obtain a catalyst precursor; and calcining the catalyst precursor under an inert atmosphere to form a catalyst having the formula AaMmNnXxOo wherein a, m, n, x and o are the molar proportions of A, M, N, X and O, respectively, and o is dependent on the oxidation state of the elements A, M, N and X, wherein A is Mo, W, Fe, Nb, Ta, Zr, Ru or mixtures thereof, M is V, Ce, Cr or mixtures thereof, N is Te, Bi, Sb, Se or mixtures thereof, and X is Nb, Ta, W, Ti, Al, Zr, Cr, Mn, Fe, Ru, Co, Rh, Ni, Pd, Pt, Sb, Bi, B, In, Ce or mixtures thereof. The catalyst is useful for the gas phase oxidation of alkanes to unsaturated aldehydes or carboxylic acids.
    Type: Grant
    Filed: May 21, 1999
    Date of Patent: January 30, 2001
    Assignee: Rohm and Haas Company
    Inventors: Manhua Lin, Michael William Linsen
  • Patent number: 6169202
    Abstract: Alkanes are converted to unsaturated carboxylic acids by contacting an alkane with an oxidizing agent and a Wells-Dawson type heteropolyacid supported on wide pore polyoxometallate salts.
    Type: Grant
    Filed: March 14, 2000
    Date of Patent: January 2, 2001
    Assignees: Sunoco, Inc. (R&M), Rohm and Haas Company
    Inventors: Tilak P. Wijesekera, James E. Lyons, Paul E. Ellis, Jr.
  • Patent number: 6166241
    Abstract: The present invention relates to a method for the simultaneous production of acrylonitrile and acrylic acid by reacting propane with ammonia and oxygen in the gas phase catalytic oxidation in the presence of a metal oxide catalyst containing vanadium and at least one member selected from tellurium, antimony and molybdenum and adjusting the molar ratio of propane to ammonia to from 2 to 10 and the molar ratio of oxygen to ammonia to from 2 to 10.
    Type: Grant
    Filed: May 13, 1999
    Date of Patent: December 26, 2000
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Atsushi Kayou, Tatsuya Ihara
  • Patent number: 6143921
    Abstract: Methods for the catalytic production of vinyl acetate monomer from ethane, ethylene or an ethane/ethylene mixture using a first catalyst containing MoVNbPd, MoVLaPdNbX (where X is Al, Ga, Ge or Si) or MoVNbX (where X is P, B, Hf, Te, As or mixtures thereof) in the first step of oxidation and using a conventional VAM catalyst for the second step. The method produces high yields to acetic acid and vinyl acetate without the coproduction of carbon monoxide.
    Type: Grant
    Filed: May 14, 1999
    Date of Patent: November 7, 2000
    Assignee: Saudi Basic Industries Corporation
    Inventors: Khalid Karim, Alaa E. M. Adris
  • Patent number: 6114274
    Abstract: The aliphatic carboxylic acids, e.g., acetic acid, are selectively prepared, even on an industrial scale, by controlledly oxidizing the corresponding alkanes, e.g., ethane, with a source of oxygen, in the presence of a catalytically effective amount of an advantageously supported heteropolyacid catalyst having the formula (I):[A.sub.a B.sub.b ].sub.f [C.sub.c D.sub.d E.sub.e O.sub.x ].sup.f-(I)in which A is at least one monovalent cation selected from among hydrogen, an alkali metal, or the ammonium ion; B is VO.sup.2 +, VO.sup.3 +, an alkaline earth metal ion, or an ion of a metal of Groups VII A, VIII, I B, IV B and V B of the Periodic Table; C is Mo and/or W; D is phosphorus, arsenic, antimony, silicon, germanium and/or boron; E is vanadium, optionally in combination with at least one metal of Groups V A, VII A and VIII of the Periodic Table or chromium; f=a+.alpha.b wherein .alpha.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: September 5, 2000
    Assignee: Rhone-Poulenc Chimie
    Inventors: Elisabeth Bordes, Michel Gubelmann, Laurent Tessier
  • Patent number: 6057475
    Abstract: Process for the liquid phase oxidation of butane to produce acetic acid in which oxygen and butane are reacted in the presence of a cobalt catalyst in a liquid reaction composition in an oxidation reaction zone at a temperature in the reaction zone in the range of 136.degree. to 150.degree. C., while continuously maintaining a concentration of oxygen throughout the reaction zone equivalent to a partial pressure of oxygen greater than two bar. The concentration of cobalt oxidation catalyst in the liquid reaction composition is at least 0.12% by weight cobalt and up to its limit of solubility in the liquid reaction composition.
    Type: Grant
    Filed: July 20, 1999
    Date of Patent: May 2, 2000
    Assignee: BP Chemicals, Limited
    Inventors: Derek Alan Colman, Jeremy Bernard Cooper, Andrew Richard Lucy
  • Patent number: 6034270
    Abstract: A process for the selective preparation of acetic acid from a gaseous feed comprising ethane, ethylene or mixtures thereof plus oxygen at elevated temperature, which comprises bringing the gaseous feed into contact with a catalyst comprising the elements Mo, Pd, Re, X and Y in gram atom ratios a:b:c:d:e in combination with oxygenMo.sub.a Pd.sub.b Re.sub.c X.sub.d Y.sub.e (I)where the symbols X, Y have the following meanings:X=Cr, Mn, Nb, B, Ta, Ti, V and/or WY=Bi, Ce, Co, Cu, Te, Fe, Li, K, Na, Rb, Be, Mg, Ca, Sr, Ba, Ni, P, Pb, Sb, Si, Sn, Tl and/or U;the indices a, b, c, d and e are the gram atom ratios of the corresponding elements, wherea=1, b>0, c>0, d=0.05-2, e=0-3.
    Type: Grant
    Filed: November 19, 1998
    Date of Patent: March 7, 2000
    Assignee: Hoechst Research & Technology Deutschland GmbH & Co. KG
    Inventors: Holger Borchert, Uwe Dingerdissen, Jens Weiguny
  • Patent number: 5994580
    Abstract: A process for producing acrylic acid from propane and oxygen gas through a vapor-phase catalytic oxidation reaction, said process comprising conducting the reaction using as a catalyst a metal oxide containing metallic elements Mo, V, Sb, and A (provided that A is at least one element selected from the group consisting of Nb, Ta, Sn, W, Ti, Ni, Fe, Cr, and Co). The metal oxide is prepared by a process including specific steps (1) and (2). The metal oxide may be supported on a compound containing specific elements.
    Type: Grant
    Filed: October 21, 1997
    Date of Patent: November 30, 1999
    Assignee: Toagosei Co., Ltd.
    Inventors: Mamoru Takahashi, Xinlin Tu, Toshiro Hirose, Masakazu Ishii
  • Patent number: 5990348
    Abstract: Alkanes are converted to unsaturated carboxylic acids by contacting an alkane with an oxidizing agent and a heteropolyacid supported on wide pore polyoxometallate salts.
    Type: Grant
    Filed: January 5, 1998
    Date of Patent: November 23, 1999
    Assignees: Sunoco, Inc., Rohm and Haas Company
    Inventors: James E. Lyons, Anthony F. Volpe, Paul E. Ellis, Jr., Swati Karmakar
  • Patent number: 5981420
    Abstract: A substrate (e.g., a cycloalkane, a polycyclic hydrocarbon, an aromatic compound having a methyl group) is oxidized with oxygen in the presence of an oxidation catalytic system comprising an imide compound of the following formula (1) (e.g., N-hydroxyphthalimide) and a co-catalyst containing a element selected from Group 3 to 12 elements (in particular, Group 4 to 11 elements) of the Periodic Table of Elements. The co-catalyst comprises a compound containing plural elements (except heteropolyacid and a combination of Group 7 and 8 elements of the Periodic Table of Elements), and is useful for the formation of an oxide (e.g., a ketone, an alcohol, a carboxylic acid): ##STR1## wherein R.sup.1 and R.sup.2 represent a substituent such as a hydrogen atom or a halogen atom, or R.sup.1 and R.sup.2 may together form a double bond or an aromatic or nonaromatic 5- to 12-membered ring, X is O or OH, and n is 1 to 3.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: November 9, 1999
    Assignees: Daicel Chemical Industries, Ltd., Yasutaka Ishii
    Inventors: Tatsuya Nakano, Yasutaka Ishii
  • Patent number: 5939582
    Abstract: Methods and apparatuses for controlling exothermic reactions involving a first reactant contained in a liquid and a second reactant in a gas to form a reaction product by atomizing the liquid in an environment of a gas and removing heat of reaction by condensing vapors of the liquid in a reaction chamber. Preferably, the condensation takes place on a simultaneously atomized second liquid of lower temperature than the atomized liquid containing the first reactant. The compositions of the two liquids are preferably similar. This invention provides waste minimization and considerable environmental improvement.
    Type: Grant
    Filed: July 17, 1998
    Date of Patent: August 17, 1999
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark William Dassel, Eustathios Vassiliou
  • Patent number: 5907056
    Abstract: An oxide catalyst comprising the elements Mo, V and Nb with small amounts of phosphorus, boron, hafnium, Te and/or As. The modified catalyst provides both higher selectivity and yield of acetic acid in the low temperature oxidation of ethane with molecular oxygen-containing gas. A process for the higher selective production of acetic acid by the catalytic oxidation of ethane with oxygen, in the presence of the improved catalyst.
    Type: Grant
    Filed: May 27, 1998
    Date of Patent: May 25, 1999
    Assignee: Saudi Basic Industries Corp.
    Inventors: Khalid Karim, Mohammed H. Al-Hazmi, Edouard Mamedov
  • Patent number: 5883292
    Abstract: Methods and apparatuses for controlling exothermic reactions involving a first reactant contained in a liquid and a second reactant in a gas to form a reaction product by atomizing the liquid in an environment of a gas and removing heat of reaction by condensing vapors of the liquid in a reaction chamber. Preferably, the condensation takes place on a simultaneously atomized second liquid of lower temperature than the atomized liquid containing the first reactant. The compositions of the two liquids are preferably similar. This invention provides waste minimization and considerable environmental improvement.
    Type: Grant
    Filed: January 17, 1996
    Date of Patent: March 16, 1999
    Assignee: Twenty-First Century Research Corporation
    Inventors: Mark William Dassel, Eustathios Vassiliou
  • Patent number: 5847227
    Abstract: A method for producing aryl alkyl hydroperoxides which comprises selectively oxidizing an aryl alkyl hydrocarbon having the formula: ##STR1## wherein P and Q are hydrogen or an alkyl and may be the same or different from each other; x is an integer of 1-3; and Ar is an aromatic hydrocarbon group having a valence of x, with an oxygen-containing gas in the presence of a transition metal complex which contains, as a ligand, a cyclic polyfunctional amine compound having at least three nitrogen atoms in the ring forming molecular chain or an open chain polyfunctional amine compound having at least three nitrogen atoms in the main chain of the molecule.
    Type: Grant
    Filed: February 27, 1996
    Date of Patent: December 8, 1998
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Terunori Fujita, Shigekazu Matsui, Toshihiro Takai, Hideto Matsuoka, Akifumi Kagayama, Hiroshi Kuroda, Masayasu Ishibashi, Hiroshi Iwasaki, Nobuya Hirokane
  • Patent number: 5750777
    Abstract: The present invention relates to a process for the preparation of carboxylic acids by controlled oxidation of the corresponding alkanes.The process according to the invention consists in reacting the alkane with a source of oxygen, the reaction being performed in the presence of a catalyst in which the active phase is based on vanadium, titanium, molybdenum, phosphorus and oxygen.
    Type: Grant
    Filed: December 27, 1995
    Date of Patent: May 12, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Alain Aubry, Michel Gubelmann, Anne-Marie Le Govic
  • Patent number: 5705685
    Abstract: Alkanes are converted to unsaturated carboxylic acids by contacting an alkane with an oxidizing agent and a heteropolyacid or polyoxoanion comprising (1) at least 9 atoms of a first framework metal or metals comprising molybdenum, tungsten or vanadium or combinations thereof and (2) 1 to 3 atoms of a second framework metal or metals comprising zinc or a transition metal different from the first framework metal.
    Type: Grant
    Filed: October 31, 1995
    Date of Patent: January 6, 1998
    Assignee: Sun Company, Inc. (R&M)
    Inventors: James E. Lyons, Paul E. Ellis, Jr., Swati Karmakar, Shahid N. Shaikh
  • Patent number: 5449821
    Abstract: A process for the gas phase catalytic oxidation of a C.sub.3-6 alkane, alkanol, alkene or alkenal using as a catalyst multimetal oxide compositions of the formula I, [X.sup.1.sub.a X.sup.2.sub.b O.sub.x ].sub.p [X.sup.3.sub.c X.sup.4.sub.d X.sup.5.sub.e X.sup.6.sub.f X.sup.7.sub.g X.sup.2.sub.h O.sub.y ].sub.q, where X.sup.1 is bismuth, tellurium, antimony, tin and/or copper, X.sup.2 is molybdenum and/or tungsten, X.sup.3 is an alkali metal, thallium and/or samarium, X.sup.4 is an alkaline earth metal, nickel, cobalt, copper, manganose, zinc, tin, cadmium and/or mercury, X.sup.6 is iron, chromium, cerium and/or vanadium, X.sup.6 is phosphorus, arsenic, boron and/or antimony, X.sup.7 is a rare-earth metal, titanium, zirconium, niobium, tantalum, rhenium, ruthenium, rhodium, silver, gold, aluminum, gallium, indium, silicon, geranium, lead, thorium and/or uranium, a is from 0.01 to 8, b is from 0.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: September 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Peter Neumann, Hans Martan, Hermann Petersen, Walter Doerflinger
  • Patent number: 5393922
    Abstract: A process for catalytic direct oxidation of hydrocarbons, particularly lower alkanes and single ring aromatics, to acids by dioxygen under mild temperature conditions using specified metal or metal salt catalysts. Turnovers in excess of 1000 for acetic acid formation from ethane and in excess of 100 for formic acid formation from methane have been obtained at reaction temperatures below about 100.degree. C. using palladium catalyst. A coreductant of carbon monoxide in an aqueous system is preferred.
    Type: Grant
    Filed: July 22, 1993
    Date of Patent: February 28, 1995
    Assignee: Gas Research Institute
    Inventors: Ayusman Sen, Minren Lin
  • Patent number: 5380933
    Abstract: A method for producing an unsaturated carboxylic acid, which comprises subjecting an alkane to a vapor phase catalytic oxidation reaction in the presence of a catalyst containing a mixed metal oxide comprising, as essential components, Mo, V, Te, O and X wherein X is at least one element selected from the group consisting of niobium, tantalum, tungsten, titanium, aluminum, zirconium, chromium, manganese, iron, ruthenium, cobalt, rhodium, nickel, palladium, platinum, antimony, bismuth, boron, indium and cerium, wherein the proportions of the respective essential components, based on the total amount of the essential components exclusive of oxygen, satisfy the following formulas:0.25<r.sub.Mo <0.980.003<r.sub.V <0.50.003<r.sub.Te <0.50.003<r.sub.X <0.5wherein r.sub.Mo, r.sub.V, r.sub.Te and r.sub.X are molar fractions of Mo, V, Te and X, respectively, based on the total amount of the essential components exclusive of oxygen.
    Type: Grant
    Filed: January 28, 1994
    Date of Patent: January 10, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Takashi Ushikubo, Hiroya Nakamura, Yukio Koyasu, Shin Wajiki
  • Patent number: 5348927
    Abstract: A method of removing chloride from phosphorus/vanadium/oxygen mixed oxide oxidation catalysts comprising treating a chloride containing catalyst comprising phosphorus, vanadium and oxygen with a stream of gas comprising oxygen, steam and an inert gas at flow rate and temperature and for a period of time to substantially reduce the amount of chloride in the catalyst.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: September 20, 1994
    Assignee: Scientific Design Company, Inc.
    Inventor: Arie Bortinger
  • Patent number: 5300682
    Abstract: Disclosed is a process for making acetic acid which comprises oxidizing ethane with molecular oxygen in a reaction zone at a pressure of at least 100 psig while the reactants are in contact with a solid catalyst having the elements and relative atomic proportions indicated by the empirical formula:VP.sub.a M.sub.b O.sub.xwhere M is one or more optional element selected from Co, Cu, Re, Fe, Ni, Nb, Cr, W, U, Ta, Ti, Zr, Zn, Hf, Mn, Pt, Pd, Sn, Sb, Bi, Ce, As, Ag, and Au,whereina is 0.5 to 3,b is 0 to 1, andx is a number determined by the valence requirements of the other elements in the catalyst, andwherein said catalyst contains crystalline vanadyl pyrophosphate.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 5, 1994
    Assignee: The Standard Oil Co.
    Inventors: Patricia R. Blum, Marc A. Pepera
  • Patent number: 5210293
    Abstract: A process and catalyst for the production of ethylene and/or acetic acid by oxidation of ethane and/or ethylene with a molecular oxygen-containing gas in the presence of a catalyst composition comprising the elements A, X and Y in combination with oxygen, the gram-atom ratios of the elements A:X:Y being a:b:c, wherein A=Mo.sub.d Re.sub.e W.sub.f ; X=Cr, Mn, Nb, Ta, Ti, V and/or W; Y=Bi, Ce, Co, Cu, Fe, K, Mg, Ni, P, Pb, Sb, Si, Sn, Tl and/or U; a=1; b=0 to 2; c=0 to 2; d+e+f=a; d is either zero or greater than zero; e is greater than zero; and f is either zero or greater than zero.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: May 11, 1993
    Assignee: BP Chemicals Limited
    Inventor: Melanie Kitson
  • Patent number: 5198580
    Abstract: Disclosed is a process for the partial oxidation of propane to yield acrylic acid, propylene, acrolein and acetic acid by contacting propane in admixture with a molecular oxygen-containing gas in a reaction zone with an oxidic solid catalyst that1) contains the components and proportions represented by the empirical formulaBi.sub.b Mo.sub.c V.sub.v A.sub.a D.sub.d E.sub.e O.sub.xwhereinA is one or more of K, Na, Li, Cs and Tl,D is one or more of Fe, Ni, Co, Zn, Ce and La,E is one or more of W, Nb, Sb, Sn, P, Cu, Pb, B, Mg, Ca and Sr,a, d and e are each zero-10b is 0.1-10c is 0.1-20v is 0.1-10c:b is from 2:1 to 30:1v:b is from 1.5:1 to 8:1and2) is made by performing a bismuth molybdate containing composition having at least 0.67 atoms of Mo per atom of Bi, before combining with any vanadium compound.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: March 30, 1993
    Assignee: The Standard Oil Company
    Inventors: Joseph P. Bartek, Ann M. Ebner, James R. Brazdil
  • Patent number: 5191116
    Abstract: The present invention is directed to a process for preparing methacrylic acid and methacrolein in one step which comprises subjecting isobutane to catalytic oxidation in the presence of molecular oxygen in the vapor phase, with a catalyst comprising a P and/or As--Mo--V and/or Cu composition containing a heteropoly acid. The catalytic oxidation is performed at a temperature of not greater than 350.degree. C., at which temperature the decomposition of the heteropoly acid is unlikely to occur, preferably at a temperature of not greater than 320.degree. C. By means of this process, methacrylic acid and methacrolein are produced with high productivity and in high yield while maintaining a stable activity of the catalyst for a prolonged period of time.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: March 2, 1993
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Setsuo Yamamatsu, Tatsuo Yamaguchi
  • Patent number: 5162578
    Abstract: A process for the higher selective production of acetic acid by the catalytic oxidation with oxygen of ethane, or ethylene, or mixtures thereof, in contact with a mixed catalyst composition containing (A) a calcined mixed oxides catalyst of the formula:Mo.sub.x V.sub.y Z.sub.zwherein Z represents nothing or a metal from a group of metals as hereinafter defined and (B) is an ethylene hydration catalyst and/or an ethylene oxidation catalyst.
    Type: Grant
    Filed: June 12, 1987
    Date of Patent: November 10, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: James H. McCain, Jr., Steven W. Kaiser, George L. O'Connor
  • Patent number: 5112864
    Abstract: This invention relates to novel compounds for treating inflammatory conditions by inhibition of phospholipase A.sub.2 activity of the formula ##STR1## wherein X is oxygen, sulfur or --CH.dbd.CH--; wherein R.sup.1 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation;wherein R.sup.2 is phenoxy, alkoxy, methyl, trifluoromethyl or phenyl;wherein n is an integer from 1 to 20;compositions comprised of the novel compounds; and methods of treating inflammatory conditions with these compositions.
    Type: Grant
    Filed: May 30, 1991
    Date of Patent: May 12, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Stephen H. Docter, Richard A. Haack
  • Patent number: 5106407
    Abstract: The present invention discloses the antimicrobial utility of certain iodonium ylide compounds. The particular iodonium ylide compounds are phenyl iodonium ylides having an ortho substituent that stabilizes the positive charge on the polyvalent iodine by a nonbonded electrostatic interaction. The polyvalent iodine is further stabilized by a cyclic 1,3-dicarbonyl anion.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: April 21, 1992
    Assignee: The Dow Chemical Company
    Inventors: Attila G. Relenyi, Gerald F. Koser, Richard W. Walter, Jr., William J. Kruper, Jr., Ravi B. Shankar, Anthony P. Zelinko
  • Patent number: 5019652
    Abstract: An improved catlayst and method for the oxyhydrochlorination of methane is disclosed. The catalyst includes a pyrogenic porous support on which is layered as active material, cobalt chloride in major proportion, and minor proportions of an alkali metal chloride and of a rare earth chloride. On contact of the catalyst with a gas flow of methane, HC1 and oxygen, more than 60% of the methane is converted and of that converted more than 40% occurs as monochloromethane. Advantageously, the monochloromethane can be used to produce gasoline boiling range hydrocarbons with the recycle of HCl for further reaction. This catalyst is also of value for the production of formic acid as are analogous catalysts with lead, silver or nickel chlorides substituted for the cobalt chloride.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: May 28, 1991
    Assignee: The United States as represented by the United States Department of Energy
    Inventors: Charles E. Taylor, Richard P. Noceti
  • 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: 4720575
    Abstract: The molybdovanadophosphoric acid H.sub.8 PMo.sub.10 VO.sub.39, its PMo.sub.10 VO.sub.35 anhydride, methods for their preparation, and methods for making methacrylic acid and its esters by oxidation/dehydrogenation wherein the above acid and/or its anhydride is employed as a catalyst.
    Type: Grant
    Filed: March 7, 1986
    Date of Patent: January 19, 1988
    Assignee: Rohm GmbH
    Inventor: Wilhelm Gruber
  • Patent number: 4472314
    Abstract: Mixed oxides of bismuth with other metals of the perovskite structure and having vacant lattice sites in the same lattice positions occupied by bismuth are disclosed as partial oxidation and ammoxidation catalysts. Such oxides are used as catalysts in the improved method of oxidizing an acyclic hydrocarbon of 1-10 carbons having at most one olefinic unsaturation by reacting the acyclic hydrocarbon in the vapor phase with oxygen in the presence of the solid catalyst to form products having carbon, hydrogen and oxygen.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: September 18, 1984
    Assignee: Allied Corporation
    Inventors: William C. Conner, Jr., Stuart L. Soled, Anthony J. Signorelli, Bruce A. DeRites
  • Patent number: 4420634
    Abstract: The invention relates to a process for the oxidation of unsaturated hydrocarbons, particularly butenes and isobutylene, for the production of acetic acid, propionic acid and acetone. Specifically the invention comprises the highly selective oxidation of an unsaturated hydrocarbon or of a mixture of unsaturated hydrocarbons in the presence of a catalyst consisting of a complex of trivalent cobalt and of a carbonyl compound, of the aldehydic or ketonic type.
    Type: Grant
    Filed: December 8, 1980
    Date of Patent: December 13, 1983
    Inventors: Franco Codignola, Paolo Gronchi, Renato del Rosso, Paolo Centola
  • Patent number: 4375552
    Abstract: Waste streams from adipic acid manufacture containing nitric, succinic, glutaric and adipic acids and valuable catalytic metal as salts are treated with alcohols, thereby separating, as esters, succinic and glutaric acids which would contaminate pure adipic acid on recycling, and allowing the re-use of the resulting stream containing nitric acid and metal catalytic salts.
    Type: Grant
    Filed: June 15, 1970
    Date of Patent: March 1, 1983
    Assignee: C. P. Hall Company
    Inventor: Vincent P. Kuceski
  • Patent number: 4337356
    Abstract: The continuous cobalt catalyzed liquid-phase oxidation of butane to acetic acid with oxygen has been improved by limiting the amount of iron, water and succinic acid present and maintaining a minimum of about 0.1% of cobalt acetate catalyst in the reaction medium.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: June 29, 1982
    Assignee: Union Carbide Corporation
    Inventors: John E. Logsdon, Ben W. Kiff
  • Patent number: 4332743
    Abstract: C.sub.1 to C.sub.3 mono-carboxylic acids, including a substantial proportion of acetic acid, are produced by oxidizing a paraffinic hydrocarbon feedstock with molecular oxygen at a temperature in the range 150.degree. to 250.degree. C. and at an elevated pressure sufficient to maintain the reactants in the liquid phase in the presence as catalyst, of phosphoric acid and/or a phosphate of one or more metals of Groups I and II of the Periodic Table, in particular sodium or potassium. In an alternative embodiment of the invention a co-catalyst in the form of one or more metals of variable valency, particularly manganese, is incorporated in the reactants. The reaction products are recovered by distillation.
    Type: Grant
    Filed: January 24, 1979
    Date of Patent: June 1, 1982
    Assignee: BP Chemicals Limited
    Inventors: Clive G. Gasser, John Russell
  • Patent number: 4328365
    Abstract: The present invention provides a supported catalyst for use in a vapor phase reaction for the high yield conversion of lower aliphatic hydrocarbons such as butane to corresponding monocarboxylic acids such as acetic acid. The catalyst is prepared by the carbon monoxide reduction of a vanadium pentoxide-impregnated, inert porous carrier.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: May 4, 1982
    Assignee: Celanese Corporation
    Inventors: William E. Slinkard, Anthony B. Baylis
  • Patent number: 4312714
    Abstract: The oxidation of liquid n-butane with oxygen gas at a temperature of from 120.degree. C. up to 235.degree. C. in the presence of an acetic acid solution containing bromide ion in combination with ions of cobalt or cobalt and manganese produces a reaction effluent containing mainly acetic acid (65 to 72 weight percent) and water (23 to 27 weight percent) together with impurity concentrations of esters and ketones boiling lower than acetic acid, higher carbon (C.sub.3 and C.sub.4) aliphatic monocarboxylic acids boiling higher than acetic acid and the difficultly separable 3-bromo-2-butanone impurity. The concentration of said bromoketone can be decreased by maintaining said reaction effluent or its debutanized residue at a temperature of from 150.degree. C. up to 200.degree. C. for 15 to 150 minutes. Subsequent distillation even further decreases the concentration of the bromoketone in the acetic acid distillate fraction.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: January 26, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventor: Jon J. Harper
  • Patent number: 4278503
    Abstract: Excessive energy consumption of a combination of multi-fractionations and multi-distillations of concentrating aqueous acetic acid product of liquid phase oxidations, especially oxidation of liquid n-butane with oxygen gas while the butane is dissolved in liquid acetic acid containing a catalyst system comprising Co-Br or Co-Mn-Br, is avoided and an otherwise hard to remove bromo-ketone is readily removed by a combination of sequential steps of decompressing the oxidation reaction mixture to remove unreacted butane as well as gaseous products, heat treating the decompressed liquid at a temperature of from 150.degree. C. up to 200.degree. C. for from 15 up to 150 minutes, subjecting the heat treated liquid to fractionation while recycling to the rectification zone thereof an aqueous portion of low boiling impurities as a means for concentrating the acetic acid and thereafter further concentrating the acetic acid produced by continuous fractional crystallization.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: July 14, 1981
    Assignee: Standard Oil Company (Indiana)
    Inventors: Martin A. Zeitlin, Jon J. Harper
  • Patent number: 4260822
    Abstract: A process for the direct oxidation of isobutane or propane to methacrylic acid or acrylic acid respectively is disclosed. The process encompasses contacting a feed gas containing isobutane or propane and oxygen with a specific catalyst which is composed of molybdenum, antimony and phosphorus combined with oxygen. The atomic ratio of molybdenum to antimony to phosphorous is from about 9 to about 24; about 0.25 to about 2; and about 0.75 to about 2 respectively. The catalytic oxidation to methacrylic or acrylic acid is accomplished at a temperature of from about 200.degree. C. to about 450.degree. C. The methacrylic or acrylic acid is removed from the feed gases exiting from the reaction zone and the remainder of the exited feed stream may be recycled to again contact the catalyst.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: April 7, 1981
    Assignee: Rohm and Haas Company
    Inventors: Harold Krieger, Lawrence S. Kirch
  • Patent number: 4259246
    Abstract: A process for producing maleic anhydride from a C.sub.4 hydrocarbon selected from n-butane and n-butene feed which comprises: (a) feeding the C.sub.4 hydrocarbon and air to a reactor; (b) contacting the C.sub.4 hydrocarbon and air in the reactor with a catalyst comprising vanadium and phosphorus oxides at reaction conditions including a temperature between 550.degree. and 1000.degree. F. so as to obtain a reactor effluent containing maleic anhydride, unreacted butane, nitrogen, oxygen, and acrylic, acetic or maleic acid or mixtures of the foregoing acids; (c) removing maleic anhydride from the reactor effluent to obtain maleic anhydride-lean effluent; (d) removing said acids from at least a portion of the maleic anhydride-lean effluent to obtain a purified recycle stream containing less than 100 ppm of the acids; and (e) recycling the purified stream to the reactor. Preferably the acids are removed in step (d) by water and/or caustic scrubbing the maleic anhydride-lean effluent.
    Type: Grant
    Filed: October 15, 1979
    Date of Patent: March 31, 1981
    Assignee: Chevron Research Company
    Inventors: Kiran R. Bakshi, David M. Marquis, Stephen G. Paradis
  • Patent number: 4230887
    Abstract: C.sub.2 -C.sub.6 monocarboxylic and dicarboxylic acids are scrubbed from gas phase mixtures of such acids and water by gas absorption techniques utilizing a liquid solvent comprising a polyoxyalkylene glycol or a monoalkyl or dialkyl ether thereof. The solvent enriched with the acid is subjected to distillation to recover a substantially anhydrous acid product.
    Type: Grant
    Filed: February 16, 1978
    Date of Patent: October 28, 1980
    Assignee: Celanese Corporation
    Inventors: William T. Mitchell, Phillip S. Snyder
  • Patent number: 4227971
    Abstract: Concentrated acetic acid of 95 to 100 weight percent concentration containing both ionic and coordinate bromine can be successfully purified to a bromine content of less than 3 ppm by the sequential steps of catalytic hydrogenation, contacting the resulting acetic acid with alkali metal hydroxide, carbonate or bicarbonate, and then distilling acetic acid from the alkali metal.
    Type: Grant
    Filed: December 18, 1978
    Date of Patent: October 14, 1980
    Assignee: Standard Oil Company (Indiana)
    Inventor: Wilford J. Zimmerschied