Preparing Esters By Alkylation Or Isomerization Patents (Class 560/203)
  • Patent number: 11021617
    Abstract: The disclosure relates to polymers including one or more 1,1-disubstitued alkene monomers. By employing a plurality of monomers and/or tailored chain structure, polymers having improved combinations of properties are achieved. The polymer may be a copolymer, preferably including two or more 1,1-disubstituted alkene monomers. The polymer may be a homopolymer having a tailored chain structure.
    Type: Grant
    Filed: April 11, 2019
    Date of Patent: June 1, 2021
    Assignee: Sirrus, Inc.
    Inventors: Jeffrey M. Sullivan, Aniruddha Palsule, Alexander R. Holzer, Peter Rulon Stevenson, Kshitij Kishen Parab
  • Patent number: 10934411
    Abstract: Curable compositions containing a compound comprising a conjugated diene group and a 1,1-di-activated vinyl compound are described. The curable compositions can cure by pericyclic reaction mechanisms.
    Type: Grant
    Filed: October 2, 2017
    Date of Patent: March 2, 2021
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Jonathan Thomas Martz, Michael Andrew Zalich, Aditya Lakshmi Narasimha Raju Gottumukkala, Stuart Damon Hellring, Ronnie Albertus Johannes Peskens
  • Patent number: 9540309
    Abstract: An improvement in the production of methylidene malonates is attained by use of specific reaction phase and/or separation phase polymerization inhibitors and combinations thereof.
    Type: Grant
    Filed: March 9, 2015
    Date of Patent: January 10, 2017
    Assignee: OptMed, Inc.
    Inventor: Bernard M Malofsky
  • Patent number: 8829225
    Abstract: An improvement in the production of 1,1-disubstituted ethylenes is attained by contacting a 1,1-disubstituted ethylene with alumina and separating the alumina to obtain a 1,1-disubstituted ethylene with a good combination of cost, purity, shelf life and cure rate.
    Type: Grant
    Filed: January 28, 2013
    Date of Patent: September 9, 2014
    Assignee: OptMed, Inc.
    Inventors: Francis McConville, John Gregory Reid, Murugappa Vedachalam
  • Publication number: 20130197264
    Abstract: An improved process for the production of methylidene malonates is attained by use of select iminium salt reactants.
    Type: Application
    Filed: January 28, 2013
    Publication date: August 1, 2013
    Applicant: OptMed, Inc.
    Inventor: OptMed, Inc.
  • Patent number: 7863478
    Abstract: The invention relates to compounds of the formula (I) or (II), to compositions which comprise such compounds, to corresponding processes for the preparation of the compounds or the compositions comprising same, and to the use thereof as light-protection filters.
    Type: Grant
    Filed: July 27, 2005
    Date of Patent: January 4, 2011
    Assignee: Merck Patent GmbH
    Inventors: Christophe Carola, Frank Pfluecker, Herwig Buchholz, Hansjürgen Driller, Hans Neunhoeffer, Evgeniy V. Blyumin
  • Publication number: 20100286433
    Abstract: Novel improved processes for the production and isolation of methylidene malonates via direct and indirect adduct processes.
    Type: Application
    Filed: May 6, 2010
    Publication date: November 11, 2010
    Inventors: Bernard M. Malofsky, Chris Mariotti
  • Publication number: 20080211333
    Abstract: An embodiment of the invention relates to a spindle motor of a magnetic recording storage device, the spindle motor comprising a fluid dynamic bearing comprising a lubricant comprising di-2-ethyl hexyl pimelate, di-2-ethyl hexyl suberate, or combinations thereof.
    Type: Application
    Filed: March 1, 2007
    Publication date: September 4, 2008
    Applicant: SEAGATE TECHNOLOGY LLC
    Inventors: Raquib Uddin Khan, James H. Smith
  • Patent number: 7335799
    Abstract: The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: February 26, 2008
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Patent number: 7173149
    Abstract: A process for preparing alkynecarboxylic acids includes the oxidation of an alkyne alcohol with a hypohalite in the presence of a nitroxyl compound at a pH of greater than 7 with continual addition of the alkyne alcohol and of the hypohalite to the reaction mixture.
    Type: Grant
    Filed: September 22, 2003
    Date of Patent: February 6, 2007
    Assignee: Consortium für elektrochemische Industrie GmbH
    Inventors: Jürgen Stohrer, Elke Fritz-Langhals, Christian Brüninghaus
  • Patent number: 7038072
    Abstract: The present invention is directed to a process for the synthesis of monoalkylated C—H acidic methylene group-containing compounds, such as malonic esters, and malonic ester nitriles.
    Type: Grant
    Filed: July 21, 2003
    Date of Patent: May 2, 2006
    Assignee: Degussa AG
    Inventors: Kerstin Bodmann, Oliver Meyer, Manfred Kaufhold, Jürgen Fieker, Renate Paulczynski
  • Patent number: 6740193
    Abstract: In accordance with the present invention, there are provided gem-diesters and epoxidized derivatives thereof. When cured, thermosets comprising invention gem-diesters and epoxidized derivatives thereof have thermally and/or chemically labile gem-diester groups interspersed throughout the crosslinked network. Thus, thermosets based on invention gem-diesters and epoxidized derivatives thereof can be easily reworked thermally or chemically by treatment with dilute acidic or basic solutions. Further provided by the present invention are adhesive compositions comprising invention gem-diesters and epoxidized derivatives thereof.
    Type: Grant
    Filed: December 21, 2001
    Date of Patent: May 25, 2004
    Assignee: Henkel Corporation
    Inventors: John G. Woods, Jianzhao Wang, Jean M. J. Fréchet
  • Patent number: 6646155
    Abstract: An ester of an &agr;,&bgr;-unsaturated carboxylic acid is prepared by reacting the carboxylic acid with a C6-C12-alkanol, cyclopentanol or cyclohexanol in the presence of an acidic esterification catalyst and of an entraining agent for removing the water of reaction formed in the esterification, by a process in which the entraining agent used is the olefin on which the alkanol is based.
    Type: Grant
    Filed: August 5, 2002
    Date of Patent: November 11, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Herzog, Gerhard Nestler, Jürgen Schröder
  • Publication number: 20030162994
    Abstract: A subject of the present invention is new 6,6′-bis-(1-phosphanorbornadiene) diphosphines, their preparation process and their use in asymmetrical catalysis.
    Type: Application
    Filed: January 15, 2003
    Publication date: August 28, 2003
    Inventors: Francois Mathey, Francois Mercier, Michel Spagnol, Frederic Robin, Virginie Mouries
  • Patent number: 6555703
    Abstract: The invention relates to a process for forming a carboxylic benzyl ester comprising reacting a dibenzyl ether with a carboxylic acid in the presence of a heteropolyacid and forming a carboxylic acid benzyl ester.
    Type: Grant
    Filed: August 31, 2001
    Date of Patent: April 29, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Bernd-Ulrich Schenke
  • Patent number: 6541655
    Abstract: Complexes of a selected class of chiral ligands with molybdenum, tungsten or chromium, preferably molybdenum, are effective as catalysts in highly enantioselective and regioselective alkylation of allylic substrates.
    Type: Grant
    Filed: September 7, 2001
    Date of Patent: April 1, 2003
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Barry M. Trost, Iwao Hachiya
  • Patent number: 6534657
    Abstract: Ferrocene anchored chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. The new ligands are effective for asymmetric Pd-catalyzed allylic alkylation reactions and Ag-catalyzed [3+2] cyclization of azomethine ylides.
    Type: Grant
    Filed: February 9, 2001
    Date of Patent: March 18, 2003
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 6462224
    Abstract: 1,1-cyclopropanedicarboxylic diesters are prepared from malonic diesters, 1,2-dihaloethane and alkali metal carbonate in the presence of a mixture of available or in situ-produced phase transfer catalyst and polyalkylene glycol or derivatives thereof which are capped at one or both ends, in particular those with ether end groups, where the molar ratio of malonic diester: 1,2-dihaloethane: alkali metal carbonate is 1:(1 to 7):(1 to 1.4).
    Type: Grant
    Filed: December 19, 2000
    Date of Patent: October 8, 2002
    Assignee: Degussa AG
    Inventors: Andreas Harthun, Manfred Neumann, Christoph Theis
  • Patent number: 6417391
    Abstract: A process for the preparation of a 2-methyl-1,3-dicarboxylate by reaction of a 1,3-dicarboxylate with formaldehyde and hydrogen, where, based on 1 mol of dicarboxylate, from 1.0 to 2.0 mol of formaldehyde are used, and either the reaction mixture or 2-hydroxymethyl-2-methyl-1,3-dicarboxylate isolated therefrom as by-product are subjected to thermolysis at temperatures of from 50° C. to 300° C.
    Type: Grant
    Filed: October 12, 1999
    Date of Patent: July 9, 2002
    Assignee: Degussa AG
    Inventor: Frank Bauer
  • Patent number: 6350898
    Abstract: Malonic esters of the general formula where R is C1-10-alkyl, C3-10-alkenyl or aryl-C1-4-alkyl, are prepared by reacting an alkali metal salt of malonic acid with a halide of the general formula R—X (II), where R is as defined above and X is chlorine, bromine or iodine, in the presence of water and a phase-transfer catalyst.
    Type: Grant
    Filed: January 10, 2000
    Date of Patent: February 26, 2002
    Assignee: Lonza AG
    Inventors: Stefan Hildbrand, Paul Hanselmann
  • Patent number: 6333430
    Abstract: A process for preparing a tert-alkyl carboxylic acid ester represented by the formula (III): wherein R1 is an organic group; and each of R2 and R3 is independently an alkyl group having 1 to 4 carbon atoms, comprising reacting a carboxylic acid represented by the formula (I): R1—COOH  (I) wherein R1 is as defined above, with a vinylidene compound represented by the formula (II): wherein R2 and R3 are as defined above, in the presence of a phosphorus halide. The tert-alkyl carboxylic acid ester can be used as intermediates for pharmaceuticals such as antibiotics.
    Type: Grant
    Filed: May 2, 2000
    Date of Patent: December 25, 2001
    Assignee: Sumika Fine Chemicals Co., Ltd.
    Inventors: Tetsuya Shintaku, Kiyoshi Sugi, Tadashi Katsura, Nobushige Itaya
  • Publication number: 20010044554
    Abstract: A process for the preparation of a 2-methyl-1,3-dicarboxylate by reaction of a 1,3-dicarboxylate with formaldehyde and hydrogen, where, based on 1 mol of dicarboxylate, from 1.0 to 2.0 mol of formaldehyde are used, and either the reaction mixture or 2-hydroxymethyl-2-methyl-1,3-dicarboxylate isolated therefrom as by-product are subjected to thermolysis at temperatures of from 50° C. to 300° C.
    Type: Application
    Filed: October 12, 1999
    Publication date: November 22, 2001
    Inventor: FRANK BAUER
  • Patent number: 6310003
    Abstract: The invention relates to a composition and procedure for manipulating the behavior of the orange wheat blossom midge, Sitodiplosis mosellana. More importantly, this invention relates to the preparation and use of 2,7-nonanediyl dibutyrate or stereoisomers thereof for manipulating the behavior of S. mosellana.
    Type: Grant
    Filed: November 29, 2000
    Date of Patent: October 30, 2001
    Assignees: Simon Fraser University, Agriculture and Agri-Food Canada
    Inventors: Regine Gries, Gerhard Gries, Khaskin Grigori, Olfert Owen, Lori-Ann Kaminski
  • Patent number: 6278015
    Abstract: The present invention provides a process for preparing esters or thioesters of trifluoroacetic acid from trifluoroacetyl chloride and an alcohol or a thiol with the ester or thioester being present as the solvent. Esters and thioesters of trifluoroacetic acid are fine chemical intermediates which can be used in the manufacture of pharmaceuticals, agricultural chemicals, liquid crystals, dyes and industrial chemicals. Trifluoroacetate esters and thioesters can also be used as solvents in the manufacture of other fine chemicals, pharmaceuticals, agricultural chemicals, liquid crystals, industrial chemicals and dyes.
    Type: Grant
    Filed: July 17, 2000
    Date of Patent: August 21, 2001
    Assignee: Rohm and Haas Company
    Inventors: Lori Ann Spangler, Fereydon Abdesaken, Joshua Anthony Chong
  • Patent number: 6262298
    Abstract: The invention relates to a process for the C-alkylation of dialkyl malonates, in which a dialkyl malonate is reacted with an alkyl halide in the presence of potassium carbonate as a hydrogen halide acceptor in an inert solvent, and a phase-transfer catalyst is not added until from 50 to 80% of the dialkyl malonate has reacted. The phase-transfer catalyst may be, for example, a tetraalkylammonium salt or a tetraalkylammonium hydroxide, a tetraalkylphosphonium salt or a tetraalkylphosphonium hydroxide or a crown ether.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: July 17, 2001
    Assignee: Huels Aktiengesellschaft
    Inventors: Josef Metz, Clemens Osterholt
  • Patent number: 6215035
    Abstract: The invention relates to a process for the preparation of aralkylated aromatic compound with both small and large size aralkylating agents; wherein the catalyst used is heterogeneous solid catalyst removable from the reaction products by simple filtration, thus allowing the separated catalyst to be reused in the process. The catalyst is selected from micro or mesoporous gallosilicates and galloaluminosilicates, having structure similar to that of zeolites known in the prior art.
    Type: Grant
    Filed: January 11, 1999
    Date of Patent: April 10, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Vasant Ramchandra Choudhary, Suman Kumar Jana, B-Phani Kiran
  • Patent number: 6049010
    Abstract: A method for preparation of a dicarbonyl compound of the following formula ##STR1## by reacting a conjugated alkadiene compound of the formula ##STR2## with a 1,3-dicarbonyl compound of the formula ##STR3## in the presence of an acid catalyst. The products of the method are useful in the preparation of compounds such as vitamins A and E, various carotenoids, Retin A, dehydrolinalool, pseudoionone, citral, and linalool.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: April 11, 2000
    Assignee: Loyola University of Chicago
    Inventors: James H. Babler, Harvey W. Posvic
  • Patent number: 5739375
    Abstract: Methyl compounds are prepared from carbon acids by reaction with dimethyl carbonate in the presence of a nitrogen-containing base.
    Type: Grant
    Filed: April 4, 1997
    Date of Patent: April 14, 1998
    Assignee: BASF Aktiengellschaft
    Inventor: Rolf Fischer
  • Patent number: 4943397
    Abstract: The present invention relates to a process for metathesizing an olefin having at least one terminal functional group which comprises contacting said olefin at metathesis conditions with a catalyst comprising: (a) a transition metal selected from tungsten, molybdenum and rhenium, (b) an organometallic compound based on an element selected from aluminum, tin, lead, magnesium and titanium, and (c) an oxophilic agent having a metal-oxygen bond strength greater than the metal-oxygen bond strength of said transition metal.
    Type: Grant
    Filed: September 22, 1988
    Date of Patent: July 24, 1990
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4943396
    Abstract: The present invention relates to a process for preparing linear alpha, omega difunctional molecules by a process which comprises isomerizing olefins having at least one terminal functional group to form a mixture of functionalized olefinic isomers and metathesizing said functionalized olefinic isomers to produce a mixture of difunctional molecules and internal olefins.
    Type: Grant
    Filed: September 22, 1988
    Date of Patent: July 24, 1990
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4894471
    Abstract: A continuous process for the alkylation of CH-acid compounds with dialkyl carbonates in gas-liquid phase transfer catalysis conditions is described, consisting of contacting a mixture of a CH-acid compound (arylacetonitrile or malonic diester) and of a dialkylcarbonate, optionally added with an inert carrier (constituted by a polar or aprotic polar liquid or by a gas), with a catalytic bed comprising alumina spheres carrying a base and a phase transfer catalyst.
    Type: Grant
    Filed: March 30, 1987
    Date of Patent: January 16, 1990
    Assignee: Consiglio Nazionale Delle Richerche
    Inventors: Enrico Angeletti, Franco Trotta, Pietro Tundo, Paolo Venturello
  • Patent number: 4808747
    Abstract: Alkylidene compounds and arylidene compounds are prepared by reacting the corresponding CH-acidic compounds with carbonyl compounds in the presence of a catalyst comprising a metal compound of a metal of Groups IIA, IIIA, IVA, IB, IIB, VIB, VIIB, or VIIIB of the periodic table of elements. The rate of reaction is increased by adding 1 to 40% water referred to the weight of catalyst used.
    Type: Grant
    Filed: March 14, 1985
    Date of Patent: February 28, 1989
    Assignee: Huls AG
    Inventor: Walter K. Homann
  • Patent number: 4667050
    Abstract: Substituted vinylcyclopropane carboxylates, useful precursors to pyrethroid insecticides, are prepared by noble metal catalyzed addition of 1-methyl-3-buten-2-yl or 4-methyl-3-penten-1-yl carbonates or carboxylic acid esters to malonic acid diesters, alkyl acetates or alkyl cyanoacetates.
    Type: Grant
    Filed: March 15, 1984
    Date of Patent: May 19, 1987
    Assignee: The Dow Chemical Company
    Inventors: Edmund P. Woo, Joseph J. Laux
  • Patent number: 4428887
    Abstract: Mono-substituted terminal diesters of malonic acid are prepared by reaction of the corresponding substituted 1,2-diesters with alkali metal hydride in the presence of organic solvent medium.
    Type: Grant
    Filed: July 14, 1982
    Date of Patent: January 31, 1984
    Assignee: Monsanto Company
    Inventors: Jacob S. Tou, Alfred A. Schleppnik
  • Patent number: 4241216
    Abstract: A continuous process for the preparation in at least one esterification reactor of phthalate diesters utilizing phthalic acid or anhydride and a stoichiometric excess of at least one saturated aliphatic alcohol containing about 4 to about 10 carbon atoms comprises (a) reaction of phthalic acid or anhydride with said alcohol in a reactor zone, (b) purification of the diester in a purification zone in which the reaction product is neutralized with an alkali metal hydroxide, i.e., sodium hydroxide, to separate the diester and the unreacted phthalic acid or anhydride together with said saturated alcohol utilized in the reaction, said reaction product is separated into an organic phase and an aqueous waste phase.
    Type: Grant
    Filed: January 2, 1979
    Date of Patent: December 23, 1980
    Assignee: BASF Wyandotte Corporation
    Inventors: Lee H. Bergman, John J. Evangelista, William M. Herring
  • Patent number: 4235786
    Abstract: An improved process for preparing oil-soluble derivatives of unsaturated C.sub.4 -C.sub.10 dicarboxylic acid materials, e.g. the product of the reaction of polyisobutylene and maleic anhydride, under Ene reaction conditions characterized in that said Ene reaction is conducted under acidic conditions as by conducting said reaction in the presence of from 0.01 to 5 wt. %, based on total weight of the reactants, of an oil-soluble strong organic acid containing a hydrogen dissociating moiety which has a pK of less than about 4.0, as exemplified by a C.sub.15 to C.sub.76 hydrocarbyl-substituted sulfonic acid, whereby sediment resulting from said Ene reaction is markedly reduced to less than 1 wt. %.
    Type: Grant
    Filed: October 1, 1979
    Date of Patent: November 25, 1980
    Assignee: Exxon Research & Engineering Co.
    Inventor: Max J. Wisotsky
  • Patent number: 4100200
    Abstract: A compound having the formulaR -- SO.sub.2 O -- CH.sub.2 -- O -- CH.sub.2 -- OSO.sub.2 -- Rwherein R is alkyl, is prepared by reacting a compound having the formula ##STR1## wherein R and R' are alkyl with a cyclic polyoxymethylene or a linear polyoxymethylene in a substantially humidity-free environment. The compound is useful as an oxydimethylating agent for organic compounds.
    Type: Grant
    Filed: February 11, 1977
    Date of Patent: July 11, 1978
    Assignee: Eastman Kodak Company
    Inventors: Cataldo Aldino Maggiulli, Donald MacArthur Burness, William Clarence Perkins
  • Patent number: 4064185
    Abstract: Compositions are provided as well as methods for preparing the compositions which serve as cyclization precursors for the preparation of C-11 alkenyl substituted steroids and nor-steroids. The alkenyl group may be converted after cyclization to a variety of heterosubstituents to provide heterofunctionalized C-11 steroids and nor-steroids. The compounds are provided having an initiator group, which has a chalcoxy atom in juxtaposition to a double bond, an olefinically unsaturated linking group and a terminating group which acts to from a carbocation which reacts with a nucleophile to provide a stable product. The C-11 substituent is found to provide upon cyclization the alpha-configuration, so that the subject compounds provide a direct route to the difficultly accessible alpha-C-11 substituted steroids, or, if desired, the alpha-configuration can be inverted to the beta-configuration.
    Type: Grant
    Filed: April 28, 1975
    Date of Patent: December 20, 1977
    Assignee: The Board of Trustees of Leland Stanford Junior University
    Inventors: William S. Johnson, Grant E. Dubois