From Aldehyde Or Ketone Patents (Class 568/878)
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Publication number: 20020013501Abstract: 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: ApplicationFiled: June 26, 2001Publication date: January 31, 2002Applicant: Consortium fur Elektrochemische Industrie GmbHInventors: Klas Sorger, Hermann Petersen
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Publication number: 20010034464Abstract: 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: ApplicationFiled: April 6, 2001Publication date: October 25, 2001Applicant: FIRMENICH SAInventor: Hubert Mimoun
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Patent number: 6232506Abstract: 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: GrantFiled: June 24, 1999Date of Patent: May 15, 2001Assignee: Kuraray Co., Lyd.Inventors: Yoichi Kido, Noriaki Kumagai, Hideharu Iwasaki, Takashi Onishi, Fuyuo Ueyama
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Patent number: 6049011Abstract: 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: GrantFiled: October 15, 1997Date of Patent: April 11, 2000Assignee: 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
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Patent number: 6005133Abstract: 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: GrantFiled: October 10, 1995Date of Patent: December 21, 1999Assignee: Pfizer Inc.Inventor: George Joseph Quallich
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Patent number: 5817850Abstract: 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: GrantFiled: October 30, 1997Date of Patent: October 6, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Stephen D. Pastor, Sai P. Shum
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Patent number: 5523495Abstract: 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: GrantFiled: February 13, 1995Date of Patent: June 4, 1996Assignee: Sumitomo Chemical Company LimitedInventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
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Patent number: 5495055Abstract: 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: GrantFiled: February 13, 1995Date of Patent: February 27, 1996Assignee: Arco Chemical Technology, L.P.Inventor: Michael A. Rueter
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Patent number: 5395993Abstract: 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: GrantFiled: February 4, 1994Date of Patent: March 7, 1995Assignee: BASF AktiengesellschaftInventors: Ulrich Klein, Ernst Buschmann, Christiane Mackenroth
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Patent number: 5334779Abstract: 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: GrantFiled: June 1, 1993Date of Patent: August 2, 1994Assignee: Eastman Kodak CompanyInventor: Yeong-Jen Kuo
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Patent number: 5292973Abstract: 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: GrantFiled: June 24, 1993Date of Patent: March 8, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takehiko Fukumoto, Akira Yamamoto
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Patent number: 5220020Abstract: 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: GrantFiled: November 14, 1991Date of Patent: June 15, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
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Patent number: 5198592Abstract: 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: GrantFiled: October 15, 1990Date of Patent: March 30, 1993Assignee: Engelhard De Meern B.V.Inventors: Johannes van Beijnum, Adrianus J. van Dillen, John W. Geus
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Patent number: 5175378Abstract: 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: GrantFiled: March 16, 1992Date of Patent: December 29, 1992Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5175371Abstract: 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: GrantFiled: March 16, 1992Date of Patent: December 29, 1992Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5149889Abstract: 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: GrantFiled: October 30, 1990Date of Patent: September 22, 1992Assignee: Metallgesellschaft AktiengesellschaftInventors: Jurgen Deberitz, Wilfried Weiss
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Patent number: 5091598Abstract: 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: GrantFiled: December 28, 1988Date of Patent: February 25, 1992Assignee: Societe Nationale Elf AquitaineInventors: Gerard Cahiez, Pierre-Yves Chavant, Pierre Tozzolino
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Patent number: 5091597Abstract: 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: GrantFiled: August 28, 1990Date of Patent: February 25, 1992Assignee: Societe Nationale Elf AquitaineInventors: Gerard Cahiez, Pierre-Yves Chavant, Pierre Tozzolino
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Patent number: 5089659Abstract: 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: GrantFiled: May 19, 1989Date of Patent: February 18, 1992Assignee: BASF AktiengesellschaftInventors: Christiane Brueckner, Ernst Buschmann, Wolfgang Mackenroth, Walter Himmele, Heinz Eckhardt
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Patent number: 5072060Abstract: 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: GrantFiled: October 1, 1990Date of Patent: December 10, 1991Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
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Patent number: 5068469Abstract: 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: GrantFiled: February 7, 1990Date of Patent: November 26, 1991Assignee: Exxon Chemical Patents Inc.Inventors: David A. Young, John A. Jung, Mark L. McLaughlin
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Patent number: 5004844Abstract: 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: GrantFiled: June 28, 1989Date of Patent: April 2, 1991Assignee: Shell Oil CompanyInventors: Petrus W. N. M. Van Leeuwen, Cornelis F. Roobeek
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Patent number: 4978794Abstract: 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: GrantFiled: March 26, 1990Date of Patent: December 18, 1990Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 4958033Abstract: 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: GrantFiled: September 26, 1986Date of Patent: September 18, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Yukihisa Takisawa, Nobuharu Kono, Kenji Saito, Hiroshi Yamachika
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Patent number: 4734516Abstract: 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: GrantFiled: March 19, 1986Date of Patent: March 29, 1988Assignee: Ciba-Geigy CorporationInventor: Robert W. Lang
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Patent number: 4694108Abstract: 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: GrantFiled: August 1, 1986Date of Patent: September 15, 1987Assignee: Phillips Petroleum CompanyInventor: David J. Elliott
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Patent number: 4518813Abstract: (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: GrantFiled: September 30, 1982Date of Patent: May 21, 1985Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Friedrich Vogel, Joachim Paust
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Patent number: 4493801Abstract: 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: GrantFiled: November 2, 1981Date of Patent: January 15, 1985Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
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Patent number: 4443637Abstract: 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: GrantFiled: June 17, 1982Date of Patent: April 17, 1984Assignee: Battelle Development CorporationInventor: Melville E. D. Hillman
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Patent number: 4435605Abstract: 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: GrantFiled: August 27, 1982Date of Patent: March 6, 1984Assignee: The Dow Chemical CompanyInventors: Susan B. Butts, George E. Hartwell
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Patent number: 4426542Abstract: 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: GrantFiled: June 11, 1981Date of Patent: January 17, 1984Assignee: Monsanto CompanyInventors: George E. Barker, Denis Forster
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Patent number: 4426321Abstract: 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: GrantFiled: July 24, 1981Date of Patent: January 17, 1984Assignee: Givaudan CorporationInventor: Paul A. Ochsner
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Patent number: 4414421Abstract: 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: GrantFiled: May 26, 1982Date of Patent: November 8, 1983Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4375005Abstract: 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: GrantFiled: November 19, 1981Date of Patent: February 22, 1983Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4347388Abstract: 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: GrantFiled: July 2, 1981Date of Patent: August 31, 1982Assignee: BASF AktiengesellschaftInventors: Walter Gramlich, Werner Hoffmann, Leopold Hupfer, Bernd Meissner, Juergen Paetsch
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Patent number: 4341910Abstract: 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: GrantFiled: January 25, 1979Date of Patent: July 27, 1982Assignee: Texas Alkyls, Inc.Inventors: Dennis B. Malpass, G. Scott Yeargin
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Patent number: 4301084Abstract: 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: GrantFiled: August 31, 1979Date of Patent: November 17, 1981Assignee: BASF AktiengesellschaftInventors: Harald Laas, Axel Nissen, Bernd Meissner
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Patent number: 4277633Abstract: 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: GrantFiled: July 12, 1979Date of Patent: July 7, 1981Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Satoru Enomoto, Hisayuki Wada, Sadao Nishita, Yutaka Mukaida, Mikiro Yanaka, Hitoshi Takita
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Patent number: 4220795Abstract: 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: GrantFiled: August 14, 1978Date of Patent: September 2, 1980Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Henry C. Arndt
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Patent number: 4198532Abstract: 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: GrantFiled: July 25, 1978Date of Patent: April 15, 1980Assignee: Givaudan CorporationInventor: Paul A. Ochsner
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Patent number: 4179579Abstract: 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: GrantFiled: July 25, 1977Date of Patent: December 18, 1979Assignee: Kuraray Co., Ltd.Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara
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Patent number: 4165330Abstract: 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: GrantFiled: February 13, 1978Date of Patent: August 21, 1979Assignee: Exxon Research & Engineering Co.Inventors: Thomas A. Whitney, Arthur W. Langer, Jr.
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Patent number: 4125484Abstract: 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: GrantFiled: February 24, 1977Date of Patent: November 14, 1978Assignee: Shell Oil CompanyInventors: Robin T. Gray, Aaldert J. De Jong
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Patent number: 4118406Abstract: 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: GrantFiled: August 8, 1977Date of Patent: October 3, 1978Assignee: Hoechst AktiengesellschaftInventors: Hans Jurgen Bestmann, Werner Theo Stransky, Otto Vostrowsky
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Patent number: 4098727Abstract: 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: GrantFiled: January 19, 1971Date of Patent: July 4, 1978Assignee: Mobil Oil CorporationInventors: Werner O. Haag, Darrell Duayne Whitehurst
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Patent number: 4087468Abstract: 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: GrantFiled: December 12, 1975Date of Patent: May 2, 1978Assignee: Phillips Petroleum CompanyInventor: Paul W. Solomon