Including An Alkylation Step Patents (Class 585/323)
  • Publication number: 20140378724
    Abstract: A method of making alkylaromatics is described. The process includes recycling a portion of the alkylation reaction zone effluent back to the alkylation zone to maintain the product quality while reducing energy usage.
    Type: Application
    Filed: June 20, 2013
    Publication date: December 25, 2014
    Inventor: Debarshi Majumder
  • Patent number: 8916739
    Abstract: Methods and apparatuses for preparing normal paraffins and hydrocarbon product streams are provided herein. A method of preparing normal paraffins includes providing an unsaturated feed that includes an unsaturated compound that has at least one alkenyl group. The unsaturated feed is epoxidized to convert the at least one alkenyl group in the unsaturated compound to an epoxide functional group, thereby converting the unsaturated compound to an epoxide compound that has at least one epoxide functional group. The at least one epoxide functional group in the epoxide compound is converted to at least one secondary hydroxyl functional group, thereby converting the epoxide compound to a hydroxyl-functional compound that has at least one hydroxyl functional group. The hydroxyl-functional compound is deoxygenated to form normal paraffins.
    Type: Grant
    Filed: December 12, 2012
    Date of Patent: December 23, 2014
    Assignee: UOP LLC
    Inventors: Geoffrey William Fichtl, Daniel Ellig, Stanley Joseph Frey, Michael J. McCall, Andrea G. Bozzano
  • Publication number: 20140364355
    Abstract: A linear alkyl benzene product and production of linear alkylbenzene from a natural oil are provided. A method comprises the step of deoxygenating the natural oils to form a stream comprising paraffins. The paraffins are dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product.
    Type: Application
    Filed: June 6, 2014
    Publication date: December 11, 2014
    Inventors: Stanley J. Frey, Daniel L. Ellig, Andrea G. Bozzano, Geoffrey W. Fichtl, Debarshi Majumder
  • Patent number: 8889937
    Abstract: One exemplary embodiment may be a process for producing one or more alkylated aromatics. Generally, the process includes providing a first stream including an effective amount of benzene for alkylating benzene from a fractionation zone, providing a second stream including an effective amount of ethene for alkylating benzene from a fluid catalytic cracking zone, providing at least a portion of the first and second streams to an alkylation zone; and passing at least a portion of an effluent including ethylbenzene from the alkylation zone downstream of a para-xylene separation zone.
    Type: Grant
    Filed: June 9, 2011
    Date of Patent: November 18, 2014
    Assignee: UOP LLC
    Inventors: Robert Haizmann, Laura E. Leonard, Paula L. Bogdan
  • Patent number: 8884089
    Abstract: The present invention provides a process for producing olefins, comprising: a. cracking an ethane-comprising feed in a cracking zone under cracking conditions to obtain at least olefins and hydrogen; b. converting an oxygenate feedstock in an oxygenate-to-olefin zone to obtain at least olefins; wherein at least part of the oxygenate feedstock is obtained by providing hydrogen obtained in step a) and a feed containing carbon monoxide and/or carbon dioxide to an oxygenate synthesis zone and synthesizing oxygenates. In another aspect the invention provides an integrated system for producing olefins.
    Type: Grant
    Filed: November 9, 2010
    Date of Patent: November 11, 2014
    Assignee: Shell Oil Company
    Inventors: Leslie Andrew Chewter, Jeroen Van Westrenen
  • Patent number: 8877996
    Abstract: Disclosed is a process for the production of alkylated aromatics by contacting a feed stream comprising an alkylatable aromatic, an alkylating agent and trace amounts of water and impurities in the presence of a first catalyst and an alkylation catalyst wherein such water and impurities are removed in order to improve the cycle length of such alkylation catalysts. Water and at least a portion of impurities are removed in a dehydration zone. A reaction zone having a first catalyst which, in some embodiments is a large pore molecular sieve, acts to remove another portion of impurities, such as nitrogenous and other species. An alkylation zone having an alkylation catalyst which, in some embodiments is a medium pore molecular sieve or a MCM-22 family material, acts to remove additional impurities, and to alkylate the alkylatable aromatic compound.
    Type: Grant
    Filed: November 8, 2013
    Date of Patent: November 4, 2014
    Assignees: ExxonMobil Chemical Patents Inc., Technip Process Technology, Inc.
    Inventors: Matthew J. Vincent, Vijay Nanda, Maruti Bhandarkar, Brian Maerz, Terry E. Helton
  • Patent number: 8865956
    Abstract: Embodiments of methods for the production of linear alkylbenzene and optionally biofuel from a natural oil are provided. A method comprises the step of deoxygenating the natural oils to form paraffins. A first portion of the paraffins is hydrocracked to form a first stream of normal and lightly branched paraffins in the C9 to C14 range and a second stream of isoparaffins. The first stream is dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. Optionally a second portion of the paraffins and the isoparaffins are processed to form biofuel.
    Type: Grant
    Filed: July 30, 2013
    Date of Patent: October 21, 2014
    Assignee: UOP LLC
    Inventors: Amarendra Anumakonda, Srikantiah Raghuram, Joao Jorge da Sllva Ferreira Alves, Andrea G. Bozzano
  • Patent number: 8853479
    Abstract: Embodiments of methods for production of linear alkylbenzene and optionally biofuel from natural oil are provided. Natural oils are deoxygenated to form a stream comprising paraffins. A first portion of the paraffins are dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. Optionally, a second portion of the paraffins may be processed to form biofuel.
    Type: Grant
    Filed: July 30, 2013
    Date of Patent: October 7, 2014
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Matthew J. Griffiths, Amarendra Anumakonda
  • Patent number: 8853482
    Abstract: In a process for dealkylating a poly-alkylated aromatic compound, a feed comprising at least one poly-alkylated aromatic compound selected from polypropylbenzene, polybutylbenzene, and polycyclohexylbenzene is introduced into a reaction zone. The feed is then contacted in the reaction zone with an acid catalyst under conditions effective to dealkylate at least a portion of the poly-alkylated aromatic compound and produce a first reaction product comprising at least one mono-alkylated aromatic compound.
    Type: Grant
    Filed: February 3, 2011
    Date of Patent: October 7, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kun Wang, James R. Lattner
  • Publication number: 20140256010
    Abstract: A method for converting an alcohol to a hydrocarbon fraction having a lowered benzene content, the method comprising: converting said alcohol to a hydrocarbon fraction by contacting said alcohol, under conditions suitable for converting said alcohol to said hydrocarbon fraction, with a metal-loaded zeolite catalyst catalytically active for converting said alcohol to said hydrocarbon fraction, and contacting said hydrocarbon fraction with a benzene alkylation catalyst, under conditions suitable for alkylating benzene, to form alkylated benzene product in said hydrocarbon fraction. Also described is a catalyst composition useful in the method, comprising a mixture of (i) a metal-loaded zeolite catalyst catalytically active for converting said alcohol to said hydrocarbon, and (ii) a benzene alkylation catalyst, in which (i) and (ii) may be in a mixed or separated state. A reactor for housing the catalyst and conducting the reaction is also described.
    Type: Application
    Filed: March 6, 2013
    Publication date: September 11, 2014
    Applicant: UT-BATTELLE, LLC
    Inventors: Chaitanya K. Narula, Brian H. Davison, Martin Keller
  • Publication number: 20140243567
    Abstract: The present invention provides a process for producing a monoalkylated benzene comprising the step of contacting benzene with an alkylating agent in the presence of a catalyst composition under effective alkylation conditions to form said monoalkylated benzene and polyalkylated benzene, said catalyst composition comprising MCM-56 and a binder, such that the crystal/binder weight ratio in said catalyst composition is from about 20/80 to about 80/20, wherein said polyalkylated benzene comprises dialkylated benzene and trialkylated benzene, and the weight ratio of trialkylated benzene to dialkylated benzene is in the range from about 0.08 to about 0.12.
    Type: Application
    Filed: May 2, 2014
    Publication date: August 28, 2014
    Inventors: Matthew J. Vincent, Terry E. Helton, Ivy D. Johnson
  • Patent number: 8802907
    Abstract: A processes for producing a dehydrogenation reaction product stream comprising the step of contacting a hydrocarbon stream comprising cyclohexane and methyl cyclopentane with a dehydrogenation catalyst comprising at least one metal or compound thereof and at least one molecular sieve and under conditions effective to convert at least a portion of the cyclohexane to benzene and to convert at least a portion of the methyl cyclopentane to at least one paraffin. The hydrocarbon stream is produced by hydroalkylating benzene and hydrogen to form a hydroalkylation reaction product stream which is separated to yield the hydrocarbon stream.
    Type: Grant
    Filed: December 17, 2010
    Date of Patent: August 12, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Teng Xu, Edward A. Lemon, Jr., Tan-Jen Chen, Terry E. Helton
  • Patent number: 8796498
    Abstract: A process is disclosed for making styrene by converting methanol to formaldehyde in a reactor then reacting the formaldehyde with toluene to form styrene in a separate reactor.
    Type: Grant
    Filed: December 2, 2013
    Date of Patent: August 5, 2014
    Assignee: Fina Technology, Inc.
    Inventors: James R. Butler, Joseph E. Pelati
  • Publication number: 20140163278
    Abstract: Methods and apparatuses for preparing normal paraffins and hydrocarbon product streams are provided herein. A method of preparing normal paraffins includes providing an unsaturated feed that includes an unsaturated compound that has at least one alkenyl group. The unsaturated feed is epoxidized to convert the at least one alkenyl group in the unsaturated compound to an epoxide functional group, thereby converting the unsaturated compound to an epoxide compound that has at least one epoxide functional group. The at least one epoxide functional group in the epoxide compound is converted to at least one secondary hydroxyl functional group, thereby converting the epoxide compound to a hydroxyl-functional compound that has at least one hydroxyl functional group. The hydroxyl-functional compound is deoxygenated to form normal paraffins.
    Type: Application
    Filed: December 12, 2012
    Publication date: June 12, 2014
    Applicant: UOP LLC
    Inventors: Geoffrey William Fichtl, Daniel Ellig, Stanley Joseph Frey, Michael J. McCall, Andrea G. Bozzano
  • Patent number: 8747785
    Abstract: The apparatus converts ethylene in a dilute ethylene stream and dilute benzene in an aromatic containing stream via alkylation to heavier hydrocarbons. The catalyst may be a zeolite such as UZM-8. The catalyst is resistant to feed impurities such as hydrogen sulfide, carbon oxides, and hydrogen and selectively converts benzene. At least 40 wt-% of the ethylene in the dilute ethylene stream and at least 20 wt-% of the benzene in the dilute benzene stream can be converted to heavier hydrocarbons.
    Type: Grant
    Filed: April 8, 2013
    Date of Patent: June 10, 2014
    Assignee: UOP LLC
    Inventors: Christopher P. Nicholas, Alakananda Bhattacharyya
  • Patent number: 8735515
    Abstract: A process is disclosed for producing plastic materials by providing a biology based feedstock and reacting the biology based feedstock to form a feedstock capable of reaction to form the plastic material, wherein the plastic material is selected from polystyrene and polyethylene terephthalate (PET).
    Type: Grant
    Filed: July 27, 2011
    Date of Patent: May 27, 2014
    Assignee: Fina Technology, Inc.
    Inventors: Scott Cooper, Olga Khabashesku
  • Publication number: 20140135548
    Abstract: Disclosed is a process for the production of alkylated aromatics by contacting a feed stream comprising an alkylatable aromatic, an alkylating agent and trace amounts of water and impurities in the presence of a first catalyst and an alkylation catalyst wherein such water and impurities are removed in order to improve the cycle length of such alkylation catalysts. Water and at least a portion of impurities are removed in a dehydration zone. A reaction zone having a first catalyst which, in some embodiments is a large pore molecular sieve, acts to remove another portion of impurities, such as nitrogenous and other species. An alkylation zone having an alkylation catalyst which, in some embodiments is a medium pore molecular sieve or a MCM-22 family material, acts to remove additional impurities, and to alkylate the alkylatable aromatic compound.
    Type: Application
    Filed: November 8, 2013
    Publication date: May 15, 2014
    Inventors: Matthew J. Vincent, Vijay Nanda, Maruti Bhandarkar, Brian Maerz, Terry E. Helton
  • Patent number: 8722951
    Abstract: This invention relates to fuel compositions for use in combustion engines, such as for motor vehicle and aircraft usage. The fuel composition contains at least 99.5% of aromatic hydrocarbons and paraffinic hydrocarbons. The composition also preferably contains no lead, no multi-ring compound (only single ring compounds are present), less than about 15 ppm sulfur, and/or less than about 5 ppm nitrogen species. The resulting fuel is a drop-in fuel that provides clean burning with little to no engine deposit, high lubricity, high stability, and low corrosion.
    Type: Grant
    Filed: July 12, 2013
    Date of Patent: May 13, 2014
    Assignee: Primus Green Energy Inc.
    Inventors: Howard L. Fang, Meifang Qin, Moshe Ben-Reuven
  • Publication number: 20140121431
    Abstract: A method for alkylation of a feedstock is described. The method includes contacting the feedstock comprising at least one alkylatable aromatic compound and an alkylating agent with a first alkylating catalyst composition under alkylating conditions, the first alkylating catalyst composition comprising UZM-8 zeolite and a binder, the first alkylating catalyst composition having less than 50 wt % UZM-8 zeolite; wherein a total alkylated selectivity at a temperature and a molar ratio of alkylatable aromatic compound to alkylating agent is greater than 99.0%.
    Type: Application
    Filed: October 26, 2012
    Publication date: May 1, 2014
    Applicant: UOP LLC
    Inventors: Deng-Yang Jan, Robert J. Schmidt, Pelin Cox
  • Patent number: 8704021
    Abstract: The process converts FCC olefins to heavier compounds. The heavier compounds are more easily separated from the unconverted paraffins. The heavier compounds can be recycled to an FCC unit or delivered to a separate FCC unit. Suitable conversion zones are oligomerization and aromatic alkylation zones.
    Type: Grant
    Filed: May 23, 2013
    Date of Patent: April 22, 2014
    Assignee: UOP LLC
    Inventors: Joao Jorge da Silva Ferreira Alves, James E. Rekoske, Christopher P. Nicholas
  • Publication number: 20140094631
    Abstract: A process is disclosed for making styrene by converting methanol to formaldehyde in a reactor then reacting the formaldehyde with toluene to form styrene in a separate reactor.
    Type: Application
    Filed: December 2, 2013
    Publication date: April 3, 2014
    Applicant: FINA TECHNOLOGY, INC.
    Inventors: James R. Butler, Joseph E. Pelati
  • Publication number: 20140058143
    Abstract: The present invention relates to a 3,3?,4,4?-tetraalkyl cyclohexylbenzene represented by the general formula (1): wherein R represents an alkyl group having 1 to 4 carbon atoms, which may be easily converted into a 3,3?,4,4?-biphenyltetracarboxylic acid and a 3,3?,4,4?-biphenyltetracarboxylic dianhydride thereof, which are a starting material for a polyimide, via a 3,3?,4,4?-tetraalkylbiphenyl; and a method for producing the same.
    Type: Application
    Filed: May 18, 2012
    Publication date: February 27, 2014
    Applicant: UBE INDUSTRIES, LTD.
    Inventors: Yasushi Yamamoto, Hikaru Yatabe
  • Patent number: 8633342
    Abstract: In a process for alkylation of an alkylatable aromatic compound to produce a monoalkylated aromatic compound, a first feed stream comprising fresh alkylatable aromatic compound is passed to a first reaction zone which comprises a transalkylation catalyst and which also receives a second feed stream comprising polyalkylated aromatic compounds. The first and second feed streams are contacted with the transalkylation catalyst in the first reaction zone under conditions to transalkylate the polyalkylated aromatic compounds with the alkylatable aromatic compound to produce the desired monoalkylated aromatic compound. A first effluent stream comprising unreacted alkylatable aromatic compound and the monoalkylated aromatic compound is removed from the first reaction zone and passed to a fractionation system to separate the first effluent stream into a first light fraction comprising the unreacted alkylatable aromatic compound and a first heavy fraction comprising the monoalkylated aromatic compound.
    Type: Grant
    Filed: September 24, 2009
    Date of Patent: January 21, 2014
    Assignee: Badger Licensing LLC
    Inventors: Matthew J. Vincent, Charles Morris Smith
  • Patent number: 8629311
    Abstract: Disclosed is a process for the production of alkylated aromatics by contacting a feed stream comprising an alkylatable aromatic, an alkylating agent and trace amounts of water and impurities in the presence of first and second alkylation catalysts wherein the water and impurities are removed in order to improve the cycle length of such alkylation catalysts. Water and a portion of impurities are removed in a dehydration zone. A first alkylation zone having a first alkylation catalyst which, in some embodiments is a large pore molecular sieve, acts to remove a larger portion of impurities, such as nitrogenous and other species, and to alkylate a smaller portion of the alkylatable aromatic compound. A second alkylation zone, which in some embodiments is a medium pore molecular sieve, acts to remove a smaller portion of impurities, and to alkylate a larger portion of the alkylatable aromatic compound.
    Type: Grant
    Filed: March 10, 2010
    Date of Patent: January 14, 2014
    Assignees: Stone & Webster, Inc., ExxonMobil Chemical Patents Inc.
    Inventors: Matthew J. Vincent, Vijay Nanda, Maruti Bhandarkar, Brian Maerz, Terry E. Helton
  • 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
  • Patent number: 8618342
    Abstract: A process for the production of a mixture of alkylbenzenes in the presence of an aromatic feedstock and an olefinic stream produced from an ethylene feedstock is described, with said process comprising at least: a) A first stage for oligomerization of said ethylene feedstock that consists of at least one hydrocarbon effluent that comprises a mixture of olefins having a number of carbon atoms that is for the most part between 4 and 30, whereby said mixture of olefins comprises a C10-C24 olefinic fraction that has a mean linearity that is greater than 60%, in the presence of a homogeneous catalytic system, b) A second stage for oligomerization of the effluent that is obtained from said stage a) that consists of at least one hydrocarbon effluent that comprises a mixture of olefins having a number of carbon atoms that is for the most part between 4 and 30, whereby said mixture of olefins comprises a C10-C24 olefinic fraction that has a mean linearity that is less than 50%, in the presence of a homogeneous cata
    Type: Grant
    Filed: May 5, 2011
    Date of Patent: December 31, 2013
    Assignee: IFP Energies nouvelles
    Inventors: Emmanuelle Guillon, Eric Sanchez
  • Publication number: 20130338417
    Abstract: Disclosed is a method for removing weakly basic nitrogen compounds from a hydrocarbon feed stream by contacting the hydrocarbon feed stream with a basic catalyst to convert a portion of the weakly basic nitrogen compounds to basic nitrogen compounds. The method also includes contacting the hydrocarbon feed stream with an acidic adsorbent to adsorb the basic nitrogen compounds from the stream. The hydrocarbon feed stream comprises an aromatic compound and a weakly basic nitrogen compound.
    Type: Application
    Filed: June 14, 2013
    Publication date: December 19, 2013
    Inventors: Mark G. Riley, Wugeng Liang, Deng-Yang Jan, Adam Gross
  • Publication number: 20130338416
    Abstract: Disclosed is a method for removing weakly basic nitrogen compounds from a hydrocarbon feed stream by contacting the hydrocarbon feed stream with acidic clay to produce a hydrocarbon effluent stream having a lower weakly basic nitrogen compound content relative to the hydrocarbon feed stream. The hydrocarbon feed stream comprises an aromatic compound and a weakly basic nitrogen compound.
    Type: Application
    Filed: June 14, 2013
    Publication date: December 19, 2013
    Inventors: Mark G. Riley, Wugeng Liang, Deng-Yang Jan, Adam Gross
  • Publication number: 20130324776
    Abstract: A process is disclosed for alkylating benzene contained in a benzene-containing refinery gasoline stream also comprising at least 0.1 wt % of at least one C6 to C8 olefin. In the process, the refinery gasoline stream is contacted under alkylation conditions with an alkylating agent selected from one or more C2 to C5 olefins in at least a first alkylation reaction zone and a second alkylation reaction zone connected in series to produce an alkylated effluent, which has reduced benzene content as compared with said refinery gasoline stream. All of the refinery gasoline stream is introduced into the first alkylation reaction stage, whereas an aliquot of the alkylated effluent is recycled and introduced to the second, but not the first, alkylation reaction zone.
    Type: Application
    Filed: November 30, 2011
    Publication date: December 5, 2013
    Applicant: BADGER LICENSING LLC
    Inventors: Shyh-Yuan H. Hwang, Ronald Birkhoff, Richard F. Guarino, J. Erik Moy, Joseph C. Peters
  • Publication number: 20130317267
    Abstract: Embodiments of methods for the production of linear alkylbenzene and optionally biofuel from a natural oil are provided. A method comprises the step of deoxygenating the natural oils to form paraffins. A first portion of the paraffins is hydrocracked to form a first stream of normal and lightly branched paraffins in the C9 to C14 range and a second stream of isoparaffins. The first stream is dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. Optionally a second portion of the paraffins and the isoparaffins are processed to form biofuel.
    Type: Application
    Filed: July 30, 2013
    Publication date: November 28, 2013
    Applicant: UOP LLC
    Inventors: Amarendra Anumakonda, Srikantiah Raghuram, Joao Jorge da SIlva Ferreira Alves, Andrea G. Bozzano
  • Publication number: 20130317268
    Abstract: Embodiments of methods for production of linear alkylbenzene and optionally biofuel from natural oil are provided. Natural oils are deoxygenated to form a stream comprising paraffins. A first portion of the paraffins are dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. Optionally, a second portion of the paraffins may be processed to form biofuel.
    Type: Application
    Filed: July 30, 2013
    Publication date: November 28, 2013
    Inventors: Andrea G. Bozzano, Matthew J. Griffiths, Amarendra Anumakonda
  • Patent number: 8558046
    Abstract: The present invention is for a process for the alkylation of aromatic compounds, with a shape-selective zeolite catalyst. The process has reactors in series with C8+ aromatics being separated from the product stream effluents from each reactor before passing the reactor effluent to the next reactor with an additional input of methanol. The C8+ aromatics are separated into para-xylene and other C8+ aromatics. This process is applicable for toluene methylation having a molar excess of toluene:methanol. i.e., greater than 1:1, with a shape-selective catalyst of an aluminosilicate zeolite, such as ZSM-5 which has been modified with phosphorus, to produce para-xylene (p-xylene).
    Type: Grant
    Filed: May 28, 2009
    Date of Patent: October 15, 2013
    Assignee: Saudi Basic Industries Corporation
    Inventors: Frederick Merrill Galloway, Jr., Ashim Kumar Ghosh, Mohammad Shafiei, Peter N. Loezos
  • Patent number: 8546629
    Abstract: Embodiments of methods for co-production of linear alkylbenzene and biofuel from a natural oil are provided. A method comprises the step of deoxygenating the natural oils to form a stream comprising paraffins. A first portion of the paraffins are dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. A second portion of the paraffins is processed to form biofuel.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: October 1, 2013
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Matthew James Griffiths, Amarendra Anumakonda
  • Publication number: 20130253242
    Abstract: The present invention relates to a method for manufacturing aromatic products (benzene/toluene/xylene) and olefinic products from an aromatic-compound-containing oil fraction, whereby it is possible to substitute naphtha as a feedstock for aromatic production and so make stable supply and demand, and it is possible to substantially increase the yield of high-added-value olefinic and high-added-value aromatic components, by providing a method for manufacturing olefinic and aromatic products from light cycle oil comprising a hydrogen-processing reaction step, a catalytic cracking step, an separation step and a transalkylation step, and optionally also comprising a recirculation step.
    Type: Application
    Filed: November 25, 2010
    Publication date: September 26, 2013
    Applicant: SK INNOVATION CO., LTD.
    Inventors: Hong Chan Kim, Sung Won Kim, Yong Seung Kim, Sang Hun Oh, Soo Kil Kang, Hyuck Jae Lee, Cheol Joong Kim, Gyung Rok Kim, Sun Choi, Sam Ryong Park
  • Publication number: 20130253239
    Abstract: A process for producing heavy alkyl aromatics is presented. The process utilizes low molecular weight hydrocarbons for generating larger alkyl groups. The hydrocarbons can be generated from a variety of sources including Fischer-Tropsch liquids. The process includes oligomerization of low molecular weight olefins to larger olefins. The larger olefins are passed to an alkylation reactor to alkylate aromatic compounds.
    Type: Application
    Filed: March 23, 2012
    Publication date: September 26, 2013
    Applicant: UOP LLC
    Inventors: Andrea G. Bozzano, Jeffery C. Bricker, Bryan K. Glover
  • Publication number: 20130245347
    Abstract: A method for alkylating aromatic compounds is described using an electrochemical decarboxylation process. This process produces aryl-alkyl compounds that have properties useful in Group V lubricants (and other products) from abundant and economical carboxylic acids. The process presented here is also advantageous as it is conducted at moderate temperatures and conditions, without the need of a catalyst. The electrochemical decarboxylation has only H2 and CO2 as its by-products, as opposed to halide by-products.
    Type: Application
    Filed: March 15, 2013
    Publication date: September 19, 2013
    Applicant: CERAMATEC, INC.
    Inventors: James Mosby, Patrick McGuire, Sai Bhavaraju, Mukund Karanjikar
  • Publication number: 20130237733
    Abstract: Processes for preparing alkylation aromatic compounds are provided herein. In an embodiment, a process for preparing alkylated aromatic compounds includes reacting an aromatic compound and an olefin in a first alkylation reaction in the presence of a first alkylation catalyst to produce a first effluent that includes an alkylated aromatic compound and unreacted aromatic compound. Unreacted aromatic compound from the first effluent and additional olefin are reacted in at least one downstream alkylation reaction in the presence of a second alkylation catalyst to produce a second effluent including the alkylated aromatic compound. A recycle stream including the alkylated aromatic compound is recycled from the second effluent to the at least one downstream alkylation reaction and, optionally, the first alkylation reaction. A ratio of the recycle stream to a total mass flow is greater in the at least one downstream alkylation reaction than in the first alkylation reaction.
    Type: Application
    Filed: March 12, 2012
    Publication date: September 12, 2013
    Applicant: UOP LLC
    Inventors: Debarshi Majumder, Carl John Stevens, Robert James Schmidt
  • Patent number: 8524967
    Abstract: A process for producing a monoalkylated aromatic compound in an alkylation reaction zone, said process comprising the steps of: (a) providing a first catalytic particulate material which comprises MCM-56 and having a ratio of surface area over volume ratio greater than about 79 cm?1, (b) providing said alkylation reaction zone with an alkylatable aromatic compound, an alkylating agent, and said first catalytic particulate material; and (c) contacting said alkylatable aromatic compound and said alkylating agent with said catalytic particulate material in said alkylation reaction zone maintained under alkylation conditions, to form a product comprised of said monoalkylated aromatic compound and polyalkylated aromatic compound(s).
    Type: Grant
    Filed: November 14, 2012
    Date of Patent: September 3, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Michael C. Clark, Frederick Y. Lo, Christine N. Elia, Yun-Feng Chang
  • Publication number: 20130225888
    Abstract: Alkylation systems and methods of minimizing alkylation catalyst regeneration are described herein. The alkylation systems generally include a preliminary alkylation system adapted to receive an input stream including an alkyl aromatic hydrocarbon and contact the input stream with a preliminary alkylation catalyst disposed therein to form a first output stream. The preliminary alkylation catalyst generally includes a zeolite catalyst having a SiO2/Al2O3 ratio of less than about 25. The alkylation systems further include a first alkylation system adapted to receive the first output stream and contact the first output stream with a first alkylation catalyst disposed therein and an alkylating agent to form a second output stream.
    Type: Application
    Filed: April 16, 2013
    Publication date: August 29, 2013
    Applicant: FINA TECHNOLOGY, INC.
    Inventors: James R. Butler, Xin Xiao, James T. Merrill
  • Patent number: 8519208
    Abstract: Processes for catalytically synthesizing ethylbenzene from ethanol and benzene comprising: 1) reacting a first mixture comprising ethanol and benzene with at least one catalyst chosen from binder-containing alkylation catalysts and binder-free alkylation catalysts in an alkylation reactor to obtain a second mixture comprising residual benzene, ethylbenzene, diethylbenzene, and water; 2) passing the second mixture successively through a benzene recovery tower, an ethylbenzene recovery tower, and a polyethylbenzene recovery tower to obtain separated water, separated benzene, separated ethylbenzene, and separated diethylbenzene; and 3) reacting a third mixture with at least one transalkylation catalyst in a transalkylation reactor, wherein the third mixture comprises at least some of the separated benzene and at least some of the separated diethylbenzene at a weight ratio ranging from about 2:1 to about 10:1.
    Type: Grant
    Filed: June 13, 2011
    Date of Patent: August 27, 2013
    Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology, Sinopec
    Inventors: Weimin Yang, Hongmin Sun, Wenjie Liu, Bin Zhang, Zhenhao Shen, Mingyao Huan, Hongyu Zhang
  • Patent number: 8519209
    Abstract: A process is presented for controlling the output of monoalkylated benzenes. The alkylbenzenes are linear alkylbenzenes and the process controls the 2-phenyl content of the product stream. The control of the process to generate a linear alkylbenzene with a 2-phenyl content within a desired range by recycling a portion of the effluent from the alkylation reactor to the inlet of the reactor.
    Type: Grant
    Filed: February 27, 2013
    Date of Patent: August 27, 2013
    Assignee: UOP LLC
    Inventors: Mark G. Riley, Stephen W. Sohn, Deng-Yang Jan
  • Publication number: 20130217937
    Abstract: Alkylation systems and methods of minimizing alkylation catalyst regeneration are discussed herein. The alkylation systems generally include a preliminary alkylation system adapted to receive an input stream including an alkyl aromatic hydrocarbon and contact the input stream with a first preliminary alkylation catalyst disposed therein to form a first output stream. The first preliminary alkylation catalyst generally includes a Y zeolite. The systems further include a first alkylation system adapted to receive the first output stream and contact the first output stream with a first alkylation catalyst disposed therein and an alkylating agent to form a second output stream.
    Type: Application
    Filed: March 19, 2013
    Publication date: August 22, 2013
    Applicant: FINA TECHNOLOGY, INC.
    Inventors: James T. Merrill, Marcus Ledoux
  • Publication number: 20130211164
    Abstract: The present invention provides an improved process for producing an alkylated aromatic compound from an at least partially untreated alkylatable aromatic compound having catalyst poisons and an alkylating agent, wherein said alkylatable aromatic compound stream is treated to reduce catalyst poisons with a treatment composition having a surface area/surface volume ratio of greater than or equal to 30 in?1 (12 cm?1) in a treatment zone separate from an alkylation reaction zone under treatment conditions including a temperature of from about 30° C. to about 300° C. to form an effluent comprising said treated alkylatable aromatic compound.
    Type: Application
    Filed: April 15, 2011
    Publication date: August 15, 2013
    Inventors: Matthew J. Vincent, Vijay Nanda, Terry E. Helton
  • Patent number: 8507741
    Abstract: Embodiments of methods for co-production of linear alkylbenzene and biofuel from a natural oil are provided. A method comprises the step of deoxygenating the natural oils to form paraffins. A first portion of the paraffins is hydrocracked to form a first stream of normal and lightly branched paraffins in the C9 to C14 range and a second stream of isoparaffins. The first stream is dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. A second portion of the paraffins and the isoparaffins are processed to form biofuel.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: August 13, 2013
    Assignee: UOP LLC
    Inventors: Amarendra Anumakonda, Srikantiah Raghuram, Joao Jorge da Silva Ferreira Alves, Andrea G. Bozzano
  • Patent number: 8507396
    Abstract: A process for regenerating a used acidic catalyst which has been deactivated by conjunct polymers by removing the conjunct polymers so as to increase the activity of the catalyst is disclosed. Methods for removing the conjunct polymers include addition of a basic reagent and alkylation. The methods are applicable to all acidic catalysts and are described with reference to certain ionic liquid catalysts.
    Type: Grant
    Filed: April 20, 2010
    Date of Patent: August 13, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Thomas V. Harris
  • Patent number: 8502005
    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: March 22, 2012
    Date of Patent: August 6, 2013
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Stephen Wayne Sohn
  • Publication number: 20130197287
    Abstract: The present invention provides an improved process for producing an alkylated aromatic compound from an at least partially untreated alkylatable aromatic compound having catalyst poisons, wherein said alkylatable aromatic compound stream is treated to reduce catalyst poisons with a treatment composition having a surface area/surface volume ratio of greater than or equal to 30 in?1 (12 cm?1) in a treatment zone separate from an alkylation reaction zone under treatment conditions including a temperature of from about 30° C. to about 300° C. to form an effluent comprising said treated alkylatable aromatic compound.
    Type: Application
    Filed: April 15, 2011
    Publication date: August 1, 2013
    Inventors: Matthew J. Vincent, Vijay Nanda, Terry E. Helton
  • Publication number: 20130172646
    Abstract: A process is presented for controlling the output of monoalkylated benzenes. The alkylbenzenes are linear alkylbenzenes and the process controls the 2-phenyl content of the product stream. The control of the process to generate a linear alkylbenzene with a 2-phenyl content within a desired range by recycling a portion of the effluent from the alkylation reactor to the inlet of the reactor.
    Type: Application
    Filed: February 27, 2013
    Publication date: July 4, 2013
    Applicant: UOP LLC
    Inventor: UOP LLC
  • Patent number: 8461405
    Abstract: A process for the production of alkylbenzenes in the presence of an aromatic feedstock and an olefinic stream produced from an ethanol feedstock, itself produced from a renewable source obtained from biomass, is described, with said process comprising at least: a) A stage for purification of said ethanol feedstock, b) A stage for dehydration of said purified ethanol feedstock, obtained from said stage a), into an effluent that is for the most part ethylene, c) At least one stage for separation of the water that is present in said effluent that is for the most part ethylene obtained from said stage b), d) A first stage for oligomerization of said effluent that is for the most part ethylene in the presence of at least one catalyst that comprises at least one element of group VIII, e) A second stage for oligomerization of at least some of the effluent that is obtained from said stage d) in the presence of at least one amorphous catalyst or at least one zeolitic catalyst, f) A stage for fractionation of the ef
    Type: Grant
    Filed: May 4, 2011
    Date of Patent: June 11, 2013
    Assignee: IFP Energies nouvelles
    Inventors: Eric Sanchez, Emmanuelle Guillon
  • Patent number: 8461404
    Abstract: A prolongated silica bound zeolite support comprising from about 85 wt % to about 95 wt % zeolite. A catalyst composition comprising a prolongated silica bound zeolite supporting at least one Group VIII metal and at least one halide. A process of making a prolongated silica bound zeolite support comprising mixing a zeolite, a prolongated silica, and water to form a mixture, and shaping the mixture into the prolongated silica bound zeolite support. A process of making a prolongated silica bound zeolite catalyst comprising mixing a zeolite, a prolongated silica, and water to form a mixture, shaping the mixture into a prolongated silica bound zeolite support, and adding one or more catalytic compounds to the prolongated silica bound zeolite support to form the prolongated silica bound zeolite catalyst.
    Type: Grant
    Filed: February 16, 2011
    Date of Patent: June 11, 2013
    Assignee: Chevron Phillips Chemical Company LP
    Inventor: Gyanesh P. Khare