Plural Alkylation Stages Patents (Class 585/449)
  • Patent number: 5157180
    Abstract: A process for producing an alkylated organic compound via alkylation and/or transalkylation in which an organic feedstock is contacted with an organic reactant in the presence of a catalyst under conditions such that components of the organic feedstock react with the organic reactant to form an alkylated compound. The catalyst comprises a molecular sieve having alkylation and/or transalkylation activity and contains, after calcination, between about 250 and 20,000 ppmw ammonium ions, calculated as (NH.sub.4).sub.2 O on a volatiles-free basis. In two preferred embodiments of the invention, the catalyst is employed, respectively, in the alkylation zone of a process for producing cumene via the alkylation of benzene with propylene and in the alkylation zone of a process for producing ethylbenzene via the alkylation of benzene with ethylene.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: October 20, 1992
    Assignee: Union Oil Company of California
    Inventors: Martin West, Suheil F. Abdo
  • Patent number: 5120890
    Abstract: A process is disclosed for reducing benzene and toluene content in light gasoline streams comprising benzene or benzene and toluene but comprising substantially no other aromatic-hydrocarbons. The light gasoline streams may be prepared by distillation of full boiling range gasoline streams from catalytic reforming or fluidized-bed catalytic cracking units. High alkylating agent to benzene ratios are utilized in the presence of a solid alkylation catalyst to achieve a benzene conversion of 70% of more in a single pass through the reaction zone. Alkylating agent is simultaneously injected into the alkylation zone at two or more separate injection points to minimize undersirable side reactions. The alkylation product may be recovered and blended with other gasoline components to produce automotive fuel which is low in benzene content and high octane in rating.
    Type: Grant
    Filed: December 31, 1990
    Date of Patent: June 9, 1992
    Assignee: UOP
    Inventors: J. W. Adriaan Sachtler, R. Joe Lawson
  • Patent number: 5081323
    Abstract: A process for the alkylation or transalkylation of an aromatic hydrocarbon which comprises contacting the aromatic hydrocarbon with a C.sub.2 to C.sub.4 olefin alkylating agent or a polyalkyl aromatic hydrocarbon transalkylating agent, under at least partial liquid phase conditions, and in the presence of a catalyst comprising zeolite beta.
    Type: Grant
    Filed: November 22, 1989
    Date of Patent: January 14, 1992
    Assignee: Chevron Research and Technology Company
    Inventors: Robert A. Innes, Stacey I. Zones, Gerald J. Nacamuli
  • Patent number: 5073653
    Abstract: Process for the alkylation of aromatic substrates with a C.sub.2 -C.sub.4 alkylating agent over an alkylation catalyst comprising zeolite omega at moderate temperature conditions and under pressure to provide liquid phase conditions.The liquid phase alkylation process is carried out using a plurality of series connected reaction stages operated at an average temperature of no more than 300.degree. C. with the interstage injection of the C.sub.2 -C.sub.4 alkylating agent in a manner to maintain at least 2 mole percent of alkylating agent solubilized in the aromatic substrate.The reaction stages of a multistage system temperature and pressure conditions effective to cause are operated at a pressure above the vapor pressure of the aromatic substrate and below the vapor pressure of the alkylating agent at the alkylation reaction conditions.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: December 17, 1991
    Assignee: Fina Technology, Inc.
    Inventor: James R. Butler
  • Patent number: 5043506
    Abstract: An improvement in the operation to a catalytic distillation process for the alkylation of organic aromatic compounds with an olefin contained wherein aliphatic compounds are contained in either the olefin feed stream, the aromatic feed stream or both is disclosed. Aliphatic compounds are added to the upper portion of a secondary distillation column reactor wherein aromatic is being reacted with unreacted olefin from a primary distillation column reactor to polish the conversion of olefin. The additional aliphatic compound produces an equilibrium in the secondary column wherein unreacted aromatic and alkylation product are recovered as bottoms which may be recycled to the primary distillation column reactor.
    Type: Grant
    Filed: September 17, 1990
    Date of Patent: August 27, 1991
    Inventor: Clifford S. Crossland
  • Patent number: 5043501
    Abstract: A process for producing 2,6-dimethylnaphthalene by alkylation of an alkylaromatic, e.g. toluene, with a C.sub.5 olefin alkylating agent, e.g. 1-pentene, in the presence of a suitable alkylation catalyst, and dehydrocyclization of the resulting alkylate with a dehydrocyclization catalyst to generate a dimethylnaphthalene product rich in the 2,6-isomer. Additional process steps can include isomerization of the product and further alkylation.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: August 27, 1991
    Assignee: Mobil Oil Corp.
    Inventors: Kenneth J. Del Rossi, Larry A. Green, Albin Huss, Jr., Garry W. Kirker, Michael E. Landis
  • Patent number: 5003119
    Abstract: A process for the manufacture of alkylbenzenes wherein a feed of fresh and recycle benzene and fresh olefin are reacted in the presence of an alkylation catalyst in an alkylator having at least two reaction stages wherein each stage is adiabatic. Essentially all of the olefin is completely reacted in each stage of the alkylator. Fresh olefin is fed into each stage of the alkylator. Preferred alkylbenzenes which are produced by this process are ethylbenzene and cumene.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: March 26, 1991
    Assignee: Lummus Crest, Inc.
    Inventors: Helion H. Sardina, Roger C. Johnson, John E. Paustian, Renata M. Cox
  • Patent number: 4950834
    Abstract: Cumene is produced in a catalytic distillation column reactor having an upper bed of Omega type molecular sieve catalyst and a lower bed of Y type molecular sieve catalyst. Benzene and propylene are reacted in the upper bed where the Omega type sieve is more selective to cumene that the Y type sieve. Part of the reaction mixture flows down the column to the Y bed where benzene reacts with any unreacted propylene to produce cumene. Additionally, benzene reacts with dipropylbenzene in the Y bed to produce more cumene. Cumene is recovered as bottoms product and unreacted benzene recovered as overheads where it may be returned as reflux to the column to control the mole ratio of benzene to propylene.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: August 21, 1990
    Inventors: Robert P. Arganbright, Dennis Hearn
  • Patent number: 4950824
    Abstract: A process for the production of 2,6-diisopropylnaphthalene is disclosed wherein an isopropylation reaction mixture containing isopropylated naphthalenes is subjected to transalkylation with a triisopropylnaphthalene-containing mixture to obtain a mixture containing mono-, di- and tri-isopropylnaphthalenes which is then separated into a first fraction containing monisopropylnaphthalenes, a second fraction containing diisopropylnaphthalenes and a third fraction containing triisopropylnaphthalenes. The first and third fractions are recycled to the above system, while the second fraction is subjected to separation treatments for the recovery of 2,6-diisopropylnaphthalene. The second fraction from which 2,6-diisopropylnaphthalene has been removed is subjected to transalkylation with naphthalene to obtain a monoisopropylnaphthalene-rich mixture which is to be fed to the isopropylation step.
    Type: Grant
    Filed: August 2, 1989
    Date of Patent: August 21, 1990
    Assignees: Chiyoda Corporation, NKK Corporation
    Inventors: Yoshimi Shiroto, Mitsunori Shimura, Kenji Shimokawa, Yoshio Fukui, Sachio Asaoka, Hiroto Tajima, Kazuaki Ueda, Yakudo Tachibana, Kazuhiko Tate, Hiroaki Taniguchi
  • Patent number: 4922053
    Abstract: A process is disclosed for producing ethylbenzene from the catalytic alkylation of benzene in a multibed reactor wherein a portion of the normal overhead polyethylbenzene recycle stream is diverted into a lower section of the reactor to increase conversion and lower xylene by-product production.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: May 1, 1990
    Assignee: Fina Technology, Inc.
    Inventors: James N. Waguespack, James R. Butler
  • Patent number: 4556750
    Abstract: In an alkylation process a portion of the alkylating olefin is added to benzene before heating the benzene up to the alkylation reaction temperature.
    Type: Grant
    Filed: April 12, 1985
    Date of Patent: December 3, 1985
    Assignee: Phillips Petroleum Company
    Inventor: R. Lynn Cobb
  • Patent number: 4520218
    Abstract: A process is disclosed for producing a mixture of mono- and diallkylated aromatic hydrocarbons suitable for use as a detergent or as a surfactant in enhanced oil recovery processes. Two alkylation reaction stages are used in series, with a separate amount of an acyclic olefin being charged to each reaction stage. The effluent of the second alkylation reaction stage is separated by fractionation to form a mixture of mono- and dialkylated hydrocarbons. A portion of this mixture is recycled to the second alkylation reaction stage, with remainder being withdrawn as the product stream.
    Type: Grant
    Filed: February 23, 1984
    Date of Patent: May 28, 1985
    Assignee: UOP Inc.
    Inventors: Roy C. Berg, Thomas P. Malloy, Bipin V. Vora
  • Patent number: 4343957
    Abstract: Production of cumene by alkylation of benzene with propylene on a solid phosphoric acid catalyst, using in a first step a plurality of catalyst beds in series and in a second step a single catalyst bed, using an overall benzene/propylene molar ratio of at least 5:1, continuously delivering the benzene to the first bed, continuously delivering a series of streams of liquid propylene respectively to the first bed and, in the form of a cold stream, between each pair of contiguous beds, and carrying out a partial recycle of reaction products of the second step as a cold stream between the first and the second step, and using a benzene/propylene molar ratio higher than 13:1 at the inlet of each bed of the first step, and higher than 25:1 at the inlet of the bed of the second step.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: August 10, 1982
    Assignee: Euteco Impianti S.p.A.
    Inventors: Emanuele Sartorio, Benedetto Calcagno, Fulvio Trombetti, Marcello Ghirga
  • Patent number: 4341913
    Abstract: Production of cumene by alkylation of benzene with propylene on a solid phosphoric acid catalyst, using a first step with a plurality of catalyst beds in series and a second step with a single catalyst bed, using an overall benzene/propylene molar ratio of at least 6:1, continuously delivering the benzene to the first bed, continuously delivering a series of streams of liquid propylene respectively to the first bed and, in the form of a cold stream, between each pair of contiguous beds, and using a benzene/propylene molar ratio higher than 16:1 at the inlet of each bed of the first step, and higher than 25:1 at the inlet of the bed of the second step.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: July 27, 1982
    Assignee: Euteco Impianti S.p.A.
    Inventors: Benedetto Calcagno, Emanuele Sartorio, Claudio Divo, Luigi Verde
  • Patent number: 4325807
    Abstract: A multiple stage catalytic conversion system in which a hydrocarbonaceous charge stock and hydrogen flow serially through a plurality of catalytic reaction zones, in each of which the catalyst particles are downwardly movable via gravity flow. At least four reaction zones are utilized, with the fresh feed and hydrogen reactant stream being split between the first and second reaction zones. The flow of that portion introduced into the second zone is restricted. The effluent stream from the first reaction zone is also restricted and then combined with the effluent from the second reaction zone. One portion of the combined effluent streams is introduced into the third reaction zone, and the remaining portion is restricted in flow, combined with the effluent stream from said third reaction zone, and introduced into the fourth reaction zone.
    Type: Grant
    Filed: January 5, 1981
    Date of Patent: April 20, 1982
    Assignee: UOP Inc.
    Inventor: Kenneth D. Peters
  • Patent number: 4325806
    Abstract: A multiple stage catalytic conversion system in which a hydrocarbonaceous charge stock and hydrogen flow serially through a plurality of catalytic reaction zones, in each of which the catalyst particles are downwardly movable via gravity flow. At least three reaction zones are utilized, with the effluent stream from the first reaction zone being split between the second and third reaction zones. The technique decreases mass flow to the second reaction zone, thus serving to alleviate a catalyst pinning problem therein, a situation which occurs when catalyst pinning in the first reaction zone has been alleviated by structural modification methods not available to the second reaction zone.
    Type: Grant
    Filed: January 5, 1981
    Date of Patent: April 20, 1982
    Assignee: UOP Inc.
    Inventor: Kenneth D. Peters
  • Patent number: 4225737
    Abstract: A process is disclosed for the alkylation of an aromatic hydrocarbon with an olefin-acting alkylating agent. The aromatic hydrocarbon is commingled with a first portion of said alkylating agent in a first alkylation reaction zone at alkylation reaction conditions in contact with a hydrofluoric acid catalyst. The acid phase of the effluent from the first alkylation reaction zone is separated, and the hydrocarbon phase, comprising alkylate and unreacted aromatic hydrocarbon is commingled with a second portion of said alkylating agent at alkylation reaction conditions in a second alkylation reaction zone in contact with a hydrofluoric acid catalyst separately charged thereto, the hydrofluoric acid catalyst being that separated from the effluent of the first alkylation reaction zone. The acid phase is separated from the effluent from the second alkylation reaction zone and recycled to the first alkylation reaction zone, and the alkylate product is recovered from the hydrocarbon phase.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: September 30, 1980
    Assignee: UOP Inc.
    Inventors: Michael Z. Mikulicz, James F. Himes