Purification Or Recovery Patents (Class 568/854)
  • Patent number: 10696785
    Abstract: A diol composition includes a diol as a major component and has an electrical conductivity of 0.6 to 30 mS/m.
    Type: Grant
    Filed: February 21, 2012
    Date of Patent: June 30, 2020
    Assignee: Toray Industries, Inc.
    Inventors: Masateru Ito, Izumi Morita, Kenji Kawamura, Tetsuya Yamada, Sadanori Kumazawa, Katsushige Yamada
  • Patent number: 8987523
    Abstract: The present invention relates to a process for obtaining ditrimethylolpropane and trimethylolpropane-enriched product streams from the high-boiling fractions and residues which are obtained in the distillative purification of trimethylolpropane, wherein an aqueous solution of these fractions and residues is catalytically hydrogenated in the presence of an acidic compound and, after removing solids, contacted both with basic and with acidic ion exchangers. A trimethylolpropane-enriched product stream can be distilled out of the aqueous eluate obtained, leaving ditrimethylolpropane as the distillation residue.
    Type: Grant
    Filed: July 28, 2011
    Date of Patent: March 24, 2015
    Assignee: Oxea GmbH
    Inventors: Thorsten Kreickmann, Guido D. Frey, Norman Nowotny, Heinz Strutz
  • Patent number: 8987527
    Abstract: A process for obtaining trimethylolpropane-enriched product streams from the forerun fractions obtained in the distillative purification of trimethylolpropane is characterized in that: (a) the forerun fractions are treated separately or in combination at a temperature of 160 to 280° C. and at a pressure of 1 to 30 MPa with hydrogen in the presence of a hydrogenation catalyst and an acidic compound; and (b) the reaction mixture obtained after step a) is separated by distillation into a trimethylolpropane-enriched, catalyst-free product stream and a catalyst-containing product stream. The trimethylolpropane is prepared by the Cannizzaro process using alkali metal or alkaline earth metal compounds or stoichiometric amounts of trialkylamines, or is produced by the hydrogenation process in the presence of catalytic amounts of trialkylamines or alkali metal or alkaline earth metal compounds.
    Type: Grant
    Filed: November 28, 2012
    Date of Patent: March 24, 2015
    Assignee: Oxea GmbH
    Inventors: Guido D. Frey, Heinz Strutz
  • 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: 8907139
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid. Separation and purification processes of the crude ethanol products are employed to allow recovery of ethanol and hydrolyze acetal impurities by the addition of an acid stream.
    Type: Grant
    Filed: December 19, 2012
    Date of Patent: December 9, 2014
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, David Lee, Adam Orosco, R. Jay Warner, Heiko Weiner, Zhenhua Zhou, Emily Duff, Radmila Jevtic
  • Patent number: 8884076
    Abstract: The present invention relates to a process for distilling an aqueous polymethylol mixture which comprises a polymethylol of the formula (I) (HOCH2)2—C—R2??(I) in which each R is independently a further methylol group or an alkyl group having 1 to 22 carbon atoms or an aryl or aralkyl group having 6 to 22 carbon atoms, a tertiary amine, water and the adduct of tertiary amine and formic acid (amine formate), which comprises performing the distillation in a distillation column which is connected at the bottom to an evaporator, the bottom temperature being above the evaporation temperature of the monoester of formic acid and polymethylol (polymethylol formate) which forms during distillation. The present invention further relates to a composition comprising polymethylol and 1 to 10 000 ppm by weight of polymethylol formate, and to the use thereof.
    Type: Grant
    Filed: December 7, 2009
    Date of Patent: November 11, 2014
    Assignee: BASF SE
    Inventors: Tilman Sirch, Michael Steiniger, Steffen Maas, Stefan Rittinger, Stephan Schlitter
  • Publication number: 20140296583
    Abstract: A process for obtaining trimethylolpropane-enriched product streams from the forerun fractions obtained in the distillative purification of trimethylolpropane is characterized in that: (a) the forerun fractions are treated separately or in combination at a temperature of 160 to 280° C. and at a pressure of 1 to 30 MPa with hydrogen in the presence of a hydrogenation catalyst and an acidic compound; and (b) the reaction mixture obtained after step a) is separated by distillation into a trimethylolpropane-enriched, catalyst-free product stream and a catalyst-containing product stream. The trimethylolpropane is prepared by the Cannizzaro process using alkali metal or alkaline earth metal compounds or stoichiometric amounts of trialkylamines, or is produced by the hydrogenation process in the presence of catalytic amounts of trialkylamines or alkali metal or alkaline earth metal compounds.
    Type: Application
    Filed: November 28, 2012
    Publication date: October 2, 2014
    Inventors: Guido D. Frey, Heinz Strutz
  • Publication number: 20140288318
    Abstract: Process for obtaining ditrimethylolpropane and trimethylolpropane-enriched product streams from the high-boiling fractions and residues which are obtained in the distillative purification of trimethylolpropane includes three stage distillation characterized in that second and third stages are configured as thin film evaporators with a column attachment with the second stage facilitating trimethylopropane recovery and the third stage facilitating ditrimethylolpropane recovery.
    Type: Application
    Filed: October 24, 2012
    Publication date: September 25, 2014
    Applicant: Oxea GmbH
    Inventors: Guido D. Frey, Kurt Schalapski, Dirk Bermann, Norman Nowotney, Heinz Strutz, Donald K. Raff
  • Patent number: 8759593
    Abstract: A method of reclaiming alcohols from purification residue includes hydrolyzing a purification residue with an aqueous medium in the presence of (i) an acid and (ii) an oxidizing agent.
    Type: Grant
    Filed: September 17, 2012
    Date of Patent: June 24, 2014
    Assignee: Oxea Bishop LLC
    Inventors: Kenneth A. Windhorst, Oakley T. Cortez, Donald K. Raff
  • 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: 8686197
    Abstract: The present invention relates to a method for producing trimethylolpropane having a low color number by processing a raw reaction solution obtained according to the inorganic Cannizarro process while adhering to precisely defined pH values.
    Type: Grant
    Filed: August 6, 2010
    Date of Patent: April 1, 2014
    Assignee: LANXESS Deutschland GmbH
    Inventors: Ulrich Notheis, Hans-Dieter Gerriets, Michael Friederich
  • Publication number: 20140081052
    Abstract: A method of reclaiming trimethylolpropane from purification residue includes hydrolyzing a purification residue with an aqueous medium in the presence of (i) an acid and (ii) an oxidizing agent.
    Type: Application
    Filed: September 17, 2012
    Publication date: March 20, 2014
    Inventors: Kenneth A. Windhorst, Oakley T. Cortez, Donald K. Raff
  • Publication number: 20140081053
    Abstract: A method of reclaiming alcohols from purification residue includes hydrolyzing a purification residue with an aqueous medium in the presence of (i) an acid and (ii) an oxidizing agent.
    Type: Application
    Filed: September 17, 2012
    Publication date: March 20, 2014
    Inventors: Kenneth A. Windhorst, Oakley T. Cortez, Donald K. Raff
  • Patent number: 8575401
    Abstract: The present invention relates to a process for purifying crude polymethylol which comprises polymethylol of the formula (I) (HOCH2)2—C—R2??(I) in which each R is independently a further methylol group or an alkyl group having 1 to 22 carbon atoms or an aryl or aralkyl group having 6 to 22 carbon atoms, and also hydroxy acid of the formula (IV) in which each R is independently as defined above, which comprises performing the purification in a distillation column, the bottom of the distillation column being connected to an evaporator with a short residence time. The present invention further relates to a composition comprising polymethylol and 1 to 10 000 ppm by weight of an ester of polymethylol and of a hydroxy acid and to the use thereof.
    Type: Grant
    Filed: December 7, 2009
    Date of Patent: November 5, 2013
    Assignee: BASF SE
    Inventors: Tilman Sirch, Michael Steiniger, Steffen Maas, Stefan Rittinger
  • Patent number: 8507734
    Abstract: The present invention provides a process for purifying a monoterpene or sesquiterpene having a purity greater than about 98.5% (w/w). The process comprises the steps of derivatizing the monoterpene (or sesquiterpene) to produce a monoterpene (or sesquiterpene) derivative, separating the monoterpene (or sesquiterpene) derivative, and releasing the monoterpene (or sesquiterpene) from the derivative. Also encompassed by the scope of the present invention is a pharmaceutical composition comprising a monoterpene (or sesquiterpene) having a purity greater than about 98.5% (w/w). The purified monoterpene can be used to treat a disease such as cancer. The present monoterpene (or sesquiterpene) may be administered alone, or may be co-administered with radiation or other therapeutic agents, such as chemotherapeutic agents.
    Type: Grant
    Filed: March 3, 2011
    Date of Patent: August 13, 2013
    Assignee: Neonc Technologies Inc.
    Inventors: Thomas Chen, Daniel Levin, Satish Puppali
  • Patent number: 8470566
    Abstract: A non-naturally occurring microbial organism having an isopropanol, 4-hydroxybutryate, or 1,4-butanediol pathway includes at least one exogenous nucleic acid encoding an isopropanol, 4-hydroxybutryate, or 1,4-butanediol pathway enzyme expressed in a sufficient amount to produce isopropanol, 4-hydroxybutryate, or 1,4-butanediol. The aforementioned organisms are cultured to produce isopropanol, 4-hydroxybutryate, or 1,4-butanediol.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: June 25, 2013
    Assignee: Genomatica, Inc.
    Inventors: John D. Trawick, Mark J. Burk, Anthony P. Burgard
  • Publication number: 20130131391
    Abstract: The present invention relates to a process for obtaining ditrimethylolpropane and trimethylolpropane-enriched product streams from the high-boiling fractions and residues which are obtained in the distillative purification of trimethylolpropane, wherein an aqueous solution of these fractions and residues is catalytically hydrogenated in the presence of an acidic compound and, after removing solids, contacted both with basic and with acidic ion exchangers. A trimethylolpropane-enriched product stream can be distilled out of the aqueous eluate obtained, leaving ditrimethylolpropane as the distillation residue.
    Type: Application
    Filed: July 28, 2011
    Publication date: May 23, 2013
    Applicant: OXEA GMBH
    Inventors: Thorsten Kreickmann, Guido D. Frey, Norman Nowotny, Heinz Strutz
  • Patent number: 8394998
    Abstract: The present invention relates to a method of producing neopentyl glycol by addition of isobutyraldehyde and formaldehyde in the presence of a tertiary alkylamine as catalyst to give the hydroxypivalinaldehyde with subsequent liquid phase hydrogenation in the presence of a nickel catalyst at a temperature of 80 to 180° C. and at a pressure of 6 to 18 MPa in the presence of an aliphatic alcohol and in the presence of water.
    Type: Grant
    Filed: June 12, 2009
    Date of Patent: March 12, 2013
    Assignee: Oxea GmbH
    Inventors: Kurt Schalapski, Tonia Kretz, Thorsten Kreickmann, Peter Heymanns, Rainer Lukas, Rolf-Peter Schulz
  • Patent number: 8389778
    Abstract: Methods for preparing mannitol modification III are described herein. The methods relate to preparing solutions of mannitol in a suitable solvent and an auxiliary agent and solidifying from the solutions mannitol of modification III.
    Type: Grant
    Filed: May 21, 2008
    Date of Patent: March 5, 2013
    Assignee: Aptuit (West Lafayette), LLC
    Inventors: Jan-Olav Henck, Mark C. Andres, Linda J. McCausland
  • Patent number: 8354561
    Abstract: The present invention provides a process for improving the color of trimethylolpropane which comprises the steps of a) supplying a crude, aqueous base solution of trimethylolpropane, containing color causing impurities, and having a pH of less than about 9; b) contacting said base solution with an alkaline material for a period of time sufficient to increase the pH of said base solution to greater than 11 and at a sufficient temperature to allow the color causing impurities to react with said alkaline material; c) cooling the resulting solution from step (b) for a sufficient period of time; d) contacting said base solution of step (c) with an organic acid for a sufficient period of time to lower the pH thereof to less than about 9.
    Type: Grant
    Filed: December 22, 2010
    Date of Patent: January 15, 2013
    Assignee: Oxea Bishop LLC
    Inventors: Kenneth A. Windhorst, David P. Harris, Marcos L. Schroeder, Fred Gaytan
  • Publication number: 20120271029
    Abstract: The present invention relates to a process for preparing hydroxypivalaldehyde (HPA), which comprises in a first stage reacting isobutyraldehyde with formaldehyde in the presence of a tertiary amine and in a second stage introducing the reaction output obtained from the first stage into a stripping column. The present application further relates to a process for preparing neopentyl glycol (NPG) by hydrogenating the hydroxypivalaldehyde prepared in accordance with the invention and the further conversion of the NPG thus obtained to polyester resins, unsaturated polyester resins, lubricants or plasticizers.
    Type: Application
    Filed: April 13, 2012
    Publication date: October 25, 2012
    Applicant: BASF SE
    Inventors: Helmut Kronemayer, Michael Steiniger, Eva Kretzschmar, Norbert Asprion, Marcus Bechtel
  • Patent number: 8293950
    Abstract: A method of preparing monopentaerythritol, dipentaerthritol, and sodium formate through high temperature condensation and cascade recrystallization is disclosed. The method lowers the energy consumption dramatically and improves the cost-effectiveness by carrying out the reaction in a non-low-temperature zone, and thereby avoiding the requirement for refrigeration. The method alleviates the difficulty of separation and improves the product quality by means of cascade separation process, and thereby avoiding the low purity from a single separation. In addition, the mother liquor obtained after each separation step is recycled to the previous step as the recycling liquor, which avoids discharging waste, increases the product yield and lowers raw materials consumption.
    Type: Grant
    Filed: March 31, 2006
    Date of Patent: October 23, 2012
    Assignee: Hubei Yihua Chemical Industry Co., Ltd.
    Inventors: Yuanhua Jiang, Xiaoqin Yang, Pingguan Bian, Jiaxin Feng, Jinjun Dong, Huazhong He, Yuanhai Li, Yexiang Zhang, Leguan Huang
  • Patent number: 8143458
    Abstract: Processes for separating butanediols from glycols are disclosed, as well as products and compositions resulting therefrom.
    Type: Grant
    Filed: October 29, 2007
    Date of Patent: March 27, 2012
    Assignee: Archer Daniels Midland Company
    Inventor: Peter Kalagias
  • Publication number: 20120010435
    Abstract: The present invention relates to a method for isolating ditrimethylol propane from secondary trimethylol propane production streams.
    Type: Application
    Filed: August 11, 2009
    Publication date: January 12, 2012
    Applicant: LANXESS DEUTSCHLAND GMBH
    Inventors: Gunter Rauchschwalbe, Ulrich Notheis, Michael Friederich, Hans-Dieer Gerriets, Carsten Hummelt, Christiane Oppenheimer-Stix, Paul Wagner
  • Publication number: 20110258915
    Abstract: Methods and apparatus for growing and sequentially processing algae to produce a variety of products including but not limited to biofuels, algal meal, oil, unsaturated fatty acids and recombinant proteins and peptides in a cost-effective and energy efficient manner. Also provided are methods of use for the products.
    Type: Application
    Filed: October 19, 2009
    Publication date: October 27, 2011
    Applicant: STC.UNM
    Inventor: Bobban Subhadra
  • 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: 20110160494
    Abstract: The present invention provides a process for improving the color of trimethylolpropane which comprises the steps of a) supplying a crude, aqueous base solution of trimethylolpropane, containing color causing impurities, and having a pH of less than about 9; b) contacting said base solution with an alkaline material for a period of time sufficient to increase the pH of said base solution to greater than 11 and at a sufficient temperature to allow the color causing impurities to react with said alkaline material; c) cooling the resulting solution from step (b) for a sufficient period of time; d) contacting said base solution of step (c) with an organic acid for a sufficient period of time to lower the pH thereof to less than about 9.
    Type: Application
    Filed: December 22, 2010
    Publication date: June 30, 2011
    Inventors: Kenneth A. Windhorst, David P. Harris, Marcos L. Schroeder, Fred Gaytan
  • Publication number: 20110118511
    Abstract: Methods of purifying BT are disclosed. The method comprises adding at least one polyhydroxyl compound to a crude BT mixture comprising BT and at least one boron-containing compound to form a polyhydroxyl compound/BT mixture. In one embodiment, the polyhydroxyl compound/BT mixture is then heated to a temperature greater than the boiling point of BT but less than the boiling point of the at least one polyhydroxyl compound. In another embodiment, the polyhydroxyl compound/BT mixture is heated to a temperature greater than the melting point of the polyhydroxyl compound, and then to a temperature greater than the boiling point of BT but less than the boiling point of the at least one polyhydroxyl compound. A composition comprising BT is also disclosed.
    Type: Application
    Filed: November 17, 2009
    Publication date: May 19, 2011
    Applicant: ALLIANT TECHSYSTEMS INC.
    Inventors: Stephen P. Velarde, Andrew J. Sanderson
  • Patent number: 7569736
    Abstract: The invention relates to a process for producing monopentaerythritol of high purity and monopentaerythritol produced by the process. Formaldehyde is reacted with acetaldehyde in an aqueous solution in the presence of a strongly basic hydroxide in a conventional way. The obtained reaction mixture is evaporated to a dryness of 50-70% by weight and is thereafter cooled. Crystals of pentaerythritol thereby formed are separated off. The crystals are dissolved in water or in a water-containing mother liquor containing pentaerythritol to a dryness of 35-55% by weight. The solution is treated in a purification step whereupon monopentaerythritol of high purity is crystallized at a temperature of 40-90° C. and separated from the remaining mother liquor which is recirculated to the above mentioned step.
    Type: Grant
    Filed: February 5, 2007
    Date of Patent: August 4, 2009
    Assignee: Perstorp Specialty Chemicals AB
    Inventors: Hans-Ake Bengtsson, Lars-Henrik Nyman
  • Patent number: 7569706
    Abstract: (wherein R represents a residue comprising a reactive group or a group capable of being transformed into the reactive group; n represents an integer of 3 or more; and X represents a residue capable of having the following structure by n in number: R1s each represent a hydrogen atom or a group capable of being transformed into a hydrogen atom, and 6 or more of R1s may be the same or different) The compound represented by the above formula (1), which is capable of modifying a physiologically active polypeptide or a derivative thereof, or a low molecular compound while maintaining the physiological activity, or which is useful for improving the stability or water-solubility of the low molecular compound, are provided.
    Type: Grant
    Filed: September 2, 2003
    Date of Patent: August 4, 2009
    Assignees: Kyowa Hakko Kirin Co., Ltd., Tecno Network Shikoku Co., Ltd.
    Inventors: Hisao Nemoto, Motoo Yamasaki, Toshiyuki Suzawa, Hiroyuki Yamaguchi
  • Publication number: 20090062575
    Abstract: The invention relates to a process for producing monopentaerythritol of high purity and monopentaerythritol produced by the process. Formaldehyde is reacted with acetaldehyde in an aqueous solution in the presence of a strongly basic hydroxide in a conventional way. The obtained reaction mixture is evaporated to a dryness of 50-70% by weight and is thereafter cooled. Crystals of pentaerythritol thereby formed are separated off. The crystals are dissolved in water or in a water-containing mother liquor containing pentaerythritol to a dryness of 35-55% by weight. The solution is treated in a purification step whereupon monopentaerythritol of high purity is crystallized at a temperature of 40-90° C. and separated from the remaining mother liquor which is recirculated to the above mentioned step.
    Type: Application
    Filed: February 5, 2007
    Publication date: March 5, 2009
    Applicant: PERSTORP SPECIALTY CHEMICALS AB
    Inventors: Hans-Ake Bengtsson, Lars-Henrik Nyman
  • Publication number: 20080275277
    Abstract: Processes for separating butanediols from glycols are disclosed, as well as products and compositions resulting therefrom.
    Type: Application
    Filed: October 29, 2007
    Publication date: November 6, 2008
    Inventor: Peter Kalagias
  • Publication number: 20080004475
    Abstract: A process is provided for the preparation of polymethylol compounds of formula (I): (HOCH2)2—C—(R)2 , ??(I) in which the radicals R independently of one another are each a further methylol group, an alkyl group having from 1 to 22 C atoms or an aryl or aralkyl group having from 6 to 22 C atoms, by (a) condensing aldehydes having from 2 to 24 C atoms with formaldehyde in an aldol reaction using tertiary amines as a catalyst to give alkanals of formula (II): in which the radicals R independently of one another are each as defined above, (b) then separating, by distillation, the reaction mixture obtained into a bottom product comprising predominantly the compounds of formula II and a low-boiling stream consisting of unconverted or partially converted starting materials, and (c) hydrogenating the distillation bottom, wherein the aldol reaction is carried out with an aqueous formaldehyde solution having a methanol content of 0.35 to 0.
    Type: Application
    Filed: June 28, 2006
    Publication date: January 3, 2008
    Applicant: BASF Aktiengesellschaft
    Inventors: Tilman Sirch, Michael Steiniger, Steffen Mass, Stefan Rittinger, Stephan Schlitter, Ludwig E. Heck, Todd C. Spengeman, Jeffrey T. Andress
  • Patent number: 7307194
    Abstract: The present invention provides a process for preparing 1,6-hexanediol from a carboxylic acid mixture which comprises adipic acid, 6-hydroxycaproic acid and small amounts of 1,4-cyclohexanediols and is obtained as a by-product in the oxidation of cyclohexane to cyclohexanone/cyclohexanol with oxygen or oxygen-containing gases and by water extraction of the reaction mixture, by esterification of the acids and hydrogenation, in which a) the mono- and dicarboxylic acids present in the aqueous dicarboxylic acid mixture are reacted with a low molecular weight alcohol to give the corresponding carboxylic esters, b) the resulting esterification mixture is freed of excess alcohol and low boilers in a first distillation stage, c) a separation of the bottom product is carried out in a second distillation stage into an ester fraction substantially free of 1,4-cyclohexanediols and a fraction comprising at least the majority of the 1,4-cyclohexanediols, d) the ester fraction substantially free of 1,4-cyclohexanediols is
    Type: Grant
    Filed: October 27, 2005
    Date of Patent: December 11, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Tilman Sirch, Gerd-Dieter Tebben, Ludwig E. Heck, Armin Diefenbacher, Alfred Krause, Franz Borgel
  • Patent number: 7301058
    Abstract: The invention relates to a method for increasing yield in the production of polyvalent alcohols, especially trimethylolpropane, obtained by condensing formaldehyde with a higher aldehyde. According to the inventive method, acid treatment is carried out on a mixture (high-boiling fraction) that is obtained by reprocessing, contains derivatives of said alcohols and has a higher boiling point than the respective alcohol, and the polyvalent alcohol is recovered from the acid-treated high-boiling fraction. The inventive method is characterised in that the water content of the high-boiling fraction amounts to between 20 and 90 wt. % in relation to the entire mixture of the high-boiling fraction and water.
    Type: Grant
    Filed: July 18, 2003
    Date of Patent: November 27, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Alexander Wartini, Tilman Sirch, Johann-Peter Melder, Matthias Dernbach
  • Patent number: 7253326
    Abstract: The present invention relates to a method for preparing trimethylolpropane (TMP) comprising the steps of: 1) synthesizing trimethylolpropane by using n-butyl aldehyde, an aqueous solution of formaldehyde and an aqueous solution of alkali metal hydroxide through aldol condensation reaction and Cannizzaro reaction; 2) extracting trimethylolpropane from a resultant mixture of the step 1) by contacting the resultant mixture with an alcohol having 6 to 10 carbons; 3) removing alkali metal ion from a resultant extract of the step 2) by contacting the resultant extract with water; and 4) distilling the alkali metal ion-removed extract obtained from the step 3).
    Type: Grant
    Filed: April 10, 2006
    Date of Patent: August 7, 2007
    Assignee: LG Chem, Ltd.
    Inventors: Sung Shik Eom, Dong Hyun Ko, Ji Joong Moon, Jae Hoon Choe, Dae Sun Rew
  • Patent number: 7211701
    Abstract: The present invention relates to a process for preparing trimethylolpropane having a low APHA color number.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: May 1, 2007
    Assignee: Lanxess Deutschland GmbH
    Inventors: Dirk Müller, Paul Wagner, Brian Schwegler, Ulrich Notheis, Ralph Armbrust, Hans-Detlef Heinz, Alexander Wagner
  • Patent number: 7211699
    Abstract: The invention discloses a hydrogenation process for removing impurities and controlling acid for use in downstream processing of biochemically-derived 1,3-propanediol. Preferably, the biochemically-derived 1,3-propanediol, before the contacting, has an initial color and, after the contracting, has a color that is lower than the initial color.
    Type: Grant
    Filed: August 12, 2005
    Date of Patent: May 1, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mayis Seapan, George F. Diffendall, Robert E. Trotter, Tyler T. Ames, F. Glenn Gallagher
  • Patent number: 7157607
    Abstract: A process of manufacture of polytrimethylene ether glycol comprising: (a) polycondensing reactant comprising diol selected from the group consisting of 1,3-propanediol, 1,3-propanediol dimer and 1,3-propanediol trimer or mixtures thereof in the presence of acid polycondensation catalyst to form polytrimethylene ether glycol; (b) adding water to the polytrimethylene ether glycol to form an aqueous mixture; (c) heating the aqueous mixture to hydrolyze acid esters formed during the acid catalyzed polycondensation; (d) adding to the hydrolyzed aqueous mixture organic solvent that is miscible with polytrimethylene ether glycol to form (i) organic phase containing the polytrimethylene ether glycol and residual acid polycondensation catalyst from the polycondensing and (ii) aqueous phase; (e) separating the aqueous phase and the organic phase; (f) adding base to the separated organic phase to neutralize the residual acid polycondensation catalyst by forming salts of the residual acid polycondensation catalyst; (g
    Type: Grant
    Filed: August 16, 2005
    Date of Patent: January 2, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Hari Babu Sunkara, Howard C. Ng, Wei Zheng
  • Patent number: 7112707
    Abstract: Trimethylolpropane is isolated from a reaction mixture which has been obtained by reaction of n-butyraldehyde with formaldehyde in the presence of a base and, if appropriate, hydrogenation of the resulting mixture by distilling the mixture by means of a dividing wall column or a distillation column with a precolumn or a distillation column with an after-column. The process has low capital costs and a low energy consumption and gives reduced formation of high-boiling by-products.
    Type: Grant
    Filed: December 6, 2002
    Date of Patent: September 26, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Tilman Sirch, Gerd Kaibel, Alexander Wartini, Matthias Dernbach
  • Patent number: 7098368
    Abstract: The invention discloses a hydrogenation process for removing impurities and controlling acid for use in downstream processing of biochemically-derived 1,3-propanediol. Preferably, the biochemically-derived 1,3-propanediol, before the contacting, has an initial color and, after the contracting, has a color that is lower than the initial color.
    Type: Grant
    Filed: May 5, 2004
    Date of Patent: August 29, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mayis Seapan, George F. Diffendall, Robert E. Trotter, Tyler T. Ames, F. Glenn Gallagher
  • Patent number: 7087800
    Abstract: A process for producing a polyol by reacting an aliphatic aldehyde with formaldehyde in the presence of a basic catalyst, which comprises a step of concentration which comprises removing water and unreacted formaldehyde from a reaction liquid by distillation; a step of extraction which comprises extracting the polyol from a concentrated reaction liquid with an extracting reagent; a step of washing with water which comprises washing an extract liquid with water and separating the liquid into an oil layer containing the polyol and an aqueous layer; wherein by useing an specific aliphatic aldehyde as the extracting agent and recovering the extracting reagent from the oil layer containing the polyol after adjusting pH of the oil layer, a high purity polyhydric alcohol can be obtained at a high yield with suppressed formation of byproducts such as acetal compounds and aldol compounds.
    Type: Grant
    Filed: June 6, 2001
    Date of Patent: August 8, 2006
    Assignee: Mitsubishi Gas Chemical Company, INC
    Inventors: Teruyuki Ninomiya, Toshio Watanabe, Atsushi Iwamoto, Soemu Miyashita, Masafumi Watanabe
  • Patent number: 7084311
    Abstract: Disclosed is a process comprising contacting chemical 1,3-propanediol with hydrogen in the presence of a hydrogenation catalyst. Preferably, the chemical 1,3-propanediol, before the contacting has an initial color and, after the contacting, has a color that is lower than the initial color.
    Type: Grant
    Filed: August 5, 2003
    Date of Patent: August 1, 2006
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Hari Babu Sunkara, Mayis Seapan, George F. Diffendall, Tyler T. Ames
  • Patent number: 7057080
    Abstract: A process is provided for improving the color number of polyhydric alcohols, especially trimethylolpropane, by catalytic hydrogenation, the polyhydric alcohol used in the hydrogenation having been purified by distillation following its preparation, wherein the hydrogenation is carried out in the presence of a macroporous supported heterogeneous catalyst containing, as the active metal, at least one metal of subgroups VII to X of the Periodic Table.
    Type: Grant
    Filed: October 11, 2001
    Date of Patent: June 6, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Dernbach, Christoph Sigwart, Michael Hesse, Steffen Maas
  • Patent number: 7038092
    Abstract: Disclosed is a process comprising contacting chemical 1,3-propanediol with hydrogen in the presence of a hydrogenation catalyst. Preferably, the chemical 1,3-propanediol, before the contacting has an initial color and, after the contacting, has a color that is lower than the initial color.
    Type: Grant
    Filed: August 12, 2005
    Date of Patent: May 2, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Hari Babu Sunkara, Mayis Seapan, George F. Diffendall, Tyler T. Ames
  • Patent number: 6914164
    Abstract: A method for removing trialkyl ammonium formate from a methylol alkanes obtained by condensation of formaldehyde with a higher aldehyde. The invention is characterized in that trialkyl ammonium formate is decomposed at a high temperature using catalysts containing at least one metal from groups 8-12 of the classification of elements in the presence of gas containing hydrogen. The method makes it possible to separate trialkyl ammonium formate according to the organic Cannizzaro method and according to the hydrogenation method.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: July 5, 2005
    Assignee: BASF AG
    Inventors: Michael Koch, Alexander Wartini, Tilman Sirch, Matthias Dernbach
  • Patent number: 6727395
    Abstract: A process for preparing 1,6-hexanediol from a carboxylic acid mixture comprising adipic acid, 6-hydroxycaproic acid and small amounts of 1,4-cyclohexanediols which is obtained as by-product in the oxidation of cyclohexane to cyclohexanone/cyclohexanol after water extraction of the reaction mixture followed by extraction with aqueous sodium hydroxide solution, by esterification of the acids and hydrogenation comprises a) liberating the carboxylic acids from the alkaline extract by addition of a mineral acid, b) fractionating the organic phase comprising carboxylic acids to give a distillate comprising the low molecular weight monocarboxylic acids and a residue comprising adipic acid and 6-hydroxycaproic acid, c) reacting the monocarboxylic an dicarboxylic acids present in the aqueous dicarboxylic acid mixture with a low molecular weight alcohol to give the corresponding carboxylic esters, d) freeing the esterification mixture obtained of excess alcohol and low boilers in a first distillation step, e) frac
    Type: Grant
    Filed: December 19, 2001
    Date of Patent: April 27, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Stein, Thomas Krug, Thomas Nöbel, Harald Rust
  • Patent number: 6692616
    Abstract: A process is disclosed for the purification, by distillation, of trimethylolpropane originating from the hydrogenation of 2,2-dimethylolbutanal, said process including the following steps: (a) reaction of n-butyraldehyde with formaldehyde in the presence of catalytic amounts of a tertiary amine, and hydrogenation of the resulting mixture to give a mixture containing trimethylolpropane; (b) separation of water, methanol, trialkylamine and/or trialkylammonium formate by distillation; (c) heating of the residue obtained in (b) under reduced pressure to a temperature at which TMP is volatile and compounds boiling above TMP are cleaved, in order to separate off, by distillation, TMP and compounds more volatile than TMP; (d) distillation of the distillate obtained in (c) in order to separate off the more volatile compounds and recover pure TMP; and (e) optional distillation of the TMP obtained in (d) in order to recover TMP with a low APHA color index.
    Type: Grant
    Filed: June 26, 2002
    Date of Patent: February 17, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Dernbach, Detlef Kratz, Achim Stammer, Harald Rust, Gerhard Schulz
  • Patent number: 6683224
    Abstract: Naturally occurring fats, oils and fatty derivatives are continuously hydrogenated to fatty alcohols in a fixed-bed reactor in the presence of hydrogen in excess and hydrogenation catalysts under static pressures of 50 to 300 bar and at temperatures of 160 to 320° C. The liquid product is cooled and the excess hydrogen is returned to the reactor entrance by a gas circulation pump as a recycle gas after separation of the liquid product. The expense involved in cooling and reheating the recycle gas is eliminated without any reduction in the quality of the fatty alcohol produced providing the recycle gas is returned to the reactor entrance without reheating and the hydrogenation reaction is carried out under static pressures of at least 200 bar.
    Type: Grant
    Filed: November 26, 2002
    Date of Patent: January 27, 2004
    Assignee: Cognis Deutschland GmbH & Co. KG
    Inventors: Roland Hourticolon, Guenther Demmering, Hans-Peter Kubersky, Lothar Friesenhagen, Friedrich Hommers, Juergen Latzel, Eberhard Peukert, Hans-Guenther Richard, Udo Kreutzer
  • Patent number: 6623649
    Abstract: A process is provided which makes it possible to separate off cyclic acetals from wastewater streams to a substantial extent, by passing the wastewater stream over a heterogeneous acid catalyst.
    Type: Grant
    Filed: June 5, 2001
    Date of Patent: September 23, 2003
    Assignee: BP Koln GmbH
    Inventors: Hans-Jurgen Bister, Alexander Gammersbach, Axel Gohrt, Joachim Grub, Stefanie Konig