Patents Represented by Attorney Gary R. Plotecher
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Patent number: 4319066Abstract: Cyclohexenyl and alkenyl aromatic compounds, such as cyclohexene and styrene, are prepared by a process comprising contacting a corresponding cyclohexyl or alkyl aromatic carboxylic acid, such as cyclohexyl carboxylic acid or 2-phenyl propionic acid, with a decarboxylation catalyst of the formulaM.sub.a M'.sub.b O.sub.xwhereM is copper or a combination of copper and molybdenum, andM' is at least one promoter element, such as a Group IA element.Type: GrantFiled: August 1, 1980Date of Patent: March 9, 1982Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Serge R. Dolhyj, Andrew S. Krupa
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Patent number: 4314075Abstract: Olefinic acids and esters, such as methacrylic acid and methylmethacrylate, are prepared by contacting in the presence of molecular oxygen the corresponding saturated acid or ester, such as isobutyric acid or methylisobutyrate with the catalyst of the empirical formula:Mo.sub.12 P.sub.0.1-3 M.sub.0.1-3 Cu.sub.0.01-2 V.sub.0.01-2 X.sub.0.01-2 M'.sub.a O.sub.b (I)whereM is at least one of K, Rb and Cs;X is at least one of Ba, La, Ga, Al, Ag, Cd, Ti, Tl, Hg, Pb and Zn;M' is at least one of Fe, Co, Ni, Sr, Mn, In, Ta, Ge, S and Be when a >0;a is a number of 0 to about 2; andb is a number that satisfies the valence requirements of the other elements present.Type: GrantFiled: September 5, 1980Date of Patent: February 2, 1982Assignee: The Standard Oil CompanyInventors: Wilfrid G. Shaw, Philip L. Kuch, Christos Paparizos
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Patent number: 4309310Abstract: Olefins, such as propylene, are allylically oxidized to corresponding unsaturated aldehydes and carboxylic acids, such as acrolein and acrylic acid, by contacting the olefin with molecular oxygen at allylic oxidation conditions in the presence of a trifluoroalkyl sulfonate or phosphonate catalyst, such as a catalyst formed by the reaction of vanadyl oxide and trifluoromethyl sulfonate.Type: GrantFiled: March 31, 1980Date of Patent: January 5, 1982Assignee: Standard Oil CompanyInventor: James L. Callahan
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Patent number: 4307247Abstract: Saturated, lower aliphatic acids and esters are oxydehydrogenated to the corresponding unsaturated acids and esters by use of a catalyst of the empirical formula:Mo.sub.12 P.sub.0.1-3 Bi.sub.0.01-2 M.sub.0.1-3 Cu.sub.0.01-2 V.sub.0.01-3 X.sub.a M'.sub.b O.sub.c (I)whereM is at least one of K, Rb and Cs;X is at least one of Ba, Zn, Ga, Cd, Ti, when a>0;M' is at least one of Ca, Mg, Ta, Zr, Ce, Ni, Co, Cr, Fe and Tl when b>0;a is a number of 0 to about 2;b is a number of 0 to about 2; andc is a number that satisfies the valence requirements of the other elements present.Type: GrantFiled: September 5, 1980Date of Patent: December 22, 1981Assignee: Standard Oil CompanyInventors: Wilfrid G. Shaw, James E. Rinz, Christos Paparizos
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Patent number: 4301087Abstract: Carbamates, such as ethyl carbamate, are prepared by contacting an alcohol, such as ethanol, with cyanogen and water in the presence of a dipolar, aprotic solvent, such as acetonitrile, and an acid catalyst, such as hydrochloric acid.Type: GrantFiled: August 18, 1980Date of Patent: November 17, 1981Assignee: Standard Oil CompanyInventor: Janice L. Greene
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Patent number: 4301319Abstract: Acetone is converted to allene by contacting the acetone with an alumina catalyst, such as .gamma.-alumina, at a temperature between about 300.degree. and 700.degree. C.Type: GrantFiled: May 16, 1980Date of Patent: November 17, 1981Assignee: Standard Oil CompanyInventor: Janice L. Greene
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Patent number: 4301077Abstract: Oxygenated C.sub.4 hydrocarbons, such as maleic anhydride, are hydrogenated to tetrahydrofuran and/or 1,4-butanediol by a process comprising contacting the hydrocarbon with hydrogen at hydrogenation conditions in the presence of less than 25 wt. % water, based on the weight of the hydrocarbon, and a ruthenium-containing hydrogenation catalyst, such as the catalyst of the formulaRu Ni Co Zn.sub.0.4.Type: GrantFiled: December 22, 1980Date of Patent: November 17, 1981Assignee: Standard Oil CompanyInventors: Frederick A. Pesa, Anne M. Graham
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Patent number: 4299991Abstract: Hydroperoxidizable hydrocarbons are hydroperoxidized by contacting them at hydroperoxidation conditions in the presence of a catalyst comprising a polymer containing maleimide linkages. For example, cumyl hydroperoxide can be produced by contacting cumene and oxygen with a catalyst comprising polymaleimide.Type: GrantFiled: December 28, 1979Date of Patent: November 10, 1981Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Curtie E. Uebele, Serge R. Dolhyj
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Patent number: 4299987Abstract: 1,1-diphenylethane or 1,1-diphenylethylene is oxidized to benzophenone by contacting the 1,1-diphenylethane or 1,1-diphenylethylene and oxygen with an antimonate catalyst.Type: GrantFiled: November 14, 1977Date of Patent: November 10, 1981Assignee: The Standard Oil CompanyInventors: Serge R. Dolhyj, Louis J. Velenyi
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Patent number: 4293719Abstract: Hydroperoxides, such as cyclohexylbenzene hydroperoxide, are manufactured by the oxidation of aryl compounds, such as cyclohexylbenzene, in the presence of a catalyst selected from the group consisting of C.sub.6 -C.sub.18 primary amines and polyvinylpyrrolidone.Type: GrantFiled: March 31, 1980Date of Patent: October 6, 1981Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Serge R. Dolhyj, Marcia H. Sundeen
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Patent number: 4279777Abstract: Dehydrogenatable hydrocarbons are dehydrogenated by contacting them at dehydrogenation conditions in the presence of a complex oxide catalyst comprising molybdenum, copper and tin and at least one element selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Th and U. For example, an alkyl aromatic hydrocarbon, e.g. ethylbenzene, can be dehydrogenated to an alkenyl aromatic hydrocarbon, e.g. styrene, in the presence of an oxide complex catalyst comprising molybdenum, copper, tin and at least one element selected from the group consisting of K, Cs, Ba, Mg and Ca.Type: GrantFiled: December 10, 1979Date of Patent: July 21, 1981Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Andrew S. Krupa
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Patent number: 4279829Abstract: Hydroperoxides are catalytically decomposed using a novel metal complex of the formula: ##STR1## wherein M is a positively charged metal or metal compound;Z is S, O, P, S--P, or S--S;L is C, P, or N; andA is selected from the group consisting of halogens; hydrogen; N--R wherein R is selected from the group consisting of H, C.sub.1-30 alkyls and 4 to 8 membered aryls optionally substituted with one or more C.sub.1-20 alkyls and C.sub.1-20 alkoxys; and hydrocarbon groups containing up to 30 carbon atoms optionally substituted with halogen atoms, C.sub.1-12 hydroxy groups, C.sub.1-12 acid groups, C.sub.1-12 aldehyde groups, C.sub.1-12 ketone groups, and C.sub.1-10 nitrile groups; andwhereinn is 1 or 2; andb is 1, 2 or 3.These catalysts are especially effective in decomposing either cumene hydroperoxide or cyclohexylbenzene hydroperoxide to phenol.Type: GrantFiled: October 31, 1979Date of Patent: July 21, 1981Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Christos Paparizos, Serge R. Dolhyj
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Patent number: 4262153Abstract: Hydroperoxides are catalytically decomposed using a novel metal complex of the formula: ##STR1## wherein M is a positively charged metal or metal compound;Z is S, O, P, S-P, or S-S;L is C, P, or N; andA is selected from the group consisting of halogens; hydrogen; N-R wherein R is selected from the group consisting of H, C.sub.1-30 alkyls and 4 to 8 membered aryls optionally substituted with one or more C.sub.1-20 alkyls and C.sub.1-20 alkoxys; and hydrocarbon groups containing up to 30 carbon atoms optionally substituted with halogen atoms, C.sub.1-12 hydroxy groups, C.sub.1-12 acid groups, C.sub.1-12 aldehyde groups, C.sub.1-12 ketone groups, and C.sub.1-10 nitrile groups; andwhereinn is 1 or 2; andb is 1, 2 or 3.These catalysts are especially effective in decomposing either cumene hydroperoxide or cyclohexylbenzene hydroperoxide to phenol.Type: GrantFiled: December 26, 1978Date of Patent: April 14, 1981Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Christos Paparizos, Serge R. Dolhyj
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Patent number: 4255283Abstract: This invention relates to an improved process for the dehydrogenation of alkyl-substituted aromatic compounds to the corresponding alkenyl-substituted aromatics in the presence of oxygen and in the presence of an improved metal phosphate catalyst composition.Type: GrantFiled: March 23, 1978Date of Patent: March 10, 1981Assignee: The Standard Oil CompanyInventors: Joseph P. Bartek, Robert K. Grasselli
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Patent number: 4246421Abstract: This invention relates to an improved process for the dehydrogenation of alkyl-substituted aromatic compounds to the corresponding alkenyl-substituted aromatics in the presence of oxygen and in the presence of an improved metal phosphate catalyst composition.Type: GrantFiled: September 15, 1978Date of Patent: January 20, 1981Assignee: The Standard Oil CompanyInventors: Joseph P. Bartek, Robert K. Grasselli
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Patent number: 4237303Abstract: A process for the removal of oxazole from acrylonitrile by contacting oxazole-containing acrylonitrile with a substantially dry cation exchange resin. The process exhibits the advantage of up to 40 percent or greater increase in the oxazole removal capacity than a corresponding process employing a water-wet cation exchange resin.Type: GrantFiled: April 30, 1979Date of Patent: December 2, 1980Assignee: The Dow Chemical CompanyInventor: Sterling C. Gatling
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Patent number: 4219687Abstract: Mononuclear aromatic hydrocarbons, e.g. benzene and analogs, are converted by hydroalkylation to the corresponding cycloalkyl aromatics by contacting the mononuclear aromatic hydrocarbons in the presence of hydrogen with a catalyst comprising a rare earth-exchanged Y-type zeolite support carrying a promoter comprising at least one of ruthenium, iridium, rhodium and palladium, the catalyst being calcined in an oxygen-containing atmosphere at a temperature of 250.degree. to 600.degree. C. prior to the hydroalkylation reaction.Type: GrantFiled: July 26, 1978Date of Patent: August 26, 1980Assignee: Standard Oil CompanyInventors: Serge R. Dolhyj, Louis J. Velenyi
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Patent number: 4218401Abstract: Primary and secondary alcohols are oxidized to aldehydes and ketones, respectively, by passing a gaseous mixture of the alcohol and oxygen (air) over a supported catalyst of Ru, Rh, Pd, Pt, Ir or Os. The catalyst is improved by admixture with a tin compound. The support for the catalyst is preferably alumina, silicon carbide or other inert material having a low surface to weight ratio. Preferred conditions are atmospheric pressure, about 250.degree.-500.degree. C. and a space velocity of 1000-4000/hr. Preferred alcohols are isopropanol, 1-methoxy-2-propanol and ethanol.Type: GrantFiled: January 11, 1974Date of Patent: August 19, 1980Assignee: The Dow Chemical CompanyInventor: C. Elmer Wymore
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Patent number: 4218572Abstract: Substituted or unsubstituted cyclohexylbenzene is dehydrogenated to substituted or unsubstituted biphenyl in the absence of oxygen over an oxide complex catalyst. The oxide complex catalyst comprises at least one element selected from the group consisting of Group VB and Group VIII elements, optionally promoted with at least one element selected from the group consisting of Group IA, Group IB, Group IIB, Group VIIB and Group VIB.Type: GrantFiled: September 28, 1978Date of Patent: August 19, 1980Assignee: Standard Oil CompanyInventors: Serge R. Dolhyj, Louis J. Velenyi
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Patent number: 4212735Abstract: The method of oxidizing organic compounds, such as 1,3,5-trichlorobenzene, in an aqueous system of pH not more than about 4, the method comprising oxidizing the organic compound by contacting the compound with an oxidizing agent, such as air, in the aqueous system in the presence of a catalytic amount of a cocatalyst system, is improved by using as the cocatalyst system a catalytic combination of nitrate ions, at least one of either bromide ions or iodide ions, and transition metal ions of at least one transition metal having two or more oxidation states, such as vanadium ions. This cocatalyst system enhances the rate of oxidation of the organic compounds.Type: GrantFiled: March 1, 1979Date of Patent: July 15, 1980Assignee: Hydroscience, Inc.Inventor: Richard A. Miller