Preparing By Hydration Of An Olefin Patents (Class 568/694)
  • Patent number: 10870805
    Abstract: A method for sulfur removal and upgrading comprising the steps of mixing a heated oil feed and a supercritical water feed in a feed mixer, allowing conversion reactions to occur in the supercritical water reactor, reducing the temperature in the cooling device to produce a cooled fluid, reducing the pressure in the depressurizing device to produce a discharged fluid, separating the discharged fluid in the gas-liquid separator to produce a liquid phase product, increasing the pressure to produce pressurized liquid product, the pressure of pressurized liquid product is greater than the critical pressure of water, processing the pressurized liquid product in the hydration reactor to produce a hydrated oil stream, separating the hydrated oil stream to produce an extracted upgraded oil and an oxygenate concentrated stream, the oxygenate concentrated stream comprises the oxygenates, and processing the extracted upgraded oil in the hydrotreater to produce a desulfurized upgraded oil.
    Type: Grant
    Filed: February 12, 2018
    Date of Patent: December 22, 2020
    Inventors: Ki-Hyouk Choi, Muneef F. Alqarzouh
  • Patent number: 10450240
    Abstract: It is desirable to provide improved processes and apparatuses for methylation of aromatic compounds such as toluene and benzene in an aromatics complex. Described herein are processes and apparatuses for methylation of aromatics in an aromatics complex for producing a xylene isomer product. More specifically, processes and apparatuses for producing para-xylene by the selective methylation of toluene and/or benzene in an aromatics complex.
    Type: Grant
    Filed: November 10, 2017
    Date of Patent: October 22, 2019
    Assignee: UOP LLC
    Inventors: Joseph A. Montalbano, R. Jason L. Noe, Veronica G. Deak, Anton N. Mlinar, Robert E. Tsai
  • Publication number: 20150126699
    Abstract: The invention relates to methods and equipment for converting C3+ olefin to, e.g., one or more of di-C3+ olefin, oligomers and polymers of C3+ olefin, branched C4+-aldehydes, C4+-carboxylic acids, and C4+ oxygenates. The invention encompasses producing methyl tert-butyl ether and diisobutylene, and converting methyl tert-butyl ether to isobutylene.
    Type: Application
    Filed: June 21, 2013
    Publication date: May 7, 2015
    Inventors: Matthew B. Yarrison, Alok Srivastava, Roshni Jindal, Chee Keong Then, Rodney S. Smith
  • Patent number: 8865951
    Abstract: Processes for producing mixed alcohols from mixed olefins and the catalyst systems for making such alcohols are provided. Additionally, processes for producing fuel compositions having mixed alcohols prepared from mixed olefins are also provided as embodiments of the present invention. The catalyst systems include a dual phase catalyst system that includes a water soluble acid catalyst and a solid acid catalyst.
    Type: Grant
    Filed: September 12, 2013
    Date of Patent: October 21, 2014
    Assignee: Saudi Arabian Oil Company
    Inventor: Wei Xu
  • Patent number: 8558036
    Abstract: Processes for producing mixed alcohols from mixed olefins and the catalyst systems for making such alcohols are provided. Additionally, processes for producing fuel compositions having mixed alcohols prepared from mixed olefins are also provided as embodiments of the present invention. The catalyst systems include a dual phase catalyst system that includes a water soluble acid catalyst and a solid acid catalyst.
    Type: Grant
    Filed: November 15, 2010
    Date of Patent: October 15, 2013
    Assignee: Saudi Arabian Oil Company
    Inventor: Wei Xu
  • Publication number: 20110137086
    Abstract: In an improved process for telomerizing butadiene, contact butadiene and an organic hydroxy compound represented by formula ROH (I), wherein R is a substituted or unsubstituted C1-C20-hydrocarbyl and the organic hydroxy compound is not glycerol, in a reaction fluid in the presence of a palladium catalyst and a phosphine ligand represented by formula PAr3 (II), wherein each Ar is independently a substituted or unsubstituted aryl having a hydrogen atom on at least one ortho position, at least two Ar groups are ortho-hydrocarbyloxyl substituted aryls. The phosphine ligand has a total of two (2), three (3), four (4), five (5), or six (6) substituted or unsubstituted C1-C20-hydrocarbyloxyls, and optionally, any two adjacent substituents on an Ar group can be bonded to form a 5- to 7-membered ring.
    Type: Application
    Filed: July 22, 2009
    Publication date: June 9, 2011
    Applicant: Dow Global Technologies LLC (Formerly known as Dow Global Technologies Inc.)
    Inventors: John R. Briggs, Jasson T. Patton, Sonet Vermaire-Louw, Peter M. Margl, Henk Hagen, Daryoosh Beigzadeh
  • Patent number: 7601880
    Abstract: The present invention relates to a method for catalytic deoxygenation of process fluids of olefin dimerization processes. According to the invention at least one process fluid containing oxygenates is brought into contact with a deoxygenation catalyst at, at least one location in a column or connected to a column. The present invention relates also to a process for dimerization of olefins, wherein at least part of olefin feed is dimerized in at least one dimerization reaction zone to produce a first product stream comprising oxygenates, and separating in a distillation zone, comprising one or more distillation columns, the first product stream into a second product stream and a third product stream and at, at least one location of the distillation column or a vessel connected to the distillation column is located a deoxygenation catalyst for decomposing oxygenates.
    Type: Grant
    Filed: September 17, 2004
    Date of Patent: October 13, 2009
    Assignee: Neste Oil Oyj
    Inventor: Antti Pyhälahti
  • Patent number: 7256317
    Abstract: The invention describes a process for the preparation of novel surfactant alcohols and surfactant alcohol ethers by derivatization of olefins having from about 10 to 20 carbon atoms or of mixtures of such olefins to give alkanols, and optional subsequent alkoxylation, which comprises subjecting a C4-olefin mixture to metathesis, dimerizing the resulting olefins, and then derivatizing them to give surfactant alcohols, and optionally alkoxylating said alcohols. The olefin mixture obtained in the dimerization has a high proportion of branched components and less than 10% by weight of compounds which contain a vinylidene group. invention further describes the use of the surfactant alcohols and surfactant alcohol ethers to give surfactants by glycosylation or polyglycosylation, sulfation or phosphation.
    Type: Grant
    Filed: January 29, 2004
    Date of Patent: August 14, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Heiko Maas, Michael Roeper, Marc Walter, Ralf Schulz, Juergen Tropsch, Hans-Ulrich Jaeger, Peter Schwab, Michael Schulz
  • 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: 6953867
    Abstract: A catalyst support consisting mainly of synthetic silica, with 0.5-10 parts by weight of one or more oxides or phosphates of the elements of group IIA, IIIB, IVB, VB, VIB, VIIB, VIII, IB, IIB, IIIA, IVA and the lanthanides, wherein the support preparation method comprises mixing particulate synthetic silica with particulate oxides or phosphates of the elements of Groups IIA, IIIB, IVB, VB, VIB, VIIB, VIII, IB, IIB, IIIA, IVA and the lanthanides, or with precursors thereof, a forming step and calcinations. The catalyst support is used together with phosphoric acid in the production of alcohols from olefins by hydration.
    Type: Grant
    Filed: October 19, 2001
    Date of Patent: October 11, 2005
    Assignee: Innovene Europe Limited
    Inventors: Russell William Cockman, Gordon John Haining
  • Publication number: 20040210092
    Abstract: A process for reacting a first component with itself or a second component to produce a third component in which a first material comprising a first component or said first component and a second component is fed to divided wall column having a catalytic distillation structure in at least one of the separate vertical sections of the divided wall column where concurrently: (1) a first component alone or with a second component is contacted with a catalytic distillation structure in a distillation reaction zone thereby catalytically reacting at least a portion of the first component with itself or with the second component to form a product and (2) a first mixture comprising the first component and the product or the first component, the second component and the product; and withdrawing the product from the distillation column reactor; while within the column concurrently with the catalytic reaction and fractionation a second mixture is fractionated, which contains the first component and the product or first a
    Type: Application
    Filed: May 5, 2004
    Publication date: October 21, 2004
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Willibrord A. Groten, Mario J. Maraschino
  • Publication number: 20040210090
    Abstract: A process for reacting a first component with itself or a second component to produce a third component in which a first material comprising a first component or said first component and a second component is fed to divided wall column having a catalytic distillation structure in at least one of the separate vertical sections of the divided wall column where concurrently: (1) a first component alone or with a second component is contacted with a catalytic distillation structure in a distillation reaction zone thereby catalytically reacting at least a portion of the first component with itself or with the second component to form a product and (2) a first mixture comprising the first component and the product or the first component, the second component and the product; and withdrawing the product from the distillation column reactor; while within the column concurrently with the catalytic reaction and fractionation a second mixture is fractionated, which contains the first component and the product or first a
    Type: Application
    Filed: May 5, 2004
    Publication date: October 21, 2004
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Willibrord A. Groten, Mario J. Maraschino
  • Publication number: 20040210091
    Abstract: A process for reacting a first component with itself or a second component to produce a third component in which a first material comprising a first component or said first component and a second component is fed to divided wall column having a catalytic distillation structure in at least one of the separate vertical sections of the divided wall column where concurrently: (1) a first component alone or with a second component is contacted with a catalytic distillation structure in a distillation reaction zone thereby catalytically reacting at least a portion of the first component with itself or with the second component to form a product and (2) a first mixture comprising the first component and the product or the first component, the second component and the product; and withdrawing the product from the distillation column reactor; while within the column concurrently with the catalytic reaction and fractionation a second mixture is fractionated, which contains the first component and the product or first a
    Type: Application
    Filed: May 5, 2004
    Publication date: October 21, 2004
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Willibrord A. Groten, Mario J. Maraschino
  • Publication number: 20040204614
    Abstract: A process for reacting a first component with itself or a second component to produce a third component in which a first material comprising a first component or said first component and a second component is fed to divided wall column having a catalytic distillation structure in at least one of the separate vertical sections of the divided wall column where concurrently: (1) a first component alone or with a second component is contacted with a catalytic distillation structure in a distillation reaction zone thereby catalytically reacting at least a portion of the first component with itself or with the second component to form a product and (2) a first mixture comprising the first component and the product or the first component, the second component and the product; and withdrawing the product from the distillation column reactor; while within the column concurrently with the catalytic reaction and fractionation a second mixture is fractionated, which contains the first component and the product or first a
    Type: Application
    Filed: May 5, 2004
    Publication date: October 14, 2004
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Willibrord A. Groten, Mario J. Maraschino
  • Publication number: 20040186325
    Abstract: The invention describes a process for the preparation of novel surfactant alcohols and surfactant alcohol ethers by derivatization of olefins having from about 10 to 20 carbon atoms or of mixtures of such olefins to give alkanols, and optional subsequent alkoxylation, which comprises
    Type: Application
    Filed: January 29, 2004
    Publication date: September 23, 2004
    Applicant: BASF Aktiengesellschaft
    Inventors: Heiko Maas, Michael Roper, Marc Walter, Ralf Schulz, Jurgen Tropsch, Hans-Ulrich Jager, Peter Schwab, Michael Schulz
  • Publication number: 20030069452
    Abstract: A reactant selected from the group consisting of alkanes, alkenes, and aromatics is reacted with a metal halide to form the halide of the reactant and reduced metal. The reduced metal is oxidized to form metal oxide. The metal oxide is reacted with the halide of the reactant to produce the alcohol and/or the ether corresponding to the reactant and the original metal halide which is recycled.
    Type: Application
    Filed: November 19, 2002
    Publication date: April 10, 2003
    Inventors: Jeffrey H. Sherman, Eric McFarland
  • Patent number: 6479710
    Abstract: A solid acid-base catalyst contains vanadium pentoxide hydrate. Moreover, it is preferable that the vanadium pentoxide hydrate in the solid acid-base catalyst has a composition which is represented by the following general equation (1): V2O5.nH2O  (1) (n: 0.1-3). Creation of the vanadium pentoxide hydrate was confirmed by measuring X-ray diffraction spectrum shown in FIG. 1. In accordance with the above arrangement, the solid acid-base catalyst can sufficiently display catalytic activity under mild conditions, and it can be suitably applied to various reactions, such as the syntheses of olefins or ethers through dehydration reactions of alcohols, the syntheses of aldehydes or ketones through dehydrogenation reactions of alcohols, hydrations and isomerization reactions of olefins, alkylations, esterifications, amidations, acetalizations, aminations, hydrogen shift reactions, aldol condensation reactions and polymerization reactions.
    Type: Grant
    Filed: March 15, 1999
    Date of Patent: November 12, 2002
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Nobuji Kishimoto, Etsushige Matsunami
  • Publication number: 20020121223
    Abstract: A copolymer of a strait chain &agr;-olefin and a vinyl compound (I) represented by the general formula CH2═CH—R, wherein R is a hydrocarbon group, the steric parameter Es of the substituent R is −1.64 or less and the steric parameter B1 of the substituent R is 1.53 or more, an adhesive containing the same as an effective ingredient, and an laminate containing the adhesive.
    Type: Application
    Filed: December 21, 2001
    Publication date: September 5, 2002
    Inventors: Nobuo Oi, Akihiro Kondo, Toshiki Mori
  • Patent number: 6069284
    Abstract: A process to separate diisopropyl ether from a mixture of diisopropyl ether, isopropyl alcohol, and water has been developed. The process begins with distilling, in a distillation column, the mixture into a bottoms stream containing water and isopropyl alcohol and an overhead stream containing an azeotrope of diisopropyl ether, isopropyl alcohol, and water. The overhead stream is condensed and allowed to form an aqueous phase enriched in isopropyl alcohol and water and an organic phase enriched in diisopropyl ether with some water and isopropyl alcohol in an overhead receiver. The aqueous phase is recycled to the distillation column. The organic phase is passed to a drier to form a bottoms product stream containing at least 99 mole percent diisopropyl ether and a drier overhead stream containing an azeotrope of diisopropyl ether, isopropyl alcohol, and water.
    Type: Grant
    Filed: June 17, 1998
    Date of Patent: May 30, 2000
    Assignee: UOP LLC
    Inventors: Charles P. Luebke, William A. Leet
  • Patent number: 6049012
    Abstract: A catalyst for production of alkyl tert alkyl ether from sulfur contaminated feedstock includes an ion exchange resin; a palladium first metal phase supported on the resin; and a sulfur inhibiting second metal phase supported on the resin for inhibiting sulfur deactivation of the first metal phase, wherein the first metal phase is present at an atomic ratio to the second metal phase of between about 1:20 to about 1:0.1. A process for producing alkyl tert alkyl ethers includes the steps of providing a liquid olefinic hydrocarbon feedstock containing sulfur and having a total sulfur content of up to about 300 ppm; providing a catalyst as described above; mixing the feedstock with alcohol and hydrogen to obtain a reaction feedstock; and contacting the reaction feedstock with the catalyst under etherification conditions so as to produce alkyl tert alkyl ether.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: April 11, 2000
    Assignee: Intevep, S.A.
    Inventors: Magdalena Ramirez de Agudelo, Trino J. Romero, Emilia Mujica
  • Patent number: 5990361
    Abstract: A low pressure catalytic distillation process for producing high purity ethyl tertiary butyl ether that contains less than 0.6 weight percent ethanol, and preferably less than 0.07 weight percent ethanol, has been developed. The high purity ethyl tertiary butyl ether is withdrawn directly from a catalytic distillation column. No downstream processing is necessary to remove excess ethanol from the ether product. A stream containing a significant amount of one or more inert azeotropic agents such as normal butane, isopentane, and isobutane is introduced along with the isobutylene and ethanol reactants into an etherification zone containing a catalytic distillation column. The catalytic distillation column is operated under low pressure conditions which result in the reaction of the ethanol with the isobutylene to form ethyl tertiary butyl ether.
    Type: Grant
    Filed: June 18, 1998
    Date of Patent: November 23, 1999
    Assignee: UOP LLC
    Inventors: Stanley J. Frey, Scott P. Davis, Steven L. Krupa, Paul R. Cottrell
  • Patent number: 5986148
    Abstract: An improved process for production of diisopropyl ether by conversion of hydrocarbon feedstock containing propene, propane and C.sub.2 -- light gas components. The overall process steps include, (optionally) prefractionating fresh feedstock containing propene, propane and C.sub.2 -- light gas components to provide a reactor feedstream rich in propene; contacting the feedstock and water in a catalytic reactor with acidic catalyst under olefin hydration and etherification conditions; and recovering from the catalytic reactor a liquid reactor effluent stream containing diisopropyl ether, isopropanol, water, unreacted propene, propane, oligomer and C.sub.2 -- light gas components. DIPE product containing C.sub.6 + oligomer is recovered by separating the liquid effluent stream in a stripper column, and extracting the DIPE-rich liquid with water. An improved separation process is employed for removing water to provide DIPE liquid product substantially free of water.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: November 16, 1999
    Assignee: Mobil Oil Corporation
    Inventors: James H. Beech, Jr., Douglas Miller, Jorge Luis Soto, James A. Stoos, Albert H. Wu
  • Patent number: 5824825
    Abstract: A phosphoric acid catalyst on a shaped, inorganic support and its use for the hydration of olefins. At least 90 wt. % of the catalyst support consists of titanium dioxide and/or zirconium dioxide and has outstanding ageing stability under the hydrothermal conditions existing during hydration processes.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: October 20, 1998
    Assignee: Degussa Aktiengesellschaft
    Inventors: Hermanus Lansink-Rotgerink, Harald Hoecker, Stefan Wieland, Steffen Seebald, Heike Riedemann
  • Patent number: 5808161
    Abstract: A process has been discovered to employ an inert or unreactive solvent in the liquid phase process for production of isopropyl alcohol and diisopropyl ether from a propylene-rich hydrocarbon feedstream and water where the process is carried out in contact with acidic aluminosilicate catalyst particles. When an inert solvent is used, oxygenates production is enhanced and catalyst productivity is substantially increased.
    Type: Grant
    Filed: December 4, 1995
    Date of Patent: September 15, 1998
    Assignee: Mobil Oil Corporation
    Inventors: Stephen H. Brown, Jeffrey C. Trewella
  • Patent number: 5628880
    Abstract: A process for removing dienes from etherification uses a hydrogenation zone in the reactor distillation column above the etherification zone. MTBE is produced and the unreacted C.sub.4 stream is also subjected to selective hydrogenation of the butadiene contained in the C.sub.4 feed stream. The C.sub.4 stream is first contacted with methanol in the etherification zone where the MTBE is distilled downward. The unreacted C.sub.4 's then are subjected to selective hydrogenation in the hydrogenation zone where butadiene in the overhead raffinate is reduced by over 90%. The hydrotreated C.sub.4 's are thus suitable for cold acid alkylation or other use wherein butadiene is harmful.
    Type: Grant
    Filed: February 12, 1996
    Date of Patent: May 13, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Gary R. Gildert, Willibrord A. Groten
  • Patent number: 5600024
    Abstract: A process for producing ethyl tertiary butyl ether and for the substantially complete recovery by fractional distillation of the unreacted ethanol contained in an etherification reaction zone product stream as a product along with the ethyl tertiary butyl ether reaction product. This process utilizes methanol as a fractionator feed additive to enhance the recovery of ethanol as a bottoms product.
    Type: Grant
    Filed: July 26, 1995
    Date of Patent: February 4, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Robert B. Eldridge, Gary R. Patton
  • Patent number: 5600023
    Abstract: In a single stage process for producing diisopropyl ether in the presence of an organic solvent, SO.sub.3 from a DIPE reactor effluent is transferred to an aqueous phase in a liquid extraction zone and removed from the aqueous phase using a basic ion exchange resin disposed in an SO.sub.3 removal zone. As a consequence, DIPE reactor effluent can be returned to the DIPE reactor to serve as a solvent and to assist in providing cooling to the DIPE reactor without causing catalyst deactivation.
    Type: Grant
    Filed: November 18, 1994
    Date of Patent: February 4, 1997
    Assignee: UOP
    Inventors: Terry L. Marker, Laura E. Kempf
  • Patent number: 5569789
    Abstract: A multistaged fixed catalyst bed process for the production of diisopropyl ether and isopropanol is disclosed comprising a fixed bed of serially connected stages containing zeolite Beta catalyst. A feedstream of propylene and water equivalents selected from the group consisting of water, isopropanol and diisopropyl ether is introduced into each stage at a rate sufficient to provide a mole ratio of water equivalents to propylene equivalents that increases in increments by stage from at least 0.1 in a first stage to at most 1.2 in a final stage. The feedstream is introduced at a temperature between 50.degree. and 450.degree. C., pressure between 700 and 24000 kPa, and weight hourly space velocity between 0.10 and 30, based on catalyst, whereby a single non-aqueous liquid phase is maintained in the fixed bed. An effluent product stream is recovered comprising diisopropyl ether, isopropanol and water from the final stage. Isopropanol is recycled to the first stage when the preferred product is diisopropyl ether.
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: October 29, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Weldon K. Bell, Stephen H. Brown, Jeffrey C. Trewella
  • Patent number: 5504257
    Abstract: A process for the production of diisopropyl ether where acid is removed, without extraction, from the reactor effluent before being recycled to the reactor or being passed to downstream processing units has been developed. The process involves (1) reacting propylene and water to produce isopropyl alcohol in a reactor and reacting the isopropyl alcohol with propylene to produce diisopropyl ether in the presence of an acidic ion exchange resin catalyst to afford a reactor effluent stream containing at least water, isopropyl alcohol, diisopropyl ether, propylene, and acid, (2) passing the reactor effluent to an acid removal zone to produce an acid-depleted stream, (3) dividing the acid-depleted stream into two portions, and (4) recycling a portion to the reactor and collecting a portion.
    Type: Grant
    Filed: September 26, 1994
    Date of Patent: April 2, 1996
    Assignee: UOP
    Inventors: Terry L. Marker, Robert J. Schmidt, Richard E. Marinageli, Timothy A. Brandvold
  • Patent number: 5473105
    Abstract: A process for concurrently producing diisopropyl ether and isopropyl ethyl ether from water, ethanol from an independent source, and propylene, has been developed. The product mixture may be used as a high octane number booster due mainly to the presence of the diisopropyl ether and to a lesser extent, the isopropyl ethyl ether. Furthermore, the product mixture, upon blending with gasoline, incorporates a renewable resource into the gasoline since the isopropyl ethyl ether is produced from ethanol. Optionally, the product mixture may be passed through an acid removal zone to remove acid, if present, before being recycled or further processed. A portion of the product mixture is recycled to the reaction zone to increase the conversion of reactants to products.
    Type: Grant
    Filed: October 4, 1994
    Date of Patent: December 5, 1995
    Assignee: UOP
    Inventors: Terry L. Marker, Robert J. Schmidt, Richard E. Marinangeli, Allyn T. Gilbert
  • Patent number: 5405814
    Abstract: An olefin hydration catalyst is regenerated with a non-oxidizing light gas, such as hydrogen. Light olefins, especially propylene, are converted to a mixture of alcohol(s), such as isopropanol (IPA) and ether(s), such as diisopropylether (DIPE) by contacting a feed containing the olefin with water and/or alcohol with the olefin hydration catalyst. Regeneration conditions include temperatures of from about 150.degree. C. to about 550.degree. C., pressures below about 1000 psig (6900 kPa). Lower pressures of regeneration unexpectedly demonstrated more effective catalyst regeneration through greater coke removal.
    Type: Grant
    Filed: June 7, 1993
    Date of Patent: April 11, 1995
    Assignee: Mobil Oil Corporation
    Inventors: James H. Beech, Jr., Weldon K. Bell, W. Thomas Mo, Hye Kyung C. Timken, Robert A. Ware
  • Patent number: 5395981
    Abstract: Ethers suitable for use as high octane oxygenate additives for motor fuels or other compounds such as alcohols or alkylates are produced in a catalytic distillation process wherein a C.sub.4 -plus isoolefin(s) and an alcohol present in the catalytic distillation zone overhead stream are charged to a packed liquid-phase reaction zone containing an etherification catalyst before being recycled to the overall catalytic distillation zone. The effluent of the liquid-phase reactor is returned to the catalytic distillation zone at a point above the catalyst in this zone. The feed(s) to the process passes directly into the catalytic distillation zone, without passage through a prereactor, at a point located below a majority of catalyst bed in the catalytic distillation zone.
    Type: Grant
    Filed: August 27, 1993
    Date of Patent: March 7, 1995
    Assignee: UOP
    Inventor: Terry L. Marker
  • Patent number: 5371301
    Abstract: In a single stage process for producing diisopropyl ether, SO.sub.3 from a DIPE reactor effluent is transferred to an aqueous phase in a liquid extraction zone and removed from the aqueous phase using a basic ion exchange resin disposed in an SO.sub.3 removal zone. As a consequence, DIPE reactor effluent can be returned to the DIPE reactor to serve as a solvent and to assist in providing cooling to the DIPE reactor without causing catalyst deactivation.
    Type: Grant
    Filed: June 21, 1993
    Date of Patent: December 6, 1994
    Assignee: UOP
    Inventors: Terry L. Marker, Laura E. Kempf
  • Patent number: 5324865
    Abstract: A process for production of diisopropyl ether by conversion of hydrocarbon feedstock containing propene, propane and C.sub.2 - light gas components, including the steps of: optionally, prefractionating fresh feedstock containing propene, propane and C.sub.2 - light gas components to provide a reactor feedstream rich in propene; contacting the feedstock and water in a catalytic reactor with acidic catalyst under olefin hydration and etherification conditions; and recovering from the catalytic reactor a liquid reactor effluent stream containing diisopropyl ether, isopropanol, water, unreacted propene, propane and C.sub.2 - light gas components. Improved operation is achieved by separating the liquid effluent stream in a vertical stripper column; recovering an overhead vapor stream containing propene, propane and C.sub.2 - light gas components from the stripper column; cooling the overhead vapor stream to provide a reflux stream rich in condensed propene and propane; removing the C.sub.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: June 28, 1994
    Assignee: Mobil Oil Corporation
    Inventors: James H. Beech, Jr., Douglas Miller, Jorge L. Soto, James A. Stoos, Albert H. Wu
  • 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: 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: 5144084
    Abstract: Olefins are converted to alcohols and/or ethers employing, as catalyst, an acidic zeolite which has been bound with an essentially non-acidic refractory oxide of at least one metal of Group IVA and/or IVB of the Period Table of the Elements, e.g., silica, titania, zirconia and/or germania.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: September 1, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Charles M. Sorensen, Philip Varghese, David O. Marler
  • Patent number: 5113024
    Abstract: In the instant invention the effluent from the DIPE reactor is separated in a novel separation process that includes, in one embodiment, two extraction steps serially combined to initially separate IPA from the reaction products by extraction with water. The aqueous IPA extract is separated in a second extraction step carried out using the C.sub.3 hydrocarbon feedstream to the process as extractor. To effectuate the separation of aqueous IPA, the second extraction is carried out at a temperature higher than that of the first extraction step. The organic phase from the first extraction containing DIPE, C.sub.3 hydrocarbons and water is separated in a splitter to provide dry DIPE as product. In another embodiment dry DIPE is produced by an initial aqueous extraction of the reaction effluent followed by distillation to separate C.sub.3 hydrocarbons and water overhead and DIPE as a bottom stream.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: May 12, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 5105023
    Abstract: A process for converting light olefin to alcohol(s), ether(s) or mixtures of alcohol(s) and ether(s) which comprises contacting a feed containing at least one light olefin with water in the vapor and/or liquid phase under olefin hydration conditions in the presence of acidic zeolite MCM-22 as olefin hydration catalyst to produce said alcohol(s) and/or ether(s).
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: April 14, 1992
    Assignee: Mobil Oil Corp.
    Inventors: David O. Marler, Charles M. Sorensen, Philip Varghese
  • Patent number: 5080691
    Abstract: Light olefins are converted to gasoline with a high enough content of ethers to provide a significant octane improvement over a base (or `cracking`) gasoline (clear RON=90-92; clear MON=79-80). One portion of the olefins is hydrated to produce alcohols, and the other is used to synthesize an olefin-rich gasoline. The alcohols are used to etherify the gasoline. The combination of unit operations minimizes the energy needed to run the process for which no external solvent is needed. The process capitalizes on the higher solubility in gasoline of ethanol, propanol and butanol, compared to methanol. Besides having very low solubility in gasoline, etherification with methanol or ethanol produces an inadequately rewarding increase in octane number, compared to propanol or isopropanol. Taking advantage of the inherent chemical and physical properties of C.sub.3 -C.sub.
    Type: Grant
    Filed: April 4, 1990
    Date of Patent: January 14, 1992
    Assignee: Mobil Oil Corp.
    Inventors: Charles M. Sorensen, Sadi Mizrahi, Samuel A. Tabak
  • Patent number: 5078751
    Abstract: A process is disclosed for upgrading C.sub.5 -C.sub.8 olefin-containing gasoline to a high octane motor gasoline blending component.C.sub.3 -C.sub.4 olefins are hydrated to alcohols and then selectively removed from the aqueous hydration reactor effluent stream via liquid extraction with the gasoline feedstream. The alcohol enriched gasoline extract stream is then etherified and unreacted alcohols are extracted to yield a high octane gasoline blending component free of metal-bearing additives.
    Type: Grant
    Filed: April 4, 1990
    Date of Patent: January 7, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Sadi Mizrahi, Charles M. Sorensen, Samuel A. Tabak
  • Patent number: 5041690
    Abstract: Methanol or other alcohol is converted to high octane gasoline components by an integrated process wherein crude aqueous alcohol feedstock is extracted with a liquid extractant stream containing C.sub.4 +iso-olefin and reacted to form tertiary-alkyl ethers, such as MTBE. The aqueous raffinate is converted to olefinic hydrocarbons in a MTO catalytic reactor. Propene from the MTO reaction is reacted with water to produce di-isopropyl ether, which may be blended with MTBE and C.sub.6 +MTO hydrocarbons to produce high octane gasoline. Isobutylene and isoamylenes from the MTO reaction can be recovered and recycled as a liquid extractant stream.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: August 20, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4978807
    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. A method for the production of methyl tertiary butyl ether by reaction of isobutene with methanol in a distillation reaction column is disclosed wherein a liquid level maintained in the distillation reaction zone.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: December 18, 1990
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4927977
    Abstract: A process and apparatus are provided for the substantially uniform distribution of a two-phase feed in a chemical reaction zone. As applied, for example, to the hydration/etherification of light olefin to alcohol(s) and/or ether(s), the invention results in greater process control and in particular cases, to improved reaction product selectivities.
    Type: Grant
    Filed: January 12, 1989
    Date of Patent: May 22, 1990
    Assignee: Mobil Oil Corporation
    Inventors: Jonathan E. Child, Byung C. Choi, Francis P. Ragonese
  • Patent number: 4590294
    Abstract: The invention relates to the use of hydrogen ion-exchanged layered clays in organic reactions which are catalyzed by protons. Such organic reactions include the production of ethers by the reaction of an alcohol with an olefin or an olefin oxide, the production of an ether by the reaction of a primary or secondary aliphatic alcohol or an olefin oxide, the production of an alkyl aromatic compound by the reaction of an aromatic hydrocarbon with an olefin or a C.sub.2 or higher alcohol and the production of an alcohol by the hydration of an olefin.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: May 20, 1986
    Assignee: The British Petroleum Company Limited
    Inventors: James A. Ballantine, Reginald Gregory, John H. Purnell, John M. Thomas, David J. Westlake
  • Patent number: 4503263
    Abstract: The invention concerns a process for the preparation of aliphatic ethers by reacting the corresponding alcohol and/or olefin over a superacid catalyst.
    Type: Grant
    Filed: September 2, 1982
    Date of Patent: March 5, 1985
    Assignee: Atochem
    Inventor: George A. Olah