From Aldehyde Or Ketone Patents (Class 568/878)
  • Publication number: 20020013501
    Abstract: A process for the preparation of hydroxy and amino compounds, in which, in a first step, an aldehyde, ketone or imine is reacted in a Reformatsky reaction with a reactive halogen compound and zinc, in carboxylic esters as solvents, the reactive halogen compound being brought into contact with the zinc at the same time as or after contact with the aldehyde, ketone or imine, and in a second step, the reaction product of the first step is hydrolyzed.
    Type: Application
    Filed: June 26, 2001
    Publication date: January 31, 2002
    Applicant: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Klas Sorger, Hermann Petersen
  • Publication number: 20010034464
    Abstract: A reductive system including a silane, preferably PMHS, and an active zinc compound, which is monomeric and not a hydride, wherein a reduction of a carbonyl substrate to a corresponding alcohol is achievable.
    Type: Application
    Filed: April 6, 2001
    Publication date: October 25, 2001
    Applicant: FIRMENICH SA
    Inventor: Hubert Mimoun
  • Patent number: 6232506
    Abstract: Provided are a process for producing 6-methyl-3-hepten-2-one by cross aldol condensation carried out while each continuously adding to acetone, isovaleraldehyde and an aqueous alkali containing an alkaline substance; a process for producing a 6-methyl-2-heptanone analogue represented by Formula (1): wherein n is an integer of 0 or 1 or more; which comprises allowing hydrogen, acetone and an aldehyde represented by Formula (2): wherein n is as defined above; X and Y each represents a hydrogen atom or they are coupled together to form a carbon-carbon bond; and Z and W each represents a hydrogen atom or they are coupled together to form a carbon-carbon bond; to react in the presence of an aqueous alkali containing an alkaline substance, and a hydrogenation catalyst; and a process for producing phytone or isophytol using the 6-methyl-3-hepten-2-one or the 6-methyl-2-heptanone analogue.
    Type: Grant
    Filed: June 24, 1999
    Date of Patent: May 15, 2001
    Assignee: Kuraray Co., Lyd.
    Inventors: Yoichi Kido, Noriaki Kumagai, Hideharu Iwasaki, Takashi Onishi, Fuyuo Ueyama
  • Patent number: 6049011
    Abstract: A dilute ethylene stream, e.g., one produced by steam cracking, is oxonated to yield propanal, without the need to separate other lower hydrocarbons.
    Type: Grant
    Filed: October 15, 1997
    Date of Patent: April 11, 2000
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Gabor Kiss, Michael G Matturro, Harry William Deckman, Frank Hershkowitz, David R. Lumgair, Jr., Gary F Janda, Daniel N King
  • Patent number: 6005133
    Abstract: The enantioselective borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by performing the reduction in the presence of catalytic amounts of the new and valuable oxazaborolidine compounds of formulae (I) and (II). The compounds of formulae (I) and (II) may be isolated and purified prior to use in the reduction reactions or the compounds of formulae (I) and (II) may be generated in situ.
    Type: Grant
    Filed: October 10, 1995
    Date of Patent: December 21, 1999
    Assignee: Pfizer Inc.
    Inventor: George Joseph Quallich
  • Patent number: 5817850
    Abstract: The synthesis of new sterically hindered ferrocene bis(phosphonites) of formula I ##STR1## the synthesis of the corresponding transition-metal complexes and the use of these complexes in transition-metal-catalyzed reactions are described.
    Type: Grant
    Filed: October 30, 1997
    Date of Patent: October 6, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Stephen D. Pastor, Sai P. Shum
  • Patent number: 5523495
    Abstract: The present invention provides a process for producing a propargylcarbinol compound of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are as defined herein. The process comprises reacting a haloallylcarbinol compound of formula (II) with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargylcarbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: June 4, 1996
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
  • Patent number: 5495055
    Abstract: A deactivated supported ruthenium catalyst which has been used to continuously hydrogenate an aqueous acetone stream is regenerated by contacting with steam at an elevated temperature. Periodic regeneration in this manner serves to maintain a high rate of reaction in a process which converts acetone to isopropanol.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: February 27, 1996
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Michael A. Rueter
  • Patent number: 5395993
    Abstract: A process for preparing alkenols of the formula IR.sup.1 --CH.dbd.CH(CH.sub.2).sub.n OH Iwhere R.sup.1 is hydrogen or a hydrocarbon radical, and n is an integer from 3 to 15,a) by reacting a phosphonium salt of the formula IIaR.sup.1 --CH.sub.2 --P.sup.+ (C.sub.6 H.sub.5).sub.3 X.sup.-IIawhere X is chlorine, bromine or iodine, with an aldehyde of the formula IIIa or its hemiacetal of the formula IIIb ##STR1## or b) by reacting a phosphonium salt of the formula IIb(C.sub.6 H.sub.5).sub.3 P.sup.+ (CH.sub.2).sub.n+1 OH X.sup.-IIbwith a aldehyde of the formula IVR.sup.1 CHO IVin a solvent in the presence of a base, wherein the base is the alkali metal salt of an alcohol and the solvent is an alcohol.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: March 7, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Klein, Ernst Buschmann, Christiane Mackenroth
  • Patent number: 5334779
    Abstract: Disclosed are catalyst compositions comprised of the oxides of copper, zinc, and a third element selected from the group consisting of aluminum, magnesium, zirconium, and mixtures thereof, and the use of such catalyst compositions in the hydrogenation of carbonyl compounds such as carboxylate esters to obtain the alcohol corresponding to the acid residue of the ester.
    Type: Grant
    Filed: June 1, 1993
    Date of Patent: August 2, 1994
    Assignee: Eastman Kodak Company
    Inventor: Yeong-Jen Kuo
  • Patent number: 5292973
    Abstract: An improvement is proposed for the removal of the precipitates of a phosphine oxide compound as a by-product from a mixture thereof with an olefin compound obtained by the Wittig reaction for the preparation of the olefin compound from a phosphorane compound and a carbonyl compound. Instead of the conventional procedure of filtration to remove the precipitates, the mixture in a hydrocarbon solvent, after replacement of a non-hydrocarbon solvent with a hydrocarbon solvent, if necessary, is admixed with a lower carboxylic acid such as acetic acid so that the precipitates of the phosphine oxide are dissolved forming a viscous fluid which is immiscible with the mixture of the olefin compound and the hydrocarbon solvent. The fluid containing the dissolved phosphine oxide compound can be easily removed by phase separation so that a great increase is obtained in the yield of the desired olefin compound.
    Type: Grant
    Filed: June 24, 1993
    Date of Patent: March 8, 1994
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takehiko Fukumoto, Akira Yamamoto
  • Patent number: 5220020
    Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: June 15, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
  • Patent number: 5198592
    Abstract: The invention concerns a method of performing a chemical reaction in which hydrogenation and/or dehydrogenation occurs, in the presence of a supported catalyst comprising a carrier material with copper as active component and iron as a promotor. According to the invention, the proporation of iron, calculated on the amount of copper and iron jointly, on an atomic basis, is no more than 25%. The invention also relates to a catalyst for carrying out the reaction, and to a process for preparing a supported catalyst.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: March 30, 1993
    Assignee: Engelhard De Meern B.V.
    Inventors: Johannes van Beijnum, Adrianus J. van Dillen, John W. Geus
  • Patent number: 5175378
    Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: December 29, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5175371
    Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: December 29, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5149889
    Abstract: A process is disclosed for the preparation of tertiary alcohols, alpha-alkyl substituted nitriles, alkyl-substituted imines or tertiary amines by alkylation of a starting material that is a carbonyl compound or a nitrile followed by hydrolysis wherein the alkylation is carried out with the aid of a reaction system formed by suspending a mixture of:substantially 15 to 25% by weight of methyllithium or ethyllithium;substantially 35 to 45% by weight of an inorganic compound selected from the group which consists of at least one metal oxide selected from the group which consists of SiO.sub.2, Al.sub.2 O.sub.3, and CaO, and synthetic anhydrous aluminum silicate; andsubstantially 35 to 45% by weight of a paraffin oil or wax; in an organic solvent selected from the group which consists of:C.sub.5 to C.sub.10 saturated aliphatic hydrocarbons, C.sub.5 to C.sub.
    Type: Grant
    Filed: October 30, 1990
    Date of Patent: September 22, 1992
    Assignee: Metallgesellschaft Aktiengesellschaft
    Inventors: Jurgen Deberitz, Wilfried Weiss
  • Patent number: 5091598
    Abstract: Process of preparation of alcohols by the reaction of an organic halide with a carbonyl compound in an organic solvent, in the presence of metallic manganese, followed by hydrolysis of the reaction product; the reaction is initiated and activated by an ester present in the reaction medium.
    Type: Grant
    Filed: December 28, 1988
    Date of Patent: February 25, 1992
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Gerard Cahiez, Pierre-Yves Chavant, Pierre Tozzolino
  • Patent number: 5091597
    Abstract: Process of preparation of secondary or tertiary alcohols by the action of an organic halide on metallic manganese, in the presence of a carbonyl compound in a solvent followed by hydrolysis; a compound of a metal of Groups II to VIII of the Periodic Classification of the Elements, less electropositive than manganese, is present in the reaction medium.
    Type: Grant
    Filed: August 28, 1990
    Date of Patent: February 25, 1992
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Gerard Cahiez, Pierre-Yves Chavant, Pierre Tozzolino
  • Patent number: 5089659
    Abstract: E7/Z9 -alkadien-1-ols which may be protected at the hydroxy group are prepared by subjecting a 7-hydroxyheptenal to a Wittig reaction with a phosphorylide to give an acetal compound which is converted by further Wittig reaction with a phosphorylide to an E7/Z9 -alkadienol.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: February 18, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Christiane Brueckner, Ernst Buschmann, Wolfgang Mackenroth, Walter Himmele, Heinz Eckhardt
  • Patent number: 5072060
    Abstract: A method for the preparation of branched primary alcohols comprises reacting a normal alkane with formaldehyde in non-aqueous media in the presence of a free radical initiator. The reaction involves the preferential addition of formaldeyhde to internal carbon atoms of the normal alkane, resulting in a branched primary alcohol containing one carbon more than the alkane reactant. The product alcohols are obtained as mixtures of positional isomers.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: December 10, 1991
    Assignee: Texaco Chemical Company
    Inventors: John R. Sanderson, Edward T. Marquis
  • Patent number: 5068469
    Abstract: Condensed dimer alcohols, also known as Guerbet alcohols, are prepared using metal alkoxide as the catalyst by reacting alcohol with saturated or unsaturated aldehyde or allyl alcohol, or mixtures thereof, at 100.degree.-220.degree. C. and removing water as it is formed during the reaction. Dimer alcohols are prepared in high yields without the need for a transition metal catalyst.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: November 26, 1991
    Assignee: Exxon Chemical Patents Inc.
    Inventors: David A. Young, John A. Jung, Mark L. McLaughlin
  • Patent number: 5004844
    Abstract: A process for the preparation of a primary or secondary alcohol, which comprises hydrogenating respectively an aldehyde or ketone in the presence of a catalyst system comprising a platinum compound, an acid having a pKa in the range from about 2 to about 10.5 and a phosphorus compound of the formula R.sup.1 R.sup.2 POH, wherein R.sup.1 and R.sup.2 each independently represents an alkyl group or a phenyl group, at a temperature in the range from about 20.degree. to about 150.degree. C. and at a pressure in the range from about 1 to about 100 bar.
    Type: Grant
    Filed: June 28, 1989
    Date of Patent: April 2, 1991
    Assignee: Shell Oil Company
    Inventors: Petrus W. N. M. Van Leeuwen, Cornelis F. Roobeek
  • Patent number: 4978794
    Abstract: 2-Alkenylbis(2-isocaranyl)boranes represented by the formula: ##STR1## wherein R is 2-alkenyl. The compounds undergo asymmetric 2-alkenylboration with a variety of aldehydes and afford the corresponding alcohols in 94-99% ee.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: December 18, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4958033
    Abstract: A process for preparing an alcohol of the formula: ##STR1## by reacting a carbonyl compound of the formula: ##STR2## or an oxirane of the formula: ##STR3## magnesium and a propargyl halide of the formula: ##STR4## followed by hydrolysis, characterized in that the carbonyl compound (II) or the oxirane compound (III) and the propargyl halide (IV) are reacted simultaneously with magnesium in an inert solvent in the presence of zinc or a halide thereof.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: September 18, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukihisa Takisawa, Nobuharu Kono, Kenji Saito, Hiroshi Yamachika
  • Patent number: 4734516
    Abstract: The reaction of a zinc compound compound of formula IIICF.sub.3 CCl.sub.2 ZnCl.yL (III)wherein y is 1 or 2 and L is a solvent ligand selected from the group consisting of the N-disubstituted acid amides, N-substituted lactams and organic sulfoxides, with an aldehyde of formula IIR--CHO (II)wherein R is an aliphatic or aromatic hydrocarbon radical or an aliphatic or aromatic heterocyclic radical, gives 1-propanols of formula I ##STR1## in high yields.
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: March 29, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert W. Lang
  • Patent number: 4694108
    Abstract: A process of producing higher ketones comprises the step of contacting under suitable conditions a feed comprising (a) at least one C.sub.3 -C.sub.6 aliphatic ketone, (b) at least one C.sub.2 -C.sub.6 aliphatic aldehyde and, preferably, also (c) carbon monoxide with a catalyst composition comprising (i) copper or an oxide thereof and (ii) zinc oxide. Preferably, the feed ketone is methyl ethyl ketone, the feed aldehyde is propanal, and the product comprises at least one C.sub.7 ketone.
    Type: Grant
    Filed: August 1, 1986
    Date of Patent: September 15, 1987
    Assignee: Phillips Petroleum Company
    Inventor: David J. Elliott
  • Patent number: 4518813
    Abstract: (2R,6R)-1-Chloro-2,6,10-trimethyl-undecane I, (R)-(+)-.beta.-chloro-isobutyric acid II, (S)-(+)-1-bromo-3-chloro-2-methylpropane IV and (2R)-(+)-1-chloro-2,6-dimethyl-heptane V are novel optically active units for the synthesis of the side chain of (R,R,R)-.alpha.-tocopherol. In the process according to the invention, the optically active C.sub.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: May 21, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Friedrich Vogel, Joachim Paust
  • Patent number: 4493801
    Abstract: Tertiary alcohols are prepared by oxidizing tertiary aldehydes with oxygen at elevated temperatures.The tertiary alcohols prepared in this way are valuable and versatile intermediates for dyes, drugs and crop protection agents and are used, for example, in the preparation of agrochemicals.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: January 15, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Gerhard Nestler
  • Patent number: 4443637
    Abstract: Disclosed is a process for converting a carbohydrate or lactic acid feedstock into an ethanol product in the presence of a metal salt at a reaction temperature ranging from about 250.degree. to about 400.degree. C. The improvement comprises establishing a reaction mixture of said feedstock, said metal salt, water, and an organic solvent. The organic solvent has a boiling point above about 150.degree. C., is stable at the reaction temperature, and solvates said feedstock. The solvent is selected from the group consisting of an alcohol, an ether, a tertiary amine, an amine oxide, a quaternary ammonium hydroxide, and a sulfoxide.
    Type: Grant
    Filed: June 17, 1982
    Date of Patent: April 17, 1984
    Assignee: Battelle Development Corporation
    Inventor: Melville E. D. Hillman
  • Patent number: 4435605
    Abstract: The invention is a process for the preparation of a 2-phenylethyl alcohol which comprises contacting an aromatic aldehyde with carbon monoxide and hydrogen in a solvent comprising an oxygenated polar hydrocarbon and water, in the presence of a catalytic amount of a catalyst comprising a cobalt compound, a ruthenium salt and an iodine salt, at elevated temperatures and a pressure of between 600 and 45,000 psi.
    Type: Grant
    Filed: August 27, 1982
    Date of Patent: March 6, 1984
    Assignee: The Dow Chemical Company
    Inventors: Susan B. Butts, George E. Hartwell
  • Patent number: 4426542
    Abstract: A preparation of a plasticizer alcohol, consisting of predominantly 2-propylheptanol, from linear butenes is described in which oxo product of the butenes is aldoled to condense n-pentaldehyde therein with very little cross-aldolization followed by hydrogenation to obtain the 2-propylheptanol with very small 2-propyl-4-methyl hexanol content. The alcohol product as phthalate ester has excellent plasticizer properties. Also processes are described for converting other olefins to alcohols by oxo, aldol and hydrogenation reactions, with particular attention to converting hexenes obtained by propylene dimerization to C.sub.14 alcohols suitable for preparation of detergents.
    Type: Grant
    Filed: June 11, 1981
    Date of Patent: January 17, 1984
    Assignee: Monsanto Company
    Inventors: George E. Barker, Denis Forster
  • Patent number: 4426321
    Abstract: This invention discloses a number of novel odorant alkadienyl ketones, alcohols and oximes having from 9 to 15 carbon atoms, processes for making same and odorant compositions containing same.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: January 17, 1984
    Assignee: Givaudan Corporation
    Inventor: Paul A. Ochsner
  • Patent number: 4414421
    Abstract: A process for the preparation of glycol aldehyde, which comprises reacting formaldehyde with hydrogen and carbon monoxide, in the presence of a rhodium- and/or a cobalt-containing catalyst, sulphur dioxide, and water.
    Type: Grant
    Filed: May 26, 1982
    Date of Patent: November 8, 1983
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4375005
    Abstract: Described are compounds defined according to the structure: ##STR1## taken alone or in admixture wherein one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines are carbon-carbon single bonds; wherein R.sub.1 represents C.sub.1 -C.sub.4 alkyl; R.sub.2 represents C.sub.1 -C.sub.4 alkyl; Z represents oxygen or sulfur; R.sub.3 represents hydrogen, MgX, Li, C.sub.1 -C.sub.3 lower alkyl or C.sub.1 -C.sub.3 lower acyl; and wherein X represents chloro, bromo or iodo and uses thereof in augmenting or enhancing the aroma and/or taste of consumable materials such as perfume compositions, colognes, perfumed articles, e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions or dryer-added fabric softener articles, smoking tobaccos, chewing gums, chewing tobaccos, medicinal products or toothpastes.
    Type: Grant
    Filed: November 19, 1981
    Date of Patent: February 22, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Richard M. Boden
  • Patent number: 4347388
    Abstract: 3,6-Dimethyl-3-hydroxy-oct-1-ynes and -oct-1-enes and their esters with lower alkanoic acids, of the general formula I ##STR1## where X and Y are H or the two X's and/or the two Y's together are a further bond between the carbon atoms on which they are present, and R is H, --CO--CH.sub.3, --CO--C.sub.2 H.sub.5 or --CO--C.sub.3 H.sub.7, their use as scents, and a process for the preparation of 3,6-dimethyl-3-hydroxy-octane. The novel compounds exhibit interesting, predominantly floral, woody, herbal and fruity notes. The alcohols of the formula I are of particular importance because they serve as intermediates for a novel and particularly advantageous method of obtaining 3,6-dimethyl-3-hydroxy-octane, a compound required in large amounts as a fragrance for soaps and detergents.
    Type: Grant
    Filed: July 2, 1981
    Date of Patent: August 31, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Gramlich, Werner Hoffmann, Leopold Hupfer, Bernd Meissner, Juergen Paetsch
  • Patent number: 4341910
    Abstract: A process for the production of cis and trans isomers of compounds having the formula ##STR1## in which R, R' and R" are independently hydrogen or alkyl groups having from 1 to 20 carbon atoms, comprising(a) reacting the corresponding cis or trans isomer of a compound having the formula ##STR2## in which Q is an alkyl group having from 1 to 20 carbon atoms, with paraformaldehyde and(b) hydrolyzing the resulting product to produce the unsaturated alcohol.
    Type: Grant
    Filed: January 25, 1979
    Date of Patent: July 27, 1982
    Assignee: Texas Alkyls, Inc.
    Inventors: Dennis B. Malpass, G. Scott Yeargin
  • Patent number: 4301084
    Abstract: In a process for the preparation of a carboxylic acid ester of .beta.-formyl-crotyl alcohol by rearrangement of the corresponding carboxylic acid ester of 2-formyl-2-hydroxy-but-3-ene or of an acetal or acylate thereof in the presence of copper or a copper compound, followed, where relevant, by hydrolytic cleavage of the acetal or acylate, more especially in the preparation of 4,4-dimethoxy-3-methyl-crotyl acetate, the yield is improved by carrying out the rearrangement in the presence of copper (I) chloride as the catalyst and ensuring that low-boiling by-products formed during the rearrangement are removed.The products are of great importance as starting materials for an industrial synthesis of vitamin A and its derivatives.
    Type: Grant
    Filed: August 31, 1979
    Date of Patent: November 17, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Harald Laas, Axel Nissen, Bernd Meissner
  • Patent number: 4277633
    Abstract: The palladium complex disclosed herein is bis[tri(ortho-tolyl)phosphine] :palladium which is produced by reacting a palladium salt with tri(ortho-tolyl)phosphine and reducing the resultant bis[tri(ortho-tolyl)phosphine] palladium salt with an alcoholic alkali. This complex is useful as a catalyst for the production of 1,3-diene oligomers.
    Type: Grant
    Filed: July 12, 1979
    Date of Patent: July 7, 1981
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
  • Patent number: 4220795
    Abstract: Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: September 2, 1980
    Assignee: Miles Laboratories, Inc.
    Inventors: Harold C. Kluender, Henry C. Arndt
  • Patent number: 4198532
    Abstract: Alcohols having the formula: ##STR1## wherein R is 1-hydroxy-2-methyl-propyl or 3-hydroxy-butyl, perfume compositions containing same and processes and intermediates involving same are disclosed.
    Type: Grant
    Filed: July 25, 1978
    Date of Patent: April 15, 1980
    Assignee: Givaudan Corporation
    Inventor: Paul A. Ochsner
  • Patent number: 4179579
    Abstract: Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: December 18, 1979
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara
  • Patent number: 4165330
    Abstract: An asymmetric synthesis process which involves addition of optically active chelated organometal compounds of lithium, sodium, beryllium, magnesium, zinc, copper and cadmium to prochiral unsaturated substrates. The optically active chelating agent is not consumed and can be recycled.
    Type: Grant
    Filed: February 13, 1978
    Date of Patent: August 21, 1979
    Assignee: Exxon Research & Engineering Co.
    Inventors: Thomas A. Whitney, Arthur W. Langer, Jr.
  • Patent number: 4125484
    Abstract: Novel tertiary alcohols of the general formula: ##STR1## in which R.sub.1 represents an alkenyl or a cycloalkyl or cycloalkenyl optionally substituted by one or more alkyl groups, R.sub.2 represents hydrogen or alkyl; or R.sub.1 and R.sub.2, together with the carbon atom to which they are linked, from a bicyclo group optionally substituted by up to two alkyl groups; R.sub.3 and R.sub.4 each represents an alkyl group, and Y represents a divalent aliphatic group of up to 4 carbon atoms, are disclosed along with their use as aroma chemicals and a process for their preparation.
    Type: Grant
    Filed: February 24, 1977
    Date of Patent: November 14, 1978
    Assignee: Shell Oil Company
    Inventors: Robin T. Gray, Aaldert J. De Jong
  • Patent number: 4118406
    Abstract: A process for preparing cis-olefins of the formula ##STR1## where R ia alkyl or alkenyl and R.sup.1 is alkyl and alkenyl, both optionally substituted by hydroxy, carbalkoxy or acyloxy, which comprises an ylide solution of the compound R--CH.sub.2 --P.sup..sym. (C.sub.6 H.sub.5).sub.3 Br.sup..crclbar. in hexaalkyl phosphoric acid traimide and adding an aldehyde of the formula R.sup.1 --CHO.
    Type: Grant
    Filed: August 8, 1977
    Date of Patent: October 3, 1978
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Jurgen Bestmann, Werner Theo Stransky, Otto Vostrowsky
  • Patent number: 4098727
    Abstract: This specification discloses a process for the production of oxygenated compounds, more specifically aldehydes and alcohols, by reacting an olefin with hydrogen and carbon monoxide in the presence of, as a catalyst, an insoluble polymer containing a functional group, which may be an amine, thiol, phosphine, or arsine group, having chemically bonded thereto a metal of Group VIII of the Periodic Table. The metal can be, for example, rhodium, cobalt, or ruthenium. The olefin can contain more than one carbon-to-carbon double bond, may be an open chain or a cyclic olefin, and may be substituted. Further, the olefin may be contained in a refinery stream such as a cracked gasoline. The reaction may be carried out in the presence of a polar solvent.
    Type: Grant
    Filed: January 19, 1971
    Date of Patent: July 4, 1978
    Assignee: Mobil Oil Corporation
    Inventors: Werner O. Haag, Darrell Duayne Whitehurst
  • Patent number: 4087468
    Abstract: Grignard reagents of halo-substituted conjugated dienes are prepared by reaction of 1- or 2-halo-substituted conjugated diene with magnesium metal employing a metal halide/saturated aliphatic halide catalyst system. The Grignard reagent can be employed in the preparation of hydroxy-substituted conjugated dienes and hydroxy-substituted allenes. Adjustment of the molar ratio of the metal halide to the halo-substituted conjugated diene permits favoring of hydroxy-substituted conjugated dienes or hydroxy-substituted allenes in the diene products.
    Type: Grant
    Filed: December 12, 1975
    Date of Patent: May 2, 1978
    Assignee: Phillips Petroleum Company
    Inventor: Paul W. Solomon