Unsubstituted Acids Of The Acetic Series Patents (Class 560/231)
  • Patent number: 6444841
    Abstract: A highly pure hydroquinone dietser derivative can be produced from the reaction product of ketoisophorone with an acylating agent in a high yield by a simple and easy operation. In the presence of an acid catalyst, a cyclohex-2-ene-1,4-dione derivative shown by the following formula (3) was allowed to react with an acylating agent (e.g., acetic anhydride), and the reaction product was purified by crystallization to obtain a hydroquinone diester derivative shown by the following formula (1). The compound (1) contains about 0 to 4% by weight of a catechol diester derivative represented by the following formula (2), being highly pure. As a solvent for crystallization, a mixed solvent of an organic carboxylic acid (e.g., acetic acid) corresponding to the acylating agent and water may be used. In the formulae, R1 and R2 each represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group.
    Type: Grant
    Filed: October 30, 1998
    Date of Patent: September 3, 2002
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Ikuo Takahashi, Hikaru Shibata
  • Publication number: 20020099238
    Abstract: This invention provides an environmentally clean process for the selective esterfication of a tertiary alcohol (I) by an acid anhydride (II) to produce corresponding tertiary ester (III) and carboxylic acid (V), using a reusable solid catalyst (IV) comprising one or more halides of indium, gallium, zinc and iron. The process comprises: (i) contacting a mixture of (I) and (II) in the absence or presence of a non aqueous solvent with the fine particles of (IV) in a stirred hatch reactor provided with a reflux water condenser at atmospheric pressure at the reaction conditions, such that the mole ratio of (II) to (I) is in the range from about 0.1 to about 10.0; the weight ratio of (IV) to (I+II) is in the range from about 0.005 to about 0.5; the reaction temperate is below about 80° C.; and the reaction period is in the range from about 0.
    Type: Application
    Filed: November 29, 2000
    Publication date: July 25, 2002
    Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
    Inventors: Vasant Ramchandra Choudhary, Kshudiram Mantri, Suman Kumar Jana
  • Patent number: 6420308
    Abstract: A shell impregnated catalyst of Pd—Au produced on a silica support to have a Pd loading of 1.8 g/L of catalyst to about 7.2 g/L and a Au to Pd weight ratio of 0.3 to 2.0 by impregnating the support with aqueous solutions of palladium and gold salts or acids and thereafter precipitating water insoluble compounds of Pd and Au on the with alkali metal silicate or hydroxide solutions, then dried, and the surface precipitated compounds of Pd and Au are then reduced by reaction with ethylene or hydrogen at a temperature of greater than 150° C. up to 310° C. or with hydrogen up to 299° C. until substantially all of the Pd and Au contents are reduced to a free metal state, after which the support is impregnated with potassium acetate to an extent of 6 to 7 weight percent of the weight of the total catalyst.
    Type: Grant
    Filed: July 7, 2000
    Date of Patent: July 16, 2002
    Assignee: Saudi Basic Industries Corp
    Inventor: Alla Konstantin Khanmamedova
  • Publication number: 20020087027
    Abstract: A catalyst composition suitable for use as a catalyst for the preparation of an ester comprises (a) an organometallic compound which is the reaction product of an orthoester or condensed orthoester of titanium, zirconium or aluminum, an alcohol containing at least two hydroxyl groups, an organophosphorus compound containing at least one P—OH group and preferably a base, and (b) a compound of germanium, antimony or tin. A process for the preparation of an ester comprises carrying out an esterification reaction in the presence of the catalyst composition. In a further embodiment the organometallic compound comprises the reaction product of, in addition, a 3-hydroxy carboxylic acid.
    Type: Application
    Filed: November 26, 2001
    Publication date: July 4, 2002
    Applicant: ACMA Limited
    Inventors: Charles M. Lindall, John Ridland, Neville Slack
  • Patent number: 6403346
    Abstract: Enzymatic processes can produce intermediates for manufacturing retiferol derivatives that are useful for treating or preventing hyperproliferative skin diseases and for reversing conditions associated with photodamage. These processes can use as a starting material trihydroxycyclohexane, which can be chemically modified by a process that includes an enzymatic step, typically involving lipases of EC-class 3.1.1.3 or 3.1.1.34.
    Type: Grant
    Filed: September 6, 2001
    Date of Patent: June 11, 2002
    Assignee: Basilea Pharmaceutica AG
    Inventors: Hans Hilpert, Beat Wirz
  • Patent number: 6399812
    Abstract: Aliphatic esters, R'COOR are produced by reacting the corresponding alcohol, ROH having carbon numbers of the alkyl groups, R′ and R, between 0 and 9 and 1 and 10, respectively, with molecular oxygen in the presence of a dual functional catalyst comprising metal on acidic solid support. In particular, the process is used advantageously for production of ethyl acetate by conversion of ethanol. The reaction mixture from the reactor is separated through azeotropic distillation to recover the ethyl acetate as product and the by-product, acetaldehyde and acetic acid which could be recycled for further reaction. The process is characterized by high conversion of ethanol, high selectivity and high yield for ethyl acetate and low waste stream generation. The preferred catalyst is Pd on zeolites which is active, selective, stable and regenerable.
    Type: Grant
    Filed: April 27, 2000
    Date of Patent: June 4, 2002
    Inventors: Tsoung Y. Yan, Jen-Ray Chang
  • Publication number: 20020058833
    Abstract: A fluid bed process for the manufacture of vinyl acetate from ethylene, acetic acid and oxygen comprising feeding ethylene and acetic acid into a fluid bed reactor through a first inlet, introducing the oxygen into the reactor through a second inlet, co-joining the oxygen, ethylene and acetic acid in the reactor in contact with a fluid bed catalyst to produce vinyl acetate. The particle size diameter of the particulate catalyst material has a range of 60% of the particles being below 200 microns (0.1 mm) with no more than 40% of the particles being below 40 microns (0.04 mm).
    Type: Application
    Filed: October 17, 2001
    Publication date: May 16, 2002
    Inventors: Larry M. Cirjak, Michael F. Lemanski, David R. Wagner, Nancy C. Benkalowycz, Patricia R. Blum, Marc A. Pepera, Christos Paparizos
  • Patent number: 6384269
    Abstract: The compounds of formula in which the symbols R1, R2, R3 and R4 represent independently from each other a hydrogen atom or a methyl or ethyl group, the symbol X represents an oxygen atom or an alkylene group of formula in which n is an integer from 1 to 3, the symbols R6 and R7 represent each a hydrogen atom or a methyl or ethyl group, and R5 represents an alkyl or alkoxy group from C1 to C4, linear or branched, an alkenyl group from C2 to C4, linear or branched, or a group of formula in which Y has the same meaning as X and R8 is a linear or branched alkyl group from C1 to C4 or a linear or branched alkenyl group from C2 to C4, are novel compounds showing musky odors and which confer musky-velvety, voluminous and very tenacious notes to the products to which they are added.
    Type: Grant
    Filed: April 20, 2000
    Date of Patent: May 7, 2002
    Assignee: Firmenich SA
    Inventor: Alvin S. Williams
  • Patent number: 6369243
    Abstract: A method is provided for catalytically transforming a functional group within a first reactant by reaction with a second reactant in the presence of a nonmetallic, organic catalyst composition composed of a heteroatom-containing activator and an acid, or a salt of a heteroatom-containing activator and an acid. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. The heteroatom of the activator is a Group 15 or Group 16 element such as nitrogen, oxygen, sulfur or phosphorus, and exemplary heteroatom-containing activators are amines. Chiral heteroatom-containing activators can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.
    Type: Grant
    Filed: January 18, 2000
    Date of Patent: April 9, 2002
    Assignee: The Regents of the Univerisity of California
    Inventors: David W. C. MacMillan, Kateri A. Ahrendt
  • Publication number: 20020037333
    Abstract: A hepatic disorder suppressant comprising extracts having hepatic disorder suppressing effect as effective ingredients, wherein the extracts is obtained by extracting an avocado plant and/or a processed product thereof with an organic solvent is disclosed.
    Type: Application
    Filed: March 30, 2001
    Publication date: March 28, 2002
    Inventors: Yaushi Arimoto, Hiroyuki Suganuma, Takahiro Inakuma, Kimio Sugiyama, He Puming, Hirokazu Kawagishi
  • Patent number: 6359147
    Abstract: Reactions of ring systems, such as aziridines, oxetanes and oxiranes with carboxylic acids, anhydrides, imides, lactones and carbonate esters are catalyzed by C3-C60, substituted or unsubstituted, straight or branched-chained, alkyl, aryl, or aralkyl carboxylate Cr+3 salts, preferably chromium +3 octoate. The catalysts also accelerate the reaction of hydroxy compounds with anhydrides, and of thiiranes with anhydrides. The catalysts selectively enhance the conversion of ring systems to form monomers, prepolymers, copolymers, functional end-group monomers, functional end-group prepolymers, and functional end-group polymers rather than forming homopolymers. By varying the catalyst concentration, molar ratios, and reaction temperatures, the reaction time required to form the desired product can be controlled.
    Type: Grant
    Filed: April 3, 2000
    Date of Patent: March 19, 2002
    Assignee: Dimension Technology Chemical Systems, Inc.
    Inventors: Renato R. Rindone, W. Kenneth Musker
  • Patent number: 6359181
    Abstract: The present invention provides a novel compound represented by the general formula I; wherein R is H or COR3; R1 is H, R2, phenyl, or COR3, wherein R2 is C1-C5 lower alkyl and R3 is R2 or phenyl; Z is CH2 or O; Y is OH, OCOR3 or ═O; x is 0 or 1; and X is C1-C5 n-alkyl, C3-C7 cycloalkyl, phenyl, furanyl, thienyl or substituted derivatives thereof, wherein the substituents maybe selected from the group consisting of C1-C5 alkyl, halogen, CF3, CN, NO2, NR42, CO2R4 and OR4 wherein R4 is hydrogen or C1-C5 alkyl and dotted lines represent the presence or absence of a double bond and wavy lines represent a cis or trans bond. These novel compounds are especially useful for treating elevated intraocular pressure (ocular hypertension) and glaucoma.
    Type: Grant
    Filed: July 26, 2001
    Date of Patent: March 19, 2002
    Assignee: Allergan Sales, Inc.
    Inventors: Robert M. Burk, Mark Holoboski, Mari F. Posner
  • Publication number: 20020028963
    Abstract: Carboxylic esters are prepared by a process, which comprises reacting dicarboxylic or polycarboxylic acids or their anhydrides with alcohols in a liquid medium with the concomitant removal of water formed by the esterification reaction by azeotropic distillation together with the alcohol in the medium, wherein the amount of liquid removed from the reaction medium by azeotropic distillation is replaced in whole or in part with the alcohol.
    Type: Application
    Filed: September 5, 2001
    Publication date: March 7, 2002
    Applicant: OXENO OLEFINCHEMIE GMBH
    Inventors: Dietmar Gubisch, Uwe Ernst, Wilfried Bueschken
  • Publication number: 20020026075
    Abstract: The preparation of a carboxylic ester by direct reaction of a carboxylic acid and an alcohol catalyzed by a sulphonic acid R—SO3H is carried out in the presence of a solid comprising tertiary amine functions.
    Type: Application
    Filed: June 12, 2001
    Publication date: February 28, 2002
    Inventor: Christian Gancet
  • Patent number: 6348620
    Abstract: The present invention is relative to a method for the homogeneous, catalytic, enantioselective hydrogenation of compounds of the general formula (I) with the aid of compounds of the general formula (II) The use of the hydrogenated derivatives in organic synthesis.
    Type: Grant
    Filed: June 18, 1999
    Date of Patent: February 19, 2002
    Assignee: Degussa-Huls AG
    Inventors: Paul Knochel, Juan Jose Almena Perea, Karlheinz Drauz, Ingo Klement
  • Patent number: 6348622
    Abstract: There is provided a compound of the formula[I]: wherein R represents a hydrogen atom or a protective group for a hydroxyl group; and A represents a hydrogen atom, a halogen atom or a group of the formula A1: Q represents Q3: when A represents a halogen atom or a protective group for a hydroyl group, A represents Q4:  wherein R1 and R2 represent a hydrogen atom or a protective group for a hydroxyl group; and when A represents a hydrogen atom, Q is Q2:
    Type: Grant
    Filed: February 9, 2000
    Date of Patent: February 19, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiya Takahashi, Shinzo Seko, Takashi Miki
  • Patent number: 6344583
    Abstract: Applicants have developed a process for the oxidation of ketones to esters. The process involves contacting the ketone with hydrogen peroxide and a catalyst at oxidation conditions. The catalyst is a molecular sieve represented by the empirical formula: (MwSnxTiySi1−x−y−zGez)O2 where M is a trivalent metal such as aluminum or boron. These molecular sieves have a microporous three dimensional framework structure of at least SiO2 and SnO2 tetrahedral units, a crystallographically regular pore system and the characteristic x-ray diffraction pattern of zeolite beta.
    Type: Grant
    Filed: April 25, 2000
    Date of Patent: February 5, 2002
    Assignee: UOP LLC
    Inventors: Avelino Corma Canos, Laszlo T. Nemeth, Michael Renz, Jaime G. Moscoso
  • Patent number: 6329543
    Abstract: The present invention relates to processes for synthesis of isobornyl (meth)acrylate by reacting camphene with (meth)acrylic acid in the presence of sulfuric acid and at least one compound having inhibiting action. Aqueous sulfuric acid with an acid concentration in the range of 65 to 85 wt % is used. Isobornyl (meth)acrylate can advantageously be distilled from a mixture containing sulfuric acid in the presence of 2,6-di-tert-butyl-&agr;-(dialkylamino)-p-cresol.
    Type: Grant
    Filed: May 3, 2000
    Date of Patent: December 11, 2001
    Assignee: Roehm GmbH & Co KG
    Inventors: Joachim Knebel, Doris Saal
  • Patent number: 6323174
    Abstract: The invention provides a chain diene compound with desirable regioselectivity, in the presence of a specific ruthenium compound. This chain diene compound is a promising raw material for terpene. It has a structure represented by the general formula (I): wherein R1 represents H, a C1-C6 alkyl group which may be substituted or a C2-C6 alkenyl group which may be substituted, R2 represents a phenyl group which may have a C1-C4 alkyl group or a C1-C12 acyloxy group which may have a phenyl group or a naphthyl group, or a benzyl group or R2 is a hydroxy group which reversibly forms an aldehyde group through shifting of the position of the double bond adjacent to said hydroxy group. The chain diene compound is produced by reacting 2-substituted-1,3-butadienes with terminal olefins in the presence of a ruthenium compound in a hydrophilic solvent.
    Type: Grant
    Filed: May 16, 2000
    Date of Patent: November 27, 2001
    Assignee: Takasago International Corporation
    Inventors: Mitsuhiko Fujiwhara, Takenobu Nishikawa, Yoji Hori, Toshimitsu Hagiwara, Hisao Iwai, Takashi Miura
  • Patent number: 6320069
    Abstract: Process for producing an optically active ester by reaction of a racemic alcohol with an optically active amino or tartaric acid derivative, a process for producing an optically active alcohol by hydrolysis of the optically active ester, a process for converting an alcohol into a ketone by oxidation, a method for stably storing an optically active ketone, and a new optically active amino acid ester and a new optically active tartaric acid ester.
    Type: Grant
    Filed: December 22, 1998
    Date of Patent: November 20, 2001
    Assignee: Toray Industries, Inc.
    Inventors: Haruyo Sato, Sakie Nakai, Keiko Funabashi, Shiho Iwata
  • Patent number: 6316664
    Abstract: Formic ester is transesterified with a hydroxyl-containing compound in the presence of a tertiary amine as transesterification catalyst to form a formic ester which differs from the formic ester used as reactant, and of a hydroxyl-containing compound which is different from the hydroxyl-containing compound used as reactant.
    Type: Grant
    Filed: May 8, 1998
    Date of Patent: November 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Detlef Kratz, Christoph Sigwart
  • Publication number: 20010016666
    Abstract: The present invention relates to a process for the preparation of esters from alcohols using acetic acid as acetylating agent and clays as catalysts, which comprises the preparation of esters in a single step from the reaction of aliphatic, acyclic, cyclic, heterocyclic, &agr;,&bgr;-unsaturated and aromatic alcohols with carbon atoms in the range of C1 to C10 with acetic acid in a molar ratio of 1:3 to 11 using reusable natural montmorillonite/metal ion-exchanged clay catalysts in the solvent medium of aliphatic, aromatic, or chlorinated hydrocarbons at 30-140° C. for a period in the range of 0.02 to 3.0 hrs, and recovering the corresponding esters by simple work-up procedure.
    Type: Application
    Filed: February 12, 1999
    Publication date: August 23, 2001
    Inventors: BOYAPATI MANORANJAN CHOUDARY, VELDURTHY BHASKAR, MANNEPALLI LAKSHMI KANTAM, KOTTAPALLI KOTESWARA RAO, KONDAPURAM RAGHAVAN
  • Patent number: 6232490
    Abstract: A method for the preparation of acetic acid and/or methyl acetate by isomerization of methyl formate in a reaction mixture which includes water, a solvent and a catalytic system containing a halogenated promoter and an iridium-based compound. Carbon monoxide is present in the reaction mixture at a partial pressure between 0.1.105 Pa and 25.105 Pa, methyl formate is maintained below 20% by weight of the reaction mixture and water is maintained in an amount which is at most 5% by weight of the reaction mixture. In a typical system, method formate isomerizes to acetic acid according to the reaction: HCOOCH3CH3COOH.
    Type: Grant
    Filed: September 23, 1998
    Date of Patent: May 15, 2001
    Assignee: Acetex Chimie
    Inventors: Carl Patois, Robert Perron, Daniel Thiebaut
  • Patent number: 6218536
    Abstract: 1,2-Bis-adducts of stable hindered nitroxide compounds with substituted ethylenes are prepared by reacting two equivalents of nitroxyl compound with an ethylenically unsaturated compound such as styrene or an acrylate ester. These adducts are very effective inhibitors to prevent the premature polymerization of ethylenically unsaturated monomers when such monomers are distilled, processed or stored.
    Type: Grant
    Filed: October 7, 1998
    Date of Patent: April 17, 2001
    Assignee: Ciba Specialty Chemcials Corporation
    Inventors: Glen Thomas Cunkle, Thomas F. Thompson, Volker H. von Ahn, Roland A. E. Winter
  • Patent number: 6184422
    Abstract: Compounds of formula I wherein X is C═CH2 or CH2; Y and Z are independently of each other hydrogen, fluorine or hydroxy; A is —C≡C—, —CH═CH— or —CH2—CH2—, R1 and R2 are independently of each other alkyl or perfluoroalkyl; and R3 is lower alkyl are useful in the treatment or prevention of hyperproliferative skin diseases, particularly psoriasis, basal cell carcinomas, disorders of keratinization and keratosis; or for reversing the conditions associated with photodamage.
    Type: Grant
    Filed: February 18, 1999
    Date of Patent: February 6, 2001
    Assignee: Hoffman-La Roche Inc.
    Inventors: Pierre Barbier, Franz Bauer, Peter Mohr, Marc Muller, Wolfgang Pirson
  • Patent number: 6180821
    Abstract: Acetic acid and/or vinyl acetate are produced by an integrated process in which a gaseous feedstock comprising ethylene and/or ethane and optionally steam is contacted in a first reaction zone (step (a)) with a molecular oxygen-containing gas in the presence of a catalyst active for the oxidation of ethylene to acetic acid and/or ethane to acetic acid and ethylene to produce a first product stream comprising acetic acid, water and ethylene (either as unreacted ethylene and/or as co-produced ethylene) and optionally also ethane, carbon monoxide, carbon dioxide and/or nitrogen.
    Type: Grant
    Filed: December 14, 1999
    Date of Patent: January 30, 2001
    Assignee: BP Chemicals Limited
    Inventors: Simon Jobson, Derrick John Watson
  • Patent number: 6177400
    Abstract: The compounds according to the general formula in which formula the dotted lines indicate a single or a double bond, n and m are 0 or 1, R1 is hydrogen or an acyl group —C(O)R3, R3 being a linear or branched alkyl or alkylene group from C1 to C8, the oxygen atom being bound to the adjacent &agr;-carbon atom by a double bond in the case where n is 0 and by a single bond in the case where n is 1, R2 is hydrogen or a linear or branched alkyl, alkenyl or alkoxy group from C1 to C8, or R2 is an alkenoxy group which is linked to the group R1 to form a 1,3-dioxolane cycle having 5 to 7 ring members, are useful perfuming ingredients. The most preferred compounds according to the invention are those which have a damascone- or damascenone-like structure, with the methyl substituent being in 4-position of the ring instead of the 2-position, as is the case in damascones and damascenones.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: January 23, 2001
    Assignee: Firmenich SA
    Inventors: Hubert Mimoun, Wolfgang Klaus Giersch
  • Patent number: 6130191
    Abstract: A process for the preparation of a mixture of trimethylolpropane caprylate and trimethylolpropane caprate comprising the steps ofA) purifying a less than pure mixture of methyl caprylate and methyl caprate;B) reacting the purified mixture from step A) with trimethylolpropane to transesterify the purified mixture to produce a reaction mixture containing trimethylolpropane caprylate and trimethylolpropane caprate; andC) removing methanol and unreacted methyl caprylate and methyl caprate from the reaction mixture.
    Type: Grant
    Filed: September 10, 1999
    Date of Patent: October 10, 2000
    Assignee: Henkel Corporation
    Inventors: Robert P. Ribelin, Stephen W. Turner
  • Patent number: 6114364
    Abstract: The present invention relates to a compound represented by the following general formula (1) ##STR1## (wherein X represents O, S, SO, SO.sub.2, or NH, Y is a substituted or unsubstituted hydrocarbon residue containing 1 through 6 carbon atoms and having an overall molecular weight of not less than 15 and not more than 400, and the hydrocarbon residue, when the residue is ring, may contain one or two hetero-atoms in the ring, and Z is a carboxyl group, a group derived therefrom or an aliphatic hydrocarbon residue having from 1 to 4 carbon atoms which may be substituted or unsabstituted) or a pharmacologically acceptable salt thereof (excluding (1R,2S)-2-[(2R)-(2-acetyl-amino-2-carboxyethyl)thiomethyl]-3-oxo-1-cyclope ntane-carboxylic acid (cystacyclin)), a method for production thereof and a medicinal use thereof. The compound of the present invention is useful as a neuron differentiation accelerator.
    Type: Grant
    Filed: October 5, 1998
    Date of Patent: September 5, 2000
    Assignee: Nippon Kayaku Co., Ltd.
    Inventors: Seiichi Saito, Tomio Morino, Kuniko Masuda
  • Patent number: 6103924
    Abstract: Preparation of 2,3,5-trimethylhydroquinone diesters by rearrangement of 2,6,6-trimethylcyclohex-2-ene-1,4-dione (4-oxo-isophorone, ketoisophorone) in the presence of a solid, acid catalyst and an acylating agent, for example carboxylic acid anhydrides or carboxylic acid halides. The 2,3,5-trimethylhydroquinone diester may then optionally be saponified to the free 2,3,5-trimethylhydroquinone, which is a valuable building block in the synthesis of vitamin E.
    Type: Grant
    Filed: April 21, 1999
    Date of Patent: August 15, 2000
    Assignee: Degussa-Huls AG
    Inventors: Nongyuan Shi, Mario Scholz, Steffen Hasenzahl, Horst Weigel, Bernd Drapal, Ralph McIntosh, Hans J. Hasselbach, Klaus Huthmacher
  • Patent number: 6087527
    Abstract: Method for producing an alkyl carboxylate, in which a carboxylic acid and an alcohol are esterified by reaction in the presence of an acid catalyst, by removing water in a dehydration step established halfway in the esterification reaction using a solid acid catalyst as the acid catalyst, and restarting the esterification reaction to complete the esterification reaction.
    Type: Grant
    Filed: September 21, 1998
    Date of Patent: July 11, 2000
    Assignees: Toray Industries, Inc., Soda Aromatic Co., Ltd.
    Inventors: Atsushi Niwa, Shinzo Imamura, Akio Hasebe, Ito Nobuhiko
  • Patent number: 6072077
    Abstract: 5-Z-octenyl esters of the formula ##STR1## in which R represents hydrogen, methyl or ethyl, have an intensive mango aroma, so that the compounds I can be added to fruit compositions and aroma compositions; they have flavor-intensifying and flavor-rounding action.
    Type: Grant
    Filed: June 5, 1997
    Date of Patent: June 6, 2000
    Assignee: Haarmann & Reimer, GmbH
    Inventors: Heinz-Jurgen Bertram, Matthias Guntert, Gunter Kindel
  • Patent number: 6057482
    Abstract: Benzyl alcohol of high purity is produced by supplying benzyl acetate, water and acetic acid to a hydrolysis reactor packed with a solid acid catalyst. The liquid reaction mixture produced, which contains benzyl acetate, water, benzyl alcohol and acetic acid, is supplied to an acetic acid-water recovery column, Benzyl alcohol and benzyl acetate are recovered while acetic acid is removed and returned to the hydrolysis reactor.
    Type: Grant
    Filed: November 9, 1998
    Date of Patent: May 2, 2000
    Assignee: Tosoh Corporation
    Inventors: Takashi Okada, Makoto Hanaya, Akitaka Hattori, Takanori Miyake, Nobuo Nagira, Shunya Ikumi, Takashi Hori, Norimasa Mizui
  • Patent number: 6046354
    Abstract: A novel glycerol derivative, a process for preparing the same, and a process for preparing a triazole derivative. An optically active 2-arylglycerol derivative which is novel and useful as a synthetic intermediate of medicament is provided, and furthermore, (R)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazole-1-yl)-propane-1,2-diol, which is useful as an antifungal agent, is prepared.
    Type: Grant
    Filed: August 31, 1998
    Date of Patent: April 4, 2000
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshihiko Yasohara, Kenji Miyamoto, Noriyuki Kizaki, Shigeru Kawano, Junzo Hasegawa
  • Patent number: 6040474
    Abstract: 1.
    Type: Grant
    Filed: April 6, 1998
    Date of Patent: March 21, 2000
    Assignee: BP Chemicals Limited
    Inventors: Simon Jobson, Derrick John Watson
  • Patent number: 6040475
    Abstract: This invention is concerned with the synthesis of 3-(1-acetoxy-1-methylethyl)-6-oxo-heptanal; 3-(1-acetoxy-1-methylethyl)-2-formyl-1-methyl-cyclopentanol; 5-[2-hydroxy-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclopentyl]-3-methyl- penta-2,4-dien-1-ol and 2,7,11-trimethyl-13-[2-hydroxy-5-(1-hydroxy-1-methylethyl)-2-methyl-cyclop entyl]-trideca-2,4,6,8,10,12-hexaenal which are useful as intermediates for the synthesis of lycopene metabolites.
    Type: Grant
    Filed: May 12, 1999
    Date of Patent: March 21, 2000
    Assignee: Roche Vitamins Inc.
    Inventors: Hanspeter Pfander, Bruno Traber
  • Patent number: 6018075
    Abstract: A process for the manufacture of a .gamma.-acetoxy-tiglic aldehyde by reacting a .gamma.-bromotiglic aldehyde or a .gamma.-chlorotiglic aldehyde with sodium acetate or potassium acetate in an organic solvent in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: May 12, 1999
    Date of Patent: January 25, 2000
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
  • Patent number: 6013834
    Abstract: A process for the production of vinyl acetate (VA) by reaction in the vapor phase of ethylene, oxygen and acetic acid as reactants, comprising passing at a temperature sufficient to initiate the reaction, a feed gas comprising said reactants and continuously or intermittently containing liquid acetic acid and/or non-volatile components, through a filter and distribution bed of inert material having throughout its volume substantial intercommunicating open spaces among the solid portions, and thence through a plurality of tubes each containing a bed of catalyst for the reaction, and withdrawing a product gas comprising VA. The filter and distribution bed acts to filter out the liquid acetic acid and/or non-volatile components and distribute more evenly the feed gas into the tubes.
    Type: Grant
    Filed: March 4, 1999
    Date of Patent: January 11, 2000
    Assignee: Celanese International Corporation
    Inventor: Philip M. Colling
  • Patent number: 5976202
    Abstract: Reaction products of polyolefins having predominantly a terminal double bond and a number average molecular weight of from 250 to 10,000, which possess an aliphatic hydrocarbon skeleton which is straight-chain or carries C.sub.1 -C.sub.4 -alkyl side chains, with from 1 to 10 mol, per equivalent of double bond, of one or more vinyl esters I ##STR1## are obtainable by reacting the stated polyolefins with the vinyl esters I in the presence of a free radical initiator at from 80 to 200.degree. C., it being possible for these reaction products subsequently to have been hydrolyzed to the corresponding alcohols or converted into the corresponding amines by reductive amination with amines II ##STR2## .
    Type: Grant
    Filed: July 20, 1995
    Date of Patent: November 2, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Peter Rath, Helmut Mach, Harald Schwahn, Hans-Joachim Muller, Wolfgang Reif, Thomas Ruhl
  • Patent number: 5973214
    Abstract: Both enantiomers of optically active 2-alkanol are produced by transesterification reaction of racemic 2-alkanol and aliphatic acid 2,2,2-trichloroethylester in the presence of enzyme derived from Candida antarctica.Both enantiomers of optically active 2-alkanol, which are useful as starting materials of liquid crystal materials and have optical purity of 99% or more, can be efficiently produced.
    Type: Grant
    Filed: September 16, 1998
    Date of Patent: October 26, 1999
    Assignee: Chisso Corporation
    Inventors: Naoyuki Yoshida, Hitoshi Yano
  • Patent number: 5962724
    Abstract: The present invention relates to a highly enantioselective process for the preparation of enantiomerically pure cyclopentane- and -pentene .beta.-amino acids of the general formula (I) ##STR1## in which A and L, A and D or E and L, D and E, R.sup.2, R.sup.3, T and R.sup.1 have the meaning given in the description.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: October 5, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Mittendorf, Hermann Arold, Peter Fey, Michael Matzke, Hans-Christian Militzer, Klaus-Helmut Mohrs
  • Patent number: 5958822
    Abstract: This invention concerns modified fluorosulfonic acid compounds possessing a sulfonic acid fluoride, chloride or ester group or a sulfonic acid or a salt of a sulfonic acid group at one end and respectively a hydrolyzable or hydrolyzed silane group at the other end, said sulfonic group being adjacent a substantially fluorinated bidentate hydrocarbylene group which is in turn adjacent to a hydrocarbylenegroup linked to said hydrolyzable or hydrolyzed silane group. Self-condensation of the latter compounds provides novel siloxanes and polysiloxanes. This invention further concerns novel composites comprising a metal oxide network having incorporated therein a group having the formula: --O).sub.q Si(OH).sub.n-q R.sup.1.sub.m R.sup.2 R.sub.f SO.sub.3 Q, and compositions comprising a solid material having a reactive surface to which surface is attached at least one group having the formula: --O).sub.q Si(OH).sub.n-q R.sup.1.sub.m R.sup.2 R.sub.f SO.sub.3 Q.
    Type: Grant
    Filed: March 16, 1998
    Date of Patent: September 28, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Richard Beckerbauer, Mark Andrew Harmer, Qun Sun
  • Patent number: 5932761
    Abstract: It is provided a process for industrially advantageously producing a branched aldehyde represented by the formula; ##STR1## ?wherein Y represents an acyl group of two or more carbon atoms; and X represents an acyloxymethyl group represented by --CH.sub.2 OY' (where Y' represents an acyl group of two or more carbon atoms), cyano group or an alkoxycarbonyl group! which is useful as an intermediate for pharmaceuticals and agricultural chemicals, comprising subjecting an olefinic compound represented by the following formula; ##STR2## (wherein Y and X are the same as defined above), to the reaction with hydrogen and carbon monoxide in the presence of a rhodium compound and a tertiary organic phosphorus compound with an electronic parameter (.upsilon.-value) of 2080 to 2090 cm.sup.-1 or with a steric parameter (.theta.-value) of 150 to 180.degree..
    Type: Grant
    Filed: March 23, 1998
    Date of Patent: August 3, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Toshihiro Omatsu, Masahiko Kitayama, Takashi Onishi
  • Patent number: 5908956
    Abstract: This method provides trimethylhydroquinone diester by using a recyclable catalyst which shows high activity and operability in the reaction, while reducing the risk of corrosion of the reactor. The method for the production of 2,5,6-trimethylhydroquinone diester comprises reacting 2,6,6-trimethylcyclohexe-2-en-1,4-dione with an acylating agent in the presence of a solid catalyst. The acylating agent includes a C.sub.2-4 carboxylic acid anhydride (e.g. acetic anhydride) and a C.sub.2-4 carboxylic acid halide (e.g. acetyl chloride). The solid catalyst includes a solid acid catalyst (e.g. strongly or super-strongly acidic ion exchange resin, compound oxide, zeolite, heteropoly acid).
    Type: Grant
    Filed: December 17, 1997
    Date of Patent: June 1, 1999
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Ikuo Takahashi, Masahiro Chikamori
  • Patent number: 5891921
    Abstract: Wood preservative systems comprising (a) a biocidal effective amount of (i) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium carboxylate having the formula ##STR1## wherein R.sup.1 and R.sup.2 are a C.sub.8 -C.sub.12 alkyl group; R.sup.3 is a substituted or unsubstituted, interrupted or uninterrupted C.sub.1 -C.sub.100 group; l and q independently are 1, 2 or 3 and (l) (q) is 1, 2, or 3; and n is 0 or an integer from 1 to 50; (ii) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium borate having the formula ##STR2## wherein R.sup.1 and R.sup.2 are defined as above, and a is 2 or 3, but when a is 2, b is 0 or 1, and when a is 3, b is 0, 1, or 2; or (iii) a combination of (i) and (ii); and (b) a solvent are provided. These carboxylate quats as well as carboxylate quats wherein R.sup.1 is a C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group and R.sup.2 is a C.sub.8 -C.sub.20 alkyl group are preferably prepared by an indirect or a direct synthesis.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: April 6, 1999
    Assignee: Lonza Inc.
    Inventor: Leigh E. Walker
  • Patent number: 5892104
    Abstract: This invention relates to a compound having the formula I: ##STR1## wherein n is an integer of from 0 to 1; when n is 1, one of dashed lines a and b is a single bond and the other of dashed lines a and b is a double bond, dashed line c is not present, and dashed line d is a single bond; when n is 0, dashed lines a, b, c and d are single bonds or one of dashed lines a and b is a single bond and the other of dashed lines a and b is a double bond, dashed line c is not present, and dashed line d is a double bond; R.sub.1, R.sub.2 and R.sub.3 are, independently, lower branched or straight chain alkyl, alkenyl or alkynyl of C.sub.1 -C.sub.6 ; and R.sub.4 is hydrogen, lower branched or straight chain alkyl, alkenyl or alkynyl of C.sub.1 -C.sub.5, or C(O)R.sub.5, wherein R.sub.5 is hydrogen or lower branched or straight chain alkyl, alkenyl or alkynyl of C.sub.1 -C.sub.4 ; wherein the sum of the carbon atoms in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is less than or equal to eight carbon atoms.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: April 6, 1999
    Assignee: Millenium Specialty Chemicals, Inc.
    Inventors: Bernard J. Kane, Henri M. Hoffmann
  • Patent number: 5880311
    Abstract: Catalyst particles are contacted with a liquid and a gas in a vertically extending cylindrical vessel. The particles and liquid are placed in the vessel into which the gas and liquid are continuously fed from the bottom thereof so that an upwardly flowing mixture comprising the particles, liquid and gas is formed. The mixture is introduced into a gas separating zone disposed adjacent to an upper portion of the vessel to separate the mixture by gravity into a gas phase, a supernatant liquid phase and a phase rich in the catalyst particles. The gas and supernatant phases are continuously withdrawn from the separating zone while the catalyst particles-rich phase is continuously recycled to the bottom of the vessel by gravity.
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: March 9, 1999
    Assignee: Tonen Corporation
    Inventors: Fumihiko Uemura, Hideki Sugiyama, Chieko Nagasawa, Takeshi Minami, Kazuhiko Hamato, Noriyuki Yoneda, Akihisa Yamaguchi
  • Patent number: 5874611
    Abstract: A hydroquinone derivative (I) represented by the following formula: ##STR1## wherein R.sup.1 is a hydrogen atom, acetyl group or benzoyl group, such hydroquinone derivative being useful as an intermediate for chroman derivatives useful as a blood sugar-lowering agent.
    Type: Grant
    Filed: July 1, 1996
    Date of Patent: February 23, 1999
    Assignee: Eisai Chemical Co., Ltd.
    Inventors: Kimio Hamamura, Chiaki Seki, Masayuki Konishi
  • Patent number: 5869739
    Abstract: Formic acid or derivatives thereof are produced from non-toxic carbon dioxide in the supercritical state, using it as raw materials, without using solvents, and at a high efficiency owing to a high reaction velocity, by reacting said carbon dioxide and an active hydrogen group-containing compound.
    Type: Grant
    Filed: November 20, 1996
    Date of Patent: February 9, 1999
    Assignees: Research Development Corporation of Japan, NKK Corporation
    Inventors: Takao Ikariya, Philip Gregory Jessop, Yi Hsiao, Ryoji Noyori
  • Patent number: 5866710
    Abstract: A process for the preparation of an ester comprises carrying out an esterification in the presence of a catalyst comprising the reaction product of an orthoester or a condensed orthoester of titanium or zirconium, an alcohol containing at least two hydroxyl groups, a 2-hydroxy acid and a base. The process can be a direct esterification or a transesterification and can be a polyesterification. The catalyst can effectively produce esters without leading to a haze in the final product and there is a reduced amount of yellowing of polyesters in comparison to known catalysts.
    Type: Grant
    Filed: June 5, 1997
    Date of Patent: February 2, 1999
    Assignee: Tioxide Specialties Limited
    Inventors: John Ridland, Iain Wesley Hepplewhite, Brian Steven Jolly