Purification Or Recovery Patents (Class 568/854)
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Patent number: 10696785Abstract: A diol composition includes a diol as a major component and has an electrical conductivity of 0.6 to 30 mS/m.Type: GrantFiled: February 21, 2012Date of Patent: June 30, 2020Assignee: Toray Industries, Inc.Inventors: Masateru Ito, Izumi Morita, Kenji Kawamura, Tetsuya Yamada, Sadanori Kumazawa, Katsushige Yamada
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Patent number: 8987527Abstract: 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: GrantFiled: November 28, 2012Date of Patent: March 24, 2015Assignee: Oxea GmbHInventors: Guido D. Frey, Heinz Strutz
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Patent number: 8987523Abstract: 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: GrantFiled: July 28, 2011Date of Patent: March 24, 2015Assignee: Oxea GmbHInventors: Thorsten Kreickmann, Guido D. Frey, Norman Nowotny, Heinz Strutz
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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: 8907139Abstract: 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: GrantFiled: December 19, 2012Date of Patent: December 9, 2014Assignee: Celanese International CorporationInventors: Victor J. Johnston, David Lee, Adam Orosco, R. Jay Warner, Heiko Weiner, Zhenhua Zhou, Emily Duff, Radmila Jevtic
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Patent number: 8884076Abstract: 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: GrantFiled: December 7, 2009Date of Patent: November 11, 2014Assignee: BASF SEInventors: Tilman Sirch, Michael Steiniger, Steffen Maas, Stefan Rittinger, Stephan Schlitter
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Publication number: 20140296583Abstract: 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: ApplicationFiled: November 28, 2012Publication date: October 2, 2014Inventors: Guido D. Frey, Heinz Strutz
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Publication number: 20140288318Abstract: 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: ApplicationFiled: October 24, 2012Publication date: September 25, 2014Applicant: Oxea GmbHInventors: Guido D. Frey, Kurt Schalapski, Dirk Bermann, Norman Nowotney, Heinz Strutz, Donald K. Raff
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Patent number: 8759593Abstract: 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: GrantFiled: September 17, 2012Date of Patent: June 24, 2014Assignee: Oxea Bishop LLCInventors: Kenneth A. Windhorst, Oakley T. Cortez, Donald K. Raff
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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: 8686197Abstract: 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: GrantFiled: August 6, 2010Date of Patent: April 1, 2014Assignee: LANXESS Deutschland GmbHInventors: Ulrich Notheis, Hans-Dieter Gerriets, Michael Friederich
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Publication number: 20140081053Abstract: 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: ApplicationFiled: September 17, 2012Publication date: March 20, 2014Inventors: Kenneth A. Windhorst, Oakley T. Cortez, Donald K. Raff
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Publication number: 20140081052Abstract: 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: ApplicationFiled: September 17, 2012Publication date: March 20, 2014Inventors: Kenneth A. Windhorst, Oakley T. Cortez, Donald K. Raff
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Patent number: 8575401Abstract: 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: GrantFiled: December 7, 2009Date of Patent: November 5, 2013Assignee: BASF SEInventors: Tilman Sirch, Michael Steiniger, Steffen Maas, Stefan Rittinger
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Patent number: 8507734Abstract: 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: GrantFiled: March 3, 2011Date of Patent: August 13, 2013Assignee: Neonc Technologies Inc.Inventors: Thomas Chen, Daniel Levin, Satish Puppali
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Patent number: 8470566Abstract: 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: GrantFiled: February 10, 2012Date of Patent: June 25, 2013Assignee: Genomatica, Inc.Inventors: John D. Trawick, Mark J. Burk, Anthony P. Burgard
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Publication number: 20130131391Abstract: 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: ApplicationFiled: July 28, 2011Publication date: May 23, 2013Applicant: OXEA GMBHInventors: Thorsten Kreickmann, Guido D. Frey, Norman Nowotny, Heinz Strutz
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Patent number: 8394998Abstract: 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: GrantFiled: June 12, 2009Date of Patent: March 12, 2013Assignee: Oxea GmbHInventors: Kurt Schalapski, Tonia Kretz, Thorsten Kreickmann, Peter Heymanns, Rainer Lukas, Rolf-Peter Schulz
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Patent number: 8389778Abstract: 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: GrantFiled: May 21, 2008Date of Patent: March 5, 2013Assignee: Aptuit (West Lafayette), LLCInventors: Jan-Olav Henck, Mark C. Andres, Linda J. McCausland
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Patent number: 8354561Abstract: 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: GrantFiled: December 22, 2010Date of Patent: January 15, 2013Assignee: Oxea Bishop LLCInventors: Kenneth A. Windhorst, David P. Harris, Marcos L. Schroeder, Fred Gaytan
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Publication number: 20120271029Abstract: 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: ApplicationFiled: April 13, 2012Publication date: October 25, 2012Applicant: BASF SEInventors: Helmut Kronemayer, Michael Steiniger, Eva Kretzschmar, Norbert Asprion, Marcus Bechtel
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Patent number: 8293950Abstract: 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: GrantFiled: March 31, 2006Date of Patent: October 23, 2012Assignee: 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
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Patent number: 8143458Abstract: Processes for separating butanediols from glycols are disclosed, as well as products and compositions resulting therefrom.Type: GrantFiled: October 29, 2007Date of Patent: March 27, 2012Assignee: Archer Daniels Midland CompanyInventor: Peter Kalagias
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Publication number: 20120010435Abstract: The present invention relates to a method for isolating ditrimethylol propane from secondary trimethylol propane production streams.Type: ApplicationFiled: August 11, 2009Publication date: January 12, 2012Applicant: LANXESS DEUTSCHLAND GMBHInventors: Gunter Rauchschwalbe, Ulrich Notheis, Michael Friederich, Hans-Dieer Gerriets, Carsten Hummelt, Christiane Oppenheimer-Stix, Paul Wagner
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Publication number: 20110258915Abstract: 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: ApplicationFiled: October 19, 2009Publication date: October 27, 2011Applicant: STC.UNMInventor: Bobban Subhadra
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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: 20110160494Abstract: 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: ApplicationFiled: December 22, 2010Publication date: June 30, 2011Inventors: Kenneth A. Windhorst, David P. Harris, Marcos L. Schroeder, Fred Gaytan
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Publication number: 20110118511Abstract: 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: ApplicationFiled: November 17, 2009Publication date: May 19, 2011Applicant: ALLIANT TECHSYSTEMS INC.Inventors: Stephen P. Velarde, Andrew J. Sanderson
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Patent number: 7569706Abstract: (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: GrantFiled: September 2, 2003Date of Patent: August 4, 2009Assignees: Kyowa Hakko Kirin Co., Ltd., Tecno Network Shikoku Co., Ltd.Inventors: Hisao Nemoto, Motoo Yamasaki, Toshiyuki Suzawa, Hiroyuki Yamaguchi
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Patent number: 7569736Abstract: 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: GrantFiled: February 5, 2007Date of Patent: August 4, 2009Assignee: Perstorp Specialty Chemicals ABInventors: Hans-Ake Bengtsson, Lars-Henrik Nyman
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Publication number: 20090062575Abstract: 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: ApplicationFiled: February 5, 2007Publication date: March 5, 2009Applicant: PERSTORP SPECIALTY CHEMICALS ABInventors: Hans-Ake Bengtsson, Lars-Henrik Nyman
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Publication number: 20080275277Abstract: Processes for separating butanediols from glycols are disclosed, as well as products and compositions resulting therefrom.Type: ApplicationFiled: October 29, 2007Publication date: November 6, 2008Inventor: Peter Kalagias
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Publication number: 20080004475Abstract: 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: ApplicationFiled: June 28, 2006Publication date: January 3, 2008Applicant: BASF AktiengesellschaftInventors: Tilman Sirch, Michael Steiniger, Steffen Mass, Stefan Rittinger, Stephan Schlitter, Ludwig E. Heck, Todd C. Spengeman, Jeffrey T. Andress
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Patent number: 7307194Abstract: 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 isType: GrantFiled: October 27, 2005Date of Patent: December 11, 2007Assignee: BASF AktiengesellschaftInventors: Tilman Sirch, Gerd-Dieter Tebben, Ludwig E. Heck, Armin Diefenbacher, Alfred Krause, Franz Borgel
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Patent number: 7301058Abstract: 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: GrantFiled: July 18, 2003Date of Patent: November 27, 2007Assignee: BASF AktiengesellschaftInventors: Alexander Wartini, Tilman Sirch, Johann-Peter Melder, Matthias Dernbach
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Patent number: 7253326Abstract: 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: GrantFiled: April 10, 2006Date of Patent: August 7, 2007Assignee: LG Chem, Ltd.Inventors: Sung Shik Eom, Dong Hyun Ko, Ji Joong Moon, Jae Hoon Choe, Dae Sun Rew
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Patent number: 7211699Abstract: 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: GrantFiled: August 12, 2005Date of Patent: May 1, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Mayis Seapan, George F. Diffendall, Robert E. Trotter, Tyler T. Ames, F. Glenn Gallagher
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Patent number: 7211701Abstract: The present invention relates to a process for preparing trimethylolpropane having a low APHA color number.Type: GrantFiled: December 18, 2002Date of Patent: May 1, 2007Assignee: Lanxess Deutschland GmbHInventors: Dirk Müller, Paul Wagner, Brian Schwegler, Ulrich Notheis, Ralph Armbrust, Hans-Detlef Heinz, Alexander Wagner
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Patent number: 7157607Abstract: 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; (gType: GrantFiled: August 16, 2005Date of Patent: January 2, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Hari Babu Sunkara, Howard C. Ng, Wei Zheng
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Patent number: 7112707Abstract: 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: GrantFiled: December 6, 2002Date of Patent: September 26, 2006Assignee: BASF AktiengesellschaftInventors: Tilman Sirch, Gerd Kaibel, Alexander Wartini, Matthias Dernbach
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Patent number: 7098368Abstract: 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: GrantFiled: May 5, 2004Date of Patent: August 29, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: Mayis Seapan, George F. Diffendall, Robert E. Trotter, Tyler T. Ames, F. Glenn Gallagher
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Patent number: 7087800Abstract: 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: GrantFiled: June 6, 2001Date of Patent: August 8, 2006Assignee: Mitsubishi Gas Chemical Company, INCInventors: Teruyuki Ninomiya, Toshio Watanabe, Atsushi Iwamoto, Soemu Miyashita, Masafumi Watanabe
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Patent number: 7084311Abstract: 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: GrantFiled: August 5, 2003Date of Patent: August 1, 2006Assignee: E. I. Du Pont de Nemours and CompanyInventors: Hari Babu Sunkara, Mayis Seapan, George F. Diffendall, Tyler T. Ames
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Patent number: 7057080Abstract: 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: GrantFiled: October 11, 2001Date of Patent: June 6, 2006Assignee: BASF AktiengesellschaftInventors: Matthias Dernbach, Christoph Sigwart, Michael Hesse, Steffen Maas
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Patent number: 7038092Abstract: 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: GrantFiled: August 12, 2005Date of Patent: May 2, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: Hari Babu Sunkara, Mayis Seapan, George F. Diffendall, Tyler T. Ames
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Patent number: 6914164Abstract: 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: GrantFiled: October 18, 2002Date of Patent: July 5, 2005Assignee: BASF AGInventors: Michael Koch, Alexander Wartini, Tilman Sirch, Matthias Dernbach
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Patent number: 6727395Abstract: 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) fracType: GrantFiled: December 19, 2001Date of Patent: April 27, 2004Assignee: BASF AktiengesellschaftInventors: Frank Stein, Thomas Krug, Thomas Nöbel, Harald Rust
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Patent number: 6692616Abstract: 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: GrantFiled: June 26, 2002Date of Patent: February 17, 2004Assignee: BASF AktiengesellschaftInventors: Matthias Dernbach, Detlef Kratz, Achim Stammer, Harald Rust, Gerhard Schulz
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Patent number: 6683224Abstract: 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: GrantFiled: November 26, 2002Date of Patent: January 27, 2004Assignee: Cognis Deutschland GmbH & Co. KGInventors: Roland Hourticolon, Guenther Demmering, Hans-Peter Kubersky, Lothar Friesenhagen, Friedrich Hommers, Juergen Latzel, Eberhard Peukert, Hans-Guenther Richard, Udo Kreutzer
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Patent number: 6623649Abstract: 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: GrantFiled: June 5, 2001Date of Patent: September 23, 2003Assignee: BP Koln GmbHInventors: Hans-Jurgen Bister, Alexander Gammersbach, Axel Gohrt, Joachim Grub, Stefanie Konig