By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/880)
  • Patent number: 10041921
    Abstract: The invention relates to a method for producing organic amino compounds from organic nitro compounds, wherein the organic nitro compound hydrogenated to the organic amino compound with a hydrogen-containing gas stream by means of a catalyst, the reaction course of the hydrogenation being monitored by analysis of secondary products forming during hydrogenation, wherein the method is characterized in that the concentration of one or more gaseous secondary products is determined in the gas phase and if the concentration falls below a predefinable minimum concentration the hydrogenating activity of the catalyst is increased. The present invention also relates to a device for performing said method.
    Type: Grant
    Filed: January 21, 2014
    Date of Patent: August 7, 2018
    Assignee: COVESTRO DEUTSCHLAND AG
    Inventors: Bernd Pennemann, Bodo Temme
  • Patent number: 9464026
    Abstract: A process for recovering and using an carboxylic acid derived from a fermentation broth by means of making an ester of the free carboxylic acid and alcohol in carbon dioxide (CO2) without the presence of any other acid catalyst at a reaction temperature and pressure that corresponds to supercritical, critical or near critical conditions for the alcohol and/or CO2 is described. The process can constitute part of a general process of refining carboxylic acids derived from a fermentation broth for use in the production of a variety of chemical compounds, such as C4 platform compounds, polymers, or fuels.
    Type: Grant
    Filed: December 9, 2013
    Date of Patent: October 11, 2016
    Assignee: ARCHER-DANIELS MIDLAND COMPANY
    Inventors: Kenneth Stensrud, Padmesh Venkitasubramanian
  • Patent number: 9181155
    Abstract: Process for the catalytic production of alcohol products, wherein by-products comprising ketone, aldehyde and ester compounds contained in the alcohol product are subjected to hydrogenation with a hydrogen-containing purge gas.
    Type: Grant
    Filed: October 18, 2012
    Date of Patent: November 10, 2015
    Assignee: Haldor Topsoe A/S
    Inventor: Christian Wix
  • Patent number: 9035110
    Abstract: The present invention relates to a process for heat integration in the preparation of saturated C3-C20-alcohols, in which a hydrogenation feed comprising at least one C3-C20-aldehyde is hydrogenated in the presence of a hydrogen-comprising gas in a hydrogenation zone and a discharge is taken off from the hydrogenation zone and subjected to distillation in at least one distillation column to give a fraction enriched in saturated C3-C20-alcohols.
    Type: Grant
    Filed: March 6, 2013
    Date of Patent: May 19, 2015
    Assignee: BASF SE
    Inventors: Roland Krokoszinski, Karl-Heinz Walczuch
  • Publication number: 20150118174
    Abstract: Provided is a fragrance composition containing a compound that is highly harmonious with other various fragrances and that can impart a stronger floral feeling by being blended. A fragrance composition containing 3,6-dimethyl-heptane-2-ol. The fragrance composition may further contain at least one selected from the group consisting of, for example, 7-methyloctane-3-ol, esters, carbonates, aldehydes, ethers, lactones, and alcohols other than 3,6-dimethylheptane-2-ol.
    Type: Application
    Filed: May 30, 2013
    Publication date: April 30, 2015
    Applicant: Kao Corporation
    Inventors: Junko Ueda, Yoshiharu Ataka, Takahiro Asada, Naotoshi Toki
  • Patent number: 9000235
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using an extractive distillation column. The column yields a residue that comprises ethanol, acetic acid, and the extractive agent. The extractive agent may be water and may be separated from the residue and returned to the extractive distillation column.
    Type: Grant
    Filed: May 28, 2014
    Date of Patent: April 7, 2015
    Assignee: Celanese International Corporation
    Inventors: David Lee, Lincoln Sarager, Trinity Hale, Victor J. Johnston
  • Patent number: 9000232
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using an extractive distillation column. The column yields a first residue that comprises ethanol, ethyl acetate, acetic acid, and water. The first residue is separated in a second column to yield a second distillate comprising ethanol and ethyl acetate. The second distillate is then separated in a third column to yield a third distillate comprising ethyl acetate and a third residue comprising ethanol.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: April 7, 2015
    Assignee: Celanese International Corporation
    Inventors: R. Jay Warner, Victor J. Johnston, David Lee, Adam Orosco
  • Patent number: 8975450
    Abstract: Ethanol production processes using a mixed feed comprising from 20 to 95 wt. % acetic acid, from 5 to 80 wt. % acetic anhydride, and from 0 to 20 wt. % esters selected from the group consisting of methyl acetate, ethyl acetate, or mixtures thereof are disclosed herein. The process comprises contacting the mixed feed with hydrogen in the vapor phase in a reactor in the presence of a catalyst comprising tin, cobalt, platinum, and combinations thereof to form a crude ethanol product having an ethanol to water molar ratio of greater than 1 and separating the crude ethanol product in one or more distillation columns to yield an ethyl acetate stream and an ethanol stream. The process may be integrated with an acetic anhydride production process to obtain further economic savings.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: March 10, 2015
    Assignee: Celanese International Corporation
    Inventor: Mark O. Scates
  • Publication number: 20150045586
    Abstract: The present invention provides a process for the production of aldehydes and/or alcohols, which process comprises the steps of: (a) reacting an oxygenate and/or olefinic feed in a reactor in the presence of a molecular sieve catalyst to form an effluent comprising olefins, comprising propylene; (b) separating the effluent comprising olefins as obtained in step (a) into at least a first olefinic product fraction comprising propylene and a second olefinic product fraction; (c) subjecting at least part of the first olefinic product fraction as obtained in step (b) to a hydroformylation process to form aldehydes; (d) separating at least part of the aldehydes as obtained in step (c) into at least a first product fraction of aldehydes and a second product fraction of aldehydes; and (e) hydrogenating at least part of the aldehydes in the first and/or second product fraction of aldehydes as obtained in step (d) to form a first product fraction of alcohols and/or a second product fraction of alcohols; (f) recycling at
    Type: Application
    Filed: December 21, 2012
    Publication date: February 12, 2015
    Inventors: Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
  • Patent number: 8946489
    Abstract: Biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) is processed to produce useful products, such as fuels. For example, systems can use feedstock materials, such as cellulosic and/or lignocellulosic materials and/or starchy or sugary materials, to produce ethanol and/or butanol, e.g., by fermentation.
    Type: Grant
    Filed: March 17, 2014
    Date of Patent: February 3, 2015
    Assignee: Xyleco, Inc.
    Inventor: Marshall Medoff
  • Patent number: 8889913
    Abstract: A hydride transfer process within a reaction between an alcohol and a ketone and in the presence of a heterogeneous catalyst is described. The process can transfer a hydride from an alcohol to a ketone, thus enabling reduction of the ketone and oxidation of the alcohol. Further described, is a process for the simultaneous preparation of cyclohexanone and isopropanol enabling an optimized industrial operation. A mixture of compounds useful for implementing the process and comprising two different ketones and two different alcohols is also described.
    Type: Grant
    Filed: July 20, 2011
    Date of Patent: November 18, 2014
    Assignee: Rhodia Operations
    Inventors: Roland Jacquot, Philippe Marion
  • Publication number: 20140249321
    Abstract: The present invention relates in a first aspect to a process for hydrogenation of ketones having at least a carbon-carbon double bond in the y,8-position to the keto group by hydrogen in the presence of at least one chiral iridium complex of formula (I), where R1 represents a group of formula (II) or (III) or (IV). It has been shown that this process leads to a strong increase in preferential formation of a single isomer. The process is particularly suitable for the hydrogenation of y,8-unsaturated ketones which can be used as flavours and fragrances or for the preparation of vitamin E and its derivatives or of flavours and fragrances.
    Type: Application
    Filed: June 13, 2012
    Publication date: September 4, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Marc-André Mueller, Andreas Pfaltz, Jonathan Medlock
  • Patent number: 8809594
    Abstract: Disclosed is a process for the production of higher aldehydes from lower alcohols using a two-stage vapor phase heterogeneous catalyst system. Ethanol feeds afford aldehydes such as butyraldehyde and crotonaldehyde while butanol feeds yield 2-ethylhexanal and 2-ethylhexenal. Higher product selectivities are obtained when the alcohol is first dehydrogenated in the upper catalyst stage followed by aldol condensation of the resulting lower aldehyde to a higher aldehyde.
    Type: Grant
    Filed: September 21, 2012
    Date of Patent: August 19, 2014
    Assignee: Eastman Chemical Company
    Inventors: David William Norman, Damon Ray Billodeaux, Melissa Dawn Page
  • Patent number: 8748675
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using an extractive distillation column. The column yields a residue that comprises ethanol, acetic acid, and the extractive agent. The extractive agent may be water and may be separated from the residue and returned to the extractive distillation column.
    Type: Grant
    Filed: June 16, 2011
    Date of Patent: June 10, 2014
    Assignee: Celanese International Corporation
    Inventors: David Lee, Lincoln Sarager, Trinity Horton, Victor J. Johnston
  • Patent number: 8748676
    Abstract: In one embodiment, the invention is to a process for purifying a crude ethanol product. The process comprises the step of hydrogenating acetic acid in a first reaction zone in the presence of a first catalyst to form the crude ethanol product comprising ethanol, acetaldehyde, acetic acid, water, and acetal. The process further comprises the step of separating at least a portion of the crude ethanol product into a refined ethanol stream and a by-product stream. The refined ethanol stream comprises ethanol and acetaldehyde; and the by-product stream comprises acetic acid and a substantial portion of the water from the crude ethanol product. The process further comprises the step of hydrolyzing in a second reaction zone at least a portion of the acetal.
    Type: Grant
    Filed: August 3, 2011
    Date of Patent: June 10, 2014
    Assignee: Celanese International Corporation
    Inventors: Adam Orosco, Lincoln Sarager, R. Jay Warner, Radmila Jevtic
  • Patent number: 8716537
    Abstract: Biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) is processed to produce useful products, such as fuels. For example, systems can use feedstock materials, such as cellulosic and/or lignocellulosic materials and/or starchy or sugary materials, to produce ethanol and/or butanol, e.g., by fermentation.
    Type: Grant
    Filed: October 22, 2012
    Date of Patent: May 6, 2014
    Assignee: Xyleco, Inc.
    Inventor: Marshall Medoff
  • Patent number: 8704011
    Abstract: A crude ethanol product obtained from the hydrogenation of acetic acid comprises ethanol and ethyl acetate. Using a distillation column operated at a pressure of from 0.1 to 100 kPa, the ethyl acetate and ethanol may be effectively separated. In addition, maintaining the amount of water that is fed to the distillation column to an amount less than 10 wt. %, based on the weight of all components fed to the distillation column, provides an energy benefit.
    Type: Grant
    Filed: April 26, 2011
    Date of Patent: April 22, 2014
    Assignee: Celanese International Corporation
    Inventors: Lincoln Sarager, R. Jay Warner, Trinity Horton, David Lee, Victor J. Johnston, Manuel Salado
  • Patent number: 8685355
    Abstract: A method of forming methanol, formaldehyde, formic acid and ammonium pentaborate tetrahydrate includes the steps of providing ammonium hydroxide and producing air bubbles within the ammonium hydroxide to form a solution. Sodium borohydride is added and dissolved within the solution of air bubbled ammonium hydroxide to form methanol, formaldehyde, formic acid and ammonium pentaborate tetrahydrate. An alternative method of forming methanol, formaldehyde, formic acid and ammonium pentaborate tetrahydrate is also provided which includes the steps of providing ammonium hydroxide and dissolving sodium borohydride therein to form a solution. Sodium bicarbonate is added to the solution of ammonium hydroxide and sodium borohydride to form methanol, formaldehyde, formic acid and ammonium pentaborate tetrahydrate.
    Type: Grant
    Filed: March 27, 2012
    Date of Patent: April 1, 2014
    Assignee: Biologistics LLC
    Inventor: Michael A. Madson
  • Patent number: 8680342
    Abstract: Purifying and/or recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid from an feed stream comprising water. The presence of water does not significantly impact acid conversion or selectivity to ethanol. Further the addition of water allows for improved recovery of ethanol.
    Type: Grant
    Filed: April 26, 2011
    Date of Patent: March 25, 2014
    Assignee: Celanese International Corporation
    Inventors: Radmila Jevtic, Victor J. Johnston, Tianshu Pan, R. Jay Warner, Heiko Weiner, Josefina T. Chapman
  • Publication number: 20130261348
    Abstract: Ethane is oxidized to ethylene and/or oxygenates that comprise acetic acid. The acetic acid may be converted to ethanol by hydrogenation. The ethylene may be converted to ethanol by hydration.
    Type: Application
    Filed: March 28, 2012
    Publication date: October 3, 2013
    Applicant: Celanese International Corporation
    Inventors: Mark Scates, Heiko Weiner, Zhenhua Zhou, James Zink
  • Patent number: 8546621
    Abstract: The present invention is directed to a process for the manufacture of 3,7-dimethyl-1-octen-3-ol comprising the following steps: a) hydrogenation of 6-methyl-5-hepten-2-on to 6-methyl-2-heptanon in the presence of hydrogen and a palladium containing catalyst on a carrier selected from the group consisting of carbon, calcium carbonate and aluminum oxide. b) reaction of 6-methyl-2-heptanon with acetylene to 3,7-dimethyl-1-octin-3-ol in the presence of ammonia and potassium hydroxide and in the absence of any additional organic solvent; c) hydrogenation of 3,7-dimethyl-1-octin-3-ol to 3,7-dimethyl-1-octen-3-ol in the presence of hydrogen and a palladium containing catalyst on a carrier selected from the group consisting of calcium carbonate, aluminum oxide, silica, porous glass, carbon or graphite, and barium sulphate, with the proviso that the catalyst additionally contains lead when the carrier is calcium carbonate.
    Type: Grant
    Filed: August 24, 2011
    Date of Patent: October 1, 2013
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Johannes Tschumi, Jonathan Medlock
  • Publication number: 20130237726
    Abstract: The present invention relates to a process for heat integration in the preparation of saturated C3-C20-alcohols, in which a hydrogenation feed comprising at least one C3-C20-aldehyde is hydrogenated in the presence of a hydrogen-comprising gas in a hydrogenation zone and a discharge is taken off from the hydrogenation zone and subjected to distillation in at least one distillation column to give a fraction enriched in saturated C3-C20-alcohols.
    Type: Application
    Filed: March 6, 2013
    Publication date: September 12, 2013
    Inventors: Roland Krokoszinski, Karl-Heinz Walczuch
  • Publication number: 20130158298
    Abstract: A process for producing alcohols from carbonaceous materials such as biomass. The carbonaceous material, such as biomass, is gasified to produce synthesis gas. The synthesis gas then is subjected to a plurality of reactions to produce alcohols having at least four carbon atoms such as butanol and isobutanol.
    Type: Application
    Filed: August 7, 2012
    Publication date: June 20, 2013
    Inventors: Anthony S. CARBONE, Stephane MARIE-ROSE, Esteban CHORNET
  • Publication number: 20130158299
    Abstract: A process for producing alcohols having three carbon atoms from carbonaceous materials such as biomass. The carbonaceous material, such as biomass, is gasified to produce synthesis gas. The synthesis gas then is subjected to a plurality of reactions to produce alcohols such as n-propanol and isopropanol.
    Type: Application
    Filed: August 7, 2012
    Publication date: June 20, 2013
    Inventors: Anthony S. Carbone, Stephane Marie-Rose, Esteban Chornet
  • Patent number: 8404902
    Abstract: The invention relates to a method for separating 1-butene from C4-containing hydrocarbon mixtures, comprising isobutene and 1-butene, by hydroformylation, wherein the catalytic system used is made of one of the transition metals of the group 8 to 10, preferably rhodium, and a bisphosphite ligand of the formula (I), where X is a divalent substituted or unsubstituted bisalkylene or bisarylene group having one or more heteroatom(s), Y is a divalent substituted or unsubstituted bisarylene or bisalkylene group having one or more heteroatom(s), Z is oxygen or NR9, and R1, R2, R3, R4 are identical or different, substituted or unsubstituted, linked, unlinked or condensed aryl or heteroaryl groups, and R9 is hydrogen or a substituted or unsubstituted alkyl or aryl group having one or more heteroatom(s), wherein the bisphosphite ligand of the formula (I) is used in an excess of a molar ratio of 100:1 to 1:1 to the transition metal, and that with a 1-butene conversion of more than 95% less than 5% of the present isobute
    Type: Grant
    Filed: April 28, 2009
    Date of Patent: March 26, 2013
    Assignee: Evonik Oxeno GmbH
    Inventors: Burkard Kreidler, Klaus-Diether Wiese, Dieter Hess, Detlef Selent, Armin Boerner
  • Publication number: 20120209021
    Abstract: The invention provides method of producing n-butyraldehyde using recombinant solventogenic bacteria and recombinant microorganisms.
    Type: Application
    Filed: February 8, 2012
    Publication date: August 16, 2012
    Applicant: EASTMAN RENEWABLE MATERIALS, LLC
    Inventors: Jay Kouba, Mounir Izallalen, Jill Bradshaw
  • Publication number: 20120184784
    Abstract: Methods and systems for hydrogenating an aldehyde or a ketone, including introducing a gas stream comprising hydrogen into a high shear device comprising a rotor and a stator; introducing a liquid stream comprising an aldehyde or ketone into the high shear device; forming a dispersion of the gas stream and the liquid stream in the high shear device; and hydrogenating at least a portion of the aldehyde or ketone in the dispersion.
    Type: Application
    Filed: March 29, 2012
    Publication date: July 19, 2012
    Applicant: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Patent number: 8212087
    Abstract: Biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) is processed to produce useful products, such as fuels. For example, systems can use feedstock materials, such as cellulosic and/or lignocellulosic materials and/or starchy or sugary materials, to produce ethanol and/or butanol, e.g., by fermentation.
    Type: Grant
    Filed: April 3, 2009
    Date of Patent: July 3, 2012
    Assignee: Xyleco, Inc.
    Inventor: Marshall Medoff
  • Publication number: 20120116120
    Abstract: In one aspect, the inventive process comprises a process for pyrolyzing a hydrocarbon feedstock containing nonvolatiles in a regenerative pyrolysis reactor system. The inventive process comprises: (a) heating the nonvolatile-containing hydrocarbon feedstock upstream of a regenerative pyrolysis reactor system to a temperature sufficient to form a vapor phase that is essentially free of nonvolatiles and a liquid phase containing the nonvolatiles; (b) separating said vapor phase from said liquid phase; (c) feeding the separated vapor phase to the pyrolysis reactor system; and (d) converting the separated vapor phase in said pyrolysis reactor system to form a pyrolysis product.
    Type: Application
    Filed: January 13, 2012
    Publication date: May 10, 2012
    Inventors: Paul F. Keusenkothen, James N. McCoy, Frank Hershkowitz
  • Patent number: 8138379
    Abstract: The invention relates to a one-stage continuous process for hydroformylating olefins having at least 5 carbon atoms to the corresponding aldehydes and/or alcohols having at least 6 carbon atoms in the presence of unmodified cobalt catalysts in a process in which, in the presence of an aqueous phase and of an organic phase, catalyst formation, catalyst extraction and hydroformylation proceed in the same reactor, which is characterized in that more aqueous cobalt salt solution is fed into the reactor as an aqueous phase with the liquid reaction mixture and is discharged from the reactor with the gas phase, and in that the level of the aqueous bottom phase is kept constant by continuously conducting a portion of the aqueous bottom phase out of the reactor.
    Type: Grant
    Filed: October 28, 2008
    Date of Patent: March 20, 2012
    Assignee: Evonik Oxeno GmbH
    Inventors: Hans-Gerd Lueken, Stefan Drees, Alfred Kaizik, Wilfried Bueschken
  • Patent number: 8129571
    Abstract: The invention relates to a process for the continuous preparation of aldehydes and/or alcohols having at least 6 carbon atoms by multistage hydroformylation of olefins or olefin mixtures having at least 5 carbon atoms in the presence of unmodified cobalt complexes, in which at least two reactors are operated at different temperatures in the temperature range from 100 to 220° C. and pressures of from 100 to 400 bar, which is characterized in that a) one reactor is operated at temperatures above 160° C.
    Type: Grant
    Filed: October 28, 2008
    Date of Patent: March 6, 2012
    Assignee: Evonik Oxeno GmbH
    Inventors: Hans-Gerd Lueken, Alfred Kaizik, Stefan Drees, Wilfried Bueschken
  • Publication number: 20120053353
    Abstract: The present invention is directed to a process for the manufacture of 3,7-dimethyl-1-octen-3-ol comprising the following steps: a) hydrogenation of 6-methyl-5-hepten-2-on to 6-methyl-2-heptanon in the presence of hydrogen and a palladium containing catalyst on a carrier selected from the group consisting of carbon, calcium carbonate and aluminum oxide. b) reaction of 6-methyl-2-heptanon with acetylene to 3,7-dimethyl-1-octin-3-ol in the presence of ammonia and potassium hydroxide and in the absence of any additional organic solvent; c) hydrogenation of 3,7-dimethyl-1-octin-3-ol to 3,7-dimethyl-1-octen-3-ol in the presence of hydrogen and a palladium containing catalyst on a carrier selected from the group consisting of calcium carbonate, aluminum oxide, silica, porous glass, carbon or graphite, and barium sulphate, with the proviso that the catalyst additionally contains lead when the carrier is calcium carbonate.
    Type: Application
    Filed: August 24, 2011
    Publication date: March 1, 2012
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner BONRATH, Johannes Tschumi, Jonathan Medlock
  • Publication number: 20110312864
    Abstract: The present invention relates to alcohols and in particular to C4 to C15 alcohols that are used in the production of esters.
    Type: Application
    Filed: December 3, 2009
    Publication date: December 22, 2011
    Inventors: Allen D. Godwin, Philippe L. Buess, Raphael F. Caers, Arie Van Vliet, Eddy T.A. Van Driessche, Alfons Cuyckens
  • Patent number: 8013189
    Abstract: In a process for the accelerated reduction of organic substrates, selected from the group consisting of esters, amides, nitriles, acids, ketones, imines or mixtures thereof, they are reacted with an amine borane, sulfide borane or ether borane complex as a borane source in the presence of organic accelerator compounds containing either Lewis acidic or Lewis basic sites in their structure, of which the Lewis acidic site can coordinate with the carbonyl or nitrile or imine group of the substrate or the Lewis basic site can coordinate with the borane.
    Type: Grant
    Filed: September 21, 2007
    Date of Patent: September 6, 2011
    Assignee: BASF SE
    Inventors: Elizabeth Burkhardt, Alex J. Attlesey, Christopher P. Sutton, Karl Matos
  • Patent number: 7935851
    Abstract: High purity isobutylene streams are obtained by the hydroformylation of mixed butene streams containing butene-1 and isobutylene (and optionally butene-2) under conditions that hydroformylate primarily butene-1 to yield a mixture of valeraldehyde and isobutylene, which may be separated out as an enriched isobutylene stream and used in the production of methyl tertiary butyl ether, tertiary butyl alcohol, di-isobutylene or polyisobutylene.
    Type: Grant
    Filed: September 17, 2004
    Date of Patent: May 3, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Raphael Frans Caers, Eddy Theophile Van Driessche
  • Publication number: 20110071321
    Abstract: The invention relates to a method for separating 1-butene from C4-containing hydrocarbon mixtures, comprising isobutene and 1-butene, by hydroformylation, wherein the catalytic system used is made of one of the transition metals of the group 8 to 10, preferably rhodium, and a bisphosphite ligand of the formula (I), where X is a divalent substituted or unsubstituted bisalkylene or bisarylene group having one or more heteroatom(s), Y is a divalent substituted or unsubstituted bisarylene or bisalkylene group having one or more heteroatom(s), Z is oxygen or NR9, and R1, R2, R3, R4 are identical or different, substituted or unsubstituted, linked, unlinked or condensed aryl or heteroaryl groups, and R9 is hydrogen or a substituted or unsubstituted alkyl or aryl group having one or more heteroatom(s), wherein the bisphosphite ligand of the formula (I) is used in an excess of a molar ratio of 100:1 to 1:1 to the transition metal, and that with a 1-butene conversion of more than 95% less than 5% of the present isobute
    Type: Application
    Filed: April 28, 2009
    Publication date: March 24, 2011
    Applicant: EVONIK OXENO GMBH
    Inventors: Burkard Kreidler, Klaus-Diether Wiese, Dieter Hess, Detlef Selent, Armin Boerner
  • Patent number: 7884253
    Abstract: The invention provides methods and apparatus for selectively producing ethanol from syngas. As disclosed herein, syngas derived from cellulosic biomass (or other sources) can be catalytically converted into methanol, which in turn can be catalytically converted into acetic acid or acetates. Finally, the acetic acid or acetates can be reduced to ethanol according to several variations. In some embodiments, yields of ethanol from biomass can exceed 100 gallons per dry ton of biomass.
    Type: Grant
    Filed: August 25, 2009
    Date of Patent: February 8, 2011
    Assignee: Range Fuels, Inc.
    Inventors: Ronald C. Stites, Jerrod Hohman
  • Patent number: 7858831
    Abstract: This invention is directed to a method of performing a stereoselective reaction without use of a solvent comprising contacting a reactant with a chiral reagent under sonication conditions to form an excess of an enantiomer.
    Type: Grant
    Filed: December 19, 2008
    Date of Patent: December 28, 2010
    Assignee: The Regents of the University of California
    Inventors: Matthew P. Meyer, Hui Zhu
  • Patent number: 7842844
    Abstract: Process for the conversion of hydrocarbons to ethanol and optionally acetic acid by converting hydrocarbon in a syngas reactor into a stream A comprising a mixture of carbon oxide(s) and hydrogen preferably having a H2/CO molar ratio between 1.5 and 2.5, converting at least part of stream A in the presence of a particulate catalyst in a reactor under a temperature between 150 and 400° C. and a pressure of 5 to 200 bar, into a C2-oxygenates stream B, where stream B includes water, alkanes, ethanol, acetaldehyde, ethyl acetate and acetic acid, which together represent least 80% by weight of the products obtained from the C2-oxygenates conversion reactor. The C2-oxygenates stream B is separated into a stream C comprising H2, CO, CO2 and alkanes, and a stream D including 15 to 40 wt % of acetic acid, 10 to 40 wt % of acetaldehyde and 15 to 40 wt % of ethanol.
    Type: Grant
    Filed: June 29, 2006
    Date of Patent: November 30, 2010
    Assignee: BP Chemicals Limited
    Inventor: Martin Philip Atkins
  • Patent number: 7825286
    Abstract: This invention offers 6,8,10-undecatrien-3-ol and 6,8,10-undecatrien-4-ol. These compounds possess not only woody green note, but also fruity note rich in naturality and freshness, and aroma compositions blended therewith are useful for imparting fragrance and flavor to food and beverage, perfumed cosmetics, medicaments and the like.
    Type: Grant
    Filed: June 6, 2008
    Date of Patent: November 2, 2010
    Assignee: T. Hasegawa Co., Ltd.
    Inventors: Akira Nakanishi, Yasutaka Ohkubo, Naomi Tomita, Tomoko Maeda, Norio Miyazawa
  • Patent number: 7799958
    Abstract: The present invention relates to a process for the production of iso-propanol by liquid phase hydrogenation of acetone to iso-propanol in at least two hydrogenation reaction stages, each reaction stage comprising a hydrogenation reaction zone, wherein the hydrogenation reaction product leaving the reaction zone of the first reaction stage contains unreacted acetone and a product stream comprising acetone and iso-propanol is transferred to the reaction zone of a subsequent reaction stage said product stream having at the inlet to the reaction zone of said subsequent reaction stage a temperature of 60 to 100° C., wherein the temperature of the product stream leaving the reaction zone of said subsequent reaction stage at the outlet from said reaction zone is at most 40° C. higher than the temperature of the product stream entering said reaction zone at the inlet to said reaction zone and the temperature in said subsequent reaction zone does not exceed 125° C.
    Type: Grant
    Filed: October 3, 2008
    Date of Patent: September 21, 2010
    Assignee: Barclays Bank PLC
    Inventors: Ralf Bonmann, Werner Pompetzki, Markus Weber
  • Patent number: 7790938
    Abstract: The invention relates to a process for producing an alcohol including hydrogenating an aldehyde using a hydrogenation catalyst and subjecting the resultant product to distillation/purification, wherein the resultant hydrogenation product is subjected to distillation/purification in the absence of the hydrogenation catalyst or in the presence of the hydrogenation catalyst in such an amount that does not cause a dehydrogenation reaction.
    Type: Grant
    Filed: June 6, 2005
    Date of Patent: September 7, 2010
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hiroki Kawasaki, Yuichi Fujita
  • Patent number: 7728178
    Abstract: This invention relates to a process for the production of aldehydes/alcohols and alkyl benzene. According to the invention, a hydrocarbon feed stream containing olefins and paraffins having an average number of carbon atoms from 10 to 18 per molecule, typically derived from the condensation product of a Fischer-Tropsch reaction is subjected to a hydroformylation reaction to provide a hydroformylation product containing aldehydes/alcohols and paraffins. An aldehyde/alcohol product is separated from the paraffins in the hydroformylation product to provide an aldehyde/alcohol product stream and a paraffin stream. The paraffin stream separated from the hydroformylation product is then subjected to a dehydrogenation reaction to form a dehydrogenation product containing olefins and paraffins, and the dehydrogenation product is subjected to an alkylation reaction to convert olefins to alkyl benzene.
    Type: Grant
    Filed: August 31, 2006
    Date of Patent: June 1, 2010
    Assignee: Sasol Technology (Proprietary) Limited
    Inventors: Ivan Philip Greager, James Christoffel Crause
  • Publication number: 20100130794
    Abstract: This invention offers 6,8,10-undecatrien-3-ol and 6,8,10-undecatrien-4-ol. These compounds possess not only woody green note, but also fruity note rich in naturality and freshness, and aroma compositions blended therewith are useful for imparting fragrance and flavor to food and beverage, perfumed cosmetics, medicaments and the like.
    Type: Application
    Filed: June 6, 2008
    Publication date: May 27, 2010
    Inventors: Akira Nakanishi, Yasutaka Ohkubo, Naomi Tomita, Tomoko Maeda, Norio Miyazawa
  • Patent number: 7718831
    Abstract: Method of asymmetrically hydrosilylating substrates using catalysts having a ligand of the compound of the formula (I) wherein R is optionally substituted alkyl, cycloalkyl, aryl or heteroaryl; R? is hydrogen, optionally substituted lower alkyl; and R? is hydrogen, halogen, optionally substituted alkyl, hydroxy, amino (e.g., primary, secondary or tertiary), alkenyl; or an enantiomer thereof; or an enantiomeric mixture thereof with a transition metal. Particularly suitable reactions include the asymmetric hydrosilylation of ketones.
    Type: Grant
    Filed: February 16, 2006
    Date of Patent: May 18, 2010
    Assignee: The Hong Kong Polytechnic University
    Inventors: Albert S Chan, Jianxin Ji, Jing Wu
  • Patent number: 7667058
    Abstract: Disclosed are heterogeneous processes (i) for the hydrogenation of a compound containing at least one unsaturated carbon-carbon bond, and (ii) for the hydro-dehalogenation of a compound containing at least one C—Cl, C—Br or C—I bond. The processes comprise reacting said compound with a hydrogenating agent and a heterogeneous hydrogenation catalyst in the presence of an ionic liquid.
    Type: Grant
    Filed: May 17, 2002
    Date of Patent: February 23, 2010
    Assignee: The Queen's University of Belfast
    Inventors: Kris Anderson, Peter Goodrich, Christopher Hardacre, Sarah Elizabeth Jane McMath
  • Patent number: 7652173
    Abstract: This invention relates to a process for the production of alcohols and/or aldehydes. A hydrocarbon feed stream containing paraffins and olefins, typically in which more than 5% by volume of olefin molecules in the hydrocarbon feed stream have a total number of carbon atoms which is different from the total number of carbon atoms of the most abundant two (preferably three) carbon numbers of olefins (by carbon number) in the hydrocarbon stream, is subjected to a hydroformylation reaction in which olefins are converted to alcohols and/or aldehydes. Paraffins in the hydroformylation product are then separated from alcohols and/or aldehydes by azeotropic distillation in an azeotropic distillation column. The invention also relates to a method for separating alcohols/aldehydes from paraffins in a hydrocarbon feed stream in an azeotropic distillation column using a mid-boiling polar entrainer.
    Type: Grant
    Filed: August 31, 2006
    Date of Patent: January 26, 2010
    Assignee: Sasol Technology (Proprietary) Limited
    Inventor: James Christoffel Crause
  • Publication number: 20090270658
    Abstract: Methods for preparing self-aldol condensation products of prenyl aldehyde (3-methyl-2-butenal) by use of an amine catalyst under weakly acidic conditions at temperatures of 10° C. or higher are disclosed. Methods are disclosed for the selective formation of ?-1,2-adducts and ?-1,2-adducts of prenyl aldehyde, and for the formation of specialty compositions useful in the flavor and fragrance industries.
    Type: Application
    Filed: April 24, 2008
    Publication date: October 29, 2009
    Inventor: James H. Babler
  • Patent number: 7524997
    Abstract: A hydrogenation catalyst is used for the catalytic hydrogenation of an ester-containing aldehyde mixture and the catalyst contains a ?-alumina having a BET surface area of from 70 to 350 m2/g as support material, and at least one component having hydrogenation activity and being selected from the group consisting of nickel, cobalt and mixtures thereof.
    Type: Grant
    Filed: July 28, 2006
    Date of Patent: April 28, 2009
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Alfred Kaizik, Hans-Gerd Lüken, Michael Grass, Dietrich Maschmeyer, Wilfried Büschken
  • Publication number: 20090093656
    Abstract: The present invention relates to a process for the production of iso-propanol by liquid phase hydrogenation of acetone to iso-propanol in at least two hydrogenation reaction stages, each reaction stage comprising a hydrogenation reaction zone, wherein the hydrogenation reaction product leaving the reaction zone of the first reaction stage contains unreacted acetone and a product stream comprising acetone and iso-propanol is transferred to the reaction zone of a subsequent reaction stage said product stream having at the inlet to the reaction zone of said subsequent reaction stage a temperature of 60 to 100° C., wherein the temperature of the product stream leaving the reaction zone of said subsequent reaction stage at the outlet from said reaction zone is at most 40° C. higher than the temperature of the product stream entering said reaction zone at the inlet to said reaction zone and the temperature in said subsequent reaction zone does not exceed 125° C.
    Type: Application
    Filed: October 3, 2008
    Publication date: April 9, 2009
    Applicant: INEOS PHENOT GMBH & CO. KG
    Inventors: Ralf Bonmann, Werner Pompetzki, Markus Weber