Reactant Contains -coo- Group Patents (Class 568/435)
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Patent number: 4987265Abstract: The invention relates to the preparation of a benzaldehyde by hydrogenation of a corresponding benzoic acid in the gas phase in the presence of a manganese containing catalyst on an acid carrier. The invention is characterized in that use is made of a catalyst prepared by:(a) coprecipitation, at a pH between 7 and 10, of a manganese salt and a salt from which an acid carrier is formed,(b) subsequent calcination at a temperature between 300.degree. and 700.degree. C.,(c) followed by reduction with a hydrogen containing gas mixture.Preferably the catalyst contains oxides of aluminum, zirconium, titanium, hafnium and/or niobium.Type: GrantFiled: May 6, 1988Date of Patent: January 22, 1991Assignee: Stamicarbon B. V.Inventors: Paul C. Van Geem, Ludovicus H. W. Janssen
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Patent number: 4973696Abstract: A stereoselective process is described for preparing optically active alpha,beta-disubstituted carbonyl compounds, comprising forming an acetal between an alpha,beta-unsaturated aldehyde or ketone and tartaric acid or a derivative thereof, halogenating the product thus obtained, and restoring the carbonyl compound.Type: GrantFiled: January 17, 1989Date of Patent: November 27, 1990Assignee: Zambon S.p.A.Inventors: Claudio Giordano, Graziano Castaldi, Silvia Cavicchioli, Francesco Minisci
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Patent number: 4950799Abstract: Monocarboxylic acids or esters thereof are reduced to aldehydes using hydrogen and a vanadium catalyst. For example, meta-phenoxybenzoic acid can be effectively converted to meta-phenoxybenzaldehyde in a vapor phase process using hydrogen as the carrier gas/reductant and a catalyst composed at least initially of vanadium pentoxide, either supported or unsupported.Type: GrantFiled: May 15, 1989Date of Patent: August 21, 1990Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4933499Abstract: The invention relates to a process for the purification of alkenyl aromatic compounds which contain benzaldehyde as an impurity. This process comprises steps for contacting a benaldehyde-containing alkenyl aromatic compound with a bisulphite treating agent, and separating the resulting benzaldehyde-bisulphite addition product from the alkenyl aromatic compound. In certain preferred embodiments, the treating agent is a modified anion-exchange resin containing bound bisulphite ions. Optionally, the process then further comprises a step for recovering the benzaldehyde from the resin addition product by contact with an aqueous sodium carbonate solution or by steam distillation.Type: GrantFiled: February 27, 1989Date of Patent: June 12, 1990Assignee: Shell Oil CompanyInventors: Paul A. M. Grotenhuis, Brian L. Goodall
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Patent number: 4915875Abstract: Paramethyl-substituted hindered phenols are selectively oxidized by contacting with an oxidizing agent at elevated temperatures in the presence of a heterogeneous oxidative coupling catalyst. In the absence of an optional nucleophile the products comprise carbon-carbon oxidative coupling products. In the presence of a nucleophile, addition products result that may be further oxidized by continued exposure to the oxidizing agent to yield substituted p-hydroxybenzaldehydes.Type: GrantFiled: November 4, 1986Date of Patent: April 10, 1990Assignee: The Dow Chemical CompanyInventors: Timothy R. Diephouse, Robert M. Strom
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Patent number: 4782187Abstract: The preparation of 4,4'-stilbenedialdehydes from the corresponding acid chlorides in the presence of a noble metal catalyst.Type: GrantFiled: December 10, 1986Date of Patent: November 1, 1988Assignee: Ciba-Geigy CorporationInventors: Dieter Reinehr, Heinz Steiner
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Patent number: 4613700Abstract: An improved process for catalytic hydrogenation of aromatic carboxylic acids to produce aromatic aldehydes is described, using a catalyst comprising zirconium oxide containing as an essential component at least one element selected from the group consisting of chromium, manganese, iron, cobalt, zinc, bismuth, lead, rhenium and the elements of Group III of periods 3 to 6 of the periodic table; the process results in improved catalyst activity and produces the desired aromatic aldehydes in high yield.Type: GrantFiled: January 18, 1985Date of Patent: September 23, 1986Assignee: Mitsubishi Chemical Industries LimitedInventors: Takao Maki, Toshiharu Yokoyama
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Patent number: 4585900Abstract: A process for selectively forming aldehydes which comprises hydrogenating a carboxylic acid or a carboxylic acid ester in the presence of an yttrium catalyst activated with copper.Type: GrantFiled: January 22, 1985Date of Patent: April 29, 1986Assignee: Chem Systems Inc.Inventors: Norman L. Holy, Abraham P. Gelbein, Robert Hansen
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Hydrogenation of carboxylic acid compounds to aldehydes using MnO.sub.2 on gamma alumina as catalyst
Patent number: 4585899Abstract: A process for selectively forming aldehydes which comprises hydrogenating a carboxylic acid or a carboxylic acid ester in the presence of a manganese catalyst supported on an activated alumina.Type: GrantFiled: January 22, 1985Date of Patent: April 29, 1986Assignee: Chem Systems Inc.Inventors: Abraham P. Gelbein, Robert Hansen -
Patent number: 4568478Abstract: There is disclosed a solution of at least one fluoroxy compound, wherein said solution has a fluoroxy compound concentration of at least 0.5 meq/liter; said concentration containing about 35 to 100% of an acyl hypofluorite, based on the total number of equivalents of fluoroxy compounds present. The acyl hypofluorite has the formula X(CF.sub.2).sub.n COOF wherein X is H or F and n is 5 to 16. The solution is prepared by treating a suspension of a corresponding specified alkali salt with excess F.sub.2, and is useful as a selective fluorinating agent.Type: GrantFiled: April 18, 1984Date of Patent: February 4, 1986Assignee: E. I. Dupont de Nemours and CompanyInventors: William J. Middleton, Shlomo Rozen
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Patent number: 4521630Abstract: Aldehydes are prepared by hydrogenating a compound of general formula R'COOR, wherein R represents a hydrogen atom, an alkyl or an acyl group, or a metal, and R' represents an optionally substituted hydrocarbyl group having at most two alpha-hydrogen atoms, provided it has at most one beta-hydrogen atom, in case it has two alpha-hydrogen atoms, in the presence of a catalyst comprising at least one metal selected from rare earth metals and iron on an alumina-based carrier.Type: GrantFiled: August 9, 1983Date of Patent: June 4, 1985Assignee: Shell Oil CompanyInventors: Freddy Wattimena, Hendricus J. Heijmen
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Patent number: 4504671Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.Type: GrantFiled: October 15, 1982Date of Patent: March 12, 1985Assignee: PPG Industries, Inc.Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
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Patent number: 4490559Abstract: Saturated aliphatic aldehydes are prepared by contacting diesters of carbonic acid with synthesis gas and a Group VIII compound, preferably a cobalt compound, a halogen, and optionally a Group V trivalent ligand.Type: GrantFiled: March 27, 1984Date of Patent: December 25, 1984Assignee: Shell Oil CompanyInventors: Richard W. Wegman, John B. Letts
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Patent number: 4465833Abstract: A novel ethynylation process is disclosed which provides an expanded series of novel ethylnyl-terminated aromatic compounds having base sensitive substituents and which facilitates the economic preparation of prior art ethynyl-substituted aromatic compounds.Type: GrantFiled: October 15, 1980Date of Patent: August 14, 1984Assignees: Hughes Aircraft Company, Hughes Aircraft CompanyInventors: Kreisler S. Y. Lau, Robert H. Boschan
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9-Deoxy-9-methylene derivatives of (dl)-16-phenoxy and 16-phenoxy substituted prostatriene compounds
Patent number: 4418206Abstract: Novel compounds of the formula: ##STR1## wherein A is CHOH, CHO or COOR; R is hydrogen or a lower alkyl group of 1 to 4 carbon atoms; and the pharmaceutically acceptable, non-toxic salts of compounds in which R is hydrogen; and X is hydrogen, o-, m- or p-halo(fluoro, chloro or bromo), o-, m- or p-methyl or o-, m- or p-methoxy. These compounds possess prostaglandin-like activity and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretions and as agents for the control of asthmatic attack, because of their bronchodilating activity.Type: GrantFiled: March 22, 1982Date of Patent: November 29, 1983Assignee: Syntex (U.S.A.) Inc.Inventor: Douglas L. Wren -
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: 4394314Abstract: A process of reacting a ring carbon atom of an aromatic compound Ar with a compound of the formula H.sub.2 NCH.dbd.NH.sub.2.sup.+ CH.sub.3 CO.sub.2.sup.-, and an anhydride which has the ##STR1## at from 10.degree. to 200.degree. C. and preferably 25.degree. to 40.degree. C. to form a compound of the formula ##STR2## where m is 1, 2 or 3, and A is H or F. In the case where m is 1 the compound ##STR3## can be hydrolyzed to ArCHO.Type: GrantFiled: April 23, 1981Date of Patent: July 19, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Wallace C. Petersen
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Patent number: 4389527Abstract: This invention discloses a novel process for producing dihydrocinnamaldehyde derivatives which comprises reacting a benzene derivative with an alken-2-ylidene diacylate or an .alpha.-ethylenic aldehyde in trifluoroacetic acid (TFA).Type: GrantFiled: June 30, 1981Date of Patent: June 21, 1983Assignee: Givaudan CorporationInventors: Roy H. Valentine, Harold A. Brandman
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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: 4328373Abstract: An improved vapor phase process for producing aldehydes from corresponding carboxylic acids and esters of said carboxylic acids by contacting the acid or ester at temperatures from about 300.degree. C. to about 500.degree. C. with hydrogen, in the presence of a catalyst selected from certain metal oxides.Type: GrantFiled: March 17, 1980Date of Patent: May 4, 1982Assignee: The Dow Chemical CompanyInventor: Edwin J. Strojny
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Patent number: 4271323Abstract: Process for hydrogenating unsaturated compounds in the liquid phase in the presence of a soluble catalyst obtained by reacting an organometal derivative or a metal hydride with a synergistic mixture of (a) a compound of zinc, zirconium, manganese, molybdenum, or iron and (b) a nickel or cobalt compound.Type: GrantFiled: October 10, 1975Date of Patent: June 2, 1981Assignee: Institut Francais du PetroleInventors: Daniel Durand, Gerard Hillion, Christian Lassau, Lucien Sajus
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Patent number: 4252738Abstract: 1,2-Halohydrincarboxylic acid esters of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are identical or different and represent hydrogen, cyano and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxycarbonyl, acyloxy, alkoxy and aryloxy, and furthermoreR.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, or R.sup.1 and R.sup.3 and/or R.sup.2 and R.sup.4 can be linked, forming a ring with the carbon atoms to which they are bonded;R.sup.5 represents hydrogen and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxy and alkoxycarbonyl andX represents fluorine, chlorine, bromine and iodine; a process for preparing such 1,2-halohydrincarboxylic acid esters by reacting a cyclobutane-cis-1,2-diol of the formula ##STR2## with an orthoester of the formula ##STR3## wherein R.sup.1 -R.sup.5 have the previously ascribed significance and R.sup.6 -R.sup.Type: GrantFiled: March 17, 1978Date of Patent: February 24, 1981Assignee: Bayer AktiengesellschaftInventors: Willy Hartmann, Hans-Georg Heine
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Patent number: 4240984Abstract: A process for preparing aromatic aldehydes starting from the corresponding aromatic acid, comprising two steps, the first one consisting of the reaction of said acid with ethyl or isobutyl chlorocarbonate to obtain the corresponding anhydride, and the second one to hydrogenate the thus-obtained anhydride to yield to aldehyde.Type: GrantFiled: January 18, 1979Date of Patent: December 23, 1980Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Paolo deWitt, Maria O. Tinti
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Patent number: 4239702Abstract: Process for the production of aromatic alcohol and aldehydes comprising three steps, the first one consisting of reacting an aromatic acid with ethyl or isobutyl chloroformiate to obtain the corresponding mixed anhydride, the second one consisting of the hydrogenation of the mixed anhydride to obtain the corresponding benzyl alcohol, and the third one consisting of the oxidation of the alcohol to the corresponding aldehyde.Type: GrantFiled: January 18, 1979Date of Patent: December 16, 1980Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Paolo deWitt, Maria O. Tinti
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Patent number: 4229380Abstract: 3-Phenoxybenzaldehyde is prepared by adding, at a relatively low temperature, a mixture of a 3-phenoxybenzyl halide and a 3-phenoxybenzal halide to a mixture of hexamethylenetetramine, acetic acid and water, the amounts of the water and acid bearing certain relationships to the amount of the mixture of halides, then heating the resulting mixture to a specified temperature level and maintaining it at that level for a specified period of time.Type: GrantFiled: July 17, 1978Date of Patent: October 21, 1980Assignee: Shell Oil CompanyInventors: Edgar J. Smutny, Thomas H. Colby
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Patent number: 4206152Abstract: The present invention provides a process for the production of unsubstituted or substituted o-phthalaldehydes by hydrolysis of .alpha.,.alpha., .alpha.',.alpha.'-tetrahalogeno-o-xylenes with a carboxylate in an aqueous medium in the presence of a phase transfer catalyst and an organic base.Type: GrantFiled: December 21, 1978Date of Patent: June 3, 1980Assignee: Ciba-Geigy CorporationInventor: Jacques Gosteli
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner