Aldehyde Reacted With Aldehyde Patents (Class 568/461)
  • Patent number: 11680033
    Abstract: A process and a preparation plant prepares methacrolein from formaldehyde and propionaldehyde, in presence of water and a homogeneous catalyst based at least on an acid and a base. A reaction mixture is introduced into a methacrolein workup plant and separated in a first distillation column, into a first distillation mixture in a gas phase at the top and a second distillation mixture in a liquid phase at the bottom. The first distillation mixture is condensed and, in a first phase separator, the organic phase and the aqueous phase of the condensate are separated from one another. The aqueous phase is introduced into a second distillation column, that is not part of the methacrolein workup plant, and is separated into a third distillation mixture in a gas phase at the top and a fourth distillation mixture at the bottom. The third distillation mixture is introduced into the methacrolein workup plant.
    Type: Grant
    Filed: August 20, 2020
    Date of Patent: June 20, 2023
    Assignee: Röhm GmbH
    Inventors: Rudolf Burghardt, Steffen Krill, Florian Zschunke, Eduard Rundal, Torsten Panak, Daniel Helmut König
  • Patent number: 10125077
    Abstract: The present invention relates to an optimized process for preparing methacrylic acid, wherein methacrolein is prepared in a first stage from propionaldehyde and formaldehyde by means of a Mannich reaction and oxidized in a second stage to methacrylic acid. More particularly, the present invention relates to the reduction in the amounts of catalyst to be used in the first stage, especially to the reduction in the amounts of acid to be used here, by virtue of the additional installation of recycling streams suitable for the purpose.
    Type: Grant
    Filed: November 16, 2015
    Date of Patent: November 13, 2018
    Assignee: Evonik Röhm GmbH
    Inventors: Steffen Krill, Rudolf Burghardt, Melanie Raczek, Torsten Balduf
  • Patent number: 9816703
    Abstract: The present invention relates to the oxidative combustion of amine-containing wastewaters, especially in a process for preparing methacrolein. Methacrolein is used in chemical synthesis particularly as an intermediate for preparation of methacrylic acid, methyl methacrylate, or else of active ingredients, odorants or flavorings. More particularly, the present invention relates to an oxidative combustion of the amine-containing wastewaters with only low nitrogen oxide formation.
    Type: Grant
    Filed: July 15, 2014
    Date of Patent: November 14, 2017
    Assignee: EVONIK ROEHM GmbH
    Inventors: Steffen Krill, Torsten Balduf, Rudolf Burghardt, Gerhard Koelbl, Reed Zhao
  • Patent number: 9676692
    Abstract: There is provided a novel intermediate for producing pesticides. A method for producing the compound of Formula (3) comprises reacting an aromatic ketone compound of Formula (4) and a substituted acetophenone compound of Formula (5) as starting raw materials in an organic solvent or water in the presence or absence of an additive in the presence of a base in a suspended state. A method may comprise dehydrating the compound of Formula (3). A method for producing compound (2) in one step comprises reacting compound (4) and compound (5) to obtain compound (3). Further, a method for producing an isoxazoline compound of Formula (1) comprises reacting compound (2) and a hydroxylamine in an aliphatic or an aromatic hydrocarbon solvent which is optionally substituted by a halogen atom by adding an additive selected from a phase-transfer catalyst, a C1-C6 alcohol and an aprotic polar solvent in the presence of a base and water.
    Type: Grant
    Filed: December 29, 2014
    Date of Patent: June 13, 2017
    Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Manabu Yaosaka, Tomohisa Utsunomiya, Yuji Moriyama, Tomohiro Matsumoto, Kazutaka Matoba
  • Patent number: 8841489
    Abstract: The invention relates to a continuous method for carrying out a multiphase aldol condensation reaction to obtain mixed ?,?-unsaturated aldehydes by reacting a mixture of two aliphatic aldehydes having different numbers of carbon atoms, i.e. 2 to 5, in the molecule in a vertical tubular reactor in a concurrent flow in the presence of an aqueous solution of a basically reacting compound. In said method, the aldehyde mixture is dispersed in the aqueous phase in the form of drops, and the aqueous solution of the basically reacting compound flows through the tubular reactor as a continuous phase in laminar conditions.
    Type: Grant
    Filed: February 9, 2012
    Date of Patent: September 23, 2014
    Assignee: Oxea GmbH
    Inventors: Dirk Bermann, Guido D. Frey, Norman Nowotny, Kurt Schalapski, Heinz Strutz
  • Patent number: 8809594
    Abstract: Disclosed is a process for the production of higher aldehydes from lower alcohols using a two-stage vapor phase heterogeneous catalyst system. Ethanol feeds afford aldehydes such as butyraldehyde and crotonaldehyde while butanol feeds yield 2-ethylhexanal and 2-ethylhexenal. Higher product selectivities are obtained when the alcohol is first dehydrogenated in the upper catalyst stage followed by aldol condensation of the resulting lower aldehyde to a higher aldehyde.
    Type: Grant
    Filed: September 21, 2012
    Date of Patent: August 19, 2014
    Assignee: Eastman Chemical Company
    Inventors: David William Norman, Damon Ray Billodeaux, Melissa Dawn Page
  • Patent number: 8686195
    Abstract: The present invention relates to a process for synthesizing acrolein, coupling the dehydration of glycerol into acrolein with a reaction for aldol condensation of acetaldehyde, produced in the form of an impurity during the dehydration, by means of formaldehyde.
    Type: Grant
    Filed: December 7, 2010
    Date of Patent: April 1, 2014
    Assignee: Arkema France
    Inventor: Jean Luc Dubois
  • Publication number: 20140005441
    Abstract: The invention relates to a continuous method for carrying out a multiphase aldol condensation reaction to obtain mixed ?, ?-unsaturated aldehydes by reacting a mixture of two aliphatic aldehydes having different numbers of carbon atoms, i.e. 2 to 5, in the molecule in a vertical tubular reactor in a concurrent flow in the presence of an aqueous solution of a basically reacting compound. In said method, the aldehyde mixture is dispersed in the aqueous phase in the form of drops, and the aqueous solution of the basically reacting compound flows through the tubular reactor as a continuous phase in laminar conditions.
    Type: Application
    Filed: February 9, 2012
    Publication date: January 2, 2014
    Applicant: Oxea GmbH
    Inventors: Dirk Bermann, Guido D. Frey, Norman Nowotny, Kurt Schalapski, Heinz Strutz
  • Patent number: 8581008
    Abstract: The invention relates to a method for continuously producing ?,?-unsaturated C10-aldehydes from aliphatic C5-aldehydes, comprising the following steps: aldol-condensing aliphatic C5-aldehydes into ?,?-unsaturated C10-aldehydes in the presence of an aqueous base in a tube reactor; phase separating the output of the tube reactor into an aqueous catalyst phase and an organic product phase; separating the organic product phase into ?,?-unsaturated C10-aldehydes, aliphatic C5-aldehydes, and auxiliary products; discharging a part of the aqueous catalyst phase to remove the reaction water and supplementing said part with liquor solution and subsequently returning said part to the tube reactor. The task of the invention is to improve a method of said kind in a way such that it requires lower energy input. This is achieved in that the aliphatic C5-aldehydes and/or the ?,?-unsaturated C10-aldehydes are dispersed in the aqueous base as drops, wherein the average Sauter diameter of the drops is between 0.2 mm and 2 mm.
    Type: Grant
    Filed: February 23, 2010
    Date of Patent: November 12, 2013
    Assignee: Evonik Oxeno GmbH
    Inventors: Alfred Kaizik, Dirk Fridag, Hans-Gerd Lueken, Wilfried Bueschken
  • Patent number: 8563782
    Abstract: The invention relates to a method for producing ?,?-unsaturated aldehydes, wherein a catalytic aldol condensation of charged aldehydes is carried out in the presence of an aqueous base within a continuous-flow reactor. The aim of the invention is to provide a method for aldolizing aldehydes that can be carried out in a particularly economical manner. The aim is achieved by using a reaction mixing pump as the reactor.
    Type: Grant
    Filed: August 3, 2010
    Date of Patent: October 22, 2013
    Assignee: Evonik Oxeno GmbH
    Inventors: Alfred Kaizik, Hans-Gerd Lueken, Dirk Fridag, Wilfried Bueschken, Dirk Mackowiak, Frank Brocksien
  • Publication number: 20120283479
    Abstract: The present invention relates to a process for synthesizing acrolein, coupling the dehydration of glycerol into acrolein with a reaction for aldol condensation of acetaldehyde, produced in the form of an impurity during the dehydration, by means of formaldehyde.
    Type: Application
    Filed: December 7, 2010
    Publication date: November 8, 2012
    Applicant: ARKEMA FRANCE
    Inventor: Jean Luc Dubois
  • Publication number: 20120190895
    Abstract: The invention relates to a method for producing ?,?-unsaturated aldehydes, wherein a catalytic aldol condensation of charged aldehydes is carried out in the presence of an aqueous base within a continuous-flow reactor. The aim of the invention is to provide a method for aldolizing aldehydes that can be carried out in a particularly economical manner. The aim is achieved by using a reaction mixing pump as the reactor.
    Type: Application
    Filed: August 3, 2010
    Publication date: July 26, 2012
    Applicant: Evonik Oxeno GmbH
    Inventors: Alfred Kaizik, Hans-Gerd Lueken, Dirk Fridag, Wilfried Bueschken, Dirk Mackowiak, Frank Brocksien
  • Patent number: 7767770
    Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source with a catalyst comprising synthetic cryptomelane or octahedral molecular sieve. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.
    Type: Grant
    Filed: September 17, 2009
    Date of Patent: August 3, 2010
    Assignee: Rohm and Haas Company
    Inventors: Scott Han, Daniel J. Martenak, Lei Jin, Steven Lawrence Suib
  • Patent number: 7732644
    Abstract: The present invention relates to processes for producing ?,?-unsaturated aldehyde compounds and unsaturated alcohols with a good yield. There is provided a process for producing and ?,?-unsaturated aldehyde compound including the step of subjecting a raw aldehyde compound to an intermolecular condensation reaction in the presence of an amine and a protonic acid having 4 to 20 carbon atoms or a salt thereof; and a process for producing an unsaturated alcohol including the step of subjecting the ?,?-unsaturated aldehyde compound to a reduction reaction.
    Type: Grant
    Filed: November 8, 2006
    Date of Patent: June 8, 2010
    Assignee: Kao Corporation
    Inventors: Kosaku Ishida, Shigeyoshi Tanaka, Takahiro Asada
  • Patent number: 7632973
    Abstract: Methods for preparing self-aldol condensation products of prenyl aldehyde (3-methyl-2-butenal) by use of an amine catalyst under weakly acidic conditions at temperatures of 10° C. or higher are disclosed. Methods are disclosed for the selective formation of ?-1,2-adducts and ?-1,2-adducts of prenyl aldehyde, and for the formation of specialty compositions useful in the flavor and fragrance industries.
    Type: Grant
    Filed: April 24, 2008
    Date of Patent: December 15, 2009
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 7402710
    Abstract: An industrial process for producing hydroxyaldehydes efficiently, by solving the problems of conventional DERA, such as low stability against aldehydes, low catalytic activity for aldol condensation, and the difficulty of controlling the number of acetaldehyde molecules to be condensed, is provided. According to the process, aldol condensation of a substituted or unsubstituted aliphatic aldehyde compound having 2 to 6 carbon atoms with acetaldehyde is conducted by using D-2-deoxyribose-5-phosphate aldolase which is highly stable against aldehydes and has high catalytic activity for aldol condensation, whereby a hydroxyaldehyde compound having the number of carbon atoms increased by two or four can be produced.
    Type: Grant
    Filed: March 28, 2005
    Date of Patent: July 22, 2008
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Kazuya Matsumoto, Yasushi Kazuno, Norikazu Higashimura, Toshihisa Ohshima, Haruhiko Sakuraba
  • Patent number: 7368612
    Abstract: The present invention provides a method of producing high-purity hydroxypivalaldehyde and/or dimer thereof, including: reacting isobutyl aldehyde with formaldehyde in a presence of a basic catalyst; distilling a low boiling point component including unreacted isobutyl aldehyde to obtain an aqueous solution; adding a diluent to the aqueous solution; cooling the aqueous solution to crystallize the hydroxypivalaldehyde and/or the dimer thereof; and subjecting the aqueous solution to a solid-liquid separation, followed by washing with an organic solvent and/or water, in which the diluent and a basic compound are added to the aqueous solution containing the hydroxypivalaldehyde and/or the dimer thereof obtained by distilling the low boiling point component off so that a concentration of the hydroxypivalaldehyde and/or the dimer becomes 5 to 23% by mass, the concentration of formaldehyde becomes 0.2 to 2.5% by mass, and a pH value becomes 5.0 or more, the solution is crystallized at a temperature of 20 to 45° C.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: May 6, 2008
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Junichi Amemiya, Masafumi Watanabe, Ikutaro Kuzuhara
  • Patent number: 7247755
    Abstract: The present invention provides a process for producing an ?,?-bis(hydroxymethyl)alkanal represented by Formula (II): (wherein R represents an alkyl group, a cycloalkyl group, or an aryl group) which comprises reacting an aldehyde represented by Formula (I): R—CH2—CHO ??(I) (wherein R has the same meaning as defined above) with formaldehyde in the presence of a basic catalyst and a phase-transfer catalyst.
    Type: Grant
    Filed: July 22, 2004
    Date of Patent: July 24, 2007
    Assignee: Kyowa Hakko Chemical Co., Ltd.
    Inventors: Shinichi Konishi, Shingo Nakayama, Yukihiro Isogai, Tokuyuki Yoshimoto
  • Patent number: 7141702
    Abstract: The present invention provides an improved process for the synthesis of ?-substituted acroleins from olefins by a tandem hydroformylation and Mannich reaction sequence in the presence of syngas and formaldehyde, wherein the two catalysts are segregated into two different phases thereby preventing deactivation of the catalysts by each other, and yielding a highly selective and active catalyst.
    Type: Grant
    Filed: March 26, 2004
    Date of Patent: November 28, 2006
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raj M. Deshpande, Makarand M. Diwakar, Raghunath V. Chaudhari
  • Publication number: 20040162447
    Abstract: The invention relates to 2-methyl-4-ethyl-2-octene-1-aldehyde of formula (I), which is characterized by interesting and original odor characteristics which diffuse extremely well. The inventive substance is suitable for use as fragrance, for example in cosmetic preparations, technical products or in alcoholic perfumery.
    Type: Application
    Filed: March 30, 2004
    Publication date: August 19, 2004
    Inventors: Thomas Markert, Ralph Nemitz, Marc Speitkamp, Theo Ten Pierik, Markus Schneider, Ralph Bunn
  • Patent number: 6586636
    Abstract: Production of unsaturated aldehydes by the aldol condensation of straight chain aldehydes, e.g. butyraldehyde, by contacting the aldehyde in the vapour phase with a particulate catalyst comprising at least one basic alkali metal compound supported on an inert substrate at a temperature above 175° C.
    Type: Grant
    Filed: May 22, 2001
    Date of Patent: July 1, 2003
    Assignee: Imperial Chemical Industries PLC
    Inventor: Gordon James Kelly
  • Patent number: 6555716
    Abstract: Aldehydes are prepared in a hydroformylation apparatus by the multiphase hydroformylation reaction of one or more olefins with hydrogen and carbon monoxide, where the continuous phase contains a solvent mixture and the hydroformylation catalyst is present in the continuous phase, at least one olefin is present in the dispersed phase, and the loading factor of the tube reactor is greater than or equal to 0.8.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: April 29, 2003
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Guido Protzmann, Klaus-Diether Wiese, Wilfried Büschken, Dirk Röttger
  • Patent number: 6437190
    Abstract: A process for preparing aldols by catalytic reaction of aldehydes and/or ketones comprises conducting said reaction in the channels of a microstructured reaction system.
    Type: Grant
    Filed: November 2, 2001
    Date of Patent: August 20, 2002
    Assignee: Siemens Axiva GmbH & Co. KG
    Inventors: Inga Leipprand, Thorsten Lahrs
  • Patent number: 6433230
    Abstract: &agr;,&bgr;-Unsaturated keto compounds are prepared by base-catalyzed aldol condensation of aldehydes and/or ketones having from 1 to 15 carbon atoms, comprising: reacting the aldehydes and/or ketones with an aqueous catalyst solution under adiabatic reaction conditions; and separating the reaction mixture obtained by rapid distillation into a top product comprising water, aldehyde and/or ketone and a bottom product comprising &agr;,&bgr;-unsaturated keto compounds and aqueous catalyst phase.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: August 13, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann
  • Patent number: 6380443
    Abstract: A process for preparing 1,3-diols having 6 or more carbon atoms comprises a) provision of at least one alkanal having at least three carbon atoms; b) thermal treatment of the alkanal in the absence of a basic catalyst; c) hydrogenation of the aldol addition product formed in step b); and d) isolation of the 1,3-diol obtained. The process of the present invention makes it possible to prepare 1,3-diols simply and inexpensively.
    Type: Grant
    Filed: October 3, 2000
    Date of Patent: April 30, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Detlef Kratz, Harald Rust, Roland Krokoszinski, Volker Helf
  • Patent number: 6340778
    Abstract: The invention relates to a process for the catalytic aldol condensation of aldehydes by means of a multiphase reaction in a tube reactor, wherein the catalyst is present in the continuous phase and at least one aldehyde is present in a dispersed phase and the loading factor B of the tube reactor is equal to or greater than 0.8; the aldol condensation products obtained in this way can be used for preparing alcohols or carboxylic acids.
    Type: Grant
    Filed: October 24, 2000
    Date of Patent: January 22, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann, Juergen Koch
  • Patent number: 5994592
    Abstract: The present invention relates to a process for producing 2,2'-bis(hydroxymethyl)alkanal and 2,2'-bis(hydroxymethyl)alkanoic acid as raw materials for dimethylol alkanoic acids or trimethylol alkanes, which are useful for the production of polyesters, polyurethanes, alkyd resins and the like, in an industrially advantageous manner.
    Type: Grant
    Filed: February 12, 1998
    Date of Patent: November 30, 1999
    Assignee: Nippon Kasei Chemical Company Limited
    Inventors: Toshiharu Yokoyama, Kouji Maeda
  • Patent number: 5888923
    Abstract: The present invention relates to a modified Raney nickel catalyst which can serves as hydrogenation catalyst for hydroxy aldehydes, such as 4-hydroxy-butanal, and 2-methyl-3-hydroxypropanal and hydroxy cyclic ethers such as 2-hydroxy-tetrahydrofuran. Further, a process for preparing diols by using the modified Raney nickel catalyst is provided.
    Type: Grant
    Filed: April 15, 1996
    Date of Patent: March 30, 1999
    Assignee: Dairen Chemical Corporation
    Inventors: Shien Chang Chen, C. C. Chu, F. S. Lin, J. Y. Chou, C. C. Huang
  • Patent number: 5663452
    Abstract: The invention relates to a new, technically simple but efficient process, with a good yield, for the preparation of 2-ethyl-1,3-hexane diol from n-butyraldehyde by aldol condensation in the presence of an alkali metal hydroxide or alkali earth metal hydroxide catalyst. To promote the reaction and to improve its controllability, a neutral phase-transfer catalyst is additionally used in the process according to the invention. 2-Ethyl-1,3-hexane diol is used in insecticides and, for example, in the preparation of polyesters.
    Type: Grant
    Filed: May 3, 1996
    Date of Patent: September 2, 1997
    Assignee: Neste OY
    Inventors: Kari Kulmala, Kjell Ankner, Lea Rintala, Leila Lahtinen, Kalevi Heinola
  • Patent number: 5434313
    Abstract: An aldolisation-dehydration process is disclosed for converting an aldehyde, e.g. n-valeraldehyde, to a substituted acrolein, e.g. propyl butyl acrolein (2-propylhept-2-enal). Aldolisation and dehydration are effected in a stirred tank reactor (16; 111) using an alkali catalyst, such as sodium hydroxide. A reaction product stream (23; 113) containing both organic and aqueous phases is distilled (in column 25; 123) to yield a heterogeneous azeotrope containing water and aldehyde. On condensation and phase separation the lower water layer (34; 150) can be discharged from the plant without the need for neutralisation. From the bottom of the distillation zone a mixture (36;157) of substituted acrolein and alkali catalyst solution is obtained. The substituted acrolein is recovered as product (45;173), while the catalyst solution (47;175) is recycled to the aldolisation reactor. Part (49; 181) of the catalyst solution is purged to control the level of Cannizzaro reaction products.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: July 18, 1995
    Assignee: Davy McKee (London) Limited
    Inventors: George E. Harrison, Arthur J. Reason, Alan J. Dennis, Mohammad Sharif
  • Patent number: 5386062
    Abstract: A process for the catalytical preparation of condensation products of formaldehyde, in which formaldehyde or a formaldehyde-forming compound is caused to undergo reaction using a catalyst which has been produced, in the presence of an auxiliary base, from a triazolium salt of formula I ##STR1## in which R.sup.1 and R.sup.3 are the same or different and stand for aliphatic groups having from 1 to 30 carbon atoms, optionally substituted aryl groups, optionally substituted aralkyl groups, and/or optionally substituted heteroaryl groups,R.sup.2 represents hydrogen, the hydroxymethylene group --CH.sub.2 OH or the hydroxy-hydroxymethylene-methylidyne group --CH(OH)(CH.sub.2 OH), andR.sup.4 denotes hydrogen, a halogen atom, a nitro or cyano group, an aliphatic group having from 1 to 30 carbon atoms, an optionally substituted aryl group, an optionally substituted aralkyl group, an optionally substituted heteroaryl group, an alkoxy group --OR.sup.5, a thioether group --SR.sup.6, an amino group --NR.sup.7R R.sup.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: January 31, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Joaquim H. Teles, Johann-Peter Melder, Eugen Gehrer, Wolfgang Harder, Klaus Ebel, Carsten Groening, Regina Meyer
  • Patent number: 5382700
    Abstract: A process for producing dimeric unsaturated aldehydes from alpha, beta unsaturated aldehyde is disclosed. This process is conducted by contacting the alpha, beta unsaturated aldehyde with a copper (II) catalyst and a complexing amine catalyst in a medium with a relatively high dielectric constant in substantially anhydrous and aprotic conditions.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: January 17, 1995
    Assignee: Eastman Chemical Company
    Inventor: William A. Beavers
  • Patent number: 5371299
    Abstract: Preparation of diethers of the formula ##STR1## wherein R is an alkyl, cycloalkyl, aryl, or aralkyl radical, by formation of an unsaturated aldehyde of the formula ##STR2## wherein R is as defined above, by means of an aldol condensation reaction, reduction of said aldehyde to form the corresponding saturated compound, transformation of the saturated compound into the corresponding diol, and consequent methylation of the diol into diether.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: December 6, 1994
    Assignee: Himont Incorporated
    Inventor: Giampietro Borsotti
  • Patent number: 5254742
    Abstract: A process for preparing 2-hexene-1,6-dial comprising dimerizing 2-propenal in the presence of an organometallic compound of the group VIII metal. The desired compound can be obtained under mild conditions with industrial advantages.
    Type: Grant
    Filed: October 8, 1992
    Date of Patent: October 19, 1993
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Yuji Ohgomori, Shuji Ichikawa, Takahiro Yoneyama, Naoko Sumitani
  • Patent number: 5254743
    Abstract: Solid solutions of a class of divalent metal oxides and a class of trivalent metal oxides resulting from calcination of layered double hydroxides related to hydrotalcite have been prepared with a surface area in excess of 150 m.sup.2 /g. Such high surface area materials are found to be quite effective in the aldol condensation of aldehydes and ketones, and in particular in the conversion of n-butyraldehyde to 2-ethyl-2-hexenal in high yield and with good selectivity in a liquid phase reaction at temperatures under about 200.degree. C. Variants can be devised where the aldol condensation product, an .alpha.,.beta.-unsaturated aldehyde or ketone, is concurrently reduced to the saturated alcohol under process conditions.
    Type: Grant
    Filed: December 9, 1992
    Date of Patent: October 19, 1993
    Assignee: UOP
    Inventors: Jennifer S. Holmgren, Blaise J. Arena
  • Patent number: 5162552
    Abstract: A process for the preparation of 4-acetals of butene-1,4-dial of the formula ##STR1## where R is an alkyl, alkenyl, cycloalkyl or aralkyl radical of 1 to 12 carbon atoms which may contain alkoxy groups, or the two radicals R together form an alkylene or alkenylene radical of 2 to 10 carbon atoms which may contain alkoxy groups, and R.sup.1 is an alkyl, alkenyl or alkynyl radical of 1 to 12 carbon atoms which may be substituted by cycloaliphatic, aromatic or heterocyclic radicals or by hydroxyl, ether, thioether, acyl, alkylamino, carboxyl or carbalkoxy groups, or is an unsubstituted or substituted aryl radical or an alkoxy, alkylthio or acyloxy group, wherein a glyoxal monoacetal of the formula ##STR2## is reacted with an aldehyde of the formulaR.sup.1 --CH.sub.2 --CHO IIIat up to 150.degree. C., and novel acetals of butene-1,4-dial.
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: November 10, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Rolf Fischer, Hans Horler, Juergen Frank
  • Patent number: 5055620
    Abstract: Basic mixed oxides useful for base catalyzed reactions such as the aldol condensation of acetone and also useful as catalyst supports are made by mixing an acid such as nitric acid or acetic acid with a pseudoboehmite to form a gel, adding magnesium oxide or hydroxide, in a ratio of magnesium to aluminum of about 1:1 to about 10:1, agitating and heating for about 1 to 24 hours, and subsequently drying and calcining. The resulting polymorphic magnesium-aluminum oxide composition is hightly effective in the aldol condensation of acetone to isophorone, and other base catalyzed reactions such as isomerization of olefins, aldol condensation of aldehydes.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: October 8, 1991
    Assignee: Aristech Chemical Corporation
    Inventor: Alain A. Schutz
  • Patent number: 4943663
    Abstract: A process for the preparation of alpha-alkylacroleins from aldehydes and formaldehyde. The reaction takes place in the presence of a secondary amine and a carboxylic acid having up to 5 carbon atoms, and is performed in two stages so that, in the first stage, part of the carboxylic acid is added to the reaction mixture and, in the second stage, the remaining carboxylic acid is added.
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: July 24, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Diekhaus, Harald Kappesser
  • Patent number: 4851592
    Abstract: A process for producing neopentyl glycol is disclosed which comprises reacting isobutyraldehyde and formaldehyde in the presence of a trialkylamine catalyst to form a condensation reaction product comprising hydroxypivaldehyde, followed by hydrogenation of the hydroxypivaldehyde in a hydrogen gas sparged reactor in the presence of a Raney nickel catalyst. This process minimizes unwanted by-products, and does not have to be carried out under high pressure as do certain prior art methods.
    Type: Grant
    Filed: October 27, 1987
    Date of Patent: July 25, 1989
    Assignee: Eastman Kodak Company
    Inventor: Don L. Morris
  • Patent number: 4835320
    Abstract: This process for the preparation of products of general formula (I): ##STR1## wherein either R.sub.1 and R.sub.2, which are identical, represent a --CHRR.sub.3 group, in which R and R.sub.3, which are identical or different, represent an alkyl, alkenyl or aralkyl group, or R.sub.1 and R.sub.2, which are identical, represent a --CH.sub.2 R group, in which R represents a hydrogen atom, an alkyl, alkenyl or aralkyl radical, or R.sub.1 and R.sub.2 together form a --CH.sub.2 --(CRR).sub.n --CHR-- radical, in which n represents 0 or 1 and R retains the meaning given previously, is characterized by reacting glyoxal in the presence of an acid catalyst with an excess of the corresponding alcohol of general formula (II) RR.sub.3 CHOH, (III) RCH.sub.2 OH or (IV) --(CRR).sub.n --CHROH, in which R, R.sub.3 and n retain the meaning given previously, then stopping the reaction as soon as the concentration of the desired monoacetal of general formula (I) decreases in the reaction medium in favor of bisacetal.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: May 30, 1989
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Blanc, Farid Hamedi-Sangsari, Francine J. Chastrette
  • Patent number: 4740639
    Abstract: The invention relates to a process for the preparation of 2,4-disubstituted-1,5-pentanediols from formaldehyde and at least one simple aldehyde of the formula RCH.sub.2 CHO. More particularly the invention relates to a reaction to produce a 2,4-disubstituted glutaraldehyde wherein the reactant mole ratio of aldehyde/formaldehyde is between 1 and 8. The reaction is carried out in the presence of a secondary amine or secondary amine salt catalyst and leads to higher yields of the 2,4-disubstituted glutaraldehyde. The invention also relates to the production of 2,4-disubstituted-1,5-pentanediols by hydrogenation of the 2,4-disubstituted glutaraldehydes.
    Type: Grant
    Filed: June 12, 1987
    Date of Patent: April 26, 1988
    Assignee: Eastman Kodak Company
    Inventor: William A. Beavers
  • 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: 4714784
    Abstract: The invention relates to a method for removing n-butyraldehyde from gas streams. It is characterized by washing with dilute aqueous alkali in a mass transfer apparatus. According to the invention, n-butyraldehyde can be removed from gas streams in the proportion of >90%, with operation at 0.degree.-40.degree. C. in the absence of added solubilizing agents.
    Type: Grant
    Filed: July 16, 1986
    Date of Patent: December 22, 1987
    Assignee: Huls Aktiengesellschaft
    Inventors: Eckhard Moeller, Wolfgang H. E. Mueller, Manfred Z. Hausen
  • Patent number: 4701562
    Abstract: Aldehydes can be condensed with ketones or aldehydes to produce higher aldehydes or ketones by contacting the materials to be condensed with a nonzeolitic molecular sieve. The condensation may be carried out in the presence of hydrogen to give as product a saturated aldehyde or ketone. The ketone and/or aldehyde may be generated in situ by dehydrogenation of an alcohol, and the hydrogen thus liberated used to effect hydrogenation of the immediate unsaturated product of the condensation, thereby producing as the final product a saturated aldehyde or ketone. The non-zeolitic molecular sieves can achieve improved conversion rates and selectivities as compared with conventional catalysts for the reaction.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: October 20, 1987
    Assignee: Union Carbide Corporation
    Inventor: Kurt D. Olson
  • Patent number: 4683342
    Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities thereof, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnemaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, Cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in aqueous media and in the presence of a food grade or natural nonionic emulisifier, preferably a nonionic sorbitan derivative emulsifying agent and in the absence of any other reagents.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: July 28, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Arthur L. Liberman
  • Patent number: 4617419
    Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities therefor, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in the absence of any other reagents except inert solvent.
    Type: Grant
    Filed: September 26, 1985
    Date of Patent: October 14, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Charles Wiener, Alan O. Pittet
  • 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: 4526884
    Abstract: Catalyst composition and process are provided for the dimerization of acrylic compounds. An acrylic compound may be dimerized in the liquid phase by contacting an acrylic compound with a catalyst in the presence of hydrogen, at a pressure of least about 1 psi and a temperature of at least about 50.degree. C., wherein the catalyst comprises an organic polymer catalyst support, trivalent pendant atoms covalently bonded to the support, ruthenium complexed with said trivalent pendant atoms, and a second metal which is at least one of Pb and the Group VIII metals other than Ru and Pd and is disposed on the organic polymer catalyst support.
    Type: Grant
    Filed: December 27, 1982
    Date of Patent: July 2, 1985
    Assignee: The Standard Oil Company
    Inventors: Dean T. Tsou, James D. Burrington, Elizabeth A. Maher, Robert K. Grasselli
  • Patent number: 4519954
    Abstract: A catalyst and a liquid phase process are provided for the dimerization of acrylic compounds. The process includes contacting an acrylic compound with the catalyst in the presence of hydrogen, wherein the catalyst comprises an inorganic oxide catalyst support, trivalent pendant atoms covalently bonded to the support and ruthenium complexed with said trivalent pendant atoms.
    Type: Grant
    Filed: December 29, 1982
    Date of Patent: May 28, 1985
    Assignee: The Standard Oil Company
    Inventors: James D. Burrington, Fred A. Pesa, Elizabeth A. Maher, Robert K. Grasselli
  • Patent number: 4496770
    Abstract: .alpha.-Alkylacroleins are prepared by a process wherein an alkanal is reacted with formaldehyde in the presence of a secondary amine and in the presence or absence, of an acid, in the liquid phase, under superatmospheric pressure and at above 150.degree. C., for not more than 25 minutes.The .alpha.-alkylacroleins obtainable by the process are useful starting materials for dyes, drugs and pesticides.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: January 29, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Duembgen, Gerd Fouquet, Richard Krabetz, Ekhart Lucas, Franz Merger, Friedbert Nees