One Double Bond Between Ring Members Of The Hetero Ring Patents (Class 549/507)
  • Patent number: 9701601
    Abstract: The present invention relates to an optically active axially chiral ?-allenic alcohol, a synthesis method and use thereof. The invention relates to a method of preparing a highly optically active chiral ?-allenic alcohol by using propargyl alcohol, aldehyde and chiral ?,?-diphenyl-L-prolinol under the protection of tert-butyldimethylsilyl with an accelerant zinc bromide. The axially chiral ?-allenic alcohol has the structural formula (I). The method of the present invention has the following advantages: the synthesis route is short, operations are simple, raw materials are readily available, separation and purification are convenient, the substrate has high universality, the total yield is high, and enantioselectivity and diastereoselectivity are high.
    Type: Grant
    Filed: November 20, 2012
    Date of Patent: July 11, 2017
    Assignee: SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES
    Inventors: Shengming Ma, Juntao Ye
  • Publication number: 20150126744
    Abstract: This disclosure relates to new metal complexes, such as compounds of Formula 1, and their application in olefin or alkyne metathesis and to methods of carrying out olefin metathesis reactions.
    Type: Application
    Filed: December 12, 2014
    Publication date: May 7, 2015
    Inventors: Krzysztof Skowerski, Michal Bieniek
  • Publication number: 20150105567
    Abstract: The present invention relates to an optically active axially chiral ?-allenic alcohol, a synthetic method and use thereof. A method of preparing a high optically active chiral ?-allenic alcohol by using propargyl alcohol, aldehyde and chiral ?,?-diphenyl-L-prolinol under the protection of tert-butyldimethylsilyl with a mediator zinc bromide. The axially chiral ?-allenic alcohol has the structural formula (I). The method of the present invention has the following advantages: the synthesis route is short, operations are simple, raw materials are readily available, separation and purification are convenient, the substrate has high generality, the total yield is high, and enantioselectivity and diastereoselectivity are high.
    Type: Application
    Filed: November 20, 2012
    Publication date: April 16, 2015
    Applicant: SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY, CHINESE ACADEMY OF SCIENCES
    Inventors: Shenming Ma, Juntao Ye
  • Publication number: 20140228563
    Abstract: Cis and trans ruthenium complexes that can be used as catalysts for ring opening metathesis polymerisation (ROMP) are described. The complexes are generally square pyramidal in nature, having two anionic ligands X. Corresponding cationic complexes where one or both of the anionic ligands X are replaced by a non-co-ordinating anionic ligand are also described. Polymers such as polydicyclopentadiene (PDCPD) can be prepared using the catalysts.
    Type: Application
    Filed: September 28, 2012
    Publication date: August 14, 2014
    Applicant: University Court of the University of St. Andrews
    Inventor: Catherine Cazin
  • Publication number: 20140171607
    Abstract: The present invention provides new ruthenium complexes of Formula (1), which contain a chelate ring created by a halogen atom X. The invention concerns also a method for the preparation of the new ruthenium complexes and their application in metathesis reactions.
    Type: Application
    Filed: June 4, 2012
    Publication date: June 19, 2014
    Applicant: UMICORE AG & CO. KG
    Inventors: Karol Grela, Michal Barbasiewicz, Michal Michalak
  • Publication number: 20140005408
    Abstract: This disclosure relates to new metal complexes, such as compounds of Formula 1, and their application in olefin or alkyne metathesis and to methods of carrying out olefin metathesis reactions.
    Type: Application
    Filed: June 18, 2013
    Publication date: January 2, 2014
    Applicant: APEIRON SYNTHESIS S.A.
    Inventors: Krzysztof Skowerski, Michal Bieniek
  • Publication number: 20130165649
    Abstract: Cls ruthenium complexes that can be used as catalysts are described. The complexes are generally square pyramidal in nature, having two anionic ligands X adjacent to each other. The complexes can be used as catalysts, for example in olefin metathesis reactions. Corresponding trans ruthenium complexes are also described, together with cationic complexes where one or both of the anionic ligands X are replaced by a non-co-ordinating anionic ligand.
    Type: Application
    Filed: March 21, 2011
    Publication date: June 27, 2013
    Inventor: Catherine Cazin
  • Publication number: 20130116424
    Abstract: A method for utilizing biomass components, namely cellulose, hemicellose, and lignin, and converting them to value-added biobased chemical products is described herein. The present method provides treatments to obtain a plurality of component streams from biomass for producing derivative products while minimizing waste products.
    Type: Application
    Filed: November 9, 2011
    Publication date: May 9, 2013
    Applicant: Thesis Chemistry, LLC
    Inventors: John R. Peterson, Christopher M. Yost, Jian Wu
  • Patent number: 8410293
    Abstract: The present invention relates to a process for the preparation of cyclic enol ethers.
    Type: Grant
    Filed: June 28, 2012
    Date of Patent: April 2, 2013
    Assignee: BASF SE
    Inventors: Klaus Ebel, Bernhard Brunner, Christoph Stock, Ralf Pelzer
  • Publication number: 20130079515
    Abstract: The present invention provides ruthenium complexes of the formula wherein: X and X? denote an anionic ligand selected independently from the group consisting of anions of halogens, the phenolate anion (C6H5O?) the perfluorophenolate anion (C6F5O?), and residues of arylcarboxylic, alkylcarboxylic, perfluoroalkylcarboxylic, alkylsulphonic, arylsulphonic, or perfluoroalkylsulphonic acids; A denotes either nitrogen or carbon with an R5 group; R1 denotes hydrogen, C1-C5 alkyl, C2-C5 alkene or C3-C7 cycloalkyl; and R2, R3, R4, R5, R6, R7 denote independently hydrogen, C1-C25 alkyl, C1-C25 perfluoroalkyl, C5-C24 aryl, C2-C25 alkene, C3-C7 cycloalkyl, nitro (—NO2), cyano (—CN), formyl (—CHO), carboxyl (—COOH), or an ester (—COOR?), sulphone (—SO2R?), sulphonamide (—SO2NR?2), or ketone (—COR?) group, in which R? is a C1-C5 alkyl, C1-C5 perfluoroalkyl, or C5-C24 aryl group.
    Type: Application
    Filed: August 10, 2012
    Publication date: March 28, 2013
    Applicant: UMICORE AG & CO. KG
    Inventors: Karol GRELA, Michal BARBASIEWICZ, Anna SZADKOWSKA
  • Patent number: 8404872
    Abstract: Vinyl oxiranes are rearranged to 2,5-dihydrofuran using catalyst (III) or (IV). The 2,5-dihydrofuran can be reduced to tetrahydrofuran. 3,4-Epoxy-1-butene substrate is converted to 2,5-dihydrofuran which in turn is converted to tetrahydrofuran. Substrate for making 3-methyltetrahydrofuran is prepared from isoprene. Substrate for making 2-methyltetrahydrofuran is prepared from piperylene. Reactions analogous to that with vinyl oxiranes are carried out with vinyl thiiranes and vinyl aziridines.
    Type: Grant
    Filed: March 12, 2007
    Date of Patent: March 26, 2013
    Assignee: Cornell University
    Inventors: Jon Njardarson, Lindsay Batory, Matthew Brichacek, Renato Bauer, Erik Rogers
  • Patent number: 8394934
    Abstract: A method is disclosed for synthesizing 2?,3?-didehydro-2?,3?-dideoxynucleosides (d4Ns) from a nucleophile-mediated elimination, such as a telluride-mediated elimination reaction. After substitution of 2,2?-anhydronucleosides with a nucleophile, such as a telluride monoanion, a telluride intermediate is formed, and its elimination leads to formation of the olefin products (d4Ns). This disclosure describes this telluride-assisted (or nucleophile-assisted) reaction and how to facilitate the substitution and elimination in order to form d4Ns.
    Type: Grant
    Filed: March 20, 2009
    Date of Patent: March 12, 2013
    Inventors: Zhen Huang, Jia Sheng
  • Patent number: 8344023
    Abstract: Di-/trisubstituted furans of the formula (I) and their use as odorants wherein R1 is hydrogen or methyl; R2 is ethyl, propyl or isopropyl; the bond between C-3 and C-4 is a single bond, or the dotted line together with the bond between C-3 and C-4 represents a double bond; and the bond between C-4? and C-5? is a single bond, or the dotted line together with the bond between C-4? and C-5? represents a double bond, either in (E)- or (Z)-configuration. The invention furthermore relates to a method of their production and to perfume compositions comprising them.
    Type: Grant
    Filed: June 3, 2008
    Date of Patent: January 1, 2013
    Assignee: Givaudan SA
    Inventor: Philip Kraft
  • Publication number: 20120123133
    Abstract: The invention relates to ruthenium alkylidene complexes having an N-heterocyclic carbene ligand comprising a 5-membered heterocyclic ring having a carbenic carbon atom and at least one nitrogen atom contained within the 5-membered heterocyclic ring, wherein the nitrogen atom is directly attached to the carbenic carbon atom and is substituted by a phenyl ring, and wherein the phenyl ring has a hydrogen at either or both ortho positions and is substituted at at least one ortho or meta position. The invention also relates to an olefin metathesis reactions and particularly to the preparation of tetra-substituted cyclic olefins via a ring-closing metathesis.
    Type: Application
    Filed: August 30, 2011
    Publication date: May 17, 2012
    Applicants: CALIFORNIA INSTITUTE OF TECHNOLOGY, MATERIA, INC.
    Inventors: Jacob BERLIN, Robert H. GRUBBS, Yann SCHRODI, Ian C. STEWART
  • Patent number: 8039645
    Abstract: The method of the invention for continuously producing 2,5-dihydrofuran includes subjecting cis-2-butene-1,4-diol to liquid-phase dehydration-cyclization reaction in the presence of alumina, characterized in that the sum of the concentration of carbonyl compounds present in the reaction system and the concentration of acetal compounds present in the reaction system is controlled to fall within a range of 0.1 to 2 mol/L, provided that the concentration of the acetal compounds is calculated in terms of acetal groups, the concentrations being determined on the basis of the total amount of the reaction mixture. According to the method, 2,5-dihydrofuran, which is useful as a raw material or intermediate for producing pharmaceuticals, agrochemicals, raw materials of polymers, etc., can be continuously produced. The method can prevent inactivation of ?-alumina and is advantageous for long-term production on an industrial scale.
    Type: Grant
    Filed: March 5, 2008
    Date of Patent: October 18, 2011
    Assignee: Kuraray Co., Ltd.
    Inventors: Junichi Fuji, Shigeru Okano, Katsushi Nagareda
  • Publication number: 20110190516
    Abstract: The invention provides a method for producing a vinyl ether compound, characterized in that the method includes isomerizing an allyl ether compound represented by formula (I) or (II): (wherein R1 represents a C1 to C6 alkyl group; each of R2, R3, and R4 independently represents a hydrogen atom, a C1 to C6 alkyl group, or a C3 to C6 alkenyl group; and n is 1 or 2) in the presence of hydrogen, a monodentate tris(ortho-substituted aryl) phosphite, and a rhodium compound. The vinyl ether compound is useful as a raw material, an intermediate, etc. for producing pharmaceuticals, agrochemicals, polymers, etc.
    Type: Application
    Filed: May 1, 2009
    Publication date: August 4, 2011
    Applicant: Kuraray Co., Ltd.
    Inventor: Junichi Fuji
  • Publication number: 20100274030
    Abstract: A process of preparing cyclic ethers is described. The process involves the reaction of at least one organic compound such as a dioi or a polyol which it has at least one pair of hydroxyl groups separated by 4 or 5 carbon atoms, and which is capable of being converted into an ether linkage, with an organic carbonate in the presence of a base. The base is an alkoxy, a carbonate or a hydroxide base or is a mixture of such bases. At least one of the hydroxyl groups of the organic compound is not a tertiary hydroxyl group.
    Type: Application
    Filed: July 14, 2008
    Publication date: October 28, 2010
    Inventors: Hanamanthsa Shankarsa Bevinakatti, Christopher Paul Newman, Simon Ellwood, Pietro Tundo, Fabio Arico, Martin Schroeder
  • Patent number: 7632790
    Abstract: 2,2-Disubstituted 5-methyl-2,5-dihydro- and 2,2-disubstituted 5-methyl-tetrahydrofurans of formula (I) wherein R1 is methyl, ethyl, propyl or iso-propyl; and R2 is a branched C4-C7 alkyl, C5-C8 cycloalkyl, or mono- or disubstituted C5 or C6 cycloalkyl; and the bond between C-3 and C-4 is a single bond, or the dotted line together with the bond between C-3 and C-4 represents a double bond are useful as odorants.
    Type: Grant
    Filed: March 7, 2005
    Date of Patent: December 15, 2009
    Assignee: Givaudan S.A.
    Inventor: Philip Kraft
  • Publication number: 20090131691
    Abstract: Vinyl oxiranes are rearranged to 2,5-dihydrofuran using catalyst (III) or (IV). The 2,5-dihydrofuran can be reduced to tetrahydrofuran. 3,4-Epoxy-1-butene substrate is converted to 2,5-dihydrofuran which in turn is converted to tetrahydrofuran. Substrate for making 3-methyltetrahydrofuran is prepared from isoprene. Substrate for making 2-methyltetrahydrofuran is prepared from piperylene. Reactions analogous to that with vinyl oxiranes are carried out with vinyl thiiranes and vinyl aziridines.
    Type: Application
    Filed: March 12, 2007
    Publication date: May 21, 2009
    Applicant: CORNELL RESEARCH FOUNDATION INC.
    Inventors: Jon Njardarson, Lindsay Batory, Matthew Bricachek, Renato Bauer, Erik Rogers
  • Publication number: 20090017330
    Abstract: A material for organic electroluminescence devices of the invention which is for use in combination with at least one phosphorescent metal complex has a specific heterocyclic structure. The material for organic electroluminescence devices is used as a host material or a hole transporting material. An organic electroluminescence device having an anode, a cathode and an organic thin film layer having one or more layers which is interposed between the anode and cathode, in which at least one layer of the organic thin film layer contains the material for organic electroluminescence devices, has a high emitting efficiency, causes little pixel defects, is excellent in heat resistance, and shows a long lifetime.
    Type: Application
    Filed: November 21, 2007
    Publication date: January 15, 2009
    Applicant: IDEMITSU KOSAN CO., LTD.
    Inventors: Toshihiro Iwakuma, Jun Endo, Masaki Numata, Kenichi Fukuoka
  • Publication number: 20080275247
    Abstract: The present invention relates to novel transition metal complexes of the formula (I) to a process for preparing these transition metal complexes and to the use of the transition metal complexes as catalysts in metathesis reactions.
    Type: Application
    Filed: April 24, 2008
    Publication date: November 6, 2008
    Inventors: Renat Kadyrov, Anna Szadkowska, Karol Grela, Michal Barbasiewicz
  • Patent number: 7135582
    Abstract: A transition metal complex having 2,2?-bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-1,1?-binaphthyl as a ligand. The presence of the transition metal complex in the reaction system of an asymmetric reaction system allows the preparation of an objective compound having an objective absolute configuration with improved efficiency.
    Type: Grant
    Filed: December 4, 2003
    Date of Patent: November 14, 2006
    Assignee: Takeda Pharmaceutiacal Company Limited
    Inventors: Mitsutaka Goto, Mitsuhisa Yamano, Shinji Kawaguchi
  • Patent number: 7128983
    Abstract: A furan-containing compound of formula (I): Ar is aryl, heteroaryl, or oligoaryl; A is furyl; B is aryl or heteroaryl; R1 is hydrogen, alkenyl, alkynyl, aryl, heteroaryl, cyclyl, heterocyclyl, or oligoaryl; and R2 is hydrogen, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cyclyl, or heterocyclyl. The compound is useful as a hole transporting material in an organic light emitting diode device.
    Type: Grant
    Filed: August 18, 2003
    Date of Patent: October 31, 2006
    Assignee: Academia Sinica
    Inventors: Tien-yau Luh, Lingzhi Zhang, Chin-Fa Lee, Chung-Chih Wu, Cheih-Wei Chen
  • Patent number: 7091051
    Abstract: A chemiluminescence method characterized in that when a 1,2-dioxetane derivative of the formula 1: wherein each of R1, R2, R3, R4 and R5 which are independent of one another, is a hydrogen atom, an alkyl group or an aryl group, or each pair of R2 and R3, and R4 and R5, which are independent of each other, may form together a cyclic alkyl group, R6 is a hydroxyl group, an alkoxyl group, an aralkyloxy group, a group represented by —OSi(R8R9R10) (provided that each of R8, R9 and R10 which are independent of one another, is an alkyl group or an aryl group), a phosphate group or a group represented by S(C?O)R11 (provided that R11 is an alkyl group or an aryl group), and R7 is a hydrogen atom, a halogen atom, an alkyl group or an alkoxyl group, is let generate chemiluminescence by means of an activator selected from the group consisting of a base, an acid, a salt, a fluorine compound, an enzyme, a catalyst and an amine compound, a cationic surfactant and a fluorescent material are made to coexist.
    Type: Grant
    Filed: August 25, 2004
    Date of Patent: August 15, 2006
    Assignee: Tosoh Corporation
    Inventors: Kenji Kitaoka, Masashi Yamada, Seiji Kawaguchi
  • Patent number: 7078542
    Abstract: Nonlinear optically active compounds, methods for making nonlinear optically active compounds, compounds useful for making nonlinear optically active compounds, methods for making compounds useful for making nonlinear optically active compounds, macrostructures that include nonlinear optically active components, and devices including the nonlinear optically active compounds and the macrostructures.
    Type: Grant
    Filed: September 3, 2004
    Date of Patent: July 18, 2006
    Assignee: University of Washington
    Inventors: Kwan-Yue Jen, Hong Ma, Sen Liu, Larry R Dalton
  • Patent number: 7019155
    Abstract: Disclosed is a method for the hydrogenation of tetrahydroxybutane in the presence of supported rhenium catalysts and an acid to form tetrahydrofuran and its precursors.
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: March 28, 2006
    Assignee: Invista North America S.A.R.L.
    Inventor: Leo Ernest Manzer
  • Publication number: 20040131883
    Abstract: A furan-containing compound of formula (I): 1
    Type: Application
    Filed: August 18, 2003
    Publication date: July 8, 2004
    Inventors: Tien-yau Luh, Lingzhi Zhang, Chin-Fa Lee, Chung-Chih Wu, Chieh-Wei Chen
  • Patent number: 6730800
    Abstract: Unsubstituted or alkyl-substituted THF is obtained by catalytic hydrogenation in the gas phase of C4-dicarboxylic acids and/or their derivatives using a catalyst comprising <80% by weight, preferably <70% by weight, in particular from 10 to 65% by weight, of CuO and >20% by weight, preferably >30% by weight, in particular from 35 to 90% by weight, of an oxidic support having acid centers, at a hot spot temperature of from 240 to 310° C., preferably from 240 to 280° C., and a WHSV over the catalyst of from 0.01 to 1.0, preferably from 0.02 to 1, in particular from 0.05 to 0.5, kg of starting material/l of catalyst x hour.
    Type: Grant
    Filed: June 4, 2003
    Date of Patent: May 4, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf-Hartmuth Fischer, Frank Stein, Rolf Pinkos, Michael Hesse, Michael Jolyon Sprague, Markus Rösch, Holger Borchert, Stephan Schlitter, Ralf-Thomas Rahn, Alexander Weck
  • Patent number: 6593481
    Abstract: Disclosed is a method whereby 3,4-tetrahydrofurandiol is hydrogenated in the presence of Rh, Re, Pd, Ru and Ni catalysts, optionally supported, to form tetrahydrofuran and its precursors.
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: July 15, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Publication number: 20020132365
    Abstract: A 1,2-dioxetane derivative of the formula (I): 1
    Type: Application
    Filed: March 7, 2002
    Publication date: September 19, 2002
    Applicant: TOSOH CORPORATION
    Inventors: Masakatsu Matsumoto, Nobuko Watanabe, Masashi Yamada
  • Patent number: 6395912
    Abstract: Disclosed are processes for the isomerization of epoxyalkenes to dihydrofurans by contacting an epoxyalkene with a catalyst comprising a quaternary organic onium iodide compounds, optionally deposited on a non-acidic support and/or in combination with a Lewis acid co-catalyst The catalyst may comprise a supported catalyst, an unsupported catalyst or a solution of the catalytically-active components in an inert, organic solvent.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: May 28, 2002
    Assignee: Eastman Chemical Company
    Inventor: Stephen Neal Falling
  • Patent number: 6353121
    Abstract: Disclosed is a process for separating 2,5-dihydrofuran (2,5-DHF) from aqueous solution of 2,5-DHF by extractive distillation using certain organic liquids as the extraction agent.
    Type: Grant
    Filed: February 22, 2001
    Date of Patent: March 5, 2002
    Assignee: Eastman Chemical Company
    Inventor: Scott Donald Barnicki
  • Patent number: 6346652
    Abstract: A composition and method for the catalytic conversion of a racemic mixture of dienes to a cyclic olefin by a ring-closing metathesis (RCM) reaction are disclosed. The composition, a transition metal complex with an M═C reaction site, contains a bidentate dialkoxide of at least 80% optical purity. Because the M═C reaction site is of a sufficient shape specificity, conferred in part by the dialkoxide of sufficient rigidity and a M═N—R1 site, reacting the composition with a mixture of two enantiomeric dienes results in an olefin metathesis product that has at least a 50% enantiomeric excess of one enantiomer in the mixture. A method is also provided for reacting a composition with a racemic diene mixture to generate a metathesis product that has an enantiomeric excess of at least 50%. Methods are also provided for catalytic enantioselective desymmetrization.
    Type: Grant
    Filed: July 13, 1998
    Date of Patent: February 12, 2002
    Assignee: Massachusetts Institute of Technology
    Inventors: Richard R. Schrock, Amir H. Hoveyda
  • Patent number: 6342614
    Abstract: Disclosed are processes for the isomerization of epoxyalkenes to dihydrofurans by contacting an epoxyalkene with a catalyst comprising a quaternary organic onium iodide compounds, optionally deposited on a non-acidic support and/or in combination with a Lewis acid co-catalyst. The catalyst may comprise a supported catalyst, an unsupported catalyst or a solution of the catalytically-active components in an inert, organic solvent.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: January 29, 2002
    Assignee: Eastman Chemical Company
    Inventor: Stephen Neal Falling
  • Patent number: 6335455
    Abstract: This invention pertains to a process for the preparation of 2,5-dihydrofurans by the isomerization of &ggr;,&dgr;-epoxyalkenes in the presence of a catalyst system comprising an organotin compound and an alkali metal iodide.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: January 1, 2002
    Assignee: Eastman Chemical Company
    Inventors: Shaowo Liang, Yao-Ching Liu
  • Patent number: 6201139
    Abstract: Disclosed are processes for the isomerization of epoxyalkenes to dihydrofurans by contacting an epoxyalkene with a catalyst comprising a quaternary organic onium iodide compounds, optionally deposited on a non-acidic support and/or in combination with a Lewis acid co-catalyst. The catalyst may comprise a supported catalyst, an unsupported catalyst or a solution of the catalytically-active components in an inert, organic solvent.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 13, 2001
    Assignee: Eastman Chemical Company
    Inventors: Stephen Neal Falling, Patricia Lopez-Maldonado
  • Patent number: 6201138
    Abstract: Disclosed are processes for the isoberization of epoxyalkenes to dihydrofurans by contacting an epovyalkene with a catalyst comprising a quaternary organic onium iodide compounds, optionally deposited on a non-acidic support and/or in combination with a Lewis acid co-catalyst. The catalyst may comprise a supported catalyst, an unsupported catalyst or a solution of the catalytically-active components in an inert, organic solvent.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 13, 2001
    Assignee: Eastman Chemical Company
    Inventors: John Robert Monnier, Stephen Neal Falling, Patricia Lopez-Maldonado
  • Patent number: 6096673
    Abstract: An improved process is provided for the recovery of catalyst components from oligomeric impurities which are formed during the industrial preparation of 2,5-dihydrofuran by the catalytic isomerization of vinyl oxirane followed by an essential separation of the oligomeric by-products which otherwise cause deactivation of the catalyst. The catalyst components consist essentially of (a) an onium iodide and (b) a Lewis acid selected from the group consisting of the chloride, bromide or iodide of the metals zinc, tin, cobalt and bismuth, preferably zinc, where the catalyst optionally includes a donor ligand.
    Type: Grant
    Filed: April 21, 1998
    Date of Patent: August 1, 2000
    Assignee: BASF Aktiengesellschaft
    Inventor: Martin Fischer
  • Patent number: 6066746
    Abstract: Process for producing coatings or moldings by radiation curing, which involves using high-energy light to irradiate radiation-curable compositions containing 1-100% by weight, based on the total amount of free-radically or cationically polymerizable compounds, of compounds A) containing at least one cationically polymerizable 2,3-dihydrofuran group.
    Type: Grant
    Filed: March 12, 1999
    Date of Patent: May 23, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reich, Reinhold Schwalm, Erich Beck, Lukas Haussling, Oskar Nuyken, Roman-Benedikt Raether
  • Patent number: 6063939
    Abstract: Unsaturated cyclic ethers of the formula I ##STR1## whereZ is --(CHR.sup.4).sub.q -- or --(CHR.sup.4).sub.q --O--,q is 0, 1, 2 or 3 andR.sup.1,R.sup.2,R.sup.3,R.sup.4 are hydrogen or C.sub.1 -C.sub.4 -alkylare prepared by reacting diols of the formula II ##STR2## where Z, R.sup.1, R.sup.2 and R.sup.3 are as defined above, in the liquid phase at from 150 to 300.degree. C. in the presence of a cobalt-containing supported catalyst which has not been activated by reduction before use and comprises cobalt and a noble metal selected from the group consisting of platinum, palladium, rhodium, iridium, ruthenium, osmium, rhenium or a mixture thereof applied by sol impregnation on an inert support, wherein the supported catalyst is doped with sulfur. Sulfur-doped supported catalysts comprising cobalt and noble metals are also provided.
    Type: Grant
    Filed: January 7, 1999
    Date of Patent: May 16, 2000
    Inventors: Carsten Groning, Michael Hesse, Daniel Heineke, Heinz-Josef Kneuper, Gerhard Fritz
  • Patent number: 6002046
    Abstract: Cyclopropyl alkyl ketones are separated from 3-acyltetrahydrofuran-2-ones by adding an alcohol, water or a water/alcohol mixture to a reaction product containing C.sub.1-4 -alkyl cyclopropyl ketone and 4,5-dihydro-2-alkylfuran by-product and an acid catalyst and reacting the by-product with the added alcohol, water of water/alcohol mixture before, during or after distilling said reaction product; and effectively separating C.sub.1 -.sub.4 -alkyl cyclopropyl ketone from reaction by-products.In the preparation of cyclopropyl alkyl ketones from 3-acyltetrahydrofuran-2-ones very reactive 4,5-dihydro-2-alkylfurans are also produced. By reacting such compounds with nucleophilic compounds, such as alcohols or water, before, during or after distillation of the reaction products, it is possible reliably to separate off the 4,5-dihydro-2-alkylfurans as high-boiling addition compounds.
    Type: Grant
    Filed: March 8, 1999
    Date of Patent: December 14, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Wolfgang Kleemiss, Udo Jegelka, Michael Korell
  • Patent number: 5922863
    Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and functional groups C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.
    Type: Grant
    Filed: October 26, 1995
    Date of Patent: July 13, 1999
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen, Gregory C. Fu
  • Patent number: 5877333
    Abstract: A compound having the structure: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are each independently a hydrogen atom, an alkyl group or an aryl group, or wherein R.sup.2 and R.sup.3 together and R.sup.4 and R.sup.5 together are joined as a cycloalkyl group; wherein R.sup.6 is a hydroxyl group, an alkoxyl group, an aralkyloxy group, or --OSi (R.sup.8 R.sup.9 R.sup.10) in which R.sup.8, R.sup.9 and R.sup.10 are each independently an alkyl group or a phosphate salt group and R.sup.7 is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group.
    Type: Grant
    Filed: November 5, 1997
    Date of Patent: March 2, 1999
    Assignee: Fujirebio Inc.
    Inventors: Masakatsu Matsumoto, Nobuko Watanabe, Hisako Kobayashi, Hiroshi Ikawa
  • Patent number: 5763627
    Abstract: The invention relates to a novel process for simultaneously preparing cyclopropyl alkyl ketones and 4,5-dihydroalkylfurans from 3-acyltetrahydrofuran-2-ones in the presence of a metal salt according to the scheme ##STR1## during the reaction, high-boiling poly (ethylene glycol) dialkyl ethers are then used. By introducing the solvent, the metal salt and the 3-acyltetrahydrofuran-2-one in a molar excess to the metal salt, heating the mixture to 160.degree. to 220.degree. C. and adding further 3-acyltetrahydrofuran-2-one, the desired products are obtained in high yields. The metal salt can, moreover, be recovered in a simple manner by washing with water.
    Type: Grant
    Filed: June 25, 1997
    Date of Patent: June 9, 1998
    Assignee: Huels Aktiengesellschaft
    Inventor: Manfred Kaufhold
  • Patent number: 5698715
    Abstract: A process for the preparation of unsaturated cyclic ethers of the general formula I ##STR1## in which Z denotes --(CHR.sup.4).sub.q or --(CHR.sup.4).sub.q --O--q is 0, 1, 2 or 3 andR.sup.1, R.sup.2, R.sup.3, and R.sup.4 denote hydrogen or C.sub.1 -C.sub.4 alkyl from diols of the general formula II ##STR2## in which, R.sup.1, R.sup.2, and R.sup.3 have the aforementioned meanings, in the presence of a cobalt-containing supported catalyst, wherein the cobalt-containing supported catalyst used contains cobalt and a noble metal--selected from the group consisting of platinum, palladium, rhodium, iridium, ruthenium, osmium, rhenium, or mixtures thereof--in an atomic ratio of from 0.5:1 to 70000:1 on an inert support and optionally basic alkali metal and alkaline earth metal salts, scandium, vanadium, chromium, manganese, iron, nickel, copper, zinc, germanium, tin, lead, antimony, bismuth, or mixtures thereof and the reaction is carried out in the liquid phase at temperatures ranging from 150.degree. to 300.degree.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: December 16, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Jurgen Schroeder, Thomas Fetzer, Christopher William Rieker, Klaus Ebel
  • Patent number: 5693833
    Abstract: Disclosed is a process for converting an iodine-free organotin (IV) compound resulting from the decomposition of an organotin (IV) iodide during the catalytic isomerization of .gamma.,.delta.-epoxyalkenes to 2,5-dihydrofurans to the corresponding, catalytically active organotin (IV) iodide by intimately contacting a catalyst mixture comprising (i) an organotin (IV) iodide, (ii) an iodine-free organotin (IV) compound resulting from the decomposition of the organotin (IV) iodide of component (i), and (iii) a solvent selected from hydrocarbons and chlorocarbons with aqueous hydrogen iodide.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: December 2, 1997
    Assignee: Eastman Chemical Company
    Inventors: Stephen Neal Falling, Patricia Lopez
  • Patent number: 5681969
    Abstract: Disclosed is a process for the continuous production and recovery of 2,3-dihydrofuran (2,3-DHF) by the isomerization of 2,5-dihydrofuran (2,5-DHF) which contains certain impurities to 2,3-dihydrofuran in yields exceeding 95%. The process utilizes, in order, an isomerization zone containing one or more beds of a supported, palladium or platinum catalyst, a product recovery zone comprising a distillation column, a high boiler removal zone and means for feeding the 2,5-DHF component of the bottoms stream from the product recovery zone to the isomerization zone.
    Type: Grant
    Filed: May 3, 1996
    Date of Patent: October 28, 1997
    Assignee: Eastman Chemical Company
    Inventors: Timothy Richard Nolen, Stephen Neal Falling, David Martin Hitch, Jerry Lynn Miller, Daniel Latham Terrill
  • Patent number: 5670672
    Abstract: Disclosed is a process for the preparation of 2,3-dihydrofurans from the corresponding isomeric 2,5-dihydrofurans wherein a 2,5-dihydrofuran compound is contacted with a supported, palladium or platinum catalyst in the presence of carbon monoxide to effect the isomerization of 2,5-dihyrofurans to 2,3-dihydrofurans.
    Type: Grant
    Filed: January 31, 1995
    Date of Patent: September 23, 1997
    Assignee: Eastman Chemical Company
    Inventors: John R. Monnier, Cris S. Moorehouse
  • Patent number: 5629455
    Abstract: The invention relates to a novel process for the simultaneous preparation of cyclopropyl alkyl ketones and 4,5-dihydroalkylfurans from 3-acyltetrahydrofuran-2-ones using a metal salt according to the diagram ##STR1## In the reaction, N-alkyllactams and/or N-acylmorpholines which are high-boiling and only slightly miscible with water are used. By charging the solvent, the metal salt and the 3-acyltetrahydrofuran-2-one in a molar excess with respect to the metal salt, heating the mixture to 160.degree. to 220.degree. C. and metering in further 3-acyl-tetrahydrofuran-2-one, the desired products are obtained in high yields. The metal salt can moreover be recovered in a simple manner by washing with water.
    Type: Grant
    Filed: January 23, 1996
    Date of Patent: May 13, 1997
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Marcel Feld
  • Patent number: RE36719
    Abstract: Disclosed is a process for the preparation of 2,5-dihydrofurans by the homogeneous, liquid phase isomerization of .gamma.,.delta.-epoxyalkene compounds wherein a .gamma.,.delta.-epoxyalkene compound is isomerized in an inert, organic solvent containing a catalytic amount of a soluble copper salt. The process is particularly useful for the conversion of 3,4-epoxy-1-butene to 2,5-dihydrofuran.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: May 30, 2000
    Assignee: Eastman Chemical Company
    Inventor: Gerald C. Tustin