Sulfur Containing Catalyst Utilized Patents (Class 568/899)
  • Patent number: 9636651
    Abstract: 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: Grant
    Filed: June 11, 2015
    Date of Patent: May 2, 2017
    Assignee: BASF SE
    Inventors: Ulrich Hammon, Thomas Walter
  • Patent number: 9593059
    Abstract: 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: Grant
    Filed: January 9, 2012
    Date of Patent: March 14, 2017
    Assignee: SAUDI ARABIAN OIL COMPANY
    Inventors: Wei Xu, Farhan M. Al-Shahrani, Abdennour Bourane, Stephan Ralf Vogel
  • Patent number: 8987530
    Abstract: A process for producing alcohols from carbonaceous materials such as biomass. The carbonaceous material, such as biomass, is gasified to produce synthesis gas. The synthesis gas then is subjected to a plurality of reactions to produce alcohols having at least four carbon atoms such as butanol and isobutanol.
    Type: Grant
    Filed: August 7, 2012
    Date of Patent: March 24, 2015
    Assignee: Enerkem, Inc.
    Inventors: Anthony S. Carbone, Stephane Marie-Rose, Esteban Chornet
  • Patent number: 8981165
    Abstract: A process for producing alcohols having three carbon atoms from carbonaceous materials such as biomass. The carbonaceous material, such as biomass, is gasified to produce synthesis gas. The synthesis gas then is subjected to a plurality of reactions to produce alcohols such as n-propanol and isopropanol.
    Type: Grant
    Filed: August 7, 2012
    Date of Patent: March 17, 2015
    Assignee: Enerkem, Inc.
    Inventors: Anthony S. Carbone, Stephane Marie-Rose, Esteban Chornet
  • Patent number: 8921619
    Abstract: 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: Grant
    Filed: December 5, 2012
    Date of Patent: December 30, 2014
    Assignee: Saudi Arabian Oil Company
    Inventors: Aadesh Harale, Wei Xu, Ibrahim Abba
  • Publication number: 20140357890
    Abstract: 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: Application
    Filed: November 6, 2012
    Publication date: December 4, 2014
    Applicant: MITSUBISHI RAYON CO., LTD.
    Inventors: Ken Ooyachi, Toshiya Yasukawa, Shuji Akihara
  • Patent number: 8865950
    Abstract: 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: Grant
    Filed: August 10, 2011
    Date of Patent: October 21, 2014
    Assignee: Saudi Arabian Oil Company
    Inventors: Ibrahim Abba, Aadesh Harale, Stephan Ralf Vogel, Wei Xu
  • Publication number: 20140039226
    Abstract: 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: Application
    Filed: January 9, 2012
    Publication date: February 6, 2014
    Applicant: SAUDI ARABIAN OIL COMPANY
    Inventors: Wei Xu, Farhan M. Al-Shahrani, Abdennour Bourane, Stephan Ralf Vogel
  • Patent number: 8637716
    Abstract: 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: Grant
    Filed: October 25, 2006
    Date of Patent: January 28, 2014
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Tatsuo Yamaguchi, Hiroyuki Noda, Toru Watanabe, Shumya Kirino
  • Publication number: 20130261348
    Abstract: Ethane is oxidized to ethylene and/or oxygenates that comprise acetic acid. The acetic acid may be converted to ethanol by hydrogenation. The ethylene may be converted to ethanol by hydration.
    Type: Application
    Filed: March 28, 2012
    Publication date: October 3, 2013
    Applicant: Celanese International Corporation
    Inventors: Mark Scates, Heiko Weiner, Zhenhua Zhou, James Zink
  • Publication number: 20130066118
    Abstract: 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: Application
    Filed: November 6, 2012
    Publication date: March 14, 2013
    Applicant: H R D Corporation
    Inventor: H R D Corporation
  • Patent number: 8288595
    Abstract: 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: Grant
    Filed: February 21, 2012
    Date of Patent: October 16, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Eddy Van Driessche, Jean-Jacques G. Muls, Arie Van Vliet, Carl R. Beck, Charles M. Yarbrough
  • Publication number: 20120232313
    Abstract: 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: Application
    Filed: May 15, 2012
    Publication date: September 13, 2012
    Applicant: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Publication number: 20120149935
    Abstract: 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: Application
    Filed: February 21, 2012
    Publication date: June 14, 2012
    Inventors: Eddy Van Driessche, Jean-Jacques G. Muls, Arie Van Vliet, Carl R. Beck, Charles M. Yarbrough
  • Patent number: 8143459
    Abstract: 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: Grant
    Filed: April 26, 2010
    Date of Patent: March 27, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Eddy Van Driessche, Jean-Jacques G. Muls, Arie Van Vliet, Carl R. Beck, Charles M. Yarbrough
  • Publication number: 20110251441
    Abstract: 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: Application
    Filed: February 15, 2011
    Publication date: October 13, 2011
    Applicant: H R D CORPORATION
    Inventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
  • Publication number: 20100312005
    Abstract: 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: Application
    Filed: April 26, 2010
    Publication date: December 9, 2010
    Inventors: Eddy Van Driessche, Jean-Jacques G. Muls, Arie Van Vliet, Carl R. Beck, Charles M. Yarbrough
  • Patent number: 7795376
    Abstract: 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: Grant
    Filed: July 2, 2009
    Date of Patent: September 14, 2010
    Assignee: Metabolix Inc.
    Inventors: Johan Van Walsem, Erik Anderson, John Licata
  • Patent number: 7622618
    Abstract: 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: Grant
    Filed: November 30, 2006
    Date of Patent: November 24, 2009
    Assignees: Nippon Oil Corporation, Tokyo Institute of Technology
    Inventors: Shinichiro Yanagawa, Michikazu Hara
  • Publication number: 20090137850
    Abstract: 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: Application
    Filed: November 30, 2006
    Publication date: May 28, 2009
    Applicants: Nippon Oil Corporation, Tokyo Institute of Technology
    Inventors: Shinichiro Yanagawa, Michikazu Hara
  • Patent number: 7488837
    Abstract: 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 mixture
    Type: Grant
    Filed: June 28, 2005
    Date of Patent: February 10, 2009
    Assignee: Revo International Inc.
    Inventors: Keiichi Tsuto, Tetsuya Koshikawa
  • Publication number: 20090005613
    Abstract: 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: Application
    Filed: June 20, 2008
    Publication date: January 1, 2009
    Applicant: H R D CORPORATION
    Inventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
  • Patent number: 7399891
    Abstract: 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: Grant
    Filed: June 8, 2005
    Date of Patent: July 15, 2008
    Assignee: 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
  • Patent number: 7211702
    Abstract: 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: Grant
    Filed: November 13, 2003
    Date of Patent: May 1, 2007
    Assignee: The Governors of the University of Alberta
    Inventors: Karl T. Chuang, Yung F. Chen
  • Patent number: 7179948
    Abstract: 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: Grant
    Filed: December 19, 2003
    Date of Patent: February 20, 2007
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Bernhard Scholz, Franz Nierlich, Dieter Reusch, Silvia Santiago Fernandez, Andreas Beckmann, Wilfried Bueschken, Alfred Kaizik
  • Patent number: 7148387
    Abstract: 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: Grant
    Filed: May 27, 2004
    Date of Patent: December 12, 2006
    Assignees: Mitsui Chemicals, Inc., National Institute of Advanced Industrial Science and Technology
    Inventors: Kenta Takahashi, Yutaka Ikushima
  • Patent number: 7115787
    Abstract: 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: Grant
    Filed: November 11, 2003
    Date of Patent: October 3, 2006
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Dieter Reusch, Andreas Beckmann, Franz Nierlich, Axel Tuchlenski
  • Patent number: 7034193
    Abstract: 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: Grant
    Filed: April 15, 2004
    Date of Patent: April 25, 2006
    Assignee: Rhodia Inc.
    Inventors: Richard Wai-Chun Liu, Philip Dean Hill, Thomas Edwin Pruitt, Forrest Lee Sanders, Albert Yi Yang
  • Patent number: 7026519
    Abstract: 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: Grant
    Filed: July 19, 2004
    Date of Patent: April 11, 2006
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Silvia Santiago Fernandez, Andreas Beckmann, Franz Nierlich, Dieter Reusch
  • Patent number: 7002050
    Abstract: 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: Grant
    Filed: March 24, 2005
    Date of Patent: February 21, 2006
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Silvia Santiago Fernandez, Jörg Sauer, Guido Stochniol, Dietrich Maschmeyer, Wilfried Büschken, Klaus-Diether Wiese
  • Patent number: 6951967
    Abstract: 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: Grant
    Filed: February 13, 2003
    Date of Patent: October 4, 2005
    Assignees: EC Erdolchemie GmbH, Bayer AG
    Inventors: Axel Gohrt, Joachim Grub, Stefan Kaminsky, Stephan Muller, Brian Schwegler
  • Patent number: 6906229
    Abstract: 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: Grant
    Filed: February 29, 2000
    Date of Patent: June 14, 2005
    Assignee: ExxonMobil Chemical Patents, Inc.
    Inventor: Paul E. Burton
  • Patent number: 6833483
    Abstract: 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: Grant
    Filed: August 1, 2001
    Date of Patent: December 21, 2004
    Assignee: The Governors of the University of Alberta
    Inventors: Karl T. Chuang, Yung F Chen
  • Patent number: 6818799
    Abstract: 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: Grant
    Filed: April 17, 2003
    Date of Patent: November 16, 2004
    Assignee: Rhodia, Inc.
    Inventors: Richard Wai-Chun Liu, Philip Dean Hill, Thomas Edwin Pruitt, Forrest Lee Sanders, Albert Yi Yang
  • Publication number: 20040210095
    Abstract: 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: Application
    Filed: April 17, 2003
    Publication date: October 21, 2004
    Applicant: Rhodia Inc.
    Inventors: Richard Wai-Chun Liu, Philip Dean Hill, Thomas Edwin Pruitt, Forrest Lee Sanders, Albert Yi Yang
  • Publication number: 20040171891
    Abstract: 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: Application
    Filed: December 19, 2003
    Publication date: September 2, 2004
    Applicant: OXENO OLEFINCHEMIE GMBH
    Inventors: Bernhard Scholz, Franz Nierlich, Dieter Reusch, Silvia Santiago Fernandez, Andreas Beckmann, Wilfried Buschken, Alfred Kaizik
  • Patent number: 6111148
    Abstract: 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: Grant
    Filed: November 30, 1999
    Date of Patent: August 29, 2000
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Akira Ogawa, Kenichi Fujimoto, Yasutaka Nakashima
  • Patent number: 5714646
    Abstract: 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: Grant
    Filed: December 6, 1995
    Date of Patent: February 3, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Shigeru Hirata, Shinji Ogawa
  • Patent number: 5672782
    Abstract: 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: Grant
    Filed: August 16, 1994
    Date of Patent: September 30, 1997
    Assignee: Tosoh Corporation
    Inventors: Akitaka Hattori, Kazuhiro Nakamura, Tomohiro Washiyama, Takao Kato, Toshihiro Saito, Shoji Arai
  • Patent number: 5608123
    Abstract: 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: Grant
    Filed: June 28, 1995
    Date of Patent: March 4, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kaoru Inoue, Masao Iwasaki, Naohiro Ueda
  • Patent number: 5488185
    Abstract: 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: Grant
    Filed: April 22, 1994
    Date of Patent: January 30, 1996
    Assignee: The BOC Group, Inc.
    Inventors: Ramakrishnan Ramachandran, Loc H. Dao
  • Patent number: 5475162
    Abstract: 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: Grant
    Filed: July 19, 1994
    Date of Patent: December 12, 1995
    Assignee: UOP
    Inventors: Timothy A. Brandvold, Jennifer S. Holmgren, Thomas P. Malloy
  • Patent number: 5345006
    Abstract: 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: Grant
    Filed: February 24, 1992
    Date of Patent: September 6, 1994
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 5324866
    Abstract: 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: Grant
    Filed: March 23, 1993
    Date of Patent: June 28, 1994
    Assignee: UOP
    Inventors: Terry L. Marker, Laura E. Kempf
  • Patent number: 5288924
    Abstract: 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: Grant
    Filed: September 18, 1992
    Date of Patent: February 22, 1994
    Assignee: Mobil Oil Corporation
    Inventors: James H. Beech, Jr., Charles M. Sorensen, James A. Stoos, Robert A. Ware
  • Patent number: 5268515
    Abstract: 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: Grant
    Filed: March 1, 1993
    Date of Patent: December 7, 1993
    Assignee: The Pritchard Corporation
    Inventor: Robert L. Irvine
  • Patent number: 5233101
    Abstract: 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: Grant
    Filed: October 9, 1992
    Date of Patent: August 3, 1993
    Assignee: Mobil Oil Corporation
    Inventor: Mohsen N. Harandi
  • Patent number: 5233102
    Abstract: 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: Grant
    Filed: November 6, 1991
    Date of Patent: August 3, 1993
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Martin H. D. Butt, Francis J. Waller
  • Patent number: 5191129
    Abstract: 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: Grant
    Filed: May 1, 1992
    Date of Patent: March 2, 1993
    Assignee: The Pritchard Corporation
    Inventor: Robert L. Irvine
  • Patent number: 5094995
    Abstract: 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: Grant
    Filed: August 2, 1989
    Date of Patent: March 10, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Martin H. D. Butt, Francis J. Waller