Six-membered Alicyclic Ring Containing Patents (Class 568/822)
  • Patent number: 5874651
    Abstract: A process for increasing the amount of isolatable products in a by-product stream generated in the production of 1,6 hexanediol includes combining the by-product stream with water to form a combination of the water and the by-product stream; and reacting the combination at a temperature between about 250.degree. C. to about 400.degree. C. at a pressure from about 1,000 psig to about 3,000 psig to form one or more reaction products.
    Type: Grant
    Filed: December 23, 1996
    Date of Patent: February 23, 1999
    Assignee: BASF Corporation
    Inventors: Andrew J. McNabb, Rebecca E. Phillips
  • Patent number: 5834606
    Abstract: There are described novel coupling reactions useful for the preparation of cyclitol and/or carbohydrate conjugates and carbocyclic analogs thereof. Such coupling reactions employ epoxides and/or aziridines described herein as electrophilic recipients of other cyclitol or carbohydrate units. Also provided are certain novel compounds.
    Type: Grant
    Filed: February 11, 1997
    Date of Patent: November 10, 1998
    Assignee: Genencor International, Inc.
    Inventor: Tomas Hudlicky
  • Patent number: 5831134
    Abstract: A process is disclosed for producing tertiary alcohols by radical addition of secondary alcohols to alkenes. The reaction is carried out as a continuous process in the presence of an organic peroxide as a radical initiator and during a mean contact time of the reaction mixture of up to a maximum of 1 hour.
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: November 3, 1998
    Assignee: Peroxid-Chemie GmbH
    Inventors: Michael Gnann, Maria Eckert, Robert Rieth, deceased, Werner Eberhard Wilhelm Rieth, heir, Emma Marianne Christine Rieth, heir
  • Patent number: 5792876
    Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: August 11, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
  • Patent number: 5731283
    Abstract: Described are 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different hydrogen or methyl; wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond; wherein the wavy line represents a carbon carbon single bond or a carbon carbon double bond; with the proviso that when the wavy line is a carbon carbon single bond then the dashed line is a carbon carbon single bond; wherein Y represents a moiety selected from the group consisting of: ##STR2## wherein H represents hydrogen, C.sub.1 -C.sub.4 lower alkyl or C.sub.1 -C.sub.2 acyl; and wherein R.sub.1 represents C.sub.1 -C.sub.4 lower alkyl with the additional proviso that when Y is the moiety: ##STR3## then the dashed line is a carbon carbon single bond, and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, perfumed articles and colognes.
    Type: Grant
    Filed: January 28, 1997
    Date of Patent: March 24, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, James Joseph Koestler, Jan Van Elst
  • Patent number: 5728796
    Abstract: A process reaction between: (1) a compound that contains one or more epoxide moieties per molecule, and (2) a compound that contains one or more primary aliphatic hydroxyl groups per molecule; is catalyzed by: (3) a catalyst compound containing one or more trifluoromethanesulfonate moieties and one or more silyl moieties and run at a temperature of no more than 130.degree. C., such that the catalyst preferably catalyzes reaction at the primary aliphatic hydroxyl group, so that the resulting resin does not gel.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: March 17, 1998
    Assignee: The Dow Chemical Company
    Inventors: Zeng K. Liao, James L. Bertram
  • Patent number: 5726321
    Abstract: Process for carrying out gas/liquid reactions at from (-50.degree.) to 300.degree. C. and from 0.1 to 100 bar by carrying out the reaction in the absence of a continuous gas phase, and, as a special case, a process for the batchwise reaction of acetylene in the liquid phase at from 0.degree. to 300.degree. C. and from 2 to 30 bar, in which acetylene is introduced a) in the absence of a continuous gas phase and b) under isobaric conditions to a degree of saturation of from 5 to 100%.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: March 10, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Bittins, Marc Heider, Martin Schmidt-Radde, Jochen Kellenbenz, Kurt Josef Wagner, Peter Zehner, Stefan Berg
  • Patent number: 5648563
    Abstract: This invention provides a homogeneous retro-retinoid compound, a method of enhancing the growth of a cell in a vitamin A reduced environment, a method for enhancing transcription of a gene regulated by retinoid in a cell, and a method for enhancing an immune response in a subject, wherein the compound has the structure: ##STR1##
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 15, 1997
    Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia University in the City of New York
    Inventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
  • Patent number: 5648564
    Abstract: A process for forming, isolating and purifying xanthophyll crystals, preferably lutein from marigold flower petals, zeaxanthin from wolfberries or capsanthin and capsorubin from red pepper, is disclosed. A xanthophyll diester-containing plant extract is saponified in a composition of propylene glycol and aqueous alkali to form xanthophyll crystals. Crystallization is achieved without the use of added organic solvents. The crystals are isolated and purified. The substantially pure xanthophyll crystals so obtained are suitable for human consumption and can be used as a nutritional supplement and as an additive in food.
    Type: Grant
    Filed: December 21, 1995
    Date of Patent: July 15, 1997
    Assignee: Kemin Industries, Inc.
    Inventors: Rodney L. Ausich, David J. Sanders
  • Patent number: 5608088
    Abstract: A process for producing 3,4-caranediol of the formula [I] includes subjecting 3,4-epoxycarane, which is obtained by epoxidizing 3-carene under specific conditions, to a hydration reaction in the presence of a base catalyst in aqueous ethanol under pressure to obtain 3,4-caranediol.
    Type: Grant
    Filed: September 8, 1995
    Date of Patent: March 4, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keisuke Watanabe, Noboru Yamamoto, Atsushi Kaetsu, Yoshimi Yamada
  • Patent number: 5521221
    Abstract: This invention provides a purified retro-retinoid compound characterized by a molecular mass of about 302 daltons. Also provided by this invention is a method of enhancing the growth of a cell in a vitamin A reduced environment which comprises contacting the cell with an effective growth enhancing amount of a compound having a structure: ##STR1## wherein the configuration of the C6, C8, C10 and C12 double bond independently is Z or E and the absolute configuration at C-14 is independently R or S; wherein R.sub.1 is alkyl, alkyl halide, alcohol, ester, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, acid halide, amide, nitrile, or amine; and wherein R.sub.2 is hydroxyl, halide, alkoxy, ester, alkyl, alcohol, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, nitrile, amine, azide, alkyl halide, acid halide, acid azide, or amide; or wherein R.sub.1 and R.sub.2 are replaced by a 14, 15-oxirane group; and wherein the retro structure is alpha or gamma.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: May 28, 1996
    Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia University in the City of New York
    Inventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
  • Patent number: 5516929
    Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallochloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: May 14, 1996
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Matthias Beller, Brent Blackburn, Yasuhiro Kawanami, Hoi-Lun Kwong, Yasukazu Ogino, Tomoyuki Shibata, Tatsuzo Ukita, Lisa Wang
  • Patent number: 5516950
    Abstract: The present invention relates to the synthesis of D-chiroinositol from a dialdose, comprising the steps of condensing the dialdose by an acyloin condensation reaction to form an inosose, protecting the carbon atoms at the 2, 3, 4 and 5 positions, reducing the ketone of the inosose and removing the protecting groups. In addition, a method of preparing mannodialdose from mannuronic acid is disclosed.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: May 14, 1996
    Assignee: Insmed Pharmaceuticals, Inc.
    Inventors: Thomas Piccariello, Gamini Samanaryke
  • Patent number: 5498734
    Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: March 12, 1996
    Assignee: University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5463142
    Abstract: A method for the preparation of D-chiro-inositol from kasugamycin, comprising the steps of:(a) reacting kasugamycin with an acetylating agent to form a crude hexa-acetate intermediate;(b) purifying the crude intermediate to form purified hexa-acetate intermediate;(c) deacetylating the purified intermediate to form D-chiro-inositol; and(d) isolating the D-chiro-inositol.The method permits efficient, large-scale preparation of D-chiro-inositol without the need for extensive chromatographic purification of the final D-chiro-inositol product.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: October 31, 1995
    Assignee: Abbott Laboratories
    Inventors: David A. Riley, Steven A. Chamberlin, Ashok V. Bhatia
  • Patent number: 5463145
    Abstract: 1,3-Propanediol is prepared in a process comprising the steps of:contacting, in an essentially non-water-miscible organic solvent, ethylene oxide with carbon monoxide and hydrogen in the presence of a catalytic amount of a non-phosphine-ligated cobalt compound and an effective amount of a lipophilic quaternary phosphonium salt promoter at a temperature within the range of about 50.degree. to about 100.degree. C. and a pressure within the range of about 500 to about 5000 psig, to produce an intermediate product mixture comprising less than 15 wt % 3-hydroxypropanal;adding an aqueous liquid to said intermediate product mixture and extracting into said aqueous liquid a major portion of the 3-hydroxypropanal at a temperature less than about 100.degree. C.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Shell Oil Company
    Inventors: Joseph B. Powell, Lynn H. Slaugh, Thomas C. Forschner, Thomas C. Semple, Paul R. Weider
  • Patent number: 5426247
    Abstract: A process for the preparation of vitamin A which preferably comprises bringing cyclogeranyl sulphone into contact with a C.sub.10 aldehyde acetal, halogenating the derivative obtained and then removing the halogen group and the sulphone, removing the acetal group and isomerizing the retinal obtained to the desired configuration. Also disclosed are compounds useful as intermediates in the synthesis of vitamin A and processes for preparation of these intermediate compounds.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: June 20, 1995
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventor: Pierre Chabardes
  • Patent number: 5426248
    Abstract: A process for purifying vitamin A consisting of heating a vitamin A preparation in an inert atmosphere, at a temperature below 170.degree. C. and a pressure of less than 4 mm of mercury, said heating taking place in a vessel shielded from light is disclosed. The vitamin A obtained from this process is mixed with from 0.5:1 to 2:1 parts of tocopherol to vitamin A. The vitamin A and tocopherol mixture can be encapsulated in acacia gum, starch, pectins or other suitable materials. Other antioxidants can be added.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: June 20, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Robert J. Sarama, Michael R. Sevenants, Robert A. Sanders
  • Patent number: 5420366
    Abstract: The present invention provides a process for preparing optically active 2-arylcyclohexanol and its esters and ethers and which process comprises the step of subjecting 1-aryl-cyclohexane-1,2 diol and its diethers and diesters to hydrogenolysis conditions to form said cyclohexanol and its esters and ethers.
    Type: Grant
    Filed: May 11, 1994
    Date of Patent: May 30, 1995
    Assignee: Hoechst Celanese Corporation
    Inventor: Shu-Hai Zhao
  • Patent number: 5406004
    Abstract: A process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a corresponding hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, lactones, and mixtures of two or more thereof which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) supplying to the hydrogenation zone a vaporous feed stream containing hydrogen and a hydrogenatable material selected from monoesters of carboxylic acids, monoesters of dicarboxylic acids, diesters of dicarboxylic acids, lactones, and mixtures of two or more thereof, at an inlet temperature which is above the dew point of the mixture;(c) maintaining the hydrogenation zone under temperature and pressure conditions which are conducive to effecting hydrogenation of esters;(d) recovering from the hydrogenation zone a two phase product stream containing a hydroxylic compou
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: April 11, 1995
    Assignee: Eastman Chemical Company
    Inventors: Philip H. D. Eastland, John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5406005
    Abstract: The invention relates to the synthesis of D-chiro-inositol from glucodialdose comprising the steps of condensing glucodialdose by a acylon condensation reaction, protecting the carbon atoms of the 1,2,5 and 6 position, epimerizing the protected carbon atom at position 5, reducing the ketone of the condensed compound and removing the protect groups.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: April 11, 1995
    Inventor: Thomas Piccariello
  • Patent number: 5395991
    Abstract: A hydrogenation process is described for the production of a hydroxylic compound selected from alcohols and diols by hydrogenation of a corresponding unsaturated organic compound selected from esters, diesters and lactones which involves use of two hydrogenation zones (11, 36), each containing a charge of a hydrogenation catalyst (12, 37). In a first phase of operation one of the hydrogenation zones (36 or 11) is in standby condition and a stream of hot hydrogen-containing gas is passed therethrough. Meanwhile a vaporous feed stream comprising a hydrogen-containing gas and the unsaturated organic compound to be hydrogenated, e.g. dimethyl 1,4-cyclohexanedicarboxylate, is fed to the active zone (11 or 36). This feed stream can include the gas stream from the first mentioned hydrogenation zone (36 or 11).
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5395986
    Abstract: A process is described for the production of cyclohexanedimethanol having a trans-:cis-isomer ratio greater than about 1:1 by hydrogenation of a dialkyl (e.g. dimethyl) cyclohexanedicarboxylate having a trans-:cis-isomer ratio less than about 1:1 which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) supplying to the hydrogenation zone a vaporous feed stream containing hydrogen and a hydrogenarable material comprising a dialkyl cyclohexanedicarboxylate at an inlet temperature which is above its dew point of the mixture;(c) maintaining the hydrogenation zone under temperature and pressure conditions which are conducive to effecting hydrogenation of esters;(d) passing the vaporous feed stream through the hydrogenation zone; and(e) recovering from the hydrogenation zone a product stream containing cyclohexanedimethanol having a trans-:cis-isomer ratio greater than 1:1.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael A. Wood
  • Patent number: 5395987
    Abstract: A continuous process is described for the production of 1,4-cyclohexanedimethanol (CHDM) having a desired or predetermined trans-:cis- isomer ratio by catalytic hydrogenation of a dialkyl 1,4-cyclohexanedicarboxylate in the presence of an ester hydrogenation catalyst. The process is capable of being operated for an extended period of time during which the hydrogenation catalyst declines in catalytic activity and comprises feeding a vaporous mixture of the dialkyl 1,4-cyclohexanedicarboxylate and hydrogen to a hydrogenation zone containing the hydrogenation catalyst and recovering CHDM product. The degree of conversion of the dialkyl 1,4-cyclohexanedicarboxylate at a particular combination of temperature and pressure is related to the trans-:cis- isomer ratio of the CHDM product and may be varied by adjusting at least one feed condition selected from (i) the dialkyl 1,4-cyclohexanedicarboxylate feed rate and (ii) the hydrogen-containing gas:dialkyl 1,4-cyclohexanedicarboxylate molar ratio.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: March 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: Colin Rathmell, Richard C. Spratt, Michael W. M. Tuck
  • Patent number: 5387753
    Abstract: A process is described for reactivating an at least partially deactivated copper-containing ester hydrogenation catalyst which has undergone deactivation through use in hydrogenation of an unsaturated organic compound selected from esters of C.sub.8 to C.sub.22 monocarboxylic acids, diesters of dicarboxylic acids, and lactones, to yield a corresponding hydroxylic compound selected from alcohols and diols which comprises contacting the at least partially deactivated copper-containing catalyst at an effective reactivation temperature and for an effective period of time with a stream of hydrogen-containing gas which is substantially free from the unsaturated organic compound thereby to reactivate the at least partially deactivated copper-containing catalyst.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: February 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael W. M. Tuck, Michael A. Wood
  • Patent number: 5387752
    Abstract: A process is described for the production of cyclohexanedimethanol by hydrogenation of a dialkyl cyclohexanedicarboxylate which comprises:(a) providing a hydrogenation zone containing a charge of a granular heterogeneous ester hydrogenation catalyst;(b) forming a vaporous feed stream of a hydrogen-containing gas,and a hydrogenatable material comprising a dialkyl cyclohexanedicarboxylate at a feed temperature which is in the range of from about 150.degree. C. to about 350.degree. C. and which is above the dew point of the feed stream and at a feed pressure in the range of from about 150 psia (about 10.34 bar) to about 2000 psia (about 137.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: February 7, 1995
    Assignee: Eastman Chemical Company
    Inventors: John Scarlett, Michael A. Wood, Colin Rathmell
  • Patent number: 5382714
    Abstract: A method of isolating, purifying and recrystallizing substantially pure lutein, preferably from saponified marigold oleoresin in its pure free form, apart from chemical impurities and other carotenoids. Lutein may be used as an analytical standard or in cancer prevention trials and as a safe and effective color additive for human food.
    Type: Grant
    Filed: March 17, 1994
    Date of Patent: January 17, 1995
    Assignee: The Catholic University of America
    Inventor: Frederick Khachik
  • Patent number: 5372995
    Abstract: Described is a two-step process for producing phenyl- and cyclohexyl-substituted oxybutane derivative-containing mixtures of our invention by means of first reacting methyl ethyl ketone with benzaldehyde in the presence of a sulfonic acid catalyst to produce a mixture of phenyl pentenone derivatives; and then hydrogenating the resulting mixture of phenyl pentenone derivatives in the presence of a hydrogenation catalyst, as well as the product produced thereby; and perfumery uses thereof for augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: December 13, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna
  • Patent number: 5342903
    Abstract: A process for the preparation of adducts by reacting an alcohol with an epoxy compound in the presence of a catalyst, which comprises reacting an alcohol of formula I ##STR1## wherein A is an aliphatic, cycloaliphatic or araliphatic radical and r is a number from 1 to 10, with a mono- or diepoxide in the equivalent ratio of 1:20 to 20:1, based on the hydroxyl and epoxy groups, in the presence of a metal complex of formula II as catalyst[M.sup.n+ (L.sub.1).sub.x (L.sub.2).sub.y (L.sub.3.sup.m-).sub.z ][X.sup.k- ].sub.(n-zm)/k (II),whereinM is a metal of the main groups or subgroups of the Periodic Table of the Elements,L.sub.1 and L.sub.2 are weakly bonded, neutral, unidentale or multidentate ligands,L.sub.3 is a strongly bonded, non-replaceable neutral or anionic unidentale or multidentate ligand,X is an anion of the following formulae BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, ClO.sub.4.sup.-, IO.sub.4.sup.-, NO.sub.3.sup.
    Type: Grant
    Filed: April 30, 1993
    Date of Patent: August 30, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Wolleb, Andreas Hafner, William M. Rolfe
  • Patent number: 5329053
    Abstract: A novel process is described for the manufacture of a mixture of 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-3-en-1-ol and -4-en-1-ol (I) and, respectively, of a mixture of [3a.alpha.,5a.beta.,9a.alpha.,9b.beta.]-dodecahydro-3a,6,6,9a-tetramethyln aphtho[2,1-b]furan and [3a.alpha.,5a.beta.,9a.alpha.,9b.alpha.
    Type: Grant
    Filed: August 25, 1993
    Date of Patent: July 12, 1994
    Assignee: Givaudan-Roure Corporation
    Inventor: Daniel Helmlinger
  • Patent number: 5329052
    Abstract: The invention relates to novel odorants derived from formylpinane. In particular, these are compounds of the formula ##STR1## in which R represents H or C--C alkyl, for example methyl, ethyl, propyl, butyl etc., preferably methyl or ethyl, preferably methyl or ethyl, n represents 0 or 1 and the notation represents a single or double bond I.
    Type: Grant
    Filed: August 5, 1993
    Date of Patent: July 12, 1994
    Assignee: Givaudan-Roure Corporation
    Inventors: Bernard Auger, Jerzy A. Bajgrowicz, Edouard Giraudi
  • Patent number: 5306846
    Abstract: There are disclosed novel processes for the synthesis of novel intermediates useful in the of further synthesis of cyclitols and derivatives thereof.
    Type: Grant
    Filed: December 6, 1991
    Date of Patent: April 26, 1994
    Assignee: Virginia Tech Intellectual Properties
    Inventor: Thomas Hudlicky
  • Patent number: 5292971
    Abstract: Fluorine-substituted vicinal glycols of the formula ##STR1## in which the substituents R.sub.1 to R.sub.4, independently of one another, have the following meanings: R.sub.1 to R.sub.4 =H, fluorine, C.sub.1 - to C.sub.18 -alkyl in which some or all of the hydrogens may be substituted by fluorine, and at least one of the substituents R.sub.1 to R.sub.4 is a completely fluorinated alkyl or an alkyl of the formula--(CH.sub.2).sub.m --(C.sub.n F.sub.2n+1),in which m is 1 or 2, and n is an integer from 1 to 17, and x is 0 or 1.Furthermore, a method for the preparation of the fluorinated vicinal glycols is described. If the fluorinated vicinal glycols are condensed together with dicarboxylic acids, products having enhanced thermal stability are obtained.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: March 8, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Kulpe, Heinz Strutz
  • Patent number: 5264638
    Abstract: A process for the extraction and purification of the diterpene alcohol Plaunotol from the leaves of the medicinal plant, Croton sublyratus Kurz. The process involves extracting firstly with a lower aliphatic alcohol followed by extracting from the alcohol solution with a chlorinated hydrocarbon. Then impurities are hydrolysed and the required Plaunotol separated by extraction with a hydrocarbon. This process is simple and gave much better yields than prior processes.
    Type: Grant
    Filed: January 28, 1992
    Date of Patent: November 23, 1993
    Assignee: Chulalongkorn University
    Inventor: Naline Nilubol
  • Patent number: 5260461
    Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, an aqueous solution, a base, a ferricyanide salt and an osmium-containing compound are combined. The chiral ligand is an alkaloid or alkaloid derivative linked to an organic substituent of at least 300 daltons molecular weight through a planar aromatic spacer group. The organic substituent can be another alkaloid or alkaloid derivative. With the described chiral ligands, asymmetric dihydroxylation of olefins with high yields and enantiomeric excesses are achieved.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: November 9, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Jens Hartung, K. Barry Sharpless
  • Patent number: 5250512
    Abstract: An optically active 3-[6(S)-2,2,6-trimethylcyclohexan-1-yl]propanol derivative represented by formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl group, and a perfume containing the same as an active ingredient are disclosed.
    Type: Grant
    Filed: May 6, 1992
    Date of Patent: October 5, 1993
    Assignee: Takasago International Corporation
    Inventors: Tatsuya Ohmoto, Akemi Shimada, Takeshi Yamamto
  • Patent number: 5243094
    Abstract: Derivatives of long-chain fatty alcohols, and methods of obtaining them, are provided, as well as pharmaceutical compositions containing derivatives and their uses, in particular in treating or preventing neuro-degenerative illnesses, conditions linked to skin ageing, the phenomena of thrombosis and atherosclerosis, and immune deficiencies.
    Type: Grant
    Filed: July 11, 1991
    Date of Patent: September 7, 1993
    Assignee: Medafor
    Inventor: Jacques Borg
  • Patent number: 5229425
    Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing substantially all of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml. of said broth, containing not more than 0.06 ml of said oxidized limonene per ml. of said broth and incubated at 37.degree. C. in air for 60 minutes.
    Type: Grant
    Filed: May 29, 1992
    Date of Patent: July 20, 1993
    Assignee: Doyle E. Chastain
    Inventors: Doyle E. Chastain, W. E. Sanders, Jr., Christine C. Sanders
  • Patent number: 5227543
    Abstract: Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant, an osmium-containing compound and an organic soluble anion are combined. The presence of the organic soluble anion allows the asymmetric dihydroxylation reaction to occur rapidly and the amount of olefin that is diydroxylated is high with concomitantly less chiral ligand and osmium-containing catalyst than previously achieved.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: July 13, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: K. Barry Sharpless, Wihelm K. Amberg
  • Patent number: 5225579
    Abstract: There is provided a method with which vitamin D.sub.2, vitamin D.sub.3, activated type vitamin D.sub.2, activated type vitamin D.sub.3 and their derivatives are prepared from 7,8 -dihyroxy vitamin D.sub.2, D.sub.3 or any of their derivatives by means of a reducing elimination technique involving as cyclic orthoester of a 7,8-dihydroxy compound or a thiocarbonate compound as an intermediate compound or an elimination technique utilizing a reducing metal such as titanium. The method according to the invention ensures a practical and simple synthetic process and a high yeild as compared with any existing methods for manufacturing these chemicals.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: July 6, 1993
    Assignee: Hoxan Corporation
    Inventor: Yuji Tahara
  • Patent number: 5221788
    Abstract: A polyurethane polyol obtained by reacting a hydrocarbon diol of the formula (A):HO--R--OH (A)wherein R is a C.sub.7-20 linear or branched alkylene group, with isophorone diisocyanate and having a number average molecular weight of from 500 to 20,000.
    Type: Grant
    Filed: September 3, 1992
    Date of Patent: June 22, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Junichi Goto, Takayuki Ohta
  • Patent number: 5206229
    Type: Grant
    Filed: October 10, 1990
    Date of Patent: April 27, 1993
    Assignee: Leo Pharmaceutical Products LTD
    Inventors: Martin J. Calverley, Lise Binderup, Ernst T. Binderup
  • Patent number: 5202502
    Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: April 13, 1993
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5169993
    Abstract: The invention provides cyclohexenol derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; and R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group, with the provisos that when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom then n is not 0 and, when R.sup.1, R.sup.2 and R.sup.3 all represent a hydrogen atom and n is 1, R does not represent a fluorine atom substituted at the 4-position of the phenyl ring; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidal active cyclopentane derivatives.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: December 8, 1992
    Assignee: Shell Research Limited
    Inventor: Paul H. Briner
  • Patent number: 5153229
    Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing at least 99.99% of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml.
    Type: Grant
    Filed: June 1, 1990
    Date of Patent: October 6, 1992
    Assignee: Doyle E. Chastain
    Inventors: Doyle E. Chastain, W. Eugene Sanders, Jr., Christine C. Sanders
  • 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: 5149880
    Abstract: Nitrogen-containing aromatic heterocyclic ligand-metal complexes and their use for the activation of hydrogen peroxide and dioxgen are disclosed. Processes whereby activated hydrogen peroxide or dioxygen are used to transform various organic substrates are also disclosed. In particular, processes for the conversion of methylenic carbons to carbonyls, for the dioxygenation of aryl olefins, acetylenes and aryl-.alpha.-diols, for the oxidation of alcohols and aldehydes and for the removal of mercaptans from gaseous streams and for the removal of hydrogen sulfide and/or mercaptans from liquid streams are disclosed.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: September 22, 1992
    Assignee: The Texas A & M University System
    Inventors: Donald T. Sawyer, Ceshing Sheu, Andrzej Sobkowiak, Hui-Chan Tung
  • Patent number: 5104851
    Abstract: A 2-(alkyl-cyclohexyl)-1-propanol is disclosed. The compound is represented by formula (I): ##STR1## wherein R.sub.1 and R.sub.2 individually represent a group selected from the members consisting of methyl-, ethyl-, n-propyl-, i-propyl-, t-butyl-, and sec-butyl groups, provided that the total carbon atoms of the R.sub.1 and R.sub.2 groups are 4 to 7; either R.sub.1 and R.sub.2 is a hydrogen atom, the other being a cyclohexyl group; or R.sub.1 and R.sub.2 together form a hexamethylene ring together with 2 carbon atoms in the cyclohexane ring. The compound possesses a long-lasting, woody, floral odor, and can be widely used as perfumery materials such as perfumes, soaps, shampoos, aromatic goods, and detergents.
    Type: Grant
    Filed: January 25, 1991
    Date of Patent: April 14, 1992
    Assignee: Kao Corporation
    Inventors: Yoshiaki Fujikura, Hiroaki Ohnuma, Manabu Fujita, Nao Toi
  • Patent number: 5095155
    Abstract: Closely boiling diastereomeric isomer alcohols are separated by converting them to esters having disparate boiling points, separating the ester isomers by distillation and saponifying the separate ester isomers to obtain the individual alcohol isomers.
    Type: Grant
    Filed: June 7, 1990
    Date of Patent: March 10, 1992
    Assignee: Union Camp Corporation
    Inventor: Peter W. D. Mitchell
  • Patent number: 5030772
    Abstract: This invention relates to hydroxylated derivatives of vitamin D.sub.2 and a process for preparing such compounds. In particular, a process for preparing the 24-epimer of vitamin D.sub.2 and the corresponding 1.alpha.-hydroxylated derivative thereof is disclosed. The vitamin D.sub.2 derivatives would find application in the treatment of or prophylaxsis for various disease states characterized by calcium and phosphorous imbalances.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: July 9, 1991
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Shigeya Okada