Hydroxy Containing (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/700)
  • Patent number: 5997840
    Abstract: The invention relates to a chiral solid catalyst containing a BEA topology zeolite and a metal-binap complex and to a process for the production of substantially enantiomerically pure products from prochiral starting material with the catalyst. The BEA topology zeolite may be a BETA zeolite, an acid BEA topology zeolite, an acid NU-2 zeolite, or an ammonium BEA topology zeolite. The metal in the metal-binap complex is ruthenium, iridium, nickel, or rhodium. The zeolite is normally impregnated with a solution of the metal-binap complex. The method is applicable to asymmetric hydrogenation of beta functionalized ketones, betaketoesters, functionalized olefins, and .alpha., .beta.-unsaturated functionalized olefins.
    Type: Grant
    Filed: July 13, 1998
    Date of Patent: December 7, 1999
    Assignee: K.V. Leuven Research & Development
    Inventors: Willy Van Brussel, Michel Renard, Diedrik Tas, Rudy Parton, Pierre A. Jacobs, Vilas Hare Rane
  • Patent number: 5986149
    Abstract: The present invention provides processes for recovering alkanols from fluids comprising the alkanol and aqueous hydrobromic acid without forming excessive amounts of alkyl bromide. In certain aspects of the invention, there are provided distillation systems wherein a fluid comprising an alkanol and aqueous hydrobromic acid is introduced into a distillation column at a point between the bottom and the top of the column to thereby separate the alkanol and the hydrobromic acid without causing the production of a significant amount of alkyl bromide.
    Type: Grant
    Filed: April 3, 1998
    Date of Patent: November 16, 1999
    Assignee: Great Lakes Chemical Corporation
    Inventors: Richard J. DeGroot, James T. Ayers, Karl E. Reineke
  • Patent number: 5981811
    Abstract: A process for the preparation of a polyprenol represented by formula (1): ##STR1## where Y and Z individually represent a hydrogen atom or are coupled together to form a carbon-carbon bond; R represents a hydrogen atom or a protective group for a hydroxyl group, and n is 0 or an integer not less than 1, by reacting an organic complex of an alkali metal with a compound represented by formula (2): ##STR2## where either V represents a halogen atom, while W and X are coupled together to form a carbon-carbon bond, or X represents a halogen atom, while V and W are coupled together to form a carbon-carbon bond; A represents a protective group for a hydroxyl group, and Y, Z and n are as defined above.
    Type: Grant
    Filed: April 27, 1998
    Date of Patent: November 9, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Katuji Ujita, Koichi Kanehira, Yoshin Tamai
  • Patent number: 5969195
    Abstract: A process for hydrolyzing alkyl monohalides comprises using activated carbon impregnated with alkali metal hydroxide or alkaline earth metal hydroxide in the presence of water and converting the alkyl monohalides virtually quantitatively into the corresponding alcohols. Apparatus for carrying out the process comprises at least one, preferably two, especially three, reactors (2), especially tubular reactors. The process is also particularly useful for preparing alcohols.
    Type: Grant
    Filed: May 12, 1998
    Date of Patent: October 19, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe Stabel, Gerhard Fahrbach, Werner Neumann
  • Patent number: 5969194
    Abstract: A process for preparing 1,6-hexanediol comprising hydrogenating a starting material containing at least one compound selected from the group consisting of adipic acid, .epsilon.-hydroxycaproic acid, .epsilon.-caprolactone and oligomers of .epsilon.-caprolactone, preferably a substance recovered from a reaction mixture resulting from liquid phase oxidization of cyclohexane for the production of cyclohexanol and cyclohexanone, in a liquid phase in the presence of a solid catalyst containing ruthenium and tin.
    Type: Grant
    Filed: March 4, 1998
    Date of Patent: October 19, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Yoshinori Hara, Koetsu Endou, Seijiro Nishimura
  • Patent number: 5958992
    Abstract: Foam blowing agents blends of 10-90% of n- and/or i-pentane with 90-10% of 142b or 124 are provided, as are polyol premixes and polyurethane foam compositions containing such blends.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: September 28, 1999
    Assignee: Elf Atochem North America, Inc.
    Inventors: Jinhuang Wu, Douglas R. Dillon, Richard M. Crooker
  • Patent number: 5939368
    Abstract: The use of 1-methoxy-2-methyl-3-phenylpropane, 3-methoxy-2,2,3-trimethyl-1-phenylbutane or of 1-(2-methoxypropyl)-4-methylbenzene as perfuming ingredients is described. These two compounds possess an excellent stability in aggressive media and/or at high pH-values, which renders them very useful for application in chlorine bleach. The odor of these two compounds can be described as being of the green type with a nice, strong floral note.
    Type: Grant
    Filed: September 22, 1998
    Date of Patent: August 17, 1999
    Assignee: Firmenich SA
    Inventors: Herve Pamingle, Jean-Marc Gaudin
  • Patent number: 5895824
    Abstract: In a process for preparing polyether polyols containing aromatics by molecular addition of alkylene oxides to H-functional initiators at from 70.degree. C. to 135.degree. C. and pressures of from 0.1 MPa to 1.0 MPa, the alkoxylation is carried out using at least one initiator comprising at least 95% by weight of 2,3 and 3,4 isomers of tolylenediamine, from 0.5 to 4% by weight of 2,4 and 2,6 isomers of tolylenediamine and from 0.1 to 1.5% by weight of more volatile fractions from tolylenediamine production. The polyether polyols prepared by this process can be used as component of a polyol mixture for producing rigid polyurethane foams.
    Type: Grant
    Filed: June 7, 1996
    Date of Patent: April 20, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Stefan Dinsch, Regina Pretzsch, Juergen Winkler, Bernd Guettes, Karl-Heinz Steinchen
  • Patent number: 5874649
    Abstract: The object of the present invention resides in efficiently providing unsaturated alcohol from an .alpha.,.beta.-unsaturated aldehyde.The present invention provides a process for preparing unsaturated alcohol by selectively reducing the aldehyde group of an .alpha.,.beta.-unsaturated aldehyde in the presence of a primary or a secondary alcohol having 2 to 8 carbon atoms using an aluminum alcoholate to produce an unsaturated alcohol such as compounds represented by the formula (III). ##STR1## (wherein R represents an alkyl group having 1 to 3 carbon atoms) wherein the reaction is carried out with addition of a protonic acid.
    Type: Grant
    Filed: November 5, 1997
    Date of Patent: February 23, 1999
    Assignee: Kao Corporation
    Inventors: Shigeyoshi Tanaka, Shinji Kotachi, Junji Koshino, Junko Yamamoto
  • Patent number: 5849935
    Abstract: An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids which are free or esterified with glycerol is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids in the presence of an acid, clay or zeolite catalyst. Alternatively, the .delta.-lactones may be produced by reacting one or more triglycerides which are esters of glycerol with .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification. Optionally, the .delta.-lactones so formed may be further reacted with an alkali in an aqueous solution to produce 5-hydroxy fatty acids.
    Type: Grant
    Filed: September 27, 1995
    Date of Patent: December 15, 1998
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terry A. Isbell, Beth A. Plattner, Robert Kleiman
  • Patent number: 5831102
    Abstract: Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen; andR.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sup.1 and R.sub.
    Type: Grant
    Filed: February 8, 1996
    Date of Patent: November 3, 1998
  • Patent number: 5817906
    Abstract: The present invention relates to a process for the production of light olefins comprising olefins having from 2 to 4 carbon atoms per molecule from a crude oxygenate feedstock. The crude oxygenate feedstock comprises an alcohol, and water. The process comprises passing the crude oxygenate feedstock to catalyst to a distillation with reaction zone to convert the alcohol to an ether and produce an ether product having a reduced water relative to the crude oxygenate feedstock and a first water stream. The ether product is passed to an oxygenate conversion zone containing a metal aluminosilicate catalyst to produce a light olefin stream.
    Type: Grant
    Filed: August 10, 1995
    Date of Patent: October 6, 1998
    Assignee: UOP LLC
    Inventors: Terry L. Marker, Christopher David Gosling
  • Patent number: 5801260
    Abstract: Novel substrates of phospholipases, lysophospholipases and lipases are disclosed.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 1, 1998
    Assignee: LaJolla Pharmaceuticals Co.
    Inventors: Lin Yu, Robert John Termansky
  • Patent number: 5786521
    Abstract: Hydroxymethylcyclopropane is prepared from alkyl cyclopropanecarboxylates by reduction with hydrogen in a process in which use is made of a reduced pelletized catalyst which is obtainable by pressing a mixture of pulverulent copper, zinc and aluminum oxides and subsequent reduction. This process has the advantage that it uses a low-toxicity catalyst which has a long operating life and is particularly suitable for a continuous process and requires relatively low reaction temperatures.
    Type: Grant
    Filed: March 14, 1997
    Date of Patent: July 28, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Darsow, Lutz Frohn, Reinhard Langer
  • Patent number: 5767326
    Abstract: A process for preparing hydroxymethylcyclopropane, in which formylcyclopropane is hydrogenated over copper chromite, zinc chromite and/or copper/zinc catalysts. The process may be batchwise or continuous.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: June 16, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Wolfgang Kleemiss, Marcel Feld
  • Patent number: 5756306
    Abstract: A process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide which comprises treating an aldehyde and prussic acid or an .alpha.-hydroxynitrile with a microorganism having nitrilase or nitrile hydratase activity in an aqueous medium and maintaining the aldehyde concentration and/or the .alpha.-hydroxynitrile concentration in the reaction mixture within a predetermined range. Also disclosed is a process for producing an .alpha.-hydroxy acid or an .alpha.-hydroxyamide from an aldehyde and prussic acid with a microorganism in an aqueous medium, which comprises maintaining the cyanogen concentration in the reaction mixture within a predetermined range and supplying the aldehyde to the reaction mixture at a predetermined ratio to the prussic acid.
    Type: Grant
    Filed: November 8, 1996
    Date of Patent: May 26, 1998
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Yasumasa Yamaguchi, Masahiro Ushigome, Takeshi Kato
  • Patent number: 5750679
    Abstract: A process for obtaining pharmacologically active compounds from complex mixtures of substancesFree organic acids, hydroxy acids, fatty alcohols, sugars and hydroxy-substituted steroids are obtained from complex mixtures of substances by mixing the material to be extracted with a polar solvent, drying the resulting mixture, subsequently silylating, esterifying or acylating, and extracting the resulting material with a supercritical fluid under a pressure of more than 200 bar.
    Type: Grant
    Filed: August 25, 1994
    Date of Patent: May 12, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Haas, Heinz Engelhardt, Stefan Mullner
  • Patent number: 5728896
    Abstract: Hydroxymethyl-cyclopropane (cyclopropyl-methanol) can be obtained in a manner which is both economical and environment-friendly by catalytic hydrogenation of cyclopropanecarboxylic acid alkyl esters under increased pressure at elevated temperature if a chromium-free zinc oxide catalyst is employed as the catalyst.
    Type: Grant
    Filed: February 15, 1996
    Date of Patent: March 17, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Lutz Frohn, Reinhard Langer, Gerhard Darsow, Eberhard Zirngiebl, Jorg-Dietrich Jentsch, Bernd Pennemann, Christoph Tiburtius
  • Patent number: 5688975
    Abstract: Molecular sieve compositions have been synthesized which are resistant to the loss of framework atoms. Specifically, the molecular sieves of the invention have the empirical formulamA: (M.sub.w Al.sub.x Si.sub.y)O.sub.2where A is at least one rare earth metal, M is chromium or titanium and "m", "w", "x" and "y" are the mole fractions of A, M, Al and Si respectively. Applicants have discovered that the rare earth metals prevent loss of chromium and titanium from the framework and degradation of the molecular sieve. Along with the composition, a process for preparing the composition and processes using the composition are disclosed and claimed.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: November 18, 1997
    Assignee: UOP
    Inventors: Vinayan Nair, Deng-Yang Jan, Robert Lyle Patton, Ben A. Wilson, Donald F. Best
  • Patent number: 5635542
    Abstract: The present invention relates to a process for the production of hydroxyl-group-containing compounds suitable for the polyisocyanate polyaddition process from polyurea and/or polyurethane polyurea wastes by treating polyurea and/or polyurethane polyurea wastes with diols and/or polyols at temperatures from 160.degree. to 260.degree. C., the water present in the reaction vessel preferably being removed by distillation during the heating-up phase, characterized in that 1,3-dicarbonyl compounds are added to the reaction mixture before or during the reaction.
    Type: Grant
    Filed: June 16, 1995
    Date of Patent: June 3, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Munzmay, Werner Rasshofer, Walter Meckel
  • Patent number: 5621084
    Abstract: This invention relates to a process for the removal of an allyl or allyloxycarbonyl group from an allyl or allyloxycarbonyl group protected compound (such as an allylic ester, carbonate, carbamate, O-allyl derivatives or N-allyl derivatives), which comprises contacting the allyl or allyloxycarbonyl group protected compound with a sulfinic acid compound, in the presence of a palladium catalyst in a reaction-inert solvent. Preferably, the sulfinic acid compound is represented by the formula:X--SO.sub.2 M (I)wherein X is C.sub.1-20 alkyl, substituted C.sub.1-20 alkyl (wherein the substituent(s) are independently halo, nitro, sulfo, oxo, amino, cyano, carboxy, hydroxy or moieties derived therefrom), phenyl, substituted phenyl (wherein the substituent(s) are independently C.sub.1-3 alkyl, halo nitro, sulfo, oxo, amino, cyano, carboxy, hydroxy, acetamido or moieties derived therefrom), furyl or thienyl; and M is hydrogen, an alkali metal or ammonium salt residue.
    Type: Grant
    Filed: April 3, 1995
    Date of Patent: April 15, 1997
    Assignee: Pfizer Inc.
    Inventors: Msanori Honda, Hiromasa Morita, Isao Nagakura
  • Patent number: 5616815
    Abstract: This invention relates to a process for hydrating olefins to the corresponding alcohols in the vapour phase in the presence of a catalyst system comprising a heteropolyacid catalyst supported on niobia. By using niobia as support, it is possible not only to increase the space-time-yield of the process but also to prolong the life of the support thereby reducing the frequency with which the support is changed or replaced on a plant. The process is particularly suited to producing ethanol from ethylene and isopropanol from propylene.
    Type: Grant
    Filed: November 13, 1995
    Date of Patent: April 1, 1997
    Assignee: BP Chemicals Limited
    Inventor: Martin P. Atkins
  • Patent number: 5475151
    Abstract: Disclosed is a process for the preparation of cyclopropylmethanol(hydroxymethylcyclopropane) by the hydrogenation of cyclopropanecarboxaldehyde in the presence of a cobalt or nickel catalyst.
    Type: Grant
    Filed: November 28, 1994
    Date of Patent: December 12, 1995
    Inventors: Shaowo Liang, Timothy W. Price
  • Patent number: 5449840
    Abstract: A cyclopropane derivative of formula (I) ##STR1## wherein B.sup.1 is a purine or pyrimidine residue, R.sup.1 and R.sup.2 are, independently, hydrogen or a protecting group for hydroxyl and each of k, m and n represents, independently, an integer of 1 or 2 is useful for its antiviral effect.
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: September 12, 1995
    Assignee: Ajinomoto Co., Inc.
    Inventors: Satoshi Hatsuya, Takaaki Sekiyama, Takashi Tsuji, Satoshi Iwayama, Masahiko Okunishi
  • Patent number: 5441716
    Abstract: A chemisorption reaction process is carried out under conditions in which the volumetric expansion of the complex compound reaction product is restricted, and at half-cycle reaction periods of less than 30 minutes each, and/or in a reaction chamber having a maximum mean mass diffusion path length of less than about 15 mm, and/or a maximum heat diffusion path length of less than 1.5 mm.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: August 15, 1995
    Assignee: Rocky Research
    Inventor: Uwe Rockenfeller
  • Patent number: 5406001
    Abstract: The present invention relates to a method for the continuous preparation of a mixture of a cycloalkanone, a cycloalkanol and a cycloalkylhydroperoxide. In the method, a cycloalkane, corresponding to the cycloalkenone, cycloalkenol and cycloalkylhydroperoxide, is oxidized in a continuous process, with the aid of an oxygen-containing gas, in the absence of a metal catalyst, at a temperature of between 130.degree. C. and 200.degree. C. The oxidation is at least partly carried out in the presence of between 0.002 and 2 mmol of a phenolic compound per kg of reaction mixture (mmol/kg).
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: April 11, 1995
    Assignee: DSM N.V.
    Inventors: Johannes G. H. M. Housmans, Ubaldus F. Kragten
  • Patent number: 5397810
    Abstract: The present invention relates to a novel polyol obtained by using a specified polyhydric alcohol, polyoxyalkylene polyol, aliphatic amine and/or alkamlamine as a raw material and adding an organic polycarboxylic acid or its anhydride and an alkylene oxide; a polyurethane resin prepared from said novel polyol and an organic polyisocyanate; a rigid polyurethane foam prepared by using a hydrochlorofluorocarbon or hydrofluorocarbon foaming agent which has very low public hazards; and a composite utilizing thereof.The production of rigid polyurethane foam by using the polyol of the invention can be carried out in good operation efficiency and low public hazards. Additionally, properties of the foam thus obtained is equivalent to those of rigid polyurethane foams obtained by using conventional chlorofluorocarbons. Consequently, the rigid polyurethane foam of the invention is very useful for insulation materials and structural insulation materials.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: March 14, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Satoshi Ozaki, Tsukuru Izukawa, Haruhiko Kawakami, Takayoshi Masuda, Masayuki Kimura, Toshio Nozawa, Masahiko Hashiba
  • Patent number: 5396011
    Abstract: An aromatic compound (such as benzene) is alkylated with a alkene (such as propylene) by contacting the two compounds together in the presence of a tungsten on zirconia catalyst. The reaction preferably takes place at elevated temperature and elevated pressure. The process of the invention has very high selectivity and conversion, and produces no or only very low amounts of undesirable oligomers (as measured by bromine number).
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: March 7, 1995
    Assignee: Mallinckrodt Chemical, Inc.
    Inventor: Deborah K. Kuhn
  • Patent number: 5371270
    Abstract: A method of manufacturing chlorine-free cyclopropanecarboxylic acid methyl ester is described wherein a first portion of alkali methoxide is added to a high-boiling solvent, followed by a second portion of methoxide with an equimolar portion of 4-chlorobutyric acid. The ester product can be readily hydrogenated catalytically to the corresponding carbinol.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: December 6, 1994
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Josef Metz
  • Patent number: 5350879
    Abstract: Base-catalyzed transesterification may be effected in the presence of certain metal oxide solid solutions and layered double hydroxides as the basic catalyst. Use of the latter materials as the base catalyst readily permits one to conduct transesterification in a continuous manner. Such a continuous process is applicable to esters generally and is not limited to any particular structural types of esters or alcohols. Transesterification of detergent range alkyl acetates by this method leads to the formation of the corresponding detergent range alcohols in excellent yield and with quite high selectivity.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: September 27, 1994
    Assignee: UOP
    Inventors: Dusan J. Engel, Thomas P. Malloy, Peter K. Nickl
  • Patent number: 5338768
    Abstract: Substantially closed cell rigid polyurethane foam cores of laminates are disclosed which are scorch-free, have a density of 50 kg/m.sup.3 and are made using water as the sole or main blowing agent and without the need to use a CFC. The foams are prepared from polyol compositions comprising the product of alkoxylating an initiator having a functionality of more than 2, at least one aromatic ring and at least one amino nitrogen atom. The initiator is preferably a Mannich condensate of a phenolic compound, formaldehyde and ammonia or an alkanolamine and the polyol is preferably used together with a second polyol having a functionality (or average functionality) of at least 1 but less than 3 and a molecular weight M.sub.w (or average molecular weight) of 250 to 4000.
    Type: Grant
    Filed: September 11, 1992
    Date of Patent: August 16, 1994
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Jelle D. Boer, Bernard Auguet
  • Patent number: 5338763
    Abstract: Compounds containing alcoholic hydroxyl groups suitable as a starting material for the isocyanate polyaddition process by the alcoholysis of polyisocyanate polyaddition products are produced. Polyurethane urea or polyurea waste products having a molar ratio of urea groups to urethane groups of from 1:20 to 1:0 are heated in size reduced form to temperatures of from 120.degree. to 250.degree. C. together with B) polyhyhdric alcohols in the molecular weight range of from 62 to 250 in a ratio by weight of A:B of from 3:1 to 1:10. At least 10% of the polyhydric alcohol B put into the process is subsequently removed by distillation under reduced pressure. A total of up to 1000% by weight, based on the weight of polyurethane urea or polyurea waste A, of one or more polyhydroxy compounds having a molecular weight above 250 which is (are) not volatile under the distillation conditions may optionally be added to the mixture before and/or after removal of the excess alcohol B by distillation.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: August 16, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Munzamy, Werner Rasshofer, Karl-Heinz Dorner, Ulrich Limna
  • Patent number: 5312950
    Abstract: A method for the purification of alcohols from organic soluble impurities has been discovered comprising treating the crude alcohol with a cyclic anhydride followed by an aqueous base and extracting the corresponding half-ester into aqueous solution leaving the impurities in organic solution. This method is particularly useful for the separation of chiral, nonracemic alcohols from the corresponding antipodal ester (the mixture resulting from an enzymatic kinetic resolution) because the separation is non-chromatographic and the enantiomeric integrity of the products is maintained.
    Type: Grant
    Filed: August 31, 1993
    Date of Patent: May 17, 1994
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 5298231
    Abstract: Reaction rates in chemisorption reactions involving solid reactants and gaseous ligands are improved by maintaining optimized solid density throughout the reaction. Methods and apparatus which restrict volumetric solid expansion, compression of the solid reactant, and mixture with inert solid porous or particulate materials are disclosed.
    Type: Grant
    Filed: November 13, 1992
    Date of Patent: March 29, 1994
    Assignee: Rocky Research
    Inventor: Uwe Rockenfeller
  • Patent number: 5254747
    Abstract: Compounds are provided which comprise a fluorocarbon terminal portion and a chiral hydrocarbon terminal portion, said terminal portions being connected by a central core, said compounds having tilted smectic mesophases or having latent tilted smectic mesophases which develop when said compounds having said latent mesophases are in admixture with said compounds having tilted smectic mesophases or said compounds having latent tilted smectic mesophases.
    Type: Grant
    Filed: May 21, 1991
    Date of Patent: October 19, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Eugene P. Janulis
  • Patent number: 5227538
    Abstract: A process is provided for the catalytic asymmetric reduction of ketones to provide alcohol reaction products which are enriched in one enantiomer. The asymmetric reduction is accomplished utilizing an achiral metal precatalyst in combination with an optically active additive.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: July 13, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Robert B. Grossman
  • Patent number: 5220020
    Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: June 15, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
  • Patent number: 5208388
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5202502
    Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: April 13, 1993
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5175371
    Abstract: An improved process for preparing either optically pure enantiomer of the bark beetle pheromones ipsenol and ipsdienol is provided. The process is also applicable to the condensation of aldehydes of widely varying properties to the corresponding chiral alcohol.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: December 29, 1992
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5128488
    Abstract: The asymmetric hydrogenation of carbonyl compounds is carried out in the presence of at least one transition metal complex MZq(M=metal of group VIII of the Periodic Classication; Z=ligand selected among the atoms and the molecules which may complex the metal M; and q=degree of corrdination of M) and of at least one chiral phosphorous-containing ligand having formula (I), wherein R is hydrocarbonated radical (alkyl, cycloalkyl and aryl); R.sup.1 is H, hydrocarbonated radical or PR.sub.2 ; R.sup.2 is H or hydrocarbonated radical R.sup.3,R.sup.4, necessarily different, are H and optionally functionalized hydrocarbonated radicals; R.sup.5 and R.sup.6 are H and optionally functionalized hydrocarbonated radicals; one of the radicals R.sup.3 and R.sup.4 possibly carrying a function - OPR.sub.2 or NPR.sub.2, R.sup.5 and R.sup.6 being in this case H when R.sup.1 is PR.sub.2 ; R.sup.2 and R.sup.3 and the atoms of N and C which cary them respectively forming a heterocycle; or R.sup.2 and R.sup.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: July 7, 1992
    Assignee: Societe Chimique des Charbonnages S.A.
    Inventors: Andre Mortreux, Francis Petit
  • Patent number: 5117013
    Abstract: Disclosed is a novel process for the preparation of epoxyalkanes and epoxycycloalkanes which comprises hydrogenating .gamma.,.delta.-epoxyalkenes or .gamma.,.delta.-epoxycycloalkenes in the presence of a rhodium catalyst. The process is especially useful for the preparation of 1,2-epoxybutane from 3,4-epoxy-1-butene.
    Type: Grant
    Filed: July 11, 1991
    Date of Patent: May 26, 1992
    Assignee: Eastman Kodak Company
    Inventor: Stephen N. Falling
  • Patent number: 5116916
    Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: May 26, 1992
    Assignee: Union Oil Company of California
    Inventor: Donald C. Young
  • Patent number: 5113021
    Abstract: A process for the manufacture of .alpha.- and .beta.-irone, namely the compounds of formula I, as well as novel intermediates in the process is provided.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: May 12, 1992
    Assignee: Givaudan Corporation
    Inventors: Georg Frater, Daniel Helmlinger
  • Patent number: 5110961
    Abstract: The invention relates to a catalytic process for the synthesis of an alcohol by reaction of an epoxide with a nucleophilic compound containing a labile hydrogen, such as an alcohol, a phenol, a primary amine or a carboxylic acid.The catalyst is a metal complex of general formula (I)[M[Co(CO).sub.4 ].sub.2 ].sub.x in which x is equal to 1 or 2 and M denotes tin, lead and cadmium.The reaction preferably takes place in the presence of carbon monoxide.This process makes it possible to increase the yield and the selectivity of the reaction and the stereoselectivity for alcohol in the case of which the hydroxyl formed is attached to the least hindered carbon atom of the epoxide.The invention also relates to the new complexes of formula (I) in which x equals 2.It also relates to a process for the electrosynthesis of these new compounds by electroreduction of Co.sub.2 (CO).sub.
    Type: Grant
    Filed: December 14, 1990
    Date of Patent: May 5, 1992
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Serge Lecolier, Andre Mortreux, Francis Petit, Henri Samain
  • Patent number: 5097062
    Abstract: The synthesis of stable, ten-membered cyclic conjugated enediynes is described. Said compounds were successfully employed to cleave double-stranded DNA spontaneously at ambient temperatures.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: March 17, 1992
    Inventors: Kyriacos C. Nicolaou, Guido Zuccharello, Yuji Ogawa
  • Patent number: 5095147
    Abstract: 2,2-Difluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl andX represents hydroxymethyl, 2-hydroxyethyl, isocyanato, amino, amino hydrohalide or a radical of the formula --CO--R.sup.1, whereR.sup.1 represents hydrogen, hydroxyl, alkoxy, alkyl, halogen or amino,are intermediates for fungicides.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5095136
    Abstract: A process is provided for preparing isoprenoid cyclopropane 1,1-dicarboxylates and derivatives thereof including the corresponding monocarboxylate, monocarboxylic acid and alcohol derivatives thereof, all of which are useful in preparing squalene synthetase inhibitors which inhibit cholesterol biosynthesis, and also useful in preparing pyrethrin insecticides.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: March 10, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Scott A. Biller, Cornelia Forster
  • Patent number: 5081283
    Abstract: Novel intermediates for fungicides, comprising fluorocyclopropyl derivatives of the formula ##STR1## in which R represents alkyl, optionally substituted aryl or optionally substituted aralkyl,X represents hydrogen, chlorine or bromine andR.sup.1 represents hydroxyl, alkoxy, alkyl or halogen.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: January 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Rudolf Gassen, Bernd Baasner
  • Patent number: 5028406
    Abstract: A crystalline, galliosilicate molecular sieve having the mordenite structure and the following composition expressed in terms of oxide mole ratios in the anhydrous state:Ga.sub.2 O.sub.3 :xSiO.sub.2 :yM.sub.2 O:tQ.sub.2 Owhere M is an alkali metal, preferably sodium, Q is a quaternary ammonium cation, preferably a benzyltriethylammonium cation, x equals 5.0 to 30, y equals 0.1 to 0.99, preferably 0.40 to 0.90, t equals 0.01 to 0.9, preferably 0.1 to 0.6 and yet equals about 1.0. The crystalline, galliosilicate molecular sieve of the invention may be employed, after reducing its alkali metal content and decomposing Q, as a component of a catalyst which can be used in a variety of chemical conversion processes.
    Type: Grant
    Filed: November 29, 1989
    Date of Patent: July 2, 1991
    Assignee: Union Oil Company of California
    Inventor: Mario L. Occelli