Cyclohexane Polyol (e.g., Inositol, Etc.) Patents (Class 568/833)
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Publication number: 20010000035Abstract: A process for the reaction of an organic compound in the presence of a catalyst comprising, as active metal, ruthenium alone or together with at least one Group Ib, VIIb, or VIIIb metal in an amount of from 0.01 to 30 wt %, based on the total weight of the catalyst, applied to a support, wherein from 10 to 50% of the pore volume of the support comprises macropores having a pore diameter in the range of from 50 nm to 10,000 nm and from 50 to 90% of the pore volume of the support comprises mesopores having a pore diameter in the range of from 2 to 50 nm, the sum of said pore volumes being 100%, and said catalyst as such.Type: ApplicationFiled: November 30, 2000Publication date: March 15, 2001Inventors: Thomas Ruhl, Boris Breitscheidel, Jochem Henkelmann, Andreas Henne, Rolf Lebkucher, Konard Knoll, Paul Naegele, Hermann Gausepohl, Sabine Weiguny, Norbert Niessner
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Patent number: 6150568Abstract: Disclosed is the compound valiolone, which has the formula (I): ##STR1## a method of preparing valiolone, and a method of using valiolone to prepare acarbose and voglibose.Type: GrantFiled: March 30, 1999Date of Patent: November 21, 2000Assignee: University of WashingtonInventors: Heinz G. Floss, Sungsook Lee, Ingo Tornus
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Patent number: 5969190Abstract: The compound, (E)-(1R,3R)-5-[(R)-11-hydroxy-7,11-dimethyl-dodec-2-enylidene]-cyclohexane -1,3-diol of the formula I: ##STR1## is useful in the treatment or prevention of hyperproliferative skin diseases, particularly psoriasis, basal cell carcinomas, disorders of keratinization and keratosis; or for reversing the conditions associated with photodamage.Type: GrantFiled: May 15, 1998Date of Patent: October 19, 1999Assignee: Hoffmann-La Roche Inc.Inventors: Franz Bauer, Lawrence F. Courtney
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Patent number: 5959153Abstract: Process for decomposing a mixture containing cycloalkylhydroperoxide, which mixture includes an organic phase and an aqueous phase wherein, during the decomposition, at least one compound is present which meets the following parameters:A>-0.5 and B>-1.0 (1)A and B being dependent on T.sub.b, .rho., n.sub.d, .epsilon..sub.r, .delta..sub.d, .delta..sub.p, .delta..sub.h, .delta., .mu. and E.sub.T(30), where T.sub.b is the normal boiling point (.degree. C.), .rho. is the density measured at 25.degree. C. (kg/m.sup.3), n.sub.d is the refractive index (-), .epsilon..sub.r is the relative dielectric constant (-), .delta..sub.d is the Hansen solubility parameter for a dispersion (MPa.sup.1/2), .delta..sub.p is the Hansen solubility parameter for polarity (MPa.sup.1/2), .delta..sub.h is the Hansen solubility parameter for hydrogen bridges (MPa.sup.1/2), .delta. is the Scatchard-Hildebrant solubility parameter (MPa.sup.1/2), .mu. is the dipole moment (Debey), and E.sub.Type: GrantFiled: March 11, 1998Date of Patent: September 28, 1999Assignee: DSM N.V.Inventors: Ubaldus F. Kragten, Henricus A. C. Baur
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Patent number: 5959161Abstract: To offer a method of producing useful para-menthane-3,8-diol having the excellent repellent action to harmful living things, including noxious insects, in high purity and high yield, simply, and economically by the use of citronellal as a raw material compound.The above-mentioned problems are resolved by the production method of this invention wherein citronellal is treated with aqueous sulfuric acid solution of 0.02 to 1.0 wt. % in concentration to produce para-menthane-3,8-diol. In case of recovering the produced para-menthane-3,8-diol, a method is preferably adopted, wherein after the reaction product is extracted with an aliphatic hydrocarbon solvent of 5 to 8 in carbon number, the extract is cooled down at temperature higher than the melting point of said aliphatic hydrocarbon solvent and of -10.degree. C. or less to crystallize para-menthane-3,8-diol.Type: GrantFiled: October 27, 1998Date of Patent: September 28, 1999Assignee: Takasago International CorporationInventors: Hiroyuki Kenmochi, Teruyoshi Akiyama, Yoshifumi Yuasa, Toyohiko Kobayashi, Akio Tachikawa
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Patent number: 5932774Abstract: 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: GrantFiled: November 6, 1995Date of Patent: August 3, 1999Assignee: Abbott LaboratoriesInventors: David A. Riley, Ashok V. Bhatia, Steven A. Chamberlin, Gregg E. Robinson
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Patent number: 5919986Abstract: Compounds of formula I: ##STR1## wherein the dotted carbon-carbon bond in the D-ring is C--C or C.dbd.C; C(R,R) is CH.sub.2 or C.dbd.CH.sub.2,R.sup.1 is H, F or OH,R.sup.2 and R.sup.3 are each independently C.sub.1-4 -alkyl or CF.sub.3, or together with the carbon to which they are bound form C.sub.3-6 -cycloalkyl.are useful in the treatment of vitamin D dependent disorders, such as psoriasis, leukemia; acne and seborrhoic dermatitis; osteoporosis hyperparathyroidism accompanying renal failure; and multiple sclerosis.Type: GrantFiled: October 13, 1998Date of Patent: July 6, 1999Assignee: Hoffmann-la Roche Inc.Inventors: Pierre Barbier, Franz Bauer, Peter Mohr, Marc Muller, Wolfgang Pirson
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Patent number: 5911992Abstract: A method of controlling weight in mammals by orally administering to the mammal an amount of a pharmaceutical composition containing Hypericum perforatum or active components thereof effective to control the weight of the mammal is described. The pharmaceutical composition also preferably further contains at least one thermogenic agent and at least one agent inhibiting lipogenesis. The at least one thermogenic agent includes one or more of N-acetyl-L-carnitine, cayenne extract, inositol hexanicotinate, niacin or salicin. The at least one agent inhibiting lipogenesis may be hydroxy citric acid. When the pharmaceutical composition includes Hypericum perforatum, at least one thermogenic agent and at least one agent inhibiting lipogenesis, the composition acts to control the weight of the mammal by simultaneously suppressing appetite, inducing thermogenesis and inhibiting lipogenesis.Type: GrantFiled: June 12, 1997Date of Patent: June 15, 1999Assignee: A. Glenn BraswellInventors: A. Glenn Braswell, Aftab J. Ahmed
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Patent number: 5756774Abstract: Provided herein are novel syntheses of the phosphate-based inositol derivatives 1-O-?(+)-menthoxycarbonyl!-6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inos itol (D4P), D-myo-inositol 1,4,5-trisphosphate (D-IP.sub.3), 6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol H-phosphonate ((-)-3-HP) and L-myo-inositol 1,4,5-trisphosphate (L-IP.sub.3). These syntheses employ fewer column chromatography steps for the isolation of intermediates than do prior art syntheses, and hence, are more convenient, economical and efficient than are the previously known synthetic methods.Type: GrantFiled: February 4, 1997Date of Patent: May 26, 1998Inventors: Robert Bittman, Lawrence Leung
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Patent number: 5714643Abstract: An aqueous solution of kasugamycin or its salt is either mixed with a strongly acidic ion-exchange resin of the H.sup.+ -form in a reaction vessel, or is brought into contact with a strongly acidic ion-exchange resin of the H.sup.+ -form in a column containing said resin, followed by heating said aqueous solution and the resin under an atmospheric pressure or an elevated pressure, thereby to effect hydrolytic reaction of kasugamycin. By this reaction, an acidic reaction solution containing D-chiro-inositol is produced. This acidic reaction solution containing D-chiro-inositol is separated from the strongly acidic ion-exchange resin. Subsequently, D-chiro-inositol is recovered from the reaction solution. For this recovery, the acidic reaction solution is passed successively through a column of a strongly acidic ion-exchange resin of the H.sup.+ -form and through a column of a strongly basic ion exchange resin of the OH.sup.- -form, so that a neutral aqueous eluate containing D-chiro-inositol is obtained.Type: GrantFiled: February 9, 1996Date of Patent: February 3, 1998Assignees: Hokko Chemical Co., Ltd., Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Kiyoshi Sato, Makoto Yoshida, Kenji Kanbe, Kiyoshi Hirazawa, Tomio Takeuchi
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Patent number: 5675043Abstract: A process for the removal of nitrogen-containing compounds from a hydrocarbon blend using a solvent with a liquid-phase density at 25.degree. C. not less than 0.90 g/cm.sup.3, and a Hansen polar solubility parameter .delta..sub.P, and a Hansen hydrogen bonding parameter .delta..sub.H, such that at 25.degree. C.9.0(Cal/cm.sup.3).sup.1/2 <(.delta..sub.P +.delta..sub.H)<28.0(Cal/cm.sup.3).sup.1/2.The process is useful for purifying feedstocks to catalytic conversion processes, particularly etherification processes used in the production of ether-rich additives for gasoline.Type: GrantFiled: November 21, 1995Date of Patent: October 7, 1997Inventors: Christopher P. Eppig, E. T. Robinson, Paul Greenough
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Patent number: 5633412Abstract: There are described novel biocatalytic and chemical processes for the synthesis of various oxygenated compounds. Particularly, there are described processes for the synthesis of a useful synthon 12 made by reacting a protected diol (acetonide) with permaganate under appropriate conditions. Such synthon is useful of the synthesis of various pharmaceutically important compounds such as D-chiro-inositol and D-chiro-3-inosose. Also, there are disclosed novel compounds, including specifically the synthon 12 and compounds derived therefrom.Type: GrantFiled: March 24, 1995Date of Patent: May 27, 1997Assignee: Virginia Tech Intellectual PropertiesInventors: Tomas Hudlicky, Martin Mandel
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Patent number: 5602287Abstract: There are described novel biocatalytic and chemical processes for the synthesis of various oxygenated compounds. Particularly, there are described processes for the synthesis of a useful synthon 12 made by reacting a protected diol (acetonide) with permaganate under appropriate conditions. Such synthon is useful of the synthesis of various pharmaceutically important compounds such as D-chiro-inositol and D-chiro-3-inosose. Also, there are disclosed novel compounds, including specifically the synthon 12 and compounds derived therefrom.Type: GrantFiled: March 24, 1995Date of Patent: February 11, 1997Assignee: Virginia Tech Intellectual PropertiesInventors: Tomas Hudlicky, Martin Mandel
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Patent number: 5597932Abstract: The invention is drawn to a compound having the following formula ##STR1## in which X.sup.1 and X.sup.2, which may be the same or different, represent hydrogen or a hydroxy-protecting group, X.sup.4 is hydrogen, A is selected from --COOAlkyl and CH.sub.2 OH, and B is a hydroxy group, or A and B, when taken together, represent an oxo group. These compounds are useful as intermediates in the production of 19-nor vitamin D derivatives.Type: GrantFiled: May 16, 1995Date of Patent: January 28, 1997Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
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Patent number: 5574180Abstract: Described is a process for recovering phytic acid or phytic acid salt from a medium in which it is contained. This process includes contacting the medium with a solid-phase free base polymer having tertiary amine functions to adsorb the phytic acid or salt thereof. In one preferred mode, the medium to be treated also contains lactic acid, and separate fractions predominant in (i) lactic acid and (ii) phytic acid or phytic acid salt, respectively, are recovered. Also described are preferred processes for treating mediums to recover lactic acid therefrom, and a favored process for obtaining inositol directly by hydrolyzing phytic acid or phytic acid salt while adsorbed on a pyridine-containing polymer.Type: GrantFiled: August 1, 1994Date of Patent: November 12, 1996Assignee: Reilly Industries, Inc.Inventors: Donald McQuigg, Charles Marston, Gina Fitzpatrick, Ernest Crowe, Susan Vorhies, Ramiah Murugan, Thomas D. Bailey
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Patent number: 5516929Abstract: 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: GrantFiled: February 12, 1993Date of Patent: May 14, 1996Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Matthias Beller, Brent Blackburn, Yasuhiro Kawanami, Hoi-Lun Kwong, Yasukazu Ogino, Tomoyuki Shibata, Tatsuzo Ukita, Lisa Wang
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Patent number: 5516950Abstract: 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: GrantFiled: February 14, 1995Date of Patent: May 14, 1996Assignee: Insmed Pharmaceuticals, Inc.Inventors: Thomas Piccariello, Gamini Samanaryke
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Patent number: 5482631Abstract: When a strong base anion exchange resin, such as a chloride-form strong base anion exchange resin, is conditioned with a low concentration of hydroxyl (for example, an NaOH solution with a concentration between 1 and 10 mM), the conditioned resin separates in, sit, Is from sugars and sugar alcohols, while still allowing ready desorption of the sugars from the resin. The feedstock is first passed over a column containing this conditioned resin, followed by a mobile phase solvent, preferably water. The inositols have a lower affinity for the treated resin than do the sugars and sugar alcohols in the feedstock, and therefore pass through the column more quickly. The process may economically be performed on industrial-scale inositol separations, particularly when used in a preferred simulated moving bed chromatographic system.Type: GrantFiled: October 6, 1994Date of Patent: January 9, 1996Assignee: Board of Supervisors of Louisiana State University and Agricultural and Mechanical CollegeInventors: Michael Saska, Moustapha Diack
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Patent number: 5463142Abstract: 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: GrantFiled: November 10, 1994Date of Patent: October 31, 1995Assignee: Abbott LaboratoriesInventors: David A. Riley, Steven A. Chamberlin, Ashok V. Bhatia
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Patent number: 5406005Abstract: 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: GrantFiled: April 15, 1994Date of Patent: April 11, 1995Inventor: Thomas Piccariello
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Patent number: 5344946Abstract: The present invention provides a process for the preparation of vicinal diols and/or epoxides by the oxidation of olefinically-unsaturated compounds with the use of an inorganic heptavalent rhenium compound as catalyst and of hydrogen peroxide as oxidation agent, wherein the reaction is carried out in a solvent selected from the group consisting of organic phosphoric acid esters and ethers with a boiling point above 50.degree. C. under atmospheric conditions.Type: GrantFiled: May 20, 1993Date of Patent: September 6, 1994Assignee: Solvay Interox GmbHInventors: Siegfried Warwel, Mark R. Klaas, Michael Sojka
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Patent number: 5260472Abstract: Multigram quantities of Ins(1,4,5) P.sub.3, Ins(1,3,4) P.sub.3, and Ins(1,3,4,5)P.sub.4 are prepared in their enantiomerically pure forms from the two enantiomers of 1,2:5,6-di-O-cyclohexylidene myo-inositol. Also, a facile enzymatic preparation is also described of these chiral precursors through enantiospecific deacylation of the corresponding racemic esters is disclosed.Type: GrantFiled: January 29, 1992Date of Patent: November 9, 1993Assignee: The Board of Governors for Higher Education State of Rhode Island and Providence PlantationsInventor: Ching-Shih Chen
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Patent number: 5260495Abstract: The invention relates to highly selective, heterogeneous hydrotalcite-type catalysts for the production of monoalkylene glycol by hydrolysis of the corresponding alkylene oxide. The invention also relates to method of preparing these catalysts using large organic anion spacers, and a process for producing monoalkylene glycol.Type: GrantFiled: August 4, 1992Date of Patent: November 9, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Matthew W. Forkner
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Patent number: 5250743Abstract: In accordance with the present invention, a method for the interconvertion of the enantiomers of acyclic 1,2-dihydroxy-3-alkenes or for converting either enantiomer of acylic 1,2-dihydroxy-3-alkenes to the corresponding antipodal 1-hydroxy-2-alkoxy-3-alkene compounds has been discovered, comprising reacting in an acidic reaction media either enantiomer of an acylic vinyl epoxide (which can be derived from the corresponding acyclic 1,2-dihydroxy-3-alkene) with water, alcohol, or a mixture thereof. When substantially optically pure acyclic vinyl epoxide compounds are employed in the inventive method, the interconverted acyclic 1,2-dihydroxy-3-alkene or 1-hydroxy-2-alkoxy-3-alkene compound products are also substantially optically pure.Type: GrantFiled: December 31, 1992Date of Patent: October 5, 1993Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 5214180Abstract: Phosphatidylinositol of high purity useful for the treatment of central nervous system disorders, prepared from vegetal substances containing it by treating them with reagents suitable for the functionalization of the inositol hydroxy group with protective groups, separating the thus protected phosphatidylinositol by solvent extraction or chromatography, and finally removing said protective groups under conditions which do not modify the phosphatidyl group.Type: GrantFiled: January 16, 1992Date of Patent: May 25, 1993Assignee: Mediolanum Farmaceutici S.p.A.Inventors: Enrico Ferrari, Pier Giuseppe Pagella, Stefano Maiorana, Mario Brufani
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Patent number: 5210336Abstract: A process is provided for the conversion of an olefin to the corresponding glycol wherein a mixture of olefin, oxygen, carbon dioxide and water is reacted in a solvent at supercritical conditions with respect to the reaction mixture.Type: GrantFiled: January 24, 1992Date of Patent: May 11, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Anne M. Gaffney, John A. Sofranko
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Patent number: 5126494Abstract: 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 metallo-chloramine 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: GrantFiled: April 23, 1990Date of Patent: June 30, 1992Assignee: Massachusetts Institute of TechnologyInventors: Declan Gilheany, Byeong M. Kim, Hoi-Lun Kwong, K. Barry Sharpless, Tomoyuki Shibata
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Patent number: 5096594Abstract: A method of purifying cyclitols, particularly inositol, from mixtures including simple and complex carbohydrates begins by reducing the concentration of carbohydates other than cyclitols to facilitate separation and crystallization of the cyclitol in high purity. This separation can be achieved by separating carbohydrates on a chromatographic column then concentrating and crystallizing cyclitol from selected fractions.Type: GrantFiled: December 20, 1990Date of Patent: March 17, 1992Inventor: Israel Rabinowitz
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Patent number: 5091596Abstract: Kasugamycin has been recognized to be a source from which D-chiro-inositol can be easily obtained at low cost and high yield.Type: GrantFiled: December 20, 1990Date of Patent: February 25, 1992Assignee: Univ. of Va. Alumni Patents FoundationInventors: Allison Kennington, Joseph Larner, Cynthia Hill, Butler Stringfield, Giorgio Carta, Donald J. Kirwan
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Patent number: 5066815Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a carbonyl compound in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: May 8, 1990Date of Patent: November 19, 1991Assignee: Takasago International CorporationInventors: Noboru Sayo, Hidenori Kumobayashi, Susumo Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 5019658Abstract: The instant invention is an improvement in the method of producing optically pure sterioisomers from a racemic mixture. The method is based on the well-known fact that a supersaturated solution or melt of the racemic mixture can be seeded with just the crystals of the desired stereoisomer, which will then crystallize out selectively, leaving the undesired stereoisomer behind in the liquid mother liquor. The desired isomer, in crystaline form, can then be separated by simple liquid/solid separation from the undesired isomer remaining behind in the mother liquor. In the conventional method, supersaturation is achieved by careful cooling of a saturated solution or melt. In the present invention, supersaturation is achieved by increasing the ambient pressure over the saturated solution or melt of the racemic mixture, and relying on the fact that the melting temperature of a substance increases with increasing pressure, provided there is an increase in molar volume when the substance melts.Type: GrantFiled: October 23, 1989Date of Patent: May 28, 1991Assignee: Kobe Steel LimitedInventor: Robert P. Cahn
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Patent number: 4997489Abstract: The invention relates to a process for recovering sugar, sugar alcohol and organic acids comprising citric, malic and quinic acids from a juice extracted from almond hulls. Residues from the extraction is also recovered.Type: GrantFiled: May 8, 1989Date of Patent: March 5, 1991Inventor: Israel N. Rabinowitz
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Patent number: 4988682Abstract: The present invention relates to a method for inhibiting the phosphatidylinositol cycle in a cell by contacting the cell with certain myo-inositol analogs. Such myo-inositol analogs can also be utilized to treat phosphatidylinositol cycle-dependent conditions. The present invention also provides novel myo-inositol analogs.Type: GrantFiled: February 3, 1989Date of Patent: January 29, 1991Assignee: University of PittsburghInventor: Alan P. Kozikowski
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Patent number: 4982017Abstract: A composition for use in synthesis reactions comprises a mixture of an organolithium compound and an inert inorganic pulverulent carrier and consists of methyllithium and ethyllithium, one or more of the group consisting of SiO.sub.2, Al.sub.2 O.sub.3, CaO and synthetic anhydrous aluminosilicate, and paraffin. That composition is flowable and non-pyrophoric.Type: GrantFiled: May 3, 1989Date of Patent: January 1, 1991Assignee: Metallgesellschaft AktiengesellschaftInventors: Jurgen Deberitz, Wilfried Weiss
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Patent number: 4982021Abstract: Alkylene glycols are produced by the reaction of alkylene oxide with water in the presence of a metalate-containing solid wherein the metalate is in association with electropositive complexing sites on a solid support such as an anion exchange resin.Type: GrantFiled: June 8, 1988Date of Patent: January 1, 1991Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Robert D. Best, Joseph A. Collier, Brian T. Keen, John H. Robson
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Patent number: 4967018Abstract: A process for the catalytic hydrolysis of alkylene oxide to alkylene glycol using a hydrothermally stable, mixed metal framework catalyst composition selected from(a) material having the formulaM.sub.x.sup.2+ Q.sub.y.sup.3+ (OH) 2x+3y-nz A.sub.z.sup.n-. a 1 H.sub.2 O (I)wherein M is at least one divalent metal cation; Q is at least one trivalent metal cation; and A is at least one anion providing a valence (n.sup.31), wherein n is at least 1, and wherein a is a positive number, M, Q, and A are provided in a proportion such that x/y is a number equal to or greater than 1, z has a value greater than zero and 2x+3y-nz is a positive number, and M, Q and A are selected to provide a layered structure, and(b) material prepared by calcining the material of formula (I) having the formulaM.sub.x.sup.2+ Q.sub.y.sup.3+ (O).sub.(2x+3y-nz)/2D.sub.z.sup.n-(II)wherein M, Q, x, y, z and n have the same meanings defined above in connection with formula (I) and D is at least one nonvolatile anion.Type: GrantFiled: October 18, 1989Date of Patent: October 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Hwaili Soo, Bernard C. Ream, John H. Robson
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Patent number: 4929777Abstract: Disclosed are catalyst compositions comprised of chemically-mixed, copper-titanium oxides and the use of such catalyst compositions in the hydrogenation of certain esters to obtain the alcohol corresponding to the acid residue of the ester.Type: GrantFiled: February 13, 1989Date of Patent: May 29, 1990Assignee: Eastman Kodak CompanyInventors: Gether Irick, Jr., Patricia N. Mercer, Kenneth E. Simmons
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4885409Abstract: Process for the hydrogenation of bis-phenols by reacting bis-phenols with hydrogen in the presence of a catalytic system consisting of palladium supported on activated carbon.Type: GrantFiled: May 4, 1988Date of Patent: December 5, 1989Assignee: Montedison S.p.A.Inventors: Andrea Gardano, Francesco Casagrande, Marco Foa, Guido Petrini, Riccardo Barisone, Lawrence Chapoy
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Patent number: 4801759Abstract: A method for the continuous saponification of epoxides with 3-8 carbon atoms at low pressures, preferably atmospheric pressure, and low boiling temperatures with small amounts of water. Yields and selectivities are very high.Type: GrantFiled: August 7, 1987Date of Patent: January 31, 1989Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gu Prescher, Helmut Maurer
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Patent number: 4760200Abstract: The process for the liquid-phase hydration of a vicinal alkylene oxide(s) to the corresponding alkylene glycol(s) comprising carrying out such hydration in an aqueous medium containing a water miscible alkylene glycol ether co-solvent.Type: GrantFiled: December 31, 1985Date of Patent: July 26, 1988Assignee: Union Carbide CorporationInventors: Brian T. Keen, John H. Robson, George E. Keller, II
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Patent number: 4740638Abstract: Novel substituted cis-1,2-dihydroxy-cyclohexa-3,5-diene compounds, useful as intermediates in the production of phenols and catechols for use as intermediates in the production of drugs, herbicides, insecticides and as chiral synthons, in particular cis-1,2-dihydroxy-3-trifluoromethyl-cyclohexa-3,5-diene. A process for producing the novel compounds is also claimed.Type: GrantFiled: June 9, 1987Date of Patent: April 26, 1988Assignee: Imperial Chemical Industries PLCInventors: Stephen C. Taylor, Michael D. Turnbull
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Patent number: 4711875Abstract: Composition consisting of from less than 100% to more than about 80% of trans-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol and a definite amount, but not more than about 20%, of cis-1-(2,6,6-trimethylcyclohexyl)-hexan-3-ol.Process for preparing same from .beta.-cyclocitral via a three-, optionally, four-step pathway.Utilization of the said composition as effective perfume ingredient.Type: GrantFiled: October 17, 1985Date of Patent: December 8, 1987Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Gunther Ohloff, Bernard L. Muller, Wolfgang K. Giersch
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Patent number: 4701571Abstract: An improved process for the hydrolysis of alkylene oxide to produce alkylene glycol which comprises:(a) reacting alkylene oxide and water in the presence of a selectivity-enhancing metalate-containing solid until about 90-95% of the alkylene oxide is converted to alkylene glycol; and(b) completing the hydrolysis reaction of (a) in the absence of the selectivity-enhancing metalate-containing solid.Type: GrantFiled: June 30, 1986Date of Patent: October 20, 1987Assignee: Union Carbide CorporationInventors: Hwaili Soo, John H. Robson
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Patent number: 4626603Abstract: Aliphatic or cyclic epoxides containing 3 to 8 carbon atoms which are present in aromatic hydrocarbons or halohydrocarbons are saponified continuously and directly to vicinal diols without the use of high temperatures and pressures which would otherwise be necessary. The saponification is acid catalyzed.Type: GrantFiled: November 15, 1985Date of Patent: December 2, 1986Assignee: Degussa AktiengesellschaftInventors: Rainer Siegmeier, Gunter Prescher, Helmut Maurer
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Patent number: 4620044Abstract: Hydrolysis of olefin oxides to their corresponding glycols was catalyzed by a steam stable zeolite, in its acid form, characterized by a constraint index within the range of about 1 to 12. Conversions of olefin oxide, in the presence of water, proceeded with minimal catalyst degradation. The acidity of the zeolite enabled the use of milder conditions than generally applied for this hydrolysis with no loss of desired selectivity. In addition, the described procedure offered the advantages typically associated with a heterogeneous catalyst (e.g., ease of separation, use of fixed bed reactor, etc.).Type: GrantFiled: October 16, 1985Date of Patent: October 28, 1986Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Stuart D. Hellring
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Patent number: 4617145Abstract: Described are the 1-methyl-2(2-methylbutyl) cyclohexanol derivatives defined according to the generic structure: ##STR1## wherein R represents hydrogen, MgCl, MgBr, lithium or acetyl; and uses of such 1-methyl-2(2-methylbutyl) cyclohexanol derivatives where R is hydrogen or acetyl for their organoleptic properties in augmenting or enhancing the aroma of perfume compositions, colognes or perfumed articles. Also described is the process for preparing such 1-methyl-2(2-methylbutyl) cyclohexanol derivatives including the reactions: ##STR2## wherein the latter reaction takes place using a methane sulfonic acid catalyst.Type: GrantFiled: November 21, 1985Date of Patent: October 14, 1986Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, Anubhav P. S. Narula, Marie R. Hanna
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Patent number: 4600800Abstract: An epoxide is isomerized in the liquid phase in the presence of a solid alumina catalyst and preferably an inert gaseous diluent, the isomerization conducted in the downflow mode.Type: GrantFiled: December 3, 1985Date of Patent: July 15, 1986Assignee: Shell Oil CompanyInventors: Robert H. Ellison, Peter S. Friend
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Patent number: 4579982Abstract: Alkylene oxides are hydrolyzed in a reaction menstruum containing an aqueous phase, a water-immiscible liquid phase, and a selectivity-enhancing, dissociatable metalate anion-containing material. The concentration of the metalate anion-containing material is greater in the water-immiscible liquid phase than that in the aqueous phase. The water-immiscible liquid phase can be separated from the aqueous phase to recover metalate anion-containing material.Type: GrantFiled: March 28, 1984Date of Patent: April 1, 1986Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: RE33307Abstract: Novel substituted cis-1,2-dihydroxy-cyclohexa-3,5-diene compounds, useful as intermediates in the production of phenols and catechols for use as intermediates in the production of drugs, herbicides, insecticides and as chiral synthons, in particular cis-1,2-dihydroxy-3-trifluoromethyl-cyclohexa-3,5-diene. A process for producing the novel compounds is also claimed.Type: GrantFiled: December 30, 1988Date of Patent: August 21, 1990Assignee: Imperial Chemical Industries PLCInventors: Stephen C. Taylor, Michael D. Turnbull