Peroxy Containing Reactant Patents (Class 568/385)
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Patent number: 4769464Abstract: The invention relates to a process for the preparation of monocarbonyl or biscarbonyl compounds by reacting organic carbon compounds having one or more olefinic or aromatic double bonds in the molecule with the equivalent amount of ozone and by subsequently catalytically hydrogenating the ozonization products, wherein the peroxide-containing ozonization solution is fed continuously into a suspension of the hydrogenation catalyst in a lower aliphatic alcohol, while a peroxide content of not more than 0.1 mole/l is maintained, and the ozonization products are continuously cleaved reductively to give the corresponding carbonyl compounds.Type: GrantFiled: December 17, 1984Date of Patent: September 6, 1988Assignee: Chemie Linz Gesellschaft m.b.H.Inventor: Alexander Sajtos
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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: 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: 4626600Abstract: In accordance with the invention there is a process for reducing the water content of acetone prepared from cumene which includes the steps ofa. adding cleaving effective catalytic quantities of sulfuric acid to a mixture comprising cumene hydroperoxide and cumene, the cumene hydroperoxide making up about 81 to 83 weight percent of the said mixture, thereby producing a mixture comprising phenol, acetone, cumene and sulfuric acid;b. neutralizing the said sulfuric acid with an aqueous alkali hydroxide and separating the alkali metal sulfate from the mixture comprising phenol, acetone, water and cumene, the water being from about 40 to 60 weight percent of the total weight of water and cumene, the cumene being present in sufficient quantities to cause the formation of two liquid phases upon condensing the acetone fraction distillate;c. separating by distillation the acetone fraction from the phenol fraction, said acetone fraction containing acetone, water, aldehyde, and other organics including cumene;d.Type: GrantFiled: February 21, 1985Date of Patent: December 2, 1986Assignee: General Electric CompanyInventors: John W. Fulmer, William D. Kight
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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: 4607126Abstract: The invention relates to a process for the preparation of glyoxal, alkylglyoxals and acetals thereof by reacting .alpha.,.beta.-unsaturated dialkylacetals with the equivalent amount of ozone and subsequently subjecting the ozonization products to catalytic hydrogenation, the peroxide-containing ozonization solution being fed continuously into a suspension of the hydrogenation catalyst, while a peroxide content of not more than 0.1 mole/liter is maintained, and cleaving the ozonization products by reduction, after which the dialkylacetals formed in the hydrogenation are, if desired, cleaved to give glyoxal or alkylglyoxals.Type: GrantFiled: December 17, 1984Date of Patent: August 19, 1986Assignee: Chemie Linz AktiengesellschaftInventor: Alexander Sajtos
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Patent number: 4587057Abstract: Novel peroxide compounds and the use thereof. In particular, the present invention concerns .beta.-hydroxycyclopentylperoxide compounds of the general formula: ##STR1## wherein R.sub.1 represents hydrogen or an organic residue of 1 to 9 carbon atoms. These novel peroxide compounds are useful as an intermediate in the production of glutaraldehydes.Type: GrantFiled: July 8, 1983Date of Patent: May 6, 1986Assignee: Nippon Oil Co., Ltd.Inventors: Hitoshi Yuasa, Mitsuo Matsuno, Hirosuke Imai
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Patent number: 4567304Abstract: Benzene, toluene and ethylbenzene is removed from the heavy residues of a phenol distillation in a phenol and acetone from cumene process.Type: GrantFiled: May 24, 1984Date of Patent: January 28, 1986Assignee: General Electric CompanyInventor: John W. Fulmer
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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: 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: 4503259Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene) and then oxidizing the resulting product using formic acid and hydrogen peroxide; and optionally reacting the resulting product with a methyl Grignard reagent such as methyl magnesium chloride followed by hydrolysis; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together represent oxygen; or wherein, taken separately, R.sub.1 is hydroxyl and R.sub.2 is methyl or R.sub.Type: GrantFiled: May 24, 1983Date of Patent: March 5, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
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Patent number: 4490566Abstract: Phenol and acetone are produced by the cleavage of cumene hydroperoxide in the presence of a solid heterogeneous catalyst with acidic activity comprising an intermediate pore size zeolite such as ZSM-5.Type: GrantFiled: May 6, 1983Date of Patent: December 25, 1984Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Bruce P. Pelrine
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Patent number: 4490565Abstract: Phenol and acetone are produced by the cleavage of cumene hydroperoxide in the presence of a solid heterogeneous catalyst with acidic activity comprising zeolite beta.Type: GrantFiled: May 6, 1983Date of Patent: December 25, 1984Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Bruce P. Pelrine
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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: 4486606Abstract: Pinacolone is prepared by adding 2,3-dimethyl-2-butene and an aqueous solution of hydrogen peroxide at a temperature of 20.degree. to 90.degree. C. to a solution which contains water and one or more carboxylic acids having 1 to 8 C atoms and which can, if desired, also contain small amounts of a strong acid, increasing the temperature after substantial or complete reaction of the hydrogen peroxide, and distilling off as an azeotropic mixture with water the pinacolone formed.Type: GrantFiled: March 21, 1983Date of Patent: December 4, 1984Assignee: Bayer AktiengesellschaftInventors: Gebhard Rauleder, Helmut Waldmann
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Patent number: 4482757Abstract: Secondary alkyl-substituted benzene hydroperoxides are cleaved to phenols and ketones by contacting the hydroperoxide with a mixture consisting essentially of an organic phosphonium halide compound and an acid at a temperature from about 0.degree.-200.degree. C.Type: GrantFiled: June 24, 1983Date of Patent: November 13, 1984Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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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: 4480141Abstract: Secondary alkyl-substituted hydroperoxides are cleaved to phenols and ketones by contacting the secondary alkyl-substituted benzene hydroperoxide with boron phosphate, at a temperature of from about 20.degree.-200.degree. C.Type: GrantFiled: June 24, 1983Date of Patent: October 30, 1984Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4480134Abstract: Benzene is removed from the heavy residues of a phenol distillation in a phenol and acetone from cumene process.Type: GrantFiled: April 5, 1983Date of Patent: October 30, 1984Assignee: General Electric CompanyInventor: John W. Fulmer
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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: 4434305Abstract: High quality hydroquinone is produced from p-diisopropylbenzene dihydroperoxide at a high yield according to the disclosed process. The p-diisopropylbenzene dihydroperoxide is decomposed in the presence of an acid catalyst and the concentration of the hydroperoxide is maintained in the range of 0.1 to 1% by weight; the remaining hydroperoxide in the decomposition step is further subjected to an acid decomposition prior to the recovery of the formed hydroquinone product.Type: GrantFiled: December 1, 1981Date of Patent: February 28, 1984Assignee: Mitsui Petrochemicals Industry, Ltd.Inventors: Nobuo Kurosaka, Makoto Yasuda, Tadateru Murakami
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Patent number: 4421679Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene) and then oxidizing the resulting product using formic acid and hydrogen peroxide; and optionally reacting the resulting product with a methyl Grignard reagent such as methyl magnesium chloride followed by hydrolysis; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together represent oxygen; or wherein, taken separately, R.sub.1 is hydroxyl and R.sub.2 is methyl or R.sub.Type: GrantFiled: February 4, 1982Date of Patent: December 20, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
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Patent number: 4420423Abstract: Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene); then oxidizing the resulting product using formic acid and hydrogen peroxide; then reducing the resulting ketone(s) with an alkali metal borohydride; and then, optionally, reacting the resulting alcohol(s) with acetic anhydride to form one or more esters; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same.Also covered is the genus of compounds defined according to the structure ##STR1## wherein R.sub.12 represents hydroxyl:--OH]or acetoxy having the structure: ##STR2## and wherein R.sub.3, R.sub.4, R.sub.5, R.Type: GrantFiled: February 4, 1982Date of Patent: December 13, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Lambert Dekker, Frederick L. Schmitt, Augustinus G. Van Loveren
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Patent number: 4408083Abstract: Disclosed is a method of treating hydroperoxide mixtures, which comprises bringing an oily hydroperoxide mixture containing (A) an aromatic hydroperoxide having a hydroperoxymethyl group directly bonded to the aromatic nucleus and (B) an aromatic hydroperoxide having a 2-hydroperoxy-2-propyl group bonded directly to the aromatic nucleus into contact with an aqueous alkali solution, separating the aqueous phase from the oil phase and decomposing at least a part of the component (A) extracted in the aqueous phase.According to this method, the starting oily hydroperoxide mixture can be converted to a mixture in which the primary hydroperoxide content is reduced without substantial loss of the tertiary hydroperoxide. Therefore, aromatic hydroperoxide mixtures suitable for production of phenols can advantageously be proceeded.Type: GrantFiled: August 17, 1981Date of Patent: October 4, 1983Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Masakazu Toyoura, Koichi Shomura, Hirotoshi Tsuchida, Tadateru Murakami
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Patent number: 4379942Abstract: 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' whereA is fluoborate, acetate or trifluoroacetate, andA' is OOR.sub.1 and where R.sub.1 is a hydrocarbon radical.Type: GrantFiled: May 20, 1981Date of Patent: April 12, 1983Assignee: Institut Francais du PetroleInventors: Hubert Mimoun, Robert Charpentier, Michel Roussel
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Patent number: 4358618Abstract: A cumene oxidation product containing cumene hydroperoxide (CHP) and dimethylphenylcarbinol (DMPC) is decomposed with acid catalyst in a first step at mild temperatures that lowers the CHP concentration to about 0.5-5% and converts most of the DMPC to dicumylperoxide (DCP). In a second step at mild temperatures the CHP concentration is lowered below 0.4%. In a third step the DCP is decomposed at a higher temperature for a short time to alpha-methylstyrene (AMS), phenol and acetone, with any remaining DMPC also converted to AMS. The DCP concentration is monitored during the third step, and the reaction is stopped by cooling when about 0.5-5% of the DCP remains undecomposed so as to maximize AMS yield.Type: GrantFiled: June 22, 1981Date of Patent: November 9, 1982Assignee: Allied CorporationInventors: Stylianos Sifniades, Allen A. Tunick, Fred W. Koff
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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: 4322560Abstract: Exothermic hydroperoxide decomposition reactions catalyzed by solid polymeric acid catalysts are controlled by contacting the reactants with a thin film of the acid catalyst supported on the surface of an impermeable heat exchanger element and contacting the opposite side of the heat exchanger element with a heat transfer fluid.Type: GrantFiled: March 20, 1980Date of Patent: March 30, 1982Assignee: Varen TechnologyInventor: Ronald J. Vaughan
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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: 4297518Abstract: Cumene hydroperoxide in a solvent comprising phenol and acetone is decomposed to phenol and acetone using a soluble rhenium compound.Type: GrantFiled: November 18, 1977Date of Patent: October 27, 1981Assignee: Gulf Research & Development CompanyInventors: Ching-Yong Wu, Wayne R. Pretzer, Thaddeus P. Kobylinski
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Patent number: 4267380Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using a Lewis acid catalyst of the group tungsten hexafluoride, silicon tetrafluoride, stannous chloride, stannic fluoride, antimony pentachloride, sulfur monochloride and sulfur tetrafluoride.Type: GrantFiled: May 19, 1980Date of Patent: May 12, 1981Assignee: Gulf Research & Development CompanyInventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
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Patent number: 4267379Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using boron trifluoride or boron trifluoride complexed with an oxygen-containing polar compound as the decomposition catalyst. The boron trifluoride in the reaction product is then complexed with an amine such as trimethyl amine for recovery and reuse in the process.Type: GrantFiled: August 13, 1979Date of Patent: May 12, 1981Assignee: Gulf Research & Development CompanyInventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
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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: 4257985Abstract: Compounds containing at least one keto group and at least one peroxy group, each peroxy oxygen being joined to a tertiary carbon atom.Examples: 2-Methyl-2-(t-butylperoxy)-4-pentanone. 2,6-Dimethyl-2,6-bis(t-butylperoxy)-4-heptanone. 3,5,5-Trimethyl-3-(t-butylperoxy)cyclohexanone.The compounds are prepared by the strong acid catalyzed addition of a tertiary hydroperoxide to an .alpha.,.beta.-unsaturated ketone. Illustration: Mesityl oxide and pinanyl hydroperoxide, in slight excess, were reacted at 0.degree. C. in the presence of 77% sulfuric acid; the reaction mix was stirred for 16 hours at 25.degree. C. Product 2-methyl-2-pinanylperoxy-4-pentanone was recovered.Type: GrantFiled: May 7, 1968Date of Patent: March 24, 1981Assignee: Pennwalt CorporationInventor: Wilbur H. McKellin
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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
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Patent number: 4238417Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using boron trifluoride or a boron trifluoride complex as the decomposition catalyst. The boron trifluoride in the reaction product is reacted with a phosphorus-containing salt of an alkali metal such as sodium phosphate for recovery and reuse in the process.Type: GrantFiled: August 15, 1979Date of Patent: December 9, 1980Assignee: Gulf Research & Development CompanyInventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
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Patent number: 4217290Abstract: This invention consists of a process for preparing bifunctional aliphatic organic compounds of at least 6 carbon atoms, wherein a cycloaliphatic oxyhydroperoxide is reacted with an alpha-olefine having its double bond activated by a conjugate electron-attracting group, in the presence of a bivalent Cr salt, a bivalent V salt or a trivalent Ti salt.Type: GrantFiled: June 20, 1979Date of Patent: August 12, 1980Assignee: Brichima S.p.A.Inventors: Paolo Maggioni, Francesco Mauri, Attilio Citterio
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Patent number: 4210606Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using a halogen-substituted thiophenol as the catalyst.Type: GrantFiled: June 15, 1979Date of Patent: July 1, 1980Assignee: Gulf Research and Development CompanyInventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
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Patent number: 4210607Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using an isolable nitrosonium or nitronium salt as the catalyst. Nitrosonium tetrafluoborate catalyzes the decomposition of cumene hydroperoxide to phenol and acetone.Type: GrantFiled: June 20, 1979Date of Patent: July 1, 1980Assignee: Gulf Research and Development CompanyInventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
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Patent number: 4209465Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using an isolable carbonium, tropylium or oxonium salt as the catalyst. Triphenylcarbonium tetrafluoborate catalyzes the decomposition of cumene hydroperoxide to phenol and acetone.Type: GrantFiled: June 20, 1979Date of Patent: June 24, 1980Assignee: Gulf Research and Development CompanyInventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
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Patent number: 4207264Abstract: A continuous process for cleaving aralkyl hydroperoxides in acid media to yield phenols and carbonyl compounds in a reactor arranged and operated to limit the total residence time to less than the time required to form discoloration products.Type: GrantFiled: March 27, 1973Date of Patent: June 10, 1980Assignee: The Goodyear Tire & Rubber CompanyInventors: John E. Anderson, Ernest G. Hildenbrand
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Patent number: 4207265Abstract: A process is provided for the preparation of hydroquinone by oxidizing a phenol having in the paraposition a 1-cycloalkenyl or .alpha.-methylene-(alkyl or aralkyl) group. The oxidation is carried out using hydrogen peroxide or a hydrocarbyl peroxide in the presence of an inert solvent and a catalytic amount of a strong acid which is not oxidized by the peroxide. The other product of the reaction is the ketone derived by oxidation of the para-substituent in the starting phenol, e.g. p-isopropenylphenol gives hydroquinone and acetone. The reaction forms a particularly convenient route for conversion of phenol to hydroquinone in that phenol is condensed with acetone to bisphenol A, the latter is degraded by alkaline hydrolysis to a mixture of phenol and p-isopropenylphenol, which latter is subjected, without separation, to the above process to give a mixture of hydroquinone, phenol, and acetone.Type: GrantFiled: March 31, 1975Date of Patent: June 10, 1980Assignee: The Upjohn CompanyInventor: Peter S. Carleton