Organic Hydroxy Containing Reactant Patents (Class 568/471)
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Patent number: 4987252Abstract: In order to recover methacrolein and/or methacrylic acid by quenching a reaction product gas obtained by catalytic oxidation of isobutylene or the like, the reaction product gas is charged into a quench column through a double-wall pipe and is then brought into contact with a condensate as a cooling medium. Deposition of terephthalic acid and the like inside the column is prevented by controlling the temperature of a bottom in the quench column and that of an overhead gas of a quench column unit. An aromatic carboxylic acid, aromatic aldehyde, metal powder is added to an aqueous solution of methacrylic acid, which contains terephthalic acid and the like, so that the terephthalic acid and the like are caused to precipitate for their removal.Type: GrantFiled: June 27, 1988Date of Patent: January 22, 1991Assignees: Mitsui Toatsu Chemicals, Incorporated, Kyowa Gas Chemical Industry Co., Ltd.Inventors: Morimasa Kuragano, Kozo Iwasaki, Takeshi Isobe, Isao Fukada, Minoru Koshibe, Yoshihiro Sezaki, Hirozo Segawa, Katsuji Yoguchi
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Patent number: 4978803Abstract: In the process for making glyoxal by catalytic oxidation of ethylene glycol in contact with catalyst comprising copper, glyoxal yield is improved and catalyst life is improved by the presence of a small amount of iodine or organic iodide in the reactant feed mixture.Type: GrantFiled: June 26, 1989Date of Patent: December 18, 1990Assignee: American Cyanamid CompanyInventor: Roger J. Card
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Patent number: 4959494Abstract: A method for oxidizing organic compounds by contacting organic compounds with molecular oxygen in the presence of a noble metal pyrochlore having the formula:A.sub.2+x B.sub.2-x O.sub.7-ywherein A is a pyrochlore structure metal cation, and B is one or more of Ru, Rh, Ir, Os, and Pt; x and y are greater than or equal to 0 and less than or equal to 1.0, at a temperature up to about 200.degree. C.Type: GrantFiled: July 6, 1987Date of Patent: September 25, 1990Assignee: Monsanto CompanyInventor: Timothy R. Felthouse
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Patent number: 4929763Abstract: Conversion of alcohol to organic compounds which comprises contacting the alcohol with a heterogeneous catalyst composition comprising at least one member selected from the group consisting of(a) crystalline LnAl.sub.1.67+0.67X (B.sub.4 O.sub.10)O.sub.X, and(b) crystalline LnAl.sub.2.67+0.33Z (B.sub.4 O.sub.11)O.sub.Zwhere Ln is at least one transition element selected from the group consisting of Group IIIB of the Periodic Table, X is a number ranging from 0 to 1, and Z is a number ranging from 0 to 2, each crystalline phase having a characteristic X-ray diffraction pattern.Type: GrantFiled: March 29, 1989Date of Patent: May 29, 1990Assignee: Amoco CorporationInventors: Melvin L. Luetkens, Jr., Steve T. McKenna, John L. Melquist
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Patent number: 4929768Abstract: A process for preparing a dialdehyde which comprises subjecting a glycol to oxidation-dehydrogenation in the presence of silver particles of which the surface is partially coated with a silicon carbide powder or a silicon nitride powder. According to the present invention, dialdehydes can be prepared from glycols in high conversion of the glycol in high selectivity into the dialdehyde, and the silver catalyst can be reused even if the reaction is stopped in a while since the silver particles are not aggregated during long time operation.Type: GrantFiled: February 16, 1989Date of Patent: May 29, 1990Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki KaishaInventors: Sumio Nakagawa, Masaoki Toiyama, Yoshinobu Uno, Hiromichi Kohda
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Patent number: 4871700Abstract: A method of reactivating a catalyst having reduced activity as a result of having been used in producing an unsaturated aldehyde as a main product by catalytic vapor-phase oxidation reaction of propylene, isobutylene or tertiary butanol, said catalyst being a catalytic oxide comprising molybdenum, bismuth and iron with a Mo:Fe atomic ratio of 12:at least 0.1. The method comprises heat-treating the used catalyst at a temperature of 300.degree. to 500.degree. C. in the presence of a flowing oxidizing gas containing at least 5% by volume of molecular oxygen and at least 0.1% by volume of steam.Type: GrantFiled: May 12, 1988Date of Patent: October 3, 1989Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Shin-ichi Uchida, Kozi Deguchi, Masamitsu Sasaki
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Patent number: 4851584Abstract: A process for the preparation of carbonyl compounds by oxidation of alcohols in the gas phase with a gas containing oxygen in the presence of catalysts containing copper and silver.Type: GrantFiled: March 30, 1988Date of Patent: July 25, 1989Assignee: BASF AktiengesellschaftInventors: Fritz Graf, Leopold Hupfer, Harald Schultheiss
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Patent number: 4843178Abstract: The present invention relates to a process for producing an E,Z-9-alkenyl-1-aldehyde component which comprises:(a) disproportionating cyclooctene and an .alpha.-olefin in the presence of a suitable disproportionation catalyst under disproportionation conditions suitable to form a 1,9-alkadiene;(b) reacting the 1,9-alkadiene obtained in step (a) with a suitable metallating agent under conditions suitable to form a 1-metallo-9-alkene;(c) contacting the 1-metallo-9-alkene obtained in step (b) with oxygen under conditions suitable to form a 1-oxymetallo-9-alkene;(d) hydrolyzing the 1-oxymetallo-9-alkene suit a suitable hydrolyzing agent, under suitable hydrolyzing conditions to form E,Z-9-alkenyl-1-alcohol.(e) oxidizing said E,Z-9-alkenyl-1-alcohol with a suitable oxidizing agent under oxidizing conditions suitable to form E,Z-9-alkenyl-1-aldehyde.Type: GrantFiled: December 2, 1987Date of Patent: June 27, 1989Inventors: Jim D. Byers, Charles A. Drake
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Patent number: 4820875Abstract: In a process for vapour-phase synthesis of carbonyl compounds from alcohols a mixture of the alcohol and air or oxygen is passed over a silver catalyst. The concentration of alcohol:air or alcohol:oxygen is below the explosive limits. The process is conducted as a temperature between 200.degree. and 450.degree. C. Previously the production of carbonyl compounds required a temperature of 450.degree.-700.degree. C. which necessitated the use of heat exchangers using fused salt baths. The silver catalyst may be supported.Type: GrantFiled: December 23, 1987Date of Patent: April 11, 1989Assignee: Johnson Matthey Public Limited CompanyInventors: Dennis E. Webster, Phillip J. Player
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Patent number: 4816603Abstract: The present invention provides a process for the production of methacrolein and methacrylic acid by the gas phase catalytic oxidation of isobutylene or t-butanol at high temperature using molecular oxygen in the presence of catalyst consisting of molybdenum, tungsten, bismuth, iron, nickel, antimony, and an alkali metal, to which zinc or lead is added, and further phosphorus sulfur, silicon, selenium, germanium or boron, and magnesium, cobalt, manganese or tin are added.Type: GrantFiled: November 26, 1985Date of Patent: March 28, 1989Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Motomu Oh-Kita, Yoshiyuki Taniguchi, Masaaki Kato, Masao Kobayashi
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Patent number: 4816606Abstract: Aldehydes and ketones of the general formula I ##STR1## where R.sup.1 is hydrogen or an organic radical of 1 to n carbon atoms and R.sup.2 is a non-aromatic organic radical of 1 to m carbon atoms, (m+n) ranging from 2 to 24 and R.sup.1 and R.sup.2 being combinable to form a 4- to 12-membered ring, are prepared in a continuous manner by oxidizing an alcohol of the general formula II ##STR2## with oxygen or an oxygen-containing gas at elevated temperatures in the gas phase in the presence of a catalyst, by effecting the oxidation by means of a supported catalyst composed of an inert carrier having a smooth surface and from 0.1 to 20% by weight, based on the amount of carrier, of an active layer of copper, silver and/or gold in a tubular reactor or tube bundle reactor where the internal diameter D of the tube or tubes ranges from 10 to 50 mm and the largest diameter d of the coated supported catalysts is subject to the relationship d=from 0.1 to 0.2 D.Type: GrantFiled: September 30, 1987Date of Patent: March 28, 1989Assignee: Basf AktiengesellschaftInventors: Karl Brenner, Manfred Eggersdorfer, Wilhelm Ruppel, Harald Schultheiss, Hans-Ulrich Scholz
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Patent number: 4814513Abstract: A process for the preparation of carbonyl compounds by oxidation of alcohols in the gas phase with a gas containing oxygen in the presence of catalysts containing copper or silver and a phosphorus compound that is volatile under the conditions of the reaction, the ratio of the mass of phosphorus to the mass of the alcohol being less than 0.5 ppm.Type: GrantFiled: December 9, 1987Date of Patent: March 21, 1989Assignee: BASF AktiengesellschaftInventors: Fritz Graf, Heinz Engelbach, Leopold Hupfer, Harald Schultheiss, Michael J. Sprague
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Patent number: 4740627Abstract: The present invention pertains to a process for making a E,Z-11-tetradecen-1-al containing from 80 to 83 mole percent of the E isomer and from 17 to 20 mole percent of the Z isomer which exhibits pheromone-like activity for the spruce bud worm (choristoneura fumiferana).Type: GrantFiled: May 21, 1987Date of Patent: April 26, 1988Assignee: Phillips Petroleum CompanyInventors: Jim D. Byers, Charles A. Drake
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Patent number: 4691053Abstract: A novel process for producing oxygen-containing organic compounds with high selectivity and good yield by oxidizing organic compounds under mild conditions is provided, which process comprises using as a catalyst for the oxidation, a complex (M.sub.m X.sub.n.L.sub.l) consisting of a transition metal compound (M.sub.m X.sub.n) and an organic phosphorous compound (L) as a ligand, wherein M represents a transition metal belonging to group I, group IV.about.VII or iron group in group VIII of the periodic table; X represents an anion such as a halogen; ligand L represents an organic phosphorous compound; and m and n mean a number of the atomic valence of said transition metal (ion) M and said anion X, respectively, and l means a number of said ligand.Type: GrantFiled: June 4, 1984Date of Patent: September 1, 1987Assignee: Babcock-Hitachi Kabushiki KaishaInventors: Mutsuo Yamada, Yasuyuki Nishimura, Yoshijiro Arikawa, Takanori Kuwahara, Taiji Kamiguchi, Hirotoshi Tanimoto
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Patent number: 4691060Abstract: Waste heat possessed by a hot formaldehyde product gas obtained by catalytic reaction of methanol with air is heat exchanged with pressurized water in a waste heat boiler, thereby generating steam, and then leading the product gas to a formaldehyde absorption column, thereby absorbing formaldehyde, into an aqueous solution, and heat exchanging a recycling solution for a feed gas humidifier with the aqueous solution withdrawn from the bottom of absorption column. The waste heat can be efficiently recovered without deposition of paraformaldehyde on the heat transfer surface of heat exchanger and the amount of additional steam can be reduced or made entirely zero.Type: GrantFiled: November 25, 1986Date of Patent: September 1, 1987Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shigeo Kimura, Kouichi Kurata
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Patent number: 4618709Abstract: A process for separation of methacrylic acid from a methacrylic acid-containing, gaseous reaction mixture obtained by subjecting methacrolein or a compound which can afford methacrolein under reaction conditions and molecular oxygen to gas phase reaction in the presence of a catalyst for oxidation under the coexistence of an inert gas for dilution which comprises (a) cooling the gaseous reaction mixture from a reactor wherein the gas phase reaction has been effected to separate into condensable components including methacrylic acid, acetic acid and water vapor as a condensed liquor and non-condensable components including methacrolein as a non-condensed gaseous mixture, (b) eliminating contaminating methacrolein from the condensed liquor and (c) contacting the resulting condensed liquor with an organic solvent to extract methacrylic acid, followed by separation into an organic solvent solution including methacrylic acid and an aqueous solution as waste water, characterized in that (1) the inert gas for dilutiType: GrantFiled: January 30, 1981Date of Patent: October 21, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Masao Sada, Michio Kato, Masami Ayano, Tadashi Abe, Masanori Moriwaki
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Patent number: 4599459Abstract: A method for the ultrasonic treatment of dilute alcoholic solution in which a vibrator member placed in a dilute alcoholic solution is subjected to ultrasonic vibrations to produce cavitation in the solution in such a way that alcohol in the solution is vaporized and collected in a high concentration. The alcohol may be readily converted into a corresponding aldehyde.Type: GrantFiled: August 31, 1984Date of Patent: July 8, 1986Inventor: Masanao Hirose
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Agent facilitating liposome cellular wall transport, a method for the production thereof and its use
Patent number: 4590060Abstract: An agent is described in which contains an aldehyde of formula IRCHO (I)in which R is a hydrogen atom, a straight-chain or branched hydrocarbon group having 1 to 4 carbon atoms, and preferably an alcohol of formula IIR'CH.sub.2 OH (II)in which R' has the meaning indicated above. The agent is used together with charged liposomes. By the administration of the agent, the permeability of the liposomes through tissue cell walls is substantially improved and tagged liposomes accumulate around and in a malignant tumor. A kit for use in diagnosis and therapy is also described.Type: GrantFiled: December 2, 1983Date of Patent: May 20, 1986Inventor: Udo Ehrenfeld -
Patent number: 4564703Abstract: In a process for preparing methacrylic acid by the vapor-phase catalytic oxidation of methacrolein or a methacrolein-containing mixture with molecular oxygen in the presence of an oxidation catalyst; the improvement wherein said process comprisesa first-stage oxidation step of oxidizing methacrolein or a methacrolein-containing mixture as a starting material,a first-stage separating step of separating the resulting methacrylic acid from the reaction product obtained in the first-stage oxidation step,a second-stage oxidation step of oxidizing the mixture containing the unreacted methacrolein and obtained in the first-stage separating step, anda second-stage separating step of separating the resulting methacrylic acid from the reaction product obtained in the second-stage oxidation step, andwith or without at least one additional oxidation step and separating step subsequent to the second-stage separating step,and wherein the conversion of methacrolein in the first-stage oxidation step is adjusted to 30-85 moleType: GrantFiled: April 16, 1979Date of Patent: January 14, 1986Assignee: Nippon Zeon Co., Ltd.Inventors: Haruhisa Yamamoto, Shinichi Akiyama
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Patent number: 4555583Abstract: Glyoxal may be produced with a high yield by bringing a gas, which has been formed by diluting ethylene glycol and molecular oxygen with an inert gas, into contact at a high temperature with a silver catalyst in the simultaneous presence of phosphorus or a phosphorus compound so as to effect the gas phase oxidation of the ethylene glycol.In the above process, it is possible to suppress the formation of glycolaldehyde, a reaction intermediate, and also to enhance the stability of the reaction by using silver powder having particle sizes of 1.times.10.sup.-3 mm or smaller as at least part of the silver catalyst.Type: GrantFiled: March 28, 1984Date of Patent: November 26, 1985Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yoshiaki Toyoda, Kazuo Wakimura, Tadaharu Hase, Nobumasa Arashiba
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Patent number: 4521395Abstract: A process for the ammoxidation of methanol or formaldehyde to hydrogen cyanide or oxidation of methanol to formaldehyde using a catalyst comprising boron and phosphorus oxides, wherein the boron to phosphorus atomic ratio is 0.8:1 to 1.25:1.Type: GrantFiled: November 18, 1983Date of Patent: June 4, 1985Assignee: Monsanto CompanyInventors: Thomas C. Kuechler, Jerry R. Ebner, Tao P. Li
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Patent number: 4511739Abstract: Glyoxal is prepared by oxidizing glycol in the presence of a silver catalyst, with subsequent or partial condensation of glycol, glyoxal, glycol aldehyde, formaldehyde and/or water by treatment with water or aqueous glyoxal solution in fine dispersion, under specific conditions with regard to the temperature and dispersion of the treatment liquid.The glyoxal which can be prepared by the process of the invention is a wrinkle-resist agent, an assistant for increasing the tear strength and elasticity of fiber materials, a tanning agent, a photographic hardener and a valuable starting material for the production of synthetic resins, textile assistants, paper assistants and plastics.Type: GrantFiled: May 27, 1980Date of Patent: April 16, 1985Assignee: BASF AktiengesellschaftInventors: Wolfgang Sauer, Wolfgang Hoffmann
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Patent number: 4503261Abstract: A process for the continuous preparation of glyoxal by oxidation of ethylene glycol, in which the ethylene glycol, oxygen and an inert gas are passed, at from 450.degree. to 800.degree. C., over a catalyst consisting of one or more layers of copper crystals and one or more layers of silver crystals, the copper and silver crystals having a particle size of from 0.1 to 2.5 mm.Type: GrantFiled: July 22, 1982Date of Patent: March 5, 1985Assignee: BASF AktiengesellschaftInventors: Wolfgang Sauer, Klaus Halbritter, Heinz Engelbach
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Patent number: 4478743Abstract: Described is a compound having the structure: ##STR1## a norbornyl oxyacetaldehyde, prepared by oxidizing the norbornyl oxyethanol compound having the structure: ##STR2## using air or oxygen and a silver or copper chromite catalyst; and organoleptic uses of such oxidation product in the field of perfumery, colognes and perfumed articles (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: February 23, 1984Date of Patent: October 23, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Robert P. Belko, Richard M. Boden, Marie R. Hanna
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Patent number: 4474996Abstract: Methanol is converted to formaldehyde by oxidative dehydrogenation using as catalyst sputtered or ion plated silver or silver/gold alloy on an inert hard, nonporous support.Type: GrantFiled: March 14, 1983Date of Patent: October 2, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventors: Peter F. Carcia, Velliyur Nott M. Rao
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Patent number: 4471141Abstract: Aqueous alcoholic solutions such as hydrous alkanols may be converted to the corresponding aldehyde in a process which involves high conversion levels and high selectivity levels by treating the solution with an oxygen-containing gas in the presence of a catalyst comprising at least two oxides of metals selected from the group consisting of molybdenum, tungsten, cobalt, nickel, manganese, iron and chromium, one of said oxides being molybdenum oxide or tungsten oxide composited on a high surface area support. Reaction conditions which are employed in the process will include temperatures in the range of from about 200.degree. to about 400.degree. C. and a pressure in the range of from about atmospheric to about 50 atmospheres.Type: GrantFiled: February 22, 1983Date of Patent: September 11, 1984Assignee: UOP Inc.Inventors: Hassan Windawi, Warren R. Oakdale
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Patent number: 4450301Abstract: In a process for oxidizing methanol to formaldehyde which comprises passing the methanol with molecular oxygen through two sequential silver-based catalysts, with the second of said catalysts being a bed of particulate silver such as, specifically, silver crystals, the process efficiency, and especially the efficiency of the reaction taking place in the second catalyst bed, is improved by controlling (a) the ratio of formaldehyde to methanol in the reactant gases entering the second catalyst bed and (b) the specific reaction rate in said second bed. The specific reaction rate is defined as the quantity of methanol converted in said second bed per unit time per unit of cross-sectional area of the bed.Type: GrantFiled: October 21, 1982Date of Patent: May 22, 1984Assignee: Celanese CorporationInventors: William P. McMillan, Charles C. Hobbs, Jr., H. Robert Gerberich, Michael L. Junker
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Patent number: 4446328Abstract: A process for producing methacrolein by oxidizing isobutylene or tertiary butanol with molecular oxygen, characterized by contacting a gaseous mixture of isobutylene or tertiary butanol, air or oxygen and optionally steam and an inert gas with a catalyst having the general composition:Mo.sub.12 Fe.sub.a Ni.sub.b Te.sub.c X.sub.d Z.sub.f Y.sub.g O.sub.hwherein a, b, c, d, f and g represent the numbers of atoms of the respective elements per 12 molybdenum atoms; X is Tl, Rb or Cs; Z is In or Ti; Y represents at least one element selected from the group consisting of Cu, Nd, Sm and Pb; a is a value of 0.2-6; b is a value of 0.2-6; a+b is a value of 1-10; c is a value of 0.1-4; d is a value of 0.1-3; f is a value of 0.1-3; g is a value of 0-5; and h is the number of oxygen atoms for satisfying the valencies of the existing elements. The use of this catalyst enables the selectivity for methacrolein to be improved to 90 or more and the yield based on the starting material to be increased to 89-91%.Type: GrantFiled: May 14, 1981Date of Patent: May 1, 1984Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Ryoichi Mitsui
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Patent number: 4442307Abstract: A process is disclosed for oxidizing dimethyl ether to formaldehyde using a catalyst comprising a mixture of oxides of bismuth, molybdenum and iron.Type: GrantFiled: October 7, 1982Date of Patent: April 10, 1984Assignee: Shell Oil CompanyInventors: Robert M. Lewis, Robert C. Ryan, Lynn H. Slaugh
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Patent number: 4440960Abstract: A process for the continuous preparation of 3-alkyl-buten-1-als by oxidative dehydrogenation of 3-alkyl-buten-1-ols at from 320.degree. to 650.degree. C. with oxygen over a catalyst containing copper and/or silver, wherein, within one second after contact with the catalyst, the vaporous reaction mixture, which is at from 320.degree. to 650.degree. C., is brought into contact with a liquid comprising water and/or the condensed reaction mixture at from -20.degree. to 50.degree. C., and the 3-alkyl-buten-1-als are separated off from the resulting condensate.Type: GrantFiled: December 11, 1981Date of Patent: April 3, 1984Assignee: BASF AktiengesellschaftInventors: Wolfgang Sauer, Werner Aquila, Wolfgang Hoffmann, Karl Brenner, Klaus Halbritter
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Patent number: 4439624Abstract: A process is disclosed for oxidizing dimethyl ether to formaldehyde using a catlyst comprising a mixture of oxides of bismuth, molybdenum and copper.Type: GrantFiled: October 7, 1982Date of Patent: March 27, 1984Assignee: Shell Oil CompanyInventors: Robert M. Lewis, Robert C. Ryan, Lynn H. Slaugh
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Patent number: 4439625Abstract: A process for converting methanol to formaldehyde at 450.degree. to 750.degree. C. using as catalyst silver, silver-gold alloys or copper-gold alloys in which from 0.001 to 15 parts per million, based on methanol, of phosphorus or phosphorus from a phosphorus compound is present.Type: GrantFiled: September 29, 1982Date of Patent: March 27, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Velliyur Nott M. Rao
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Patent number: 4433175Abstract: For the production of neohexanol with a purity above 99%, a chlorine content of less than 10 ppm, and a sulfur content of less than 5 ppm, 3,3-dimethylbutyric acid with a chlorine content below 650 ppm, preferably below 100 ppm, is first esterified, optionally after distillatory separation into a portion richer in chlorine with a chlorine content above 650 ppm, preferably above 100 ppm, and into a portion low in chlorine with a chlorine content below 650 ppm, preferably below 100, with an alcohol boiling above 117.degree. C., preferably an octyl alcohol. The resultant ester is separated by distillation into fractions richer in chlorine with chlorine contents above 10 ppm and into fractions low in chlorine with chlorine contents below 10 ppm. The ester of low chlorine contents below 10 ppm is hydrogenated to neohexanol over a barium-activated copper chromite catalyst under a pressure of 200-300 bar, at 120.degree.-22.degree. C., and with catalyst loads of 0.05-1.Type: GrantFiled: November 24, 1982Date of Patent: February 21, 1984Assignee: Chemische Werke Huels, A.G.Inventor: Manfred Kaufhold
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Patent number: 4421938Abstract: Alcohols such as those containing from about 1 to about 10 carbon atoms may be converted to aldehydes by treating the alcohols with an oxygen-containing gas such as air or oxygen in the presence of a catalyst comprising at least two oxides of metals selected from the group consisting of molybdenum, tungsten, cobalt, nickel, manganese, iron and chromium, at least one of said oxides being molybdenum oxide or tungsten oxide composited on a high surface area support. The conversion reaction may be effected at a temperature ranging from about 200.degree. to about 400.degree. C. and a pressure in the range of from about atmospheric to about 50 atmospheres. By employing this particular catalyst, good conversion rates and high selectivity to the aldehydes will be obtained.Type: GrantFiled: April 5, 1982Date of Patent: December 20, 1983Assignee: UOP Inc.Inventor: Hassan Windawi
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Patent number: 4420641Abstract: New catalysts comprising lead and silver on supports having relatively low surface areas and their use have been found to be useful in the oxidative dehydrogenation of methanol to formaldehyde at elevated temperatures.Type: GrantFiled: January 12, 1983Date of Patent: December 13, 1983Assignee: Celanese CorporationInventors: H. Robert Gerberich, Eldred T. Smith
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Patent number: 4404397Abstract: A stabilized heteropoly molybdate catalyst precursor in calcined form and containing anionic molybdenum in defect state is surface impregnated with certain metal cations. The stabilized precursor is one obtained by incorporating into the reaction product of a molybdate and a soluble phosphate, silicate or arsenate, an aqueous chloride ion and a compound of phosphotungstate, silicotungstate, vanadium arsenate, silico-arsenate, phosphovanadate, or silicovanadate, followed by drying and calcining. During the chloride ion stabilization step other metals may be optionally incorporated in forming the stabilized precursor.The obtained precursor is catalytically active in the conversion of the unsaturated aldehydes to the corresponding unsaturated carboxylic acids with or without incorporation of the metal cation during the chloride ion stabilization step.Type: GrantFiled: December 29, 1980Date of Patent: September 13, 1983Assignee: Air Products and Chemicals, Inc.Inventor: Chelliah Daniel
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Patent number: 4380664Abstract: At least one olefinic hydrocarbon of 3 to 4 carbon atoms is oxidized catalytically in the gas phase in the presence of molecular oxygen at 200.degree.-450.degree. C. to produce the corresponding aldehyde and acid over a calcined catalyst of the formula Mo.sub.a Sb.sub.b Bi.sub.c Fe.sub.d Ni.sub.e Sn.sub.f X.sub.g Y.sub.h O.sub.i wherein X is at least one alkali metal selected from the group consisting of potassium, rubidium and cesium; Y is at least one metal selected from the group consisting of cobalt, uranium, germanium, tungsten and titanium; a to h are atomic ratios wherein a=12, b=0.2 to 20, c=0.2 to 12, d=0.2 to 12, e=0.2 to 12, f=0 to 20, g=0.01 to 4 and h=0 to 6; and i is determined according to the oxidation states of the metal atoms in the catalyst.Type: GrantFiled: March 29, 1978Date of Patent: April 19, 1983Assignee: Mitsubishi Rayon Company, Ltd.Inventors: Hiromichi Ishii, Hideo Matsuzawa, Masao Kobayashi, Kantaro Yamada
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Patent number: 4358623Abstract: In catalytically oxidizing methanol in the vapor phase according to already-known processes for the production of formaldehyde, the hot formaldehyde-containing gaseous effluent of the catalytic converter is rapidly cooled by being passed through the tubes of a heat exchanger which are filled with balls composed of a solid which is substantially inert toward formaldehyde. As compared with a similar cooling system in which the tubes are empty or in which enhancement of heat transfer is attempted by using metal heat-transfer enhancement devices such as twisted metal ribbons, the present method affords reduced post-reaction decomposition of formaldehyde while at the same time allowing use of a relatively high temperature on the shell side of the heat exchanger whereby it becomes possible to raise steam at a pressure higher than that characteristic of the prior art.Type: GrantFiled: July 23, 1981Date of Patent: November 9, 1982Assignee: Celanese CorporationInventors: Carl D. Murphy, William P. McMillan
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Patent number: 4355187Abstract: Methyl glyoxal is prepared by oxidation of propylene glycol-1,2 in the gaseous phase on a heterogeneous catalyst. The process is carried out with an excess of oxygen and the catalyst used contains molybdenum and at least one of the metals: vanadium, silver, copper, iron, tungsten, tin, zinc, alkali metals, alkaline earth metals.Type: GrantFiled: March 26, 1981Date of Patent: October 19, 1982Assignee: Hoechst AktiengesellschaftInventors: Herbert Baltes, Ernst I. Leupold
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Patent number: 4354043Abstract: Described is a compound having the structure: ##STR1## a norbornyl oxyacetaldehyde, prepared by oxidizing the norbornyl oxyethanol compound having the structure: ##STR2## using air or oxygen and a silver or copper chromite catalyst; and organoleptic uses of such oxidation product in the field of perfumery, colognes and perfumed articles (e.g. perfumed plastics, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or drier-added fabric softener articles).Type: GrantFiled: September 17, 1981Date of Patent: October 12, 1982Assignee: International Flavors & Fragrances Inc.Inventors: Robert P. Belko, Richard M. Boden, Marie R. Hanna
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Patent number: 4354044Abstract: A method for preparing methacrolein by oxidizing isobutylene or tertiary butanol with molecular oxygen, characterized by contacting a gaseous mixture of isobutylene or tertiary butanol, air or oxygen and optionally steam and an inert gas with a catalyst having the general combination:Mo.sub.12 Fe.sub.a Ni.sub.b Te.sub.c Tl.sub.d Pb.sub.f X.sub.g O.sub.hwherein a, b, c, d, f and g represent the numbers of atoms of the respective elements per 12 molybdenum atoms; X is at least one element selected from the group consisting of Cu, Nd and Sm; a is a value of 0.2-6; b is a value of 0.2-6; a+b is a value of 1-10; c is a value of 0.1-4; d is a value of 0.1-3; f is a value of 0.1-5; g is a value of 0.1-5; and h is the number of oxygen atoms for satisfying the valencies of the existing elements. The use of this catalyst enables the selectivity for methacrolein to be improved to 90-94% and the yield based on the starting material to be increased to 89-91%.Type: GrantFiled: May 20, 1981Date of Patent: October 12, 1982Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Ryoichi Mitsui, Hitoshi Nihei
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Patent number: 4323520Abstract: The present invention relates to a process for the conversion of tertiary-butyl-containing compounds to methacrylic derivatives, and more particularly to a process for the conversion of tertiary-butyl-containing compounds selected from the group consisting of alkyl tertiary-butyl ethers, tertiary-butyl alcohol, isobutylene dimer (2,2,4-trimethylpentene) and isobutylene trimer, to methacrolein, methacrylic acid or methacrylonitrile.Type: GrantFiled: May 9, 1977Date of Patent: April 6, 1982Assignee: The Standard Oil Co.Inventors: Harley F. Hardman, James L. Callahan, Robert K. Grasselli
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Patent number: 4306088Abstract: In the production of methacrolein by vapor phase catalytic oxidation of isobutylene and/or t-butyl alcohol, an improved process for suppressing the amount of acetone to be by-produced which comprises contacting a gaseous mixture comprising isobutylene or t-butyl alcohol, molecular oxygen and steam with a metal oxide catalyst composition comprising molybdenum and bismuth as the essential metal components, the amount of steam in the gaseous mixture being kept to be not more than 4 mol per mol of isobutylene or not more than 3 mol per mol of t-butyl alcohol.Type: GrantFiled: June 25, 1980Date of Patent: December 15, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Shuzo Nakamura, Hiroshi Ichihashi, Yoshihiko Nagaoka, Koichi Nagai
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Patent number: 4302609Abstract: Methylglyoxal is manufactured continuously by passing glycerol in the gaseous phase over a heterogeneous dehydrogenation catalyst.Type: GrantFiled: July 3, 1980Date of Patent: November 24, 1981Assignee: Hoechst AktiengesellschaftInventors: Herbert Baltes, Ernst I. Leupold
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Patent number: 4282374Abstract: A process for the preparation of glyoxal by vapor phase oxidation of ethylene glycol with oxygen over a copper-containing oxidation catalyst at an elevated temperature and in the presence of a phosphorus compound which is volatile under the reaction conditions, the amount of phosphorus (calculated as P) being from 1 to 100 ppm, based on the weight of ethylene glycol.Type: GrantFiled: July 5, 1979Date of Patent: August 4, 1981Assignee: BASF AktiengesellschaftInventors: Heinz Engelbach, Michael J. Sprague
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Patent number: 4258216Abstract: The process for preparing glyoxal from ethylene glycol wherein a gaseous mixture of ethylene glycol, oxygen, and inert diluent gas is reacted in the presence of a catalyst containing as essential ingredients phosphorous with copper, with silver, or with both copper and silver, to form glyoxal, is improved by incorporating in said gaseous mixture a vapor of a bromine compound.Type: GrantFiled: April 9, 1979Date of Patent: March 24, 1981Assignee: American Cyanamid CompanyInventors: James B. Trecek, George L. Wiesner
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Patent number: 4250339Abstract: Methacrolein is produced by a vapor phase oxidation of isobutylene or tertiary butanol in the presence of a complex oxide catalyst having the formulaMo.sub.a Co.sub.b Fe.sub.c Bi.sub.d Tl.sub.e X.sub.f Y.sub.g Z.sub.h O.sub.iwherein X represents V and/or Nb; Y represents La and/or Ce; and Z represents Cs and/or Te and a, b, c, d, e, f, g, h and i represent atomic ratios wherein a=12; b=3 to 15; c=0.4 to 5; d=0.4 to 5; e=0.01 to 2; f=0.01 to 2; g=0 to 2; h=0 to 2; and i is determined by the valences of the non-oxygen components of the catalyst and is usually in a range of 40 to 79.Type: GrantFiled: November 30, 1979Date of Patent: February 10, 1981Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Teruhisa Sakamoto, Kazuhiko Sekizawa, Keiichi Kihara
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Patent number: 4250121Abstract: Carbonyl compounds are manufactured by oxidizing alcohols or polyalcohols with molecular oxygen in the presence of a catalyst which comprises ruthenium salts or complexes associated with copper or iron salts or complexes.Type: GrantFiled: May 24, 1979Date of Patent: February 10, 1981Assignee: Institut Francais du PetroleInventor: Hubert Mimoun
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Patent number: 4242282Abstract: Glyoxal is prepared by oxidizing glycol in the presence of a silver catalyst of a defined particle size and under defined conditions of temperature, residence time and inert gas concentration.The glyoxal obtainable by the process of the invention may be used in wrinkle-resist finishing, as an assistant for increasing the tensile strength and resilience of fibrous materials, a tanning agent, a hardener in the photographic industry, and a starting material for the manufacture of synthetic resins, textile auxiliaries, for example to prevent shrinkage after washing, paper additives, for example for increasing the wet strength, and plastics.Type: GrantFiled: January 10, 1979Date of Patent: December 30, 1980Assignee: BASF AktiengesellschaftInventors: Hans Diem, Christian Dudeck, Gunter Lehmann, Guenther Matthias, Norbert Petri
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Patent number: 4233246Abstract: Aliphatic hydroxycarbonyl compounds etherified with aliphatic groups are prepared by oxidizing hydroxyalcohols in the presence of a metal catalyst which consists of one or more layers, each of a particular weight and each containing particles of a particular size, the catalyst bed also having a particular total thickness, and the catalyst components used being silver and copper, with or without added copper/tin/phosphorus or silver alone. The etherified hydroxyaldehydes and hydroxyketones obtainable by the process of the invention are valuable starting materials for the preparation of dyes, pesticides, plastics and scents.Type: GrantFiled: December 20, 1978Date of Patent: November 11, 1980Assignee: BASF AktiengesellschaftInventors: Christian Dudeck, Gunter Lehmann, Norbert Petri, Hans Diem, Werner Fliege, Bernd Meissner, Karl-Heinz Ross, Wolfgang Muehlthaler