Oxy Containing Aldehyde Formed Patents (Class 568/432)
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Patent number: 4481374Abstract: The invention relates to a process for the preparation of hydroxybenzaldehydes by oxidation of hydroxybenzylic alcohols through oxygen or oxygen-containing gas, said process being carried out in aqueous alkaline medium in the absence of any catalyst whatsoever, at a temperature comprised between 25.degree. and 50.degree. C. and in the presence of an alkaline hydroxide in such a quantity that the molar ratio of alkaline hydroxide to hydroxybenzylic alcohol used is comprised between 2.25 and 10.Type: GrantFiled: August 26, 1982Date of Patent: November 6, 1984Assignee: Societe Francaise HoechstInventors: Yani Christidis, Jean-Claude Vallejos
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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: 4471140Abstract: Aromatic aldehydes are formed by the liquid phase reaction of molecular oxygen with methyl-substituted aromatic compounds in the presence of base, a cobalt, manganese, chromium or nickel salt catalyst and an easily removable amine.Type: GrantFiled: August 19, 1982Date of Patent: September 11, 1984Assignee: The Dow Chemical CompanyInventor: Andrew T. Au
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Patent number: 4453016Abstract: Aromatic aldehydes are formed by the liquid phase reaction of molecular oxygen with methyl-substituted aromatic compounds in the presence of base, a cobalt, manganese, chromium or nickel salt catalyst and activated charcoal.Type: GrantFiled: September 7, 1982Date of Patent: June 5, 1984Assignee: The Dow Chemical CompanyInventors: Andrew T. Au, Chu W. Jung
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Patent number: 4429163Abstract: A 4-hydroxybenzaldehyde derivative of the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is selected from the group consisting of hydrogen atom, halogen atoms, lower alkyl groups or lower alkoxy groups, which is useful as intermediate for the production of medicines or agricultural chemicals, or as flavor, is produced by the reaction of a p-cresol derivative of the formula: ##STR2## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is as defined above, with oxygen or oxygen-containing gas in the presence of a base and a catalytic amount of cobalt compound or metallic cobalt.Type: GrantFiled: August 4, 1981Date of Patent: January 31, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Kanji Nishizawa, Kazuhiko Hamada, Tadatoshi Aratani
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Patent number: 4408070Abstract: Pure crystalline racemic sodium parahydroxymandelate free from any ions of chloride, acetate, formate and sulfate group, is manufactured by condensing in water, in the presence of sodium hydroxide at a temperature between 30.degree. and 100.degree. C., glyoxylic acid or sodium glyoxylate with an excess of phenol, concentrating it hot, until the start of crystallization of the solution thus obtained after neutralization and removal of the unconverted phenol either by steam distillation, or by extraction with a water-immiscible organic solvent. The resulting suspension obtained is cooled, drained after some hours of standing at a temperature close to 5.degree. C., and the resulting precipitate recovered by washing it with iced water followed by drying to constant weight. The product is useful for the manufacture of crystalline sodium paraformylphenolate.Type: GrantFiled: July 20, 1981Date of Patent: October 4, 1983Inventors: Alain Schouteeten, Yani Christidis
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Patent number: 4400541Abstract: Bis-(diphenylsulfoniophenyl)-sulfide-bis-chloride and related aryl sulfonium halides are produced in high yields and in high purity by reacting diphenyl disulfide (Ph--S--S--Ph) in benzene in the presence of aluminum chloride with gaseous chlorine according to the disclosed process.Type: GrantFiled: February 1, 1982Date of Patent: August 23, 1983Assignee: The Southland CorporationInventor: Shankar S. Iyer
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Patent number: 4366325Abstract: In a process for the preparation of 3-phenoxy-benzaldehyde by oxidation of 3-phenoxy-benzyl alcohol of the formula ##STR1## in which m represents a number from 1 to 4,n represents a number from 1 to 5 andR.sup.1 and R.sup.2 are identical or different and denote hydrogen, halogen, alkyl, cycloalkyl, aralkyl, alkoxy, cycloalkoxy, aryloxy or perfluoroalkyl,with an oxygen containing gas in aqueous alkali at a temperature from the solidification point to the boiling point of the reaction mixture in the presence of a platinum metal catalyst and in the presence of lead and/or bismuth and/or tellurium and/or a compound of said lead, bismuth or tellurium.Type: GrantFiled: October 8, 1980Date of Patent: December 28, 1982Assignee: Bayer AktiengesellschaftInventors: Karlfried Wedemeyer, Helmut Fiege
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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: 4351962Abstract: A process is provided for the preparation of hydroxy benzene carboxaldehydes having the formula: ##STR1## wherein: R is selected from the group consisting of alkyl, alkoxy, cycloalkyl, aryl, alkoxyalkyl, fluoroalkyl, and hydroxyalkyl oxyalkylene having from one to about twenty carbon atoms; hydroxyalkyl having at least two to about twenty carbon atoms; hydroxy; aldehyde CHO; and halogen;n.sub.1, n.sub.2 and n.sub.3 are zero or 1; and at least one of n.sub.1, n.sub.2 and n.sub.3 is 1; andx is zero, 1, 2, 3 or 4, which comprises:(1) condensing with a formaldehyde compound a phenol having the formula: ##STR2## wherein R is selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, cycloalkyl, aryl, alkoxyalkyl, fluoroalkyl, and hydroxyalkyl oxyalkylene having from one to about twenty carbon atoms; hydroxy; and halogen; andx is zero, 1, 2, 3 or 4,and unsubstituted in at least one ortho or para position in an aqueous reaction medium comprising phenol:HCHO in a molar ratio within the range from about 1:0.Type: GrantFiled: July 11, 1980Date of Patent: September 28, 1982Assignee: Rhone Poulenc Inc.Inventors: Peter S. Gradeff, Stanley T. Murayama
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Patent number: 4346238Abstract: Sodium paraformylphenolate crystallized with two molecules of water is manufactured by:(a) condensing glyoxylic acid with an excess of phenol in water in the presence of sodium hydroxide at a temperature comprised between 30.degree. C. and 100.degree. C.;(b) neutralizing the solution thus obtained and then freeing it from the unconverted phenol by steam distillation or extraction with a water-immiscible organic solvent and then subjecting it hot under a pressure of oxygen, to a catalytic decarboxylating oxidizing degradation in the presence of sodium hydroxide;(c) allowing the aqueous solution so-obtained, after removal of the catalyst by filtration, and then concentration hot under vacuum to 60% plus or minus 10% of its initial volume, to crystallize; and(d) draining the precipitated crystals, washing them and then drying them to constant weight under vacuum of 1 mm of mercury at 20.degree. C.Type: GrantFiled: May 7, 1980Date of Patent: August 24, 1982Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Yani Christidis
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Patent number: 4306083Abstract: In a two-phase liquid medium comprising an aqueous alkaline solution and an organic solvent, molecular oxygen and a noble metal-containing catalyst can be used to oxidize aryl-substituted alcohols of the formula AR(--CH.dbd.CH--).sub.n CH.sub.2 OH wherein n is 0, 1 or 2, to the corresponding aldehydes. More specifically, the oxidation of an aromatic alcohol, such as p-methoxybenzyl alcohol, can be efficiently carried out in a multiphase system comprising a 5 percent palladium-on-charcoal catalyst, an organic solvent such as methylene chloride, in contact with an aqueous sodium hydroxide solution, in the presence of air or oxygen with good agitation followed by separation of the two phases, recovery of the aldehyde product from the organic solvent and recycle of the aqueous phase without neutralization.Type: GrantFiled: May 15, 1980Date of Patent: December 15, 1981Assignee: The Dow Chemical CompanyInventor: King W. Ma
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Patent number: 4272634Abstract: A process for the production of alcohols and/or aldehydes which comprises subjecting a toluene derivative having an ether linkage or linkages of the general formula: ##STR1## wherein RO is an ether grouping where R stands for a hydrocarbyl group with 1.about.20 carbon atoms which may carry an inert substituent or substituents and n stands for an integer of 1.about.2, to auto-oxidation with molecular oxygen in liquid phase to form the corresponding alcohol and/or aldehyde, characterized in that the reaction is carried out by using a lower saturated fatty acid and/or an anhydride thereof as solvent in the presence of a soluble cobalt salt and a bromine ion-supplying substance at a reaction temperature ranging from 30.degree. C. to 200.degree. C. in such manner that the conversion rate of the toluene derivative does not exceed 90%.Type: GrantFiled: December 11, 1979Date of Patent: June 9, 1981Assignees: Director-General of Agency of Industrial Science and Technology, Sanko Chemical Co., Ltd., Nippon Soda Co., Ltd.Inventor: Juichi Imamura
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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: 4220605Abstract: A process for the production of alcohols and/or aldehydes which comprises subjecting a toluene derivative having an ether linkage or linkages of the general formula: ##STR1## wherein RO is an ether grouping where R stands for a hydrocarbyl group with 1.about.20 carbon atoms which may carry an inert substituent or substituents and n stands for an integer of 1.about.2, to auto-oxidation with molecular oxygen in liquid phase to form the corresponding alcohol and/or aldehyde, characterized in that the reaction is carried out by using a lower saturated fatty acid and/or an anhydride thereof as solvent in the presence of a soluble cobalt salt and a bromine ion-supplying substance at a reaction temperature ranging from 30.degree. C. to 200.degree. C. in such manner that the conversion rate of the toluene derivative does not exceed 90%.Type: GrantFiled: December 23, 1977Date of Patent: September 2, 1980Assignees: Director General of Agency of Industrial Science and Technology, Sanko Chemical Co. Ltd., Nippon Soda Co. Ltd.Inventor: Juichi Imamura
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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: 4205188Abstract: A process is provided for the production of hydroxybenzyl alcohols, comprising condensing phenol with formaldehyde in an alkaline solution to form a mixture of ortho- and para-hydroxymethyl phenols, and solvent extracting unreacted phenol from the resulting alkaline hydroxybenzyl alcohol condensate solution. The phenol-reduced hydroxybenzyl alcohol condensate solution is particularly suited for treatment with excess caustic and subsequent oxidation of the resulting aqueous solution of ortho- and para-hydroxybenzyl alcohols-sodium salt to yield the corresponding ortho- and para-hydroxybenzaldehydes-sodium salt.Type: GrantFiled: September 8, 1978Date of Patent: May 27, 1980Assignee: The Dow Chemical CompanyInventors: Wayne C. Muench, Thad S. Hormel, Pamela M. Kirchhoff, Lanny A. Robbins