Sulfur Containing Catalyst Utilized Patents (Class 568/899)
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Patent number: 9636651Abstract: The present invention relates to a plant for performance of heterogeneously catalyzed gas phase reactions. The plant entails a reactor, at least one line leading into the reactor for introduction of reactants into the reactor, at least one first feed for providing at least one first reactant A, which leads into the line, at least one second feed for providing at least one second reactant B, which leads into the line, at least one third feed for providing a cycle gas G, which leads into the line, a temperature control unit which is disposed in the line upstream of the reactor and is for controlling the temperature of the first reactant A and/or second reactant B and/or cycle gas G prior to entry into the reactor and at least one outlet for products, by-products and/or unreacted reactants from the gas phase reaction.Type: GrantFiled: June 11, 2015Date of Patent: May 2, 2017Assignee: BASF SEInventors: Ulrich Hammon, Thomas Walter
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Patent number: 9593059Abstract: Mixed butenes from a cracking process, or raffmates of MTBE or tert-butyl alcohol (TBA), are simultaneously hydrated using water in the presence of a catalyst to produce sec-butyl alcohol (SBA) and tert-butyl alcohol as the principal products, the mixed butanols having utility as fuel additives, e.g., as oxygenates and octane enhancers to replace MTBE, and as a neat fuel.Type: GrantFiled: January 9, 2012Date of Patent: March 14, 2017Assignee: SAUDI ARABIAN OIL COMPANYInventors: Wei Xu, Farhan M. Al-Shahrani, Abdennour Bourane, Stephan Ralf Vogel
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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: 8921619Abstract: A membrane-integrated hydration reactor that is operable to produce an associated alcohol product from an olefin using water includes a solid acid olefin hydration catalyst in a production zone and a hydrophilic membrane operable to selectively permit pervaporation of water one-way and not permit pervaporation of the associated alcohol or permeation of the olefin at olefin hydration process conditions in a separations zone. The production zone is operable to form a production zone product mixture made of the associated alcohol and any unreacted water. The associated separations zone is operable to form and produce both the associated alcohol product and a pervaporated water product from the production zone product mixture. A method of olefin hydration for forming an associated alcohol product from an olefin using water uses the membrane-integrated hydration reactor at olefin hydration process conditions.Type: GrantFiled: December 5, 2012Date of Patent: December 30, 2014Assignee: Saudi Arabian Oil CompanyInventors: Aadesh Harale, Wei Xu, Ibrahim Abba
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Publication number: 20140357890Abstract: A method for efficiently producing t-butanol as a raw material of a methacrylic resin from isobutanol is described, including a step (1) of dehydrating isobutanol to obtain butenes, and a step (2) of hydrating the butenes to obtain t-butanol. A method for producing methacrolein and methacrylic acid is also described, which further includes a step (3) of dehydrating and oxidizing the obtained t-butanol to obtain methacrolein and methacrylic acid. An apparatus for performing the steps (1) to (3) is also described.Type: ApplicationFiled: November 6, 2012Publication date: December 4, 2014Applicant: MITSUBISHI RAYON CO., LTD.Inventors: Ken Ooyachi, Toshiya Yasukawa, Shuji Akihara
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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: 20140039226Abstract: Mixed butenes from a cracking process, or raffmates of MTBE or tert-butyl alcohol (TBA), are simultaneously hydrated using water in the presence of a catalyst to produce sec-butyl alcohol (SBA) and ter-butyl alcohol as the principal products, the mixed butanols having utility as fuel additives, e.g., as oxygenates and octane enhancers to replace MTBE, and as a neat fuel.Type: ApplicationFiled: January 9, 2012Publication date: February 6, 2014Applicant: SAUDI ARABIAN OIL COMPANYInventors: Wei Xu, Farhan M. Al-Shahrani, Abdennour Bourane, Stephan Ralf Vogel
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Patent number: 8637716Abstract: An object of the present invention is to provide, for the production of isobutene, a high-yielding, highly-selective, and long-term stable production process of isobutene from TBA. With respect to the production of TBA, an object of the present invention is to provide a TBA production process in which, through long-term stable maintenance of a high reaction activity, long-term continuous operation is enabled and the productivity is improved. The present invention discloses a process for producing isobutene that employs a dehydration temperature of from 200 to 450° C. in use of an alumina catalyst that contains a Na content of 0.6% by weight or less in terms of NaO2 and a Na content of 0.4% by weight in terms of NaO2, and has a specific surface area of from 200 to 600 m2/g.Type: GrantFiled: October 25, 2006Date of Patent: January 28, 2014Assignee: Asahi Kasei Chemicals CorporationInventors: Tatsuo Yamaguchi, Hiroyuki Noda, Toru Watanabe, Shumya Kirino
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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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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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Patent number: 8288595Abstract: Embodiments of the invention disclosed herein relate to a process for the production of a C6-C15 alcohol mixture comprising the steps of: hydroformylating an olefin mixture comprising a branched C5-C14 olefin to form a hydroformylation product comprising aldehydes and formate esters, whereby the hydroformylation product has a net cold sap number from 15 to 38 mg KOH/g, and converting the aldehydes and formate esters to alcohols in a hydrogenation step comprising at least one first hydrogenation reactor comprising a fixed bed of a heterogeneous sulphided bimetallic catalyst.Type: GrantFiled: February 21, 2012Date of Patent: October 16, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Eddy Van Driessche, Jean-Jacques G. Muls, Arie Van Vliet, Carl R. Beck, Charles M. Yarbrough
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Publication number: 20120232313Abstract: 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: ApplicationFiled: May 15, 2012Publication date: September 13, 2012Applicant: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20120149935Abstract: Embodiments of the invention disclosed herein relate to a process for the production of a C6-C15 alcohol mixture comprising the steps of: hydroformylating an olefin mixture comprising a branched C5-C14 olefin to form a hydroformylation product comprising aldehydes and formate esters, whereby the hydroformylation product has a net cold sap number from 15 to 38 mg KOH/g, and converting the aldehydes and formate esters to alcohols in a hydrogenation step comprising at least one first hydrogenation reactor comprising a fixed bed of a heterogeneous sulphided bimetallic catalyst.Type: ApplicationFiled: February 21, 2012Publication date: June 14, 2012Inventors: Eddy Van Driessche, Jean-Jacques G. Muls, Arie Van Vliet, Carl R. Beck, Charles M. Yarbrough
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Patent number: 8143459Abstract: Oxo-alcohols in the plasticizer range typically contain small amounts of methyl esters having the same alkyl chain as the alcohol itself. These methyl esters are causing product quality problems and environmental problems because of transesterification in the esterification process where the plasticizer ester derivatives are produced. A process using controlled oxonation and hydrogenation conditions is disclosed for the production of alcohols containing low amounts of methyl esters. Plasticizer esters with low amounts of aliphatic di-alkyl esters are also disclosed.Type: GrantFiled: April 26, 2010Date of Patent: March 27, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Eddy Van Driessche, Jean-Jacques G. Muls, Arie Van Vliet, Carl R. Beck, Charles M. Yarbrough
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Publication number: 20110251441Abstract: 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: ApplicationFiled: February 15, 2011Publication date: October 13, 2011Applicant: H R D CORPORATIONInventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
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Publication number: 20100312005Abstract: Oxo-alcohols in the plasticiser range typically contain small amounts of methyl esters having the same alkyl chain as the alcohol itself. These methyl esters are causing product quality problems and environmental problems because of transesterification in the esterification process where the plasticiser ester derivatives are produced. A process using controlled oxonation and hydrogenation conditions is disclosed for the production of alcohols containing low amounts of methyl esters. Plasticiser esters with low amounts of aliphatic di-alkyl esters are also disclosed.Type: ApplicationFiled: April 26, 2010Publication date: December 9, 2010Inventors: Eddy Van Driessche, Jean-Jacques G. Muls, Arie Van Vliet, Carl R. Beck, Charles M. Yarbrough
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Patent number: 7795376Abstract: A method of isolating a PHA, includes combining the PHA, a first solvent and a second solvent to form a combination, the first solvent being capable of forming an azeotrope with the second solvent; and heating the combination to form the azeotrope of the first and second solvents.Type: GrantFiled: July 2, 2009Date of Patent: September 14, 2010Assignee: Metabolix Inc.Inventors: Johan Van Walsem, Erik Anderson, John Licata
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Patent number: 7622618Abstract: A novel olefin hydration method is provided for efficiently producing alcohols by hydration of olefins containing 2 to 5 carbon atoms in the presence of a catalyst. Thus, alcohols are produced by hydrating olefins containing 2 to 5 carbon atoms at reaction temperature of 100 to 250° C. in the presence of a solid acid catalyst consisting of carbonaceous materials containing sulfonic acid groups obtained from an organic matter by carbonization and sulfonation. In carrying out this method, the organic matter is preferably an aromatic hydrocarbon or a saccharide, the olefin is preferably propylene or a butenes, and the hydration reaction temperature is not lower than 120° C., more preferably not lower than 150° C.Type: GrantFiled: November 30, 2006Date of Patent: November 24, 2009Assignees: Nippon Oil Corporation, Tokyo Institute of TechnologyInventors: Shinichiro Yanagawa, Michikazu Hara
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Publication number: 20090137850Abstract: A novel olefin hydration method is provided for efficiently producing alcohols by hydration of olefins containing 2 to 5 carbon atoms in the presence of a catalyst. Thus, alcohols are produced by hydrating olefins containing 2 to 5 carbon atoms at reaction temperature of 100 to 250° C. in the presence of a solid acid catalyst consisting of carbonaceous materials containing sulfonic acid groups obtained from an organic matter by carbonization and sulfonation. In carrying out this method, the organic matter is preferably an aromatic hydrocarbon or a saccharide, the olefin is preferably propylene or a butenes, and the hydration reaction temperature is not lower than 120° C., more preferably not lower than 150° C.Type: ApplicationFiled: November 30, 2006Publication date: May 28, 2009Applicants: Nippon Oil Corporation, Tokyo Institute of TechnologyInventors: Shinichiro Yanagawa, Michikazu Hara
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Patent number: 7488837Abstract: The present invention relates to a process for preparing an alkyl ester of a fatty acid, including the steps of carrying out an esterification reaction between a free fatty acid contained in a fat or oil and an alcohol; carrying out a transesterification reaction between a fat or oil and an alcohol; and refining an alkyl ester of a fatty acid, wherein at least any one of three steps is carried out in a corresponding step selected from the steps of (a) contacting a fat or oil and an alcohol with a resin foamed article to which a catalyst containing fine strongly acidic particles is supported or a resin foamed article modified to be strongly acidic, and carrying out an esterification reaction between a free fatty acid in the fat or oil and the alcohol; (b) contacting a fat or oil and an alcohol with a resin foamed article to which a catalyst containing fine alkali particles is supported, and carrying out a transesterification reaction between the fat or oil and the alcohol; and (c) contacting a reaction mixtureType: GrantFiled: June 28, 2005Date of Patent: February 10, 2009Assignee: Revo International Inc.Inventors: Keiichi Tsuto, Tetsuya Koshikawa
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Publication number: 20090005613Abstract: 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: ApplicationFiled: June 20, 2008Publication date: January 1, 2009Applicant: H R D CORPORATIONInventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
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Patent number: 7399891Abstract: This invention relates to a process for the production of an alcohol, the process comprising (a) reacting an olefin and water in the presence of a catalyst under conditions sufficient to form a crude alcohol stream comprising alcohol, and a dialkyl ether; (b) separating at least a portion of the crude alcohol stream into an alcohol-containing stream and a dialkyl ether stream; (c) contacting at least a portion of the dialkyl ether stream with an ether decomposition catalyst, the ether decomposition catalyst comprising a mixed metal oxide having the following composition XmYnZpOq where X is at least one metal selected from Group 4 of the Periodic Table of Elements, Y is at least one metal selected from Group 3 (including the Lanthanides and Actinides) and Group 6 of the Periodic Table of Elements and Z is at least one metal selected from Groups 7, 8, and 11 of the Periodic Table of Elements; m, n, p, and q are the atomic ratios of their respective components and, when m is 1, n is from about 0.01 to about 0.Type: GrantFiled: June 8, 2005Date of Patent: July 15, 2008Assignee: ExxonMobil Chemical Patents Inc.Inventors: Charles M Yarbrough, Brian William Roberts, Dennis Jay Davoren, Kenneth Joseph Buturla, Carl Stotz Katzenstein, Doron Levin, Hans Georg Korsten, Vijay Swarup
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Patent number: 7211702Abstract: 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: November 13, 2003Date of Patent: May 1, 2007Assignee: The 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: 7034193Abstract: A method for purifying a spent acid catalyst from an acid catalyzed chemical reaction that generates a mixture of a product, spent add and tar, includes the steps of separating the mixture of product, spent acid, and tar into a product fraction and a spent acid fraction, said spent acid fraction comprising a mixture of spent acid and tar, and separating the spent acid fraction, by flotation separation, centrifugation, or liquid-liquid coalescence, into a tar fraction and a de-tarred spent acid fraction. The fluidized tar and the de-tarred spent acid can each be further processed to produce concentrated acid.Type: GrantFiled: April 15, 2004Date of Patent: April 25, 2006Assignee: Rhodia Inc.Inventors: Richard Wai-Chun Liu, Philip Dean Hill, Thomas Edwin Pruitt, Forrest Lee Sanders, Albert Yi Yang
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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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Patent number: 6833483Abstract: 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: August 1, 2001Date of Patent: December 21, 2004Assignee: The Governors of the University of AlbertaInventors: Karl T. Chuang, Yung F Chen
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Patent number: 6818799Abstract: There is a process for removing by-product tar during the manufacture of isopropyl alcohol. The process comprises the following: a) reacting propylene with concentrated sulfuric acid and water to form isopropyl alcohol and a spent acid having a by-product tar; b) capturing at least a portion of the isopropyl alcohol; c) contacting the spent acid with a gas in bubble form; d) allowing a least a portion of the tar to separate from the remainder of the spent acid to form a layer of tar and a layer of cleaned acid solution; e) capturing the tar; and h) recycling the cleaned acid solution to step a) as a source of sulfuric acid. There is also a process for removing by-product tar during the manufacture of methyl ethyl ketone. The process is substantially the same except that 1-butene is substituted for propylene. There is also a process for removing tar from a spent acid.Type: GrantFiled: April 17, 2003Date of Patent: November 16, 2004Assignee: Rhodia, Inc.Inventors: Richard Wai-Chun Liu, Philip Dean Hill, Thomas Edwin Pruitt, Forrest Lee Sanders, Albert Yi Yang
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Publication number: 20040210095Abstract: There is a process for removing by-product tar during the manufacture of isopropyl alcohol. The process comprises the following: a) reacting propylene with concentrated sulfuric acid and water to form isopropyl alcohol and a spent acid having a by-product tar; b) capturing at leas a portion of the isopropyl alcohol; c) contacting the spent acid with a gas in bubble form; d) allowing a least a portion of the tar to separate from the remainder of the spent acid to form a layer of tar and a layer of cleaned acid solution; e) capturing the tar; and h) recycling the cleaned acid solution to step a) as a source of sulfuric acid. There is also a process for removing by-product tar during the manufacture of methyl ethyl ketone. The process is substantially the same except that 1-butene is substituted for propylene. There is also a process for removing tar from a spent acid.Type: ApplicationFiled: April 17, 2003Publication date: October 21, 2004Applicant: Rhodia Inc.Inventors: Richard Wai-Chun Liu, Philip Dean Hill, Thomas Edwin Pruitt, Forrest Lee Sanders, Albert Yi Yang
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Publication number: 20040171891Abstract: 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: ApplicationFiled: December 19, 2003Publication date: September 2, 2004Applicant: OXENO OLEFINCHEMIE GMBHInventors: Bernhard Scholz, Franz Nierlich, Dieter Reusch, Silvia Santiago Fernandez, Andreas Beckmann, Wilfried Buschken, Alfred Kaizik
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Patent number: 6111148Abstract: A process for continuously producing tertiary butyl alcohol from water and a liquefied gas composed of isobutylene or an isobutylene-containing hydrocarbon using tertiary butyl alcohol as a solvent in the presence of a cation exchange resin in a series multistage reactor, wherein the reaction temperature in each reaction vessel of the series multistage reactor is adjusted to not more than 65.degree. C., a part of the reaction mixture in the outlet of the first reaction vessel is returned to the inlet portion of the first reaction vessel at a circulation ratio of 1.8 to 10, and the weight ratio of the tertiary butyl alcohol to the liquefied gas in the inlet portion of the first reaction vessel is 0.5 to 3.5.Type: GrantFiled: November 30, 1999Date of Patent: August 29, 2000Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Akira Ogawa, Kenichi Fujimoto, Yasutaka Nakashima
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Patent number: 5714646Abstract: A process for producing isopropyl alcohol by hydrating directly propylene and water in the presence of a strong acid solid catalyst which includes feeding continuously propylene, water which is the same as or more than propylene in terms of mole, and a saturated hydrocarbon (propane, butane and the like) to a reactor in which the above solid catalyst is filled or suspended, and carrying out a hydration reaction in the conditions of 50.degree. to 200.degree. C. and 60 to 250 atm while maintaining the concentration of isopropyl alcohol contained in the reaction liquid at 6 to 30 weight %, and then drawing a vapor phase out of the reactor, liquefying a part of thereof by reducing the pressure or cooling to separate vapor components, and refining crude isopropyl alcohol contained in the liquid phase to obtain refined isopropyl alcohol.Type: GrantFiled: December 6, 1995Date of Patent: February 3, 1998Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Shigeru Hirata, Shinji Ogawa
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Patent number: 5672782Abstract: A process for producing a polymer having sulfonic acid groups is provided which comprises treating a polymer having sulfonate salt groups with a ion-exchange resin to change the sulfonate salt groups into sulfonate acid groups with porous-type strongly acidic cation exchange resin. A process for producing a tertiary alcohol is also provided which comprises hydration of olefin by use of the aforementioned polymer as the catalyst. By the process, a tertiary alcohol is produced by hydration of olefin with high selectivity at low cost.Type: GrantFiled: August 16, 1994Date of Patent: September 30, 1997Assignee: Tosoh CorporationInventors: Akitaka Hattori, Kazuhiro Nakamura, Tomohiro Washiyama, Takao Kato, Toshihiro Saito, Shoji Arai
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Patent number: 5608123Abstract: There is provided a process for reacting water and olefin such as ethylene or propylene under mild conditions in the presence of a polyorganosiloxane contaminating sulfonic acid groups to produce alcohol corresponding to the olefin with high yield and selectivity.Type: GrantFiled: June 28, 1995Date of Patent: March 4, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Kaoru Inoue, Masao Iwasaki, Naohiro Ueda
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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: 5475162Abstract: A process of effecting an acid catalyzed reaction wherein a reactant capable of undergoing an acid catalyzed reaction is contacted with an acid functionalized organically-bridged polysilsesquioxane catalyst where all of the acid functionality is covalently bonded to the organic portion of an organically-bridged polysilsesquioxane framework has been developed. The acid functionalized organically-bridged polysilsesquioxane is formed by polymerizing a monomer through sol-gel processing to form an organically-bridged polysilsesquioxane, reacting an acid group onto the organic portion of the organically-bridged polysilsesquioxane, and recovering the acid functionalized product. An embodiment of the invention is where the acid catalyzed reaction is the hydration of olefins, alkylation, acylation, isomerization, or aldol condensation/elimination.Type: GrantFiled: July 19, 1994Date of Patent: December 12, 1995Assignee: UOPInventors: Timothy A. Brandvold, Jennifer S. Holmgren, Thomas P. Malloy
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Patent number: 5345006Abstract: A method and apparatus for conducting a catalytic distillation process is provided which allows for maintaining a liquid level in selected portions of the catalyst bed. Three particular processes disclosed are the production of methyl tertiary butyl ether, tertiary butyl alcohol and cumene.Type: GrantFiled: February 24, 1992Date of Patent: September 6, 1994Inventor: Lawrence A. Smith, Jr.
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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: 5268515Abstract: Propene is reacted with water in a multi-stage, fluidized bed catalytic reactor to produce an oxygenate motor fuel additive containing a major proportion of isopropanol, a minor proportion of diisopropyl ether, and some water. The molar ratio of water to propene introduced into each catalytic stage of the multi-stage reactor is maintained within a range of from about 2:1 to about 6:1. The temperature of the reactants in each of the catalytic stages is maintained within a range of from about 250.degree. F. to about 320.degree. F. and the pressure at a level of from about 1200 psia to about 3600 psia. The temperature in each catalytic stage increases from the initial catalytic stage to the final catalytic stage with the temperature increase being limited to a value within a range of from about 8.degree. F. to about 1.degree. F.Type: GrantFiled: March 1, 1993Date of Patent: December 7, 1993Assignee: The Pritchard CorporationInventor: Robert L. Irvine
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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: 5233102Abstract: A catalyst composition comprising a perfluorinated ion-exchange polymer containing sulfonic acid groups supported on an inert carrier having a hydrophobic surface with a mean pore diameter of at least 1000 .ANG.. Use of this catalyst provides improved hydrocarbon conversion processes for oligomerization of olefins, hydration of olefins and hydrolysis of esters.Type: GrantFiled: November 6, 1991Date of Patent: August 3, 1993Assignee: E. I. du Pont de Nemours and CompanyInventors: Martin H. D. Butt, Francis J. Waller
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Patent number: 5191129Abstract: Propene is reacted with water in a multi-stage, fluidized bed catalytic reactor to produce an oxygenate motor fuel additive containing a major proportion of isopropanol (IPA), some diisopropyl ether (IPE) and some water. The molar ratio of water to propene introduced into each catalytic stage of the multi-stage reactor is maintained within a range of from about 2:1 to about 6:1. The temperature of the reactants in each of the catalytic stages is maintained within a range of from about 250.degree. F. to about 300.degree. F. and the pressure at a level of from about 1200 psia to about 3000 psia. The temperature in each catalytic stage increases from the initial catalytic stage to the final catalytic stage with the temperature increase being limited to a value within a range of from about 8.degree. F. to about 2.degree. F.Type: GrantFiled: May 1, 1992Date of Patent: March 2, 1993Assignee: The Pritchard CorporationInventor: Robert L. Irvine
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Patent number: 5094995Abstract: A catalyst composition comprising a perfluorinated ion-exchange polymer containing sulfonic acid groups supported on an inert carrier having a hydrophobic surface with a mean pore diameter of at least 1000 .ANG.. Use of this catalyst provides improved hydrocarbon conversion processes for oligomerization of olefins, hydration of olefins and hydrolysis of esters.Type: GrantFiled: August 2, 1989Date of Patent: March 10, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Martin H. D. Butt, Francis J. Waller