Reactant Contains -coo- Group Patents (Class 568/435)
  • Patent number: 4987265
    Abstract: 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: Grant
    Filed: May 6, 1988
    Date of Patent: January 22, 1991
    Assignee: Stamicarbon B. V.
    Inventors: Paul C. Van Geem, Ludovicus H. W. Janssen
  • Patent number: 4973696
    Abstract: 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: Grant
    Filed: January 17, 1989
    Date of Patent: November 27, 1990
    Assignee: Zambon S.p.A.
    Inventors: Claudio Giordano, Graziano Castaldi, Silvia Cavicchioli, Francesco Minisci
  • Patent number: 4950799
    Abstract: 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: Grant
    Filed: May 15, 1989
    Date of Patent: August 21, 1990
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4933499
    Abstract: 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: Grant
    Filed: February 27, 1989
    Date of Patent: June 12, 1990
    Assignee: Shell Oil Company
    Inventors: Paul A. M. Grotenhuis, Brian L. Goodall
  • Patent number: 4915875
    Abstract: 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: Grant
    Filed: November 4, 1986
    Date of Patent: April 10, 1990
    Assignee: The Dow Chemical Company
    Inventors: Timothy R. Diephouse, Robert M. Strom
  • Patent number: 4782187
    Abstract: The preparation of 4,4'-stilbenedialdehydes from the corresponding acid chlorides in the presence of a noble metal catalyst.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: November 1, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Reinehr, Heinz Steiner
  • Patent number: 4613700
    Abstract: 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: Grant
    Filed: January 18, 1985
    Date of Patent: September 23, 1986
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Takao Maki, Toshiharu Yokoyama
  • Patent number: 4585900
    Abstract: 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: Grant
    Filed: January 22, 1985
    Date of Patent: April 29, 1986
    Assignee: Chem Systems Inc.
    Inventors: Norman L. Holy, Abraham P. Gelbein, Robert Hansen
  • Patent number: 4585899
    Abstract: 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: Grant
    Filed: January 22, 1985
    Date of Patent: April 29, 1986
    Assignee: Chem Systems Inc.
    Inventors: Abraham P. Gelbein, Robert Hansen
  • Patent number: 4568478
    Abstract: 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: Grant
    Filed: April 18, 1984
    Date of Patent: February 4, 1986
    Assignee: E. I. Dupont de Nemours and Company
    Inventors: William J. Middleton, Shlomo Rozen
  • Patent number: 4521630
    Abstract: 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: Grant
    Filed: August 9, 1983
    Date of Patent: June 4, 1985
    Assignee: Shell Oil Company
    Inventors: Freddy Wattimena, Hendricus J. Heijmen
  • Patent number: 4504671
    Abstract: 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: Grant
    Filed: October 15, 1982
    Date of Patent: March 12, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
  • Patent number: 4490559
    Abstract: 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: Grant
    Filed: March 27, 1984
    Date of Patent: December 25, 1984
    Assignee: Shell Oil Company
    Inventors: Richard W. Wegman, John B. Letts
  • Patent number: 4465833
    Abstract: 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: Grant
    Filed: October 15, 1980
    Date of Patent: August 14, 1984
    Assignees: Hughes Aircraft Company, Hughes Aircraft Company
    Inventors: Kreisler S. Y. Lau, Robert H. Boschan
  • Patent number: 4418206
    Abstract: 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: Grant
    Filed: March 22, 1982
    Date of Patent: November 29, 1983
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Douglas L. Wren
  • Patent number: 4408070
    Abstract: 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: Grant
    Filed: July 20, 1981
    Date of Patent: October 4, 1983
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 4394314
    Abstract: 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: Grant
    Filed: April 23, 1981
    Date of Patent: July 19, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Wallace C. Petersen
  • Patent number: 4389527
    Abstract: 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: Grant
    Filed: June 30, 1981
    Date of Patent: June 21, 1983
    Assignee: Givaudan Corporation
    Inventors: Roy H. Valentine, Harold A. Brandman
  • Patent number: 4346238
    Abstract: 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: Grant
    Filed: May 7, 1980
    Date of Patent: August 24, 1982
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 4328373
    Abstract: 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: Grant
    Filed: March 17, 1980
    Date of Patent: May 4, 1982
    Assignee: The Dow Chemical Company
    Inventor: Edwin J. Strojny
  • Patent number: 4271323
    Abstract: 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: Grant
    Filed: October 10, 1975
    Date of Patent: June 2, 1981
    Assignee: Institut Francais du Petrole
    Inventors: Daniel Durand, Gerard Hillion, Christian Lassau, Lucien Sajus
  • Patent number: 4252738
    Abstract: 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: Grant
    Filed: March 17, 1978
    Date of Patent: February 24, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Willy Hartmann, Hans-Georg Heine
  • Patent number: 4240984
    Abstract: 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: Grant
    Filed: January 18, 1979
    Date of Patent: December 23, 1980
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Paolo deWitt, Maria O. Tinti
  • Patent number: 4239702
    Abstract: 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: Grant
    Filed: January 18, 1979
    Date of Patent: December 16, 1980
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Paolo deWitt, Maria O. Tinti
  • Patent number: 4229380
    Abstract: 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: Grant
    Filed: July 17, 1978
    Date of Patent: October 21, 1980
    Assignee: Shell Oil Company
    Inventors: Edgar J. Smutny, Thomas H. Colby
  • Patent number: 4206152
    Abstract: 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: Grant
    Filed: December 21, 1978
    Date of Patent: June 3, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Jacques Gosteli
  • Patent number: 4202822
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: May 13, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner