Polyoxy Containing Reactant Patents (Class 568/486)
  • Patent number: 8080692
    Abstract: The invention relates generally to the production of oxygenated hydrocarbons such as lower alcohols and more preferably 1,2-propanediol. More particularly, this invention comprises a single-step catalytic process for the catalytic production of lower alcohols such as methanol, ethanol, ethylene glycol and 1,2-propanediol from glycerol in aqueous medium. The catalyst comprises a metal selected from the Group VIII transition metals, preferably platinum, alloys thereof and mixtures thereof and a microporous carrier, preferably a faujasite-type zeolite.
    Type: Grant
    Filed: December 27, 2007
    Date of Patent: December 20, 2011
    Assignee: Katholieke Universiteit Leuven
    Inventors: Els D'Hondt, Pierre Jacobs, Bert Sels
  • Publication number: 20110288323
    Abstract: 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 on
    Type: Application
    Filed: December 16, 2009
    Publication date: November 24, 2011
    Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, ADISSEO FRANCE S.A.S
    Inventors: Virginie Belliere-Baca, Stephane Loridant, Jean-Marc Millet, Pascaline Lauriol-Garbey
  • Publication number: 20110275777
    Abstract: 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: Application
    Filed: November 3, 2009
    Publication date: November 10, 2011
    Inventors: Guido Stochniol, Goetz Baumgarten, Franz-Felix Kuppinger
  • Publication number: 20110237828
    Abstract: 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: Application
    Filed: August 20, 2008
    Publication date: September 29, 2011
    Applicant: SHOWA DENKO K.K.
    Inventors: Takanori Aoki, Norihide Arai
  • Publication number: 20110213174
    Abstract: 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: Application
    Filed: October 5, 2009
    Publication date: September 1, 2011
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Patent number: 7994368
    Abstract: 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: Grant
    Filed: September 16, 2010
    Date of Patent: August 9, 2011
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, James H. Zink, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, Jan Cornelis van der Waal, Virginie Zuzaniuk
  • Publication number: 20110160491
    Abstract: 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: Application
    Filed: April 14, 2009
    Publication date: June 30, 2011
    Applicant: Arkema France
    Inventors: Jean-Luc Dubois, Yasuhiro Magatani, Kimoto Okumura
  • Patent number: 7951978
    Abstract: 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: Grant
    Filed: November 28, 2007
    Date of Patent: May 31, 2011
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yoshitaka Arita, Hideaki Tsuneki, Hiroto Kasuga, Masaki Okada, Masaru Kirishiki
  • Publication number: 20110112330
    Abstract: 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: Application
    Filed: April 14, 2009
    Publication date: May 12, 2011
    Applicant: NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Yasuhiro Magatani, Kimito Okumura
  • Publication number: 20110087050
    Abstract: 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: Application
    Filed: June 4, 2009
    Publication date: April 14, 2011
    Applicant: SHOWA DENKO K.K.
    Inventors: Takanori Aoki, Masayuki Yoshimura
  • Publication number: 20110028760
    Abstract: 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: Application
    Filed: September 5, 2008
    Publication date: February 3, 2011
    Applicant: ARKEMA FRANCE
    Inventors: Jean-Luc Dubois, Grégory Patience
  • Patent number: 7872158
    Abstract: 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: Grant
    Filed: August 24, 2007
    Date of Patent: January 18, 2011
    Assignee: Battelle Memorial Institute
    Inventors: Thomas H. Peterson, Alan H. Zacher, Michel J. Gray, James F. White, Todd A. Werpy
  • Patent number: 7872159
    Abstract: 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: Grant
    Filed: August 24, 2007
    Date of Patent: January 18, 2011
    Assignee: Battelle Memorial Institute
    Inventors: Thomas H. Peterson, Alan H. Zacher, Michel J. Gray, James F. White, Todd A. Werpy
  • Patent number: 7847131
    Abstract: 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: Grant
    Filed: May 15, 2008
    Date of Patent: December 7, 2010
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yoshitaka Arita, Tsukasa Takahashi, Masaki Okada, Toshimitsu Moriguchi
  • Publication number: 20100280276
    Abstract: 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: Application
    Filed: June 11, 2008
    Publication date: November 4, 2010
    Applicant: SALTIGO GMBH
    Inventors: Thomas-Norbert Mueller, Michael Dockner
  • Publication number: 20100274038
    Abstract: 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: Application
    Filed: December 16, 2008
    Publication date: October 28, 2010
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Patent number: 7816565
    Abstract: 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: Grant
    Filed: July 31, 2008
    Date of Patent: October 19, 2010
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, James H. Zink, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, Jan Cornelis van der Waal, Virginie Zuzaniuk
  • Patent number: 7790934
    Abstract: A process for preparing acrolein from glycerol using an acidic solid-state catalyst which comprises tungsten compounds and further promoters.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: September 7, 2010
    Assignee: Evonik Degussa GmbH
    Inventors: Hubert Redlingshöfer, Christoph Weckbecker, Klaus Huthmacher, Andreas Dörflein
  • Publication number: 20100204502
    Abstract: 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: Application
    Filed: September 11, 2008
    Publication date: August 12, 2010
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Publication number: 20100168472
    Abstract: 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: Application
    Filed: November 20, 2009
    Publication date: July 1, 2010
    Inventors: Leonard Edward Bogan, JR., Mark Anthony Silvano
  • Patent number: 7737306
    Abstract: 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: Grant
    Filed: October 22, 2008
    Date of Patent: June 15, 2010
    Assignee: Suterra, LLC
    Inventors: Andrew Thompson, Shawn Zhang, Lonnie Robarge
  • Patent number: 7718829
    Abstract: 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: Grant
    Filed: May 11, 2007
    Date of Patent: May 18, 2010
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Okuno Masaaki, Matsunami Etsushige, Takahashi Tsukasa, Kasuga Hiroto, Okada Masaki, Kirishiki Masaru
  • Publication number: 20100113838
    Abstract: 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: Application
    Filed: May 15, 2008
    Publication date: May 6, 2010
    Applicant: NIPPON SHOKUBAI CO., LTD.
    Inventors: Yoshitaka Arita, Tsukasa Takahashi, Masaki Okada, Toshimitsu Moriguchi
  • Publication number: 20100113833
    Abstract: A process for preparing acrolein from glycerol using an acidic solid-state catalyst which comprises tungsten compounds and further promoters.
    Type: Application
    Filed: January 15, 2010
    Publication date: May 6, 2010
    Inventors: Hubert Redlingshöfer, Christoph Weckbecker, Klaus Huthmacher, Andreas Dörflein
  • Publication number: 20100105957
    Abstract: 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: Application
    Filed: November 28, 2007
    Publication date: April 29, 2010
    Inventors: Yoshitaka Arita, Hideaki Tsuneki, Hiroto Kasuka, Masaki Okada, Masaru Kirshiki
  • Patent number: 7683220
    Abstract: 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: Grant
    Filed: March 27, 2007
    Date of Patent: March 23, 2010
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Etsushige Matsunami, Tsukasa Takahashi, Hiroto Kasuga, Yoshitaka Arita
  • Patent number: 7655818
    Abstract: 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: Grant
    Filed: January 6, 2006
    Date of Patent: February 2, 2010
    Assignee: Arkema France
    Inventors: Jean-Luc Dubois, Christophe Duquenne, Wolfgang Holderich, Jacques Kervennal
  • Patent number: 7582799
    Abstract: 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: Grant
    Filed: April 27, 2006
    Date of Patent: September 1, 2009
    Assignees: Shiratori Pharmaceutical Co., Ltd., Asubio Pharma Co., Ltd.
    Inventors: Hiroshi Yoshino, Kentaro Kobayashi, Yuichi Shiro
  • Publication number: 20090177015
    Abstract: 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: Application
    Filed: May 11, 2007
    Publication date: July 9, 2009
    Inventors: Okuno Masaaki, Matsunami Etsushige, Takahashi Tsukasa, Kasuga Hiroto, Okada Masaki, Kirishiki Masaru
  • Publication number: 20090118549
    Abstract: 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: Application
    Filed: March 27, 2007
    Publication date: May 7, 2009
    Inventors: Etsushige Matsunami, Tsukasa Takahashi, Hiroto Kasuga, Yoshitaka Arita
  • Publication number: 20090076305
    Abstract: 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: Application
    Filed: April 27, 2006
    Publication date: March 19, 2009
    Applicants: Shiratori Pharmaceutical Co., Ltd., Asubio Pharma Co., Ltd.
    Inventors: Hiroshi Yoshino, Kentaro Kobayashi, Yuichi Shiro
  • Publication number: 20080319233
    Abstract: 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: Application
    Filed: February 6, 2007
    Publication date: December 25, 2008
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Publication number: 20080315151
    Abstract: A reactive-separation process converts glycerin into lower alcohols, having boiling points less than 200° C., at high yields. Conversion of natural glycerin to propylene glycol through an acetol intermediate is achieved at temperatures from 150° to 250° C. at pressures from 1 and 25 bar. The preferred applications of the propylene glycol are as an antifreeze, deicing compound, or anti-icing compound. The preferred catalyst for this process in a copper-chromium.
    Type: Application
    Filed: August 28, 2006
    Publication date: December 25, 2008
    Inventors: Galen J. Suppes, William Rusty Sutterlin
  • Patent number: 7396962
    Abstract: 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: Grant
    Filed: January 6, 2006
    Date of Patent: July 8, 2008
    Assignee: Arkema France
    Inventors: Jean-Luc Dubois, Christophe Duquenne, Wolfgang Holderich
  • Patent number: 7339085
    Abstract: 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: Grant
    Filed: February 4, 2005
    Date of Patent: March 4, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Klaus Henrich, Andreas Keller
  • Patent number: 7161030
    Abstract: 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: Grant
    Filed: July 31, 2003
    Date of Patent: January 9, 2007
    Assignee: Solvay Solexis S.p.A.
    Inventors: Rosaldo Picozzi, Antonella Di Meo, Claudio Tonelli
  • Patent number: 6864327
    Abstract: 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: Grant
    Filed: February 8, 2002
    Date of Patent: March 8, 2005
    Assignee: Nektar Therapeutics AL, Corporation
    Inventors: Michael David Bentley, J. Milton Harris, Antoni Kozlowski
  • Patent number: 6448369
    Abstract: 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: Grant
    Filed: November 5, 1998
    Date of Patent: September 10, 2002
    Assignee: Shearwater Corporation
    Inventors: Michael David Bentley, J. Milton Harris, Antoni Kozlowski
  • Patent number: 6376718
    Abstract: 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: Grant
    Filed: November 17, 2000
    Date of Patent: April 23, 2002
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Prakash Balan
  • Patent number: 6175044
    Abstract: 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: Grant
    Filed: September 24, 1999
    Date of Patent: January 16, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Jörg Therre, Gerd Kaibel, Werner Aquila, G{umlaut over (u)}nter Wegner, Hartwig Fuchs
  • Patent number: 6080898
    Abstract: 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: Grant
    Filed: July 23, 1998
    Date of Patent: June 27, 2000
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Willem Wabe Jager
  • Patent number: 5786518
    Abstract: 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: Grant
    Filed: August 1, 1997
    Date of Patent: July 28, 1998
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, Paul Nosberger, August Ruttimann
  • Patent number: 5689011
    Abstract: 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: Grant
    Filed: May 18, 1995
    Date of Patent: November 18, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kazuo Wakimura, Kazuhuyu Sudoh, Masao Tanaka, Hatuo Inoue, Nobuhisa Iwane
  • Patent number: 5426239
    Abstract: 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: Grant
    Filed: January 13, 1994
    Date of Patent: June 20, 1995
    Assignee: Societe Francaise Hoechst
    Inventors: Gilles Dressaire, Alain Schouteeten
  • Patent number: 5426249
    Abstract: 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: Grant
    Filed: November 12, 1993
    Date of Patent: June 20, 1995
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Armin Neher, Dietrich Arntz, Herbert Klenk, Walter Girke
  • Patent number: 5387720
    Abstract: 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: Grant
    Filed: November 12, 1993
    Date of Patent: February 7, 1995
    Assignee: Degussa Aktiengesellschaft
    Inventors: Armin Neher, Thomas Haas, Dietrich Arntz, Herbert Klenk, Walter Girke
  • Patent number: 5367032
    Abstract: 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: Grant
    Filed: January 11, 1994
    Date of Patent: November 22, 1994
    Assignee: BP Chemicals Limited
    Inventors: David A. Hancock, David J. Moreton, Lee J. Morton
  • Patent number: 5180855
    Abstract: 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: Grant
    Filed: April 26, 1991
    Date of Patent: January 19, 1993
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Roland Jacquot, Claude Mercier
  • Patent number: 5026922
    Abstract: 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: Grant
    Filed: December 22, 1989
    Date of Patent: June 25, 1991
    Assignee: Research Association for Utilization of Light Oil
    Inventors: Takatoshi Seto, Takashi Yokoi, Masaki Odagiri, Makoto Imanari
  • Patent number: 5004840
    Abstract: 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 t
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: April 2, 1991
    Assignee: Roussel Uclaf
    Inventors: Alain Krief, Willy Dumont