Of Aldehyde Or Ketone Patents (Class 568/862)
  • Patent number: 10759726
    Abstract: A process for the preparation of ethylene glycol and other C1-C3 hydroxy compounds comprising the steps of hydrogenating a composition comprising C1-C3 oxygenate compounds. In particular the process is suitable for hydrogenating a composition comprising different C1-C3 oxygenate compounds, such as the product from a thermolytic fragmentation of a sugar composition.
    Type: Grant
    Filed: January 5, 2017
    Date of Patent: September 1, 2020
    Assignee: HALDOR TOPSØE A/S
    Inventors: Martin Spangsberg Holm, Christian Mårup Osmundsen, Esben Taarning, Amanda Birgitte Sølvhøj, Morten Boberg Larsen
  • Patent number: 10752568
    Abstract: The present disclosure provides a method for preparing 1,3-propanediol by hydrolysis hydrogenolysis of glycerol and its corresponding reaction system, wherein, this method is to produce 1,3-propanediol through contact and reaction between hydrogen and glycerol under the catalysis of a noble metal/solid acid catalyst; wherein an auxiliary agent is contained in the liquid phase of the reaction system, and the content of the auxiliary agent in the liquid phase is 10 ppm or more.
    Type: Grant
    Filed: June 17, 2019
    Date of Patent: August 25, 2020
    Assignee: Zhangjiagang Glory Chemical Industry Co., Ltd.
    Inventors: Changlin Chen, Xiaodong Zhu, Bing Han, Chengchao Xiao
  • Patent number: 10144687
    Abstract: An object of the present invention is to provide an industrially advantageous production method of 1,4BG, ensuring that generation of THF in the crude 1,4BG can be also suppressed and at the same time, the concentration of 2-(4-hydroxybutoxy)-tetrahydrofuran can be reduced. The present invention relates to a method for producing 1,4-butanediol, comprising heating crude 1,4-butanediol containing from 0.01 to 0.5 wt % of 2-(4-hydroxybutoxy)-tetrahydrofuran and from 1 to 25 wt % of water at 80° C. or more in the presence of an amine to obtain purified 1,4-butanediol.
    Type: Grant
    Filed: January 6, 2014
    Date of Patent: December 4, 2018
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Yusuke Izawa, Masaru Utsunomiya, Kouta Tanaka, Norikazu Konishi
  • Patent number: 9914684
    Abstract: Allyl alcohol production processes are generally described herein. One or more of the processes generally include contacting a propylene oxide stream with an isomerization catalyst under isomerization conditions sufficient to form an isomerization product stream including allyl alcohol, wherein the propylene oxide stream includes a total impurity concentration of at least 100 ppm. One or more of the processes generally includes purging at least a portion of a stream from one or more separation unit(s).
    Type: Grant
    Filed: November 16, 2016
    Date of Patent: March 13, 2018
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Sarthak Gaur, Beaven S. Mandimutsira, Daniel F. White, Walter S. Dubner
  • Patent number: 9783472
    Abstract: A continuous process for converting carbohydrates to ethylene and propylene glycol. The carbohydrates are mixed with water and passed through a reactor at a temperature that hydrolyzes the carbohydrate mixture at least partially to monosaccharides. The reactor has a first zone comprising a retro-aldol catalyst and a second zone comprising a reducing catalyst. The aldose is converted in the first zone into glycolaldehyde by the retro-aldol catalyst and the glycolaldehyde, in the presence of hydrogen, is converted to ethylene glycol in the second zone of the reactor. The reaction products are removed from the reactor and the ethylene glycol is recovered. The selectivity to propylene glycol can be enhanced via feeding ketose as the carbohydrate.
    Type: Grant
    Filed: June 22, 2016
    Date of Patent: October 10, 2017
    Assignee: Iowa Corn Promotion Board
    Inventors: David James Schreck, Ray Chrisman, Brooke Albin, Nye Atwood Clinton, Marion McKinley Bradford
  • Patent number: 9353032
    Abstract: A method for preparing neopentyl glycol by addition of isobutyraldehyde and formaldehyde in the presence of a tertiary alkylamine as catalyst to give hydroxypivalaldehyde with subsequent hydrogenation at a temperature of 80 to 140° C. and at a pressure of 2 to 18 MPa in the liquid phase, is characterized in that the hydrogenation is carried out in the presence of a copper chromite catalyst comprising the activators barium and manganese.
    Type: Grant
    Filed: September 28, 2013
    Date of Patent: May 31, 2016
    Assignee: OXEA GMBH
    Inventors: Matthias Eisenacher, Kurt Schalapski, Heinz Strutz
  • Patent number: 9126912
    Abstract: A process for preparing ethylene glycol comprising: forming intermediums of formaldehyde and glycolaldehyde to synthetize ethylene glycol by reacting methanol with methanol in the presence of a catalyst composition comprising rhodium catalysts and ruthenium catalysts at a temperature between 50-150° C. and a pressure between 0-40 kg/cm2G.
    Type: Grant
    Filed: August 20, 2014
    Date of Patent: September 8, 2015
    Inventors: Chien-An Chen, Yi-Wen Chen
  • Patent number: 9056824
    Abstract: An improved process for preparing hydroxy aldehydes, such as hydroxypivaldehyde, is provided. Specifically, the process employs an alkaline additive for separating by-product amine salts from a hydroxy aldehyde and other reaction products formed in the process of preparing a hydroxy aldehyde using an amine catalyst.
    Type: Grant
    Filed: January 31, 2013
    Date of Patent: June 16, 2015
    Assignee: Eastman Chemical Company
    Inventors: Kenneth Wayne Hampton, Jr., Eugene H. Brown
  • Patent number: 8969632
    Abstract: A process for making ethylene glycol by feeding reactants including 1,2-dioxygenated organic compounds, an organometallic homogeneous catalyst, and hydrogen to a hydrogenation reactor, reacting at least a portion of the reactants with hydrogen in the presence of the organometallic homogeneous catalyst to produce a reaction product mixture containing ethylene glycol, and passivating the catalyst by contacting the catalyst with a carbon monoxide to thereby suppress the formation of by-product diols other that the ethylene glycol primary product, and suppress the formation of by-product tetrols and by-product glycolaldehyde acetals; and separating at least a portion of the ethylene glycol from the reaction product mixture.
    Type: Grant
    Filed: March 23, 2012
    Date of Patent: March 3, 2015
    Assignee: Eastman Chemical Company
    Inventors: David William Norman, Jonathan Michael Penney, Peter Borden Mackenzie
  • Patent number: 8962894
    Abstract: Disclosed are processes for preparing 1,6-hexanediol and synthetic intermediates useful in the production of 1,6-hexanediol from renewable biosources. In one embodiment, a process comprises contacting levoglucosenone with hydrogen in the presence of a first hydrogenation catalyst at a first temperature to form product mixture (I); and heating product mixture (I) in the presence of hydrogen and a second hydrogenation catalyst at a second temperature to form product mixture (II) which comprises 1,6-hexanediol.
    Type: Grant
    Filed: December 28, 2012
    Date of Patent: February 24, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta, Christina S Stauffer
  • Patent number: 8937202
    Abstract: Processes and systems for converting glycerol to propylene glycol are disclosed. The glycerol feed is diluted with propylene glycol as the primary solvent, rather than water which is typically used. The diluted glycerol feed is sent to a reactor where the glycerol is converted to propylene glycol (as well as other byproducts) in the presence of a catalyst. The propylene glycol-containing product from the reactor is recycled as a solvent for the glycerol feed.
    Type: Grant
    Filed: February 23, 2010
    Date of Patent: January 20, 2015
    Assignee: Battelle Memorial Institute
    Inventors: John G. Frye, Aaron A. Oberg, Alan H. Zacher
  • Patent number: 8933277
    Abstract: A process is provided for recovering components from a low boiler mixture which is obtained in the distillation of hydrogenation effluents from the preparation of polymethylols, by multistage distillation of the low boiler mixture having a tertiary amine, water, methanol, a polymethylol, a methylolalkanal, an alcohol and an alkanal with a methylene group in the alpha position to the carbonyl group. A first distillation stage involves separating the low boiler mixture into a higher-boiling, predominantly water-rich fraction and into a lower-boiling aqueous organic fraction having the tertiary amine. A second distillation stage involves separating the aqueous organic fraction from the first distillation stage into a predominantly amine-containing fraction and a further amine-depleted fraction. The tertiary amine is trimethylamine or triethylamine and the bottom temperature in the second distillation stage is at least 110° C.
    Type: Grant
    Filed: January 7, 2010
    Date of Patent: January 13, 2015
    Assignee: BASF SE
    Inventors: Stephan Schlitter, Michael Steiniger, Stefan Rittinger, Tilman Sirch, Steffen Maas
  • Patent number: 8921616
    Abstract: An object of the invention is to provide a production method that can produce glycol from polyhydric alcohol with high selectivity and in a satisfactory yield. The object is achieved by using a silver catalyst in a reaction for synthesizing hydroxyketone from polyhydric alcohol having adjacent hydroxyl groups, and a hydrogenation catalyst in a reaction for synthesizing glycol from hydroxyketone.
    Type: Grant
    Filed: January 12, 2012
    Date of Patent: December 30, 2014
    Assignees: Clariant Catalysts (Japan) K.K., National University Corporation Chiba University
    Inventors: Tetsuro Kizaki, Keizo Iwatani, Xin Chen, Satoshi Sato
  • Patent number: 8921617
    Abstract: A process for the preparation of 1,2-pentanediol by reaction of a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural with hydrogen in the presence of a first heterogeneous catalyst is described.
    Type: Grant
    Filed: May 9, 2012
    Date of Patent: December 30, 2014
    Assignee: Symrise AG
    Inventors: Oskar Koch, Angela Köckritz, Michael Kant, Andreas Martin, Axel Schöning, Udo Armbruster, Michael Bartoszek, Sigrid Evert, Brigitte Lange, Regina Bienert
  • Patent number: 8889922
    Abstract: Disclosed are processes for preparing 1,6-hexanediol from levoglucosenone. In one embodiment, the process comprises contacting levoglucosenone with hydrogen in the presence of a hydrogenation catalyst comprising palladium, platinum/tungsten, nickel/tungsten, rhodium/rhenium, or mixtures thereof at a first temperature between about 50° C. and 100° C. and at a first reaction pressure between about 50 psi and 2000 psi for a first reaction period, and at a second temperature between about 120° C. and 250° C. and at a second pressure between about 500 psi and 2000 psi for a second reaction period to form a product mixture comprising 1,6-hexanediol, wherein the first reaction period is the amount of time in which the levoglucosenone has a conversion of at least about 95%.
    Type: Grant
    Filed: December 28, 2012
    Date of Patent: November 18, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, David Richard Corbin, Wathudura Indika Namal De Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta
  • Patent number: 8853458
    Abstract: Processes are disclosed for the conversion of a carbohydrate source to hexamethylenediamine (HMDA) and to intermediates useful for the production of hexamethylenediamine and other industrial chemicals. HMDA is produced by direct reduction of a furfural substrate to 1,6-hexanediol in the presence of hydrogen and a heterogeneous reduction catalyst comprising Pt or by indirect reduction of a furfural substrate to 1,6-hexanediol wherein 1,2,6-hexanetriol is produced by reduction of the furfural substrate in the presence of hydrogen and a catalyst comprising Pt and 1,2,6-hexanediol is then converted by hydrogenation in the presence of a catalyst comprising Pt to 1,6 hexanediol, each process then proceeding to the production of HMDA by known routes, such as amination of the 1,6 hexanediol. Catalysts useful for the direct and indirect production of 1,6-hexanediol are also disclosed.
    Type: Grant
    Filed: January 11, 2013
    Date of Patent: October 7, 2014
    Assignee: Rennovia, Inc.
    Inventors: Eric L. Dias, James A. W. Shoemaker, Thomas R. Boussie, Vincent J. Murphy
  • Patent number: 8853465
    Abstract: The present invention relates to a process for preparing neopentyl glycol (NPG) by continuously hydrogenating hydroxypivalaldehyde (HPA) with hydrogen, in the liquid phase, in the presence of a hydrogenation catalyst, in a hydrogenation reactor (5), by combining an HPA-comprising stream (1) with an NPG-comprising stream (2) to give a hydrogenation feed (4) and introducing the hydrogenation feed (4) into the hydrogenation reactor (5) and additionally supplying at least one pH regulator (3) selected from the group consisting of tertiary amine, an inorganic base, an inorganic acid and an organic acid to the HPA-comprising stream (1) or the NPG-comprising stream (2) or the hydrogenation feed (4), in order to establish a pH of 7.0 to 9.
    Type: Grant
    Filed: May 11, 2011
    Date of Patent: October 7, 2014
    Assignee: BASF SE
    Inventors: Michael Steiniger, Maria Guixa Guardia, Kai Stehmeier
  • Publication number: 20140275371
    Abstract: The present invention relates to a process for preparing olefin-CO terpolymers with the steps of: providing a reactor; charging the reactor with a first, gaseous olefin and with CO, such that there is a first pressure p1 in the reactor; reacting the first olefin with CO in the presence of a catalyst in the reactor; wherein a second olefin is initially charged in the reactor and/or metered in during the reaction, prior to the reaction either no CO is present in the reactor or the volume ratio of first, gaseous olefin to CO is >60:40, and during the reaction the average over time of the volume ratio of gaseous olefin metered in to CO metered in is >60:40.
    Type: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: Bayer Intellectual Property GmbH
    Inventors: Thomas Ernst Müller, Christoph Gürtler, Walter Leitner, Henning Vogt, Saeeda Soomro
  • Publication number: 20140213827
    Abstract: An improved process for preparing hydroxy aldehydes, such as hydroxypivaldehyde, is provided. Specifically, the process employs an alkaline additive for separating by-product amine salts from a hydroxy aldehyde and other reaction products formed in the process of preparing a hydroxy aldehyde using an amine catalyst.
    Type: Application
    Filed: January 31, 2013
    Publication date: July 31, 2014
    Applicant: Eastman Chemical Company
    Inventors: Kenneth Wayne Hampton, JR., Eugene H. Brown
  • Patent number: 8710278
    Abstract: A process for producing polyols (such as neopentyl glycol) is disclosed which comprises reacting formaldehyde and another aldehyde in the presence of a trialkylamine catalyst and a base promoter to form an Aldol condensation reaction product. The base promoter improves removal of nitrogen containing salts prior to hydrogenation of the hydroxy aldehyde to produce the polyol. The improved process also reduces trialkylamine catalyst usage, improves trialkylamine catalyst recovery, and reduces nitrogen-containing salts prior to hydrogenation.
    Type: Grant
    Filed: January 31, 2013
    Date of Patent: April 29, 2014
    Assignee: Eastman Chemical Company
    Inventors: Kenneth Wayne Hampton, Jr., Eugene H. Brown, Thomas K. Brown, Amy K. Paris, Kevin S. Howe, Thomas Allen Puckette
  • Patent number: 8664448
    Abstract: The present invention relates to a process for producing an odorless and colorless industrial grade propylene glycol from glycerol obtained during the manufacturing of biodiesel. The process includes hydrogenating the glycerol to form a hydrogenated product, distilling the hydrogenated product to form a glycol product, and contacting the glycol product with a treatment bed. The propylene glycol may be used in various industrial and consumer applications and products such as personal care products.
    Type: Grant
    Filed: June 2, 2009
    Date of Patent: March 4, 2014
    Assignee: Huntsman Petrochemical LLC
    Inventors: Srinivasa Godavarthy, Wei-Yang Su, Ralph M. DiGuilio, Stan Harville, Matthew W. Forkner
  • Publication number: 20140058138
    Abstract: Methods and systems are provided for converting methane in a feed stream to butanediol. The method includes processing acetylene as an intermediate stream to form a hydrocarbon stream including butanediol. A hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream is treated to convert acetylene to another hydrocarbon process. The method according to certain aspects includes controlling the level of carbon monoxide to prevent undesired reactions in downstream processing units.
    Type: Application
    Filed: June 11, 2013
    Publication date: February 27, 2014
    Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
  • Publication number: 20130338405
    Abstract: An object of the invention is to provide a production method that can produce glycol from polyhydric alcohol with high selectivity and in a satisfactory yield. The object is achieved by using a silver catalyst in a reaction for synthesizing hydroxyketone from polyhydric alcohol having adjacent hydroxyl groups, and a hydrogenation catalyst in a reaction for synthesizing glycol from hydroxyketone.
    Type: Application
    Filed: January 12, 2012
    Publication date: December 19, 2013
    Inventors: Tetsuro Kizaki, Keizo Iwatani, Xin Chen, Satoshi Sato
  • Patent number: 8604254
    Abstract: Convert an alkylene to a product stream that comprises an alkanol by subjecting a gaseous combination of a) an alkylene selected from ethylene, propylene or a combination thereof, b) carbon monoxide, c) hydrogen and, optionally, d) at least one hydrocarbon or gas diluent other than ethylene or propylene to reductive hydroformylation conditions in combination with a solid phase, sulfided, heterogeneous catalyst.
    Type: Grant
    Filed: November 2, 2010
    Date of Patent: December 10, 2013
    Assignee: Dow Global Technologies LLC
    Inventors: Nancy Kinkade, Richard M. Wehmeyer
  • Patent number: 8563784
    Abstract: The invention relates to a catalytic method for the industrial production of a diol compound, such as 2-methyl-2-4-pentanediol, also called 2,4-hexylene glycol (HGL), from a ?-hydroxy carbonyl compound, Formula (I), in particular diacetone alcohol (DAA).
    Type: Grant
    Filed: December 15, 2009
    Date of Patent: October 22, 2013
    Assignee: Rhodia Poliamida e Especialidades Ltda
    Inventors: Danilo Zim, Philippe Marion
  • Publication number: 20130245330
    Abstract: The catalytic conversion of glycerol or acetol to alcohols, such as polyhydric alcohols like propylene glycol and simple alcohols like methanol and ethanol, without the addition of external hydrogen, is improved by the use of a transition metal alloy catalyst which, in the case of glycerol, is a nickel alloy catalyst.
    Type: Application
    Filed: March 11, 2013
    Publication date: September 19, 2013
    Applicant: University of Idaho
    Inventors: Bingjun Brian He, Randy Latayan Maglinao
  • Patent number: 8492597
    Abstract: The present invention describes a process for the production of propylene glycol from glycerol, the transformation of purified glycerol to propylene glycol being carried out by means of a reaction of hydrogenolysis, in the liquid phase, where the two stages of the reaction take place simultaneously and in one and the same reactor (1) under specified conditions of temperature and pressure, and the effluent from the fixed-bed reactor (1) is led to subsequent process stages that comprise separation and purification.
    Type: Grant
    Filed: February 24, 2011
    Date of Patent: July 23, 2013
    Assignee: Petroleo Brasileiro S.A.-Petrobras
    Inventors: Carlos René Klotz Rabello, Marlito Gomes Junior, Bernardo Galvão Siqueira, Raphael Bezerra de Menezes, Wilson Kenzo Huziwara, Tomas Shinobu Yamada, Lígia Maria Marçareli de Oliveira, Giselle de Carvalho Oliveira, William Victor Carlos Cândido
  • Publication number: 20130172578
    Abstract: Disclosed are processes for preparing 1,6-hexanediol and synthetic intermediates useful in the production of 1,6-hexanediol from renewable biosources. In one embodiment, a process comprises contacting levoglucosenone with hydrogen in the presence of a first hydrogenation catalyst at a first temperature to form product mixture (I); and heating product mixture (I) in the presence of hydrogen and a second hydrogenation catalyst at a second temperature to form product mixture (II) which comprises 1,6-hexanediol.
    Type: Application
    Filed: December 28, 2012
    Publication date: July 4, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: E I DU PONT DE NEMOURS AND COMPANY
  • Publication number: 20130172629
    Abstract: Disclosed are processes for preparing 1,6-hexanediol from levoglucosenone. In one embodiment, the process comprises contacting levoglucosenone with hydrogen in the presence of a hydrogenation catalyst comprising palladium, platinum/tungsten, nickel/tungsten, rhodium/rhenium, or mixtures thereof at a first temperature between about 50° C. and 100° C. and at a first reaction pressure between about 50 psi and 2000 psi for a first reaction period, and at a second temperature between about 120° C. and 250° C. and at a second pressure between about 500 psi and 2000 psi for a second reaction period to form a product mixture comprising 1,6-hexanediol, wherein the first reaction period is the amount of time in which the levoglucosenone has a conversion of at least about 95%.
    Type: Application
    Filed: December 28, 2012
    Publication date: July 4, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: E I DU PONT DE NEMOURS AND COMPANY
  • Publication number: 20130053534
    Abstract: A process for distilling an aqueous NPG mixture comprising NPG, a tertiary amine, water and the adduct of tertiary amine and formic acid (amine formate), said distillation being performed in a distillation column, which comprises drawing off a gaseous stream in the upper region of the column and feeding it to two condensers connected in series, the first condenser being operated in such a way that a portion of the gaseous stream is condensed in the first condenser and the second condenser being operated in such a way that the uncondensed portion of the gaseous stream is essentially fully condensed in the second condenser, the condensed stream from the first condenser being recycled fully or partly as reflux into the column.
    Type: Application
    Filed: August 17, 2012
    Publication date: February 28, 2013
    Applicant: BASF SE
    Inventors: Helmut Kronemayer, Kai Stehmeier, Ralf Edinger, Stefan Rittinger, Michael Steiniger
  • Publication number: 20120330070
    Abstract: This invention relates generally to a process for value-added processing of fats and oils to yield glycerol and glycerol derivatives. More particularly, the process converts glycerol to acetol and then acetol to propylene glycol to produce a propylene glycol with ultra-low amounts of ethylene glycol. The propylene glycol thus produced may be used as an antifreeze, deicing compound, or anti-icing compound.
    Type: Application
    Filed: August 27, 2012
    Publication date: December 27, 2012
    Inventor: Galen J. Suppes
  • Patent number: 8252961
    Abstract: This invention relates generally to a process for value-added processing of fats and oils to yield glycerol and glycerol derivatives. More particularly, the process converts glycerol to acetol and then acetol to propylene glycol to produce a propylene glycol with ultra-low amounts of ethylene glycol. The propylene glycol thus produced may be used as an antifreeze, deicing compound, or anti-icing compound.
    Type: Grant
    Filed: December 19, 2008
    Date of Patent: August 28, 2012
    Assignee: The Curators of The University of Missouri
    Inventor: Galen J. Suppes
  • Publication number: 20120022298
    Abstract: The invention relates to a process for preparing 1,6-hexanediol, preferably with at least 99.5% purity, which are especially virtually free of 1,4-cyclohexanediols, from a carboxylic acid mixture which is obtained as a by-product of the catalytic oxidation of cyclohexane to cyclohexanone/cyclohexanol with oxygen or oxygen-comprising gases and by water extraction of the reaction mixture, by hydrogenating the carboxylic acid mixture, esterifying and hydrogenating a substream to hexanediol.
    Type: Application
    Filed: March 29, 2010
    Publication date: January 26, 2012
    Applicant: BASF SE
    Inventors: Rolf Pinkos, Daniel Breuninger, Gerd-Dieter Tebben
  • Publication number: 20110313204
    Abstract: The invention relates to a catalytic method for the industrial production of a diol compound, such as 2-methyl-2-4-pentanediol, also called 2,4-hexylene glycol (HGL), from a ?-hydroxy carbonyl compound, Formula (I), in particular diacetone alcohol (DAA).
    Type: Application
    Filed: December 15, 2009
    Publication date: December 22, 2011
    Applicant: RHODIA POLIAMIDA E ESPECIALIDADES LTDA
    Inventors: Danilo Zim, Philippe Marion
  • Patent number: 8080692
    Abstract: The invention relates generally to the production of oxygenated hydrocarbons such as lower alcohols and more preferably 1,2-propanediol. More particularly, this invention comprises a single-step catalytic process for the catalytic production of lower alcohols such as methanol, ethanol, ethylene glycol and 1,2-propanediol from glycerol in aqueous medium. The catalyst comprises a metal selected from the Group VIII transition metals, preferably platinum, alloys thereof and mixtures thereof and a microporous carrier, preferably a faujasite-type zeolite.
    Type: Grant
    Filed: December 27, 2007
    Date of Patent: December 20, 2011
    Assignee: Katholieke Universiteit Leuven
    Inventors: Els D'Hondt, Pierre Jacobs, Bert Sels
  • Publication number: 20110295044
    Abstract: The present invention describes a process for the production of propylene glycol from glycerol, the transformation of purified glycerol to propylene glycol being carried out by means of a reaction of hydrogenolysis, in the liquid phase, where the two stages of the reaction take place simultaneously and in one and the same reactor (1) under specified conditions of temperature and pressure, and the effluent from the fixed-bed reactor (1) is led to subsequent process stages that comprise separation and purification.
    Type: Application
    Filed: February 24, 2011
    Publication date: December 1, 2011
    Applicant: PETROLEO BRASILEIRO S.A. - PETROBRAS
    Inventors: Carlos René Klotz Rabello, Marlito Gomes Junior, Bernardo Galvão Siqueira, Raphael Bezerra de Menezes, Wilson Kenzo Huziwara, Tomas Shinobu Yamada, Ligia Maria Marcareli de Oliveira, Giselle de Carvalho Oliveira, William Victor Carlos Candido
  • Publication number: 20110282106
    Abstract: The present invention relates to a process for preparing neopentyl glycol (NPG) by continuously hydrogenating hydroxypivalaldehyde (HPA) with hydrogen, in the liquid phase, in the presence of a hydrogenation catalyst, in a hydrogenation reactor (5), by combining an HPA-comprising stream (1) with an NPG-comprising stream (2) to give a hydrogenation feed (4) and introducing the hydrogenation feed (4) into the hydrogenation reactor (5) and additionally supplying at least one pH regulator (3) selected from the group consisting of tertiary amine, an inorganic base, an inorganic acid and an organic acid to the HPA-comprising stream (1) or the NPG-comprising stream (2) or the hydrogenation feed (4), in order to establish a pH of 7.0 to 9.
    Type: Application
    Filed: May 11, 2011
    Publication date: November 17, 2011
    Applicant: BASF SE
    Inventors: Michael Steiniger, Maria Guixa Guardia, Kai Stehmeier
  • Patent number: 8017816
    Abstract: A reactive-separation process converts glycerin into lower alcohols, having boiling points less than 200° C., at high yields. Conversion of natural glycerin to propylene glycol through an acetol intermediate is achieved at temperatures from 150° to 250° C. at pressures from 1 and 25 bar. The preferred applications of the propylene glycol are as an antifreeze, deicing compound, or anti-icing compound. The preferred catalyst for this process in a copper-chromium.
    Type: Grant
    Filed: August 28, 2006
    Date of Patent: September 13, 2011
    Assignees: The Curators Of the University Of Missouri, Renewable Alternatives LLC
    Inventors: Galen J. Suppes, William Rusty Sutterlin
  • Patent number: 8013192
    Abstract: The invention provides a process for preparing 1,3-alkanediols, such as 1,3-propanediol (PDO), from 3-hydroxyaldehydes, such as 3-hydroxypropanal (HPA), comprising providing a mixture of 3-hydroxyaldehydes in an organic solvent; extracting into an aqueous liquid a major portion of the 3-hydroxyaldehydes to provide an aqueous phase comprising 3-hydroxyaldehydes in greater concentration than the concentration of 3-hydroxyaldehydes in the 3-hydroxyaldehyde mixture, and an organic phase; separating the aqueous phase from the organic phase; contacting the aqueous phase with hydrogen in the presence of a hydrogenation catalyst to provide a hydrogenation product mixture comprising 1,3-alkanediols and water; separating water from the 1,3-alkanediols using a multi-effect evaporation scheme; recycling water containing about 50 wt % or less 1,3-propanediol based upon the total amount of 1,3-propanediol and water to the extraction stage; and recovering 1,3-alkanediols.
    Type: Grant
    Filed: December 4, 2007
    Date of Patent: September 6, 2011
    Assignee: Shell Oil Company
    Inventors: Douglas Lee Husen, Glenn Charles Komplin, Joseph Broun Powell, Paul Richard Weider
  • Publication number: 20110098503
    Abstract: A process for upgrading an organic acid includes neutralizing the organic acid to form a salt and thermally decomposing the resulting salt to form an energy densified product. In certain embodiments, the organic acid is levulinic acid. The process may further include upgrading the energy densified product by conversion to alcohol and subsequent dehydration.
    Type: Application
    Filed: October 26, 2010
    Publication date: April 28, 2011
    Inventors: M. Clayton Wheeler, G. Peter van Walsum, Thomas J. Schwartz, Adriaan Reinhard Pieter van Heiningen
  • Publication number: 20110040132
    Abstract: A reactive-separation process converts glycerin into lower alcohols, having boiling points less than 200° C., at high yields. Conversion of natural glycerin to propylene glycol through an acetol intermediate is achieved at temperatures from 150° to 250° C. at a pressure ranging from 1 and 25 bar. The preferred applications of the propylene glycol are as an antifreeze, deicing compound, or anti-icing compound. The preferred catalyst for this process in a copper-chromium powder.
    Type: Application
    Filed: October 18, 2010
    Publication date: February 17, 2011
    Inventors: Galen J. Suppes, William Rusty Sutterlin, Mohanprasad Dasari
  • Publication number: 20110004030
    Abstract: A process for the removal of hydroxypropane from a crude product stream from the hydrogenation of glycerol, the crude product stream comprising 1,2-propanediol and hydroxypropanone as impurity, the process comprising: (a) where required condensing the crude product stream; and (b) contacting the crude product phase in the liquid phase with a stream of a hydrogen-containing gas in the presence of a heterogeneous catalyst at suitable temperatures and pressures such that hydroxypropanone present in the crude product stream is converted to the desired propanediol.
    Type: Application
    Filed: December 2, 2008
    Publication date: January 6, 2011
    Applicant: DAVY PROCESS TECHNOLOGY LIMITED
    Inventors: Michael William Marshall Tuck, Robert Wild, Simon Nicholas Tilley
  • Patent number: 7759530
    Abstract: The invention relates to a method for hydrogenation of an organic compound comprising at least one carbonyl group, whereby the organic compound is brought into contact with a moulded body in the presence of hydrogen. Said body may be produced by a method in which (i) an oxidic material is prepared, comprising copper oxide, aluminum oxide, and at least one oxide of lanthanum, tungsten, molybdenum, titanium, or zirconium, followed by (ii) addition of powdered metallic copper, copper platelets, powdered cement, graphite, mixtures or a mixture thereof with graphite to the oxidic material and (iii) moulding the mixture from (ii) to give a moulded body, characterised in that the moulded body is in the form of catalyst tablets or catalyst extrudates with a diameter d and/or height h<2.5 mm, catalyst beads with a diameter d<2.5 mm or catalyst honeycomb with a cell diameter rz<2.5 mm.
    Type: Grant
    Filed: July 7, 2005
    Date of Patent: July 20, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Christophe Houssin, Henrik Junicke, Andrea Haunert
  • 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: 7696386
    Abstract: The invention is a process of using, as a reducing agent, a 12CaO.7Al2O3 electride containing electrons in a number of 1019 or more and 2.3×1021 cm?3 or less in its cages to subject a carbonyl compound to reductive coupling in a solvent, thereby synthesizing a diol or polydiol. The invention is also a process of reducing a ketone compound in a solvent, thereby synthesizing a secondary alcohol or diketone compound. According to the process of the invention, it is possible to synthesize a diol or polydiol, or a secondary alcohol or diketone compound through simple operations in a short period without using an expensive and harmful metal hydride or metal salt nor limiting the atmosphere for the synthesis to an inert gas atmosphere as in conventional processes.
    Type: Grant
    Filed: September 28, 2007
    Date of Patent: April 13, 2010
    Assignee: Japan Science and Technology Agency
    Inventors: Hideo Hosono, Haritha Buchammagari, Yoshitake Toda, Masahiro Hirano, Kohtaro Osakada, Daisuke Takeuchi
  • Patent number: 7663004
    Abstract: A reactive-separation process converts glycerin into lower alcohols, having boiling points less than 200° C., at high yields. Conversion of natural glycerin to propylene glycol through an acetol intermediate is achieved at temperatures from 150° to 250° C. at a pressure ranging from 1 and 25 bar. The preferred applications of the propylene glycol are as an antifreeze, deicing compound, or anti-icing compound. The preferred catalyst for this process in a copper-chromium powder.
    Type: Grant
    Filed: March 24, 2005
    Date of Patent: February 16, 2010
    Assignees: The Curators of the University of Missouri, Renewable Alternatives LLC
    Inventors: Galen J. Suppes, William Rusty Sutterlin, Mohanprasad Dasari
  • Publication number: 20100016643
    Abstract: The present invention provides an integrated process for continuously preparing 1,4-butanediol, which comprises the following stages: (I) reacting formaldehyde with acetylene in the presence of a copper catalyst at a pH of from 5 to 8 and a molar ratio of formaldehyde to acetylene of at most 2:1, (II) intermediately buffering the resulting butynediol-containing aqueous mixture for from 0.1 to 100 h, (III) hydrogenating the mixture obtained after the intermediate buffering and (IV) distilling the hydrogenation product obtained in stage III to obtain 1,4-butanediol.
    Type: Application
    Filed: March 14, 2007
    Publication date: January 21, 2010
    Applicant: BASF SE
    Inventors: Rolf Pinkos, Rudolf Erich Lorenz, York Alexander Beste
  • Patent number: 7619124
    Abstract: A process for the preparation of propylene glycol from glycerol by a high pressure and temperature hydrogenation reaction is described. In a particular embodiment, a base is present in the solvent mixture with an alkanol or ether of the alkanol. The reaction progresses over a transition metal catalyst. Propylene glycol is used for antifreeze and deicing compositions.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: November 17, 2009
    Assignee: Board of Trustees of Michigan State University
    Inventors: Dennis J. Miller, James E. Jackson, Simona Marincean
  • Patent number: 7615671
    Abstract: Disclosed is a process for the preparation of 1,2-glycols by hydrogenation of 1,2-dioxygenated organic compounds in the presence of a catalyst composition comprising a ruthenium compound, a trivalent phosphorus compound selected from 1,1,1-tris(diarylphosphinomethyl)alkyl or substituted alkyl, and a promoter selected from Lewis acids, protic acids having an ionization constant (Ki) of 5×10?3 or greater, and onium salts. The process is useful for the hydrogenation of glycolic acid or derivatives thereof to ethylene glycol.
    Type: Grant
    Filed: November 20, 2008
    Date of Patent: November 10, 2009
    Assignee: Eastman Chemical Company
    Inventors: Thomas Allen Puckette, Kenneth Wayne Hampton, Jr.
  • Patent number: 7612241
    Abstract: A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted 4,5-bis(di-n-alkylphosphino)xanthene. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.
    Type: Grant
    Filed: March 23, 2009
    Date of Patent: November 3, 2009
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Wilfred P. Shum, David John Cole-Hamilton