Preparing From Compound Containing -coo- Group Patents (Class 549/508)
  • Patent number: 10434504
    Abstract: A method for the reduction organic molecules comprising a Ruthenium-Triphosphine complex with aromatic ligands at the phosphors which are ortho or meta substituted.
    Type: Grant
    Filed: November 27, 2018
    Date of Patent: October 8, 2019
    Assignee: RHEINISCH-WESTFÄLISCHE TECHNISCHE HOCHSCHULE (RWTH) AACHEN
    Inventors: Jürgen Klankermayer, Walter Leitner, Markus Meuresch
  • Patent number: 10166534
    Abstract: A method for the reduction organic molecules comprising a Ruthenium-Triphosphine complex with aromatic ligands at the phosphors which are ortho or meta substituted.
    Type: Grant
    Filed: February 11, 2015
    Date of Patent: January 1, 2019
    Assignee: RHEINISCH-WESTFALISCHE TECHNISCHE HOCHSCHULE (RWTH) AACHEN
    Inventors: Jürgen Klankermayer, Walter Leitner, Markus Meuresch
  • Patent number: 9834491
    Abstract: The present invention relates to a method of producing bio-based homoserine lactone and bio-based organic acid through hydrolysis of O-acyl homoserine produced by a microorganism in the presence of an acid catalyst. According to the present invention, O-acyl homoserine produced by a microorganism is used as a raw material for producing 1,4-butanediol, gamma-butyrolactone, tetrahydrofuran and the like, which are industrially highly useful. The O-acyl homoserine produced by a microorganism can substitute conventional petrochemical products, can solve environmental concerns, including the emission of pollutants and the exhaustion of natural resources, and can be continuously renewable so as not to exhaust natural resources.
    Type: Grant
    Filed: March 19, 2014
    Date of Patent: December 5, 2017
    Assignee: CJ CHEILJEDANG CORPORATION
    Inventors: Han Won Lee, Young Lyeol Yang, So Young Kim, Yong Uk Shin, Jin Sook Chang, Hye Won Um, Young Hyoung Goh, Sung Hoo Jhon
  • Patent number: 9487460
    Abstract: Disclosed are a method of preparing allyl alcohol and allyl alcohol prepared thereby. The method of preparing allyl alcohol includes adding glycerol with formic acid in an amount of 0.8˜2 equivalents relative to 1 equivalent of glycerol, and increasing a reaction temperature to 220˜260° C. from room temperature at a heating rate of 2.0˜7.0° C./min so that glycerol and formic acid are reacted.
    Type: Grant
    Filed: June 27, 2014
    Date of Patent: November 8, 2016
    Assignee: LG Chem, Ltd.
    Inventors: Won Jae Lee, Myungjin Kong, Yong-Jin Choe, Hyun Nam
  • Patent number: 9040756
    Abstract: A process for the production of 1,4-butanediol and tetrahydrofuran by catalytic hydrogenation of dialkyl maleates includes the following steps: a) hydrogenating a stream of dialkyl maleate in a first stage of reaction over suitable catalysts to produce dialkyl succinate; b) further hydrogenating the dialkyl succinate in a second stage of reaction, by using a different suitable catalyst, for producing mainly 1,4-butanediol, together with gamma-butyrolactone and tetrahydrofuran as co-products. In both stages of reaction the conditions, as hydrogen/organic feed ratio, pressure and temperature, are such to maintain the reactors in mixed liquid/vapor phase.
    Type: Grant
    Filed: November 25, 2011
    Date of Patent: May 26, 2015
    Assignee: CONSER SPA
    Inventors: Flavio Simola, Marco Scarsella, Paolo De Filippis
  • Publication number: 20140316146
    Abstract: A process for the production of 1,4-butanediol and tetrahydrofuran by catalytic hydrogenation of dialkyl maleates includes the following steps: a) hydrogenating a stream of dialkyl maleate in a first stage of reaction over suitable catalysts to produce dialkyl succinate; b) further hydrogenating the dialkyl succinate in a second stage of reaction, by using a different suitable catalyst, for producing mainly 1,4-butanediol, together with gamma-butyrolactone and tetrahydrofuran as co-products. In both stages of reaction the conditions, as hydrogen/organic feed ratio, pressure and temperature, are such to maintain the reactors in mixed liquid/vapor phase.
    Type: Application
    Filed: November 25, 2011
    Publication date: October 23, 2014
    Applicant: CONSER SPA
    Inventors: Flavio Simola, Marco Scarsella, Paolo De Filippis
  • Publication number: 20140296466
    Abstract: The present invention relates to a method of producing bio-based homoserine lactone and bio-based organic acid through hydrolysis of O-acyl homoserine produced by a microorganism in the presence of an acid catalyst. According to the present invention, O-acyl homoserine produced by a microorganism is used as a raw material for producing 1,4-butanediol, gamma-butyrolactone, tetrahydrofuran and the like, which are industrially highly useful. The O-acyl homoserine produced by a microorganism can substitute conventional petrochemical products, can solve environmental concerns, including the emission of pollutants and the exhaustion of natural resources, and can be continuously renewable so as not to exhaust natural resources.
    Type: Application
    Filed: March 19, 2014
    Publication date: October 2, 2014
    Inventors: Han Won Lee, Young Lyeol Yang, So Young Kim, Yong Uk Shin, Jin Sook Chang, Hye Won Um, Young Hyoung Goh, Sung Hoo Jhon
  • Patent number: 8816104
    Abstract: A process for activating a reduced manganese copper catalyst comprising treating the catalyst at a temperature of more than 300° C. to about 400° C. with hydrogen.
    Type: Grant
    Filed: February 20, 2009
    Date of Patent: August 26, 2014
    Assignee: Davy Process Technology Limited
    Inventors: Michael Anthony Wood, Paul Willett, Paul Appleton
  • Patent number: 8598372
    Abstract: The present invention relates to a method for producing a cyclic compound that has high selectivity, high yield, and stability over a long period of time depending on a metal content ratio of a catalyst, specifically a lactone compound or a heterocyclic compound including oxygen, which includes hydrogenating an organic acid, organic acid ester, or a mixture of the organic acid and organic acid ester, which are having 4 to 6 carbon atoms, by using a selective hydrogenated catalyst.
    Type: Grant
    Filed: August 27, 2010
    Date of Patent: December 3, 2013
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Young Kyu Hwang, Jong San Chang, Jung Ho Lee, Jong-Min Lee
  • Patent number: 8536351
    Abstract: Cyclohexanedione compounds of Formula (I) wherein R1 is methyl, ethyl, n-propyl, iso-propyl, cyclopropyl, halomethyl, haloethyl, halogen, vinyl, ethynyl, methoxy, ethoxy, halomethoxy or haloethoxy, R2 and R3 are, independently hydrogen, halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C3-C6alkenyloxy, C3-C6haloalkenyloxy, C3-C6alkynyloxy, C3-C6cycloalkyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6alkylsulfonyloxy, C1-C6haloalkylsulfonyloxy, cyano, nitro, phenyl, phenyl substituted by C1-C4alkyl, C1-C3Cahaloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, cyano, nitro, halogen, C1-C3alkylthio, C1-C3alkylsulfinyl or C1-C3alkylsulfonyl, or heteroaryl or heteroaryl substituted by C1-C3Calkyl, d.
    Type: Grant
    Filed: March 7, 2008
    Date of Patent: September 17, 2013
    Assignee: Syngenta Crop Protection LLC
    Inventors: Christopher John Mathews, John Finney, Louisa Robinson, Melloney Tyte, Michel Muehlebach, Jean Wenger
  • Patent number: 8466300
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth; distilling the broth under super atmospheric pressure at a temperature of >100° C. to about 300° C. to form an overhead that includes water and ammonia, and a liquid bottoms that includes SA, and at least about 20 wt % water; cooling the bottoms to a temperature sufficient to cause the bottoms to separate into a liquid portion in contact with a solid portion that is substantially pure SA; separating the solid portion from the liquid portion; recovering the solid portion; hydrogenating the solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product including at least one of THF, GBL or BDO; and recovering the hydrogenated product.
    Type: Grant
    Filed: March 18, 2011
    Date of Patent: June 18, 2013
    Assignee: BioAmber International S.a.r.l.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
  • Patent number: 8399687
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.
    Type: Grant
    Filed: December 22, 2011
    Date of Patent: March 19, 2013
    Assignee: BioAmber International S.a.r.l.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
  • Publication number: 20130046075
    Abstract: A double-walled plastic jar for cosmetic materials, having an inner compartment to hold the cosmetic, and an annular outer side wall defining the exterior of the jar. The inner compartment carries the lip that seals with a screw cap, and also carries an external skirt, which latter has the screw threads for engagement by the cap. In addition, a weight is disposed in a-concealed manner in the base of the jar, between the walls, to give the jar a heft feel, characteristic of glass or thick plastic walls.
    Type: Application
    Filed: April 4, 2011
    Publication date: February 21, 2013
    Inventors: Johan van Walsem, Erik Anderson, John Licata, Kevin A. Sparks, William R. Farmer, Christopher Mirley, Jeffrey A. Bickmeier, Ann D'Ambruoso, Frank A. Skraly, Thomas M. Ramseier, M.S. Sivasubramanian, Yossef Shabtai
  • Publication number: 20120215014
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.
    Type: Application
    Filed: April 27, 2012
    Publication date: August 23, 2012
    Applicant: BioAmber International S.a.r.l.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
  • Publication number: 20120197029
    Abstract: The present invention relates to a method for producing a cyclic compound that has high selectivity, high yield, and stability over a long period of time depending on a metal content ratio of a catalyst, specifically a lactone compound or a heterocyclic compound including oxygen, which includes hydrogenating an organic acid, organic acid ester, or a mixture of the organic acid and organic acid ester, which are having 4 to 6 carbon atoms, by using a selective hydrogenated catalyst.
    Type: Application
    Filed: August 27, 2010
    Publication date: August 2, 2012
    Applicant: Korea Research Institute of Chemical Technology
    Inventors: Young Kyu Hwang, Jong San Chang, Jung Ho Lee, Jong-Min Lee
  • Patent number: 8193375
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.
    Type: Grant
    Filed: August 19, 2011
    Date of Patent: June 5, 2012
    Assignee: BioAmber International S.ä.r.l.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
  • Publication number: 20120095241
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.
    Type: Application
    Filed: December 22, 2011
    Publication date: April 19, 2012
    Applicant: BioAmber International S.a.r.l.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
  • Publication number: 20120015411
    Abstract: The present application relates to a process for manufacturing maleic anhydride that comprising the following steps: a) fermentation of renewable raw materials and optionally purification to produce a mixture comprising at least butanol; b) oxidation of the butanol to maleic anhydride at a temperature generally between 300° C. to 600° C., using a catalyst based on oxides of vanadium and/or molybdenum; c) isolation of the maleic anhydride obtained at the end of step b). It also relates to the maleic anhydride obtained from renewable raw materials, to the copolymers and compositions comprising said maleic anhydride and also uses of use of this maleic anhydride.
    Type: Application
    Filed: July 17, 2009
    Publication date: January 19, 2012
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Patent number: 8084626
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth; distilling the broth under super atmospheric pressure at a temperature of >100° C. to about 300° C. to form an overhead that includes water and ammonia, and a liquid bottoms that includes SA, and at least about 20 wt % water; cooling the bottoms to a temperature sufficient to cause the bottoms to separate into a liquid portion in contact with a solid portion that is substantially pure SA; separating the solid portion from the liquid portion; recovering the solid portion; hydrogenating the solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product including at least one of THF, GBL or BDO; and recovering the hydrogenated product.
    Type: Grant
    Filed: August 19, 2011
    Date of Patent: December 27, 2011
    Assignee: BioAmber S.A.S.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
  • Publication number: 20110306777
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth; distilling the broth under super atmospheric pressure at a temperature of >100° C. to about 300° C. to form an overhead that includes water and ammonia, and a liquid bottoms that includes SA, and at least about 20 wt % water; cooling the bottoms to a temperature sufficient to cause the bottoms to separate into a liquid portion in contact with a solid portion that is substantially pure SA; separating the solid portion from the liquid portion; recovering the solid portion; hydrogenating the solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product including at least one of THF, GBL or BDO; and recovering the hydrogenated product.
    Type: Application
    Filed: August 19, 2011
    Publication date: December 15, 2011
    Applicant: BioAmber S.A.S.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
  • Publication number: 20110301364
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.
    Type: Application
    Filed: August 19, 2011
    Publication date: December 8, 2011
    Applicant: BioAmber S.A.S.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
  • Publication number: 20110245514
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth; distilling the broth under super atmospheric pressure at a temperature of >100° C. to about 300° C. to form an overhead that includes water and ammonia, and a liquid bottoms that includes SA, and at least about 20 wt % water; cooling the bottoms to a temperature sufficient to cause the bottoms to separate into a liquid portion in contact with a solid portion that is substantially pure SA; separating the solid portion from the liquid portion; recovering the solid portion; hydrogenating the solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product including at least one of THF, GBL or BDO; and recovering the hydrogenated product.
    Type: Application
    Filed: March 18, 2011
    Publication date: October 6, 2011
    Applicant: BIOAMBER S.A.S.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
  • Publication number: 20110245517
    Abstract: The present invention relates to a process for preparing tetrahydrofuran by absorption of C4-dicarboxylic acids and/or derivatives thereof from a crude product mixture into an organic solvent or water as absorption medium, removal of the absorption medium, catalytic hydrogenation of the resulting C4-dicarboxylic acids and/or derivatives thereof and distillation of the water-comprising crude tetrahydrofuran in at least one distillation column, wherein THF-comprising waste streams from the distillation are catalytically hydrogenated with complete or partial recirculation to the process.
    Type: Application
    Filed: November 5, 2009
    Publication date: October 6, 2011
    Applicant: BASF SE
    Inventors: Gunther Windecker, Jens Weiguny, Alexander Weck, Ellen Dahlhoff, Ralf Freyberger
  • Publication number: 20110245515
    Abstract: A process for making a hydrogenated product includes providing a clarified DAS-containing fermentation broth, distilling the broth to form an overhead that includes water and ammonia, and a liquid bottoms that includes MAS, at least some DAS, and at least about 20 wt % water, cooling and/or evaporating the bottoms, and optionally adding an antisolvent to the bottoms, to attain a temperature and composition sufficient to cause the bottoms to separate into a DAS-containing liquid portion and a MAS-containing solid portion that is substantially free of DAS, separating the solid portion from the liquid portion, recovering the solid portion, hydrogenating the second solid portion in the presence of at least one hydrogenation catalyst to produce the hydrogenated product comprising at least one of THF, GBL or BDO, and recovering the hydrogenated product.
    Type: Application
    Filed: March 18, 2011
    Publication date: October 6, 2011
    Applicant: BIOAMBER S.A.S.
    Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian Terry Keen, Brooke Ashley Albin, Nye A. Clinton, Bernard Duane Dombek
  • Patent number: 7935834
    Abstract: This invention relates to a process for catalytically hydrogenating a hydrogenatable precursor in contact with a hydrogen-containing gas and a hydrogenation catalyst comprising one or more active hydrogenation catalyst components on a support comprising titanium dioxide in the rutile crystalline phase to produce 1,4-butanediol and, optionally, gamma-butyrolactone and/or tetrahydrofuran.
    Type: Grant
    Filed: July 1, 2004
    Date of Patent: May 3, 2011
    Assignee: ISP Investments Inc.
    Inventors: Alakananda Bhattacharyya, Maynard D. Manila
  • Publication number: 20110092721
    Abstract: A process for activating a reduced manganese copper catalyst comprising treating the catalyst at a temperature of more than 300° C. to about 400° C. with hydrogen.
    Type: Application
    Filed: February 20, 2009
    Publication date: April 21, 2011
    Applicant: DAVY PROCESS TECHNOLOGY LIMITED
    Inventors: Michael Anthony Wood, Paul Willett, Paul Appleton
  • Patent number: 7902386
    Abstract: The present invention provides a process for depolymerizing mixtures comprising mono- and/or diesters of polytetrahydrofuran in the presence of an acidic catalyst and of a C1- to C3-alcohol at temperatures of from 80 to 200° C. and a pressure of from 0.05 to 0.5 MPa, where the molar ratio of the C1- to C3-alcohol relative to the carboxyl groups present in the mixture is greater than 1.
    Type: Grant
    Filed: August 27, 2008
    Date of Patent: March 8, 2011
    Assignee: BASF SE
    Inventors: Tobias Wabnitz, Ricardo Ferre Gimenez, Robert Laubner, Ralf Stolle
  • Publication number: 20090287004
    Abstract: A method of preparing an olefin comprising: reacting a polyol in the presence of a carboxylic acid, such that an olefin is produced by the deoxygenation of the polyol. The reacting step can comprise (a) providing a composition comprising the polyol, (b) heating the composition, and (c) introducing the carboxylic acid to the composition wherein the introducing step occurs prior to, at the same time as, or subsequent to the heating step. In one embodiment, the polyol is glycerol, the carboxylic acid is formic acid, and the olefin is allyl alcohol, which is produced at a yield of about 80% or greater.
    Type: Application
    Filed: July 27, 2009
    Publication date: November 19, 2009
    Applicant: The Regents of the University of California
    Inventors: Robert G. Bergman, Jonathan A. Ellman, Elena Arceo Rebollo, Peter C. Marsden
  • Patent number: 7598404
    Abstract: A process for the production of an ether optionally with a diol and/or a lactone, by reaction of a corresponding organic feed material selected from unsaturated dicarboxylic acids and/or anhydrides, mono-esters of unsaturated dicarboxylic acids and/or anhydrides, diesters of unsaturated dicarboxylic acids and/or anhydrides, unsaturated lactones, and mixtures of two or more thereof in the presence of hydrogen which comprises the steps of-(a) supplying a stream comprising at least a portion of the organic feed material to a pre-reactor zone comprising catalyst and operating under reaction conditions and contacting said feed with a hydrogen containing stream such that at least some of the carbon carbon double bonds are saturated; (b) vaporising the at least partly saturated feed into the hydrogen containing stream in a vaporizing zone; (c) supplying the hydrogen-containing stream containing the vaporized at least partially saturated feed to a reaction zone comprising catalyst and operating under reaction conditi
    Type: Grant
    Filed: December 1, 2004
    Date of Patent: October 6, 2009
    Assignee: Davy Process Technology Limited
    Inventors: Adrian Francis Backes, Andrew George Hiles, David Mark Sutton
  • Patent number: 7214641
    Abstract: The present invention provides a process for hydrogenating carbonyl compounds, in particular C4-dicarboxylic acids to mixtures of tetrahydrofuran and gamma-butyrolactone, over supported rhenium catalysts, wherein rhenium and at least one further metal of groups VIII or Ib of the Periodic Table of the Elements, in particular ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), platinum (Pt), copper (Cu), silver (Ag) or cobalt (Co), is applied to the support in the form of at least one bimetallic precursor compound, and also to these catalysts.
    Type: Grant
    Filed: November 6, 2003
    Date of Patent: May 8, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Markus Schubert, Michael Hesse, Rolf-Hartmuth Fischer, Take Constantinescu
  • Patent number: 7193091
    Abstract: A process for coproducing alkyl-substituted or unsubstituted THF and pyrrolidones by catalytically hydrogenating C4-dicarboxylic acids and/or derivatives thereof in the gas phase in the presence of copper catalysts and reacting GBL with ammonia or primary amines to give pyrrolidones.
    Type: Grant
    Filed: February 28, 2003
    Date of Patent: March 20, 2007
    Assignee: Basf Aktiengesellschaft
    Inventors: Rolf-Hartmuth Fischer, Markus Rösch, Nils Bottke, Alexander Weck, Gunther Windecker, Michael Hesse, Holger Borchert, Stephan Schlitter
  • Patent number: 6989455
    Abstract: In the process for the conversion of maleic acid to gamma-butyrolactone, 1.4-butanediol and/or tetrahydrofuran, a feedstream comprising maleic acid is hydrogenated in a first hydrogenation zone to produce a reaction product comprising succinic acid and unreacted hydrogen which is then supplied to a second hydrogenation zone, where succinic acid is converted to 1,4-butanediol, the temperatures of the feedstream comprising maleic acid and the first hydrogenation zone are controlled such that the temperature of maleic acid in the feedstream and the first hydrogenation zone does not exceed about 130° C., thereby minimizing the corrosive effects of the maleic acid and prolonging reactor life and improving overall process economics.
    Type: Grant
    Filed: August 21, 2003
    Date of Patent: January 24, 2006
    Assignee: ISP Investments Inc.
    Inventors: Robert P. Hepfer, Craig T. Miller, Gregory A. Norenberg, Thomas G. Attig, John R. Budge
  • Patent number: 6958404
    Abstract: C4-dicarboxylic acids or derivatives thereof are hydrogenated in the gas phase in a fluidized-bed reactor. It is possible to use catalyst compositions known per se.
    Type: Grant
    Filed: December 7, 2001
    Date of Patent: October 25, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Holger Borchert, Stephan Schlitter, Michael Hesse, Frank Stein, Rolf-Hartmuth Fischer, Ralf-Thomas Rahn, Alexander Weck, Markus Rösch
  • Patent number: 6936727
    Abstract: A process is described for the production of ethers, typically terahydrofuran, by reaction of a corresponding organic feed material selected from dicarboxylic acids and/or anhydrides, monoesters of dicarboxylic acids and/or anhydrides, diesters of dicarboxylic acids and/or anhydrides, lactones, and mixtures of two or more thereof in the presence of hydrogen which comprises the steps of: (a) supplying a stream comprising the organic feed material to a first vaporisation zone and contacting said feed with cycle gas comprising hydrogen such that at least a portion of the feed material is vaporised by and into the cycle gas; (b) supplying at least a portion of the cycle gas and the vaporised feed material to a first reaction zone comprising catalyst and operating under reaction conditions to allow hydrogenation and dehydration to occur; (c) recovering from the first reaction zone an intermediate product stream comprising unreacted feed material, cycle gas, desired product(s), and any co-products and by-products;
    Type: Grant
    Filed: July 10, 2002
    Date of Patent: August 30, 2005
    Assignee: Davy Process Technology Limited
    Inventors: David Mark Sutton, Andrew George Hiles, Graham Reed, John Anthony Stannard
  • Patent number: 6888011
    Abstract: A hydrogenation catalyst which is suitable, in particular, for the hydrogenation of maleic anhydride and its derivatives to THF or its derivatives comprises copper oxide and at least one further metal or compound thereof, preferably an oxide, selected from the group consisting of Al, Si, Zn, La, Ce, the elements of groups IIIA to VIIIA and the elements of groups IA and IIA and having a pore volume of ?0.01 ml/g for pore diameters of >50 nm and a ratio of the pore volume of macropores having a diameter of >50 nm to the total pore volume for pores having a diameter of >4 nm of >10%.
    Type: Grant
    Filed: December 7, 2001
    Date of Patent: May 3, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Holger Borchert, Stephan Schlitter, Markus Rösch, Rolf-Hartmuth Fischer, Ralf-Thomas Rahn, Alexander Weck
  • Patent number: 6844452
    Abstract: A process for the co-production of a diol product (e.g. butane-1,4-diol) and a cyclic ether (e.g. tetrahydrofuran) by hydrogenation of an aliphatic diester or lactone feedstock (e.g. dimethyl or diethyl maleate), which contains a minor amount of acidic material, such as the corresponding monoester. The process utilizes a plurality of hydrogenation zones connected in series, each containing a charge of a granular ester hydrogenation catalyst. The catalyst in the first hydrogenation zone is tolerant of a minor amount of acidic material, while the catalyst in the second hydrogenation zone provides enhanced yields of cyclic ethers compared to the catalyst of the first hydrogenation zone. The catalyst in a third hydrogenation zone exhibits low selectivity towards conversion of the diester to at least one by product (e.g. 2-4?-hydroxybutoxy-tetrahydrofuran).
    Type: Grant
    Filed: December 12, 2000
    Date of Patent: January 18, 2005
    Assignee: Davy Process Technology Ltd.
    Inventors: Michael Anthony Wood, Paul Willett, Robert Wild, Stephen William Colley
  • Patent number: 6831182
    Abstract: The present invention relates to a process for the gas-phase hydrogenation of C4-dicarboxylic acids and/or their derivatives over a catalyst based on copper oxide to give substituted or unsubstituted &ggr;-butyrolactone and/or tetrahydrofuran, which comprises, which a first reaction zone in which the C4-dicarboxylic acid and/or its derivatives is/are reacted to give a mixture comprising a substituted or unsubstituted &ggr;-butyrolactone as main product and a subsequent second reaction zone in which the substituted or unsubstituted &ggr;-butyrolactone present in the mixture from the first hydrogenation step is reacted at a temperature lower than the temperature in the first hydrogenation step to give substituted or unsubstituted tetrahydrofuran.
    Type: Grant
    Filed: June 4, 2003
    Date of Patent: December 14, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Holger Borchert, Stephan Schlitter, Rolf-Hartmuth Fischer, Markus Rösch, Frank Stein, Ralf-Thomas Rahn, Alexander Weck, Gerd Kaibel
  • Patent number: 6756501
    Abstract: Disclosed is a single step continuous hydrogenation process for the preparation of 3-methyl-tetrahydrofuran from alpha-methylene-gamma-butyrolactone, in the presence of a catalytic metal.
    Type: Grant
    Filed: July 9, 2002
    Date of Patent: June 29, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6730800
    Abstract: Unsubstituted or alkyl-substituted THF is obtained by catalytic hydrogenation in the gas phase of C4-dicarboxylic acids and/or their derivatives using a catalyst comprising <80% by weight, preferably <70% by weight, in particular from 10 to 65% by weight, of CuO and >20% by weight, preferably >30% by weight, in particular from 35 to 90% by weight, of an oxidic support having acid centers, at a hot spot temperature of from 240 to 310° C., preferably from 240 to 280° C., and a WHSV over the catalyst of from 0.01 to 1.0, preferably from 0.02 to 1, in particular from 0.05 to 0.5, kg of starting material/l of catalyst x hour.
    Type: Grant
    Filed: June 4, 2003
    Date of Patent: May 4, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf-Hartmuth Fischer, Frank Stein, Rolf Pinkos, Michael Hesse, Michael Jolyon Sprague, Markus Rösch, Holger Borchert, Stephan Schlitter, Ralf-Thomas Rahn, Alexander Weck
  • Patent number: 6700003
    Abstract: A method for producing a saturated cyclic ether from a fatty acid ester of an &agr;, &dgr;-diol stably in high yield over a long period of time, is presented. It is a process for producing a saturated cyclic ether, which comprises reacting a mono- and/or di-fatty acid ester of an &agr;, &dgr;-diol in the presence of a solid acid catalyst, wherein the reaction is carried out in such a state that at least 50 mol % of the fatty acid ester supplied to the reaction system is vaporized.
    Type: Grant
    Filed: December 12, 2002
    Date of Patent: March 2, 2004
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Kazuhiko Kiyooka, Toshiharu Yokoyama
  • Publication number: 20040039214
    Abstract: Unsubstituted or alkyl-substituted THF is obtained by catalytic hydrogenation in the gas phase of C4-dicarboxylic acids and/or their derivatives using a catalyst comprising <80% by weight, preferably <70% by weight, in particular from 10 to 65% by weight, of CuO and >20% by weight, preferably >30% by weight, in particular from 35 to 90% by weight, of an oxidic support having acid centers, at a hot spot temperature of from 240 to 310° C., preferably from 240 to 280° C., and a WHSV over the catalyst of from 0.01 to 1.0, preferably from 0.02 to 1, in particular from 0.05 to 0.5, kg of starting material/l of catalyst×hour.
    Type: Application
    Filed: June 4, 2003
    Publication date: February 26, 2004
    Inventors: Rolf-Hartmuth Fischer, Frank Stein, Rolf Pinkos, Michael Hesse, Michael Jolyon Sprague, Markus Rosch, Holger Borchert, Stephan Schlitter, Ralf-Thomas Rahn, Alexander Weck
  • Publication number: 20040034240
    Abstract: The present invention relates to a process for the gas-phase hydrogenation of C4-dicarboxylic acids and/or their derivatives over a catalyst based on copper oxide to give substituted or unsubstituted &ggr;-butyrolactone and/or tetrahydrofuran, which comprises, which a first reaction zone in which the C4-dicarboxylic acid and/or its derivatives is/are reacted to give a mixture comprising a substituted or unsubstituted &ggr;-butyrolactone as main product and a subsequent second reaction zone in which the substituted or unsubstituted &ggr;-butyrolactone present in the mixture from the first hydrogenation step is reacted at a temperature lower than the temperature in the first hydrogenation step to give substituted or unsubstituted tetrahydrofuran.
    Type: Application
    Filed: June 4, 2003
    Publication date: February 19, 2004
    Inventors: Holger Borchert, Stephan Schlitter, Rolf-Hartmuth Fischer, Markus Rosch, Frank Stein, Ralf-Thomas Rahn, Alexander Weck, Gerd Kaibel
  • Publication number: 20040030163
    Abstract: A hydrogenation catalyst which is suitable, in particular, for the hydrogenation of maleic anhydride and its derivatives to THF or its derivatives comprises copper oxide and at least one further metal or compound thereof, preferably an oxide, selected from the group consisting of Al, Si, Zn, La, Ce, the elements of groups IIIA to VIIIA and the elements of groups IA and IIA and having a pore volume of ≧ 0.01 ml/g for pore diameters of >50 nm and a ratio of the pore volume of macropores having a diameter of >50 nm to the total pore volume for pores having a diameter of >4 nm of >10%.
    Type: Application
    Filed: May 29, 2003
    Publication date: February 12, 2004
    Inventors: Holger Borchert, Stephan Sclitter, Markus Rosch, Rolf-Hartmuth Fischer, Ralf-Thomas Rahn, Alexander Weck
  • Patent number: 6673946
    Abstract: Disclosed is a hydrogenation process for the preparation of 3-methyl-tetrahydrofuran from 2-methyl-gamma-butyrolactone. The above process enables the production of the objective highly pure 3-methyl-tetrahydrofuran free from alcohol in high efficiency and high conversion through a simple production step.
    Type: Grant
    Filed: July 9, 2002
    Date of Patent: January 6, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Patent number: 6670300
    Abstract: A textured catalyst having a hydrothermally-stable support, a metal oxide and a catalyst component is described. Methods of conducting aqueous phase reactions that are catalyzed by a textured catalyst are also described. The invention also provides methods of making textured catalysts and methods of making chemical products using a textured catalyst.
    Type: Grant
    Filed: June 18, 2001
    Date of Patent: December 30, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
  • Patent number: 6670490
    Abstract: An improved catalyst of platinum, rhenium and tin with an inert support used for hydrogenation of an hydrogenatable precursor in an aqueous solution and a method for using the catalyst in the production of tetrahydrofuran and 1,4-butanediol from such a hydrogenatable precursor in an aqueous solution.
    Type: Grant
    Filed: December 23, 2002
    Date of Patent: December 30, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Daniel Campos, Gregg Mason Sisler
  • Patent number: 6664402
    Abstract: Disclosed is a two-step, continuous hydrogenation process for the preparation of 3-methyl-tetrahydrofuran from alpha-methylene-gamma-butyrolactone, which comprises a first step of subjecting alpha-methylene-gamma-butyrolactone to hydrogenation to synthesize 2-methyl-gamma-butyrolactone; and the second step of hydrogenating the 2-methyl-gamma-butyrolactone formed in the first step. The above process enables the production of the objective highly-pure 3-methyl-tetrahydrofuran free from alcohol in high efficiency and high conversion through simple production steps.
    Type: Grant
    Filed: July 9, 2002
    Date of Patent: December 16, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Leo Ernest Manzer
  • Publication number: 20030186395
    Abstract: The present invention relates to a process for the systhesis of optically enriched dextro- and laevo-rotatory isomers of rose oxide from racemic citronellol. The invention particularly relates to the preparation of optically enriched (−)-(2 S, 4 R)-rose oxide and its isomer (+)-(2 R, 4 S)-rose oxide torn racemic citronellol.
    Type: Application
    Filed: March 29, 2002
    Publication date: October 2, 2003
    Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
    Inventors: Shubhash Chandra Taneja, Vijay Kumar Sethi, Surrinder Koul, Samar Singh Andotra, Ghulam Nabi Qazi
  • Patent number: 6620949
    Abstract: A process is described for the co-production of maleic anhydride and at least one C4 compound selected from butane-1,4-diol, &ggr;-butyrolactone, and tetrahydrofuran in which maleic anhydride is produced by partial oxidation of a hydrocarbon feedstock selected from C4 hydrocarbons and benzene to yield a vaporous reaction effluent stream comprising maleic anhydride, water, unconverted hydrocarbon feedstock, and carbon oxides. A part of the maleic anhydride present in the vaporous reaction effluent stream is condensed to form a crude maleic anhydride stream and leave a residual vaporous stream containing residual amounts of maleic anhydride. Further maleic anhydride is absorbed from the residual vaporous stream by absorption in an organic solvent, water or an aqueous solution. Maleic anhydride is then recovered from the loaded liquid absorptions medium.
    Type: Grant
    Filed: July 22, 2002
    Date of Patent: September 16, 2003
    Assignee: Davy Process Technology Limited
    Inventors: David Mark Sutton, Andrew George Hiles, Adrian Francis Backes
  • Patent number: RE39794
    Abstract: A process is described for the co-production of maleic anhydride and at least one C4 compound selected from butane-1,4-diol, ?-butyrolactone, and tetrahydrofuran in which maleic anhydride is produced by partial oxidation of a hydrocarbon feedstock selected from C4 hydrocarbons and benzene to yield a vaporous reaction effluent stream comprising maleic anhydride, water, unconverted hydrocarbon feedstock, and carbon oxides. A part of the maleic anhydride present in the vaporous reaction effluent stream is condensed to form a crude maleic anhydride stream and leave a residual vaporous stream containing residual amounts of maleic anhydride. Further maleic anhydride is absorbed from the residual vaporous stream by absorption in an organic solvent, water or an aqueous solution. Maleic anhydride is then recovered from the loaded liquid absorptions medium.
    Type: Grant
    Filed: October 4, 2000
    Date of Patent: August 21, 2007
    Assignee: Davy Process Technology Limited
    Inventors: David Mark Sutton, Andrew George Hiles, Adrian Francis Backes