Patents Represented by Attorney Gary R. Plotecher
  • Patent number: 4319066
    Abstract: 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: Grant
    Filed: August 1, 1980
    Date of Patent: March 9, 1982
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Serge R. Dolhyj, Andrew S. Krupa
  • Patent number: 4314075
    Abstract: 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: Grant
    Filed: September 5, 1980
    Date of Patent: February 2, 1982
    Assignee: The Standard Oil Company
    Inventors: Wilfrid G. Shaw, Philip L. Kuch, Christos Paparizos
  • Patent number: 4309310
    Abstract: 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: Grant
    Filed: March 31, 1980
    Date of Patent: January 5, 1982
    Assignee: Standard Oil Company
    Inventor: James L. Callahan
  • Patent number: 4307247
    Abstract: 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: Grant
    Filed: September 5, 1980
    Date of Patent: December 22, 1981
    Assignee: Standard Oil Company
    Inventors: Wilfrid G. Shaw, James E. Rinz, Christos Paparizos
  • Patent number: 4301087
    Abstract: 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: Grant
    Filed: August 18, 1980
    Date of Patent: November 17, 1981
    Assignee: Standard Oil Company
    Inventor: Janice L. Greene
  • Patent number: 4301319
    Abstract: 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: Grant
    Filed: May 16, 1980
    Date of Patent: November 17, 1981
    Assignee: Standard Oil Company
    Inventor: Janice L. Greene
  • Patent number: 4301077
    Abstract: 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: Grant
    Filed: December 22, 1980
    Date of Patent: November 17, 1981
    Assignee: Standard Oil Company
    Inventors: Frederick A. Pesa, Anne M. Graham
  • Patent number: 4299991
    Abstract: 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: Grant
    Filed: December 28, 1979
    Date of Patent: November 10, 1981
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Curtie E. Uebele, Serge R. Dolhyj
  • Patent number: 4299987
    Abstract: 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: Grant
    Filed: November 14, 1977
    Date of Patent: November 10, 1981
    Assignee: The Standard Oil Company
    Inventors: Serge R. Dolhyj, Louis J. Velenyi
  • Patent number: 4293719
    Abstract: 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: Grant
    Filed: March 31, 1980
    Date of Patent: October 6, 1981
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Serge R. Dolhyj, Marcia H. Sundeen
  • Patent number: 4279777
    Abstract: 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: Grant
    Filed: December 10, 1979
    Date of Patent: July 21, 1981
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Andrew S. Krupa
  • Patent number: 4279829
    Abstract: 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: Grant
    Filed: October 31, 1979
    Date of Patent: July 21, 1981
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Christos Paparizos, Serge R. Dolhyj
  • Patent number: 4262153
    Abstract: 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: Grant
    Filed: December 26, 1978
    Date of Patent: April 14, 1981
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Christos Paparizos, Serge R. Dolhyj
  • Patent number: 4255283
    Abstract: 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: Grant
    Filed: March 23, 1978
    Date of Patent: March 10, 1981
    Assignee: The Standard Oil Company
    Inventors: Joseph P. Bartek, Robert K. Grasselli
  • Patent number: 4246421
    Abstract: 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: Grant
    Filed: September 15, 1978
    Date of Patent: January 20, 1981
    Assignee: The Standard Oil Company
    Inventors: Joseph P. Bartek, Robert K. Grasselli
  • Patent number: 4237303
    Abstract: 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: Grant
    Filed: April 30, 1979
    Date of Patent: December 2, 1980
    Assignee: The Dow Chemical Company
    Inventor: Sterling C. Gatling
  • Patent number: 4219687
    Abstract: 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: Grant
    Filed: July 26, 1978
    Date of Patent: August 26, 1980
    Assignee: Standard Oil Company
    Inventors: Serge R. Dolhyj, Louis J. Velenyi
  • Patent number: 4218401
    Abstract: 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: Grant
    Filed: January 11, 1974
    Date of Patent: August 19, 1980
    Assignee: The Dow Chemical Company
    Inventor: C. Elmer Wymore
  • Patent number: 4218572
    Abstract: 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: Grant
    Filed: September 28, 1978
    Date of Patent: August 19, 1980
    Assignee: Standard Oil Company
    Inventors: Serge R. Dolhyj, Louis J. Velenyi
  • Patent number: 4212735
    Abstract: 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: Grant
    Filed: March 1, 1979
    Date of Patent: July 15, 1980
    Assignee: Hydroscience, Inc.
    Inventor: Richard A. Miller