Preparing Esters From Aldehydes Patents (Class 560/210)
  • Patent number: 10683255
    Abstract: A process for the production of an ethylenically unsaturated carboxylic acid ester, preferably an ?,ß ethylenically unsaturated carboxylic acid ester is described. The process takes place by the reaction of formaldehyde or a suitable source thereof with a carboxylic acid ester in the presence of a basic metal methyl carbonate co-reactant, wherein the process produces a second basic metal salt and wherein the process includes the step of contacting the second basic metal salt with: a) carbon dioxide (CO2) and optionally, methanol, and/or b) dimethyl carbonate, to regenerate the basic metal methyl carbonate co-reactant. The invention includes use of carbon dioxide and/or dimethyl carbonate to regenerate a basic metal methyl carbonate.
    Type: Grant
    Filed: October 11, 2017
    Date of Patent: June 16, 2020
    Assignee: Lucite International UK Limited
    Inventors: Graham Ronald Eastham, Jonathan Ainsley Iggo, Michael Beaumont
  • Patent number: 10640448
    Abstract: A method can prepare a carboxylic ester. The method includes reacting an aldehyde in the presence of an aluminium alkoxide applied to a support material.
    Type: Grant
    Filed: April 30, 2018
    Date of Patent: May 5, 2020
    Assignee: Evonik Operations GmbH
    Inventors: Alexander Lygin, Steffen Krill, Matthias Grömping, Andreas Tepperis
  • Patent number: 8889586
    Abstract: In one embodiment, the invention is to a catalyst composition, comprising vanadium and titanium. Preferably, the molar ratio of vanadium to titanium in an active phase of the catalyst composition is greater than 0.5:1.
    Type: Grant
    Filed: January 8, 2014
    Date of Patent: November 18, 2014
    Assignee: Celanese International Corporation
    Inventors: Dick Nagaki, Heiko Weiner, Josefina T. Chapman, Mark O. Scates, Alexandra S. Locke, Craig J. Peterson
  • Publication number: 20140206897
    Abstract: A process for forming methyl methacrylate can comprise: reacting ethylene, carbon monoxide, and hydrogen, in the presence of a first catalyst comprising a metal carbonyl; removing a first reaction product comprising propionaldehyde; reacting the first reaction product with formaldehyde; removing a second reaction product comprising methacrolein; reacting the second reaction product with oxygen and methanol in the presence of a second catalyst to form a third reaction product comprising methyl methacrylate. Another process for forming methyl methacrylate can comprising: reacting ethylene with carbon monoxide to form propionaldehyde; reacting the propionaldehyde with formaldehyde to form methacrolein; and reacting the methacrolein with methanol and oxygen to form the methyl methacrylate.
    Type: Application
    Filed: January 20, 2014
    Publication date: July 24, 2014
    Applicant: Saudi Basic industries Corporation
    Inventors: James Malcolm Allman, James Kauffman
  • Publication number: 20140121403
    Abstract: A process for producing an acrylate product from methanol and acetic acid, in which, in a reaction zone A, the methanol is partially oxidized to formaldehyde in a catalyzed gas phase reaction, the product gas mixture A obtained and an acetic acid source are combined to form a reaction gas input mixture B which comprises acetic acid in excess over formaldehyde, and the formaldehyde in reaction gas input mixture B is aldol-condensed to acrylic acid in the presence of a catalyst in a reaction zone B to form an acrylic acid-containing product gas mixture B from which an acrylate product stream may be separated. Suitable aldol condensation catalysts include vanadium-bismuth, vanadium-titanium-bismuth, vanadium-bismuth-tungsten, vanadium-titanium-tungsten, vanadium-titanium and vanadium-tungsten.
    Type: Application
    Filed: June 27, 2013
    Publication date: May 1, 2014
    Inventors: Dick Nagaki, Craig J. Peterson, Elizabeth Bowden, Josefina T. Chapman, Sean Mueller
  • Patent number: 8658822
    Abstract: In one embodiment, the invention is to a process for producing an acrylate product. The process comprises the step of reacting an alkanoic acid and an alkylenating agent under conditions effective to produce a crude acrylate product. A molar ratio of alkylenating agent to alkanoic acid is maintained at a level of at least 1.
    Type: Grant
    Filed: October 1, 2012
    Date of Patent: February 25, 2014
    Assignee: Celanese International Corporation
    Inventors: Sean Mueller, Dick Nagaki, Craig J. Peterson, Mark O. Scates, Heiko Weiner, Josefina T. Chapman, Alexandra S. Locke
  • Publication number: 20130261323
    Abstract: Isobutene, isoprene, and butadiene are obtained from mixtures of C4 and/or C5 olefins by dehydrogenation. The C4 and/or C5 olefins can be obtained by dehydration of C4 and C5 alcohols, for example, renewable C4 and C5 alcohols prepared from biomass by thermochemical or fermentation processes. Isoprene or butadiene can be polymerized to form polymers such as polyisoprene, polybutadiene, synthetic rubbers such as butyl rubber, etc. in addition, butadiene can be converted to monomers such as methyl methacrylate, adipic acid, adiponitrile, 1,4-butadiene, etc. which can then be polymerized to form nylons, polyesters, polymethylmethacrylate etc.
    Type: Application
    Filed: May 24, 2013
    Publication date: October 3, 2013
    Applicant: GEVO, INC.
    Inventors: Matthew W. Peters, Joshua D. Taylor, David E. Henton, Leo E. Manzer, Patrick R. Gruber, Josefa M. Griffith, Yassin Al Obaidi
  • Publication number: 20130245310
    Abstract: A process for producing an acrylate product comprises the step of contacting an alkanoic acid and an alkylenating agent over a catalyst over conditions effective to produce the acrylate product. The catalyst composition comprises vanadium, titanium and bismuth. Preferably, the catalyst comprises vanadium to bismuth at a molar ratio of greater than 0.2:1, in an active phase.
    Type: Application
    Filed: March 11, 2013
    Publication date: September 19, 2013
    Applicant: Celanese International Corporation
    Inventors: Dick Nagaki, Craig Peterson, Heiko Weiner, Elizabeth Bowden, Josefina T. Chapman
  • Patent number: 8536368
    Abstract: In one embodiment, the invention relates to a process for producing an acrylate product. The process comprises the step of reacting a reaction mixture comprising an alkanoic acid and an alkylenating agent composition under conditions effective to form a crude acrylate product. The alkylenating agent composition comprises at least 1 wt % of a ring-structured compound comprising at least two oxygen atoms and at least one carbon atom, e.g., trioxane and/or tetraoxane. The process further comprises the step of separating at least a portion of the crude acrylate product to form at least one alkylenating agent stream and at least one purified acrylate product stream comprising acrylate product.
    Type: Grant
    Filed: October 1, 2012
    Date of Patent: September 17, 2013
    Assignee: Celanese International Corporation
    Inventors: Sean Mueller, Dick Nagaki, Craig J. Peterson, Josefina T. Chapman
  • Publication number: 20130085292
    Abstract: In one embodiment, the invention is to a process for producing an acrylate product. The process comprises the step of reacting an alkanoic acid and an alkylenating agent under conditions effective to produce a crude acrylate product. A molar ratio of alkylenating agent to alkanoic acid is maintained at a level of at least 1.
    Type: Application
    Filed: October 1, 2012
    Publication date: April 4, 2013
    Applicant: Celanese International Corporation
    Inventor: Celanese International Corporation
  • Publication number: 20100137630
    Abstract: Acetals are formed from an aldehyde hydrogenation product mixture comprising alcohols and at most 2% of alde-hydes and the product is distilled to yield purified alcohols and a second stream containing acetals and/or unsaturated ethers.
    Type: Application
    Filed: February 27, 2008
    Publication date: June 3, 2010
    Inventors: Ronald Dean Garton, Corey W. Reed, Rao Krishna Kulai, Bruce D. Lilly, Ramzi Yanni Saleh, Raphael Frans Caers
  • Patent number: 7205443
    Abstract: A process for producing a fluorine-containing 2,4-diol represented by the formula [4], wherein R1 represents a hydrogen atom or an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7; R2 represents an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7; and R1 and R2 are optionally bonded to each other to form a ring, includes reducing a hydroxy ketone represented by the formula [3], wherein R1 and R2 are defined as above, by hydrogen in the presence of a ruthenium catalyst.
    Type: Grant
    Filed: January 26, 2005
    Date of Patent: April 17, 2007
    Assignee: Central Glass Company, Limited
    Inventors: Takeo Komata, Kei Matsunaga, Yoshiki Hirotsu, Shinya Akiba
  • Patent number: 7176335
    Abstract: A process prepares methacrolein from isobutane by subjecting isobutane to a partial catalytic dehydrogenation in the gas phase and using the isobutenic product gas mixture to charge an oxidation zone in which the isobutene is oxidized to methacrolein in the gas phase with heterogeneous catalysis using molecular oxygen accompanied by molecular nitrogen as the oxygen source.
    Type: Grant
    Filed: June 28, 2002
    Date of Patent: February 13, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Silke Berndt, Klaus Joachim Mueller-Engel, Goetz-Peter Schindler, Frank Rosowski, Jochen Petzoldt
  • Patent number: 7012039
    Abstract: An oxide catalyst composition for use in producing methacrolein or a mixture of methacrolein and methacrylic acid, wherein the oxide catalyst composition is represented by the formula (Mo+W)l2BiaAbBcFedXeSbfOg, wherein: A is at least one member selected from the group consisting of Y and the elements of the lanthanoid series exclusive of Pm; B is at least one member selected from the group consisting of K, Rb and Cs; X is Co solely, or a mixture of Co and at least one member selected from the group consisting of Mg and Ni; and a, b, c, d, e, f and g are, respectively, the atomic ratios of Bi, A, B, Fe, X, Sb and O, relative to twelve atoms of the total of Mo and W, wherein the atomic ratios (a to f) of the elements and the relationship between the amounts of the elements are chosen so as to satisfy specific requirements.
    Type: Grant
    Filed: December 20, 2002
    Date of Patent: March 14, 2006
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Toru Watanabe, Osamu Nagano
  • Patent number: 6914155
    Abstract: Active hydrogen in an active-hydrogen-containing compound is activated by using a polymer gel having a three-dimensional network structure holding a solvent inside thereof and active sites inside the three-dimensional network structure and surfaces thereof. The ratio of swell of the polymer gel is preferably set to not less than 2, and it is preferable for the polymer gel to have a basic functional group derived from at least one compound selected from the group consisting of tertiary amine compounds, quaternary ammonium salts, cyclic amine compounds and sulfides. The activation of active hydrogen in the active-hydrogen-containing compound is preferably carried out under the condition that the amount of basic active sites of the polymer gel per unit volume in the active system accompanying the activation of active hydrogen is set to not less than 0.43 mmol/cc.
    Type: Grant
    Filed: July 27, 2001
    Date of Patent: July 5, 2005
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hiroshi Yamamoto, Yoshiaki Hirano
  • Patent number: 6838576
    Abstract: A process for preparing functional group-containing olefinic compounds comprises the steps of (a) reacting at least one alkylidene phosphorane with at least one carbonyl-containing compound that comprises at least one group that is a leaving group, or that is capable of subsequent conversion to a leaving group, to form an olefinic compound that comprises at least one leaving group, the carbonyl-containing compound being selected from the group consisting of ketones and aldehydes; and (b) reacting the olefinic compound with at least one functional group-containing nucleophile to form a functional group-containing olefinic compound.
    Type: Grant
    Filed: October 23, 2003
    Date of Patent: January 4, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: Markus A. Wicki, Kent E. Nielsen
  • Patent number: 6787671
    Abstract: An osmium-assisted process for the oxidative cleavage of oxidizable organic compounds such as unsaturated organic compounds, including alkenes and olefins into aldehydes, carboxylic acids, esters, or ketones. The process uses a metal catalyst comprising osmium and a peroxy compound selected from the group consisting of peroxymonosulfuric acid and salts thereof to oxidatively cleave the oxidizable organic compound. In particular, the process enables aldehydes, carboxylic acids, esters, or ketones to be selectively produced from the corresponding mono-, 1,1-di-, 1,2-di-, tri-, or tetra-substituted olefins in a reaction that produces the result of ozonolysis but with fewer problems. The present invention further provides a process for oxidizing an aldehyde alone or with the osmium in an interactive solvent to produce an ester or carboxylic acid.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: September 7, 2004
    Assignee: Board of Trustees of Michigan State University
    Inventors: Babak Borhan, Benjamin R. Travis, Jennifer M. Schomaker
  • 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
  • Publication number: 20030162992
    Abstract: The present invention is an efficient process for the manufacture of &agr;-acyloxyacetaldehyde, a key intermediate in the synthesis of 1,3-oxathiolane and 1,3-dioxolane nucleosides.
    Type: Application
    Filed: December 12, 2002
    Publication date: August 28, 2003
    Inventors: Kyoichi A. Watanabe, Jinfa Du
  • Patent number: 6603034
    Abstract: A process for preparing organozinc halides in solvents, includes reacting a reactive halogen compound with zinc in one or more carboxylic esters. It is also possible to prepare keto, hydroxyl and amino compounds of organozinc halides obtained in a first step from a reactive halogen compound and zinc in one or more carboxylic esters, wherein the organozinc halide obtained is reacted in a second step with an electrophilic reaction partner and the reaction product of the second step is hydrolyzed in a third step.
    Type: Grant
    Filed: December 3, 2002
    Date of Patent: August 5, 2003
    Assignee: Consortium für Elektrochemische Industrie GmbH
    Inventors: Klas Sorger, Hermann Petersen, Jürgen Stohrer
  • Patent number: 6590122
    Abstract: The invented process for producing a polyester supplies a crotonaldehyde with a purity of 95% by weight or more to a reaction system in the reaction of ketene with crotonaldehyde. In this process, unreacted crotonaldehyde may be recovered from a reaction mixture obtained by the reaction of ketene with crotonaldehyde and may be recycled to the reaction system. The &agr;vinylcrotonaldehyde content of the crotonaldehyde to be supplied to the reaction system is, for example, less than 0.5% by weight, and the paraldehyde content of the crotonaldehyde to be supplied to the reaction system is, for example, less than 5% by weight. By decomposing the above-prepared polyester with, for example, hydrochloric acid, a sorbic acid having a satisfactory hue can be efficiently obtained.
    Type: Grant
    Filed: May 26, 2000
    Date of Patent: July 8, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Noboru Kamei, Akira Yamashita, Mitsuhiro Kouno
  • Patent number: 6452042
    Abstract: Substituted propenoates are prepared by eliminating an alcohol from a substituted malondialdehyde acetal, optionally in the presence of a homogeneous or heterogeneous catalyst.
    Type: Grant
    Filed: January 28, 2000
    Date of Patent: September 17, 2002
    Assignee: Creanova, Inc.
    Inventors: Frank Bauer, Chitoor Subramaniam
  • Patent number: 6414183
    Abstract: The present invention provides a method for stabilizing waste oil which is taken of each chemical apparatus of the manufacturing line of (meth)acryl acid and/or ester thereof, and treating the waste oil such as draining it out of the production apparatus, for example, a distillation tower from its bottom, sending and transporting it by a pump through a pipeline, and storing it in a storage tank in a simple manner while keeping the waste oil in a stable state. The waste oil can be stabilized by coexisting with solvent. The solvent used in the present invention is typically at least one selected from the group consisting of water, alcohol, ether, carboxylic acid, ketone, aromatic hydrocarbons, and aliphatic hydrocarbons.
    Type: Grant
    Filed: April 5, 2000
    Date of Patent: July 2, 2002
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kazuhiko Sakamoto, Sei Nakahara, Masatoshi Ueoka
  • Patent number: 6348619
    Abstract: A carboxylic acid ester is prepared by a process comprising: reacting an aldehyde and an alcohol in a liquid phase in the presence of molecular oxygen as indicated by the following reaction: RCHO+R′OH+O2→RCOOR′+H2O in the presence of a catalyst comprising at least palladium and an element X, wherein X is bismuth, lead or a combination thereof, supported on a carrier, wherein the catalyst has an acid strength, pKa, of more than 4.8 and shows an ammonia chemical adsorption amount at 0° C. of 0-150 &mgr;mol/g-catalyst.
    Type: Grant
    Filed: January 25, 1999
    Date of Patent: February 19, 2002
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Yasukazu Yoshida, Yuji Mikami, Motomu Oh-Kita
  • 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
  • Publication number: 20010014755
    Abstract: An ester compound, which is a production intermediate of a pyrethroid compound, given by formula 1
    Type: Application
    Filed: December 22, 2000
    Publication date: August 16, 2001
    Inventor: Tomonori Yoshiyama
  • 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: 6107513
    Abstract: A process for the production of a catalyst for preparing vinyl acetate in the gas phase from ethylene, acetic acid and oxygen or oxygen-containing gases which catalyst comprises palladium and/or its compounds, gold and/or its compounds and also alkali metal compounds on a particulate, porous support obtained bya) impregnating the support with soluble palladium and gold compounds,b) converting the soluble palladium and gold compounds into insoluble palladium and gold compounds by addition of an alkaline solution to the support.c) reducing the insoluble palladium and gold compounds on the support with a reducing agent in the liquid or gaseous phase,d) impregnating the support with at least one soluble alkali metal compound ande) finally drying the support at a maximum of 150.degree. C.,wherein the catalyst is brought into contact with at least one peroxidic compound in step b).
    Type: Grant
    Filed: June 24, 1999
    Date of Patent: August 22, 2000
    Assignee: Celanese GmbH
    Inventors: Bernhard Herzog, Roswitha Stein, Karl-Heinz Renkel
  • Patent number: 6054607
    Abstract: A process for the preparation of a cinnamic acid ester comprises condensing a benzaldehyde with an acetic acid ester in the presence of a base. The reaction mixture is then treated, without adding an additional solvent or after adding an additional solvent, with an acid to convert a 3-alkoxy-3-phenylpropionic acid ester in the reaction mixture into a corresponding cinnamic acid ester. This procedure allows cinnamic acid ester derivatives of high-purity to be obtained in good yield.
    Type: Grant
    Filed: October 14, 1998
    Date of Patent: April 25, 2000
    Assignee: Sankyo Company, Limited
    Inventors: Hideshi Okui, Yoshihisa Tsukamoto, Shigeru Mio
  • 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: 6005148
    Abstract: A supported catalyst comprising a support, an anchoring agent such as a heteropoly acid or anion, and a metal complex which is useful in a wide variety on organic reactions, especially the hydrogenation of substituted .alpha.,.beta. unsaturated acids and esters, is provided. Various methods of preparing the supported catalyst of the present invention is also disclosed.
    Type: Grant
    Filed: November 17, 1998
    Date of Patent: December 21, 1999
    Assignee: Seton Hall University
    Inventors: Setrak K. Tanielyan, Robert L. Augustine
  • Patent number: 5981818
    Abstract: A novel process is provided which integrates the cracking of hydrocarbon containing feedstocks with the olefins purification and olefins derivative process utilizing dilute olefin feedstocks.
    Type: Grant
    Filed: October 18, 1996
    Date of Patent: November 9, 1999
    Assignee: Stone & Webster Engineering Corp.
    Inventors: David Purvis, Richard H. Mc Cue
  • Patent number: 5969178
    Abstract: Disclosed is a method for producing methyl methacrylate, which comprises: subjecting isobutylene and/or tert-butanol to a gas phase catalytic oxidation reaction with molecular oxygen to thereby obtain gas (a) containing methacrolein gas and steam; introducing gas (a) and a methacrolein/methanol liquid mixture (I) into a dehydration tower at a lower portion thereof and at an upper portion thereof, respectively, thereby allowing the liquid mixture (I) to flow downwardly in the dehydration tower and contact countercurrently with the gas (a) in the dehydration tower, to thereby obtain a dehydrated gas mixture (b) containing methacrolein gas and methanol gas; introducing the dehydrated gas mixture (b) and a methacrolein/methanol liquid mixture (II) into an absorption tower at a lower portion thereof and at an upper portion thereof, respectively, thereby allowing the liquid mixture (II) to flow downwardly and contact countercurrently with the dehydrated gas mixture (b) in the absorption tower, thereby obtaining a m
    Type: Grant
    Filed: July 7, 1998
    Date of Patent: October 19, 1999
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hiroshige Okamoto, Hideaki Goto
  • Patent number: 5916987
    Abstract: A sulfur-containing O-(meth)acrylate compound of the following formula (1) is useful as a starting material for a resin composition used in optical applications such as a lens; ##STR1## wherein R represents hydrogen atom or methyl group; 1 represents an integer from 1 to 3; B is ##STR2## n is 1 or 2, m is 1, 2 or 3 and A is selected from certain arylene, aralkylene, thioether, dithioether or thiopheneylene radicals.
    Type: Grant
    Filed: May 21, 1997
    Date of Patent: June 29, 1999
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Seiichi Kobayashi, Nobuya Kawauchi, Toshiyuki Suzuki, Masao Imai, Kenichi Fujii
  • 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: 5731436
    Abstract: Processes for producing benzothiophenes employing ethylene carbonate or propylene carbonate are provided.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: March 24, 1998
    Assignee: Eli Lilly and Company
    Inventor: Douglas P. Kjell
  • Patent number: 5231219
    Abstract: Process for the manufacture of .alpha.-fluoroacrylates of general formula: ##STR1## with R' alkyl, aryl or cycloalkyl, according to which source of formalin, consisting of paraformaldehyde is reacted with an .alpha.-fluorophosphonoacetate in aqueous medium in the presence of a salt of a weak inorganic acid.
    Type: Grant
    Filed: July 2, 1992
    Date of Patent: July 27, 1993
    Assignee: Elf Atochem S.A.
    Inventors: Claude Grison, Nathalie Boulliung, Philippe Coutrot
  • Patent number: 5003102
    Abstract: 5-Formylvaleric esters are prepared by a process which comprises the following steps:(a) Hydroformylation of a pentenoic ester by reaction with carbon monoxide and hydrogen at elevated temperatures and under superatmospheric pressure in the presence of a carbonyl complex of a metal of group 8 of the Periodic Table with formation of a mixture of 5-, 4- and 3-formylvaleric esters,(b) Isolation of the 5-formylvaleric ester from the resulting mixture of 5-, 4- and 3-formylvaleric esters, a mixture essentially consisting of 4- and 3-formylvaleric esters remaining,(c) Cleavage of the mixture essentially consisting of 4- and 3-formylvaleric esters at from 50.degree. to 400.degree. C. in the presence of a catalyst to give pentenoic esters and(d) Recycling of the pentenoic esters to stage (a).
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: March 26, 1991
    Assignee: BASF Aktiensellschaft
    Inventors: Werner Bertleff, Rolf Fischer, Rudolf Kummer, Franz Merger, Heinz-Walter Schneider
  • Patent number: 4997955
    Abstract: 1,1-disubstituted ethylene compounds of the general formula I ##STR1## where Z is COOR.sup.2, CN or COR.sup.3, R.sup.1 is an aliphatic, cycloalophatic, araliphatic, aromatic or heterocyclic radical which may be further substituted by functional groups which are inert under the reaction conditions, R.sup.2 is an aliphatic, cycloaliphatic or araliphatic radical of 1 to 15 carbon atoms and R.sup.3 is an aliphatic, cycloaliphatic or araliphatic radical of 1 to 15 carbon atoms which may be substituted by groups which are inert under the reaction conditions, and R.sup.1 together with R.sup.2 or R.sup.1 together with R.sup.3 may furthermore form an alkylene chain of 2 to 10 carbon atoms which may be substituted by groups which are inert under the reaction conditions, are prepared from a formyl compound of the general formula II ##STR2## where Z, R.sup.1, R.sup.2 and R.sup.3 have the above meanings, by a process in which the reaction is carried out in the presence of formaldehyde or paraformaldehyde and(a) a C.sub.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: March 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Joerg Liebe, Werner Bertleff
  • Patent number: 4965401
    Abstract: The process for the preparation of the E isomers of the compounds of formula A: ##STR1## in which R.sub.1 is selected from H or C.sub.1 -C.sub.4 alkyl, comprises according to the invention the reaction of propionaldehyde with a phosphorus derivative of formula: ##STR2## in which R.sub.1 designates C.sub.1 -C.sub.4 alkyl and R.sub.2 is selected from C.sub.1 -C.sub.4 alkyl or phenyl, and, optionally, the hydrolysis of the compound of formula A in which R.sub.1 is alkyl in order to form the compounds of formula A in which R.sub.1 is H.Pharmaceutical industry.
    Type: Grant
    Filed: December 1, 1989
    Date of Patent: October 23, 1990
    Assignee: Sanofi
    Inventors: Marcel Descamps, Georges Sayac
  • Patent number: 4931590
    Abstract: Adipic acid is prepared by a process which comprises the following steps:(a) Hydroformylation of a pentenoic ester by reaction with carbon monoxide and hydrogen at elevated temperatures and under superatmospheric pressure in the presence of a cobalt carbonyl or rhodium carbonyl complex with formation of a mixture of 5-, 4- and 3-formylvaleric esters,(b) isolation of the 5-formylvaleric ester from the resulting mixture of 5-, 4- and 3-formylvaleric esters, a mixture essentially consisting of 4- and 3-formylvaleric esters remaining,(c) dehydrocarbonylation of the mixture consisting essentially of 4- and 3-formylvaleric esters in the presence of one or more elements of subgroup 8 of the Periodic Table at from 50.degree. to 400.degree. C.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: June 5, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Franz Merger, Werner Bertleff, Rolf Fischer
  • Patent number: 4822721
    Abstract: Halogen-containing polyacrylate derivatives having the formula: ##STR1## wherein A is a structural unit derived from a copolymeriazable monomer having a double bond; R is ##STR2## wherein each of R.sub.1 and R.sub.2 is a hydrogen atom or a fluorinated methyl group, provided R.sub.1 and R.sub.2 are not hydrogen atoms at the same time, and R.sub.3 is a hydrogen atom or a lower alkyl group; X is a halogen atom or a methyl group; and m is a positive integer, n is 0 or a positive integer, and n/m from 0 to 2, preferably from 0 to 1 are disclosed.Also disclosed are methods for forming a resist pattern by using the halogen-containing polyacrylate derivatives as a resist material.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: April 18, 1989
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Yoshitaka Tsutsumi, Toru Seita, Hideo Shuyama, Kousaburou Matsumura, Kyoko Nakazawa
  • Patent number: 4751307
    Abstract: Disclosed are improved Wittig reaction processes wherein the Wittig reaction is conducted in an anisole containing solvent.
    Type: Grant
    Filed: February 27, 1987
    Date of Patent: June 14, 1988
    Assignee: Mallinckrodt, Inc.
    Inventor: Carl R. White
  • Patent number: 4739111
    Abstract: A process for preparing a catalyst composition wherein a Metal Hydrocarboxide I, such as aluminum secbutoxide, a Metal Hydrocarboxide II, such as zirconium butoxide, an acidic phosphorus-oxygen composition, such as phosphoric acid, and water, are reacted in the presence of a liquid organic medium, such as acetone, to form a catalyst precursor composition, which is then calcined to form the catalyst, is disclosed. The catalyst is useful for condensing carboxylic acids or their ester with aldehydes or acetals to synthesize .alpha. ,.beta.-ethylenically unsaturated acids or esters, such as methylmethacrylate.
    Type: Grant
    Filed: September 11, 1985
    Date of Patent: April 19, 1988
    Assignee: Exxon Research & Engineering Co.
    Inventor: Ji-Yong Ryu
  • Patent number: 4591651
    Abstract: The invention concerns a process for directly converting an aldehyde into an ethylene ester, of the type wherein the aldehyde is placed in the presence of an alkaline carbonate or bicarbonate and of a phosphonate into a solvent with an alcohol function. In the invention, an ethyl phosphonate or a methyl phosphonate is used and the solvent is an alcohol or a polyol including a hydrocarbon radical other than ethyl or methyl, this radical being that of the ethylenic ester to be produced. The process of the invention makes it possible to directly convert furan aldehyde or tetrahydrofuran aldehyde to produce an ethylenic ester with a furan ring or a tetrahydrofuran ring.
    Type: Grant
    Filed: September 26, 1984
    Date of Patent: May 27, 1986
    Assignee: Agrifurane S.A.
    Inventors: Michel Delmas, Antoine Gaset, Yves Le Bigot
  • Patent number: 4581471
    Abstract: Unsaturated carboxylic acids and/or esters thereof are produced by reacting an aldehyde comprising formaldehyde or acetaldehyde with either a saturated carboxylic acid ester or anhydride in the vapor phase in the presence as catalyst of a high silica crystalline aluminosilicate zeolite in which the cation is H.sup.+ and/or a transition metal and/or a rare earth metal. In a modification of the process instead of formaldehyde there is used methanol/molecular oxygen and in the catalyst there is included either an oxidative or an oxidative/dehydrogenative component.
    Type: Grant
    Filed: April 9, 1984
    Date of Patent: April 8, 1986
    Assignee: The British Petroleum Company P.L.C.
    Inventors: Michael T. Barlow, David G. Stewart
  • Patent number: 4581472
    Abstract: A process for producing a perfluoroacrylic acid ester represented by the general formula CF.sub.2 .dbd.CFCOOR where R is a monovalent organic substituent, which comprises pyrolyzing a monoester of perfluorosuccinyl fluoride represented by the general formula FOCCF.sub.2 CF.sub.2 COOR where R is as defined above, in a vapor phase.
    Type: Grant
    Filed: October 19, 1983
    Date of Patent: April 8, 1986
    Assignee: Asahi Glass Company Ltd.
    Inventors: Shunichi Samejima, Isamu Kaneko
  • Patent number: 4560790
    Abstract: A process for preparing a catalyst composition wherein a Metal Hydrocarboxide I, such as aluminum secbutoxide, a Metal Hydrocarboxide II, such as silicon ethoxide, an acidic phosphorus-oxygen composition, such as phosphoric acid, and water, are reacted in the presence of a liquid organic medium, such as acetone, to form a catalyst precursor composition, which is then calcined to form the catalyst, is disclosed. The catalyst is useful for condensing carboxylic acids or their ester with aldehydes or acetals to synthesize .alpha., .beta.-ethylenically unsaturated acids or esters, such as methylmethacrylate.
    Type: Grant
    Filed: August 8, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventor: Ji-yong Ryu
  • 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