Polyhydroxy (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/811)
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Patent number: 5659069Abstract: This invention discloses an improved method for the [2+2+2] cyclotrimerization reaction in aqueous solutions using a water soluble transition metal catalyst.Type: GrantFiled: March 20, 1996Date of Patent: August 19, 1997Assignee: NeXstar Pharmaceuticals, Inc.Inventors: Bruce Eaton, Matthew S. Sigman
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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: 5478789Abstract: A hydrogenation reaction catalyst precursor of the present invention comprises a catalyst carrier (A) and a metal oxide composition (B) carried on or mixed with the catalyst carrier (A) at a weight ratio of (B)/(A)=15/85 to 65/35; the catalyst carrier (A) comprising a carrier base material of silica, etc. and a coating of titanium oxide and/or titanium hydroxide, the metal oxide composition (B) comprising copper oxide, zinc oxide, and at least one oxide of a metal selected from the group consisting of an element of group IIa of the periodic table, an element of group IIIb of the table, a lanthanide element, and an actinide element at a weight ratio of 100/(0 to 25)/(0 to 25). A hydrogenation reaction catalyst with a high catalytic activity and a high reaction selectivity is obtained by reduction of the hydrogenation reaction catalyst precursor.Type: GrantFiled: October 4, 1994Date of Patent: December 26, 1995Assignee: Kao CorporationInventors: Yasuyuki Hattori, Kiyoshi Tsukada
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Patent number: 5426206Abstract: Methods are provided for preparing all four diastereomers of 2-alkyl-3-hydroxyalkanals, 2-alkyl-3-silyloxyalkanals, and the like, with high enantiocontrol, using non-aldol chemistry. The synthetic methods also provide novel, stereospecific routes to polypropinates and chiral 2-substituted-1,3 diols.Type: GrantFiled: November 24, 1993Date of Patent: June 20, 1995Assignee: The Regents of the University of CaliforniaInventors: Michael E. Jung, Derin C. D'Amico
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Patent number: 5395985Abstract: A compound represented by the general formula (I) and a separating agent comprising the same: ##STR1## wherein Ar and Ar' are each an aromatic group; and the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para.The above compound is effective in the separation and purification of many compounds to and enables the provision of various compounds (such as intermediates of drugs) which are useful in the field of fine chemicals, particularly optically active substances, at high purities and in large amounts.Type: GrantFiled: March 4, 1994Date of Patent: March 7, 1995Assignee: Daicel Chemical Industries, Ltd.Inventor: Fumio Toda
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Patent number: 5395983Abstract: R or S-1-phenyl-1,3-propanediols having optical purity of 100% ee were obtained by recrystallization of R or S-1-phenyl-1,3-propanediols having optical purity of 20% ee to below 100% ee, the last diols are represented by the formula, ##STR1## It is possible to obtain optically pure 1-phenyl-3-propanediols from optically impure 1-phenyl-1,3-propanediols by a simple method.Type: GrantFiled: January 18, 1994Date of Patent: March 7, 1995Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Teruyo Sugiura, Yasuyuki Koizumi, Naoyuki Yoshida
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Patent number: 5395984Abstract: Described is a process for preparing 2-phenyl-1,3-propanediol by converting the 2-nitro-2-phenyl-1,3-propanediol to a nitro-dioxane of the formula ##STR1## wherein the groups R are both C.sub.1 -C.sub.6 alkyl or together comprise a C.sub.5 -C.sub.6 cycloalkyl group, or wherein one R group is H and the other is phenyl; hydrogenolysis of the nitro-dioxane to give a dioxane of the formula ##STR2## wherein R is as defined above; and hydrolyzing the dioxane to form 2-phenyl-1,3-propanediol.Type: GrantFiled: April 20, 1994Date of Patent: March 7, 1995Assignee: Schering CorporationInventors: Patrick O'Neill, Henry Doran
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Patent number: 5385942Abstract: A quinone derivative useful in the treatment of hepatic diseases defined by the general formula: ##STR1## where X and Y may be the same or different from each other and are each a hydroxyl group, a group represented by the formula --(--OCH.sub.2 --).sub.n --OR.sup.6, wherein n is 0 or 1 and R.sup.6 is a lower alkyl group, or an acyl group.Type: GrantFiled: March 1, 1993Date of Patent: January 31, 1995Assignee: Eisai Co., Ltd.Inventors: Shinya Abe, Yasushi Okamoto, Katsuya Tagami, Shigeki Hibi, Junichi Nagakawa, Kazuo Hirota, Ieharu Hishinuma, Kaname Miyamoto, Takashi Yamanaka, Hiromitsu Yokohama, Tsutomu Yoshimura, Tohru Horie, Yasunori Akita, Koichi Katayama, Isao Yamatsu
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Patent number: 5364993Abstract: Fullerenes are selectively functionalized by adsorbing fullerene molecules on molecular sieves such as zeolites as the first step in a desired functionalizing reaction and then adding functional groups or compounds to the fullerenes within the molecular sieves. An improved reactor for fullerene material is thereby available. Selectively functionalized fullerenes formed in accordance with the invention can also serve as precursors for further selectively functionalized products.Type: GrantFiled: January 21, 1993Date of Patent: November 15, 1994Assignee: Inrad, Inc.Inventors: Zhenyu Zhang, Warren Ruderman, James R. Fehlner
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Patent number: 5345005Abstract: In one embodiment, the invention relates to a catalyst in powdered form which comprises a major amount of the oxides of copper and zinc, and a minor amount of aluminum oxide wherein the pore volume of pores of said catalysts having a diameter between about 120 and about 1000 .ANG. is at least about 40% of the total pore volume. In another embodiment, the invention relates to a process for preparing hydrogenation catalysts comprising the oxides of copper, zinc and aluminum which comprises the steps of(A) preparing a first aqueous solution containing at least one water-soluble copper salt and at least one water-soluble zinc salt;(B) preparing a second solution containing at least one water-soluble basic aluminum salt and at least one alkaline precipitating agent;(C) mixing the first and second solutions whereby an insoluble solid is formed;(D) recovering the insoluble solid.Type: GrantFiled: September 18, 1992Date of Patent: September 6, 1994Assignee: Engelhard CorporationInventors: Deepak S. Thakur, Brian L. Roberts, Thomas J. Sullivan, Anita L. Vichek
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Patent number: 5342903Abstract: 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: GrantFiled: April 30, 1993Date of Patent: August 30, 1994Assignee: Ciba-Geigy CorporationInventors: Heinz Wolleb, Andreas Hafner, William M. Rolfe
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Patent number: 5334776Abstract: A compound represented by the general formula (I) and a separating agent comprising the same: ##STR1## wherein Ar and Ar' are each an aromatic group; and the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para.The above compound is effective in the separation and purification of many compounds and enables the provision of various compounds (such as intermediates of drugs) which are useful in the field of fine chemicals, particularly optically active substances, at high purities and in large amounts.Type: GrantFiled: March 12, 1993Date of Patent: August 2, 1994Assignee: Daicel Chemical Industries, Ltd.Inventor: Fumio Toda
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Patent number: 5306846Abstract: There are disclosed novel processes for the synthesis of novel intermediates useful in the of further synthesis of cyclitols and derivatives thereof.Type: GrantFiled: December 6, 1991Date of Patent: April 26, 1994Assignee: Virginia Tech Intellectual PropertiesInventor: Thomas Hudlicky
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Patent number: 5284982Abstract: The invention relates to a method of cyclooligomerization of 3-hydroxy-1-alkynes having 4-20 C atoms, particularly cyclooligomerization of 3-methyl-1-butyne-3-ol to yield 1,3,5-tris(.alpha.-hydroxyisopropyl)-benzene, with the aid of nickel-containing catalysts formed from a nickel compound, a phosphite of an ortho-substituted phenol, and an organoaluminum compound of formulaA1R.sub.(3-n) X.sub.s,whereR represents alkyl,X represents hydrogen or chlorine, andn=0 or 1,or an alkyllithium or alkylmagnesium compound, in the presence ofan aprotic diluent,(optionally) an unconjugated diene, and(optionally) a portion of the given 3-hydroxy-1-alkyne being oligomerized.Type: GrantFiled: February 4, 1993Date of Patent: February 8, 1994Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Wolfgang Schroder, Heinz-Werner Voges
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Patent number: 5260461Abstract: 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: GrantFiled: October 10, 1991Date of Patent: November 9, 1993Assignee: Massachusetts Institute of TechnologyInventors: Jens Hartung, K. Barry Sharpless
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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: 5250744Abstract: Process for the production of 2-aryl-1,3-propanediols and novel intermediate compounds produced thereby.Type: GrantFiled: November 17, 1992Date of Patent: October 5, 1993Assignee: Ganes Chemicals Inc.Inventors: Francis Johnson, Richard Miller
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Patent number: 5239121Abstract: Process for the production of 2-aryl-1,3-propanediols from a tropate ester and novel intermediate compounds produced thereby.Type: GrantFiled: September 16, 1992Date of Patent: August 24, 1993Assignee: Ganes Chemicals Inc.Inventors: Francis Johnson, Richard Miller
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Patent number: 5227537Abstract: A method is described for the production of 6,12-dihydro-6-hydroxy-cannabidiol which is obtained by the reaction of olivetol and cis-p-menth-2-ene-1,8,-diol and the reaction thereof to yield trans-delta-9-tetrahydrocannabinol.Type: GrantFiled: January 8, 1992Date of Patent: July 13, 1993Assignee: Heinrich Mack Nachf.Inventors: Peter Stoss, Peter Merrath
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Patent number: 5227543Abstract: 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: GrantFiled: October 10, 1991Date of Patent: July 13, 1993Assignee: Massachusetts Institute of TechnologyInventors: K. Barry Sharpless, Wihelm K. Amberg
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Patent number: 5118878Abstract: A gram-negative, aerobic, motile, rod-shaped bacterium which is closely related to Chryseomonas luteola and Flavimonas oryzihabitans, has been found to catalyze the biodegradation and biotransformation of bisphenol alkanes, such as 2,2-bis(4-hydroxyphenyl)-propane or bisphenol A. A variety of bisphenol alkyl alcohols can be made by this procedure.Type: GrantFiled: April 26, 1991Date of Patent: June 2, 1992Assignee: General Electric CompanyInventors: John H. Lobos, Terry K. Leib, Tah-Mun Su
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Patent number: 5116981Abstract: This invention encompasses novel analogs of Leukotriene B.sub.4 which are selected from a compound of formula I, B--C.apprxeq.C--CH.sub.2 C(M.sub.2)--C.apprxeq.C--Y--C(M.sub.1)--A, or formula II, B--C.apprxeq.C--CH.sub.2 C(M.sub.2)--C.apprxeq.C--P--R.sub.5 --A: wherein Y is: ##STR1## wherein P is: ##STR2## Patentable intermediates, process for making the novel analogs and intermediates and preparation of useful pharmacological agents comprising the analogs and intermediates are part of this invention.Type: GrantFiled: June 29, 1989Date of Patent: May 26, 1992Assignee: The Upjohn CompanyInventor: Joel Morris
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Patent number: 5072056Abstract: A novel method of preparing 2-phenyl substituted-1, 3-propanediols, useful intermediates in the synthesis of pharmaceutical preparations is disclosed.Type: GrantFiled: September 26, 1989Date of Patent: December 10, 1991Assignee: Carter-Wallace, Inc.Inventor: Frank J. Stiefel
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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: 5053562Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium, a phosphine, and a lower-alkyl iodide or .beta.-hydroxy lower-alkyl iodide.Type: GrantFiled: July 31, 1990Date of Patent: October 1, 1991Assignee: Hoechst Celanese CorporationInventor: Kwoliang D. Tau
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Patent number: 5030771Abstract: A method of producing aliphatic and cycloaliphatic diols by catalytic hydrogenation of dicarboxylic acid esters by the use of a copper chromite catalyst in which the copper content (calculated as CuO) is 40-47 wt. %, and the chromium content (calculated as Cr.sub.2 O.sub.3) is 40-47 wt. %, and barium is also present in the amount of up to 10 wt. % (calculated as BaO) under mild temperature and pressure conditions is disclosed. The method produces diols without the formation of high boiling materials and does not require purification of the product diols by overhead distillation.Type: GrantFiled: December 20, 1989Date of Patent: July 9, 1991Assignee: Huels AktiengesellschaftInventors: Werner Fuhrmann, Gunther Bub, Manfred zur Hausen
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Patent number: 5019656Abstract: A process for preparing p-hydroxybenzyl alcohol or a derivative thereof comprising reacting a phenol and a formaldehyde source under a basic condition is disclosed, wherein the reaction is carried out in an alcoholic organic solvent in the presence of a crown ether. The process achieves high selectivity toward the para position without involving high cost.Type: GrantFiled: February 27, 1990Date of Patent: May 28, 1991Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Hiroshi Iwane, Takahiro Sugawara, Naoki Suzuki
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Patent number: 5003115Abstract: A method for producing 4-hydroxyphenethyl alcohol by epoxidizing 4-acetoxystyrene with a percaboxylic acid to produce 4-acetoxyphenyl oxirane; and catalytically hydrogenating the 4-acetoxyphenyl oxirane with hydrogen to produce 4-acetoxyphenethyl alcohol; and saponifying or transesterifying the 4-acetoxyphenethyl alcohol to produce 4-hydroxyphenethyl alcohol.Type: GrantFiled: March 28, 1990Date of Patent: March 26, 1991Assignee: Hoechst Celanese CorporationInventor: Heinz Strutz
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Patent number: 4990693Abstract: Novel physiologically active substances KS-504a, KS-504b and KS-504d having a vasodilative activity and a novel physiologically active substance KS-504e having an activity to inhibit histamine secretion are produced by culturing a microorganism of the genus Mollisia.Type: GrantFiled: January 16, 1990Date of Patent: February 5, 1991Assignee: Kyowa Hakko Kogyo Co. Ltd.Inventors: Satoshi Nakanishi, Koji Yamada, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Noriaki Hirayama, Hiroshi Kase, Joji Goto, Etsuyo Shimizu
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Patent number: 4990690Abstract: An industrially meritorious process for preparing aromatic polyhydric alcohol is disclosed. The process can give an extremely high conversion rate of raw material, i.e., aromatic carboxylic acid ester, and an extremely high selectivity to the objective compound. The process comprises catalytic hydrocracking of an aromatic carboxylic acid ester in which an improvement resides in the fact that an ester represented by the general formula Ar(COOR).sub.m, (CH.sub.2 OH).sub.n, (wherein Ar means an aromatic group, R is independently selected from normal and branched alkyl groups having at least 6 carbon atoms, m' means an integer of at least 1, n' means zero or a positive integer and m'+n' satisifies the relationship m'+n'.gtoreq.2) is used as raw material. An aromatic polyhydric alcohol is a very useful material, especially as a raw material for the preparation of polymeric substances having high heat resistance.Type: GrantFiled: May 11, 1989Date of Patent: February 5, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yuji Onda, Fumisada Kosuge, Masaru Tunoda
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Patent number: 4990689Abstract: By reacting fluorobenzene with hexafluoroacetone in the pressure of a Lewis acid catalyst, e.g. aluminum chloride, a novel compound 2,4-bis(2-hydroxyhexafluoro-2-propyl)fluorobenzene is formed at high yield with little formation of isomers. The novel compound is useful as a cross-linking agent for some polymers and also as a material of some polymers.Type: GrantFiled: June 20, 1989Date of Patent: February 5, 1991Assignee: Central Glass Company, LimitedInventors: Masamichi Maruta, Takayuki Nishimiya
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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: 4982016Abstract: Synthesis of 2-phenyl-1,3-propanediol by the selective reduction of diethyl phenylmalonate with metal hydrides in solution with heterocyclic ethers are disclosed.Type: GrantFiled: June 6, 1989Date of Patent: January 1, 1991Assignee: Carter-Wallace, Inc.Inventor: Young M. Choi
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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: 4965364Abstract: An osmium-catalyzed method of addition to an olefin. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an amine oxide an osmium-containing compound and, optionally a tetraalkyl ammonium compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, an amine 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 or an amine derivative and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, N-methyl morpholine N-oxide and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.Type: GrantFiled: September 28, 1988Date of Patent: October 23, 1990Assignee: Massachusetts Institute of TechnologyInventors: Istvan E. Marko, K. Barry Sharpless
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Patent number: 4959488Abstract: Polyfunctional hexasubstituted benzene derivatives wherein at least three of the substituents are saturated carbon chains having from 1 to 21 carbon atoms and functional groups containing hetero functionalities at the ends of the carbon chains and the remainder of the 6 substituents are either saturated carbon chains containing from 1 to 21 carbon atoms or saturated carbon chains containing from 1 to 21 carbon atoms having a functional group including a hetero functional group containing N, O, S, P, or Si at the end of the chains. These derivatives are made by reacting a disubstituted alkyne wherein one or both of the substituents are saturated carbon chains having 1 to 21 carbon atoms to which hetero functional groups are attached with a palladium catalyst and isolating the resulting hexasubstituted benzene derivative.Type: GrantFiled: May 17, 1989Date of Patent: September 25, 1990Assignee: Henkel Research CorporationInventors: James M. Renga, Alan G. Olivero, Mark Bosse
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Patent number: 4954659Abstract: A grignard synthesis of pharmacologically active 1,4-bis(dihydroxyphenyl)butane and analogs, as well as novel intermediates, is provided, comprising preparing a grignard reagent preferably, a 3,4-dialkoxyphenyl propyl magnesium bromide, which may be reacted with carbonyl compounds to form intermediates of desired end products, said carbonyl compounds preferably being 3,4-dialkoxybenzaldehydes. The resulting alcohol is converted to a corresponding ether or siloxy compound, at the carbonyl site. The oxy-substituent is cleaved off; and the benzene ring or rings dealkylated to leave hydroxy substituents on the rings.Type: GrantFiled: August 19, 1988Date of Patent: September 4, 1990Assignee: Chemex Pharmaceuticals, Inc.Inventors: Robert M. Parkhurst, Ronald S. Pardini
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Patent number: 4935560Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.Type: GrantFiled: January 16, 1990Date of Patent: June 19, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
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Patent number: 4935554Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium and a phosphine.Type: GrantFiled: July 17, 1989Date of Patent: June 19, 1990Assignee: Hoechst Celanese CorporationInventors: Mark A. Murphy, Brad L. Smith, Adolfo' Aguilo', Kwoliang D. Tau
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Patent number: 4918248Abstract: An alcohol is effective produced by catalytically reducing an organic carboxylic acid ester with hydrogen in the presence of a catalyst obtained by reducing a catalyst precursor comprising (A) copper oxide and (B) titanium oxide and/or titanium hydroxide at a weight ratio of (A) to (B) in the range between 15/85 and 65/35. The component (A) may be alternatively a composite metal oxide comprises copper oxide and up to 20 wt. % of zinc oxide.Type: GrantFiled: May 22, 1989Date of Patent: April 17, 1990Assignee: Kao CorporationInventors: Yasuyuki Hattori, Noriaki Fukuoka, Shigeru Tamura, Kunizo Hashiba, Kiyoshi Tsukada, Makoto Misono
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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: 4873378Abstract: A process for manufacturing 1,3-glycols is disclosed. The process comprises reacting an epoxide with synthesis gas in the presence of rhodium and a phosphine.Type: GrantFiled: December 15, 1987Date of Patent: October 10, 1989Assignee: Hoechst Celanese CorporationInventors: Mark A. Murphy, Brad L. Smith, Adolfo Aguilo', Kwoliang D. Tau
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Patent number: 4873375Abstract: A process for preparing a fluorine-substituted alicyclic diol comprising hydrogenating in the presence of a catalyst a fluorine-substituted aromatic diol represented by formula (I): ##STR1## wherein Ph represents a divalent organic group containing at least one aromatic group, to obtain the fluorine-substituted alicyclic diol represented by formula (II): ##STR2## wherein Ph(H) represents a divalent organic group containing at least one perhydroaromatic group.Type: GrantFiled: April 11, 1988Date of Patent: October 10, 1989Assignee: Daikin Industries, Ltd.Inventors: Motonobu Kubo, Yoshiki Shimizu
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Patent number: 4868327Abstract: A novel method for preparing 2-phenyl-1, 3-propanediol and its dicarbamate is disclosed which readily lends itself to commercial production.Type: GrantFiled: June 3, 1987Date of Patent: September 19, 1989Assignee: Carter-Wallace, Inc.Inventor: Frank J. Stiefel
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Patent number: 4822924Abstract: A process for producing 2,6-dichlorobenzyl alcohol, which comprises reacting 2,6-dichlorobenzyl chloride with an acetate-forming agent to form its acetate, followed by hydrolysis to obtain 2,6-dichlorobenzyl alcohol, wherein anhydrous sodium acetate is used as the acetate-forming agent, and a quaternary ammonium salt is added as a phase transfer catalyst during the acetate-forming reaction.Type: GrantFiled: December 23, 1987Date of Patent: April 18, 1989Assignee: Hodogaya Chemical Co., Ltd.Inventors: Ichiro Otsu, Sueo Kanno, Sinichi Sato, Tetsuya Kondo
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Patent number: 4822925Abstract: Novel vicinal dioxyalkylene organometalates comprising a cation having a hydrocarbyl-containing substituent are disclosed. The vicinal dioxyalkylene organometalates can be reacted with water to yield alkylene glycols.Type: GrantFiled: February 6, 1987Date of Patent: April 18, 1989Assignee: Union Carbide CorporationInventors: John R. Briggs, John H. Robson
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Patent number: 4778568Abstract: Isomer mixtures of 1,3- and 1,4-bis-(2-hydroxyhexafluoroprop-2-yl)-benzene are separated by a steam distillation in the presence of CS.sub.2. On cooling of the steam distillate, a solid precipitates which is composed mainly of the 1,4-isomer. After the solid has been separated off, an aqueous-organic liquid-phase mixture remains, the organic phase of which mainly contains the 1,3-isomer. The pure isomers are obtained by recrystallization or distillation respectively. These are mainly intermediates in the polymer field.Type: GrantFiled: July 21, 1987Date of Patent: October 18, 1988Assignee: Hoechst AktiengesellschaftInventors: Klaus-Albert Schneider, Gunter Siegemund
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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: 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: 4675421Abstract: Compound of the general formula ##STR1## wherein R represents an ether protecting group useful as intermediates.Type: GrantFiled: August 23, 1985Date of Patent: June 23, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josef Hubscher