Carbon Monoxide Or Peroxy Containing Reactant Patents (Class 568/342)
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Patent number: 5149880Abstract: Nitrogen-containing aromatic heterocyclic ligand-metal complexes and their use for the activation of hydrogen peroxide and dioxgen are disclosed. Processes whereby activated hydrogen peroxide or dioxygen are used to transform various organic substrates are also disclosed. In particular, processes for the conversion of methylenic carbons to carbonyls, for the dioxygenation of aryl olefins, acetylenes and aryl-.alpha.-diols, for the oxidation of alcohols and aldehydes and for the removal of mercaptans from gaseous streams and for the removal of hydrogen sulfide and/or mercaptans from liquid streams are disclosed.Type: GrantFiled: August 24, 1990Date of Patent: September 22, 1992Assignee: The Texas A & M University SystemInventors: Donald T. Sawyer, Ceshing Sheu, Andrzej Sobkowiak, Hui-Chan Tung
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Patent number: 5133903Abstract: Hydrocarboxyalkylation of .alpha.,.omega.-dienes with carbon monoxide and an alcohol in the presence of a cobalt compound and a tertiary amine gives .omega.-enecarboxylic acid esters with high selectivity and in good yields.Type: GrantFiled: February 28, 1989Date of Patent: July 28, 1992Assignee: Huels AktiengesellschaftInventors: Reinhold Gull, Thomas Keil
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Patent number: 5126491Abstract: Process for oxidating paraffinic compounds in order to yield the corresponding alcoholic and/or ketonic compounds, which process consists of reacting said paraffins with an aqueous solution of hydrogen peroxide, possibly dissolved in a solvent, by operating at a temperature comprised within the range of from 0.degree. C. to 100.degree. C., in the presence of a titanium-silicalite of formulapHMO.sub.2.qTiO.sub.2.SiO.sub.2whereinM is a metal selected from among aluminum, gallium and iron,p is comprised within the range of from 0 to 0.05 andq is comprised within the range of from 0.0001 to 0.04, and the H.sup.+ of HMO.sub.2 can be least partially replaceable or replaced by cations.Type: GrantFiled: August 3, 1990Date of Patent: June 30, 1992Assignee: Eniricerche S.p.A.Inventors: Mario G. Clerici, Bartolomeo Anfossi, Giuseppe Bellussi
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Patent number: 5041682Abstract: Reaction mixtures which contain cyclohexanol, cyclohexanone and cyclohexyl hydroperoxide and are obtained in the oxidation of cyclohexane with molecular oxygen, or with a gas containing this, in the liquid phase are worked up by a process in which the reaction mixture is hydrogenated in the presence of a noble metal catalyst at elevated temperatures and under superatmospheric pressure, the resulting mixture is treated with an aqueous alkali metal carbonate solution, and cyclohexanol and cyclohexanone are separated off by distillation.Type: GrantFiled: September 19, 1988Date of Patent: August 20, 1991Assignee: BASF AktiengesellschaftInventors: Juergen Hartig, Armin Stoessel, Ekhart Lucas
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Patent number: 5021607Abstract: Saturated hydrocarbon chains are oxidized using a titanium containing silicalite catalyst having an infra red absorption band around 950 cm.sup.-1 preferably in solutions, the chains may be alkanes or alkyl groups of alkyl cyclic compounds.Type: GrantFiled: September 10, 1990Date of Patent: June 4, 1991Assignee: Exxon Chemical Patents Inc.Inventor: Diana R. Huybrechts
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Patent number: 5004837Abstract: The invention relates to a process for preparing a cycloalkanone and/or cycloalkanol by oxidation of a cycloalkane using oxygen to form a hydroperoxide, followed by a decomposition of the hydroperoxide, in the presence of an organic metal complex, the decomposition being carried out in the presence of a phthalocyanine or porphyrin metal complex immobilized on a carrier material.Type: GrantFiled: October 20, 1989Date of Patent: April 2, 1991Assignee: Stamicarbon B.V.Inventors: Henricus A. C. Baur, Ubaldus F. Kragten
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Patent number: 4918238Abstract: Mixtures of alcohols and ketones are selectively and actively produced by catalytically oxidizing at least one alkane with an organic hydroperoxide, in the presence of a catalytically effective amount of osmium or an osmium compound, notably osmium tetroxide.Type: GrantFiled: March 3, 1989Date of Patent: April 17, 1990Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Jean-Pierre Lecomte
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Patent number: 4898984Abstract: A process for preparing 3,5,5-trimethyl-4-hydroxy-2-cyclohexen-1-one, comprising:oxidizing beta-isophorone in the presence of hydrogen peroxide and a weak organic acid at a temperature in the range of 0.degree.-100.degree. C.Type: GrantFiled: November 30, 1988Date of Patent: February 6, 1990Assignee: Huels AktiengesellschaftInventor: Hans Bellut
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Patent number: 4877903Abstract: Mixtures containing cyclohexanol and cyclohexanone are produced by oxidizing cyclohexane with air, and then decomposing the cyclohexyl hydroperoxide in such reaction mixture, in the presence of the cyclohexane, to form cyclohexanol and cyclohexanone, such oxidation and/or decomposition being carried out in the presence of a manganese source, a Bronsted acid and a pyridine ligand.Type: GrantFiled: November 14, 1988Date of Patent: October 31, 1989Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Francoise Igersheim
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Patent number: 4859799Abstract: Process for the production of aldehydes or ketones by oxidative cleavage of olefinic double bonds by means of a coordination complex of a ligand and a peroxo derivative of a metal of group 6b.Aldehydes and ketones obtained by said process are used among others as intermediates in the synthesis of organic products.Type: GrantFiled: May 20, 1988Date of Patent: August 22, 1989Assignee: Interox (Societe Anonyme)Inventors: Sandro Campestrini, Fulvio Di Furia, Giorgio Modena, Lucia Pasquato
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Patent number: 4818810Abstract: A process for the preparation of polyketones is disclosed, the process being the polymerization of a mixture of CO and an alkenically unsaturated hydrocarbon in the presence of a Group-VIII-metal catalyst containing ligands, wherein hydrocarbon groups occur which are bound to an element from Group V a, characterized in that the catalyst used is a complex compound obtained by reaction of a palladium, cobalt or nickel compound, an anion of a carboxylic acid with a pKa lower than 2, and a bidentate ligand of the general formula R.sup.1 R.sup.2 --M--R--M--R.sup.3 R.sup.4, wherein M represents phosphorus, arsenic or antimony, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are similar or dissimilar hydrocarbon groups, R is divalent organic bridging group not causing steric hindrance.Type: GrantFiled: October 2, 1985Date of Patent: April 4, 1989Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4814511Abstract: Cyclohexyl hydroperoxide containing reaction mixtures obtained by oxidation of cyclohexane with molecular oxygen or molecular oxygen containing gases in the liquid phase at from 130.degree. to 200.degree. C. and under from 5 to 125 bar are worked up by reaction with cycloolefins at elevated temperature in the presence of catalysts to react cyclohexyl hydroperoxide with cyclohexene at elevated temperatures in the presence of cyclohexene-soluble compounds of transition metals of groups 4 or 5 or 6 of the periodic table or of one or more cyclohexane-insoluble compounds of a transition metal of group 4 or 5 or 6, or in the presence of selenium, tellurium or a boride, and the resulting cyclohexene oxide at elevated temperatures to cyclohexanol in the presence of hydrogenation catalysts.Type: GrantFiled: October 23, 1987Date of Patent: March 21, 1989Assignee: BASF AktiengesellschaftInventors: Gerald Neubauer, Rolf Schnabel, Juergen Hartig, Josef Ritz
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Patent number: 4788325Abstract: A process for making a carbonyl-containing compound is disclosed. In this process an allylic ether is contacted with water in the presence of a cobalt-containing material under an atmosphere of carbon monoxide gas.Type: GrantFiled: May 29, 1987Date of Patent: November 29, 1988Assignee: National Distillers and Chemical CorporationInventor: Biau-Hung Chang
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Patent number: 4754073Abstract: Method for the preparation of ketones, by means of oxydation of the corresponding secondary alcohols, characterized in that said alcohols are catalytically oxidized by H.sub.2 O.sub.2 inside a two-phase system comprising:(a) an aqueous phase, containing hydrogen peroxide as the oxidizing agent;(b) an organic phase, containing a secondary alcohol and optionally a solvent immiscible with said aqueous phase, as well as a peroxidic catalyst having the general formula Q.sub.3 XW.sub.4 O.sub.24, wherein X represents an atom of phosphorus or of arsenic and wherein Q represents a quaternary cation, containing hydrocarbon groups having a total of from 20 to 70 C atoms.Type: GrantFiled: January 8, 1987Date of Patent: June 28, 1988Assignees: Instituto Guido Donegani S.p.A., Consiglio Nazionale Delle RicercheInventors: Carlo Venturello, Mario Gambaro, Marco Ricci
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Patent number: 4727195Abstract: A process for preparing compounds of the general formula:R--C.tbd.C--C(O)--C(R).dbd.CH.sub.2 (I)R represents an H atom or an optionally substituted hydrocarbyl group, by reacting a compound R--C.tbd.CH with CO in the presence of a Pd(II) compound, an organic phosphine and a protonic acid having a pK.sub.a below 3.0.Compounds of formula I in which R represents an optionally substituted hydrocarbyl group are novel.Type: GrantFiled: August 22, 1986Date of Patent: February 23, 1988Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4720592Abstract: The reaction mixture obtained by oxidation of cyclohexane using a cobalt catalyst is extracted with water to remove undesirable oxidation products such as diacids, hydroxy acids, and cobalt catalyst. The resulting mixture is then hydrogenated using a fixed bed hydrogenation catalyst to convert cyclohexyl hydroperoxide to cyclohexanol and cyclohexanone.Type: GrantFiled: September 5, 1986Date of Patent: January 19, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Usamah N. Besmar, John B. Lyon, Francis J. Miller, Michael T. Musser
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Patent number: 4704476Abstract: Reaction mixtures which contain cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone and are obtained by oxidizing cyclohexane with molecular oxygen, or a gas containing this, in the liquid phase at from 130.degree. to 200.degree. C. under from 5 to 25 bar are worked up by treatment with an aqueous alkali solution in the presence of a cobalt salt at elevated temperatures by an improved process wherein a phosphonic acid compound of the formula ##STR1## where X is alkylene or 2 to 6 carbon atoms, R.sub.1 is --CH.sub.2 PO.sub.3 H and R.sub.2, R.sub.3 and R.sub.4 may be identical or different and are each --CH.sub.2 PO.sub.3 H, --CH.sub.2 OH, hydrogen or alkyl of 1 to 4 carbon atoms, is concomitantly used.Type: GrantFiled: January 15, 1987Date of Patent: November 3, 1987Assignee: BASF AktiengesellschaftInventors: Juergen Hartig, Guenter Herrmann, Ekhart Lucas
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Patent number: 4659829Abstract: The invention concerns peroxide complexes of metals complying with the general formula LnMXpY, wherein M is a metal selected from groups VIII, IB and VIIB, particularly cobalt, X is an anionic group, for example carboxylate, R is an alkyl, cycloalkyl or arylalkyl group, n=1 or 2, p=0 or 1 and n+p=2.L is a tridentated ligand from the group of 1,3 bis (2-pyridylimino) isoindolines.These complexes are obtained by reaction of a hydroperoxide ROOH with a complex of formula LnMXp. They can be used in oxidizing hydrocarbons to a mixture of alcohols and ketones, either as reactants or as catalysts.They are particularly useful to prepare tert-butanol by oxidation of isobutane in liquid phase, by means of an oxygen-containing gas such as air.Type: GrantFiled: January 31, 1985Date of Patent: April 21, 1987Assignee: Institut Francais du PetroleInventors: Lucien Saussine, Alain Robine, Hubert Mimoun
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Patent number: 4618724Abstract: This invention deals with the use of a perfluorocarbon polymer oxidation catalyst consisting of a perfluorocarbon main chain and a side chain constructed from structural units of chromium (III) difluoromethylene sulfonate or cerium (IV) difluoromethylene sulfonate in a method of preparing a carbonyl compound through an oxidation of an alcohol.Type: GrantFiled: February 11, 1985Date of Patent: October 21, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Hitosi Nozaki, Koichiro Oshima
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Patent number: 4609763Abstract: A process for the oxidation of alkanes or alkenes is described. The process uses a hydrocarbyl hydroperoxide as an oxidizing agent in combination with a ruthenium catalyst and optionally a hydrogen bromide or hydrobromide acid promoter. The products of the oxidation are alcohols, ketones or a mixture of both.Type: GrantFiled: September 3, 1985Date of Patent: September 2, 1986Assignee: The British Petroleum Company P.L.C.Inventors: Colin G. Griggs, Anthony R. Middleton
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Patent number: 4585897Abstract: A process for hydration and condensation of acetylene in a crude acetylene stream containing water in the presence of a zirconia-alumina catalyst containing water to prepare aliphatic, aromatic and oxygenated compounds suitable for use as high octane liquid water fuels and as octane improvers for motor fuels is disclosed.Type: GrantFiled: August 24, 1984Date of Patent: April 29, 1986Assignee: Standard Oil Company (Indiana)Inventors: Ellis K. Fields, Mark L. Winzenburg, David A. De Marco
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Patent number: 4568769Abstract: Disclosed in a method for producing a mixture containing cycloalkanone and/or cycloalkanol which comprises oxidizing a cycloalkane with molecular oxygen to a cycloalkyl hydroperoxide represented by the formula (1): ##STR1## (wherein m represents an integer of 4.ltoreq.m.ltoreq.11) and decomposing the cycloalkyl hydroperoxide to obtain a mixture containing cycloalkanone and/or cycloalkanol, wherein the oxidation of the cycloalkane with molecular oxygen and/or the decomposition of the cycloalkyl hydroperoxide are carried out in the presence of a catalyst composition comprising at least one metallic salt represented by the formula (2):MX.sub.n (2)(wherein M represent Co, Mn, Cr or Fe, X represents an anionic ligand and n represents 2 or 3) and at least one compound represented by the formula (3): ##STR2## (wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: June 20, 1984Date of Patent: February 4, 1986Assignee: Sumitomo Chemical CompanyInventors: Akira Yashima, Teruo Matsuda, Tadao Sato, Mitsuaki Takahashi, Kiyomi Sakai
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Patent number: 4551553Abstract: The process of decomposing a hydroperoxide by contacting the hydroperoxide with a catalytic quantity of a catalyst system comprised of chromium and ruthenium. The catalyst system is characterized by its high stability while exhibiting improved activity for hydroperoxide decomposition and selectivity to desired alcohol and ketone products.Type: GrantFiled: February 22, 1983Date of Patent: November 5, 1985Assignee: Atlantic Richfield CompanyInventors: Paul D. Taylor, Michael T. Mocella
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Patent number: 4543427Abstract: Cyclohexanol and cyclohexanone are prepared by treating cyclohexyl hydroperoxide with a supported catalyst containing from 2 to 30% by weight, calculated as cobalt, of cobalt in oxidic form, at from 30.degree. to 160.degree. C., by a process wherein a zeolite is used as the carrier.Type: GrantFiled: June 6, 1983Date of Patent: September 24, 1985Assignee: BASF AktiengesellschaftInventors: Juergen Hartig, Armin Stoessel, Guenter Herrmann, Laszlo Marosi
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Patent number: 4518797Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: May 21, 1985Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4513150Abstract: But-2-ene-1,4-diones substituted in the 1,4-positions, of the formula ##STR1## where R.sup.1 and R.sup.2 are each an aliphatic hydrocarbon radical of 1 to 17 carbon atoms, are prepared by a process in which a 2,5-disubstituted furan of the formula ##STR2## where R.sup.1 and R.sup.2 have the above meaning, is oxidized with a percarboxylic acid in the presence of a carboxylic acid.Type: GrantFiled: March 23, 1984Date of Patent: April 23, 1985Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Hans-Martin Weitz, Hardo Siegel
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Patent number: 4508923Abstract: There is disclosed an improved process for oxidizing a hydrocarbon to produce a reaction mixture containing the corresponding organic hydroperoxide of said hydrocarbon and decomposing said hydroperoxide to provide a mixture containing reaction products of said decomposition reaction, including alcohol and/or ketone products, comprising effecting said oxidation and/or decomposition in the presence of a catalytic quantity of a catalyst system comprised of ruthenium and chromium.Type: GrantFiled: February 22, 1983Date of Patent: April 2, 1985Assignee: Atlantic Richfield CompanyInventors: Paul D. Taylor, Michael T. Mocella
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Patent number: 4503257Abstract: An improvement in a process for decomposing mixtures of cyclohexane and cyclohexyl hydroperoxide is provided. According to the improved process, a mixture comprising cyclohexane and cyclohexyl hydroperoxide is contacted with a catalyst consisting essentially of Co.sub.3 O.sub.4, MnO.sub.2, or Fe.sub.3 O.sub.4 applied to a suitable solid support, at a temperature from about 80.degree. C. to about 130.degree. C., in the presence of molecular oxygen.Type: GrantFiled: May 18, 1983Date of Patent: March 5, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventors: Joe D. Druliner, Joshua Hermolin
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Patent number: 4499305Abstract: An improvement in a process for decomposing mixtures of cyclohexane and cyclohexyl hydroperoxide to mixtures of cyclohexanone and cyclohexanol is disclosed. According to the improved process, stable catalyst dispersions, or solutions derived therefrom, of transition metal complexes of certain 1,3-bis(2-pyridylimino)isoindolines are formed by mixing, in cyclohexanone, cyclohexanol or mixtures of cyclohexanone, cyclohexanol and cyclohexane, cobalt, iron or manganese salts and 1,3-bis(2-pyridylimino)isoindolines.Type: GrantFiled: April 11, 1983Date of Patent: February 12, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joshua Hermolin
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Patent number: 4487972Abstract: This specification discloses a process for the production of oxygenated compounds, more specifically aldehydes and alcohols, by reacting an olefin with hydrogen and carbon monoxide in the presence of, as a ctalyst, an insoluble polymer containing a functional group, which may be an amine, thiol, phosphine, or arsine group, having chemically bonded thereto a metal of Group VIII of the Periodic Table. The metal can be, for example, rhodium, cobalt, or ruthenium. The olefin can contain more than one carbon-to-carbon double bond, may be an open chain or a cyclic olefin, and may be substituted. Further, the olefin may be contained in a refinery stream such as a cracked gasoline. The reaction may be carried out in the presence of a polar solvent.Type: GrantFiled: April 22, 1980Date of Patent: December 11, 1984Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell D. Whitehurst
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Patent number: 4487970Abstract: Secondary-alkyl substituted benzene hydroperoxides are cleaved to form phenols and ketones by contacting the secondary-alkyl substituted benzene hydroperoxide with a catalyst consisting essentially of about 3:1 to 1:10 by weight of SbF.sub.5 and graphite in the presence of an aromatic or ketone solvent at a temperature of from about 0.degree.-100.degree. C.Type: GrantFiled: June 3, 1983Date of Patent: December 11, 1984Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4482746Abstract: An improvement in a process for decomposing cyclohexyl hydroperoxide to cyclohexanone and cyclohexanol is provided. According to the improved process, a reaction mixture comprising cyclohexane and cyclohexyl hydroperoxide is contacted with two catalyst compositions sequentially for a preselected reaction period, such that the reaction mixture is contacted with a catalytic amount of the first of said catalyst compositions only for about 10 to about 80 percent of the reaction period, and contacted with a catalytic amount of a mixture of the first and second catalyst compositions for the remainder of the preselected reaction time. The first catalyst composition of the invention is a cyclohexane-soluble chromium organic acid salt, and the second catalyst composition is a cobalt, iron, or manganese complex of a 1,3-bis(2-pyridylimino)isoindoline.Type: GrantFiled: April 11, 1983Date of Patent: November 13, 1984Assignee: E. I. Du Pont de Nemours & CompanyInventor: Joshua Hermolin
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Patent number: 4480135Abstract: A process for oxidizing primary and/or secondary alcohols to the corresponding aldehyde and/or ketone derivatives, consisting of reacting said alcohols with an aqueous solution of hydrogen peroxide in the presence of synthetic zeolites containing titanium atoms, of general formula:xTiO.sub.2.(1-x)SiO.sub.2,where x lies between 0.0001 and 0.04, and possibly in the presence of one or more solvents, operating at a temperature of between 20.degree. and 100.degree. C.Type: GrantFiled: July 14, 1983Date of Patent: October 30, 1984Assignee: Anic S.p.A.Inventors: Antonio Esposito, Carlo Neri, Franco Buonomo
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Patent number: 4465861Abstract: There is disclosed an improved process of decomposing a reaction mixture containing cyclohexyl hydroperoxide to form a mixture containing cyclohexanone and cyclohexanol comprising using in the decomposition step a catalyst composition consisting essentially of (a) a specified salt of chromium, cobalt, iron, manganese, molybdenum or vanadium and (b) as a stabilizing agent, an alkylsulfonic acid, an alkylarenesulfonic acid, an alkylammonium sulfonate, or an alkylphosphonium sulfonate.Type: GrantFiled: April 11, 1983Date of Patent: August 14, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joshua Hermolin
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Patent number: 4459427Abstract: A mixture of the alcohol and ketone derivatives of alkanes is produced by reacting the alkane with a hydrocarbyl hydroperoxide, eg t-butyl hydroperoxide, at ambient or elevated temperature and pressure in the presence as catalyst of an iron or manganese square planar complex having heterocyclic nitrogen-donor ligands, e.g. a porphyrin or phthalocyanine complex, which complex has either no axial ligands, eg the lower valency or cationic complex, or an axial ligand which is non-coordinating or weakly-coordinating.Type: GrantFiled: October 26, 1982Date of Patent: July 10, 1984Assignee: The British Petroleum Company p.l.c.Inventors: Anthony R. Middleton, David J. H. Smith
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Patent number: 4329509Abstract: A process for the co-production of 2-alkanones having at least five carbon atoms and phenol or a substituted phenol. In the first step, benzene or a substituted benzene is alkylated with an alkyl moiety of at least five carbon atoms to selectively produce the 2-arylalkane isomer. Subsequent oxidation to the hydroperoxide and acid cleavage thereof yields the desired product. The alkylation step is carried out in the presence of a novel class of selective crystalline zeolite materials having pore openings with a major dimension of six to seven angstroms.Type: GrantFiled: January 22, 1981Date of Patent: May 11, 1982Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Lewis B. Young
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Patent number: 4310704Abstract: Methyl ketones are prepared in liquid phase by oxidizing terminal olefins of the formula R--CH.dbd.CH.sub.2, where R is a hydrocarbon radical. The oxidizing agent is hydrogen peroxide or an organic hydroperoxide, and the catalyst is a palladium catalyst of the formula Pd AA', (L.sub.m) whereA is fluoborate, acetate or trefrafluoroacetateA' is the same as A or is .pi.-allyl,m is 0 or 2, andL is a ligand selected from the amines, the phosphines, the arsines, the stibines and the amides.Type: GrantFiled: December 18, 1979Date of Patent: January 12, 1982Assignee: Institut Francais du PetroleInventors: Hubert Mimoun, Robert Charpentier, Michel Roussel
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Patent number: 4284820Abstract: 4-Formyl-3,6,6-trimethylbicyclo[3.1.0]hex-3-ene is oxidized in one vessel by a peroxy acid via 3,4-epoxy-4-formyl-3,6,6-trimethylbicyclo[3.1.0]hexane and 3,4-epoxy-4-formyloxy-3,6,6-trimethylbicyclo[3.1.0]hexane to 3,6,6-trimethyl-3-hydroxybicyclo[3.1.0]hexan-4-one. The four compounds are novel and are intermediates to pyrethroid insecticides.Type: GrantFiled: September 23, 1980Date of Patent: August 18, 1981Assignee: Shell Oil CompanyInventor: Johannes L. M. Syrier
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Patent number: 4259527Abstract: A catalytic system for oxidation of organic compounds including olefins, cyclic ketones and secondary alcohols. Soluble peroxo or solid supported oxo or peroxo complexes of molybdenum or tungsten are used in the presence of hydrogen peroxide to effect the oxidation. The resulting products include lactones, hydroxy acids, ketoacids, hydroxy esters and ketoesters from cyclic ketones; ketones from secondary alcohols and polyols or derivatives thereof from allylic alcohols.Type: GrantFiled: May 18, 1979Date of Patent: March 31, 1981Assignee: Allied Chemical CorporationInventors: Frank Mares, Stephen E. Jacobson, Reginald T. Tang
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Patent number: 4258205Abstract: New 2,2-dimethylcyclopropanecarbaldehyde dimethyl acetal derivatives of the formula ##STR1## wherein X is --CH.sub.2 OC(O)CH.sub.3, --CH.sub.2 OH, or --CHO are useful chemical intermediates for the preparation of pesticidally active cyclopropanecarboxylates.Type: GrantFiled: December 4, 1978Date of Patent: March 24, 1981Assignee: Shell Oil CompanyInventors: Johannes Van Berkel, Hendrik C. Kelderman
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Patent number: 4246203Abstract: The invention relates to a process in which an aromatic hydroperoxide of formula: ##STR1## wherein independently R.sub.1 is methyl or ethyl, R.sub.2 is hydrogen, methyl or ethyl, or where R.sub.1 and R.sub.2 together form an alicyclic ring of 5 or 6 carbon atoms, R.sub.3 is hydrogen or alkyl and R.sub.4 and R.sub.5 are hydrogen, alkyl or together form an automatic ring, n is 0, 1 or 2 and n.sup.1 is 1 or 2, is converted to a phenol and a carbonyl compound in a catalyzed cleavage decomposition reaction. In particular cumene hydroperoxide is converted to phenol and acetone. Instead of removing the decomposition products from the reactor in the liquid phase and dissipating the reaction heat as in prior art processes the heat is used to remove the phenol and the carbonyl compound in the vapor phase leaving a liquid residue of higher-boiling compounds and catalyst in the case where a liquid cleavage catalyst is employed.Type: GrantFiled: August 9, 1979Date of Patent: January 20, 1981Assignee: BP Chemicals LimitedInventor: Max M. Wirth