Aluminum Containing Catalyst Utilized Patents (Class 568/897)
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Patent number: 12187671Abstract: Embodiments of the present disclosure are directed towards methods of etherification including modifying a zeolite catalyst with silica to provide a silica modified zeolite catalyst; and contacting the silica modified zeolite catalyst with an olefin and an alcohol to produce a monoalkyl ether.Type: GrantFiled: September 23, 2020Date of Patent: January 7, 2025Assignee: Dow Global Technologies LLCInventors: Wen-Sheng Lee, Sung-Yu Ku, Stephen W. King
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Patent number: 12012371Abstract: A process can produce alcohols having at least two carbon atoms by catalytic conversion of synthesis gas into a mixture containing alkanes, alkenes, and alcohols. Alkenes are converted into corresponding alcohols in a subsequent step by hydration of the alkanes. Before the hydration and after the catalytic conversion, gas and liquid phases may be separated. Specific catalysts can be employed that have a markedly higher selectivity for alkenes than for alkanes. These catalysts comprise grains of non-graphitic carbon having cobalt nanoparticles dispersed therein. The cobalt nanoparticles have an average diameter dp from 1 to 20 nm, and an average distance D between nanoparticles is from 2 to 150 nm. The combined total mass fraction of metal ? in the grains ranges from 30% to 70% by weight of the total mass of the grains of non-graphitic carbon, wherein 4.5 dp/?>D?0.25 dp/?.Type: GrantFiled: August 14, 2020Date of Patent: June 18, 2024Assignees: thyssenkrupp Uhde GmbH, thyssenkrupp AGInventors: Nils Tenhumberg, Stefan Gehrmann, Michael Kleiber
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Patent number: 11091701Abstract: A process for the production of middle distillates by the catalytically promoted hydration of olefinic compounds having a carbon number ranging from 7 to 14 to convert the olefins to the corresponding mixed alcohols having a higher boiling point that is in the diesel range, the process being conducted in a continuous stirred tank reactor, e.g., an ebullated-bed reactor, utilizing catalysts that include soluble homogeneous acidic compounds and solid heterogeneous compounds such as resins, and amorphous or structured metal oxides containing elements selected from IUPAC Groups 4-10, 13 and 14, and having Lewis or Bronsted acid sites.Type: GrantFiled: January 10, 2019Date of Patent: August 17, 2021Assignee: Saudi Arabian Oil CompanyInventors: Omer Refa Koseoglu, Ali Sawan
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Patent number: 8987530Abstract: 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: GrantFiled: August 7, 2012Date of Patent: March 24, 2015Assignee: Enerkem, Inc.Inventors: Anthony S. Carbone, Stephane Marie-Rose, Esteban Chornet
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Patent number: 8981165Abstract: 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: GrantFiled: August 7, 2012Date of Patent: March 17, 2015Assignee: Enerkem, Inc.Inventors: Anthony S. Carbone, Stephane Marie-Rose, Esteban Chornet
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Patent number: 8865950Abstract: An olefin hydration process and reactor are provided, wherein an integrated membrane selectively removes alcohol product from the reactor, thereby allowing for increased yields.Type: GrantFiled: August 10, 2011Date of Patent: October 21, 2014Assignee: Saudi Arabian Oil CompanyInventors: Ibrahim Abba, Aadesh Harale, Stephan Ralf Vogel, Wei Xu
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Publication number: 20140243563Abstract: The invention relates to a method for the alkylation of residual hydrocarbons obtained from pyrolytic processes, in particular processes for the obtaining of synthesis gas from wet crushed coal, essentially alkene- and alkane-type waste products, in order the exploit the energy thereof in the form of alkenes, alkanes and alcohols having a high energy content. The method is essentially characterised in that the waste products obtained from the synthesis gas formation are subject to a subsequent treatment in order to transform them into other branched alkane-type products and alcoholic compounds, recovering the hydrogen and water produced in said reactions, that remain available for their subsequent use as fuel in other chemical processing plants, or to be fed back to the gasification-pyrolysis process itself, to enrich the synthesis gas obtained.Type: ApplicationFiled: September 1, 2011Publication date: August 28, 2014Applicant: GURADOOR, S.L.Inventor: Daniel Gonzalez Gonzalez
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Patent number: 8779215Abstract: This invention provides a method for producing ethanol and 2-propanol from syngas, the method comprising: (a) converting syngas into methanol using a methanol-synthesis catalyst; (b) converting methanol into ethylene and propylene using a methanol-to-olefins catalyst; and (c) hydrating ethylene into ethanol and propylene into 2-propanol. As taught herein, the combined yield of the ethanol and the 2-propanol from biomass can be at least 100 gallons per dry ton biomass. In certain embodiments, the yield of ethanol is at least 100 gallons per dry ton biomass. In some embodiments, the yield of 2-propanol is at least 50 gallons per dry ton biomass.Type: GrantFiled: December 12, 2012Date of Patent: July 15, 2014Assignee: Maverick Synfuels, Inc.Inventor: Karl Kharas
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Patent number: 8461400Abstract: Methods and systems for the synthesis of alcohol are described herein. The methods and systems include a method of hydrating an olefin that may include emulsifying an olefin gas in a water stream in a high shear device under high shear conditions to produce a dispersion; and contacting the dispersion with a catalyst to hydrate the olefin gas and form an alcohol.Type: GrantFiled: November 6, 2012Date of Patent: June 11, 2013Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory G. Borsinger, Aziz Hassan
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Publication number: 20130102813Abstract: This invention provides a method for producing ethanol and 2-propanol from syngas, the method comprising: (a) converting syngas into methanol using a methanol-synthesis catalyst; (b) converting methanol into ethylene and propylene using a methanol-to-olefins catalyst; and (c) hydrating ethylene into ethanol and propylene into 2-propanol. As taught herein, the combined yield of the ethanol and the 2-propanol from biomass can be at least 100 gallons per dry ton biomass. In certain embodiments, the yield of ethanol is at least 100 gallons per dry ton biomass. In some embodiments, the yield of 2-propanol is at least 50 gallons per dry ton biomass.Type: ApplicationFiled: December 12, 2012Publication date: April 25, 2013Applicant: MAVERICK BIOFUELS, INC.Inventor: Maverick Biofuels, Inc.
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Publication number: 20130066118Abstract: Methods and systems for the synthesis of alcohol are described herein. The methods and systems include a method of hydrating an olefin that may include emulsifying an olefin gas in a water stream in a high shear device under high shear conditions to produce a dispersion; and contacting the dispersion with a catalyst to hydrate the olefin gas and form an alcohol.Type: ApplicationFiled: November 6, 2012Publication date: March 14, 2013Applicant: H R D CorporationInventor: H R D Corporation
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Publication number: 20130041186Abstract: An olefin hydration process and reactor are provided, wherein an integrated membrane selectively removes alcohol product from the reactor, thereby allowing for increased yields.Type: ApplicationFiled: August 10, 2011Publication date: February 14, 2013Applicant: Saudi Arabian Oil CompanyInventors: Ibrahim Abba, Aadesh Harale, Stephan Ralf Vogel, Wei Xu
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Patent number: 8357826Abstract: This invention provides a method for producing ethanol and 2-propanol from syngas, the method comprising: (a) converting syngas into methanol using a methanol-synthesis catalyst; (b) converting methanol into ethylene and propylene using a methanol-to-olefins catalyst; and (c) hydrating ethylene into ethanol and propylene into 2-propanol. As taught herein, the combined yield of the ethanol and the 2-propanol from biomass can be at least 100 gallons per dry ton biomass. In certain embodiments, the yield of ethanol is at least 100 gallons per dry ton biomass. In some embodiments, the yield of 2-propanol is at least 50 gallons per dry ton biomass.Type: GrantFiled: October 15, 2009Date of Patent: January 22, 2013Inventor: Karl Kharas
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Patent number: 8354563Abstract: This invention provides a method for producing ethanol and 2-propanol from syngas, the method comprising: (a) converting syngas into methanol using a methanol-synthesis catalyst; (b) converting methanol into ethylene and propylene using a methanol-to-olefins catalyst; and (c) hydrating ethylene into ethanol and propylene into 2-propanol. As taught herein, the combined yield of the ethanol and the 2-propanol from biomass can be at least 100 gallons per dry ton biomass. In certain embodiments, the yield of ethanol is at least 100 gallons per dry ton biomass. In some embodiments, the yield of 2-propanol is at least 50 gallons per dry ton biomass.Type: GrantFiled: October 15, 2009Date of Patent: January 15, 2013Assignee: Maverick Biofuels, Inc.Inventor: Karl Kharas
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Patent number: 8344188Abstract: This invention provides a method for producing ethanol and 2-propanol from syngas, the method comprising: (a) converting syngas into methanol using a methanol-synthesis catalyst; (b) converting methanol into ethylene and propylene using a methanol-to-olefins catalyst; and (c) hydrating ethylene into ethanol and propylene into 2-propanol. As taught herein, the combined yield of the ethanol and the 2-propanol from biomass can be at least 100 gallons per dry ton biomass. In certain embodiments, the yield of ethanol is at least 100 gallons per dry ton biomass. In some embodiments, the yield of 2-propanol is at least 50 gallons per dry ton biomass.Type: GrantFiled: October 15, 2009Date of Patent: January 1, 2013Assignee: Maverick Biofuels, Inc.Inventor: Karl Kharas
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Patent number: 8329962Abstract: Methods and systems for the synthesis of alcohol are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and solubility of olefins in water. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time. In an embodiment, a method of making an alcohol comprises introducing an olefin into a water stream to form a gas-liquid stream. The method further comprises flowing the gas-liquid stream through a high shear device so as to form a dispersion with gas bubbles having a mean diameter less than about 1 micron. In addition, the method comprises contacting the gas-liquid stream with a catalyst in a reactor to hydrate the olefin gas and form an alcohol.Type: GrantFiled: May 15, 2012Date of Patent: December 11, 2012Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 8217205Abstract: Methods and systems for the synthesis of alcohol are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and solubility of olefins in water. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time. In an embodiment, a method of making an alcohol comprises introducing an olefin into a water stream to form a gas-liquid stream. The method further comprises flowing the gas-liquid stream through a high shear device so as to form a dispersion with gas bubbles having a mean diameter less than about 1 micron. In addition, the method comprises contacting the gas-liquid stream with a catalyst in a reactor to hydrate the olefin gas and form an alcohol.Type: GrantFiled: February 15, 2011Date of Patent: July 10, 2012Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 7910068Abstract: Methods and systems for the synthesis of alcohol are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and solubility of olefins in water. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time. In an embodiment, a method of making an alcohol comprises introducing an olefin into a water stream to form a gas-liquid stream. The method further comprises flowing the gas-liquid stream through a high shear device so as to form a dispersion with gas bubbles having a mean diameter less than about 1 micron. In addition, the method comprises contacting the gas-liquid stream with a catalyst in a reactor to hydrate the olefin gas and form an alcohol.Type: GrantFiled: December 15, 2008Date of Patent: March 22, 2011Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20100099926Abstract: This invention provides a method for producing ethanol and 2-propanol from syngas, the method comprising: (a) converting syngas into methanol using a methanol-synthesis catalyst; (b) converting methanol into ethylene and propylene using a methanol-to-olefins catalyst; and (c) hydrating ethylene into ethanol and propylene into 2-propanol. As taught herein, the combined yield of the ethanol and the 2-propanol from biomass can be at least 100 gallons per dry ton biomass. In certain embodiments, the yield of ethanol is at least 100 gallons per dry ton biomass. In some embodiments, the yield of 2-propanol is at least 50 gallons per dry ton biomass.Type: ApplicationFiled: October 15, 2009Publication date: April 22, 2010Applicant: Range Fuels, Inc.Inventor: Karl KHARAS
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Publication number: 20100099925Abstract: This invention provides a method for producing ethanol and 2-propanol from syngas, the method comprising: (a) converting syngas into methanol using a methanol-synthesis catalyst; (b) converting methanol into ethylene and propylene using a methanol-to-olefins catalyst; and (c) hydrating ethylene into ethanol and propylene into 2-propanol. As taught herein, the combined yield of the ethanol and the 2-propanol from biomass can be at least 100 gallons per dry ton biomass. In certain embodiments, the yield of ethanol is at least 100 gallons per dry ton biomass. In some embodiments, the yield of 2-propanol is at least 50 gallons per dry ton biomass.Type: ApplicationFiled: October 15, 2009Publication date: April 22, 2010Applicant: Range Fuels, Inc.Inventor: Karl KHARAS
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Publication number: 20100099927Abstract: This invention provides a method for producing ethanol and 2-propanol from syngas, the method comprising: (a) converting syngas into methanol using a methanol-synthesis catalyst; (b) converting methanol into ethylene and propylene using a methanol-to-olefins catalyst; and (c) hydrating ethylene into ethanol and propylene into 2-propanol. As taught herein, the combined yield of the ethanol and the 2-propanol from biomass can be at least 100 gallons per dry ton biomass. In certain embodiments, the yield of ethanol is at least 100 gallons per dry ton biomass. In some embodiments, the yield of 2-propanol is at least 50 gallons per dry ton biomass.Type: ApplicationFiled: October 15, 2009Publication date: April 22, 2010Applicant: Range Fueis, Inc.Inventor: Karl KHARAS
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Patent number: 7482497Abstract: Methods and systems for the synthesis of alcohol are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and solubility of olefins in water. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time. In an embodiment, a method of making an alcohol comprises introducing an olefin into a water stream to form a gas-liquid stream. The method further comprises flowing the gas-liquid stream through a high shear device so as to form a dispersion with gas bubbles having a mean diameter less than about 1 micron. In addition, the method comprises contacting the gas-liquid stream with a catalyst in a reactor to hydrate the olefin gas and form an alcohol.Type: GrantFiled: June 20, 2008Date of Patent: January 27, 2009Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20080033218Abstract: This invention is directed to a process for making alcohol from syngas, and a process for making olefin, as well as polyolefin, from the alcohol. The syngas is converted to a mixed alcohol stream using a catalyst comprising at least one oxide component. Upon contacting the catalyst with a desired syngas composition, a preferred mixed alcohol product is formed. Preferably, the syngas composition has a stoichiometric molar ratio of less than 2.Type: ApplicationFiled: June 20, 2007Publication date: February 7, 2008Inventors: James R. Lattner, Matthew James Vincent, Kun Wang, Michel Molinier, Michael J. Veraa, Anthony F. Volpe, Hailian Li, Jeffrey C. Yoder, Mark Muraoka
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Patent number: 7235702Abstract: The invention disclosed relates to the production of alcohols. A first aspect of the invention relates to a process for production of alcohols, and in particular to a process for the catalytic hydration of an olefin to the corresponding alcohol in substantially anhydrous form, under selected mild reaction conditions, and using a selected catalyst. A second aspect of the invention relates to a process for dehydration of an azeotropic mixture, including a first alcohol and water. A hydration reaction between the water in the azeotropic mixture and an added olefin, under selected mild conditions, and using a selected catalyst, produces a product including a second alcohol corresponding to the olefin, and the first alcohol, in substantially anhydrous form.Type: GrantFiled: March 12, 2004Date of Patent: June 26, 2007Assignee: Governors of the University of AlbertaInventors: Karl T. Chuang, Yung F. Chen
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Patent number: 7179948Abstract: The invention relates to a process for preparing tert-butanol by reaction of a homogeneous mixture comprising water, tert-butanol and an isobutene-containing hydrocarbon mixture over an acidic ion-exchange resin at from 30 to 120° C., wherein the homogeneous mixture contains, at a proportion by mass of isobutene of above 10%, from 30 to 80% of the maximum amount of water made possible by the solubility of water in the mixture of tert-butanol and the isobutene-containing hydrocarbon mixture.Type: GrantFiled: December 19, 2003Date of Patent: February 20, 2007Assignee: Oxeno Olefinchemie GmbHInventors: Bernhard Scholz, Franz Nierlich, Dieter Reusch, Silvia Santiago Fernandez, Andreas Beckmann, Wilfried Bueschken, Alfred Kaizik
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Patent number: 7148387Abstract: Discloses a process for efficiently producing a hydroxyl group containing compound with a simple apparatus and simple procedures using a very small amount of a catalyst, which process reduces a catalyst recovering step and a catalyst neutralization step vastly and does not require catalyst regeneration and catalyst exchange. The process for producing a hydroxyl group containing compound comprises allowing an aqueous solution containing 1 ppb to 500 ppm of an acid catalyst to react with an aliphatic double bond having compound in a molar ratio (water/aliphatic double bond having compound) of water to aliphatic double bond having compound of from 1 to 50, at a reaction temperature of from 200 to 600° C. under a reaction pressure of from 1 to 100 MPa and thereby conducting hydration reaction of the aliphatic double bond containing compound with water.Type: GrantFiled: May 27, 2004Date of Patent: December 12, 2006Assignees: Mitsui Chemicals, Inc., National Institute of Advanced Industrial Science and TechnologyInventors: Kenta Takahashi, Yutaka Ikushima
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Patent number: 7115787Abstract: The invention relates to a process for preparing tert-butanol (TBA) from isobutene-containing mixtures, in which at least part of the conversion is achieved with the aid of a reactive rectification.Type: GrantFiled: November 11, 2003Date of Patent: October 3, 2006Assignee: OXENO Olefinchemie GmbHInventors: Dieter Reusch, Andreas Beckmann, Franz Nierlich, Axel Tuchlenski
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Patent number: 7026519Abstract: The invention relates to a process for preparing tert-butanol (TBA) by reacting isobutene-containing hydrocarbon mixtures with water over acidic solid catalysts in a plurality of reactors, wherein the conversion is increased upstream of the last reactor by removing a portion of the TBA present in the reaction mixture.Type: GrantFiled: July 19, 2004Date of Patent: April 11, 2006Assignee: Oxeno Olefinchemie GmbHInventors: Silvia Santiago Fernandez, Andreas Beckmann, Franz Nierlich, Dieter Reusch
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Patent number: 7002050Abstract: The present invention relates to a process for preparing tert-butanol (TBA) by reacting an isobutene-containing hydrocarbon mixture with water over a solid acid catalyst in a reactor cascade, wherein at least one reactor is supplied alternately with two different isobutene-containing hydrocarbon mixtures, of which one has both a higher tert-butanol content and a higher water content than the other mixture.Type: GrantFiled: March 24, 2005Date of Patent: February 21, 2006Assignee: Oxeno Olefinchemie GmbHInventors: Silvia Santiago Fernandez, Jörg Sauer, Guido Stochniol, Dietrich Maschmeyer, Wilfried Büschken, Klaus-Diether Wiese
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Patent number: 6951967Abstract: Tertiary alcohols can be prepared by the hydration of tertiary olefins having the same number of carbon atoms on an acidic ion exchanger using special structured multi-purpose packings for heterogeneous reactive rectification. An excellent yield and purity of the alcohol and an extended service life of the catalyst are achieved.Type: GrantFiled: February 13, 2003Date of Patent: October 4, 2005Assignees: EC Erdolchemie GmbH, Bayer AGInventors: Axel Gohrt, Joachim Grub, Stefan Kaminsky, Stephan Muller, Brian Schwegler
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Patent number: 6906229Abstract: The invention relates to the production of isopropyl alcohol from di-isopropyl ether by catalytic distillation. The process solves, in particular, problems associated with the Sulfuric Acid Process.Type: GrantFiled: February 29, 2000Date of Patent: June 14, 2005Assignee: ExxonMobil Chemical Patents, Inc.Inventor: Paul E. Burton
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Publication number: 20040210072Abstract: Higher trialkylaluminum compounds may be made by forming &agr;-olefin by oligomerizing ethylene using a transition metal containing catalyst, reacting the &agr;-olefins formed with a lower trialkylaluminum compound to form higher trialkylaluminum compound(s). These may optionally be oxidized, as with oxygen, to form higher trialkoxyaluminum compound, which in turn may be hydrolyzed to &agr;-alcohols. In one variation of the process lower &agr;-olefins and higher (relatively) &agr;-alcohols may be formed and isolated. Higher trialkylaluminum compounds and &agr;-alcohols are useful as chemical intermediates, while lower &agr;-olefins are useful as monomers for polyolefins.Type: ApplicationFiled: April 28, 2004Publication date: October 21, 2004Inventor: Joel David Citron
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Publication number: 20040210073Abstract: Higher trialkylaluminum compounds may be made by forming &agr;-olefin by oligomerizing ethylene using a transition metal containing catalyst, reacting the &agr;-olefins formed with aluminum and hydrogen to form higher trialkylaluminum compounds. These may optionally be oxidized, as with oxygen, to form higher trialkoxyaluminum compound, which in turn may be hydrolyzed to &agr;-alcohols. Higher trialkylaluminum compounds and &agr;-alcohols are useful as chemical intermediates.Type: ApplicationFiled: April 28, 2004Publication date: October 21, 2004Inventor: Joel David Citron
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Patent number: 6723886Abstract: An apparatus and method is disclosed for producing alcohols, particularly methanol, according to an alcohol synthesis process. The apparatus comprises a catalytic distillation reactor where reactants are fed into the catalytic distillation reactor to undergo catalytic reaction to form methanol. Methanol production beyond the thermodynamic limit is achieved in the apparatus through use of multiple distillation stages, preferably at least three.Type: GrantFiled: May 16, 2002Date of Patent: April 20, 2004Assignee: ConocoPhillips CompanyInventors: Joe D. Allison, Harold A. Wright, Todd H. Harkins, Doug S. Jack
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Patent number: 6002037Abstract: The present invention describes the Zr-catalyzed asymmetric carboalumination of alkenes to produce chiral alkylalanes that can be converted to various chiral organic compounds, such as isoalkyl alcohols, in highly enantiomeric excess. More particularly, the asymmetric addition of alkylaluminums to terminal alkenes under the influence of a catalyst such as a chiral zirconocene derivative produces chiral alkylaluminums that can be oxidized to 2-alkyl-substituted products (particularly alcohols) in greater than 60% enantiomeric excess. The ee figures can often exceed 95%. The organoalanes produces by the inventive process can be converted to a wide variety of other organic compounds of interest in the production of vitamins, pharmaceuticals and other medicinally and biologically important compounds, including vitamins and antibiotics.Type: GrantFiled: October 14, 1997Date of Patent: December 14, 1999Assignee: Purdue Research FoundationInventors: Ei-ichi Negishi, Denis Y. Kondakov
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Patent number: 5780688Abstract: The invention concerns a supported catalyst in the form of packing and constructed on an open-pore support material on whose external and internal surfaces a macro-porous ion exchange resin is mechanically and/or chemically affixed.Type: GrantFiled: April 5, 1996Date of Patent: July 14, 1998Assignee: Veba Oel AGInventors: Ulrich Hoffmann, Ulrich Kunz, Hartmut Bruderreck, Klaus Gottlieb, Kuno Schadlich, Stefan Becker
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Patent number: 5731480Abstract: A process is described for coproducing vinylidene alcohol and vinylidene olefin. The process involves dimerizing one or more vinylolefins with an alkyl aluminum catalyst to form a first product mixture comprising at least vinylidene olefin and alkyl aluminum compound. The vinylidene olefin is then reacted with the alkyl aluminum compound under displacement conditions to form 1-olefin while concurrently removing the 1-olefin from the displacement reaction mixture to form a second product mixture comprising at least beta-branched alkyl aluminum compound. The second product mixture is treated with air or oxygen under mild oxidation conditions to form a third product mixture comprising at least beta-branched aluminum alkoxide. The beta-branched aluminum alkoxide is then hydrolyzed to form vinylidene alcohol. The process makes effective use of the alkyl aluminum catalyst both as a catalyst and as a reactant, and requires only a relatively small amount of reaction equipment.Type: GrantFiled: November 3, 1995Date of Patent: March 24, 1998Assignee: Albemarle CorporationInventor: Kaung-Far Lin
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Patent number: 5569789Abstract: A multistaged fixed catalyst bed process for the production of diisopropyl ether and isopropanol is disclosed comprising a fixed bed of serially connected stages containing zeolite Beta catalyst. A feedstream of propylene and water equivalents selected from the group consisting of water, isopropanol and diisopropyl ether is introduced into each stage at a rate sufficient to provide a mole ratio of water equivalents to propylene equivalents that increases in increments by stage from at least 0.1 in a first stage to at most 1.2 in a final stage. The feedstream is introduced at a temperature between 50.degree. and 450.degree. C., pressure between 700 and 24000 kPa, and weight hourly space velocity between 0.10 and 30, based on catalyst, whereby a single non-aqueous liquid phase is maintained in the fixed bed. An effluent product stream is recovered comprising diisopropyl ether, isopropanol and water from the final stage. Isopropanol is recycled to the first stage when the preferred product is diisopropyl ether.Type: GrantFiled: August 2, 1995Date of Patent: October 29, 1996Assignee: Mobil Oil CorporationInventors: Weldon K. Bell, Stephen H. Brown, Jeffrey C. Trewella
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Patent number: 5504259Abstract: A process for conversion of a feedstock selected from the group consisting of biomass and refuse derived fuel (RDF) to provide reformulated gasoline components comprising a substantial amount of materials selected from the group consisting of ethers, alcohols, or mixtures thereof, comprising: drying said feedstock; subjecting said dried feedstock to fast pyrolysis using a vortex reactor or other means; catalytically cracking vapors resulting from said pyrolysis using a zeolite catalyst; condensing any aromatic byproduct fraction; catalytically alkylating any benzene present in said vapors after condensation; catalytically oligomerizing any remaining ethylene and propylene to higher olefins; isomerizing said olefins to reactive iso-olefins; and catalytically reacting said iso-olefins with an alcohol to form ethers or with water to form alcohols.Type: GrantFiled: October 29, 1992Date of Patent: April 2, 1996Assignee: Midwest Research InstituteInventors: James P. Diebold, John W. Scahill, Helena L. Chum, Robert J. Evans, Bahman Rejai, Richard L. Bain, Ralph P. Overend
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Patent number: 5488186Abstract: A process is presented for the hydration of light olefins to produce C.sub.2 -C.sub.7 aliphatic alcohols with improved selectivity, catalyst productivity and catalyst stability. Acidic medium pore, shape selective metallosilicate catalyst particles are contacted with a feedstream containing light olefin plus water at elevated temperature above the dew point of water, i.e., in a gas phase, wherein the reaction mixture is essentially starved with respect to the mole ratio of water to C.sub.2 -C.sub.7 light olefin. Isopropanol is produced at a selectivity greater than 70 weight percent when the mole ration of water to propylene is between 0.05 and 0.499. Zeolite ZSM-5, ZSM-23, ZSM-35 and ferrierite are preferred catalysts.Type: GrantFiled: March 22, 1995Date of Patent: January 30, 1996Assignee: Mobil Oil CorporationInventors: Stephen H. Brown, Jeffrey C. Trewella
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Patent number: 5488185Abstract: An ethene stream which contains ethane as an impurity or a propene stream which contains propane as an impurity is hydrated with water vapor in the presence of a hydration catalyst to produce ethanol or isopropanol, respectively. After removal of the alcohol the gaseous product stream is subjected to adsorption, thereby producing an ethene-enriched stream or a propene-enriched stream. The ethene-enriched stream or the propene-enriched stream is recycled to the hydration reactor.Type: GrantFiled: April 22, 1994Date of Patent: January 30, 1996Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Loc H. Dao
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Patent number: 5405814Abstract: An olefin hydration catalyst is regenerated with a non-oxidizing light gas, such as hydrogen. Light olefins, especially propylene, are converted to a mixture of alcohol(s), such as isopropanol (IPA) and ether(s), such as diisopropylether (DIPE) by contacting a feed containing the olefin with water and/or alcohol with the olefin hydration catalyst. Regeneration conditions include temperatures of from about 150.degree. C. to about 550.degree. C., pressures below about 1000 psig (6900 kPa). Lower pressures of regeneration unexpectedly demonstrated more effective catalyst regeneration through greater coke removal.Type: GrantFiled: June 7, 1993Date of Patent: April 11, 1995Assignee: Mobil Oil CorporationInventors: James H. Beech, Jr., Weldon K. Bell, W. Thomas Mo, Hye Kyung C. Timken, Robert A. Ware
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Patent number: 5371301Abstract: In a single stage process for producing diisopropyl ether, SO.sub.3 from a DIPE reactor effluent is transferred to an aqueous phase in a liquid extraction zone and removed from the aqueous phase using a basic ion exchange resin disposed in an SO.sub.3 removal zone. As a consequence, DIPE reactor effluent can be returned to the DIPE reactor to serve as a solvent and to assist in providing cooling to the DIPE reactor without causing catalyst deactivation.Type: GrantFiled: June 21, 1993Date of Patent: December 6, 1994Assignee: UOPInventors: Terry L. Marker, Laura E. Kempf
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Patent number: 5349110Abstract: Disclosed is a process for preparation of monoalkyl ethers by reacting low molecular weight olefins and the corresponding oxiranes, in the presence of a catalyst comprising an acidic heterogeneous or homogeneous catalyst, generally represented by the equation: ##STR1## where R, R', R" may be hydrogen or an alkyl radical.Type: GrantFiled: August 2, 1993Date of Patent: September 20, 1994Assignee: Texaco Chemical CompanyInventor: John F. Knifton
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Patent number: 5324865Abstract: A process for production of diisopropyl ether by conversion of hydrocarbon feedstock containing propene, propane and C.sub.2 - light gas components, including the steps of: optionally, prefractionating fresh feedstock containing propene, propane and C.sub.2 - light gas components to provide a reactor feedstream rich in propene; contacting the feedstock and water in a catalytic reactor with acidic catalyst under olefin hydration and etherification conditions; and recovering from the catalytic reactor a liquid reactor effluent stream containing diisopropyl ether, isopropanol, water, unreacted propene, propane and C.sub.2 - light gas components. Improved operation is achieved by separating the liquid effluent stream in a vertical stripper column; recovering an overhead vapor stream containing propene, propane and C.sub.2 - light gas components from the stripper column; cooling the overhead vapor stream to provide a reflux stream rich in condensed propene and propane; removing the C.sub.Type: GrantFiled: February 22, 1993Date of Patent: June 28, 1994Assignee: Mobil Oil CorporationInventors: James H. Beech, Jr., Douglas Miller, Jorge L. Soto, James A. Stoos, Albert H. Wu
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Patent number: 5324866Abstract: The present invention is an integrated isopropyl alcohol (IPA) and diisopropyl ether (DIPE) process. In this process, IPA, substantially free of DIPE, is formed in a hydration reactor by reacting an olefinic feedstock with water in a hydration reactor. The effluent from the hydration reactor is then contacted in a first separation unit with DIPE which was made in an etherification reactor. The resulting mixture is then passed to a second separation unit to separate the IPA from the DIPE product. The IPA is then fed to the etherification reactor to produce DIPE.Type: GrantFiled: March 23, 1993Date of Patent: June 28, 1994Assignee: UOPInventors: Terry L. Marker, Laura E. Kempf
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Patent number: 5288924Abstract: A method for starting up a fixed bed propylene hydration reactor containing shape selective metallosilicate catalyst particles for the production of isopropanol and/or diisopropyl ether is disclosed comprising the following sequential steps: contacting a feedstream comprising propane with catalyst particles in a hydration reactor; then introducing a feedstream comprising isopropanol into the reactor to displace propane. Next, a feedstream comprising propylene is introduced into the reactor under etherification conditions. Finally, a feedstream is introduced in the reactor comprising water under etherification and hydration reaction conditions whereby diisopropyl ether and isopropanol are produced.Type: GrantFiled: September 18, 1992Date of Patent: February 22, 1994Assignee: Mobil Oil CorporationInventors: James H. Beech, Jr., Charles M. Sorensen, James A. Stoos, Robert A. Ware
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Patent number: 5233101Abstract: An improvement in iso-olefin hydration is obtained in an integrated process combining a fluidized catalytic cracking reaction and a fluidized catalyst hydration reaction wherein zeolite catalyst particles are withdrawn in partially deactivated form from the alkanol reaction stage and added as part of the catalyst in the FCC reaction.Type: GrantFiled: October 9, 1992Date of Patent: August 3, 1993Assignee: Mobil Oil CorporationInventor: Mohsen N. Harandi
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Patent number: 5171470Abstract: A bifunctional optically active liquid crystal intermediate compound represented by the following Formula (I): X--Y--C.sub.* H(M)--CH.sub.2 --OH is disclosed, wherein X represents CH.sub.2 .dbd.CH--, HOCH.sub.2 --CH.sub.2 --, HSCH.sub.2 --CH.sub.2 --, HOCH.sub.2 --, HOOC--, HOCH.sub.2 CH.dbd.CH--, CH.sub.3 CH(OH)-- or HOCH.sub.2 C.sub.* H(Z)--; Y represents --CH.sub.2).sub.n or --CH.sub.2 (.sub.m O).sub.l CH.sub.2 --, where n represents an integer of 1 to 18, m represents an integer of 1 to 12, and l represents an integer of 1 to 4; M and Z each represents halogen atom, an alkyl group or an alkoxy group, said halogen atom being selected from the group consisting of I, Cl, Br and F, and said alkyl group or alkoxy group having 1 to 8 carbon atoms; and the mark * represents an asymmetric carbon atom. A process for preparing the intermediate compound is also disclosed.Type: GrantFiled: August 7, 1990Date of Patent: December 15, 1992Assignees: Canon Kabushiki Kaisha, Hiroyuki NohiraInventors: Hiroyuki Nohira, Takahiro Ishizuka, Kazuo Yoshinaga
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Patent number: 5162591Abstract: A process for production of dialkyl ether by hydration and etherification of olefinic feedstock containing at least one lower alkene by contacting the olefinic feedstock and water in a catalytic reaction zone with porous solid metallosilicate acidic catalyst under olefin hydration and etherification conditions. Improvement is achieved by recovering a first fluid effluent stream from the reaction zone; splitting the first fluid effluent stream into a liquid product recovery stream and a fluid recycle stream; and passing the fluid recycle stream consisting essentially of olefin, alcohol and ether in effluent stream proportions for feeding to the reaction zone along with fresh olefinic feedstock and fresh water, wherein the amount of fluid recycle stream is sufficient to maintain a homogeneous single fluid reaction phase in the reaction zone.Type: GrantFiled: July 25, 1990Date of Patent: November 10, 1992Assignee: Mobil Oil CorporationInventors: James H. Beech, Jr., James A. Stoos, Francis P. Ragonese