By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/880)
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Patent number: 10041921Abstract: 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: GrantFiled: January 21, 2014Date of Patent: August 7, 2018Assignee: COVESTRO DEUTSCHLAND AGInventors: Bernd Pennemann, Bodo Temme
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Patent number: 9464026Abstract: 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: GrantFiled: December 9, 2013Date of Patent: October 11, 2016Assignee: ARCHER-DANIELS MIDLAND COMPANYInventors: Kenneth Stensrud, Padmesh Venkitasubramanian
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Patent number: 9181155Abstract: 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: GrantFiled: October 18, 2012Date of Patent: November 10, 2015Assignee: Haldor Topsoe A/SInventor: Christian Wix
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Patent number: 9035110Abstract: 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: GrantFiled: March 6, 2013Date of Patent: May 19, 2015Assignee: BASF SEInventors: Roland Krokoszinski, Karl-Heinz Walczuch
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Publication number: 20150118174Abstract: 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: ApplicationFiled: May 30, 2013Publication date: April 30, 2015Applicant: Kao CorporationInventors: Junko Ueda, Yoshiharu Ataka, Takahiro Asada, Naotoshi Toki
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Patent number: 9000235Abstract: 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: GrantFiled: May 28, 2014Date of Patent: April 7, 2015Assignee: Celanese International CorporationInventors: David Lee, Lincoln Sarager, Trinity Hale, Victor J. Johnston
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Patent number: 9000232Abstract: 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: GrantFiled: April 26, 2012Date of Patent: April 7, 2015Assignee: Celanese International CorporationInventors: R. Jay Warner, Victor J. Johnston, David Lee, Adam Orosco
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Patent number: 8975450Abstract: 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: GrantFiled: March 15, 2013Date of Patent: March 10, 2015Assignee: Celanese International CorporationInventor: Mark O. Scates
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Publication number: 20150045586Abstract: 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 atType: ApplicationFiled: December 21, 2012Publication date: February 12, 2015Inventors: Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
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Patent number: 8946489Abstract: 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: GrantFiled: March 17, 2014Date of Patent: February 3, 2015Assignee: Xyleco, Inc.Inventor: Marshall Medoff
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Patent number: 8889913Abstract: 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: GrantFiled: July 20, 2011Date of Patent: November 18, 2014Assignee: Rhodia OperationsInventors: Roland Jacquot, Philippe Marion
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Publication number: 20140249321Abstract: 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: ApplicationFiled: June 13, 2012Publication date: September 4, 2014Applicant: DSM IP ASSETS B.V.Inventors: Marc-André Mueller, Andreas Pfaltz, Jonathan Medlock
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Patent number: 8809594Abstract: 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: GrantFiled: September 21, 2012Date of Patent: August 19, 2014Assignee: Eastman Chemical CompanyInventors: David William Norman, Damon Ray Billodeaux, Melissa Dawn Page
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Patent number: 8748675Abstract: 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: GrantFiled: June 16, 2011Date of Patent: June 10, 2014Assignee: Celanese International CorporationInventors: David Lee, Lincoln Sarager, Trinity Horton, Victor J. Johnston
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Patent number: 8748676Abstract: 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: GrantFiled: August 3, 2011Date of Patent: June 10, 2014Assignee: Celanese International CorporationInventors: Adam Orosco, Lincoln Sarager, R. Jay Warner, Radmila Jevtic
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Patent number: 8716537Abstract: 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: GrantFiled: October 22, 2012Date of Patent: May 6, 2014Assignee: Xyleco, Inc.Inventor: Marshall Medoff
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Patent number: 8704011Abstract: 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: GrantFiled: April 26, 2011Date of Patent: April 22, 2014Assignee: Celanese International CorporationInventors: Lincoln Sarager, R. Jay Warner, Trinity Horton, David Lee, Victor J. Johnston, Manuel Salado
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Patent number: 8685355Abstract: 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: GrantFiled: March 27, 2012Date of Patent: April 1, 2014Assignee: Biologistics LLCInventor: Michael A. Madson
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Process for recovering alcohol produced by hydrogenating an acetic acid feed stream comprising water
Patent number: 8680342Abstract: 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: GrantFiled: April 26, 2011Date of Patent: March 25, 2014Assignee: Celanese International CorporationInventors: Radmila Jevtic, Victor J. Johnston, Tianshu Pan, R. Jay Warner, Heiko Weiner, Josefina T. Chapman -
Publication number: 20130261348Abstract: 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: ApplicationFiled: March 28, 2012Publication date: October 3, 2013Applicant: Celanese International CorporationInventors: Mark Scates, Heiko Weiner, Zhenhua Zhou, James Zink
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Patent number: 8546621Abstract: 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: GrantFiled: August 24, 2011Date of Patent: October 1, 2013Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Johannes Tschumi, Jonathan Medlock
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Publication number: 20130237726Abstract: 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: ApplicationFiled: March 6, 2013Publication date: September 12, 2013Inventors: Roland Krokoszinski, Karl-Heinz Walczuch
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Publication number: 20130158298Abstract: 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: ApplicationFiled: August 7, 2012Publication date: June 20, 2013Inventors: Anthony S. CARBONE, Stephane MARIE-ROSE, Esteban CHORNET
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Publication number: 20130158299Abstract: 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: ApplicationFiled: August 7, 2012Publication date: June 20, 2013Inventors: Anthony S. Carbone, Stephane Marie-Rose, Esteban Chornet
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Patent number: 8404902Abstract: 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 isobuteType: GrantFiled: April 28, 2009Date of Patent: March 26, 2013Assignee: Evonik Oxeno GmbHInventors: Burkard Kreidler, Klaus-Diether Wiese, Dieter Hess, Detlef Selent, Armin Boerner
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Publication number: 20120209021Abstract: The invention provides method of producing n-butyraldehyde using recombinant solventogenic bacteria and recombinant microorganisms.Type: ApplicationFiled: February 8, 2012Publication date: August 16, 2012Applicant: EASTMAN RENEWABLE MATERIALS, LLCInventors: Jay Kouba, Mounir Izallalen, Jill Bradshaw
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Publication number: 20120184784Abstract: 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: ApplicationFiled: March 29, 2012Publication date: July 19, 2012Applicant: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 8212087Abstract: 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: GrantFiled: April 3, 2009Date of Patent: July 3, 2012Assignee: Xyleco, Inc.Inventor: Marshall Medoff
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Publication number: 20120116120Abstract: 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: ApplicationFiled: January 13, 2012Publication date: May 10, 2012Inventors: Paul F. Keusenkothen, James N. McCoy, Frank Hershkowitz
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Patent number: 8138379Abstract: 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: GrantFiled: October 28, 2008Date of Patent: March 20, 2012Assignee: Evonik Oxeno GmbHInventors: Hans-Gerd Lueken, Stefan Drees, Alfred Kaizik, Wilfried Bueschken
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Patent number: 8129571Abstract: 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: GrantFiled: October 28, 2008Date of Patent: March 6, 2012Assignee: Evonik Oxeno GmbHInventors: Hans-Gerd Lueken, Alfred Kaizik, Stefan Drees, Wilfried Bueschken
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Publication number: 20120053353Abstract: 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: ApplicationFiled: August 24, 2011Publication date: March 1, 2012Applicant: DSM IP ASSETS B.V.Inventors: Werner BONRATH, Johannes Tschumi, Jonathan Medlock
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Publication number: 20110312864Abstract: The present invention relates to alcohols and in particular to C4 to C15 alcohols that are used in the production of esters.Type: ApplicationFiled: December 3, 2009Publication date: December 22, 2011Inventors: Allen D. Godwin, Philippe L. Buess, Raphael F. Caers, Arie Van Vliet, Eddy T.A. Van Driessche, Alfons Cuyckens
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Patent number: 8013189Abstract: 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: GrantFiled: September 21, 2007Date of Patent: September 6, 2011Assignee: BASF SEInventors: Elizabeth Burkhardt, Alex J. Attlesey, Christopher P. Sutton, Karl Matos
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Patent number: 7935851Abstract: 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: GrantFiled: September 17, 2004Date of Patent: May 3, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Raphael Frans Caers, Eddy Theophile Van Driessche
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Publication number: 20110071321Abstract: 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 isobuteType: ApplicationFiled: April 28, 2009Publication date: March 24, 2011Applicant: EVONIK OXENO GMBHInventors: Burkard Kreidler, Klaus-Diether Wiese, Dieter Hess, Detlef Selent, Armin Boerner
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Patent number: 7884253Abstract: 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: GrantFiled: August 25, 2009Date of Patent: February 8, 2011Assignee: Range Fuels, Inc.Inventors: Ronald C. Stites, Jerrod Hohman
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Patent number: 7858831Abstract: 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: GrantFiled: December 19, 2008Date of Patent: December 28, 2010Assignee: The Regents of the University of CaliforniaInventors: Matthew P. Meyer, Hui Zhu
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Patent number: 7842844Abstract: 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: GrantFiled: June 29, 2006Date of Patent: November 30, 2010Assignee: BP Chemicals LimitedInventor: Martin Philip Atkins
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Patent number: 7825286Abstract: 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: GrantFiled: June 6, 2008Date of Patent: November 2, 2010Assignee: T. Hasegawa Co., Ltd.Inventors: Akira Nakanishi, Yasutaka Ohkubo, Naomi Tomita, Tomoko Maeda, Norio Miyazawa
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Patent number: 7799958Abstract: 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: GrantFiled: October 3, 2008Date of Patent: September 21, 2010Assignee: Barclays Bank PLCInventors: Ralf Bonmann, Werner Pompetzki, Markus Weber
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Patent number: 7790938Abstract: 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: GrantFiled: June 6, 2005Date of Patent: September 7, 2010Assignee: Mitsubishi Chemical CorporationInventors: Hiroki Kawasaki, Yuichi Fujita
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Patent number: 7728178Abstract: 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: GrantFiled: August 31, 2006Date of Patent: June 1, 2010Assignee: Sasol Technology (Proprietary) LimitedInventors: Ivan Philip Greager, James Christoffel Crause
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Publication number: 20100130794Abstract: 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: ApplicationFiled: June 6, 2008Publication date: May 27, 2010Inventors: Akira Nakanishi, Yasutaka Ohkubo, Naomi Tomita, Tomoko Maeda, Norio Miyazawa
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Patent number: 7718831Abstract: 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: GrantFiled: February 16, 2006Date of Patent: May 18, 2010Assignee: The Hong Kong Polytechnic UniversityInventors: Albert S Chan, Jianxin Ji, Jing Wu
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Patent number: 7667058Abstract: 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: GrantFiled: May 17, 2002Date of Patent: February 23, 2010Assignee: The Queen's University of BelfastInventors: Kris Anderson, Peter Goodrich, Christopher Hardacre, Sarah Elizabeth Jane McMath
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Patent number: 7652173Abstract: 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: GrantFiled: August 31, 2006Date of Patent: January 26, 2010Assignee: Sasol Technology (Proprietary) LimitedInventor: James Christoffel Crause
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Publication number: 20090270658Abstract: 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: ApplicationFiled: April 24, 2008Publication date: October 29, 2009Inventor: James H. Babler
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Patent number: 7524997Abstract: 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: GrantFiled: July 28, 2006Date of Patent: April 28, 2009Assignee: OXENO Olefinchemie GmbHInventors: Alfred Kaizik, Hans-Gerd Lüken, Michael Grass, Dietrich Maschmeyer, Wilfried Büschken
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Publication number: 20090093656Abstract: 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: ApplicationFiled: October 3, 2008Publication date: April 9, 2009Applicant: INEOS PHENOT GMBH & CO. KGInventors: Ralf Bonmann, Werner Pompetzki, Markus Weber