Polyoxy Containing Reactant Patents (Class 568/486)
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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: 20110288323Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerine, comprising dehydrating glycerol or glycerine in the presence of a catalyst consisting of at least a) a mixed oxide of zirconium and at least one metal, said metal being selected from niobium, tantalum and vanadium, b) a zirconium oxide and at least one metal oxide, the metal being selected from niobium, tantalum and vanadium, c) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, d) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, vanadium and titanium, e) a titanium oxide and a mixed oxide of zirconium and at least one metal, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, f) a titanium oxide and a mixed oxide or zirconium and at least onType: ApplicationFiled: December 16, 2009Publication date: November 24, 2011Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, ADISSEO FRANCE S.A.SInventors: Virginie Belliere-Baca, Stephane Loridant, Jean-Marc Millet, Pascaline Lauriol-Garbey
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Publication number: 20110275777Abstract: The invention relates to a method for producing acrolein, comprising the following steps: (a) dehydrating an aqueous glycerin phase G1 in an acrolein reaction region, obtaining an aqueous acrolein reaction phase; (b) at least partially separating the aqueous acrolein reaction phase into an acrolein-rich acrolein phase and an acrolein-poor (in comparison to the acrolein phase) residual phase R1, wherein the residual phase R1 comprises glycerin, water and various remainders from glycerin and water; (c) recycling at least a part of the residual phase R2 in step (a); wherein i) from a glycerin phase G2 comprising remainders that differ from glycerin and water, at least one of said remainders is separated and the thus obtained, purified glycerin phase G2 is immediately supplied to the acrolein reaction region, or ii) at least one remainder different from glycerin and water is separated out of a mixture phase M1 obtained by mixing a glycerin phase G2 with the acrolein-poor residual phase R1, and the thus obtained,Type: ApplicationFiled: November 3, 2009Publication date: November 10, 2011Inventors: Guido Stochniol, Goetz Baumgarten, Franz-Felix Kuppinger
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Publication number: 20110237828Abstract: Disclosed are an acrolein production method capable of producing acrolein from a glycerin mixture including either one or both of a fatty acid and a fatty acid salt, a glycerin; a fatty acid ester, and the like with a little consumption of energy, and an acrylic acid production method. Specifically disclosed is an acrolein production method having the steps of: dehydrating glycerin in the glycerin mixture to produce an acrolein mixture including acrolein; either one of a fatty acid and a fatty acid salt, and the like; and collecting acrolein from the acrolein mixture. Also specifically disclosed is an acrylic acid production method having the step of reacting acrolein produced by the acrolein production method with molecular oxygen.Type: ApplicationFiled: August 20, 2008Publication date: September 29, 2011Applicant: SHOWA DENKO K.K.Inventors: Takanori Aoki, Norihide Arai
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Publication number: 20110213174Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerol in the presence of a catalyst system comprising oxygen, phosphorus and at least one metal chosen from vanadium, boron or aluminium. The process is preferably carried out in the gas phase in the presence of oxygen starting from aqueous solutions of glycerol.Type: ApplicationFiled: October 5, 2009Publication date: September 1, 2011Applicant: Arkema FranceInventor: Jean-Luc Dubois
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Patent number: 7994368Abstract: A process for the selective production of acetaldehyde by vapor phase reaction of acetic acid over a hydrogenating catalyst composition to form acetaldehyde is disclosed and claimed. In an embodiment of this invention reaction of acetic acid and hydrogen over platinum and iron supported on silica selectively produces acetaldehyde in a vapor phase at a temperature of about 300° C.Type: GrantFiled: September 16, 2010Date of Patent: August 9, 2011Assignee: Celanese International CorporationInventors: Victor J. Johnston, James H. Zink, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, Jan Cornelis van der Waal, Virginie Zuzaniuk
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Publication number: 20110160491Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerin, characterized in that the dehydration is carried out in the presence of a catalyst comprising mainly a compound in which protons in a heteropolyacid are exchanged at least partially with at least one cation selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements. The process according to the invention permits to obtain acrolein at higher yield.Type: ApplicationFiled: April 14, 2009Publication date: June 30, 2011Applicant: Arkema FranceInventors: Jean-Luc Dubois, Yasuhiro Magatani, Kimoto Okumura
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Patent number: 7951978Abstract: The present invention provides a process for producing acrolein, which exhibits a prolonged catalyst life, low energy consumption, and excellent efficiency, and which is earth-conscious, and a glycerin-containing composition which can preferably be used even in this process. The process for producing acrolein is one which includes bringing a raw material gas containing glycerin gas into contact with a solid acid catalyst in a reactor, and the partial pressure of the glycerin gas in the raw material gas is set to be from 0.01 to 30 kPa. The glycerin-containing composition is for use in a process for producing acrolein using a solid catalyst and includes a fatty acid and/or a fatty acid ester, and a total mass of the fatty acid and the fatty acid ester is from 0.001% to 5% by mass, relative to the glycerin.Type: GrantFiled: November 28, 2007Date of Patent: May 31, 2011Assignee: Nippon Shokubai Co., Ltd.Inventors: Yoshitaka Arita, Hideaki Tsuneki, Hiroto Kasuga, Masaki Okada, Masaru Kirishiki
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Publication number: 20110112330Abstract: Catalyst used in a process for preparing acrolein and acrylic acid at higher yield to convert glycerin to valuable other chemical raw materials. The glycerin dehydration catalyst consists mainly of a compound containing at least one element selected from Mo, W and V, in which protons in the heteropolyacid are exchanged at least partially with at least one cation selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements.Type: ApplicationFiled: April 14, 2009Publication date: May 12, 2011Applicant: NIPPON KAYAKU KABUSHIKI KAISHAInventors: Yasuhiro Magatani, Kimito Okumura
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Publication number: 20110087050Abstract: The present invention relates to a method for producing acrolein, comprising step (1) of subjecting glycerol to dehydration reaction in the presence of a copper compound and a compound containing a heteroatom; step (2) of recovering acrolein generated in the dehydration reaction step (1); step (3) of recovering part or all of the copper compound which remained after the recovery of acrolein; step (4) of treating part or all of the recovered copper compound with at least one member selected from a group consisting of an oxidizing agent and acid; and step (5) of returning part or all of the copper compound treated in the above step to step (1); and a method for producing acrylic acid, comprising reacting acrolein obtained by the above method with molecular oxygen.Type: ApplicationFiled: June 4, 2009Publication date: April 14, 2011Applicant: SHOWA DENKO K.K.Inventors: Takanori Aoki, Masayuki Yoshimura
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Publication number: 20110028760Abstract: The subject of the present invention is a method for the reactive vaporization of aqueous solutions of glycerol in a fluidized bed containing a reactive solid. The method of the invention makes it possible to simultaneously vaporize an aqueous solution of glycerol, to remove the impurities that are present in this solution or that are generated during the evaporation, and to carry out the dehydration reaction of the glycerol to acrolein and/or the oxydehydration reaction of the glycerol to acrylic acid.Type: ApplicationFiled: September 5, 2008Publication date: February 3, 2011Applicant: ARKEMA FRANCEInventors: Jean-Luc Dubois, Grégory Patience
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Patent number: 7872158Abstract: Chemical production processes are provided that can include exposing a reactant composition to a catalyst composition to form a product composition. The reactant composition can include a multihydric alcohol compound and the product composition can include a carbonyl compound. The catalyst composition can include a metal effective to facilitate catalyst activation. Processes disclosed also include supplementing a dehydration catalyst with a promoter, and activating the supplemented catalyst in the presence of oxygen. Processes also include providing a supplemented dehydration catalyst to within a reactor, and exposing a multihydric alcohol compound to the dehydration catalyst, with the exposing forming coke within the reactor. Oxygen can be provided to the reactor to remove at least a portion of the coke.Type: GrantFiled: August 24, 2007Date of Patent: January 18, 2011Assignee: Battelle Memorial InstituteInventors: Thomas H. Peterson, Alan H. Zacher, Michel J. Gray, James F. White, Todd A. Werpy
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Patent number: 7872159Abstract: Chemical production processes are provided that can include exposing a reactant composition to a catalyst composition to form a product composition. Catalyst compositions are also provided that can include metal phosphate compositions, metal phosphorous compositions, and/or solid support compositions with the solid support compositions including one or more of F—Al2O3, ZrO2—CO2, SiO2—Al2O3—CO2, SiO2 Al2O3, Alundum, and Silica such as Ludox AS-30.Type: GrantFiled: August 24, 2007Date of Patent: January 18, 2011Assignee: Battelle Memorial InstituteInventors: Thomas H. Peterson, Alan H. Zacher, Michel J. Gray, James F. White, Todd A. Werpy
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Patent number: 7847131Abstract: There is provided a process for producing acrolein, which makes it possible to obtain acrolein in high yield by dehydration of glycerin. Glycerin is allowed to coexist with a catalyst containing a rare earth metal salt crystal of phosphoric acid, thereby dehydrating the glycerin, wherein the crystal is obtained by calcining a solid which is formed by allowing a liquid containing water and a hydroxide of the rare earth metal and/or a dehydration condensate of the hydroxide to contain phosphate ions.Type: GrantFiled: May 15, 2008Date of Patent: December 7, 2010Assignee: Nippon Shokubai Co., Ltd.Inventors: Yoshitaka Arita, Tsukasa Takahashi, Masaki Okada, Toshimitsu Moriguchi
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Publication number: 20100280276Abstract: What is described is a process for preparing 2-hydroxyacetals of the general formula in which R1 is hydrogen, a branched or unbranched C1-C12-alkyl radical, an electron-deficient, halogen-, NO2—, CN—, CF3—, acyl group- or branched or unbranched alkyl group-substituted or unsubstituted C5-C6-aryl or heteroaryl, and R2 is a branched or unbranched C1-C5-alkyl radical, or both R2 radicals are bonded directly to one another or to one another via a C1-C4 unit, by reacting an enol compound of the general formula (II) in which R3 is the same and R1 is as defined for formula (Ia), with bromine to give the corresponding dibromo adduct and then reacting this dibromo adduct with an alkoxide of the general formula (III) M-O—R2 (III) in which R2 is as defined for formula (Ia) and O is oxygen and M is lithium, sodium or potassium. What is likewise described is the preparation of the corresponding 2-hydroxyalkanals from the 2-hydroxyacetals thus obtained by acidic hydrolysis.Type: ApplicationFiled: June 11, 2008Publication date: November 4, 2010Applicant: SALTIGO GMBHInventors: Thomas-Norbert Mueller, Michael Dockner
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Publication number: 20100274038Abstract: The invention provides a technology for producing acrolein from glycerol while maintaining high reagent partial pressures, which leads to higher yield. The invention more particularly relates to a method for producing acrolein from glycerol that comprises the intermediate step of forming glycerol and acrolein cyclic acetals.Type: ApplicationFiled: December 16, 2008Publication date: October 28, 2010Applicant: Arkema FranceInventor: Jean-Luc Dubois
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Patent number: 7816565Abstract: A process for the selective production of acetaldehyde by vapor phase reaction of acetic acid over a hydrogenating catalyst composition to form acetaldehyde is disclosed and claimed. In an embodiment of this invention reaction of acetic acid and hydrogen over platinum and iron supported on silica selectively produces acetaldehyde in a vapor phase at a temperature of about 300° C.Type: GrantFiled: July 31, 2008Date of Patent: October 19, 2010Assignee: Celanese International CorporationInventors: Victor J. Johnston, James H. Zink, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, Jan Cornelis van der Waal, Virginie Zuzaniuk
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Patent number: 7790934Abstract: A process for preparing acrolein from glycerol using an acidic solid-state catalyst which comprises tungsten compounds and further promoters.Type: GrantFiled: January 15, 2010Date of Patent: September 7, 2010Assignee: Evonik Degussa GmbHInventors: Hubert Redlingshöfer, Christoph Weckbecker, Klaus Huthmacher, Andreas Dörflein
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Publication number: 20100204502Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerol in the presence of a catalyst system based on iron phosphorous oxide containing, in addition, one or more elements chosen from alkali metals, alkaline-earth metals, AI, Si, B, Co, Cr, Ni, V, Zn, Zr, Sn, Sb, Ag, Cu, Nb, Mo, Y, Mn, Pt, Rh and the rare earths La, Ce, Sm. The process is preferably carried out in the gas phase in the presence of oxygen starting from aqueous solutions of glycerol. The process according to the invention makes it possible of obtain high acrolein selectivities.Type: ApplicationFiled: September 11, 2008Publication date: August 12, 2010Applicant: Arkema FranceInventor: Jean-Luc Dubois
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Publication number: 20100168472Abstract: The present invention relates to a process for producing acrolein by liquid phase dehydration of glycerol by preparing a mixture of a catalyst suspended in an organic solvent comprising one or more vinyl polymers and glycerol; and then mixing and heating the mixture to between 150° C. and 350° C. to dehydrate the glycerol and form acrolein. The vinyl polymers are selected from the group consisting of polyolefins, polystyrene, and mixtures thereof. The polyolefins may be polyethylene, polypropylene, polybutylene, polyisobutylene, polyisoprene, polypentene, or mixtures thereof. The acrolein may be subjected to vapor phase oxidation in the presence of a catalyst, such as a mixed metal oxide, to produce acrylic acid.Type: ApplicationFiled: November 20, 2009Publication date: July 1, 2010Inventors: Leonard Edward Bogan, JR., Mark Anthony Silvano
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Patent number: 7737306Abstract: One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.Type: GrantFiled: October 22, 2008Date of Patent: June 15, 2010Assignee: Suterra, LLCInventors: Andrew Thompson, Shawn Zhang, Lonnie Robarge
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Patent number: 7718829Abstract: The present invention has an object to provide a production method of acrolein capable of producing acrolein with suppressing the yield change with time. The production method of the invention is that glycerin is dehydrated under coexistence with a catalyst having crystalline metallosilicates containing at least one kind of T atoms and 15% by mass or less of a binder, and the Si atoms to T atoms ratio (Si/T) of the catalyst is 800 or less.Type: GrantFiled: May 11, 2007Date of Patent: May 18, 2010Assignee: Nippon Shokubai Co., Ltd.Inventors: Okuno Masaaki, Matsunami Etsushige, Takahashi Tsukasa, Kasuga Hiroto, Okada Masaki, Kirishiki Masaru
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Publication number: 20100113838Abstract: There is provided a process for producing acrolein, which makes it possible to obtain acrolein in high yield by dehydration of glycerin. Glycerin is allowed to coexist with a catalyst containing a rare earth metal salt crystal of phosphoric acid, thereby dehydrating the glycerin, wherein the crystal is obtained by calcining a solid which is formed by allowing a liquid containing water and a hydroxide of the rare earth metal and/or a dehydration condensate of the hydroxide to contain phosphate ions.Type: ApplicationFiled: May 15, 2008Publication date: May 6, 2010Applicant: NIPPON SHOKUBAI CO., LTD.Inventors: Yoshitaka Arita, Tsukasa Takahashi, Masaki Okada, Toshimitsu Moriguchi
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Publication number: 20100113833Abstract: A process for preparing acrolein from glycerol using an acidic solid-state catalyst which comprises tungsten compounds and further promoters.Type: ApplicationFiled: January 15, 2010Publication date: May 6, 2010Inventors: Hubert Redlingshöfer, Christoph Weckbecker, Klaus Huthmacher, Andreas Dörflein
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Publication number: 20100105957Abstract: The present invention provides a process for producing acrolein, which exhibits a prolonged catalyst life, low energy consumption, and excellent efficiency, and which is earth-conscious, and a glycerin-containing composition which can preferably be used even in this process. The process for producing acrolein is one which includes bringing a raw material gas containing glycerin gas into contact with a solid acid catalyst in a reactor, and the partial pressure of the glycerin gas in the raw material gas is set to be from 0.01 to 30 kPa. The glycerin-containing composition is for use in a process for producing acrolein using a solid catalyst and includes a fatty acid and/or a fatty acid ester, and a total mass of the fatty acid and the fatty acid ester is from 0.001% to 5% by mass, relative to the glycerin.Type: ApplicationFiled: November 28, 2007Publication date: April 29, 2010Inventors: Yoshitaka Arita, Hideaki Tsuneki, Hiroto Kasuka, Masaki Okada, Masaru Kirshiki
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Patent number: 7683220Abstract: There is provided a process for producing acrolein from glycerin, exhibiting a suppressed decrease in the yield of acrolein with time. In the process for producing acrolein by dehydrating glycerin in the presence of a catalyst containing a metal phosphate, one, or two or more, metal phosphates are used, which are selected from aluminum salts, zirconium salts, manganese salts, alkali metal salts (provided that the alkali metal is sodium, potassium, or cesium, and the ratio between the mole number (M) of the alkali metal and the mole number (P) of phosphoric acid (i.e., M/P ratio) in the metal phosphate is 2.0 or lower), alkali earth metal salts (provided that the ratio between the mole number (M) of the alkali earth metal and the mole number (P) of phosphoric acid (i.e., M/P ratio) in the metal phosphate is 1.0 or lower), and the like.Type: GrantFiled: March 27, 2007Date of Patent: March 23, 2010Assignee: Nippon Shokubai Co., Ltd.Inventors: Etsushige Matsunami, Tsukasa Takahashi, Hiroto Kasuga, Yoshitaka Arita
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Patent number: 7655818Abstract: The present invention relates to a process for manufacturing acrolein by gas-phase dehydration of glycerol in the presence of strongly acidic solid catalysts with a Hammett acidity H0 of between ?9 and ?18 and preferably between ?10 and ?16.Type: GrantFiled: January 6, 2006Date of Patent: February 2, 2010Assignee: Arkema FranceInventors: Jean-Luc Dubois, Christophe Duquenne, Wolfgang Holderich, Jacques Kervennal
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Patent number: 7582799Abstract: The present invention provides an industrially advantageous process for producing hydrazone derivative represented by the formula (5), which is shown by the following reaction formula.Type: GrantFiled: April 27, 2006Date of Patent: September 1, 2009Assignees: Shiratori Pharmaceutical Co., Ltd., Asubio Pharma Co., Ltd.Inventors: Hiroshi Yoshino, Kentaro Kobayashi, Yuichi Shiro
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Publication number: 20090177015Abstract: The present invention has an object to provide a production method of acrolein capable of producing acrolein with suppressing the yield change with time. The production method of the invention is that glycerin is dehydrated under coexistence with a catalyst having crystalline metallosilicates containing at least one kind of T atoms and 15% by mass or less of a binder, and the Si atoms to T atoms ratio (Si/T) of the catalyst is 800 or less.Type: ApplicationFiled: May 11, 2007Publication date: July 9, 2009Inventors: Okuno Masaaki, Matsunami Etsushige, Takahashi Tsukasa, Kasuga Hiroto, Okada Masaki, Kirishiki Masaru
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Publication number: 20090118549Abstract: There is provided a process for producing acrolein from glycerin, exhibiting a suppressed decrease in the yield of acrolein with time. In the process for producing acrolein by dehydrating glycerin in the presence of a catalyst containing a metal phosphate, one, or two or more, metal phosphates are used, which are selected from aluminum salts, zirconium salts, manganese salts, alkali metal salts (provided that the alkali metal is sodium, potassium, or cesium, and the ratio between the mole number (M) of the alkali metal and the mole number (P) of phosphoric acid (i.e., M/P ratio) in the metal phosphate is 2.0 or lower), alkali earth metal salts (provided that the ratio between the mole number (M) of the alkali earth metal and the mole number (P) of phosphoric acid (i.e., M/P ratio) in the metal phosphate is 1.0 or lower), and the like.Type: ApplicationFiled: March 27, 2007Publication date: May 7, 2009Inventors: Etsushige Matsunami, Tsukasa Takahashi, Hiroto Kasuga, Yoshitaka Arita
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Publication number: 20090076305Abstract: The present invention provides an industrially advantageous process for producing hydrazone derivative represented by the formula (5), which is shown by the following reaction formula.Type: ApplicationFiled: April 27, 2006Publication date: March 19, 2009Applicants: Shiratori Pharmaceutical Co., Ltd., Asubio Pharma Co., Ltd.Inventors: Hiroshi Yoshino, Kentaro Kobayashi, Yuichi Shiro
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Publication number: 20080319233Abstract: The invention relates to a method for preparing acrolein from propylene, consisting of a first glycerol dehydration step preformed in the presence of a gas containing propylene and, more specifically, in the presence of the reaction gas originating from the propylene to acrolein oxidation step. The inventive method enables the use, in part, of renewable raw material, while increasing acrolein production.Type: ApplicationFiled: February 6, 2007Publication date: December 25, 2008Applicant: Arkema FranceInventor: Jean-Luc Dubois
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Publication number: 20080315151Abstract: 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: ApplicationFiled: August 28, 2006Publication date: December 25, 2008Inventors: Galen J. Suppes, William Rusty Sutterlin
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Patent number: 7396962Abstract: The present invention relates to a process for manufacturing acrolein by dehydration of glycerol in the presence of molecular oxygen. The reaction is performed in the liquid phase or in the gas phase in the presence of a solid catalyst. The addition of oxygen makes it possible to obtain good glycerol conversion by inhibiting the deactivation of the catalyst and the formation of by-products.Type: GrantFiled: January 6, 2006Date of Patent: July 8, 2008Assignee: Arkema FranceInventors: Jean-Luc Dubois, Christophe Duquenne, Wolfgang Holderich
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Patent number: 7339085Abstract: The present invention relates to an improved process for preparing 2,7-dimethylocta-2,4,6-trienedial of the formula I, by a) double enol ether condensation of a butenedial bisacetal of the formula II with an enol ether of the formula III, ?in the presence of a Lewis acid catalyst to give a condensation product of the formula IV, ?where the radicals R1 and R2 in formulae II to IV are independently of one another C1-C6-alkyl; b) hydrolysis of the acetal groups of IV by adding an aqueous acid to form the dialdehyde of the formula V; d) crystallization of I from the reaction mixture, Wherein process steps a) to d) are carried out in the presence of an inert, water-immiscible organic solvent.Type: GrantFiled: February 4, 2005Date of Patent: March 4, 2008Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Klaus Henrich, Andreas Keller
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Patent number: 7161030Abstract: Hydrofluoroethers of formula: T-CFX?—O—Rf—CFX-T???(II) wherein: T=CH3; X, X?, equal to or different from each other, are selected between F, CF3; T00?=F, Cl, H, C1–C3 perfluoroalkyl, CH3, CH2OH, COCl, CHO, CO2H; Rf is a perfluoroalkylene or a perfluoropolyoxyalkylene and respective preparation process by reduction with hydrogen in the presence of a platinum catalyst supported on metal fluorides of the corresponding compounds with at least one —COCl end group.Type: GrantFiled: July 31, 2003Date of Patent: January 9, 2007Assignee: Solvay Solexis S.p.A.Inventors: Rosaldo Picozzi, Antonella Di Meo, Claudio Tonelli
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Patent number: 6864327Abstract: This invention provides a method for preparing, in high purity and high yield, heterobifunctional derivatives of poly(ethylene glycol) or related polymers. A chromatographic purification step is not necessary in the method. In accordance with the method of the invention, an intermediate polymer having a formula of W-Poly-OH is provided bearing a removable group W at one terminus. The intermediate polymer W-Poly-OH is first altered by modifying the OH group to a first functional group X, followed by the removal of W to generate a second hydroxyl group. The latter hydroxyl group may then be further converted to a second functional group Y, thus providing the desired heterobifunctional derivative.Type: GrantFiled: February 8, 2002Date of Patent: March 8, 2005Assignee: Nektar Therapeutics AL, CorporationInventors: Michael David Bentley, J. Milton Harris, Antoni Kozlowski
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Patent number: 6448369Abstract: This invention provides a method for preparing, in high purity and high yield, heterobifunctional derivatives of poly(ethylene glycol) or related polymers. A chromatographic purification step is not necessary in the method. In accordance with the method of the invention, an intermediate polymer having a formula of W-Poly-OH is provided bearing a removable group W at one terminus. The intermediate polymer W-Poly-OH is first altered by modifying the OH group to a first functional group X, followed by the removal of W to generate a second hydroxyl group. The latter hydroxyl group may then be further converted to a second functional group Y, thus providing the desired heterobifunctional derivative.Type: GrantFiled: November 5, 1998Date of Patent: September 10, 2002Assignee: Shearwater CorporationInventors: Michael David Bentley, J. Milton Harris, Antoni Kozlowski
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Patent number: 6376718Abstract: A catalytic dehydrogenation of alkylene glycol ether to ether ketone or aldehyde is disclosed. The dehydrogenation is performed with copper chromite catalyst and at least 5 wt % of water based on alkylene glycol ether. It has been found that the selectivity to formation of ether ketone or aldehyde increases with increasing the amount of water in the alkylene glycol ether.Type: GrantFiled: November 17, 2000Date of Patent: April 23, 2002Assignee: Arco Chemical Technology, L.P.Inventor: Prakash Balan
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Patent number: 6175044Abstract: 3,7-Dimethyl-2,6-octadien-1-al of formula I is prepared continuously by: thermally cleaving, in the presence or absence of an acid catalyst, 3-methyl-2-buten-1-al diprenyl acetal of formula II: thereby eliminating 3-methyl-2-buten-1-ol of formula III and yielding cis/trans-prenyl 3-methylbutadienyl ether of formula IV: thermally rearranging the resultant butadienyl ether of formula IV thereby yielding 2,4,4-trimethyl-3-formyl-1,5-hexadiene of formula V: subsequently rearranging intermediate (V) thereby yielding citral product of formula I, which comprises: as the reaction proceeds, continuously distilling the reaction mixture thereby continuously removing prenol, which is formed by degradation of acetal II, and the intermediates of formula IV and V and any citral product which is formed during the reaction; and thermally rearranging said intermediates of formula IV and V at a temperature of 100-200° C.Type: GrantFiled: September 24, 1999Date of Patent: January 16, 2001Assignee: BASF AktiengesellschaftInventors: Jörg Therre, Gerd Kaibel, Werner Aquila, G{umlaut over (u)}nter Wegner, Hartwig Fuchs
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Patent number: 6080898Abstract: A process for the catalytic hydrogenolysis of glycerol in the presence of a homogeneous catalyst that is based on a platinum group metal or a compound of a platinum group metal, an anion source, and a metal-complexing compound of the formula Q.sup.1 Q.sup.2 MQ.sup.3 (I) or Q.sup.1 Q.sup.2 MQMQ.sup.3 Q.sup.4 (II) wherein M represents phosphorus, arsenic or antimony, Q represents a group that is covalently bonded to both M's and having at least two carbon atoms in the bridge and Q.sup.1 to Q.sup.4 are independently similar or dissimilar optionally substituted hydrocarbyl groups or Q.sup.1 and Q.sup.2 and/or Q.sup.3 and Q.sup.4 represent similar or dissimilar optionally substituted hydrocarbylene groups.Type: GrantFiled: July 23, 1998Date of Patent: June 27, 2000Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
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Patent number: 5786518Abstract: A novel process for the manufacture of a .gamma.-halotiglic aldehyde HalH.sub.2 C--CH.dbd.C(CH.sub.3)--CHO ?I!, wherein Hal signifies chlorine or bromine, comprises haloalkoxylating a 1-alkoxy-2-methyl-1,3-butadiene H.sub.2 C.dbd.CH--C(CH.sub.3).dbd.CH--OR.sup.1 ?II!, wherein R.sup.1 signifies C.sub.1-4 -alkyl, using a particular halogenating agent in a C.sub.1-4 -alkanol (R.sup.2 OH) and hydrolyzing the thus-obtained .gamma.-halotiglic aldehyde dialkyl acetal HalH.sub.2 C--CH.dbd.C(CH.sub.3)--CH(OR.sup.1)(OR.sup.2) ?III! to the desired .gamma.-chloro- or .gamma.-bromotiglic aldehyde I. The halogenating agent used in this process is selected from an alkali metal hypochlorite, an alkali metal hypobromite, an alkaline earth metal hypochlorite, an alkaline earth metal hypobromite, tert.butyl hypochlorite, N-bromoacetamide, 1.3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin. Further aspects of the present invention are the use of the thus-manufactured .gamma.Type: GrantFiled: August 1, 1997Date of Patent: July 28, 1998Assignee: Roche Vitamins Inc.Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
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Patent number: 5689011Abstract: The present invention provides a process for the production of glyoxals which comprises effecting the oxidative dehydrogenation of a glycol at a temperature of 400.degree. to 700.degree. C. in the presence of a silver-based catalyst composed of silver and at least one element selected from the group consisting of gold, platinum, rhodium and palladium, and phosphorus or a phosphorus compound, as well as such catalysts. These process and catalysts make it possible to produce high-quality glyoxals in high yield and with industrial advantages while minimizing the contents of unreacted raw material and reaction intermediates such as glycolaldehyde and acetol.Type: GrantFiled: May 18, 1995Date of Patent: November 18, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Kazuo Wakimura, Kazuhuyu Sudoh, Masao Tanaka, Hatuo Inoue, Nobuhisa Iwane
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Patent number: 5426239Abstract: Process for the continuous preparation of dimethoxy ethanal (DME) in which a 70% by weight of an aqueous solution of glyoxal is continuously reacted with 8 to 12 moles of methanol/mole of glyoxal in the presence of a cation exchange resin, then the reaction solution obtained is subjected to an initial distillation, at atmospheric pressure, in order to recover more than 90% of the unreacted methanol, which is recycled, then to a second distillation under a pressure of less than 10.+-.2 kPa in order to isolate an aqueous mixture containing the greater part of DME and 1,1,2,2-tetramethoxyethane (TME) formed. This mixture, after dilution with water (molar ratio of water/TME 29.+-.4), is subjected to a distillation under a pressure of less than 19 kPa in order to remove from the top fraction an aqueous mixture containing more than 98.5% of the TME present and to also obtain an aqueous solution of DME having a purity greater than 98.Type: GrantFiled: January 13, 1994Date of Patent: June 20, 1995Assignee: Societe Francaise HoechstInventors: Gilles Dressaire, Alain Schouteeten
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Patent number: 5426249Abstract: A process is described for the simultaneous production of 1,2- and 1,3-propanediol from glycerol. The process involves the reaction stages (a) dehydration of glycerol by feeding a gaseous glycerol-water mixture with 10 to 40 wt % glycerol at 250.degree. to 340.degree. C. over a solid catalyst with an H.sub.0 value (Hammett acidity function) of less than 2, preferably between -3 and -8.2, (b) hydration of the acrolein contained in the reaction mixture of stage (a), and (c) catalytic hydrogenation of the reaction mixture, containing 3-hydroxypropionaldehyde and hydroxyacetone, of stage (b). Two valuable products, namely 1,2- and 1,3-propanediol, can be obtained simultaneously and in high total yield from glycerol in a simple process.Type: GrantFiled: November 12, 1993Date of Patent: June 20, 1995Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Armin Neher, Dietrich Arntz, Herbert Klenk, Walter Girke
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Patent number: 5387720Abstract: A process for the production of acrolein by dehydration of glycerol in the liquid phase or in the gaseous phase, in each case on acidic solid catalysts, is described. Compared with previously known processes, the space-time yield and catalyst service life may be surprisingly increased with higher selectivity by treating a glycerol-water mixture with a glycerol content of 10 to 40 wt. % at 180.degree. to 340.degree. C. (liquid phase) or at 250.degree. to 340.degree. C. (gaseous phase) on a solid catalyst with an H.sub.o value (Hammett acidity function) of less than +2, preferably less than -3.Type: GrantFiled: November 12, 1993Date of Patent: February 7, 1995Assignee: Degussa AktiengesellschaftInventors: Armin Neher, Thomas Haas, Dietrich Arntz, Herbert Klenk, Walter Girke
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Patent number: 5367032Abstract: Epoxides are converted selectively to the corresponding carbonyl-containing compounds by reacting the epoxide with an oxidizing agent, typically hydrogen peroxide, in a liquid aqueous/organic two-phase system comprising:(a) an organic phase substantially containing the epoxide, and(b) an aqueous acidic phase substantially containing the oxidizing agent, in the presence of an onium compound capable of achieving phase partitioning and a catalytic system comprising a first catalyst component which is at least one element selected from tungsten, molybdenum, vanadium and chromium, or a compound containing at least one of the aforesaid elements, and a second catalyst component which is a phosphorus (V) acid or a species convertible to a phosphorus (V) acid.Type: GrantFiled: January 11, 1994Date of Patent: November 22, 1994Assignee: BP Chemicals LimitedInventors: David A. Hancock, David J. Moreton, Lee J. Morton
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Patent number: 5180855Abstract: A process for the preparation of citral by the cracking of prenal diprenyl acetal in a vapor phase in the presence of a heterogeneous type of acid catalyst.Type: GrantFiled: April 26, 1991Date of Patent: January 19, 1993Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Roland Jacquot, Claude Mercier
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Patent number: 5026922Abstract: There is disclosed a process for preparing glycol aldehyde from ethylene glycol by use of a complex system catalyst comprising copper and other inorganic component, which comprises permitting 0.001 to 0.3 mole of oxygen per one mole of ethylene glycol to be copresent in the reaction system.Type: GrantFiled: December 22, 1989Date of Patent: June 25, 1991Assignee: Research Association for Utilization of Light OilInventors: Takatoshi Seto, Takashi Yokoi, Masaki Odagiri, Makoto Imanari
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Patent number: 5004840Abstract: A novel process for the preparation of compounds of the formula ##STR1## with cis or trans structure in racemic or optically active form wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and aryl of 6 to 12 carbon atoms comprising reacting an optically active isomer, or racemate of the formula ##STR2## wherein R has the above definition and the way line indicates Z or E geometry with a gem-dimethyl cyclopropanation agent if there is Z geometry to obtain a compound of the formula ##STR3## or if the geometry is E with a gem-dimethyl cyclopropanation agent other than isopropylidene triphenyl phosphorane to obtain a compound of the formula ##STR4## wherein R has the above definition and the cyclopropane ring has the trans configuration and either hydrolyzing the compound of formula III or IIIa to obtain a compound of the formula ##STR5## and then cleaving the 4,5 bond to obtain the corresponding compound of formula I or simultaneously cleaving the 4,5 bond and hydrolyzing tType: GrantFiled: December 9, 1988Date of Patent: April 2, 1991Assignee: Roussel UclafInventors: Alain Krief, Willy Dumont