Preparing Esters From Aldehydes Patents (Class 560/238)
  • Patent number: 10934245
    Abstract: The invention relates to a process for preparing a carboxylic ester by reacting an aldehyde in the presence of an aluminum alkoxide, wherein the aluminum alkoxide is obtained either by reacting an aluminum hydride with an aldehyde or by reacting a different aluminum alkoxide with a carboxylic ester.
    Type: Grant
    Filed: May 14, 2018
    Date of Patent: March 2, 2021
    Assignee: EVONIK OPERATIONS GMBH
    Inventors: Alexander Lygin, Steffen Krill, Matthias Grömping, Andreas Tepperis
  • Patent number: 10407626
    Abstract: Scavenging compounds and compositions useful in applications relating to the production, transportation, storage, and separation of municipal waste water, hydrocarbons, crude oil, and natural gas among others are disclosed. Also disclosed herein are methods of using the compounds and compositions as scavengers, particularly in applications relating to the production, transportation, storage, and separation of hydrocarbons, crude oil, and natural gas.
    Type: Grant
    Filed: August 12, 2016
    Date of Patent: September 10, 2019
    Assignee: ECOLAB USA INC.
    Inventors: Geeta Rana, Christopher Thomas Burrell
  • Publication number: 20150148360
    Abstract: The present invention provides novel compounds of Formula (I), and pharmaceutically compositions thereof. Compounds of Formula (I) are inhibitors of histone deacetylases (HDACs) and 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase (HMGR). Also provided are methods of using the compounds and pharmaceutical compositions for inhibiting the activity of HDACs and HMGR, treating diseases associated with HDACs or HMGR (e.g., cancer, hypercholesterolemia, an acute or chronic inflammatory disease, autoimmune disease, allergic disease, pathogen infection, neurodegenerative disease, and a disease associated with oxidative stress), or inhibiting drug resistance of cancer cells.
    Type: Application
    Filed: July 19, 2013
    Publication date: May 28, 2015
    Inventors: Jung-Hsin Lin, Jim-Min Fang, Ting-Rong Chen, Jhih-Bin Chen, Ching-Chow Chen, Tzu-Tang Wei
  • Publication number: 20140378699
    Abstract: The present invention relates to an improved process for the preparation of Fesoterodine and pharmaceutically acceptable salts thereof. The present invention particularly relates to a process for the preparation of Fesoterodine from O-benzyl tolterodine.
    Type: Application
    Filed: January 4, 2013
    Publication date: December 25, 2014
    Inventors: Venkat Raman Jayaraman, Samir Patel, Indrajit Thakor, Viral Maheshbhai Parekh, Mahesh Ladani, Chetan Patil, Ronak Patel, Prashant Raval
  • Publication number: 20140213788
    Abstract: The present invention relates to a process for the preparation of a compound of the general Formula (I), comprising: a) reacting a compound of the general Formula (II) with a compound of the Formula III R2COOH and a compound of the general Formula IV R3NC under such conditions that compound I is formed, wherein R1 represents a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R2 represents a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R3 represents a substituted or unsubstituted alkyl, alkenyl, or alkynyl structure. In further aspect the subject invention relates to the use of the the obtained products as intermediates for various peptidomimetics, and preferably as a building block in a convergent synthesis of prolyl dipeptide structures.
    Type: Application
    Filed: March 28, 2014
    Publication date: July 31, 2014
    Applicant: Vereniging voor Christelijk hoger onderwijs, wetenschappelijk onderzoek en patiëntenzorg
    Inventors: Eelco RUIJTER, Romano ORRU, Anass ZNABET, Marloes POLAK, Nicholas TURNER
  • Patent number: 8686145
    Abstract: The present invention relates to a process for the preparation of a compound of the general Formula (I), comprising: a) reacting a compound of the general Formula (II) with a compound of the Formula III R2COOH and a compound of the general Formula IV R3NC under such conditions that compound I is formed, wherein R1 represents a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R2 represents a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R3 represents a substituted or unsubstituted alkyl, alkenyl, or alkynyl structure. In further aspect the subject invention relates to the use of the obtained products as intermediates for various peptidomimetics, and preferably as a building block in a convergent synthesis of prolyl dipeptide structures.
    Type: Grant
    Filed: September 16, 2010
    Date of Patent: April 1, 2014
    Assignee: Vereniging Voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek en Patientenzorg C/O Technology Transfer Officer VU & Vumc
    Inventors: Eelco Ruijter, Romano Orru, Anass Znabet, Marloes Polak, Nicholas Turner
  • Publication number: 20130211033
    Abstract: The present invention relates to a process for synthesizing a multifunctional compound, including the reaction of a compound of formula (II) with atmospheric or molecular oxygen, in the presence of at least one aldehyde of formula (III), and optionally in the presence of at least one catalyst or at least one radical initiator; wherein: R10, R20, R30, R40, R50, L2, R60, R7, R8, and R9 are as described in the claims. The invention also relates to the use of these compounds as monomers for the preparation of polyurethane. The invention also relates to the use of these compounds as monomers of polymers or of biopolymers.
    Type: Application
    Filed: October 27, 2011
    Publication date: August 15, 2013
    Applicants: MEURICE R&D ASBL, UNIVERSITE DE POITIERS, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
    Inventors: Stefano Casciato, Yannick Pouilloux, Vincent Dubois
  • Publication number: 20130150611
    Abstract: The present invention relates to a process for producing a carboxylic acid ester, comprising a step of oxidizing an aldehyde by mixing an alcohol, carbon dioxide, the aldehyde and at least one compound selected from the group consisting of compounds represented by the formulae (2-1) and (2-2): wherein R2 represents an alkyl group optionally having a substituent or the like; R3 and R4 each independently represents an alkyl group optionally having a substituent or the like or R3 and R4 are linked together to form a divalent hydrocarbon group optionally having a substituent or the like; Y represents a group of —S— or a group of —N(R5)—, wherein R5 represents an alkyl group optionally having a substituent or the like, or R5 is linked to R4 to form a divalent hydrocarbon group optionally having a substituent; and R8 represents an alkyl group.
    Type: Application
    Filed: August 25, 2011
    Publication date: June 13, 2013
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Koji Hagiya
  • Patent number: 8461373
    Abstract: Disclosed is a catalyst for use in production of carboxylic acid ester by reacting (a) aldehyde and alcohol, or (b) one or more types of alcohols, in the presence of oxygen; wherein oxidized nickel and X (wherein X represents at least one element selected from the group consisting of nickel, palladium, platinum, ruthenium, gold, silver and copper) are loaded onto a support within the range of the atomic ratio of Ni/(Ni+X) of from 0.20 to 0.99.
    Type: Grant
    Filed: July 31, 2008
    Date of Patent: June 11, 2013
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Ken Suzuki, Tatsuo Yamaguchi
  • Patent number: 8450235
    Abstract: A supported composite particle material comprises: a composite particle formed of an oxidized nickel and X (wherein X represents at least one of elements selected from the group consisting of nickel, palladium, platinum, ruthenium, gold, silver and copper); and a support on which the composite particle is supported, the supported composite particle material having a supported layer in which the composite particle is localized.
    Type: Grant
    Filed: October 23, 2008
    Date of Patent: May 28, 2013
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Ken Suzuki, Tatsuo Yamaguchi
  • Publication number: 20120330015
    Abstract: The present invention relates to a process for the preparation of a compound of the general Formula (I), comprising: a) reacting a compound of the general Formula (II) with a compound of the Formula III R2COOH and a compound of the general Formula IV R3NC under such conditions that compound I is formed, wherein R1 represents a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R2 represents a substituted or unsubstituted alkyl, alkenyl, alkynyl, aromatic or non-aromatic, mono-, di- or tricyclic, or heterocyclic structure, and R3 represents a substituted or unsubstituted alkyl, alkenyl, or alkynyl structure. In further aspect the subject invention relates to the use of the obtained products as intermediates for various peptidomimetics, and preferably as a building block in a convergent synthesis of prolyl dipeptide structures.
    Type: Application
    Filed: September 16, 2010
    Publication date: December 27, 2012
    Applicant: Vereniging voor Christelijk hoger onderwijs, wetenschappelijk onderzoek en patientenzorg
    Inventors: Eelco Ruijter, Romano Orru, Anass Znabet, Marloes Polak, Nicholas Turner
  • Publication number: 20120225020
    Abstract: This disclosure provides choline analogs comprising the following structure: where each R1 independently is H or isotopically enriched D, R2 is a protecting group, and N is 14N or isotopically enriched 15N. This disclosure also provides methods of making choline analogs, which include performing a protection step on a betaine aldehyde to form a choline analog, and methods of using choline analogs to form hyperpolarized compounds.
    Type: Application
    Filed: February 24, 2012
    Publication date: September 6, 2012
    Inventors: Eduard Y. Chekmenev, Roman V. Shchepin
  • Publication number: 20110251422
    Abstract: The disclosure relates to a process for the preparation of acetic acid. The process comprises reacting a decanter heavy, organic phase of an acetic acid production process with acetic anhydride to convert acetaldehyde in the decanter heavy, organic phase to ethylidene diacetate and separating it from the decanter heavy, organic phase. Ethylidene diacetate can be hydrolyzed to recover acetic acid.
    Type: Application
    Filed: April 7, 2010
    Publication date: October 13, 2011
    Inventor: Brian A. Salisbury
  • Publication number: 20110184206
    Abstract: Disclosed is a catalyst for use in production of carboxylic acid ester by reacting (a) aldehyde and alcohol, or (b) one or more types of alcohols, in the presence of oxygen; wherein oxidized nickel and X (wherein X represents at least one element selected from the group consisting of nickel, palladium, platinum, ruthenium, gold, silver and copper) are loaded onto a support within the range of the atomic ratio of Ni/(Ni+X) of from 0.20 to 0.99.
    Type: Application
    Filed: July 31, 2008
    Publication date: July 28, 2011
    Inventors: Ken Suzuki, Tatsuo Yamaguchi
  • Publication number: 20100256413
    Abstract: Method for the chemical synthesis of capsinoids, natural compounds with proven biological activity, from vanillin, comprising the protection of the alcohol group thereof, reduction of the aldehyde to alcohol, esterification of same and deprotection of the first protected alcohol group. In this way, the desired compounds are generated with high purity and said compounds can be easily separated with no mixing owing to the competitive esterification on the aromatic ring.
    Type: Application
    Filed: April 11, 2008
    Publication date: October 7, 2010
    Applicant: UNIVERSIDAD DE CÁDIZ
    Inventors: José María González Molinillo, Francisco Antonio Macías Dominguez, Rosa María Varela Montoya, Miguel Palma Lovillo, Carmelo García Barroso, Gerardo Fernández Barbero
  • Publication number: 20100240616
    Abstract: Omega-3 lipid compounds of the general formula (I): wherein R1 and R2 are the same or different and are chosen from a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, a carboxy group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; P represents a hydrogen atom, (Formula II) wherein P2, P3, and P4 are chosen from a hydrogen atom, an alkyl group, and a C14-C22 alkenyl group, wherein the alkyl and alkenyl groups are optionally substituted with a hydroxy group, (Formula III), (Formula IV), or (Formula V); and Y is a C14-C22 alkenyl group with at least one double bond, having E and/or Z configuration; or any pharmaceutically acceptable complex, solvate, salt or pro-drug thereof, with the proviso that R1 and R2 are not simultaneously a hydrogen atom.
    Type: Application
    Filed: November 1, 2007
    Publication date: September 23, 2010
    Inventors: Anne Kristin Holmeide, Jenny Rosman
  • Patent number: 7696125
    Abstract: A catalyst and a process for preparing carboxylic acid esters from an aldehyde and an alcohol in the presence of molecular oxygen are disclosed. The catalyst comprises metals supported on a silica-containing support, wherein the metals consist essentially of palladium, lead, an alkali or alkaline earth metal, and at least one of niobium and zirconium. The process for preparing a carboxylic acid ester comprises reacting an aldehyde with an alcohol in the presence of molecular oxygen and the aforementioned catalyst.
    Type: Grant
    Filed: July 6, 2005
    Date of Patent: April 13, 2010
    Assignee: Lee Chang Yung Chemical Industry Corporation
    Inventors: Kindtoken Hwaider Liu, Man-Yin Lo, Wen-Chyi Lin, Mei-Yuan Chang
  • Patent number: 7091155
    Abstract: A catalyst for ester production which comprises zirconium oxide, copper, and at least one oxide selected from the group consisting of zinc oxide, chromium oxide, aluminum oxide and silicon oxide, and is obtainable by reducing with hydrogen a catalyst precursor prepared by the reaction of a salt containing at least one of metals constituting the oxides, a zirconium salt and a copper salt with an alkali hydroxide; and a process for producing an ester which comprises bringing either an alcohol or an alcohol and an aldehyde into contact with this catalyst in a gas phase.
    Type: Grant
    Filed: November 15, 2002
    Date of Patent: August 15, 2006
    Assignee: Chisso Corporation
    Inventors: Kanichiro Inui, Takayoshi Takahashi, Toru Kurabayashi
  • Patent number: 6809217
    Abstract: Ethanol is dehydrogenated in the presence of hydrogen over a dehydrogenation catalyst, for example, a copper on silica catalyst. The liquefiable products present in the resulting intermediate reaction product mixture are selectively hydrogenated over a suitable catalyst, such as 5% ruthenium on carbon, so as selectively to hydrogenate reactive carbonyl-containing by-products to the corresponding alcohols. Butan-2-one and n-butyraldehyde are thereby hydrogenated to 2-butanol and n-butanol respectively. A two stage distillation procedure is then used to purify the selectively hydrogenated product. A first distillate of ethyl acetate, ethanol and water produced in the first distillation zone is redistilled in the second distillation zone, thereby producing a bottom product comprising, typically, from about 99.8 mol % to about 99.
    Type: Grant
    Filed: June 5, 2001
    Date of Patent: October 26, 2004
    Assignee: Davy Process Technology Limited
    Inventors: Stephen William Colley, Christopher Richard Fawcett, Colin Rathmell, Michael William Marshall Tuck
  • Publication number: 20040192958
    Abstract: The present invention describes a process for preparing an enol ester of a 4-halo-butyraldehyde which comprises contacting a cyclopropane carboxaldehyde (CPCA) and a carboxylic acid halide in the presence of a Lewis acid catalyst. In addition, the present invention relates to a process for preparing an acetal of a 4-halo-butyraldehyde which comprises contacting an enol ester of a 4-halo-butyraldehyde, prepared according to the present invention, with an alcohol in the presence of a certain acid catalyst.
    Type: Application
    Filed: March 25, 2003
    Publication date: September 30, 2004
    Inventor: John Anthony Hyatt
  • Patent number: 6767923
    Abstract: Benzhydryl derivatives of the formula I, where the index and the variables are as defined below: X is oxygen or sulfur; R1, R3 are halogen, cyano, nitro, hydroxyl, mercapto, amino, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylcarbonyloxy, formyloxy, alkylthio, alkenylthio, alkynylthio, alkylamino, dialkylamino, alkylcarbonyl or formyl, where the carbon atoms in the radicals mentioned may be partially or fully halogenated; R2 is halogen, cyano, nitro, hydroxyl, mercapto, amino, alkyl, alkoxy, haloalkyl or haloalkoxy, where the groups R2 may be different if n=2; R4 is alkyl, alkenyl or alkynyl, where the carbon atoms in these radicals may be unsubstituted or partially or fully halogenated; R5, R6 are hydroxyl, alkyl, alkenyl, haloalkyl, haloalkenyl, alkoxy, alkenyloxy, haloalkoxy, haloalkenyloxy, cycloalkyl, cycloalkylalkyl, cycloalkoxy or cycloalkylalkoxy; n is 0, 1 or 2; processes for preparing the compounds I, compositions comprising them and their use for con
    Type: Grant
    Filed: October 29, 2002
    Date of Patent: July 27, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Ingo Rose, Jordi Tormo i Blasco, Markus Gewehr, Wassilios Grammenos, Bernd Müller, Joachim Rheinheimer, Peter Schäfer, Frank Schieweck, Thomas Grote, Andreas Gypser, Eberhard Ammermann, Gisela Lorenz, Reinhard Stierl, Siegfried Strathmann, Paul Carter, Jürgen Curtze
  • Patent number: 6696594
    Abstract: A process for the conversion of aldehydes to esters, specifically acrolein or methacrolein to methyl acrylate or methyl methacrylate, respectively. Essentially in the absence of water, an aldehyde is contacted with an oxidizing agent to form an intermediate and then the intermediate is contacted with a diol or an alcohol to form an ester or diester. Preferably, the oxidizing agent is also a chlorinating agent. Specifically, acrolein or methacrolein is contacted with an oxidizing/chlorinating agent, such as t-butyl hypochlorite, and the chlorinated compound is contacted with an alcohol, such as methanol, to form methyl acrylate or methyl methacrylate, respectively. Generally, the order of addition is for the oxidizing agent to be added to the aldehyde, specifically for t-butyl hypochlorite to be added to acrolein or methacrolein, and for the diol or alcohol to be added to the intermediate, specifically for the methanol to be added to the reaction product of acrolein or methacrolein and t-butyl hypochlorite.
    Type: Grant
    Filed: May 13, 2002
    Date of Patent: February 24, 2004
    Assignee: Saudi Basic Industries Corporation
    Inventors: Andrew T. Au, Jean-Pierre Lawanier, David Adam Flosser
  • Publication number: 20030216587
    Abstract: A process for the conversion of aldehydes to esters, specifically acrolein or methacrolein to methyl acrylate or methyl methacrylate, respectively. Essentially in the absence of water, an aldehyde is contacted with an oxidizing agent to form an intermediate and then the intermediate is contacted with a diol or an alcohol to form an ester or diester. Preferably, the oxidizing agent is also a chlorinating agent. Specifically, acrolein or methacrolein is contacted with an oxidizing/chlorinating agent, such as t-butyl hypochlorite, and the chlorinated compound is contacted with an alcohol, such as methanol, to form methyl acrylate or methyl methacrylate, respectively. Generally, the order of addition is for the oxidizing agent to be added to the aldehyde, specifically for t-butyl hypochlorite to be added to acrolein or methacrolein, and for the diol or alcohol to be added to the intermediate, specifically for the methanol to be added to the reaction product of acrolein or methacrolein and t-butyl hypochlorite.
    Type: Application
    Filed: May 13, 2002
    Publication date: November 20, 2003
    Applicant: Saudi Basic Industries Corporation (SABIC)
    Inventors: Andrew T. Au, Jean-Pierre Lawanier, David Adam Flosser
  • Patent number: 6632959
    Abstract: A base catalyst, obtained by formulating at least one alkali metal compound selected from the group consisting of alkoxides, hydroxides and oxides of alkali metals and an alkaline-earth metal oxide in a ratio of “the weight of alkaline metal compound/the weight of alkaline-earth metal oxide”=0.005 to 1, is used in a reaction of an aldehyde to produce a glycol monoester, thereby providing a base catalyst with an improved efficiency which can be applied to aldol reaction or the like and which has high activity to give target product in a high selectivity.
    Type: Grant
    Filed: February 7, 2000
    Date of Patent: October 14, 2003
    Assignee: Chisso Corporation
    Inventors: Kan-ichiro Inui, Shunji Oshima, Toru Kurabayashi, Sakae Kawamura, Masahiro Yokota
  • Publication number: 20030060655
    Abstract: It is an object of the present invention to provide a catalyst for manufacturing a carboxylic ester, which has superior catalytic activity. The present invention relates to a catalyst for preparing a carboxylic ester, used in a) a reaction for preparing a carboxylic ester by reacting oxygen, an aldehyde, and an alcohol, or b) a reaction for manufacturing a carboxylic ester by reacting oxygen and one or more types of alcohol, comprising a carrier and 1) ultrafine gold particles and/or 2) ultrafine metal particles containing gold and a second element other than gold, having an average particle diameter of not more than 6 nm, are supported on the carrier.
    Type: Application
    Filed: June 3, 2002
    Publication date: March 27, 2003
    Inventors: Toshio Hayashi, Takahiro Inagaki
  • Publication number: 20030060571
    Abstract: Monofunctional polyfluorooxetane oligomers and polymers are prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. The fluorooxetane oligomers or polymers can be copolymerized with generally cyclic ethers. Alternatively, the polyfluorooxetane oligomer or polymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties that have previously been provided by migratory chemicals such as waxes and oils.
    Type: Application
    Filed: March 28, 2002
    Publication date: March 27, 2003
    Applicant: OMNOVA Solutions Inc.
    Inventors: Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson, Robert E. Medsker
  • Patent number: 6362344
    Abstract: Chiral aminoalcohol catalysts and methods for their preparation are provided. The first catalyst is prepared via selective hydrogenation of one of two benzene rings in a precursor. The aminoalcohol promotes the asymmetric addition of organozinc reagents to aldehydes to afford optically active alcohols or their esters. The second catalyst is prepared by selective dialkylation of 3-exo-aminoisoborneol with a 2-haloethyl ether. The aminoalcohol promotes the addition of organozinc reagents to aliphatic aldehydes containing a &bgr;-branch with greatly enhanced enantioselectivity relative to DAIB.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: March 26, 2002
    Assignee: Bristol-Myers Squibb Pharma Company
    Inventor: William A. Nugent
  • Patent number: 6316663
    Abstract: A new ligands that include a benzene ring in the backbone can be combined with a metal or metal precursor compound or formed into a metal-ligand complex catalyze a number of different chemical transformations, including olefin polymerization reactions. The ligands, complexes formed with the ligands and compositions including the ligands are useful catalysts, depending on the reaction.
    Type: Grant
    Filed: March 21, 2001
    Date of Patent: November 13, 2001
    Assignee: Symyx Technologies, Inc.
    Inventors: Anil Guram, Cheryl Lund, Howard W. Turner, Tetsuo Uno
  • Patent number: 6248920
    Abstract: Process for the quantitative preparation of esters, with a high yield, which comprises reacting an aldehyde or ketone compound and an acid halide compound in a one pot reaction in the presence of at least one compound represented by the following formulae: RMgX   (I); RMgX/CuX   (II); and RLi or R(CuLi)½  (III); in which R represents a hydrocarbon group, and X represents a halogen atom. Production processes of a resist material and a semiconductor device are also disclosed.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: June 19, 2001
    Assignee: Fujitsu Limited
    Inventors: Satoshi Takechi, Tadashi Kikukawa
  • Patent number: 6215020
    Abstract: The invention is a base-modified clay that selectively catalyzes the formation of a glycol monoester from an aldehyde. The base-modified clay comprises a clay having secluded conjugate base sites and exchangeable interstitial cationic spaces. In the base-modified clay, the interstitial hydroxyl groups have been converted to oxide sites, at least one structural hydroxyl group has been converted to an oxide site. The base-modified clay contains sufficient conjugate base cations to balance the charge of said oxide groups. Processes for preparing the base-modified clay are described. The invention also provides a process for preparing a glycol monoester. This process includes heating in a reaction vessel an aldehyde and a catalytic amount of the base-modified clay under conditions sufficient to produce a glycol monoester.
    Type: Grant
    Filed: June 30, 1999
    Date of Patent: April 10, 2001
    Assignee: Eastman Chemical Company
    Inventors: William A. Beavers, Robert D. Culp
  • Patent number: 6111135
    Abstract: Disclosed is a process for manufacturing an ester of 1,3-propanediol, comprising, contacting at a temperature of about 0.degree. C. to about 250.degree. C., ethylene, formaldehyde or a form of formaldehyde, a carboxylic acid, and a compound of the formula MZ.sub.n.Q.sub.t, wherein:M is a zirconium[IV], cobalt[II], vanadium[IV], bismuth[II], tin[II], a rare earth metal, scandium or yttrium;n is the oxidation state of M;at least one of Z is an anion of the formula R.sup.1 SO.sub.3.sup.- or R.sup.1 CO.sub.2.sup.-, wherein R.sup.1 is hydrocarbyl or substituted hydrocarbyl containing 1 to 20 carbon atoms or part of a polymer, and the remainder of Z is oxo or one or more monovalent anions;Q is a neutral ligand; andt is 0 or an integer of 1 to 12.
    Type: Grant
    Filed: December 2, 1998
    Date of Patent: August 29, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Douglas J. Adelman, Neville Everton Drysdale
  • 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: 6040472
    Abstract: Disclosed is a novel catalyst for use in producing a carboxylic ester from an aldehyde, an alcohol and molecular oxygen, which comprises a carrier having supported thereon Pd and Pb in a Pd/Pb atomic ratio (S) of 3/0.7.ltoreq.S.ltoreq.3/1.3, and which exhibits a maximum intensity peak at a diffraction angle (2.theta.) in the range of from 38.55.degree. to 38.70.degree. in a powder X-ray diffraction pattern thereof, wherein the peak is ascribed to the (111) crystal face diffraction of a Pd--Pb intermetallic compound.
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: March 21, 2000
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Setsuo Yamamatsu, Tatsuo Yamaguchi, Koshiro Yokota
  • Patent number: 6018074
    Abstract: A process for the preparation of polyalcohols comprises the stages:(a) Reaction of an alkanal or ketone with formaldehyde in aqueous solution in the presence of a tertiary amine, to form a formates containing polyalcohol product mixture,(b) removal of water, excess tertiary amine, excess formaldehyde(c) heating of remaining mixture from (b) with removal of further formaldehyde and tertiary amine with formation of the formates of the polyalcohol,(d) transfer of tertiary amine removed from stage (b) and/or from stage (c), to synthesis stage (a) and/or to the subsequent transesterification stage (e),(e) transesterification of the resulting formates of the polyalcohol from stage (c) with an alcohol of the formula ROH in the presence of a transesterification catalyst to give polyalcohols and formates of the formula ##STR1## where R is a hydrocarbon radical, preferably alkyl of 1-6, particularly preferably 1-2, carbon atoms, and(f) isolation of the polyalcohols.
    Type: Grant
    Filed: October 5, 1998
    Date of Patent: January 25, 2000
    Assignee: BASF Aktiengesellshcaft
    Inventors: Detlef Kratz, Achim Stammer, Tom Witzel, Martin Brudermuller
  • 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: 5892102
    Abstract: A catalyst for the production of carboxylic acid esters for use in reacting an aldehyde with an alcohol in a liquid phase in the presence of molecular oxygen, comprising calcium carbonate and palladium, bismuth and at least one element selected from the group consisting of barium, iron, zinc and germanium, these elements being supported on said calcium carbonate.
    Type: Grant
    Filed: July 30, 1997
    Date of Patent: April 6, 1999
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Yuji Mikami, Akio Takeda, Motomu Oh-Kita
  • Patent number: 5821384
    Abstract: Disclosed is a process for making vinyl carboxylate esters such as vinyl acetate and vinyl propionate, by a reactive distillation process comprising a reaction zone wherein a vinyl carboxylate ester is formed from a carbonyl compound selected from aliphatic aldehydes and ketones and an anhydride of an aliphatic carboxylic acid and a distillation zone from which the vinyl carboxylate ester is recovered and substantially separated from other compounds contained within the column. The process requires significantly less equipment than known, analogous processes and thus the cost of constructing a plant for the operation of the present process is substantially reduced.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: October 13, 1998
    Assignee: Eastman Chemical Company
    Inventors: Joseph Robert Zoeller, Donald Wayne Lane, Eleanor Hawkins Cwirko, Dewey Wayne Fuller, Jr., Scott Donald Barnicki
  • Patent number: 5770762
    Abstract: Described is a process for producing a 4-substituted-2-butenal represented by the following formula (1); ##STR1## (wherein X represents an acyloxy group or halogen atom; R represents hydrogen atom, an aliphatic hydrocarbon group or an aromatic hydrocarbon group; and these hydrocarbon groups can be substituted with hydroxyl group, an alkoxy group, an aryloxy group, an acyl group or an alkoxycarbonyl group), which is useful as synthetic intermediates of phormaceutieals, agricultural chemicals and the like,comprising subjecting a substituted acetaldehyde represented by the following formula (2);X--CH.sub.2 --CHO (2)(wherein X has the same meaning as defined above), with an aldehyde represented by the following formula (3);R--CH.sub.2 --CHO (3)(wherein R has the same meaning as defined above) in the presence of an amino carboxylic acid.
    Type: Grant
    Filed: April 22, 1997
    Date of Patent: June 23, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideharu Iwasaki, Takashi Onishi
  • Patent number: 5744637
    Abstract: This invention pertains to accelerating the rate of formation of 1,1-dicarboxylic esters from the reaction of an aldehyde with a carboxylic acid anhydride or a ketene in the presence of a non-iodide containing a strong Bronsted acid catalyst by the addition of a carboxylic acid at about one bar pressure and between about 0.degree. and 80.degree. C. in the substantial absence of a hydrogenation or carbonylation catalyst.
    Type: Grant
    Filed: December 13, 1996
    Date of Patent: April 28, 1998
    Assignee: Eastman Chemical Company
    Inventors: Gerald Charles Tustin, Todd Jay Dickson
  • Patent number: 5731456
    Abstract: This invention pertains to the preparation of vinyl acetate by contacting a mixture of hydrogen and ketene with a heterogeneous catalyst containing a transition metal to produce acetaldehyde, which is then reacted with ketene in the presence of an acid catalyst to produce vinyl acetate.
    Type: Grant
    Filed: December 13, 1996
    Date of Patent: March 24, 1998
    Assignee: Eastman Chemical Company
    Inventors: Gerald Charles Tustin, Joseph Robert Zoeller, Leslie Sharon Depew
  • Patent number: 5726345
    Abstract: We describe a process for perfuming fabrics washed in the presence of a lipase-containing detergent and, optionally, subsequently treated with a fabric softener, said process being characterized in that said detergent and/or said fabric softener contains a compound of formula ##STR1## wherein a. R represents a radical derived from an fragrant alcohol of formula ROH and Y represents a C.sub.7 to C.sub.24 linear or branched, saturated or unsaturated alkyl radical, or a --(CH.sub.2).sub.n COOR group wherein R is defined as above and n is an integer from 0 to 6; or p1 b. Y represents a C.sub.7 to C.sub.24 linear or branched, saturated or unsaturated alkyl radical and R represents a group of formula ##STR2## wherein, either R.sup.1 represents hydrogen and R.sup.2 represents an alkylidene radical derived from a fragrant aldehyde of formula ##STR3## or R.sup.2 represents an alkylidene radical and R.sup.1 an alkyl radical, R.sup.1 and R.sup.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: March 10, 1998
    Assignee: Firmenich S.A.
    Inventors: Walter Paget, Daniel Reichlin, Roger Leslie Snowden, Eric C. Walborsky, Christian Vial
  • Patent number: 5719315
    Abstract: This invention pertains to the preparation of vinyl acetate by contacting within a contact zone a mixture of ketene and acetaldehyde with an acid catalyst at about one bar pressure and between about 85.degree. and 200.degree. C. and removing the reaction products from the contact zone.
    Type: Grant
    Filed: December 13, 1996
    Date of Patent: February 17, 1998
    Assignee: Eastman Chemical Company
    Inventors: Gerald Charles Tustin, Joseph Robert Zoeller, Leslie Sharon Depew
  • Patent number: 5414110
    Abstract: The present invention relates to(1) a Ru-Sn hetero-polynuclear complex as a novel catalyst which has a high catalytic activity and is useful for producing acetic acid and/or methyl acetate from methanol, and(2) a process for producing acetic acid and/or methyl acetate through a one-stage reaction starting with methanol wherein a catalyst can be used at a high concentration and the catalytic activity is maintained throughout the reaction.
    Type: Grant
    Filed: March 10, 1994
    Date of Patent: May 9, 1995
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Sumio Shinoda
  • Patent number: 5237092
    Abstract: A process for efficiently producing aryl formate and aromatic carboxylic acid from aldehyde, which comprises oxidizing an aromatic aldehyde with an oxygen-containing gas in the presence of a volatile solvent up to a reaction ratio of 40 to 70 mol % to convert the aromatic aldehyde to a peracid, adding a stabilizer, and allowing the remaining aromatic aldehyde and the aromatic peracid to react while the volatile solvent is distilled off.
    Type: Grant
    Filed: June 16, 1992
    Date of Patent: August 17, 1993
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toru Tanaka, Kazuo Tanaka, Teruo Aratake
  • Patent number: 5227517
    Abstract: The present invention relates to a process for producing ethylidene diacetate (EDDA) wherein at least one process step comprises condensing a feedstock of acetaldehyde and acetic anhydride in the presence of acetic acid and an iodide catalyst selected from the group consisting of potassium iodide, lithium iodide, methyl iodide and mixtures thereof. In a preferred embodiment, EDDA is prepared in an integrated process wherein the previously mentioned feedback is prepared by reacting dimethyl ether and acetic acid to form a first intermediate product mixture and hydrocarbonylating the first intermediate product mixture to form the condensation feedstock.
    Type: Grant
    Filed: April 15, 1992
    Date of Patent: July 13, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Francis J. Waller
  • Patent number: 5180847
    Abstract: A preferred process for producing 3-hydroxy-2,2,4-trimethylpentyl isobutyrate is described. The spent aqueous phase from an alkali metal hydroxide-catalyzed isobutyraldehyde condensation is concentrated in alkali metal isobutyrate salt, and the concentrated medium is introduced into a subsequent condensation to advantageously modify the isobutyraldehyde reaction. Increased conversions and productivities can thus be achieved. Preferred continuous processes, as well as preferred processes of controlled reaction duration and reactant/catalyst/salt ratios are also described. Further described is a preferred process for producing the diisobutyrate ester of 2,2,4-trimethyl-1,3-pentanediol, which in a preferred mode also achieves a desirable coproduction of the diol and its monoisobutyrate ester.
    Type: Grant
    Filed: February 15, 1991
    Date of Patent: January 19, 1993
    Assignee: BASF Corporation
    Inventors: Laurance R. Thurman, James B. Harris
  • Patent number: 5166413
    Abstract: The present invention relates to a process for the preparation of diols of the general formula (I) ##STR1## and monoesters thereof of the general formula (II) ##STR2## and the general formula (III) ##STR3## wherein R.sub.1 and R.sub.2 are the same of different groups and each denotes a lower alkyl group having 1 to 4 carbon atoms, preferably a methyl group. The process of this invention comprises condensing in a multi-phase reaction environment an aldehyde containing a hydrogen atom in the alpha position and having the general formula (IV) ##STR4## wherein R.sub.1 and R.sub.2 having the meaning given above, in the presence of a catalytic system consisting of a phase transferring catalyst and an alkaline substance.
    Type: Grant
    Filed: December 26, 1991
    Date of Patent: November 24, 1992
    Assignee: Neste Oxo Aktiebolag
    Inventors: Kjell Ankner, Pia Carlsson, Alfred Hopfinger, Hakan Rahkola, Kjell Sjoberg, Monica Soderlund
  • Patent number: 5089659
    Abstract: E7/Z9 -alkadien-1-ols which may be protected at the hydroxy group are prepared by subjecting a 7-hydroxyheptenal to a Wittig reaction with a phosphorylide to give an acetal compound which is converted by further Wittig reaction with a phosphorylide to an E7/Z9 -alkadienol.
    Type: Grant
    Filed: May 19, 1989
    Date of Patent: February 18, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Christiane Brueckner, Ernst Buschmann, Wolfgang Mackenroth, Walter Himmele, Heinz Eckhardt
  • Patent number: 4883906
    Abstract: A process for producing and refining trisubstituted glycol monoesters, e.g., 2,2,4-trimethyl-1,3-pentanediol monoester. The improvement resides in immediately distilling the crude condensation product mixture as it leaves the reactor before it has cooled or had any contact with added water.
    Type: Grant
    Filed: November 25, 1987
    Date of Patent: November 28, 1989
    Assignee: Union Carbide Corporation
    Inventors: John N. Argyropoulos, Edmond J. Derderian, Brian T. Keen, Timothy G. Bumgardner
  • Patent number: RE38283
    Abstract: Disclosed is a novel catalyst for use in producing a carboxylic ester from an aldehyde, an alcohol and molecular oxygen, which comprises a carrier having supported thereon Pd and Pb and a Pd/Pb atomic ratio (S) of 3/0.7≦S≦ from 3/0.7 to 3/1.3, and which exhibits a maximum intensity peak at a diffraction angle (2&thgr;) in the range of from 38.55° to 38.70° in a power X-ray diffraction pattern thereof, wherein the peak is ascribed to the (111) crystal face diffraction of a Pd—Pb intermetallic compound.
    Type: Grant
    Filed: March 20, 2002
    Date of Patent: October 21, 2003
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Setsuo Yamamatsu, Tatsuo Yamaguchi, Koshiro Yokota