Preparing By Hydration Of Olefin Patents (Class 568/895)
  • Publication number: 20080293976
    Abstract: The invention relates to regenerative, supported amine sorbents that includes an amine or an amine/polyol composition deposited on a nano-structured support such as nanosilica. The sorbent provides structural integrity, as well as high selectivity and increased capacity for efficiently capturing carbon dioxide from gas mixtures, including the air. The sorbent is regenerative, and can be used through multiple operations of absorption-desorption cycles.
    Type: Application
    Filed: July 19, 2007
    Publication date: November 27, 2008
    Inventors: George A. Olah, Alain Goepert, Sergio Meth, G.K. Surya Prakash
  • Publication number: 20080132732
    Abstract: The present invention relates to a catalytic process for making butenes using a reactant comprising 2-butanol and water. The butenes so produced may be converted to isoalkanes, alkyl-substituted aromatics, isooctanes, isooctanols and ethers, which are useful as transportation fuels.
    Type: Application
    Filed: June 13, 2007
    Publication date: June 5, 2008
    Inventors: Leo Ernest Manzer, Michael B. D'amore, Edward S. Miller, Jeffrey P. Knapp
  • Publication number: 20080033218
    Abstract: 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: Application
    Filed: June 20, 2007
    Publication date: February 7, 2008
    Inventors: James R. Lattner, Matthew James Vincent, Kun Wang, Michel Molinier, Michael J. Veraa, Anthony F. Volpe, Hailian Li, Jeffrey C. Yoder, Mark Muraoka
  • Patent number: 7297324
    Abstract: Microchannel devices and method of use are disclosed wherein a reaction microchamber 52 is in thermal contact with a heat exchange channel 61. An equilibrium limited exothermic chemical process occurs in the reaction microchamber 52. Sufficient heat is transferred to the heat exchange channels to substantially lower the temperature in the reaction microchamber 52 down its length to substantially increase at least one performance parameter of the exothermic chemical process relative to isothermal operation. Optionally, an endothermic reaction occurs in the heat exchange channel 61 which is sustained by the exothermic chemical process occurring the exothermic reaction chamber. Both the reaction chamber 52 and the heat exchange channel 61 can be of micro dimension. Catalyst 75 can be provided in the microchamber 52 in sheet form such that reactants flow by the catalyst sheet.
    Type: Grant
    Filed: March 11, 2003
    Date of Patent: November 20, 2007
    Assignee: Battelle Memorial Institute
    Inventors: Ward E. TeGrotenhuis, David L. King, Greg A. Whyatt, Christopher M. Fischer, Robert S. Wegeng, Kriston P. Brooks
  • Patent number: 7235702
    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: March 12, 2004
    Date of Patent: June 26, 2007
    Assignee: Governors of the University of Alberta
    Inventors: Karl T. Chuang, Yung F. Chen
  • 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: 7183446
    Abstract: The present invention relates to an alcohol mixture which substantively comprises alcohols having 13 or 15 carbon atoms, to a process for its preparation, to a process for functionalizing these alcohol mixtures, and to the resultant functionalized alcohol mixtures and their use.
    Type: Grant
    Filed: June 25, 2001
    Date of Patent: February 27, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Edgar Zeller, Jürgen Tropsch
  • 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: 7064238
    Abstract: A process is provided for converting an alkane to an oxygenated product by passing an alkane gas over a first fixed bed containing a higher valence bromide salt to produce an alkyl bromide, a hydrobromic acid, and a lower valence bromide salt. The alkyl bromide and hydrobromic acid are conveyed as a gas to a second fixed bed containing a metal oxide and are passed over the second fixed bed to produce the first bromide salt and the oxygenated product. The metal oxide in the second fixed bed is regenerated by passing oxygen over the second fixed bed producing the metal oxide and bromine. The bromine is conveyed as a gas from the second fixed bed to the first fixed bed. The first bromide salt of the first fixed bed is regenerated by passing the bromine over the first fixed bed producing the first bromide salt.
    Type: Grant
    Filed: January 2, 2004
    Date of Patent: June 20, 2006
    Assignee: Marathon Oil Company
    Inventor: John J. Waycuilis
  • 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
  • Publication number: 20040242940
    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.
    Type: Application
    Filed: May 27, 2004
    Publication date: December 2, 2004
    Inventors: Kenta Takahashi, Yutaka Ikushima
  • 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: 20040171890
    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: Application
    Filed: March 12, 2004
    Publication date: September 2, 2004
    Inventors: Karl T. Chuang, Yung F. Chen
  • Publication number: 20030220525
    Abstract: Disclosed are processes for conversion of (3R,3′R,6′R)-lutein to (3R,6′R)-&agr;-cryptoxanthin, (3R)-&bgr;-cryptoxanthin, anhydroluteins I, II, and III (dehydration products of lutein), and a method for separating and purifying the individual carotenoids including the unreacted (3R,3′R)-zeaxanthin. The invention also includes two methods that transform (3R,3′R,6′R)-lutein into (3R,6′R)-&agr;-cryptoxanthin in excellent yields.
    Type: Application
    Filed: January 24, 2003
    Publication date: November 27, 2003
    Inventor: Frederick Khachik
  • Publication number: 20030097030
    Abstract: A process for producing branched olefins from a mixed linear olefin/paraffin isomerisation feed comprising linear olefins having at least 7 carbon atoms in 5-50% w comprising in a first stage skeletally isomerising linear olefins in the isomerisation feed and in a second stage separating branched and linear molecules wherein branched molecules are substantially olefinic and linear molecules are olefinic and/or paraffinic; novel stages and combinations thereof; apparatus therefor; use of catalysts and the like therein; and use of branched olefins obtained thereby.
    Type: Application
    Filed: August 14, 2002
    Publication date: May 22, 2003
    Inventor: Peter Arnoldy
  • Publication number: 20020133050
    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: Application
    Filed: August 1, 2001
    Publication date: September 19, 2002
    Inventors: Karl T. Chuang, Yung F. Chen
  • Patent number: 6432858
    Abstract: This invention relates to a method for regenerating a cyclic olefin hydration catalyst, in which a solid acid catalyst is regenerated after its use in a hydration reaction of a cyclic olefin by mixing a water phase containing the solid acid catalyst and an oil phase containing the cyclic olefin and thereby effecting the reaction, which comprises separating the reaction solution into oil phase and water phase at a temperature of 40° C. or more and subsequently subjecting at least a portion of the solid acid catalyst in the separated water phase to a regeneration treatment. According to the method of this invention, a catalyst used in the hydration of a cyclic olefin can be separated and regenerated efficiently, and it is a particularly suitable catalyst regeneration method for a case in which hydration of a cyclic olefin is carried out for a prolonged period of time by repeating regeneration and use of the catalyst again and again.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: August 13, 2002
    Assignee: Mitsubishi Chemical Corporation
    Inventor: Makoto Tezuka
  • Patent number: 6414202
    Abstract: A process for manufacturing isopropyl alcohol by reacting propylene with a reagent, including treating a vent stream from the reaction zone, to recover propylene for return to the reactor. The process involves using a gas separation membrane to separate propylene from propane in the reactor vent stream. The membrane separation step results in a residue stream typically containing as much as 30% propane or more, which is vented from the process, and a permeate stream typically containing 95% or less propylene, which is recirculated to the reactor.
    Type: Grant
    Filed: August 30, 2000
    Date of Patent: July 2, 2002
    Assignee: Membrane Technology and Research, Inc.
    Inventors: Richard W. Baker, Andre R. Da Costa, Ramin Daniels
  • Patent number: 6284930
    Abstract: 3-Hydroxypropanal is prepared by reacting acrolein with water under pressure and in the presence of an ion exchange resin while adding a carboxylic acid to the reaction mixture.
    Type: Grant
    Filed: August 25, 1999
    Date of Patent: September 4, 2001
    Assignee: E.I. Du Pont de Nemours and Company
    Inventors: Thomas Haas, Liane Deusser, Torsten Hahm, Willi Hofen, Rudolf Vanheertum
  • 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: 5892066
    Abstract: Propylene is oxidized with molecular oxygen in the liquid phase to form products including propylene oxide, propylene glycol, propylene glycol esters, allyl alcohol, acrolein and acetal, the acrolein is hydrogenated to allyl alcohol, the acetol is hydrogenated to propylene glycol, the propylene glycol esters are hydrolyzed to propylene glycol, and propylene oxide, propylene glycol and allyl alcohol are recovered as products.
    Type: Grant
    Filed: December 12, 1997
    Date of Patent: April 6, 1999
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Roger A. Grey
  • Patent number: 5763693
    Abstract: In a process for producing isopropyl alcohol by direct liquid phase hydration of propylene and water in the presence of a strong acid solid catalyst at a high temperature and a high pressure, the reaction is carried out at a temperature in a ranging between 100.degree. and 250.degree. C. and a pressure in a ranging between 60 and 200 atm in an excess of water. Then, a liquid phase of the reaction product is contacted with an extraction agent of a saturated hydrocarbon having 3 or 4 carbon atoms at a temperature in a ranging between the critical temperature of the extraction agent and the temperature higher than the critical temperature by 40.degree. C. under a pressure ranging between the critical pressure of the extraction agent and 200 atm at an S/F ratio ranging between 0.3 and 3 which is calculated from the equation of the amount of the extraction agent divided by the amount of the extract feed.
    Type: Grant
    Filed: February 21, 1996
    Date of Patent: June 9, 1998
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Shigeru Hirata, Shinji Ogawa
  • 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: 5712313
    Abstract: A process for carrying out a chemical equilibrium reaction is disclosed in which, in a first stage, one or more reactants are contacted with a fixed arrangement of a catalyst under conditions such that the reactants and the products of the reaction are gaseous, the unconverted reactants and products of the first stage being passed to a second stage, in which they are contacted with a fixed arrangement of a catalyst and the reaction allowed to proceed in the presence of an absorbent capable of absorbing a product of the reaction.
    Type: Grant
    Filed: February 26, 1996
    Date of Patent: January 27, 1998
    Assignee: Shell Oil Company
    Inventors: Gert Jan Kramer, Jean Paul Lange
  • Patent number: 5696304
    Abstract: The disclosure describes a process for producing alkadienols comprising the steps of: reacting a conjugated alkadiene with water in a reaction solvent in the presence of a palladium catalyst; distilling the obtained reaction mixture so as to separate the reaction solvent from the reaction mixture while directly supplying heated water, steam or a mixture thereof as a heating medium to a distillation column, under the condition that the temperature of a bottom liquid in the distillation column is not higher than 120.degree. C.; and phase-separating bottoms discharged from the bottom of the distillation column.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: December 9, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Chihiro Miyazawa, Tomoyuki Mori, Hiroshi Kameo, Shinji Isogai
  • 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: 5382705
    Abstract: A process for upgrading a light olefin feed by converting the 1-olefins to higher molecular weight oligomers and the iso-oleins to fuel ethers or alcohols. The process provides substantial improvements in the production of lower alkyl tertiary alkyl ethers or tertiary alkyl alcohol, such as methyl tertiary butyl ether (MTBE), methyl tertiary amyl ether (TAME) or tertiary butyl alcohol. The 1-olefin component of the hydrocarbon feedstream is separated by selective oligomerization in contact with a reduced chromium oxide catalyst to form an olefin oligomer of higher molecular weight, such as gasoline, distillate and lube range hydrocarbons. The iso-olefins are separated by etherification with a lower alcohol such as methanol or by hydration to form an alcohol such as tertiary butanol. The oligomerization process can be integrated either upstream or downstream of the etherification step.
    Type: Grant
    Filed: November 10, 1992
    Date of Patent: January 17, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Harold S. Chung, Andrew Jackson, Margaret M. Wu
  • Patent number: 5302762
    Abstract: Disclosed is a method for hydrating a cycloolefin, in which the hydration is conducted in a reaction system comprising a continuous aqueous phase including water and a crystalline aluminosilicate catalyst suspended therein and an oil phase including a cycloolefin, while dispersing the oil phase as globules having a specific diameter. By the method of the present invention, not only can a cyclic alcohol be produced at high selectivity and in high yield, but the activity of the catalyst can also be stably maintained at a high level for a prolonged period of time, and the produced cyclic alcohol can be readily separated.
    Type: Grant
    Filed: March 17, 1993
    Date of Patent: April 12, 1994
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Kunihiko Yamashita, Hideaki Obana, Tadashi Kai
  • Patent number: 5284979
    Abstract: A process is disclosed for the preparation of 3-hydroxyalkanals having 3 to 12 carbon atoms, in particular 3 or 4 carbon atoms, by hydration of the underlying 2-alkenals with water in a homogeneous phase in the presence of an acid catalyst. The previously known hydration using mineral acids or carboxylic acids as catalyst results in low volume/time yields and/or low selectivities. These disadvantages can be avoided by using in the present invention, as catalyst, a dissolved acid-base buffer which results in a pH of from 2 to 5 in the reaction mixture; the acid component and corresponding base of which are present in a total quantity of from 0.5 to 40% by weight in the reaction mixture. The preferred buffers composed of a lower monobasic carboxylic acid and a tertiary amine can easily be recycled.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: February 8, 1994
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Georg Bohme, Dietrich Arntz
  • Patent number: 5283377
    Abstract: A method for producing octadienols, which comprises reacting 1,3-butadiene with water in the presence of a palladium compound, a phosphine compound and carbon dioxide, wherein a compound of the formula (I): ##STR1## wherein each of R.sup.1, R.sup.5 and R.sup.9 which may be the same or different, is a hydrocarbon group, and each of R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, R.sup.10, R.sup.11 and R.sup.12 which may be the same or different, is hydrogen or a substituent, provided that at least one of them is an electron donative substituent, is used as the phosphine compound.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: February 1, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Iwao Nakajima, Yoko Misu
  • 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: 5262576
    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 19, 1992
    Date of Patent: November 16, 1993
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 5245093
    Abstract: A process for reacting a fluid phase (gaseous and/or liquid phase) in contact with a solid phase in a reaction zone, wherein the improvement in said process comprises reacting the fluid phase in contact with the solid phase in a horizontally-oriented fluidized bed vessel. The vessel includes at least two compartments or stages, and includes means for vibrating the vessel. The process of the present invention enables one to effect fluidization of the solid phase independently of the flow rate or velocity of the fluid phase, thus enabling proper contact time of the fluid phase with the solid phase and minimizing the amount of fluid phase reactant to be recycled.
    Type: Grant
    Filed: January 26, 1989
    Date of Patent: September 14, 1993
    Assignee: ABB Lummus Crest Inc.
    Inventor: George Ember
  • Patent number: 5221441
    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: October 4, 1991
    Date of Patent: June 22, 1993
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • 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: 5011506
    Abstract: A method is disclosed combining the process for the hydration or etherification of light linear olefins, such as the production of diisopropyl ether (DIPE), with the process for the etherification of C.sub.4 + or C.sub.4 hydrocarbons containing isobutylene to produce alkyl tertiary butyl ether or ether-rich gasoline in a manner which effectively dewaters alkanol using the iso-olefin hydrocarbon feedstream as extractant. The combined process leads to the production of isopropyl tert-alkyl ethers. In the integrated process the high octane ethers produced may include methyl tert-butyl ether, methyl tert-amyl ether, isopropyl tert-butyl ether and diisopropyl ether. The process also results in the production of a gasoline stream rich in high octane ethers.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: April 30, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4990692
    Abstract: Cyclohexanol is removed from aqueous solutions containing it and aromatic sulfonic acids by extraction with one or more cyclohexyl ethers liquid under extraction conditions and having the formula ##STR1## where R is alkyl of from 1 to 16 catbon atoms, cycloalkyl of from 5 to 8 carbon atoms, aralkyl of from 7 to 10 carbon atoms or phenyl, which may additionally have substituents which are inert under reaction conditions.
    Type: Grant
    Filed: July 21, 1989
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Juergen Gosch, Rolf Fischer
  • Patent number: 4981605
    Abstract: A liquid modified ethylenic random copolymer selected from an epoxidization product of a liquid ethylenic random copolymer of ethylene and an alpha-olefin having 3 to 20 carbon atoms and a hydroxylation product of a liquid ethylenic random copolymer of ethylene and an alpha-olefin having 3 to 20 carbon atoms. The modified copolymer is characterized in that (i) the liquid modified ethylenic random copolymer has an ethylene component content of 10 to 85 mole % and an alpha-olefin component content of 15 to 90 mole %, (ii) in the .sup.13 C-NMR spectrum of the liquid modified ethylenic random copolymer, signals of .alpha..beta. and .beta..gamma.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: January 1, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Toshiyuki Tsutsui, Akinori Toyota, Norio Kashiwa
  • Patent number: 4956506
    Abstract: A gas containing water vapor and a minor amount of ethylene and/or propylene is passed through several reactors in series containing a perfluorinated ion-exchange polymer catalyst to convert olefins to alcohols, and alcohol product is recovered from the effluent gases from each reactor.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: September 11, 1990
    Assignee: Conoco Inc.
    Inventor: Edward G. Latimer
  • Patent number: 4902385
    Abstract: Practically anhydrous crude sec-butyl alcohol produced by catalytic direct hydration of n-butenes is freed by means of water from the azeotropically boiling and low-boiling by-products by continuous azeotropic distillation in a separation column, the prepurified anhydrous sec-butyl alcohol obtained is withdrawn and the high-boiling by-products are subsequently separated in a separate column.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: February 20, 1990
    Assignee: Deutsche Texaco Aktiengesellschaft
    Inventor: Gunther Osterburg
  • Patent number: 4879422
    Abstract: A method for producing a cycloalkanol in high yield by hydrating cycloalkene with a specific catalyst is disclosed. The catalyst is obtainable by ion-exchanging all or a part of the cations of a crystalline gallium silicate with hydrogen ions. It has a specific composition defined by the general formula and is characterized by the X-ray diffraction pattern.
    Type: Grant
    Filed: June 27, 1988
    Date of Patent: November 7, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamio Shirafuji, Kiyomi Sakai
  • Patent number: 4849551
    Abstract: An industrially excellent method for separating cyclohexanol which comprises carrying out the hydration of cyclohexane in the presence of an acid, and bringing the reaction solution into contact with a mixed solution of a hydrocarbon and phenol to extraction-separate cyclohexanol from the reaction solution.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: July 18, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamio Shirafuji, Itaru Kawata