Including Displacement From Nonhydrocarbon By Entire Hydrocarbon Molecule, E.g., Growth Reaction, Etc. Patents (Class 585/328)
  • Patent number: 9012713
    Abstract: The present invention provides a process for removing oxygenate from an olefin stream comprising oxygenate, comprising providing to an oxygenate recovery zone the olefin stream comprising oxygenate and a solvent comprising ethanol, treating the olefin stream comprising oxygenate with the solvent, and retrieving from the oxygenate recovery zone at least one oxygenate-depleted olefinic product stream comprising olefin and a spent solvent comprising at least part of the oxygenate.
    Type: Grant
    Filed: December 20, 2013
    Date of Patent: April 21, 2015
    Assignee: Shell Oil Company
    Inventor: Jeroen Van Westrenen
  • Publication number: 20140171665
    Abstract: The present invention provides a process for removing oxygenate from an olefin stream comprising oxygenate, comprising providing to an oxygenate recovery zone the olefin stream comprising oxygenate and a solvent comprising ethanol, treating the olefin stream comprising oxygenate with the solvent, and retrieving from the oxygenate recovery zone at least one oxygenate-depleted olefinic product stream comprising olefin and a spent solvent comprising at least part of the oxygenate.
    Type: Application
    Filed: December 20, 2013
    Publication date: June 19, 2014
    Applicant: Shell Oil Company
    Inventor: Jeroen VAN WESTRENEN
  • Patent number: 8680352
    Abstract: A method for producing a linear paraffin product from natural oil and kerosene includes providing a first feed stream comprising kerosene, pre-fractionating the first feed stream to produce a heart cut paraffin stream comprising paraffins in a heart cut range, and combining the heart cut paraffin stream with a second feed stream comprising natural oil to form a combined stream. The method further includes deoxygenating the natural oil and fractionating the combined stream to remove paraffins that are heavier than the heart cut range.
    Type: Grant
    Filed: April 2, 2013
    Date of Patent: March 25, 2014
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Stephen W. Sohn
  • Patent number: 8629310
    Abstract: Oxygenate feedstocks derived from biomass are converted to a variety of fuels including gas, jet, and diesel fuel range hydrocarbons. General methods are provided including hydrolysis, dehydration, hydrogenation, condensation, oligomerization, and/or a polishing hydrotreating.
    Type: Grant
    Filed: March 9, 2012
    Date of Patent: January 14, 2014
    Assignee: Phillips 66 Company
    Inventors: Edgar Lotero, Kristi Fjare, TiePan Shi, Sourabh Pansare, Yun Bao
  • Publication number: 20140005452
    Abstract: A new family of crystalline microporous metallophosphates designated AlPO-59 has been synthesized. These metallophosphates are represented by the empirical formula R+rMm2+EPxSiyOz where R is an organoammonium cation such as the ETMA+, M is a framework metal alkaline earth or transition metal of valence 2+, and E is a trivalent framework element such as aluminum or gallium. The AlPO-59 compositions are characterized by a new unique ABC-6 net structure and compositions and have catalytic properties for carrying out various hydrocarbon conversion processes, and separation properties for separating at least one component.
    Type: Application
    Filed: June 29, 2012
    Publication date: January 2, 2014
    Applicant: UOP LLC
    Inventors: Gregory J. Lewis, Lisa M. Knight, Paulina Jakubczak, Justin E. Stanczyk
  • Publication number: 20130245290
    Abstract: The present invention provides a process for preparing ethylene and propylene, comprising the step of: a) contacting a feed comprising methanol, ethanol and C4+ olefins with a catalyst, comprising ZSM-5 having a silica to alumina ratio in the range of from 40 to 100, at a temperature in the range of from 350 to 1000° C. to obtain a olefinic product comprising ethylene and propylene.
    Type: Application
    Filed: September 7, 2012
    Publication date: September 19, 2013
    Applicant: SHELL OIL COMPANY
    Inventors: Sivakumar SADASIVAN VIJAYAKUMARI, Jeroen VAN WESTRENEN
  • Publication number: 20120271081
    Abstract: The invention relates to a process for producing distillate from a charge of heteroatomic organic compounds comprising at least one heteroatom chosen from oxygen, sulfur and halogen, alone or in combination, in which the treatment of the charge comprises at least one step of conversion of the heteroatomic organic compounds into olefins performed in a first conversion zone, and, in at least a second oligomerization zone, a step of oligomerization of olefins originating at least partly from the conversion zone, in the presence of at least 0.5% by weight of oxygenated compounds, in order to produce a distillate. By virtue of the presence of oxygenated compounds during the oligomerization, this process makes it possible to improve the yield of distillate, making it possible to obtain a higher degree of oligomerization relative to the oligomerization of the same charge under the same reaction conditions.
    Type: Application
    Filed: October 13, 2010
    Publication date: October 25, 2012
    Applicant: TOTAL RAFFINAGE MARKETING
    Inventors: Nikolai Nesterenko, Delphine Minoux, Sander Van Donk, Jean-Pierre Dath
  • Patent number: 8178737
    Abstract: A process for producing propylene from ethylene and a feed stream comprising 1-butene, 2-butene, n-butane, and isobutane is disclosed. A butenes stream (1-butene and 2-butene) is produced from the feed stream by removing the paraffins. The butenes stream is reacted in the presence of an isomerization catalyst to produce an isomerized stream with increased concentration of 2-butene. The isomerized stream is reacted with ethylene in the presence of a metathesis catalyst to produce a reaction mixture comprising propylene; the propylene may be isolated from the reaction mixture by distillation. The removal of paraffins from the feed stream improves the catalyst productivity and the plant throughput.
    Type: Grant
    Filed: June 14, 2007
    Date of Patent: May 15, 2012
    Assignee: Lyondell Chemical Technology, L.P.
    Inventor: David W. Leyshon
  • Patent number: 8053619
    Abstract: Process for the production of alkenes from a feedstock comprising monohydric aliphatic paraffinic alcohols having from 2 to 3 carbon atoms, in which the monohydric aliphatic paraffinic alcohols containing 2 to 3 carbon atoms are dehydrated into the corresponding same carbon number alkenes at a pressure of more than 0.5 MPa but less than 4.0 MPa and at a temperature of less than 300° C. The alcohols present in the feedstock comprise ethanol, propanol(s), less than 1 wt % of methanol and less than 1 wt % of C3+ alcohols.
    Type: Grant
    Filed: June 29, 2006
    Date of Patent: November 8, 2011
    Assignee: BP Chemicals Limited
    Inventor: Benjamin Patrick Gracey
  • Patent number: 7964762
    Abstract: The present invention relates to a process for the producing propylene and ethylene from a light hydrocarbon stream comprising essentially ethane and butane. The process involves a non-catalytic cracking of ethane and normal-butane followed by a metathesis of ethylene and 2-butene to increase the propylene yield. Optionally the by-produced iso-butane is dehydrogenated and subsequently the produced iso-butene is converted to other valuable products like di-isobutylene, alkylate for gasoline blending tertiary-butyl-ethers, poly-isobutylene methyl-metacrylate or isoprene.
    Type: Grant
    Filed: May 16, 2007
    Date of Patent: June 21, 2011
    Assignee: Total Petrochemicals Research Feluy
    Inventors: Francois Bouvart, Walter Vermeiren, Wolfgang Garcia, Alain Chepda
  • Patent number: 7868216
    Abstract: A process for producing high purity propylene comprises: a step for dimerizing ethylene to 1-butene; a step for hydroisomerizing 1-butene to 2-butenes; and a step for metathesis of 2-butenes by ethylene. Advantageously, the ethylene used to produce the 1-butene and ethylene for metathesis derive from a steam cracking unit. To increase propylene production, the process can use a steam cracking or FCC C4cut as an additional butene source.
    Type: Grant
    Filed: December 23, 2005
    Date of Patent: January 11, 2011
    Assignee: IFP Energies Nouvelles
    Inventors: Jean-Alain Chodorge, Christian Dupraz
  • Patent number: 7790941
    Abstract: The invention concerns methods and systems for minimizing back-mixing of feedstock flow in converting oxygenates to olefins. In one embodiment, back-mixing is reduced by providing a reactor that includes baffles to reduce the hydraulic diameter of at least a portion of the reactor. Some or all of the baffles can also serve as cooling tubes for reducing temperature gradients in the reactor, and thereby maximize light olefin production.
    Type: Grant
    Filed: May 16, 2006
    Date of Patent: September 7, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: James H. Beech, Jr., Nicolas Coute, Jeffrey S. Smith, Michael Peter Nicoletti, Charles O. Bolthrunis, Domenic C. Ferrari, Umesh K. Jayaswal, Roy Walter Silverman
  • Patent number: 7714179
    Abstract: Processes for preparing a C5 aldehyde and propene are disclosed, the processes comprising: (a) providing a feedstream, the feedstream comprising butane, 1-butene, 2-butene and 1,3-butadiene, the 1,3-butadiene present in the feedstream in an amount up to 1000 ppm; (b) contacting the feedstream with hydrogen and carbon monoxide in the presence of a hydroformylation catalyst to form a 2-butene-rich butane stream and a C5 aldehyde; (c) separating the 2-butene-rich butane stream and the C5 aldehyde; and (d) contacting the 2-butene-rich butane stream with ethene in the presence of a metathesis catalyst to form a propene-containing hydrocarbon stream.
    Type: Grant
    Filed: August 6, 2005
    Date of Patent: May 11, 2010
    Assignee: BASF SE
    Inventors: Marcus Sigl, Markus Schubert, Jürgen Stephan, Rainer Papp, Frank Poplow
  • Patent number: 7589245
    Abstract: A process for the preparation of linear alpha olefins having 2n carbon atoms from linear alpha olefins having n carbon atoms comprising the steps of (a) dimerizing a linear alpha olefin having n carbon atoms in the presence of a dimerization catalyst to produce a linear internal olefin having 2n carbon atoms; (b)(i) reacting the linear internal olefin having 2n carbon atoms produced in step (a) with a trialkylaluminium compound in the presence of a catalytic amount of an isomerization/displacement catalyst in order to cause isomerization of the linear internal olefin and to displace alkyl group(s) from said trialkylaluminium compound to form an alkyl aluminium compound wherein at least one of the alkyl groups bound to aluminium is a linear alkyl which has been derived from the isomerization of said linear internal olefin; and (b)(ii) reacting said alkyl aluminium compound with an alpha olefin optionally in the presence of a displacement catalyst so as to displace said linear alkyl from said alkyl aluminium co
    Type: Grant
    Filed: July 12, 2005
    Date of Patent: September 15, 2009
    Assignee: Shell Oil Company
    Inventors: Eric Johannes Maria De Boer, Harry Van Der Heijden, Inge Oosterveld, Arie Van Zon
  • Patent number: 7501546
    Abstract: The invention relates to a process for producing high-quality hydrocarbon base oil of biological origin. The process of the invention comprises alcohol condensation, hydrodeoxygenation, and isomerization steps. Alcohols, preferably fatty alcohols of biological origin are used as the feedstock.
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: March 10, 2009
    Assignee: Neste Oil Oj
    Inventors: Eija Koivusalmi, Juha Moilanen
  • Patent number: 7368621
    Abstract: The invention relates to a process for preparing 1-octene from a C4 fraction from a cracker by telomerization of the 1,3-butadiene present in the C4 fraction from a cracker by means of methanol in the presence of a catalyst, hydrogenation of the telomer obtained in this way, dissociation of the hydrogenated telomer and work-up of the resulting dissociation product to give pure 1-octene.
    Type: Grant
    Filed: May 6, 2004
    Date of Patent: May 6, 2008
    Assignee: OXENO Olefinchemie GmbH
    Inventors: Joerg Krissmann, Dirk Roettger, Cornelia Borgmann, Kerstin Kaemper, Franz Nierlich, Alfred Kaizik, Udo Knippenberg, Rainer Malzkorn
  • Patent number: 7102038
    Abstract: A process for making a selectively branched alcohol composition contacting a lower olefin feed comprising linear olefins having at least 3 carbon atoms and a concentration of phosphorous-containing compounds with a sorbent comprising a metal or metal oxide on a support, thereby substantially reducing the concentration of phosphorous-containing compounds and producing a purified lower olefin feed. The purified lower olefin feed is skeletally isomerized and then treated to selectively hydrogenate dienes before hydroformylation to produce selectively branched alcohols.
    Type: Grant
    Filed: August 9, 2002
    Date of Patent: September 5, 2006
    Assignee: Shell Oil Company
    Inventors: Brendan Dermont Murray, Paul Benjerman Himelfarb, Zaida Diaz, David Michael Singleton
  • Patent number: 6756514
    Abstract: A process for dimerizing vinyl olefins that is fully integrated into a process for making vinyl olefins is disclosed.
    Type: Grant
    Filed: December 9, 2002
    Date of Patent: June 29, 2004
    Assignee: BP Corporation North America Inc.
    Inventors: George Barac, Larry L. Bendig, William L. Cox, Larry H. Nemec
  • Publication number: 20040110999
    Abstract: A process for dimerizing vinyl olefins that is fully integrated into a process for making vinyl olefins is disclosed.
    Type: Application
    Filed: December 9, 2002
    Publication date: June 10, 2004
    Inventors: George Barac, Larry L. Bendig, William L. Cox, Larry H. Nemec
  • Patent number: 6455747
    Abstract: The present invention provides a method for converting a feed containing oxygenates to olefins and comprises the following steps: providing a feed including an oxygenate; contacting the feed in a reactor apparatus with a catalyst including a molecular sieve, the contacting taking place under conditions effective to convert the oxygenate to a product including a light olefin, the conditions including a gas superficial velocity of at least two meters per second; and recirculating a first portion of the catalyst to recontact the feed.
    Type: Grant
    Filed: October 7, 1999
    Date of Patent: September 24, 2002
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: James R. Lattner, Stephen N. Vaughn, Keith H. Kuechler, David C. Skouby, Hsiang-Ning Sun
  • Patent number: 6375832
    Abstract: A method of transforming a normally gaseous composition containing at least one hydrogen source, at least one oxygen source and at least one carbon source into a normally liquid fuel, wherein said gaseous composition consists at least in part of carbon dioxide as said carbon source and said oxygen source, and of methane as said hydrogen source and as a second carbon source; the method comprising the steps of feeding the composition into a reactor including a first electrode means, a second electrode means and at least one layer of a normally solid dielectric material positioned between the first and the second electrode means; submitting the composition within the reactor in the presence of a normally solid catalyst to a dielectric barrier discharge, wherein said normally solid catalyst is a member selected from the group of zeolites, aluminophosphates, silicoaluminophosphates, metalloaluminophosphates and metal oxides containing OH groups; and controlling the dielectric barrier discharge to convert the gaseo
    Type: Grant
    Filed: March 21, 2000
    Date of Patent: April 23, 2002
    Assignee: ABB Research Ltd.
    Inventors: Baldur Eliasson, Eric Killer, Chang-Jun Liu
  • Patent number: 6303839
    Abstract: The present invention relates to a process for the production of light olefins comprising olefins having from 2 to 4 carbon atoms per molecule from an oxygenate feedstock. The process comprises passing the oxygenate feedstock to an oxygenate conversion zone containing a metal aluminophosphate catalyst to produce a light olefin stream. A propylene stream and/or mixed butylene is fractionated from said light olefin stream and cracked to enhance the yield of ethylene and propylene products. This combination of light olefin product and propylene and butylene cracking in a riser cracking zone or a separate cracking zone provides flexibility to the process which overcomes the equilibrium limitations of the aluminophosphate catalyst. In addition, the invention provides the advantage of extended catalyst life and greater catalyst stability in the oxygenate conversion zone.
    Type: Grant
    Filed: June 14, 2000
    Date of Patent: October 16, 2001
    Assignee: UOP LLC
    Inventor: Terry L. Marker
  • Patent number: 6303021
    Abstract: The improved process and apparatus of the present invention for extracting high purity aromatics from gasoline using a glycol solvent based extraction process decrease liquid-vapor flashing, reduce reflux flow rate, and use heat of enthalpy produces at one point as a source of energy used at another point, decreasing energy consumption while significantly increasing purity and amount of product obtained.
    Type: Grant
    Filed: December 12, 2000
    Date of Patent: October 16, 2001
    Assignee: Denim Engineering, Inc.
    Inventors: George Winter, Zvi Merchav
  • Patent number: 6258992
    Abstract: Lower hydrocarbons are converted to carboxylic acids and/or dehydrogenated hydrocarbon product by contacting a feed mixture containing lower hydrocarbons, oxygen source, diluent, and sulfur-containing compound, with a multifunctional, mixed metal catalyst at a temperature from about 150° C. up to about 400° C. The lower hydrocarbons include C2-C4, and the presence of sulfur compound in the feed mixture results in increased yield of carboxylic acid and/or dehydrogenated hydrocarbon product.
    Type: Grant
    Filed: September 17, 1999
    Date of Patent: July 10, 2001
    Assignee: Saudi Basic Industries Corporation
    Inventors: Khalid Karim, Asad Khan
  • Patent number: 6020285
    Abstract: Shaped particles suitable for use as a catalyst, or precursor thereto, particularly for the decomposition of hypohalite ions in aqueous solution, comprising a high alumina cement having an aluminium to calcium atomic ratio above 2.5 and at least one oxide of a Group VIII metal M selected from nickel and cobalt, said particles containing 10 to 70% by weight of said Group VIII metal oxide and having a porosity in the range of 30 to 60%, in which at least 10% of the pore volume is in the form of pores of size in the range 15 to 35 nm and less than 65% of the pore volume is in the form of pores of diameter greater then 35 nm are disclosed.
    Type: Grant
    Filed: January 22, 1998
    Date of Patent: February 1, 2000
    Assignee: Imperial Chemical Industries PLC
    Inventor: Frederick Ernest Hancock
  • Patent number: 5877378
    Abstract: The alpha-olefin content of mixed hydrocarbon streams is selectively utilized to produce trialkylaluminum compounds in which the alkyl groups are linear primary alkyl groups. This selective utilization is accomplished by use of a specific, highly selective low residence-time, low isomerization catalytic displacement reaction. In addition, when alpha-olefins are the desired end product, a second low residence-time catalytic displacement reaction is utilized whereby high purity alpha olefins are produced.
    Type: Grant
    Filed: September 15, 1997
    Date of Patent: March 2, 1999
    Assignee: Amoco Corporation
    Inventors: Andrew D. Overstreet, Robert H. Allen, Larry H. Nemec, Ronny W. Lin
  • Patent number: 5817902
    Abstract: The invention provides a process for making .alpha.-olefins. In the chain growth reaction step of the process a jet loop reactor is used to fully use high pressure ethylene, and two or more stages of the chain growth reaction is used to raise the selectivity of C.sub.6-10 olefins.
    Type: Grant
    Filed: November 12, 1996
    Date of Patent: October 6, 1998
    Assignees: China Petro-Chemical Corporation, Daqing Petrochemical Works, China Petrochemical Corporation
    Inventors: Minghe Xie, Anshun Sun, Daohua Jiang, Jiabo Qu, Qian Chen, Weibin Li, Zongsheng Yuan, Chunmei Yu, Xixia Song, Shubao Wan, Zhengnian Luo, Fengrong Wang, Qun Xu, Shulan Wang, Yingjie Feng, Yongchen Sun
  • Patent number: 5780697
    Abstract: A process for deactivating a nickel, cobalt, or nickel and cobalt displacement catalyst during a reaction wherein an alkyl group is displaced from a trialkyl aluminum compound in a reaction mixture containing said catalyst is disclosed. The process involves adding a deactivating amount of a catalyst poison containing silver, silver compounds, silver complexes, thallium, thallium compounds, thallium complexes, or mixtures thereof to the reaction mixture after the displacement has proceeded to the desired extent.
    Type: Grant
    Filed: June 17, 1997
    Date of Patent: July 14, 1998
    Assignee: Amoco Corporation
    Inventors: Ronny Wen-Long Lin, Richard Andrew Holub, Richard Neil Hollenshead
  • Patent number: 5731480
    Abstract: A process is described for coproducing vinylidene alcohol and vinylidene olefin. The process involves dimerizing one or more vinylolefins with an alkyl aluminum catalyst to form a first product mixture comprising at least vinylidene olefin and alkyl aluminum compound. The vinylidene olefin is then reacted with the alkyl aluminum compound under displacement conditions to form 1-olefin while concurrently removing the 1-olefin from the displacement reaction mixture to form a second product mixture comprising at least beta-branched alkyl aluminum compound. The second product mixture is treated with air or oxygen under mild oxidation conditions to form a third product mixture comprising at least beta-branched aluminum alkoxide. The beta-branched aluminum alkoxide is then hydrolyzed to form vinylidene alcohol. The process makes effective use of the alkyl aluminum catalyst both as a catalyst and as a reactant, and requires only a relatively small amount of reaction equipment.
    Type: Grant
    Filed: November 3, 1995
    Date of Patent: March 24, 1998
    Assignee: Albemarle Corporation
    Inventor: Kaung-Far Lin
  • Patent number: 5550303
    Abstract: Olefin is formed by displacing alkyl groups of aluminum trialkyl by contacting ethylene with the aluminum trialkyl in an ethylene:aluminum trialkyl mol ratio in the range of 2-8:1 at about 0.degree.-70.degree. C. and at atmospheric up to about 1000 psia pressure, for a reaction time of about 0.5 to about 60 minutes in the presence of a displacement enhancing amount of a nickel- or cobalt-containing displacement catalyst. Despite the fact that the displacement reaction is an equilibrium reaction, the process does not use, as did the prior art, large excesses of ethylene to shift the equilibrium to favor displacement. Consequently, the volumes of ethylene used in the processing are reduced very substantially and yet yields of the desired displaced alpha olefin remain favorable.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: August 27, 1996
    Assignee: Amoco Corporation
    Inventors: Ronny W. Lin, Robert H. Allen, Andrew D. Overstreet
  • Patent number: 5518932
    Abstract: The process of preparing higher aluminum alkyls by olefin chain growth on alkyl aluminum is improved by using on-line flow-through calorimetry to determine the aluminum concentration of a process stream, such as the aluminum alkyl feed stream, by reacting a sample portion of the process stream with a molar excess of alcohol and measuring the change in temperature. The aluminum concentration of the stream can then be adjusted as required to maintain it within a selected range.
    Type: Grant
    Filed: June 21, 1993
    Date of Patent: May 21, 1996
    Assignee: Albemarle Corporation
    Inventors: Robert P. Gallant, Isaac L. Smith, Joseph B. Tedder, Jr., Lloyd T. Crasto, George A. Daniels
  • Patent number: 5498735
    Abstract: A process of producing an .alpha.-olefin which comprises carrying out separately the growth of ethylene with triethyl aluminum and the growth of ethylene with tributyl aluminum, displacing the resulting higher trialkyl aluminum with ethylene, thereby forming triethyl aluminum and an .alpha.-olefin, and displacing at least part of the resulting triethyl aluminum with butene contained in the resulting .alpha.-olefin, thereby forming tributyl aluminum.The present invention permits the efficient production of .alpha.-olefins containing linear .alpha.-olefins in extremely high purity. The .alpha.-olefins will find use as comonomers for polyolefins (whose demand is increasing recently) and also as raw materials of synthetic lubricants.
    Type: Grant
    Filed: July 18, 1994
    Date of Patent: March 12, 1996
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Kunio Takeuchi, Takao Tamura, Hironori Tashiro
  • Patent number: 4990712
    Abstract: Gasoline octane number and yield are improved while excess fuel gas production is decreased in a catalytic cracking process by integrating etherification and oxygenate/aliphatic upgrading processes into the catalytic cracking unit product fractionation section.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: February 5, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4935569
    Abstract: Alpha-olfins containing about 6-14 carbon atoms are made in a dual displacement loop ethylene/tri-lower alkyl chain growth process which includes, in one closed loop, an initial ethylene/triethyl aluminum (TEA) chain growth, C.sub.2-14 olefin separation, 2-stage ethylene displacment, C.sub.2-12 olefin separation and recycle of residual TEA and higher olefins back to the initial ethylene/TEA chain growth. A second closed loop starts with the same ethylene/TEA chain growth product followed by C.sub.4-14 olefin separation, C.sub.4-8 olefin displacement on the bottoms from C.sub.4-14 olefin separation, ethylene chain growth on the C.sub.4-8 olefin displacement product and recycle of this ethylene displacement product back to the olefin separation stage following the initial ethylene/TEA chain growth reaction.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: June 19, 1990
    Assignee: Ethyl Corporation
    Inventors: Alvin E. Harkins, Layne W. Summers
  • Patent number: 4918254
    Abstract: Alkyl groups in trialkyl aluminum are displaced by .alpha.-olefins in the presence of a nickel catalyst. The displaced alkyl group evolve as .alpha.-olefins. The displacement is fast and the catalyst is then poisoned with a catalyst poison such as lead to prevent undesired side reactions such as isomerization of .alpha.-olefins to internal olefins or dimerization to vinylidene olefins.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: April 17, 1990
    Assignee: Ethyl Corporation
    Inventors: Steven P. Diefenbach, Gene C. Robinson
  • Patent number: 4895996
    Abstract: Alkenes are prepared by the hydroboration of enamines followed by an elimination reaction to form the alkene. This process has wide applicability and is useful for the stereospecific synthesis of [Z] isomers. It is preferred to use 9-borabicyclo[3.3.1 nonane as the hydroborating agent and to use methanol to catalyze the elimination reaction.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: January 23, 1990
    Assignees: Purdue Research Foundation, The Dow Chemical Company
    Inventors: Christian T. Goralski, Bakthan Singaram, Herbert C. Brown
  • Patent number: 4886924
    Abstract: A process for the stereospecific synthesis of [E] alkenes from enamines comprising the steps of hydroborating the enamine; esterifying the organoborane so formed and oxidizing the boronic ester in the presence of hydrogen peroxide and in the absence of added base under conditions sufficient to form the [E] alkene in high yield.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: December 12, 1989
    Assignee: The Dow Chemical Company
    Inventors: Christian T. Goralski, Bakthan Singaram, Herbert C. Brown
  • Patent number: 4774365
    Abstract: The present invention is an improved process for separating alcohols from ethers and/or hydrocarbon raffinate in an etherification process. The excess alcohol reactant, which forms azeotrope mixtures with the product ethers and C.sub.4 -C.sub.7 raffinate, is removed by passing the liquid azeotrope mixture over a pervaporation membrane which effectively breaks the azeotrope and permeates the alcohol with high flux and high selectivity. In a typical etherification process, one or more pervaporation membrane units can be located ahead of the ether/raffinate distillation step, in conjunction with the distillation step with a liquid side draw, after the distillation step, or a combination of any of the above. The present invention also provides an improved process for separating alcohols from ethers and/or hydrocarbon raffinate in an ether decomposition process for the production of high purity iso-alkene products.
    Type: Grant
    Filed: November 25, 1987
    Date of Patent: September 27, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael S. Chen, Robert M. Eng, Jerome L. Glazer, Charles G. Wensley
  • Patent number: 4749818
    Abstract: A process for the preparation of cis-9-tricosene is disclosed. Cis-1,9-octadecadiene, which may be obtained by the dehydration of oleyl alcohol, is metallated with an organomagnesium halide, producing cis-9-octadecenylmagnesium halide, which in turn is alkylated with n-pentyl halide to form the desired cis-9-tricosene.
    Type: Grant
    Filed: September 30, 1987
    Date of Patent: June 7, 1988
    Assignee: Phillips Petroleum Company
    Inventors: Jim D. Byers, Charles A. Drake
  • Patent number: 4714796
    Abstract: A process for oxidative pyrolysis of halogenated methanes in the presence of oxygen-containing gas under non-flame conditions is provided whereby the formation of solid carbonaceous materials is significantly reduced, while high yields of desired higher molecular weight hydrocarbons such as acetylene and ethylene are maintained.
    Type: Grant
    Filed: April 21, 1987
    Date of Patent: December 22, 1987
    Assignee: Illinois Institute of Technology
    Inventor: Selim M. Senkan
  • Patent number: 4713424
    Abstract: A continuous, liquid phase method for producing a polymer having a predetermined number of conjugated diene units per molecule in which (a) a first monomer stream is contacted with an organo-lithium compound, in a manner to intimately mix increments of monomer, containing the predetermined number of moles of conjugated diene, with each mole of organo-lithium and continuously mix and move the mixture through a first, elongated reaction zone to react the predetermined number of moles of conjugated diene with one mole of organo-lithium, (b) mixing the effluent from (a) with an alkyl-substituted aromatic hydrocarbon, an organo-alkali metal of potassium, rubidium or cesium and a tertiary amine to form a complex-initiator of the aromatic hydrocarbon, the alkali metal and the amine, (c) mixing the effluent from (b) with a second stream of monomer, in a manner to intimately mix increments of monomer, containing the predetermined number of moles of conjugated diene, with each mole of complex-initiator and continuously
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: December 15, 1987
    Assignee: Phillips Petroleum Company
    Inventor: Ronald E. Brown
  • Patent number: 4484014
    Abstract: A lube-oil range hydrocarbon mixture is produced by the oligomerization of a branched olefin mixture which contains olefins of 6 to 16 carbon atoms and has a degree of branching of about 10 to 50 mole percent of branched olefins; the lube-oil range hydrocarbon is obtained by separating and hydrogenating the oligomerized olefins.
    Type: Grant
    Filed: May 2, 1983
    Date of Patent: November 20, 1984
    Assignee: Phillips Petroleum Company
    Inventors: William T. Nelson, Ernest A. Zuech
  • Patent number: 4484016
    Abstract: Butene-1 and ethylene mixtures are made by reacting ethylene with a trialkyl aluminum in a boiling bed reactor. The process is more efficient in that it is selective for making butene-1 and more butene-1 is produced per unit weight of the trialkyl aluminum.
    Type: Grant
    Filed: July 5, 1983
    Date of Patent: November 20, 1984
    Assignee: The Dow Chemical Company
    Inventors: Donald M. Maschmeyer, Allan E. Fowler, Steve A. Sims, G. Eldon White
  • Patent number: 4435606
    Abstract: Internal olefins are subjected to metathesis closely coupled after an isomerization reaction to obtain desired molecular weight range linear olefins. Specific process steps and separation conditions are necessary to obtain the desired linear olefins.
    Type: Grant
    Filed: December 24, 1981
    Date of Patent: March 6, 1984
    Assignee: Conoco Inc.
    Inventors: Kaye L. Motz, Paul H. Washecheck, Ronald L. Poe, James E. Yates
  • Patent number: 4380684
    Abstract: A method for preparing C.sub.4 to C.sub.10 .alpha.-olefins employing trialkyl aluminum compounds, in a growth zone having a recirculation rate through an external heat transfer zone such that the contents of the zone are recirculated in a period of time sufficient to remove the heat of the reaction using added lower .alpha.-olefins at 100.degree.-150.degree. C., 200-2000 psig, and 5-90 minute contact time followed by displacement with lower .alpha.-olefins in a static mixer zone to free the growth .alpha.-olefins and regenerate the trialkyl aluminum compounds. The growth .alpha.-olefins are separated with all of the lower .alpha.-olefins recycled to the growth and displacement steps.
    Type: Grant
    Filed: April 19, 1982
    Date of Patent: April 19, 1983
    Assignee: The Dow Chemical Company
    Inventors: Allan E. Fowler, Gordon E. White, Steve A. Sims
  • Patent number: 4314090
    Abstract: A method for preparing C.sub.4 to C.sub.10 .alpha.-olefins having a major portion C.sub.6 .alpha.-olefins employing tri alkyl aluminum compounds, e.g., Al(C.sub.2 H.sub.5).sub.3 or Al(C.sub.4 H.sub.9).sub.3 or mixtures of Al(C.sub.2 H.sub.5).sub.3 and Al(C.sub.4 H.sub.9).sub.3 as well as the unmixed C.sub.2, C.sub.4 alkyl aluminum isomers or homologs in the growth step using added ethylene at about 120.degree. C., 500-700 psig, 5-90 minute contact time followed by displacement with C.sub.2 H.sub.4, C.sub.4 H.sub.8, or C.sub.2 H.sub.4 and C.sub.4 H.sub.8 to free the growth alkyl and regenerate the tri alkyl aluminum compounds. The growth .alpha.-olefins are separated with all of the C.sub.2 H.sub.4 recycled to the growth and displacement steps, and part or all of the C.sub.4 H.sub.8 recycled to the displacement step.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: February 2, 1982
    Assignee: The Dow Chemical Company
    Inventors: William E. Shewbart, Steve A. Sims, Billy D. Head, G. Eldon White