Resulting Side-chain Restricted To More Than Five C Atoms, E.g., "detergent Alkylate", Etc. Patents (Class 585/455)
  • Patent number: 10774016
    Abstract: A method for reducing the mutagenicity of polycyclic aromatic compounds (PAC's) having one or more bay regions which involves alkylating the PAC's with an alkylating agent in the presence of a catalyst to lower the mutagenicity down to as much as about 0.1. The resulting alkylated polycyclic aromatic compounds retain their physical and chemical properties for safe industrial use including as rubber processing oils, inks, etc.
    Type: Grant
    Filed: March 9, 2018
    Date of Patent: September 15, 2020
    Assignee: Heritage Research Group
    Inventors: Anthony J. Kriech, Julia Austin, Matthew Kriech
  • Patent number: 10427144
    Abstract: A new family of crystalline microporous metalloalumino(gallo)phosphosilicates designated MeAPSO-83 has been synthesized. These metalloalumino(gallo)phosphosilicates are represented by the empirical formula of: Rp+rA+mM2+wExPSiyOz where A is an alkali metal such as potassium, R is an quaternary ammonium cation such as ethyltrimethylammonium, M is a divalent metal such as Zn and E is a trivalent framework element such as aluminum or gallium. This family of metalloalumino(gallo)phosphosilicate materials are stabilized by combinations of alkali and quaternary ammonium cations, enabling unique, high charge density compositions. The MeAPSO-83 family of materials have the BPH topology and have catalytic properties for carrying out various hydrocarbon conversion processes and separation properties for separating at least one component.
    Type: Grant
    Filed: November 21, 2018
    Date of Patent: October 1, 2019
    Assignee: UOP LLC
    Inventor: Gregory J. Lewis
  • Patent number: 10427145
    Abstract: A new family of crystalline microporous metalloalumino(gallo)phosphosilicates designated MeAPSO-82 has been synthesized. These metalloalumino(gallo)phosphosilicates are represented by the empirical formula of: Rp+rA+mM2+wExPSiyOz where A is an alkali metal such as potassium, R is an quaternary ammonium cation such as ethyltrimethylammonium, M is a divalent metal such as Zn and E is a trivalent framework element such as aluminum or gallium. This family of metalloalumino(gallo)phosphosilicate materials are stabilized by combinations of alkali and quaternary ammonium cations, enabling unique, high charge density compositions. The MeAPSO-82 family of materials have the CGS topology and have catalytic properties for carrying out various hydrocarbon conversion processes and separation properties for separating at least one component.
    Type: Grant
    Filed: November 21, 2018
    Date of Patent: October 1, 2019
    Assignee: UOP LLC
    Inventor: Gregory J. Lewis
  • Patent number: 9024101
    Abstract: A method for controlling 2-isomer content in linear alkylbenzene obtained by alkylating benzene with olefins and catalyst used in the method.
    Type: Grant
    Filed: October 14, 2013
    Date of Patent: May 5, 2015
    Assignee: UOP LLC
    Inventors: Mark G. Riley, Deng-Yang Jan, Stephen W. Sohn
  • Patent number: 8981170
    Abstract: In a process for producing a cycloalkylaromatic compound, an aromatic compound, hydrogen and at least one diluent are supplied to a hydroalkylation reaction zone, such that the weight ratio of the diluent to the aromatic compound supplied to the hydroalkylation reaction zone is at least 1:100. The aromatic compound, hydrogen and the at least one diluent are then contacted under hydroalkylation conditions with a hydroalkylation catalyst in the hydroalkylation reaction zone to produce an effluent comprising a cycloalkylaromatic compound.
    Type: Grant
    Filed: June 28, 2011
    Date of Patent: March 17, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Teng Xu, Wenyih F. Lai
  • 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
  • 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
  • Patent number: 8841500
    Abstract: Provided is a process for preparing alkyl aromatic compounds. The process comprises contacting an alkane under dehydrogenation conditions in the presence of a dehydrogenation catalyst, e.g., a pincer iridium catalyst, to form olefins, and then contacting the olefins generated with an aromatic compound under alkylation conditions. Both reactions are conducted in a single reactor, and occur simultaneously.
    Type: Grant
    Filed: September 12, 2012
    Date of Patent: September 23, 2014
    Assignees: Chevron U.S.A. Inc., Rutgers, The State University of New Jersey
    Inventors: Alan Stuart Goldman, Long Van Dinh, William L. Schinski
  • Patent number: 8716540
    Abstract: A new family of aluminosilicate zeolites designated UZM-44 has been synthesized. These zeolites are represented by the empirical formula. NanMmk+TtAl1-xExSiyOz where “n” is the mole ratio of Na to (Al+E), M represents a metal or metals from zinc, Group 1, Group 2, Group 3 and or the lanthanide series of the periodic table, “m” is the mole ratio of M to (Al+E), “k” is the average charge of the metal or metals M, T is the organic structure directing agent or agents, and E is a framework element such as gallium. UZM-44 may be used to catalyze an aromatic transformation process by contacting a feed comprising at least a first aromatic with UZM-44 at hydrocarbon conversion conditions to produce at least a second aromatic.
    Type: Grant
    Filed: November 8, 2013
    Date of Patent: May 6, 2014
    Assignee: UOP LLC
    Inventors: Christopher P. Nicholas, Antoine Negiz, Mark A. Miller
  • Publication number: 20140046108
    Abstract: A method for controlling 2-isomer content in linear alkylbenzene obtained by alkylating benzene with olefins and catalyst used in the method.
    Type: Application
    Filed: October 14, 2013
    Publication date: February 13, 2014
    Applicant: UOP LLC
    Inventors: Mark G. Riley, Deng-Yang Jan, Stephen W. Sohn
  • 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
  • Patent number: 8609920
    Abstract: A new family of aluminosilicate zeolites designated UZM-44 has been synthesized. These zeolites are represented by the empirical formula. NanMmk+TtAl1-xExSiyOz where “n” is the mole ratio of Na to (Al+E), M represents a metal or metals from zinc, Group 1, Group 2, Group 3 and or the lanthanide series of the periodic table, “m” is the mole ratio of M to (Al+E), “k” is the average charge of the metal or metals M, T is the organic structure directing agent or agents, and E is a framework element such as gallium. These zeolites are similar to IM-5 but are characterized by unique compositions and synthesis procedures and have catalytic properties for carrying out various hydrocarbon conversion processes and separation properties for carrying out various separations.
    Type: Grant
    Filed: March 11, 2013
    Date of Patent: December 17, 2013
    Assignee: UOP LLC
    Inventors: Mark A. Miller, Christopher P. Nicholas, Stephen T. Wilson
  • Publication number: 20130324760
    Abstract: A method of crystallizing a crystalline molecular sieve having a pore size in the range of from about 2 to about 19 ?, said method comprising the steps of (a) providing a mixture comprising at least one source of ions of tetravalent element (Y), at least one hydroxide source (OH?), and water, said mixture having a solid-content in the range of from about 15 wt. % to about 50 wt. %; and (b) treating said mixture to form the desired crystalline molecular sieve with stirring at crystallization conditions sufficient to obtain a weight hourly throughput from about 0.005 to about 1 hr?1, wherein said crystallization conditions comprise a temperature in the range of from about 200° C. to about 500° C. and a crystallization time less than 100 hr.
    Type: Application
    Filed: August 7, 2013
    Publication date: December 5, 2013
    Inventors: Ivy D. Johnson, Wenyih Frank Lai
  • Patent number: 8586496
    Abstract: A method is described for preparing a molecular sieve-containing catalyst for use in a catalytic process conducted in a stirred tank reactor. The method comprises providing a mixture comprising a molecular sieve crystal and forming the mixture into catalyst particles having an average cross-sectional dimension of between about 0.01 mm and about 3.0 mm. The mixture may include a binder and the catalyst particles are then calcined to remove water therefrom and, after calcination and prior to loading the catalyst particles into a reactor for conducting the catalytic process, the catalyst particles are coated with a paraffin inert to the conditions employed in the catalytic process.
    Type: Grant
    Filed: June 19, 2009
    Date of Patent: November 19, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Carolyn B. Duncan, Jon E. R. Stanat, Daria N. Lissy, Jane C. Cheng
  • Patent number: 8569557
    Abstract: A new family of crystalline microporous silicometallophosphates designated MAPSO-64 and modified forms thereof have been synthesized. These silicometallophosphates are represented by the empirical formula R+rMm2+EPxSiyOz where R is an organoammonium cation such as ETMA+ or DEDMA+, M is an alkaline earth or transition metal cation of valence 2+, and E is a trivalent framework element such as aluminum or gallium. The MAPSO-64 compositions are characterized by a BPH framework topology and have catalytic properties for carrying out various hydrocarbon conversion processes, and separation properties for separating at least one component.
    Type: Grant
    Filed: November 30, 2012
    Date of Patent: October 29, 2013
    Assignee: UOP LLC
    Inventors: Gregory J. Lewis, Lisa M. Knight, Paulina Jakubczak, Justin E. Stanczyk
  • Patent number: 8569558
    Abstract: A new family of crystalline microporous metallophosphates designated AlPO-67 has been synthesized. These metallophosphates are represented by the empirical formula R+rMm2+EPxSiyOz where R is an organoammonium cation such as the ETMA+ or DEDMA+, 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-67 compositions have the LEV topology and have catalytic properties for carrying out various hydrocarbon conversion processes, and separation properties for separating at least one component.
    Type: Grant
    Filed: November 30, 2012
    Date of Patent: October 29, 2013
    Assignee: UOP LLC
    Inventors: Gregory J. Lewis, Lisa M. Knight, Paulina Jakubczak, Justin E. Stanczyk
  • Patent number: 8569556
    Abstract: A method for controlling 2-isomer content in linear alkylbenzene obtained by alkylating benzene with olefins and catalyst used in the method.
    Type: Grant
    Filed: February 27, 2013
    Date of Patent: October 29, 2013
    Assignee: UOP LLC
    Inventors: Mark G. Riley, Deng-Yang Jan, Stephen W. Sohn
  • 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
  • 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: 8486877
    Abstract: An alkylated hydroxyaromatic compound is disclosed which is prepared by reacting at least one hydroxyaromatic compound with at least one branched olefinic propylene oligomer having from about 20 to about 80 carbon atoms in the presence of an acid catalyst, wherein the at least one branched olefinic propylene oligomer is substantially free of any vinylidene content. The alkylated hydroxyaromatic compound has been determined to be substantially free of endocrine disruptive chemicals when the effects were quantified on pubertal development and thyroid function in the intact juvenile female rat.
    Type: Grant
    Filed: November 18, 2009
    Date of Patent: July 16, 2013
    Assignee: Chevron Oronite Company LLC
    Inventors: Curtis Bay Campbell, James J. Harrison
  • Publication number: 20130150608
    Abstract: This invention is directed to an improvement in the process for the production of alkylaromatic compounds that results in lower levels of residual unreacted materials in the final product. This invention comprises: 1) alkylation of an aromatic compound with an alkylating agent and a catalyst to produce an effluent stream comprising an alkylaromatic compound and unreacted materials; 2) heating the effluent stream; 3) stripping the effluent stream in a stripping device in the presence of steam; 4) separating a stripping stream from the stripping device, the stripping stream rich in unreacted materials; and 5) separating a product stream from the stripping device, the product stream rich in alkylated aromatic compound.
    Type: Application
    Filed: December 13, 2011
    Publication date: June 13, 2013
    Inventors: Beth A. Winsett, James I. Arnett, II, Kenwyn M. Leger, Brady A. Compton
  • Publication number: 20130150607
    Abstract: This invention is directed to a new process for making an alkylaromatic compound. In an embodiment of this invention, the process is directed to selective synthesizing an alkylaromatic compound comprising a high amount of dialkylate product. In general, this process involves contacting at least one alkylatable aromatic compound with an alkylating agent and a catalyst under suitable reaction conditions such that the resulting reactor effluent prior to any stripping step may be characterized by a dialkylate product content of at least 44 wt % and a trialkylate and higher polyalkylate product content of no more than 20 wt %. The alkylaromatic compounds produced have excellent thermal and oxidative stabilities, good additive solvency, and improved seal compatibility while maintaining good VI and low temperature properties. They are useful as lubricant basestocks and lubricant additives.
    Type: Application
    Filed: December 7, 2011
    Publication date: June 13, 2013
    Inventor: Beth A. WINSETT
  • 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: 8455706
    Abstract: A method of producing a linear alkylbenzene that includes introducing an olefin into an aromatic stream to form a mixture; processing the mixture in a shear device at a shear rate greater than about 20,000 s?1 to form a dispersion; and reacting the dispersion in the presence of a catalyst in a reactor vessel to form a linear alkylbenzene product stream, wherein the reactor vessel is maintained at a bulk reaction temperature in the range of about 0° C. to about 60° C.
    Type: Grant
    Filed: August 1, 2012
    Date of Patent: June 4, 2013
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Patent number: 8431759
    Abstract: A process for increasing the production of monoalkylbenzenes is presented. The process includes utilizing a transalkylation process to convert dialkylbenzenes to monoalkylbenzenes. The transalkylation process recycles a portion of the effluent stream from the transalkylation reactor back to the feed of the transalkylation reactor. The recycled dialkylbenzenes and a portion of the recycled benzene are converted to monoalkylbenzenes.
    Type: Grant
    Filed: November 30, 2012
    Date of Patent: April 30, 2013
    Assignee: UOP LLC
    Inventors: Stephen W. Sohn, Mark G. Riley
  • Patent number: 8389786
    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: December 10, 2010
    Date of Patent: March 5, 2013
    Assignee: UOP LLC
    Inventors: Mark G. Riley, Stephen W. Sohn, Deng-Yang Jan
  • Patent number: 8389785
    Abstract: A method for controlling 2-isomer content in linear alkylbenzene obtained by alkylating benzene with olefins and catalyst used in the method.
    Type: Grant
    Filed: September 14, 2010
    Date of Patent: March 5, 2013
    Assignee: UOP LLC
    Inventors: Mark G. Riley, Deng-Yang Jan, Stephen W. Sohn
  • Patent number: 8389787
    Abstract: A process is presented for the management and control of the 2-phenyl content in a benzene alkylation process. The process includes the use of multiple reactor beds, with benzene flowing through the reactor beds in a sequential manner. The olefin stream is split to two or more portions, and a separate portion is passed to the first reactor bed and second reactor bed. Control of the ratio of the olefin flow splits controls the 2-phenyl content.
    Type: Grant
    Filed: March 21, 2012
    Date of Patent: March 5, 2013
    Assignee: UOP LLC
    Inventors: Debarshi Majumder, Stephen W. Sohn
  • Patent number: 8329966
    Abstract: Synthetic base oil composition comprising dialkyl aromatic compound with alkyl side chain carbon number from C10 to C28, or preferably C11 to C24, or even more preferably, C12 to C18, wherein the branching characteristics of the alkyl side chain has a total methyl number (TMN) determined by C13 NMR spectroscopy to be from more than 2.1 to less than 3.5, or preferably from 2.15 to 3.25, or even more preferably from 2.2 to 3.0, or a branching index (BI) from more than 0.1 to less than 1.5, or more preferably, 0.15 to 1.25, or even more preferably, 0.2 to 1.0. The synthetic base oil composition has a combination of high viscometric index, low volatility, superior low temperature properties, and improved thermal/oxidation stability, and is particularly suitable to be used as a premium synthetic base stock, second base oil component, or additive for lubricant and additive package applications.
    Type: Grant
    Filed: October 10, 2007
    Date of Patent: December 11, 2012
    Assignee: Formosan Union Chemical Corp.
    Inventors: Chi-Hsing Tsai, Chien-Hsun Tsai
  • Patent number: 8278494
    Abstract: Methods and systems for the production of linear alkylbenzenes are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and mixing of one or more olefins (e.g. propylene) with an aromatic. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time with existing catalysts.
    Type: Grant
    Filed: June 23, 2008
    Date of Patent: October 2, 2012
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Patent number: 8237001
    Abstract: The present invention refers to a procedure for obtaining a linear monoalkylaromatic compound, with adjustable 2-phenyl isomer content and an extremely low sulphonation color, in which a catalytic system is used based on highly stable and active solid catalysts and with a high selectivity for linear monoalkylaromatic compounds.
    Type: Grant
    Filed: December 4, 2007
    Date of Patent: August 7, 2012
    Assignee: Cepsa Quimica, S.A.
    Inventors: José Luis Berna Tejero, José Luis Goncalvez De Almeida
  • Patent number: 8183420
    Abstract: An alkylaromatic hydrocarbon composition prepared by the process which comprises oligomerizing an olefin selected from the group consisting of propylene, n-butene and mixtures thereof over an oligomerization catalyst, to form a oligomerization product comprising at least 95% by weight of mono-olefin oligomers of the empirical formula: CnH2n wherein n is greater than or equal to 10, the mono-olefin oligomers comprise at least 20% by weight of olefins having at least 12 carbon atoms, and the olefins having at least 12 carbon atoms having an average of from 0.8 to 2.0 C1-C3 alkyl branches per carbon chain. Sulfonation of the alkylaromatic hydrocarbon product produces an alkylaryl sulfonate mixture that exhibits advantageous properties, such as biodegradability and hard and cold water performance.
    Type: Grant
    Filed: October 8, 2009
    Date of Patent: May 22, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Carolyn B. Duncan, David Wayne Turner, Jane C. Cheng, Charles M. Yarbrough, Raphael Frans Caers, Ramzi Y. Saleh, James L. Propp
  • Patent number: 8158839
    Abstract: A process is presented for the production of linear alkylbenzenes. The process includes contacting an aromatic compound with an olefin in the presence of a selective zeolite catalyst. The catalyst includes two zeolites combined to improve the linearity, and to produce detergent grade LAB. The two zeolites are selected to limit skeletal isomerization while producing a desired 2-phenyl content for the LAB.
    Type: Grant
    Filed: May 5, 2011
    Date of Patent: April 17, 2012
    Assignee: UOP LLC
    Inventors: Mark G. Riley, Deng-Yang Jan, Stephen W. Sohn, Jaime G. Moscoso
  • Patent number: 8124035
    Abstract: Continuous processes for monoalkylating aromatic compound with an aliphatic feedstock comprising aliphatic olefin of 8 to 18 carbon atoms per molecule are effected using at least 3 reaction zones in series, each containing solid alkylation catalyst with effluent cooling between reaction zones, each of which reaction zones is supplied a portion of the fresh aliphatic feedstock, such that the Reaction Zone Delta T in each reaction zone is less than about 15° C. The overall aromatic compound to olefin molar ratio is less than about 20:1. The alkylation product has desirable linearity and low amounts of dimers, dealkylated compounds and diaryl compounds even though a low aromatic compound to olefin molar ratio is used.
    Type: Grant
    Filed: February 5, 2010
    Date of Patent: February 28, 2012
    Assignee: UOP LLC
    Inventor: Mark G. Riley
  • Patent number: 8071829
    Abstract: A process is disclosed for the alkylation of aromatics by charging a hydrocarbon feed containing aromatic hydrocarbons and olefinic hydrocarbons to a distillation column for separation into at least one fraction; removing an aromatics/olefin stream containing at least a portion of the aromatic hydrocarbons and at least a portion of the olefinic hydrocarbons; charging the aromatics/olefin stream to an alkylation reactor, operated at a temperature in the range of from about 80° C. to about 220° C., for alkylation of at least a portion of the aromatic hydrocarbons with the olefinic hydrocarbons; recycling at least a portion of the resulting reactor effluent to the distillation column; and removing a product stream containing alkylated aromatics from the distillation column.
    Type: Grant
    Filed: February 20, 2009
    Date of Patent: December 6, 2011
    Assignee: ConocoPhillips Company
    Inventors: Bradley M. Taylor, Barbara A. Todd
  • Patent number: 8058494
    Abstract: A process for the production of phenylalkanes comprising at least two catalytic alkylation reactors placed in parallel among which are present in reaction zones that each contain at least one acidic solid catalyst, whereby n is greater than or equal to 2, is described. One of the reactors carries out the alkylation of at least one aromatic compound by at least one olefin that has 9 to 16 atoms. An olefin fraction is introduced at the inlet of each of the reaction zones of the reactor that operates in alkylation mode. While one of the reactors carries out the alkylation, the other reactor carries out the reactivation of each catalyst, partially deactivated, that it contains. The functions of each reactor are switched regularly so as to limit the deactivation of catalysts in each of the reactors. The phenylalkanes that are obtained by the process according to the invention are particularly suitable for the production of detergents.
    Type: Grant
    Filed: October 4, 2005
    Date of Patent: November 15, 2011
    Assignee: IFP Energies Nouvelles
    Inventors: Emmanuelle Guillon, Eric Sanchez
  • Publication number: 20110245563
    Abstract: A new family of crystalline aluminosilicate zeolites has been synthesized. These zeolites are represented by the empirical formula. Mmn+Rr+Al(1-x)ExSiyOz where M represents a combination of potassium and sodium exchangeable cations, R is a singly charged organoammonium cation such as the propyltrimethylammonium cation and E is a framework element such as gallium. These zeolites are similar to MWW but are characterized by unique x-ray diffraction patterns and compositions and have catalytic properties for carrying out alkylation processes.
    Type: Application
    Filed: June 9, 2011
    Publication date: October 6, 2011
    Applicant: UOP LLC
    Inventors: Deng-Yang Jan, Jaime G. Moscoso
  • Publication number: 20110237826
    Abstract: This invention relates to a crystalline molecular sieve having, in its as-synthesized form, an X-ray diffraction pattern including d-spacing maxima at 13.18±0.25 and 12.33±0.23 Angstroms, wherein the peak intensity of the d-spacing maximum at 13.18±0.25 Angstroms is at least as great as 90% of the peak intensity of the d-spacing maximum at 12.33±0.23 Angstroms. This invention also relates to a method of making thereof.
    Type: Application
    Filed: April 28, 2011
    Publication date: September 29, 2011
    Inventors: Wieslaw J. Roth, Thomas Yorke, Michael C. Kerby, Simon C. Weston
  • Publication number: 20110207981
    Abstract: A process is presented for the production of linear alkylbenzenes. The process includes contacting an aromatic compound with an olefin in the presence of a selective zeolite catalyst. The catalyst includes two zeolites combined to improve the linearity, and to produce detergent grade LAB. The two zeolites are selected to limit skeletal isomerization while producing a desired 2-phenyl content for the LAB.
    Type: Application
    Filed: May 5, 2011
    Publication date: August 25, 2011
    Applicant: UOP LLC
    Inventors: Mark G. Riley, Deng-Yang Jan, Stephen W. Sohn, Jaime G. Moscoso
  • Patent number: 7973206
    Abstract: A process is presented for the production of linear alkylbenzenes. The process includes contacting an aromatic compound with an olefin in the presence of a selective zeolite catalyst. The catalyst includes two zeolites combined to improve the linearity, and to produce detergent grade LAB. The two zeolites are selected to limit skeletal isomerization while producing a desired 2-phenyl content for the LAB.
    Type: Grant
    Filed: December 16, 2009
    Date of Patent: July 5, 2011
    Assignee: UOP LLC
    Inventors: Mark G. Riley, Deng-Yang Jan, Stephen W. Sohn, Jaime G. Moscoso
  • Publication number: 20110144402
    Abstract: A process is presented for the production of linear alkylbenzenes. The process includes contacting an aromatic compound with an olefin in the presence of a selective zeolite catalyst. The catalyst includes two zeolites combined to improve the linearity, and to produce detergent grade LAB. The two zeolites are selected to limit skeletal isomerization while producing a desired 2-phenyl content for the LAB.
    Type: Application
    Filed: December 16, 2009
    Publication date: June 16, 2011
    Applicant: UOP LLC
    Inventors: Mark G. Riley, Deng-Yang Jan, Stephen W. Sohn, Jaime G. Moscoso
  • Publication number: 20110077442
    Abstract: A aromatic alkylation catalyst, processes for producing the catalyst, and aromatic alkylation processes employing the catalysts are disclosed. The catalyst comprises a UZM-8 zeolite and nitrogen, and the catalyst has a nitrogen to zeolite aluminum molar ratio of at least about 0.015. In an exemplary alkylation process, the catalyst provides improved product yield.
    Type: Application
    Filed: September 10, 2010
    Publication date: March 31, 2011
    Applicant: UOP LLC
    Inventors: Deng-Yang Jan, James A. Johnson, Robert J. Schmidt, Mathias P. Koljack
  • Patent number: 7910759
    Abstract: Alkyl-capped alkoxylated ester compounds of the formula wherein R1 is ethyl or butyl, R2 is linear or branched C16 to C18 hydrocarbon and x is greater than 3 to an n of 10.5 which are the reaction products of ethoxylating compounds of the formula R1O(CH2CH2O)nH that are free of ethylene glycol alkyl ether and diethyleneglycol alkyl ether. The ethoxylated reaction products are surfactants that exhibit suds controlling properties with various anionic surfactants.
    Type: Grant
    Filed: March 28, 2006
    Date of Patent: March 22, 2011
    Assignee: The Procter & Gamble Company
    Inventors: Lon Montgomery Gray, Jeffrey John Scheibel, Phillip Kyle Vinson, Christopher James Binski
  • Patent number: 7812205
    Abstract: A process is disclosed wherein a layered catalyst is used for the alkylation of benzene with a substantially linear olefin. The layered catalyst allows for shifting the operating conditions to increase the alkylation of benzene, while reducing the amount of isomerization of the alkyl group. This is important for increasing the quality of the alkylbenzene by increasing the linearity of the alkylbenzene.
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: October 12, 2010
    Assignee: UOP LLC
    Inventors: Deng-Yang Jan, Mark G. Riley
  • Patent number: 7795483
    Abstract: The present invention is a process for producing phenyl-alkanes by paraffin adsorptive separation followed by paraffin dehydrogenation and then by alkylation of a phenyl compound by a lightly branched olefin. The adsorptive separation step employs a silicalite adsorbent and, as the desorbent, a C5-C8 linear paraffin, a C5-C8 cycloparaffin, a branched paraffin such as isooctane, or mixtures thereof. The effluent of the alkylation zone comprises paraffins that are recycled to the adsorptive separation step or to the dehydrogenation step. This invention is also a process that that sulfonates phenyl-alkanes having lightly branched aliphatic alkyl groups that to produce modified alkylbenzene sulfonates. In addition, this invention is the compositions produced by these processes, which can be used as detergents having improved cleaning effectiveness in hard and/or cold water while also having biodegradability comparable to that of linear alkylbenzene sulfonates, as lubricants, and as lubricant additives.
    Type: Grant
    Filed: September 9, 2003
    Date of Patent: September 14, 2010
    Assignee: UOP LLC
    Inventors: Santi Kulprathipanja, Richard E. Marinangeli, Stephen W. Sohn, Thomas R. Fritsch, R. Joe Lawson
  • Patent number: 7732651
    Abstract: A process for alkylating an aromatic compound containing no hydroxyl groups comprising reacting at least one non-hydroxyl containing aromatic compound with at least one olefinic oligomer in the presence of an acidic ionic liquid catalyst, wherein the olefinic oligomer has a carbon range of from about C12 to about C70 and is synthesized by oligomerizing at least one monoolefin monomer in the presence of an acidic ionic liquid catalyst.
    Type: Grant
    Filed: June 1, 2006
    Date of Patent: June 8, 2010
    Assignee: Chevron Oronite Company, LLC
    Inventors: Michael Driver, Curt B. Campbell, Thomas V. Harris
  • Patent number: 7692054
    Abstract: Continuous processes for monoalkylating aromatic compound with an aliphatic feedstock comprising aliphatic olefin of 8 to 18 carbon atoms per molecule are effected using at least 3 reaction zones in series, each containing solid alkylation catalyst with effluent cooling between reaction zones, each of which reaction zones is supplied a portion of the fresh aliphatic feedstock, such that the Reaction Zone Delta T in each reaction zone is less than about 15° C. The overall aromatic compound to olefin molar ratio is less than about 20:1. The alkylation product has desirable linearity and low amounts of dimers, dealkylated compounds and diaryl compounds even though a low aromatic compound to olefin molar ratio is used.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: April 6, 2010
    Assignee: UOP LLC
    Inventor: Mark G. Riley
  • Patent number: 7655824
    Abstract: The alkylation of aromatic compound with acyclic mono-olefin is effected at low aromatic compound to mono-olefin ratios with reduced co-production of heavies. In the processes a small crystal, acidic FAU molecular sieve is used as a catalyst under alkylation conditions. This invention also relates to catalysts containing small crystal, acidic FAU molecular sieve and at least one other acidic catalytic component.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: February 2, 2010
    Assignee: UOP LLC
    Inventors: Mark G. Riley, Deng-Yang Jan, Stephen W. Sohn
  • Patent number: 7638666
    Abstract: Dialkylbenzenes are transalkylated in the presence of benzene and solid catalyst. The transalkylation product is subjected to distillation to provide a lower-boiling, benzene-containing fraction which is fed to a transalkylation reactor as at least a portion of the benzene. Thus, high benzene to dialkylbenzene molar ratios can be economically maintained in order to enhance catalyst stability.
    Type: Grant
    Filed: September 24, 2008
    Date of Patent: December 29, 2009
    Assignee: UOP LLC
    Inventors: Stephen W. Sohn, Mark G. Riley
  • Patent number: 7601861
    Abstract: In a process for preparing alkylaryl compounds by reacting a C10-14-monoolefin mixture with an aromatic hydrocarbon in the presence of an alkylation catalyst to form alkyl aromatic compounds and if appropriate subsequently sulfonating and neutralizing the resulting alkylaryl compounds, in the C10-14-monoolefins, on average, more than 0% and up to 100% of methyl branches are present in the longest carbon chain and fewer than 50% of the methyl branches are in the 2-, 3- and 4-position, calculated starting from the chain ends of the longest carbon chain.
    Type: Grant
    Filed: October 29, 2004
    Date of Patent: October 13, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Nils Bottke, Regina Benfer, Marco Bosch, Thomas Narbeshuber, Ulrich Steinbrenner, Juergen Stephan