Of Aldehyde Or Ketone Patents (Class 568/862)
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Patent number: 11458448Abstract: A magnetic strong base anion exchange resin with high mechanical strength and a preparation method thereof, belonging to the field of resin materials. The preparation method comprises steps of: adding a conventional strong base anion exchange resin to a mixture of trivalent iron salt and divalent iron salt, and then mixing the resin adsorbed with the iron salt with aqueous ammonia so that Fe3O4 nanoparticles are contained in the resin structure. Then, the resin containing Fe3O4 nanoparticles is added to alcoholic solution dissolved with silane coupling agent to form a dense SiO2 coating on the surface of the resin, so as to obtain magnetic strong base anion exchange resin with high mechanical strength.Type: GrantFiled: April 20, 2018Date of Patent: October 4, 2022Assignees: NANJING UNIVERSITY, NANJING UNIVERSITY & YANCHENG ACADEMY OF ENVIRONMENTAL PROTECTION TECHNOLOGY AND ENGINEERINGInventors: Chendong Shuang, Guang Zhang, Aimin Li, Ting Ye, Zheng Wang
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Patent number: 11384038Abstract: 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 the gas phase in the presence of a copper on carbon catalyst.Type: GrantFiled: January 5, 2017Date of Patent: July 12, 2022Assignee: HALDOR TOPSØE A/SInventors: Christian Mårup Osmundsen, Esben Taarning, Morten Boberg Larsen
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Patent number: 10759726Abstract: 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: GrantFiled: January 5, 2017Date of Patent: September 1, 2020Assignee: HALDOR TOPSØE A/SInventors: Martin Spangsberg Holm, Christian Mårup Osmundsen, Esben Taarning, Amanda Birgitte Sølvhøj, Morten Boberg Larsen
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Patent number: 10752568Abstract: 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: GrantFiled: June 17, 2019Date of Patent: August 25, 2020Assignee: Zhangjiagang Glory Chemical Industry Co., Ltd.Inventors: Changlin Chen, Xiaodong Zhu, Bing Han, Chengchao Xiao
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Patent number: 10144687Abstract: 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: GrantFiled: January 6, 2014Date of Patent: December 4, 2018Assignee: Mitsubishi Chemical CorporationInventors: Yusuke Izawa, Masaru Utsunomiya, Kouta Tanaka, Norikazu Konishi
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Patent number: 9914684Abstract: 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: GrantFiled: November 16, 2016Date of Patent: March 13, 2018Assignee: Lyondell Chemical Technology, L.P.Inventors: Sarthak Gaur, Beaven S. Mandimutsira, Daniel F. White, Walter S. Dubner
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Patent number: 9783472Abstract: 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: GrantFiled: June 22, 2016Date of Patent: October 10, 2017Assignee: Iowa Corn Promotion BoardInventors: David James Schreck, Ray Chrisman, Brooke Albin, Nye Atwood Clinton, Marion McKinley Bradford
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Patent number: 9353032Abstract: 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: GrantFiled: September 28, 2013Date of Patent: May 31, 2016Assignee: OXEA GMBHInventors: Matthias Eisenacher, Kurt Schalapski, Heinz Strutz
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Patent number: 9126912Abstract: 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: GrantFiled: August 20, 2014Date of Patent: September 8, 2015Inventors: Chien-An Chen, Yi-Wen Chen
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Patent number: 9056824Abstract: 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: GrantFiled: January 31, 2013Date of Patent: June 16, 2015Assignee: Eastman Chemical CompanyInventors: Kenneth Wayne Hampton, Jr., Eugene H. Brown
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Patent number: 8969632Abstract: 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: GrantFiled: March 23, 2012Date of Patent: March 3, 2015Assignee: Eastman Chemical CompanyInventors: David William Norman, Jonathan Michael Penney, Peter Borden Mackenzie
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Patent number: 8962894Abstract: 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: GrantFiled: December 28, 2012Date of Patent: February 24, 2015Assignee: E I du Pont de Nemours and CompanyInventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta, Christina S Stauffer
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Patent number: 8937202Abstract: 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: GrantFiled: February 23, 2010Date of Patent: January 20, 2015Assignee: Battelle Memorial InstituteInventors: John G. Frye, Aaron A. Oberg, Alan H. Zacher
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Patent number: 8933277Abstract: 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: GrantFiled: January 7, 2010Date of Patent: January 13, 2015Assignee: BASF SEInventors: Stephan Schlitter, Michael Steiniger, Stefan Rittinger, Tilman Sirch, Steffen Maas
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Patent number: 8921617Abstract: 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: GrantFiled: May 9, 2012Date of Patent: December 30, 2014Assignee: Symrise AGInventors: Oskar Koch, Angela Köckritz, Michael Kant, Andreas Martin, Axel Schöning, Udo Armbruster, Michael Bartoszek, Sigrid Evert, Brigitte Lange, Regina Bienert
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Patent number: 8921616Abstract: 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: GrantFiled: January 12, 2012Date of Patent: December 30, 2014Assignees: Clariant Catalysts (Japan) K.K., National University Corporation Chiba UniversityInventors: Tetsuro Kizaki, Keizo Iwatani, Xin Chen, Satoshi Sato
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Patent number: 8889922Abstract: 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: GrantFiled: December 28, 2012Date of Patent: November 18, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Alan Martin Allgeier, David Richard Corbin, Wathudura Indika Namal De Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta
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Patent number: 8853465Abstract: 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: GrantFiled: May 11, 2011Date of Patent: October 7, 2014Assignee: BASF SEInventors: Michael Steiniger, Maria Guixa Guardia, Kai Stehmeier
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Patent number: 8853458Abstract: 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: GrantFiled: January 11, 2013Date of Patent: October 7, 2014Assignee: Rennovia, Inc.Inventors: Eric L. Dias, James A. W. Shoemaker, Thomas R. Boussie, Vincent J. Murphy
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Publication number: 20140275371Abstract: 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: ApplicationFiled: March 11, 2014Publication date: September 18, 2014Applicant: Bayer Intellectual Property GmbHInventors: Thomas Ernst Müller, Christoph Gürtler, Walter Leitner, Henning Vogt, Saeeda Soomro
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Publication number: 20140213827Abstract: 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: ApplicationFiled: January 31, 2013Publication date: July 31, 2014Applicant: Eastman Chemical CompanyInventors: Kenneth Wayne Hampton, JR., Eugene H. Brown
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Patent number: 8710278Abstract: 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: GrantFiled: January 31, 2013Date of Patent: April 29, 2014Assignee: Eastman Chemical CompanyInventors: Kenneth Wayne Hampton, Jr., Eugene H. Brown, Thomas K. Brown, Amy K. Paris, Kevin S. Howe, Thomas Allen Puckette
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Patent number: 8664448Abstract: 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: GrantFiled: June 2, 2009Date of Patent: March 4, 2014Assignee: Huntsman Petrochemical LLCInventors: Srinivasa Godavarthy, Wei-Yang Su, Ralph M. DiGuilio, Stan Harville, Matthew W. Forkner
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Publication number: 20140058138Abstract: 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: ApplicationFiled: June 11, 2013Publication date: February 27, 2014Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
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Publication number: 20130338405Abstract: 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: ApplicationFiled: January 12, 2012Publication date: December 19, 2013Inventors: Tetsuro Kizaki, Keizo Iwatani, Xin Chen, Satoshi Sato
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Patent number: 8604254Abstract: 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: GrantFiled: November 2, 2010Date of Patent: December 10, 2013Assignee: Dow Global Technologies LLCInventors: Nancy Kinkade, Richard M. Wehmeyer
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Patent number: 8563784Abstract: 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: GrantFiled: December 15, 2009Date of Patent: October 22, 2013Assignee: Rhodia Poliamida e Especialidades LtdaInventors: Danilo Zim, Philippe Marion
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Publication number: 20130245330Abstract: 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: ApplicationFiled: March 11, 2013Publication date: September 19, 2013Applicant: University of IdahoInventors: Bingjun Brian He, Randy Latayan Maglinao
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Patent number: 8492597Abstract: 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: GrantFiled: February 24, 2011Date of Patent: July 23, 2013Assignee: Petroleo Brasileiro S.A.-PetrobrasInventors: 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
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Publication number: 20130172629Abstract: 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: ApplicationFiled: December 28, 2012Publication date: July 4, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Publication number: 20130172578Abstract: 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: ApplicationFiled: December 28, 2012Publication date: July 4, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Publication number: 20130053534Abstract: 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: ApplicationFiled: August 17, 2012Publication date: February 28, 2013Applicant: BASF SEInventors: Helmut Kronemayer, Kai Stehmeier, Ralf Edinger, Stefan Rittinger, Michael Steiniger
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Publication number: 20120330070Abstract: 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: ApplicationFiled: August 27, 2012Publication date: December 27, 2012Inventor: Galen J. Suppes
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Patent number: 8252961Abstract: 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: GrantFiled: December 19, 2008Date of Patent: August 28, 2012Assignee: The Curators of The University of MissouriInventor: Galen J. Suppes
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Publication number: 20120022298Abstract: 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: ApplicationFiled: March 29, 2010Publication date: January 26, 2012Applicant: BASF SEInventors: Rolf Pinkos, Daniel Breuninger, Gerd-Dieter Tebben
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Publication number: 20110313204Abstract: 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: ApplicationFiled: December 15, 2009Publication date: December 22, 2011Applicant: RHODIA POLIAMIDA E ESPECIALIDADES LTDAInventors: Danilo Zim, Philippe Marion
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Patent number: 8080692Abstract: 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: GrantFiled: December 27, 2007Date of Patent: December 20, 2011Assignee: Katholieke Universiteit LeuvenInventors: Els D'Hondt, Pierre Jacobs, Bert Sels
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Publication number: 20110295044Abstract: 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: ApplicationFiled: February 24, 2011Publication date: December 1, 2011Applicant: PETROLEO BRASILEIRO S.A. - PETROBRASInventors: 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
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Publication number: 20110282106Abstract: 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: ApplicationFiled: May 11, 2011Publication date: November 17, 2011Applicant: BASF SEInventors: Michael Steiniger, Maria Guixa Guardia, Kai Stehmeier
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Patent number: 8017816Abstract: 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: GrantFiled: August 28, 2006Date of Patent: September 13, 2011Assignees: The Curators Of the University Of Missouri, Renewable Alternatives LLCInventors: Galen J. Suppes, William Rusty Sutterlin
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Patent number: 8013192Abstract: 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: GrantFiled: December 4, 2007Date of Patent: September 6, 2011Assignee: Shell Oil CompanyInventors: Douglas Lee Husen, Glenn Charles Komplin, Joseph Broun Powell, Paul Richard Weider
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Publication number: 20110098503Abstract: 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: ApplicationFiled: October 26, 2010Publication date: April 28, 2011Inventors: M. Clayton Wheeler, G. Peter van Walsum, Thomas J. Schwartz, Adriaan Reinhard Pieter van Heiningen
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Publication number: 20110040132Abstract: 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: ApplicationFiled: October 18, 2010Publication date: February 17, 2011Inventors: Galen J. Suppes, William Rusty Sutterlin, Mohanprasad Dasari
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Publication number: 20110004030Abstract: 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: ApplicationFiled: December 2, 2008Publication date: January 6, 2011Applicant: DAVY PROCESS TECHNOLOGY LIMITEDInventors: Michael William Marshall Tuck, Robert Wild, Simon Nicholas Tilley
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Patent number: 7759530Abstract: 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: GrantFiled: July 7, 2005Date of Patent: July 20, 2010Assignee: BASF AktiengesellschaftInventors: Christophe Houssin, Henrik Junicke, Andrea Haunert
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Patent number: 7732644Abstract: 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: GrantFiled: November 8, 2006Date of Patent: June 8, 2010Assignee: Kao CorporationInventors: Kosaku Ishida, Shigeyoshi Tanaka, Takahiro Asada
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Patent number: 7696386Abstract: 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: GrantFiled: September 28, 2007Date of Patent: April 13, 2010Assignee: Japan Science and Technology AgencyInventors: Hideo Hosono, Haritha Buchammagari, Yoshitake Toda, Masahiro Hirano, Kohtaro Osakada, Daisuke Takeuchi
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Patent number: 7663004Abstract: 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: GrantFiled: March 24, 2005Date of Patent: February 16, 2010Assignees: The Curators of the University of Missouri, Renewable Alternatives LLCInventors: Galen J. Suppes, William Rusty Sutterlin, Mohanprasad Dasari
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Publication number: 20100016643Abstract: 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: ApplicationFiled: March 14, 2007Publication date: January 21, 2010Applicant: BASF SEInventors: Rolf Pinkos, Rudolf Erich Lorenz, York Alexander Beste
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Patent number: 7619124Abstract: 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: GrantFiled: March 28, 2008Date of Patent: November 17, 2009Assignee: Board of Trustees of Michigan State UniversityInventors: Dennis J. Miller, James E. Jackson, Simona Marincean