Aldehydes Patents (Class 568/420)
  • Patent number: 6121498
    Abstract: A method of producing acetaldehyde hydrogenates acetic acid in the presence of an iron oxide catalyst containing between 2.5 and 90 wt % Pd, more preferably 10 and 80 wt % Pd and most preferably 20 and 60 wt % Pd. The catalyst has a specific surface area of less than 150 m.sup.2 /g. Hydrogen and acetic acid are fed to a reactor in a hydrogen to acetic acid ratio of 2:1 to 25:1, more preferably in a hydrogen to acetic acid ratio of 3:1 to 15:1 and most preferably in a hydrogen to acetic acid ratio of 4:1 to 12:1. The hydrogenation is performed at a temperature of about 250.degree. C. to 400.degree. C., more preferably about 270.degree. C. to 350.degree. C. and most preferably about 280.degree. C. to 325.degree. C. The hydrogenation of acetic acid produces a partially gaseous product, and acetaldehyde is absorbed from the partially gaseous product with a solvent containing acetic acid. The gas remaining after the absorption step contains hydrogen, and this gas is recycled for the hydrogenation of acetic acid.
    Type: Grant
    Filed: April 30, 1998
    Date of Patent: September 19, 2000
    Assignee: Eastman Chemical Company
    Inventors: Gerald C. Tustin, Leslie S. Depew, Nick A. Collins
  • Patent number: 5912389
    Abstract: A stabilizer for an aqueous aliphatic aldehyde solution comprising acetic acid, a halogenated acetic acid or a compound capable of releasing acetic acid or a halogenated acetic acid in water.
    Type: Grant
    Filed: October 14, 1997
    Date of Patent: June 15, 1999
    Assignee: Katayama Chemical, Inc.
    Inventor: Shinichi Matsumoto
  • Patent number: 5910613
    Abstract: A process for producing aromatic aldehydes by carbonylation of an arene in the presence of triflic acid catalyst is described by reacting an arene, such as toluene, with carbon monoxide in the presence of triflic acid (as a catalyst), for a reaction time less than 90 minutes, at a carbon monoxide partial pressure of about 700-2000 psig, at a temperature of from about 0-50.degree. C. to produce an aromatic aldehyde such as tolualdehyde and by-products, the by-products being less than 5% by weight based on the total reaction products.The mole ratio of triflic acid to arene is between about 0.8 to 20, with the reaction having an isomer selectivity greater than 95% by weight for the para isomer aldehyde, and showing substantially no meta isomer.
    Type: Grant
    Filed: May 6, 1998
    Date of Patent: June 8, 1999
    Assignee: HNA Holdings, Inc.
    Inventors: David Anthony Schiraldi, Jeffrey Charles Kenvin
  • Patent number: 5902896
    Abstract: A process for preparing bis(hydroxymethyl) compounds of the formula (I) ##STR1## wherein X.sup.1 and X.sup.2 represent identical or different electronegative groups, which process entails reacting C--H-acidic compounds of the formula (II) ##STR2## wherein X.sup.1 and X.sup.2 are as defined above, with formaldehyde, wherein the reaction is carried out in an anhydrous medium.
    Type: Grant
    Filed: March 20, 1998
    Date of Patent: May 11, 1999
    Assignee: Huels Aktiengesellschaft
    Inventor: Frank Bauer
  • Patent number: 5877381
    Abstract: The present invention provides a fluidized bed catalyst for the synthetic reaction of organic compounds which has a reduced catalyst loss. A fluidized bed catalyst for organic compound synthetic reaction, characterized in that 90% or more of the catalyst particles is in the range of 5-500 .mu.m on the weight-based particle size distribution and 90% or more of the 20-75 .mu.m particles has a crushing strength which satisfies the following equation:CS>A.multidot.d.sub..alpha.wherein CS represents a crushing strength ?g-weight/particle!,A represents a constant 0.001,d represents a particle diameter ?.mu.m!, and.alpha. represents a constant 2.
    Type: Grant
    Filed: July 1, 1996
    Date of Patent: March 2, 1999
    Assignee: Nitto Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yutaka Sasaki, Hiroshi Yamamoto, Kiyoshi Moriya, Yoshimi Nakamura
  • Patent number: 5858738
    Abstract: Natural products such as certain ermophilane sesquiterpenoids and derivatives thereof are described. These compounds are useful in the inhibition of HIV integrase, the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described. The fungal culture MF6254, Xylaria sp. (ATCC 74397) is also described and disclosed.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: January 12, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Russell B. Lingham, Jon David Polishook, Ali Shafiee, Keith C. Silverman, Sheo Bux Singh, Deborah L. Zink
  • Patent number: 5831135
    Abstract: The present invention relates to a process for the catalytic selective hydrogenation of a polyunsaturated organic compound, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding the polyunsaturated organic compound and hydrogen to an upper part of a reactor to catalytically hydrogenate said the polyunsaturated organic compound to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein the polyunsaturated organic compound is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating step
    Type: Grant
    Filed: October 6, 1997
    Date of Patent: November 3, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Wilfried Bueschken, Juergen Hummel
  • Patent number: 5705706
    Abstract: 2-(Alkoxymethyl)acrolein of the formula ##STR1## is produced from acrolein, an alcohol ROH and formaldehyde, in one step, with a good yield being obtained. The acrolein is reacted with a substantially equimolar quantity of a source of formaldehyde in the presence of at least an equimolar quantity of the alcohol ROH and a catalytic quantity of a catalyst system based on a secondary amine and a mineral acid at a pH value of the reaction mixture in the range of 1 to less than 7.
    Type: Grant
    Filed: July 23, 1996
    Date of Patent: January 6, 1998
    Assignee: Degussa Aktiengesellschaft
    Inventors: Mathias Hoepp, Klaus Koehler, Dietrich Arntz
  • Patent number: 5705705
    Abstract: A process for the oxidation of alkylaromatic compounds is provided. The process comprises oxidizing a substrate alkylaromatic compound with a peroxygen compound in the presence of a source of cerium (III) or (IV), a source of bromide and a carboxylic acid or anhydride solvent. Preferably, the source of cerium is cerium (III) acetate, the source of bromide is sodium bromide and the solvent is acetic or propionic acid. The process is particularly suited to the selective oxidation of methylaromatic compounds to the corresponding aldehydes.
    Type: Grant
    Filed: March 26, 1996
    Date of Patent: January 6, 1998
    Assignee: Solvay Interox Limited
    Inventors: Scott William Brown, Kevin Auty
  • Patent number: 5675045
    Abstract: The present invention relates to a process for the catalytic selective hydrogenation of a polyunsaturated organic compound, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding the polyunsaturated organic compound and hydrogen to an upper part of a reactor to catalytically hydrogenate said the polyunsaturated organic compound to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein the polyunsaturated organic compound is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating step
    Type: Grant
    Filed: June 26, 1996
    Date of Patent: October 7, 1997
    Assignee: Huels Aktiengesellschaft
    Inventors: Wilfried Bueschken, Juergen Hummel
  • Patent number: 5667644
    Abstract: A method for producing a dimerized aldehyde, which comprises subjecting a feed aldehyde to a condensation reaction and a dehydration reaction in the presence of a basic catalyst, wherein the feed aldehyde is the one having one or two hydrogen atoms at the .alpha.-position, an organic feed stream containing the feed aldehyde is supplied to a reactive distillation column, and the condensation reaction and the dehydration reaction are carried out simultaneously in the reactive distillation column.
    Type: Grant
    Filed: February 9, 1996
    Date of Patent: September 16, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tomoyuki Mori, Kouichi Fujita, Yuuji Kajita, Masaki Takai
  • Patent number: 5648387
    Abstract: Dialkyl ethers lower Lp(a) and triglycerides, and elevate HDL-cholesterol, and are thereby useful for treating vascular diseases and noninsulin-dependent diabetes mellitus.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: July 15, 1997
    Assignee: Warner-Lambert Company
    Inventors: Charles Larry Bisgaier, Paul Leroy Creger, Alan Robert Saltiel, Sherrie Rae Tafuri
  • Patent number: 5585523
    Abstract: Process for the preparation of aldehydes by catalytic gas phase hydrogenation of carboxylic acid or their derivatives with the aid of a tin catalystThe invention relates to a process for the preparation of aldehydes by catalytic gas phase hydrogenation of carboxylic acids or carboxylic acid derivatives at elevated temperature, which comprises employing at tin catalyst supplied to an oxidic support material.
    Type: Grant
    Filed: September 6, 1995
    Date of Patent: December 17, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jens Weiguny, Holger Borchert, Thomas Gerdau
  • Patent number: 5510538
    Abstract: A process for the selective oxidation of a primary or secondary alcohol to an aldehyde or ketone and for the oxidation of a 1,2-diol to an .alpha.-ketol or .alpha.-diketone, which comprises contacting the alcohol or 1,2-diol with o-iodoxybenzoic acid. This process is suited for selective oxidation of alcohols containing easily oxidizable groups, such as amino or thioether groups and easily oxidizable heterocycles.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: April 23, 1996
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Marco Frigerio, Simona Sputore, Marco Santagostino
  • Patent number: 5471003
    Abstract: Disclosed is a process for the removal of crotonaldehyde impurity from cyclopropanecarboxaldehyde by the selective, catalytic hydrogenation of crotonaldehyde to butyraldehyde followed by distillation of the butyraldehyde from the cyclopropanecarboxaldehyde.
    Type: Grant
    Filed: November 28, 1994
    Date of Patent: November 28, 1995
    Assignee: Eastman Chemical Company
    Inventor: Shaowo Liang
  • Patent number: 5376746
    Abstract: A two-part initiator system useful in acrylic adhesive compositions comprising in one part a stable organoboron amine complex and in the second part an aldehyde destabilizer or activator. This initiator is particularly useful in elastomeric acrylic adhesive compositions and provides room temperature, relatively slow curing systems with good adhesive properties making them useful in applications where longer open times are required.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: December 27, 1994
    Assignee: National Starch and Chemical Investment Holding Corporation
    Inventor: Martin M. Skoultchi
  • Patent number: 5352840
    Abstract: Substituting aqueous hydrogen peroxide/hydrogen bromide for bromine in a known process for producing a ditertiaryalkyl substituted hydroxybenzaldehyde such as ditertiarybutyl hydroxybenzaldehyde from the corresponding ditertiaryalkyl substituted methylphenol results in a substantially impaired yield of product.Improved yields are obtained by employing a reaction temperature of at least 40.degree. C., preferably 50.degree. to 80.degree. C. in conjunction with a hydrophobic solvent such as chloroform. Preferably, the process employs very concentrated hydrogen peroxide solution, 65% to 75% w/w, introduced into the bromide-containing reaction mixture during a period of from 25 to 75 minutes.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: October 4, 1994
    Assignee: Solvay Interox Limited
    Inventors: Stephen G. Grundy, Kevan M. Reeve, Michael C. Rocca
  • Patent number: 5352822
    Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: October 4, 1994
    Assignee: Roussel Uclaf
    Inventors: Robert J. Blade, George S. Cockerill, John E. Robinson
  • Patent number: 5326748
    Abstract: The invention relates to compounds of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines. Compounds (I) are useful as perfuming ingredients for the preparation of perfuming compositions and perfuming articles, to which they impart sandalwood-animal notes.
    Type: Grant
    Filed: May 10, 1993
    Date of Patent: July 5, 1994
    Assignee: Firmenich SA
    Inventor: Christian Chapuis
  • Patent number: 5278338
    Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventor: Rhonda L. Trace
  • Patent number: 5227530
    Abstract: Conversion of alcohol to organic compounds which comprises contacting the alcohol with a heterogeneous catalyst composition comprising crystallineCu.sub.2-X Cr.sub.y Al.sub.6-y B.sub.4 O.sub.17 M.sub.m M'.sub.nwhere M is a divalent metal, M' is a monovalent metal, m is a number in a range from 0 to 0.8, n is a number in a range from 0 to 1.6, X is a number in a range from 0 to 10 0.8 and is equal to the sum of m and n/2, and y is a number in a range from 0.01 to 3, having a characteristic X-ray diffraction pattern.
    Type: Grant
    Filed: March 24, 1992
    Date of Patent: July 13, 1993
    Assignee: Amoco Corporation
    Inventors: Larry C. Satek, Patrick E. McMahon
  • Patent number: 5210317
    Abstract: Disclosed is a method of producing an aldehyde in which a primary alcohol is reacted with an oxidizing agent selected from the group consisting of ketone, aldehyde and quinone in the presence of a diluent which does not participate in the reaction, in the presence of a partially dehydrated zirconium hydroxide, so as to oxidize the primary alcohol into its corresponding aldehyde.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: May 11, 1993
    Assignee: Japan Tobacco Inc.
    Inventors: Hideyuki Kuno, Makoto Shibagaki, Kyoko Takahashi, Hajime Matsushita
  • Patent number: 5208388
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5206442
    Abstract: The preparation of .alpha.,.beta.-unsaturated aldehydes and ketones IO.dbd.C(R.sup.1)--CR.sup.2 .dbd.CR.sup.3 R.sup.4 Iis carried out by acid hydrolysis of cyclic .alpha.,.beta.-unsaturated acetals II ##STR1## in the presence of saturated aldehydes.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: April 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Christiane Mackenroth, Ernst Buschmann
  • Patent number: 5202497
    Abstract: The invention relates to a process for preparing unsaturated aldehydes and their enamines by the oxidation of allylic tertiary amines in the presence of an alkyl hydroperoxide and a vanadium-based catalyst.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: April 13, 1993
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Serge Henrot
  • Patent number: 5177266
    Abstract: There is provided a process for the manufacture of 2-alkoxymethylacrolein compounds via the reaction of an appropriate alcohol and acrolein in the presence of an acid and a trisubstituted amine to form an intermediate and the subsequent reaction of the intermediate with formaldehyde in the presence of an acid and a disubstituted amine.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: January 5, 1993
    Assignee: American Cyanamid Company
    Inventor: Henry L. Strong
  • Patent number: 5175373
    Abstract: A process for preparing cyclocitral by expoxidizing a pyronene.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: December 29, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Bernard Delmond, Claude Filliatre, Michel Pereyre, Dominique Serramedan
  • Patent number: 5171894
    Abstract: The method uses a starting material which is a liquid mixture including a formaldehyde proportion between 48 to 55% by weight, a methanol proportion between 20 and 30% by weight and a water proportion between 32 and 15 wt %; the liquid mixture is obtained from a tapping which is effected from a plant for the continuous preparation of urea-formaldehyde resins and glues, immediately after having subjected the methanol to catalytic oxidation via air, condensation of the gases evolving from said catalytic oxidation and separation between condensed products and uncondensed gases. These solutions may be applied to formaldehyde reactions wherein it is of interest to reduce the amount of water present in conventional solutions and also to use the methanol for example as solvent for the final product obtained.
    Type: Grant
    Filed: January 2, 1991
    Date of Patent: December 15, 1992
    Assignee: Patenes y Novedades
    Inventor: Luis E. Vancells
  • Patent number: 5128317
    Abstract: Described are camphonyl spirocyclooxaoctane-containing compositions having the generic structures: ##STR1## and mixtures of same with substituted cyclopentenyl-oxabicyclooctanes defined according to the generic structures: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 ' and R.sub.3 " each represents hydrogen or methyl and R.sub.4 ' represents hydrogen or C.sub.1 -C.sub.5 alkyl, processes for preparing same and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles, e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic preparations, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.
    Type: Grant
    Filed: July 25, 1991
    Date of Patent: July 7, 1992
    Assignee: International Flavors and Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, Carlos Benaim, Anton Van Ouwerkerk, Olivier Gillotin
  • Patent number: 5126490
    Abstract: A process is disclosed for the catalytic oxydation of olefins to carbonyl compounds with molecular oxygen at elevated temperatures in the presence of rhodium oxide on a support. The process is applicable to a broad variety of olefins and is not limited to special olefins and forms especially ketones in a high selectivity.
    Type: Grant
    Filed: November 28, 1990
    Date of Patent: June 30, 1992
    Assignee: Princeton University
    Inventors: Jeffrey Schwartz, H. Eric Fischer, Jeffrey W. McMillan
  • Patent number: 5113003
    Abstract: The silicon-containing phenoxy ethers are of the formula III: ##STR1## wherein R.sup.1 and R.sup.2 which may be the same or different are selected from H, --R.sup.3 --X, aliphatic hydrocarbyl having 1-6 carbon atoms or aryl, or substituted derivatives thereof, provided that not more than one of R.sup.1 and R.sup.2 is H;R.sup.3 is a divalent C.sub.1 -C.sub.30 aliphatic and/or aromatic hydrocarbyl group which may optionally be substituted, or interrupted, by a hetero atom;R.sup.4 and R.sup.5 which may be the same or different are H, ##STR2## or an ortho para directing activating group for aromatic electrophilic substitution, other than an amine;and X is a reactive functional group capable of undergoing an acid-catalyzed electrophilic aromatic substitution reaction with a phenol, for example an aldehyde group. They can be polymerized to produce silicone-modified polymers of the phenol-aldehyde type without the use of free aldehyde.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: May 12, 1992
    Assignee: Loctite (Ireland) Limited
    Inventors: John G. Woods, Pauline Coakley
  • Patent number: 5103065
    Abstract: Transition metal complexes of the general formula I[A].sup.x- [Q].sup.+ x Iwhere Q is one equivalent of a cation, x is from 0 to 2 and A is a transition metal complex of the general formula ##STR1## where n is from 1 to 3, M is positively charged cobalt, rhodium, iridium or ruthenium, the ligands B are phosphonic, arsonic, phosphinic and/or arsinic acid ligands which are esterified with identical or different alcohols, one or more of these alcohol components carrying a functional group, L is ##STR2## the radicals R.sup.5 are identical or different radicals from the group consisting of C.sub.1 -C.sub.4 -alkyl and phenyl, p is an integer from 0 to 6, q is an integer from 0 to 5, and R.sup.1 is fluorine, chlorine, bromine, iodine, cyanide, isocyanide, cyanate, isocyanate, thiocyanate, isothiocyanate, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: April 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Bertleff, Dieter Koeffer, Wolfgang Klaeui, Choong-Eui Song
  • Patent number: 5095147
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5077043
    Abstract: The present invention provides mainly (3Z,6Z)-cis-9,10-epoxy-1,3,6-heneicosatriene (formula 1) and (3Z, 6Z)-cis-9,10-epoxy-1,3,6-elcosatriene (formula 2) which are Hyphantria cunea sex pheromones. The invention provides attractant components having high attraction effect for Hyphantria cunea, that is, Hyphantria cumea sex pheromones having high attraction activity and the intermediates which can selectively synthesize such pheromones with great ease.Furthermore, the invention provides attractant compositions with high attraction effect for Hyphantria cunea including such above noted pheromones.Consequently, this invention is completed.
    Type: Grant
    Filed: June 11, 1990
    Date of Patent: December 31, 1991
    Assignees: Nitto Denko Co. Ltd., Fuji Yakuhin Kogyo Kabushiki Kaisha
    Inventors: Miklos Toth, Hans-Rudolf Buser, Heinrich Arn, Kenji Mori, Yasuo Ninomiya, Tetsuo Omata, Shuji Senda, Tadashi Takeuchi, Masakazu Aburatani
  • Patent number: 5053550
    Abstract: Formylcyclopropane (I) ##STR1## is prepared by cyclization of 4-chlorobutanal by means of an aqueous mineral base by a method in which the reaction is carried out at 50.degree.-150.degree. C. in a liquid two-phase system consisting of an aqueous phase and a water-immiscible organic phase, and the formylcyclopropane is removed continuously from the reaction mixture.
    Type: Grant
    Filed: June 4, 1990
    Date of Patent: October 1, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Kuekenhoener, Norbert Goetz
  • Patent number: 5043480
    Abstract: A process for producing a .beta.-hydroxyester product or a .beta.-hydroxyaldehyde product from ethylene oxide, carbon monoxide, and, optionally, hydrogen, is disclosed. This process uses, as a catalyst, a catalyst comprising rhodium, ruthenium, and a Group Va promoter.
    Type: Grant
    Filed: August 16, 1990
    Date of Patent: August 27, 1991
    Assignee: Eastman Kodak Company
    Inventor: William A. Beavers
  • Patent number: 5021602
    Abstract: Novel compounds have at least one perfluorocyclobutane ring and at least two functional groups suitable for forming condensation polymers. Preferably the compounds have a structures represented by Formula II: ##STR1## wherein R and R' independently represent optionally inertly substituted groups; X and X' represent any molecular structures which link R and R' with the perfluorocyclobutane ring; n and n' are the number of G and G' groups, respectively; and G and G' independently represent any reactive functional groups or any groups convertible into reactive functional groups. The compound are preferably prepared by a process of thermally dimerizing trifluorovinyl compound to form a compounds of Formula IG.sub.n --R--X--CF.dbd.CF.sub.2wherein G represents G or G' in Formula II; X represents X or X' of Formual II; and n represents n or n' of Formula II, to form a compound having a perfluorocyclobutane group.
    Type: Grant
    Filed: June 9, 1989
    Date of Patent: June 4, 1991
    Assignee: The Dow Chemical Company
    Inventors: Katherine S. Clement, David A. Babb, Bobby R. Ezzell
  • Patent number: 5017711
    Abstract: New 4,4,5,8-tetramethyl-1-oxaspiro[2.5]octane. A process for its preparation starting from 2,2,3,6-tetramethyl-1-cyclohexanone is described.4,4,5,8-Tetramethyl-1-oxaspiro[2.5]octane is a useful raw material for the preparation of 2,2,3,6-tetramethyl-cyclohexane-carbaldehyde, a key intermediate for the synthetis of valuable fragrance ingredients.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: May 21, 1991
    Assignee: Firmenich S.A.
    Inventors: Christian Chapuis, Christian Margot, Karl-Heinrich Schulte-Elte, Herve Pamingle
  • Patent number: 4950797
    Abstract: A process for the preparation of carbonyl compounds by catalyzed isomerization of allyl alcohols in a tertiary phosphine or phosphite ester in the presence of a rhodium compound at a temperature of from 80.degree. C. to 180.degree. C., a carrier gas being passed through the reaction mixture and the carbonyl compound being separated from the emergent gas mixture by cooling.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Werner Bertleff, Michael Roeper
  • Patent number: 4922027
    Abstract: The cycloaliphatic aldehydes of formula ##STR1## wherein R.sup.0, R.sup.1 and R.sup.2 represent independently a hydrogen atom or a lower alkyl from C.sub.1 to C.sub.6 and X stands for a group of formula ##STR2## wherein R.sup.3 and R.sup.4 represent independenly a lower alkyl radical from C.sub.1 to C.sub.3 and R.sup.5 represents a lower alkyl radical or hydrogen, provided that R.sup.1, R.sup.3 and R.sup.4 do not represent simulataneously a methyl radical whenever R.sup.0 and R.sup.2 represent each a hydrogen atom, are prepared from enol esters of formula ##STR3## wherein the wavy line stands for a --C--O-- bond of cis or trans configuration, Y represents an acyl group or P(O)(OR).sub.2, wherein R stands for a lower alkyl monovalent radical or an aryl, and Z defines a group of formula ##STR4## wherein R.sup.3, R.sup.4 and R.sup.5 are defined as above, by cyclisation carried out by means of an acidic cyclisation agent.
    Type: Grant
    Filed: January 4, 1989
    Date of Patent: May 1, 1990
    Assignee: Firmenich SA
    Inventors: Dana P. Simmons, Christian Chapuis
  • Patent number: 4910347
    Abstract: Racemic and optically active cycloaliphatic 2,2,6-trimethylcyclohexanecarboxyaldehyde, also known as dihydrocyclocitral, are prepared by a novel process consisting in the cyclization of enol esters of formula ##STR1## wherein the wavy line defines a C--O bond of cis or trans configuration, X represents an acyl group or P(O)(OR).sub.2, wherein R stands for a lower alkyl monovalent radical or an aryl, and Z represents a monovalent radical of formula ##STR2## by means of an acid cyclization agent.
    Type: Grant
    Filed: October 30, 1988
    Date of Patent: March 20, 1990
    Assignee: Firmenich SA
    Inventor: Dana P. Simmons
  • Patent number: 4868339
    Abstract: Multimethyl cyclohexene or cyclohexane derivatives having woody, spicy, amber or violet odors are disclosed. The derivatives can be formulated into perfurmes, talcs, lotions, cremes and air fresheners.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: September 19, 1989
    Assignee: BASF K & F Corporation
    Inventors: Philip A. Christenson, Brian J. Drake
  • Patent number: 4820875
    Abstract: In a process for vapour-phase synthesis of carbonyl compounds from alcohols a mixture of the alcohol and air or oxygen is passed over a silver catalyst. The concentration of alcohol:air or alcohol:oxygen is below the explosive limits. The process is conducted as a temperature between 200.degree. and 450.degree. C. Previously the production of carbonyl compounds required a temperature of 450.degree.-700.degree. C. which necessitated the use of heat exchangers using fused salt baths. The silver catalyst may be supported.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: April 11, 1989
    Assignee: Johnson Matthey Public Limited Company
    Inventors: Dennis E. Webster, Phillip J. Player
  • Patent number: 4759880
    Abstract: A series of alkanoarachidonic acids have been prepared as modulators of the arachidonic acid cascade to increase the production of biologically desirable compounds and minimize the production of biologically undesirable compounds. Examples of desirable compounds in this respect comprise postaglandins and thromboxanes whereas undesirable compounds comprise the mono- and polyhydroxyarachidonic acids and leukotrienes. The alkanoarachidonic acids and their intermediates are of the general formula: ##STR1## and at least one of X, Y, and Z is lower alkano and is hydrogen when not lower alkano; the esters and salts of the acids are also prepared. The acids, esters and salts may be used as anti-anaphylaxis or anti-thrombosis agents.
    Type: Grant
    Filed: September 27, 1984
    Date of Patent: July 26, 1988
    Assignee: Research Corporation
    Inventors: Kyriacos C. Nicolaou, Nicos A. Petasis, Wen-Sen Li, Tamara Ladduwahetty, Jared L. Randall, Stephen E. Webber, Pedro E. Hernandez
  • Patent number: 4755329
    Abstract: The invention relates to ring A-diol units suitable for synthesizing 1.alpha.-hydroxyvitamin D compounds by subsequent condensation with appropriate .sup.C /.sub.D -ring fragments and to methods for preparing such ring A-diol units.
    Type: Grant
    Filed: June 10, 1985
    Date of Patent: July 5, 1988
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Seok H. Lee
  • Patent number: 4720593
    Abstract: There is disclosed a process for the production of 1-methylcyclopropanecarboxaldehyde of the formula ##STR1## comprising treating 4-chloro-2-methyl-butanal of the formula ##STR2## at a temperature between -40.degree. and +7.degree. C. in an inert solvent with a 1.0 to 10.0 fold molar amount of a strong, non-nucleophilic base.
    Type: Grant
    Filed: October 22, 1986
    Date of Patent: January 19, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Juan Andrade, Gunter Prescher, Klaus Kohler
  • Patent number: 4716241
    Abstract: Novel cyclopentane derivatives which are useful as an intermediate for the preparation of N-(L-aspartyl)-N'-(2,2,5,5-tetramethylcyclopentanecarbonyl)-R-1,1-diaminoe thane are represented by the formula (I) ##STR1## wherein R.sub.1 is hydrogen and R.sub.2 is cyano, formyl, carbamoyl, alkanesulfonyloxy, or ##STR2## wherein R.sub.3 and R.sub.4 are the same or different and represent alkyl, substituted alkyl or R.sub.1 and R.sub.2 are combined to be methylsulfinylmethylene, acetoxymethylthiomethylene, halomethylthiomethylene, methylthiomethylene, alkoxy-methylene, or --CH.sub.2 --O--.
    Type: Grant
    Filed: February 28, 1986
    Date of Patent: December 29, 1987
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Takayoshi Yamauchi, Kaneaki Hattori, Shunichi Ikeda, Kentaro Tamaki
  • Patent number: 4701540
    Abstract: A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: October 20, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
  • Patent number: 4691060
    Abstract: Waste heat possessed by a hot formaldehyde product gas obtained by catalytic reaction of methanol with air is heat exchanged with pressurized water in a waste heat boiler, thereby generating steam, and then leading the product gas to a formaldehyde absorption column, thereby absorbing formaldehyde, into an aqueous solution, and heat exchanging a recycling solution for a feed gas humidifier with the aqueous solution withdrawn from the bottom of absorption column. The waste heat can be efficiently recovered without deposition of paraformaldehyde on the heat transfer surface of heat exchanger and the amount of additional steam can be reduced or made entirely zero.
    Type: Grant
    Filed: November 25, 1986
    Date of Patent: September 1, 1987
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shigeo Kimura, Kouichi Kurata
  • Patent number: 4691048
    Abstract: The invention concerns a process for reducing carbonylation of an aldehyde wherein the aldehyde is used as hemiacetalester, the reaction being conducted in the presence of a catalyst consisting of a cobalt carbonyl complex.The hemiacetal-ester may be formed in situ by reacting an acetal with an anhydride of acid.The process preferentially yields alkylene-glycol mono-esters, free of esterified, for a ratio H.sub.2 /CO ranging from 1:1 to 3:1 and preferentially 2-alkoxy aldehydes, for a ratio H.sub.2 /CO ranging from 0.1:1 to 0.5:1.
    Type: Grant
    Filed: May 10, 1985
    Date of Patent: September 1, 1987
    Assignee: Institut Francais du Petrole
    Inventors: Francois Hugues, Dominique Commereuc, Yves Chauvin