Preparing Esters From Aldehydes Patents (Class 560/238)
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Patent number: 11279667Abstract: The present invention relates to a novel process for oxidative esterification, generally for reaction of aldehydes with alcohols in the presence of oxygenous gases directly to give the corresponding ester in the presence of a heterogeneous catalyst, by means of which, for example, (meth)acrolein can be converted to methyl (meth)acrylate. The new catalyst has titanium dioxide as the main component of the support material. The catalysts are especially notable for high mechanical and chemical stability and for good catalytic performance even over very long periods. The process is an improvement in the catalyst service life, activity and selectivity over prior art catalysts which lose activity and/or selectivity relatively quickly in continuous operation in media having even a small water content.Type: GrantFiled: September 18, 2018Date of Patent: March 22, 2022Assignee: Roehm GmbHInventors: Steffen Krill, Marcel Treskow
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Patent number: 11111204Abstract: A method for preparing methyl methacrylate from methacrolein and methanol; said method comprising contacting a mixture comprising methacrolein, methanol and oxygen with a heterogeneous catalyst comprising a support and a noble metal, wherein said support comprises silicon, and wherein said catalyst comprises from 0.1 to 40 mol % titanium and from 0.1 to 10 mol % of at least one noble metal.Type: GrantFiled: December 13, 2018Date of Patent: September 7, 2021Assignees: Dow Global Technologies LLC, Rohm and Haas CompanyInventors: Christopher D. Frick, Jeffrey A. Herron, Kirk W. Limbach, Wen Sheng Lee, Victor J. Sussman
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Patent number: 10934245Abstract: 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: GrantFiled: May 14, 2018Date of Patent: March 2, 2021Assignee: EVONIK OPERATIONS GMBHInventors: Alexander Lygin, Steffen Krill, Matthias Grömping, Andreas Tepperis
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Patent number: 10407626Abstract: 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: GrantFiled: August 12, 2016Date of Patent: September 10, 2019Assignee: ECOLAB USA INC.Inventors: Geeta Rana, Christopher Thomas Burrell
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Publication number: 20150148360Abstract: 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: ApplicationFiled: July 19, 2013Publication date: May 28, 2015Inventors: Jung-Hsin Lin, Jim-Min Fang, Ting-Rong Chen, Jhih-Bin Chen, Ching-Chow Chen, Tzu-Tang Wei
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Publication number: 20140378699Abstract: 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: ApplicationFiled: January 4, 2013Publication date: December 25, 2014Inventors: Venkat Raman Jayaraman, Samir Patel, Indrajit Thakor, Viral Maheshbhai Parekh, Mahesh Ladani, Chetan Patil, Ronak Patel, Prashant Raval
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Publication number: 20140213788Abstract: 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: ApplicationFiled: March 28, 2014Publication date: July 31, 2014Applicant: Vereniging voor Christelijk hoger onderwijs, wetenschappelijk onderzoek en patiëntenzorgInventors: Eelco RUIJTER, Romano ORRU, Anass ZNABET, Marloes POLAK, Nicholas TURNER
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Patent number: 8686145Abstract: 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: GrantFiled: September 16, 2010Date of Patent: April 1, 2014Assignee: Vereniging Voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek en Patientenzorg C/O Technology Transfer Officer VU & VumcInventors: Eelco Ruijter, Romano Orru, Anass Znabet, Marloes Polak, Nicholas Turner
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Publication number: 20130211033Abstract: 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: ApplicationFiled: October 27, 2011Publication date: August 15, 2013Applicants: MEURICE R&D ASBL, UNIVERSITE DE POITIERS, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUEInventors: Stefano Casciato, Yannick Pouilloux, Vincent Dubois
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Publication number: 20130150611Abstract: 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: ApplicationFiled: August 25, 2011Publication date: June 13, 2013Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Koji Hagiya
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Patent number: 8461373Abstract: 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: GrantFiled: July 31, 2008Date of Patent: June 11, 2013Assignee: Asahi Kasei Chemicals CorporationInventors: Ken Suzuki, Tatsuo Yamaguchi
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Patent number: 8450235Abstract: 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: GrantFiled: October 23, 2008Date of Patent: May 28, 2013Assignee: Asahi Kasei Chemicals CorporationInventors: Ken Suzuki, Tatsuo Yamaguchi
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Publication number: 20120330015Abstract: 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: ApplicationFiled: September 16, 2010Publication date: December 27, 2012Applicant: Vereniging voor Christelijk hoger onderwijs, wetenschappelijk onderzoek en patientenzorgInventors: Eelco Ruijter, Romano Orru, Anass Znabet, Marloes Polak, Nicholas Turner
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Publication number: 20120225020Abstract: 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: ApplicationFiled: February 24, 2012Publication date: September 6, 2012Inventors: Eduard Y. Chekmenev, Roman V. Shchepin
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Publication number: 20110251422Abstract: 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: ApplicationFiled: April 7, 2010Publication date: October 13, 2011Inventor: Brian A. Salisbury
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Publication number: 20110184206Abstract: 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: ApplicationFiled: July 31, 2008Publication date: July 28, 2011Inventors: Ken Suzuki, Tatsuo Yamaguchi
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Publication number: 20100256413Abstract: 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: ApplicationFiled: April 11, 2008Publication date: October 7, 2010Applicant: UNIVERSIDAD DE CÁDIZInventors: José María González Molinillo, Francisco Antonio Macías Dominguez, Rosa María Varela Montoya, Miguel Palma Lovillo, Carmelo García Barroso, Gerardo Fernández Barbero
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Publication number: 20100240616Abstract: 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: ApplicationFiled: November 1, 2007Publication date: September 23, 2010Inventors: Anne Kristin Holmeide, Jenny Rosman
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Patent number: 7696125Abstract: 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: GrantFiled: July 6, 2005Date of Patent: April 13, 2010Assignee: Lee Chang Yung Chemical Industry CorporationInventors: Kindtoken Hwaider Liu, Man-Yin Lo, Wen-Chyi Lin, Mei-Yuan Chang
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Patent number: 7091155Abstract: 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: GrantFiled: November 15, 2002Date of Patent: August 15, 2006Assignee: Chisso CorporationInventors: Kanichiro Inui, Takayoshi Takahashi, Toru Kurabayashi
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Patent number: 6809217Abstract: 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: GrantFiled: June 5, 2001Date of Patent: October 26, 2004Assignee: Davy Process Technology LimitedInventors: Stephen William Colley, Christopher Richard Fawcett, Colin Rathmell, Michael William Marshall Tuck
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Publication number: 20040192958Abstract: 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: ApplicationFiled: March 25, 2003Publication date: September 30, 2004Inventor: John Anthony Hyatt
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Patent number: 6767923Abstract: 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 conType: GrantFiled: October 29, 2002Date of Patent: July 27, 2004Assignee: BASF AktiengesellschaftInventors: 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
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Patent number: 6696594Abstract: 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: GrantFiled: May 13, 2002Date of Patent: February 24, 2004Assignee: Saudi Basic Industries CorporationInventors: Andrew T. Au, Jean-Pierre Lawanier, David Adam Flosser
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Publication number: 20030216587Abstract: 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: ApplicationFiled: May 13, 2002Publication date: November 20, 2003Applicant: Saudi Basic Industries Corporation (SABIC)Inventors: Andrew T. Au, Jean-Pierre Lawanier, David Adam Flosser
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Patent number: 6632959Abstract: 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: GrantFiled: February 7, 2000Date of Patent: October 14, 2003Assignee: Chisso CorporationInventors: Kan-ichiro Inui, Shunji Oshima, Toru Kurabayashi, Sakae Kawamura, Masahiro Yokota
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Publication number: 20030060655Abstract: 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: ApplicationFiled: June 3, 2002Publication date: March 27, 2003Inventors: Toshio Hayashi, Takahiro Inagaki
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Publication number: 20030060571Abstract: 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: ApplicationFiled: March 28, 2002Publication date: March 27, 2003Applicant: OMNOVA Solutions Inc.Inventors: Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson, Robert E. Medsker
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Patent number: 6362344Abstract: 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: GrantFiled: September 26, 2000Date of Patent: March 26, 2002Assignee: Bristol-Myers Squibb Pharma CompanyInventor: William A. Nugent
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Patent number: 6316663Abstract: 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: GrantFiled: March 21, 2001Date of Patent: November 13, 2001Assignee: Symyx Technologies, Inc.Inventors: Anil Guram, Cheryl Lund, Howard W. Turner, Tetsuo Uno
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Patent number: 6248920Abstract: 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: GrantFiled: December 22, 1997Date of Patent: June 19, 2001Assignee: Fujitsu LimitedInventors: Satoshi Takechi, Tadashi Kikukawa
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Patent number: 6215020Abstract: 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: GrantFiled: June 30, 1999Date of Patent: April 10, 2001Assignee: Eastman Chemical CompanyInventors: William A. Beavers, Robert D. Culp
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Manufacture of 1,3-propanediol esters from formaldehyde and ethylene using a modified prins reaction
Patent number: 6111135Abstract: 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: GrantFiled: December 2, 1998Date of Patent: August 29, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Douglas J. Adelman, Neville Everton Drysdale -
Patent number: 6072077Abstract: 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: GrantFiled: June 5, 1997Date of Patent: June 6, 2000Assignee: Haarmann & Reimer, GmbHInventors: Heinz-Jurgen Bertram, Matthias Guntert, Gunter Kindel
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Patent number: 6040472Abstract: 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: GrantFiled: October 23, 1997Date of Patent: March 21, 2000Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Setsuo Yamamatsu, Tatsuo Yamaguchi, Koshiro Yokota
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Patent number: 6018074Abstract: 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: GrantFiled: October 5, 1998Date of Patent: January 25, 2000Assignee: BASF AktiengesellshcaftInventors: Detlef Kratz, Achim Stammer, Tom Witzel, Martin Brudermuller
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Patent number: 6018075Abstract: 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: GrantFiled: May 12, 1999Date of Patent: January 25, 2000Assignee: Roche Vitamins Inc.Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
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Patent number: 5892102Abstract: 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: GrantFiled: July 30, 1997Date of Patent: April 6, 1999Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Yuji Mikami, Akio Takeda, Motomu Oh-Kita
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Patent number: 5821384Abstract: 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: GrantFiled: March 27, 1997Date of Patent: October 13, 1998Assignee: Eastman Chemical CompanyInventors: Joseph Robert Zoeller, Donald Wayne Lane, Eleanor Hawkins Cwirko, Dewey Wayne Fuller, Jr., Scott Donald Barnicki
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Patent number: 5770762Abstract: 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: GrantFiled: April 22, 1997Date of Patent: June 23, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Takashi Onishi
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Patent number: 5744637Abstract: 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: GrantFiled: December 13, 1996Date of Patent: April 28, 1998Assignee: Eastman Chemical CompanyInventors: Gerald Charles Tustin, Todd Jay Dickson
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Patent number: 5731456Abstract: 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: GrantFiled: December 13, 1996Date of Patent: March 24, 1998Assignee: Eastman Chemical CompanyInventors: Gerald Charles Tustin, Joseph Robert Zoeller, Leslie Sharon Depew
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Patent number: 5726345Abstract: 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: GrantFiled: August 22, 1996Date of Patent: March 10, 1998Assignee: Firmenich S.A.Inventors: Walter Paget, Daniel Reichlin, Roger Leslie Snowden, Eric C. Walborsky, Christian Vial
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Patent number: 5719315Abstract: 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: GrantFiled: December 13, 1996Date of Patent: February 17, 1998Assignee: Eastman Chemical CompanyInventors: Gerald Charles Tustin, Joseph Robert Zoeller, Leslie Sharon Depew
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Patent number: 5414110Abstract: 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: GrantFiled: March 10, 1994Date of Patent: May 9, 1995Assignee: Daicel Chemical Industries, Ltd.Inventor: Sumio Shinoda
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Patent number: 5237092Abstract: 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: GrantFiled: June 16, 1992Date of Patent: August 17, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toru Tanaka, Kazuo Tanaka, Teruo Aratake
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Patent number: 5227517Abstract: 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: GrantFiled: April 15, 1992Date of Patent: July 13, 1993Assignee: Air Products and Chemicals, Inc.Inventor: Francis J. Waller
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Patent number: 5180847Abstract: 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: GrantFiled: February 15, 1991Date of Patent: January 19, 1993Assignee: BASF CorporationInventors: Laurance R. Thurman, James B. Harris
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Patent number: 5166413Abstract: 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: GrantFiled: December 26, 1991Date of Patent: November 24, 1992Assignee: Neste Oxo AktiebolagInventors: Kjell Ankner, Pia Carlsson, Alfred Hopfinger, Hakan Rahkola, Kjell Sjoberg, Monica Soderlund
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Patent number: RE38283Abstract: 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: GrantFiled: March 20, 2002Date of Patent: October 21, 2003Assignee: Asahi Kasei Kabushiki KaishaInventors: Setsuo Yamamatsu, Tatsuo Yamaguchi, Koshiro Yokota