Hf Patents (Class 585/464)
  • Patent number: 8524965
    Abstract: A process for alkylating an aromatic compound comprising reacting at least one aromatic compound with a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, in the presence of an acidic ionic liquid catalyst, wherein the resulting product comprises at least about 50 weight percent of a 1, 2, 4 tri-substituted aromatic compound or a 1, 2, 3 tri-substituted aromatic compound or mixtures thereof.
    Type: Grant
    Filed: December 21, 2005
    Date of Patent: September 3, 2013
    Assignee: Chevron Oronite Company LLC
    Inventors: Curt B. Campbell, Thomas V. Harris, Gilles Sinquin
  • Patent number: 8148591
    Abstract: A process for alkylating an aromatic compound comprising reacting at least one aromatic compound with a mixture of olefins having from about 8 to about 100 carbon atoms, in the presence of a strong acid catalyst wherein the resulting product comprises at least about 60 weight percent of a 1,2,4 tri-alkylsubstituted aromatic compound.
    Type: Grant
    Filed: December 21, 2007
    Date of Patent: April 3, 2012
    Assignees: Chevron Oronite Company LLC, Chevron Oronite S.A.
    Inventors: Gilles P. Sinquin, Curt B. Campbell
  • Patent number: 7972563
    Abstract: A system for alkylating hydrocarbons which includes an improved method of safely handling alkylation catalyst is disclosed. The process includes passing the alkylation catalyst from a settler vessel to a catalyst receiving vessel, via a catalyst cooler, for containment therein in the presence of a condensible gas. Also disclosed is a method for controlling the pressure in the catalyst receiving vessel by controlling the rate of removal of vapors.
    Type: Grant
    Filed: January 27, 2010
    Date of Patent: July 5, 2011
    Assignee: UOP LLC
    Inventors: Keith W. Hovis, Khalid Iqbal, Mark R. Cragun
  • Patent number: 7737312
    Abstract: This invention relates to a process for producing linear alkyl benzene, the process including the steps of obtaining a hydrocarbon condensate containing olefins, paraffins and oxygenates from a low temperature Fischer-Tropsch reaction; a) fractionating a desired carbon number distribution from the hydrocarbon condensate to form a fractionated hydrocarbon condensate stream; b) extracting oxygenates from the fractionated hydrocarbon condensate stream from step (a) to form a stream containing olefins and paraffins; c) combining the stream containing olefins and paraffins from step (b) with the feed stream from step (g) to form a combined stream; d) alkylating olefins in the combined stream from step (c) with benzene in the presence of a suitable alkylation catalyst in an alkylation reactor; e) recovering linear alkyl benzene from the alkylation reactor; f) recovering unreacted paraffins from the alkylation reactor; g) dehydrogenating the unreacted paraffins in the presence of a suitable dehydrogenation catalyst
    Type: Grant
    Filed: March 10, 2004
    Date of Patent: June 15, 2010
    Assignee: Sasol Technology (Proprietary) Limited
    Inventors: Ivan Greager, Jan Hendrik Scholtz, Johan Pieter de Wet, Mieke Ann Desmet, Wilhelmina Jansen, Paul Jacobson, Luis Pablo Fidel Dancuart
  • Patent number: 7518025
    Abstract: A process is provided for producing an alkyl aromatic compound having substituents at the 3- and 5-positions by alkylating an aromatic compound having two substituents in the meta positions with an olefin having 2 to 4 carbon atoms in the presence of a Broensted acid, followed by addition of a Lewis acid and isomerization in the copresence of the Broensted acid and the Lewis acid. According to the present invention, 3,5-dimethylethylbenzene, 3,5-dimethylcumene, etc. may be produced in a stable manner with high yield and high selectivity under mild and simple reaction conditions. The alkyl aromatic compounds having substituents at the 3- and 5-positions are useful as intermediates for functional chemicals for use in pharmaceutical, agricultural and electronic materials. With the method of the present invention, the catalyst used can be recovered and recycled. Thus, desired alkyl aromatic compounds may be obtained economically in an industrially advantageous manner while reducing the load on the environment.
    Type: Grant
    Filed: October 29, 2003
    Date of Patent: April 14, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takeshi Kawai, Kenji Inamasa
  • Patent number: 7495140
    Abstract: A process for alkylating an aromatic compound comprising reacting (a) a first amount of at least one aromatic compound with a first amount of a mixture of olefins having from about 8 to about 100 carbon atoms, in the presence of a strong acid catalyst; and reacting the product of (a) with an additional amount of at least one aromatic compound and an additional amount of a strong acid catalyst, and optionally, with an additional amount of a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, wherein the resulting product comprises at least about 80 weight percent of a 1,2,4 tri-alkylsubstituted aromatic compound.
    Type: Grant
    Filed: June 1, 2006
    Date of Patent: February 24, 2009
    Assignee: Chevron Cronite Company LLC
    Inventors: Curt B. Campbell, Gilles Sinquin
  • Patent number: 7294420
    Abstract: A method of producing hydrogen for a fuel cell from a hydrocarbon fuel composition, by providing a hydrocarbon fuel composition, which is obtained by contacting a liquid hydrocarbon feed comprising an alkylating agent with an acidic catalyst, under conditions effective to alkylate at least a portion of the hydrocarbon feed; converting the hydrocarbon fuel composition into hydrogen; and optionally, introducing the hydrogen produced into a fuel cell. In a preferred embodiment the liquid hydrocarbon feed further comprises sulphur-containing impurities, at least a portion of which are alkylated during the alkylation step.
    Type: Grant
    Filed: August 28, 2002
    Date of Patent: November 13, 2007
    Assignee: BP P.L.C.
    Inventor: Michael Graham Hodges
  • Patent number: 7205445
    Abstract: A method of continuously producing polyalkylbiphenyls involves reacting biphenyl and an olefin in the presence of a solid acid catalyst to obtain a reaction mixture containing monoalkylbiphenyls and dialkylbiphenyls, separating a fraction containing biphenyl and at least a part of the monoalkylbiphenyls, circulating the separated fraction to the reactor such that the ratio of biphenyls to monoalkylbiphenyls is designed to be 0.1 or more and is designed to be less than the soluability of biphenyl to monoalkylbiphenyl at a circulation temperature, and recovering polyalkylbiphenyls.
    Type: Grant
    Filed: August 26, 2003
    Date of Patent: April 17, 2007
    Assignee: Nippon Petrochemicals, Co., Ltd.
    Inventors: Shinichiro Yanagawa, Shouzou Hayashi
  • Patent number: 7148388
    Abstract: In a process for preparing an olefinic hydrocarbon mixture comprising at least 5% by weight of mono-olefin oligomers of the empirical formula: CnH2n where n is greater than or equal to 6, a feedstock comprising n-butene and propylene in a molar ratio of about 1:0.01 to about 1:0.49 is contacted under oligomerization conditions with surface deactivated ZSM-23. The resultant mono-olefin oligomers comprise at least 20 percent by weight of olefins having at least 12 carbon atoms, wherein said olefins having at least 12 carbon atoms have an average of from about 0.8 to about 2.0 C1–C3 alkyl branches per carbon chain.
    Type: Grant
    Filed: March 28, 2003
    Date of Patent: December 12, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Stephen W. Beadle, Cesar M. Cheng-Guajardo, Carolyn B. Duncan, David Wayne Turner, Ramzi Y. Saleh
  • Patent number: 7038099
    Abstract: A method of alkylating aliphatic or aromatic hydrocarbons with olefins using solid hydrogen fluoride-equivalent catalysts is described. Preferred catalysts comprise solid polymeric onium polyhydrogen fluoride complexes.
    Type: Grant
    Filed: November 26, 2003
    Date of Patent: May 2, 2006
    Inventor: George A Olah
  • Patent number: 6787438
    Abstract: A microelectromechanical device is provided which includes a contact structure interposed between a pair of electrodes arranged beneath a beam. In some embodiments, the device may include additional contact structures interposed between the pair of electrodes. For example, the device may include at least three contact structures between the pair of electrodes. In some embodiments, the beam may be suspended above the pair of electrodes by a support structure affixed to a first end of the beam. Such a device may further include an additional support structure affixed to a second end of the beam. In some cases, the device may be adapted to pass a signal from the first end to the second end of the beam. In addition or alternatively, the device may be adapted to pass the signal between one or both ends of the beam and one or more of the contact structures.
    Type: Grant
    Filed: October 16, 2001
    Date of Patent: September 7, 2004
    Assignee: Teravieta Technologies, Inc.
    Inventor: Richard D. Nelson
  • Patent number: 6504072
    Abstract: There is provided a process for the selective production of para-xylene which comprises reacting toluene with methanol in the presence of a catalyst comprising a porous crystalline material having a Diffusion Parameter for 2,2 dimethylbutane of about 0.1-15 sec−1 when measured at a temperature of 120° C. and a 2,2 dimethylbutane pressure of 60 torr (8 kPa). The porous crystalline material is preferably a medium-pore zeolite, particularly ZSM-5, which has been severely steamed at a temperature of at least 950° C. The porous crystalline material is preferably combined with at least one oxide modifier, preferably including phosphorus, to control reduction of the micropore volume of the material during the steaming step.
    Type: Grant
    Filed: May 8, 2002
    Date of Patent: January 7, 2003
    Assignee: ExxonMobil Oil Corporation
    Inventors: Stephen H. Brown, Mark F. Mathias, Robert A. Ware, David H. Olson
  • Patent number: 6248930
    Abstract: This invention concerns fluorine-modified perfluorinated ion-exchange microcomposites, comprising a perfluorinated ion-exchange polymer containing pendant sulphonic acid groups and/or carboxylic acid groups, entrapped within and highly dispersed throughout a network of inorganic oxide, said network having a plurality of fluoride groups bonded thereto; processes for their preparation and their use as catalysts in chemical processes such as alkylation of aromatic compounds.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: June 19, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6137021
    Abstract: A method of converting an HF alkylation process into a solid catalyst alkylation process is disclosed. In this method, an HF alkylation unit having an HF stripper downstream of the HF alkylation reactor is modified to a benzene rectifier. By modifying the HF stripper, this invention not only makes use of the existing HF stripper but also allows the entire downstream product recovery section, which comprises four fractionation columns, to be used in the modified process with only relatively minor modifications. Thus this invention maximizes the use of existing equipment and minimizes the investment necessary to eliminate the use of HF in detergent alkylation.
    Type: Grant
    Filed: August 20, 1999
    Date of Patent: October 24, 2000
    Assignee: UOP LLC
    Inventors: Steven F. Eshelman, Dennis E. O'Brien
  • Patent number: 5942654
    Abstract: A process for the removal of corrosive compounds from a fluid stream, comprising the steps of: in an extraction column with an outer steel tube and an inner tube of corrosion resistant material having an open inlet end and an open outlet end and being arranged coaxially with and spaced apart within at least top portion of the outer tube, introducing at elevated temperature at the inlet end of the inner tube the fluid stream and an extraction agent and effecting in the mixed stream of the fluid and extraction agent extraction of the corrosive compounds; introducing into an annular space between the walls of the outer and the inner tube a shell stream of a non-corrosive fluid, thereby absorbing in the shell stream amounts of the corrosive compounds diffusing through the wall of the inner tube; passing the shell stream to the bottom portion of the outer tube; cooling the mixed stream at the outlet end of the inner tube by introducing into the stream a cooling stream; passing the cooled stream to the bottom porti
    Type: Grant
    Filed: June 13, 1997
    Date of Patent: August 24, 1999
    Assignee: Haldor Topsoe A/S
    Inventor: Sven Ivar Hommeltoft
  • Patent number: 5773549
    Abstract: The invention provides a process for hydrotreating an organic feedstock containing a halogenated component and contaminated with distillable oxygen compounds, and/or distillable nitrogen compounds having boiling points lower than the halogenated compounds by means of removing the distillable oxygen compounds and distillable nitrogen compounds with a fractionation zone and then contacting the resulting organic feedstock having a reduced concentration of distillable oxygen and nitrogen compounds and a gaseous recycle stream containing hydrogen with a hydrogenation catalyst in a hydrogenation reaction zone to produce an anhydrous liquid stream comprising hydrogenated hydrocarbonaceous compounds having a reduced concentration of organic halide and a hydrogen halide compound. The resulting effluent from the hydrogenation zone is optionally separated to produce a hydrogenated hydrocarbonaceous stream having a reduced level of halogen and an anhydrous stream comprising a hydrogen halide compound.
    Type: Grant
    Filed: March 24, 1997
    Date of Patent: June 30, 1998
    Assignee: UOP LLC
    Inventors: Mark D. Moser, Tom N. Kalnes, Chwu-Ching Jan
  • Patent number: 5723706
    Abstract: A process for the conversion of a halogenated organic feedstock to produce a stream of hydrocarbonaceous compounds having an exceedingly low concentration of halogenated organic compounds and an aqueous stream containing hydrogen halide.
    Type: Grant
    Filed: May 30, 1996
    Date of Patent: March 3, 1998
    Assignee: UOP
    Inventors: Robert S. Brasier, Robert B. James, Jr.
  • Patent number: 5705724
    Abstract: A process is disclosed for the production of alkylaromatic compounds employing olefinic liquid from thermally or catalytically cracked plastics as alkylating agent. The process comprises contacting a feedstream comprising alkylatable aromatics and the olefinic liquid with acidic alkylation catalyst under alkylation conditions in an alkylation zone; and recovering an effluent stream comprising alkylaromatic compounds. The alkylation can be performed with the product of plastics pyrolysis or with non-degraded plastic feedstock in-situ with thermal/catalytic degradation of the plastic.
    Type: Grant
    Filed: October 26, 1995
    Date of Patent: January 6, 1998
    Assignee: Mobil Oil Corporation
    Inventors: Nick A. Collins, Larry A. Green, Anagha A. Gupte, David O. Marler, William J. Tracy, III
  • Patent number: 5663474
    Abstract: This invention relates to catalysts for alkylation reactions and their preparation. More particularly, the invention relates to an alkylation process using a hydrogen fluoride-containing alkylation catalyst, which catalyst may be safely and easily handled, transported, and stored.
    Type: Grant
    Filed: March 7, 1996
    Date of Patent: September 2, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Hang Thanh Pham, Robert Pratt, Charles Lewis Redmon, John James Thompson, Michael Van Der Puy, Rajiv Ratna Singh, William James Hague, Harold John Kieta, Matthew Hermes Luly, Jeffrey Warren McKown
  • Patent number: 5489732
    Abstract: Hydrocarbons are alkylated in a fluidized riser-reactor using a solid catalyst which is regenerated within the process by contact with hydrogen. The alkylation and regeneration steps are separated to prevent the admixture of hydrogen and any olefins present in the process. Two separate modes of regeneration are performed simultaneously: a mild liquid-phase washing and a vapor-phase hot hydrogen stripping operation.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: February 6, 1996
    Assignee: UOP
    Inventors: Scott Y. Zhang, Christopher D. Gosling, Paul A. Sechrist, Gregory A. Funk
  • Patent number: 5386073
    Abstract: A shell-and-tube heat exchanger with a tube sheet having partition grooves used to form joints with partition plates contained within the exchanger head. The partition plates define chambers within the head of the exchanger which direct the fluid through the exchanger tubes and which allow for the use of an unequal number of tubes per tube-side pass.
    Type: Grant
    Filed: November 3, 1993
    Date of Patent: January 31, 1995
    Assignee: Phillips Petroleum Company
    Inventors: Tai W. Kwok, Scott D. Love
  • Patent number: 5334793
    Abstract: It has been found that the aromatic byproducts normally formed in the dehydrogenation of normal paraffins to linear monoolefins are detrimental in the usual processes of aromatic alkylation using the dehydrogenation product mixture as an alkylation feedstock. In particular, when solids are used as the alkylation catalysts with recycle of the unreacted feedstock to the dehydrogenation reactor the aromatic byproducts increase to a level where they exert a significant decrease in the stability of the alkylation catalyst. When the aromatic byproducts are removed in whole or in part alkylation may be performed at a substantially lower temperature, which affords alkylated aromatics whose alkyl portion has greater linearity than that observed at a higher alkylation temperature.
    Type: Grant
    Filed: May 27, 1993
    Date of Patent: August 2, 1994
    Assignee: UOP
    Inventor: Joseph A. Kocal
  • Patent number: 5245094
    Abstract: It has been found that the aromatic byproducts normally formed in the dehydrogenation of normal paraffins to linear monoolefins are detrimental in the usual processes of aromatic alkylation using the dehydrogenation product mixture as an alkylation feedstock. In particular, when solids are used as the alkylation catalysts with recycle of the unreacted feedstock to the dehydrogenation reactor the aromatic byproducts increase to a level where they exert a significant decrease in the stability of the alkylation catalyst. When the aromatic byproducts are removed in whole or in part alkylation may be performed at a substantially lower temperature, which affords alkylated aromatics whose alkyl portion has greater linearity than that observed at a higher alkylation temperature.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: September 14, 1993
    Assignee: UOP
    Inventor: Joseph A. Kocal
  • Patent number: 5171915
    Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: December 15, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas R. Forbus, Bruce P. Pelrine
  • Patent number: 5097061
    Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step A of forming p-isobutylstyrene from p-isobutylethylbenzene and a step B of forming .alpha.-(4-isobutylphenyl)propionaldehyde from p-isobutylstyrene or a step C of forming .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester from p-isobutylstyrene.Furthermore, a method for preparing said p-isobutylethylbenzene is also disclosed which comprises alkylating isobutylbenzene or 4-ethyltoluene with ethylene or propylene.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: March 17, 1992
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yuuichi Tokumoto, Kazumichi Uchida
  • Patent number: 4997991
    Abstract: The invention provides an inexpensive synthesis process for preparation of diethynylbenzene monomers that are useful in the preparation of polyacetylenes. This process provides for the preparation of thermally sensitive monomers in a one-pot reaction using readily available materials at low temperatures in an environment capable of absorbing large amounts of energy. Divinylbenzene is first brominated and then dehydrobrominated with sodium hydroxide or potassium hydroxide preferably in the presence of a phase transfer agent followed by distillation to recover the diethylnylbenzene product.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: March 5, 1991
    Assignee: Hercules Incorporated
    Inventors: Lawrence E. Carosino, David C. Herak
  • Patent number: 4982036
    Abstract: An apparatus and a method are disclosed for transferring acid catalyst from a transport vehicle where liquid acid is carried under a relatively low vapor pressure level to a process vessel in an alkylation process where liquid acid is contained at a higher pressure level, while minimizing the loss of acid vapor to the environment. The acid transfer is accomplished without venting the process vessel by employing a relatively small volume pressure lock chamber between the transport vessel and the storage vessel. In a preferred embodiment the small volume pressure lock chamber also serves as a storage vessel for make-up acid which is added to the alkylation process as required.
    Type: Grant
    Filed: September 21, 1989
    Date of Patent: January 1, 1991
    Assignee: Phillips Petroleum Company
    Inventors: Henry K. Hachmuth, Keith W. Hovis
  • Patent number: 4929781
    Abstract: A process for the simultaneous hydroconversion of a first feedstock comprising unsaturated, halogenated organic compounds and a second feedstock comprising saturated, halogenated organic compounds which process comprises: (a) contacting the first feedstock comprising unsaturated, halogenated organic compounds with hydrogen in a first hydrogenation reaction zone operated at hydrogenation conditions selected to minimize the polymerization of unsaturated organic compounds and to produce a first hydrogenated hydrocarbonaceous stream; (b) contacting at least a portion of the first hydrogenated hydrocarbonaceous stream and the second feedstock comprising saturated, halogenated organic compounds with hydrogen in a second hydrogenation reaction zone operated at hydrogenation conditions selected to produce a second hydrogenated hydrocarbonaceous stream and to generate at least one water-soluble hydrogen halide compound; (c) contacting the resulting effluent from the second hydrogenation zone containing hydrogenated hy
    Type: Grant
    Filed: November 30, 1988
    Date of Patent: May 29, 1990
    Assignee: UOP
    Inventors: Robert B. James, Jr., Tom N. Kalnes
  • Patent number: 4891466
    Abstract: A novel liquid acid catalyzed alkylation process utilizing a liquid acid catalyst comprising a surfactant and a liquid acid is disclosed which incorporates a fixed bed of contact material to improve the alkylation reaction zone efficiency. The fixed bed of contact material also allows the process to be efficiently operated at lower acid to olefin mole/mole feed ratios than normally used.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: January 2, 1990
    Assignee: UOP
    Inventor: Joseph A. Kocal
  • Patent number: 4783567
    Abstract: A novel liquid acid catalyzed alkylation process is disclosed which incorporates a fixed bed of contact material to improve the alkylation reaction zone efficiency. The fixed bed of contact material also allows the process to be efficiently operated at lower acid to olefin mole/mole feed ratios than normally used.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: November 8, 1988
    Assignee: UOP Inc.
    Inventor: Joseph A. Kocal
  • Patent number: 4547604
    Abstract: Resorcinol is prepared in high yield and purity by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as acidified Nafion-H, catalyzed cleavage rearrangement reaction of meta-bis(2-hydroperoxy-2-propyl)benzene (meta-diisopropylbenzene dihydroperoxide). Part of the process is the preparation of needed meta-diisopropylbenzene in high purity (98-100%) substantially free of other isomers by treating any mixture of diisopropylbenzenes with an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to eighteen carbon atoms and a Lewis acid fluoride, or by alkylating (transalkylating) cumene with a propyl alkylating agent in the aforementioned superacid systems.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: October 15, 1985
    Assignee: PCUK Produits Chimiques Ugine Kuhlmann
    Inventor: George A. Olah
  • 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: 4520219
    Abstract: A process for producing pseudocueme or durene is described, comprising methylating xylene by the use as a catalyst of at least one crystalline silicate selected from the group consisting of crystalline borosilicate, fluorine-containing crystalline borosilicate, fluorine-containing crystalline aluminosilicate, and fluorine-containing crystalline boroaluminosilicate. The specific crystalline silicate catalyst increases the conversion of xylene and the selectivity of pseudocumene or durene. The process of the invention can be performed either in one step or in two steps. The two-step reaction provides various industrial advantages, such as a high degree of utilization of the methylating agent and a great increase in the selectivity of the product.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: May 28, 1985
    Assignee: Idemitsu Kosan Company Limited
    Inventor: Haruhito Sato
  • Patent number: 4503277
    Abstract: A process is disclosed for the production of alkylaromatic hydrocarbons by the HF-catalyzed reaction of an aromatic hydrocarbon with a C.sub.8 -plus acyclic olefin. The production of linear alkylbenzenes is preferred. The HF is regenerated in a regeneration column in which high boiling compounds are removed from the HF fed to the column. The main stream of HF enters an upper intermediate point in the regeneration column. A second portion of the HF is fed to the top of the regeneration column as reflux. This second portion of HF is withdrawn from the reaction zone rather than from the overhead receiver of the HF regeneration column as in the prior art regeneration method.
    Type: Grant
    Filed: November 30, 1983
    Date of Patent: March 5, 1985
    Assignee: UOP Inc.
    Inventor: James F. Himes
  • Patent number: 4467128
    Abstract: A process is disclosed for the production of alkylaromatic hydrocarbons by the HF catalyzed reaction of an aromatic hydrocarbon with a C.sub.8 -plus acyclic olefin. A portion of the HF used as catalyst is regenerated by passage into a stripping column which has a primary function of stripping dissolved HF out of a hydrocarbonaceous mixture produced in the alkylation zone. This eliminates the requirement for a separate HF regeneration column and the costs associated with this column.
    Type: Grant
    Filed: September 22, 1983
    Date of Patent: August 21, 1984
    Assignee: UOP Inc.
    Inventor: Bipin V. Vora
  • Patent number: 4463205
    Abstract: A process is disclosed for the production of alkylaromatic hydrocarbons by the alkylation of an aromatic hydrocarbon, such as benzene, with a C.sub.8 -plus acyclic olefin which preferably is a normal olefin. The hydrocarbonaceous effluent of the alkylation reaction zone is separated by fractional distillation to yield both a product stream containing monoalkylated aromatics and a small bottoms stream containing dialkylated aromatics and other high boiling compounds but which is substantially devoid of the product monoalkylated aromatics. The product stream is a portion of a sidecut stream withdrawn from the first of two vacuum columns, with a second portion of the sidecut being passed into the second column. The bottoms stream of the first column is also passed into the second column and the overhead vapor of the second column enters an upper portion of the first column.
    Type: Grant
    Filed: September 2, 1983
    Date of Patent: July 31, 1984
    Assignee: UOP Inc.
    Inventor: Joel B. Spinner
  • Patent number: 4311868
    Abstract: Hydrocarbon is catalytically converted by using a fluorine compound represented by the general formula Z.sup.+ MF.sub.6.sup.-, wherein Z is a hydrogen atom or a hydrogen group, and M is a niobium atom, an antimony atom or a tantalum atom as a catalyst, wherein a catalytically inactive component is settled as a heavy liquid phase or deposited as a solid in a reaction product solution from the conversion of hydrocarbon, the heavy liquid phase or the solid is removed from the reaction product solution, thereby removing substantially the catalytically inactive component therefrom, and the remaining catalytically active component is reused in the conversion of hydrocarbon. An amount of a fresh catalyst solution to be supplemented is considerably reduced by effectively reusing the catalytically active component.
    Type: Grant
    Filed: November 20, 1979
    Date of Patent: January 19, 1982
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tamotsu Ueno, Takehiko Takahashi, Kazuo Takada, Toshio Hidaka, Makoto Takagawa
  • Patent number: 4237327
    Abstract: A process for the HF-catalyzed alkylation of aromatic hydrocarbons is disclosed. A first overhead vapor stream removed from a first fractionation column which is used to regenerate the liquid-phase HF is passed directly into an upper intermediate point of a second fractionation column. A hydrocarbon stream containing the feed aromatic hydrocarbon and the product hydrocarbon is separated from liquid-phase HF and is then passed into the second fractionation column. HF dissolved in the hydrocarbon stream is removed from the second column as part of a second overhead vapor stream.
    Type: Grant
    Filed: October 9, 1979
    Date of Patent: December 2, 1980
    Assignee: UOP Inc.
    Inventor: George R. Winter, III
  • Patent number: 4237328
    Abstract: A process for the HF-catalyzed alkylation of aromatic hydrocarbons is disclosed. A liquid-phase alkylation zone effluent stream comprising product alkylaromatic hydrocarbon is passed into an intermediate point of a first fractionation column. A sidecut is removed from the first column at a higher intermediate point and passed into a sidecut stripping column. The bottoms stream of the sidecut stripping column contains the feed aromatic and about 4-10 mole percent paraffinic hydrocarbons and is recycled to the alkylation zone. The overhead vapor stream of the sidecut stripping column is passed into the first column to aid in fractionation.
    Type: Grant
    Filed: October 9, 1979
    Date of Patent: December 2, 1980
    Assignee: UOP Inc.
    Inventor: George R. Winter, III
  • 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