Polymerization Of Olefins Only Patents (Class 585/255)
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Patent number: 11891517Abstract: Wax compositions may be obtained by providing an olefinic feed comprising a first linear alpha olefin having m carbon atoms and a second linear alpha olefin having n carbon atoms, wherein m and n are independently selected integers each ranging from about 12 to about 100, and the olefinic feed optionally comprises one or more internal olefins and/or one or more branched olefins; contacting the olefinic feed with a metal carbene catalyst in a reactor; forming ethylene and a hydrocarbon substance comprising a linear olefin dimer comprising two carbon atoms less than a sum of m and n; removing the ethylene from the reactor while forming the linear olefin dimer; and isolating a wax composition comprising the linear olefin dimer, a hydrogenated reaction product thereof, or any combination thereof.Type: GrantFiled: March 2, 2021Date of Patent: February 6, 2024Assignee: ExxonMobil Chemical Patents Inc.Inventors: Anatoly I. Kramer, Alexander V. Zabula, Elizabeth A. Turner, Raf de Meester, Helge Jaensch, Jeffrey C. Bunquin, Javier Guzman, Emiel de Smit, John S. Coleman, Madelyn Bekker, Roxana Perez Velez
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Patent number: 11352571Abstract: Systems and methods are provided for conversion of oxygenate feeds to lubricant and/or distillate boiling range compounds with desirable properties by first selectively converting oxygenates to light olefins and then converting the light olefins to distillate and lubricant boiling range compounds with beneficial properties. The distillate boiling range products can have an unexpectedly high cetane, while the lubricant boiling range products can have an unexpectedly high viscosity index. The ability to form the distillate boiling range products and lubricant boiling range products is facilitated by using a Ni-enhanced oligomerization catalyst.Type: GrantFiled: July 29, 2019Date of Patent: June 7, 2022Assignee: ExxonMobil Technology and Engineering CompanyInventors: Mark A. Deimund, Brandon J. O'Neill, Ajit B. Dandekar
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Patent number: 11332690Abstract: A process for the preparation of saturated hydrocarbon base oils is provided, comprising oligomerization of a feed mixture that has an average carbon number in the range of 14 to 18 to produce an oligomer product comprising dimers, trimers, and higher oligomers, where the dimer has a branching proximity (BP) of 20 or greater, isomerization of at least the dimer portion, and hydrogenation of the isomerized product. The dimer portion is separated from the oligomer product, and a saturated hydrocarbon base oil is obtained comprising greater than 90% dimers having an average carbon number in the range of from 29 to 36, and the dimer portion having a weight average molecular weight in the range of 422 to 510, where the dimers have an average Branching Index (BI) in a range of 22 to 26 and an average paraffin branching proximity (BP) in a range of from 18 to 26.Type: GrantFiled: July 13, 2018Date of Patent: May 17, 2022Assignee: NOVVI LLCInventors: Eduardo Baralt, Jason Wells, Jason Charles Rosalli, Wui Sum Willbe Ho, Liwenny Ho, Benton Thomas
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Patent number: 11180430Abstract: The disclosure relates to olefin oligomerization processes and related zeolites and structure directing agents. The olefin oligomerization processes can exhibit relatively high conversions. The zeolites can exhibit comparatively high stabilities. The zeolites can have relatively high ratios of external surface area to total surface area. An exemplary zeolite is a beta zeolite having a relatively high ratio of external surface area to total surface area. The disclosure also relates to structure directing agents, and methods of using the structure direction agents to prepare the zeolites.Type: GrantFiled: April 30, 2018Date of Patent: November 23, 2021Assignee: ExxonMobil Chemical Patents Inc.Inventors: Alejandra R. Rivas Cardona, Allen W. Burton, Sina Sartipi, Andrew D. Wiersum, Lara A. Truter, Marianne F. Smits
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Patent number: 11021669Abstract: The invention is the use, in an electric vehicle, of a fluid having a boiling point in the range of from 200° C. to 400° C. and a boiling range below 80° C., said fluid comprising more than 95% by weight isoparaffins and less than 3% by weight of naphthens, a biocarbon content of at least 95% by weight, containing less than 100 ppm by weight aromatics.Type: GrantFiled: October 26, 2017Date of Patent: June 1, 2021Assignee: TOTAL MARKETING SERVICESInventor: Philippe China
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Patent number: 10464864Abstract: In a process for upgrading an ethane-containing C5- paraffin stream, the paraffin stream is contacted with an oxygen containing gas in the presence of a selective oxidation catalyst under conditions to selectively oxidize at least part of the ethane in the paraffin stream and produce a first product stream comprising ethylene. At least part of the first product stream is then with an oligomerization catalyst under conditions to oligomerize at least part of the ethylene and produce a second product stream comprising gasoline and/or distillate boiling range hydrocarbons. Gasoline and/or distillate boiling range hydrocarbons are then recovered from the second product stream and at least a part of any residual C5- paraffin stream is recycled to the selective oxidation step.Type: GrantFiled: December 7, 2017Date of Patent: November 5, 2019Assignee: EXXONMOBIL RESEARCH AND ENGINEERING COMPANYInventors: Guang Cao, Jihad Dakka
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Patent number: 10322980Abstract: Disclosed is a method of manufacturing high-quality lube base oil, by converting a low-value linear alpha-olefin having a C18 or more hydrocarbon chain into a linear internal-olefin having a controlled double bond position distribution and then oligomerizing the linear internal-olefin.Type: GrantFiled: April 22, 2015Date of Patent: June 18, 2019Assignees: SK Innovation Co., Ltd., SK Lubricants Co., Ltd.Inventors: Hee Jung Jeon, Jin Hee Ok, Tae Jin Kim, Wan Seop Kwon
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Patent number: 10173195Abstract: Processes relating to thermal activation (or cracking) of ethane to an intermediate, low purity raw ethylene stream in a first stage. This stream is then mixed with a stream of biomass-derived ethanol that may contain four volume percent or more of water. The resulting mixture is reacted over a suitable catalyst at temperatures and pressures suitable to produce gasoline-range and diesel-range blend stock.Type: GrantFiled: December 16, 2014Date of Patent: January 8, 2019Assignee: Phillips 66 CompanyInventors: Jianhua Yao, Dhananjay Ghonasgi, Tushar Choudhary, Warren Ewert
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Patent number: 10087380Abstract: A process for converting ethane to liquid fuels may involve directing an ethane stream into an ethane cracking unit to produce an intermediate hydrocarbon stream and a raw ethylene stream; fractionating the intermediate hydrocarbon stream into a gasoline fraction and a diesel fraction; introducing the raw ethylene stream into an oligomerization unit; contacting the raw ethylene stream with an oligomerization catalyst to produce a liquid hydrocarbon stream and an off-gas stream; recycling an off-gas recycle stream from an off-gas stream of the oligomerization unit separation unit to an inlet of the oligomerization reactor; introducing at least part of the off-gas stream into a hydrogenation reactor to remove unconverted olefins; separating a hydrogen component and a plurality of light paraffin components in a post hydrogenation reactor separation unit using a PSA technology or membrane technology; and recycling the light paraffins stream into the ethane cracking unit.Type: GrantFiled: December 16, 2014Date of Patent: October 2, 2018Assignee: Phillips 66 CompanyInventors: Jianhu Yao, Dhananjay Ghonasgi, Tushar Choudhary, Warren Ewert
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Patent number: 9938207Abstract: A process for converting paraffins, especially light paraffins, e.g. C3-C8 paraffins, to higher boiling range paraffinic liquid hydrocarbons comprises endothermically dehydrogenating the light paraffin combined with a thermally coupled, exothermic reaction such as olefin oligomerization to supply heat for the endothermic conversion.Type: GrantFiled: February 3, 2016Date of Patent: April 10, 2018Assignee: EXXONMOBIL RESEARCH AND ENGINEERING COMPANYInventors: Kun Wang, Robert T. Carr, Elise Marucchi-Soos
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Patent number: 9731270Abstract: Converting ethane may include directing a gaseous stream from a gas well into a fractionator for fractionating and producing a post-fractionator ethane stream, which is directed into a thermal activation unit for heating and raising the temperature of the post-fractionator ethane stream thereby creating an activated ethane stream, which is directed into a quench tower thereby creating a quenched stream, which may be converted in a catalytic conversion unit to a mixed product stream containing hydrogen and C1-C15 hydrocarbons; directing the mixed product stream into a first separation unit forming a stream of C4+ hydrocarbon product and a stream of C1-C3 hydrocarbons; directing the stream of C1-C3 hydrocarbons into a catalytic hydrogenation reactor thereby imparting hydrogen into a post-hydrogenation reactor stream, which is directed directly into a second separation unit thereby creating a light hydrocarbons recycle stream, which may be recycled into the thermal activation unit, and a hydrogen and methane strType: GrantFiled: December 16, 2014Date of Patent: August 15, 2017Assignee: PHILLIPS 66 COMPANYInventors: Jianhua Yao, Dhananjay Ghonasgi, Tushar Choudhary, Warren Ewert
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Patent number: 9371258Abstract: A method for producing high density fuels from isoprene which can be produced via biosynthetic routes using biomass sugars as feedstock. This allows for the production of isoprene and isoprene-derived fuels from abundant waste materials with the potential to significantly reduce DoD carbon emissions. Embodiments of the invention describe a method for conversion of isoprene to full performance jet and diesel fuels. Isoprene can be selectively oligomerized to generate a distribution of branched chain hydrocarbons. Combination of an oligomerization catalyst with a metathesis catalyst allows for the synthesis of high density cyclic fuels with performance advantages (increased density and volumetric net heat of combustion) over conventional petroleum-based fuels.Type: GrantFiled: June 25, 2014Date of Patent: June 21, 2016Assignee: The United States of America as Represented by the Secretary of the NavyInventor: Benjamin G. Harvey
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Patent number: 9267091Abstract: We provide a process for making a base oil, comprising: feeding an olefin feed comprising a propylene to an oligomerization zone comprising an acidic ionic liquid catalyst prepared from an organic-based cation; and tuning an oligomerizing step in the oligomerization zone by mixing a C6+olefin with the propylene in the oligomerization zone to increase a viscosity index of the base oil. We also provide a process for making a base oil, comprising tuning an oligomerizing step by mixing a C6+olefin with a propylene in an oligomerization zone comprising an acidic ionic liquid catalyst prepared from an organic-based cation to increase a viscosity index of the base oil produced in the oligomerization zone; wherein the base oil has selected properties.Type: GrantFiled: March 16, 2012Date of Patent: February 23, 2016Assignee: Chevron U.S.A. Inc.Inventors: Saleh Ali Elomari, Stephen Joseph Miller
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Publication number: 20150073185Abstract: Provided is a Group 9 novel metal catalyst complex further comprising a ketone-containing cocatalyst. The metal catalyst complex is useful in generating olefins from alkanes with great efficiency. In one embodiment, provided is an iridium catalyst complex useful in the dehydrogenation of alkanes comprising a ketone-containing cocatalyst and iridium complexed with a tridentate ligand. Also provided is a novel dehydrogenation method which utilizes the catalyst composition. In other embodiments, a novel process for preparing oligomers from alkanes utilizing the catalyst composition is provided.Type: ApplicationFiled: September 10, 2014Publication date: March 12, 2015Applicants: Rutgers, The State University of New Jersey, Chevron U.S.A. Inc.Inventors: Alan Stuart Goldman, Robert Timothy Stibrany, Robert J. Saxton, Oleg MIRONOV
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Publication number: 20150045599Abstract: A method for producing jet-range hydrocarbons includes passing a stream comprising renewable C4 olefins to an oligomerization reactor containing a zeolite catalyst to produce an oligomerized effluent, separating the oligomerized effluent to produce a jet range hydrocarbon stream and a recycle stream comprising C8 olefins, and passing at least a portion of the recycle stream to the oligomerization reactor. A first at least about 10% of the jet-range hydrocarbon stream hydrocarbons boil between n-octane and n-undecane and wherein a second at least about 10% of the jet-range hydrocarbon stream hydrocarbons boil between n-dodecane and n-pentadecane.Type: ApplicationFiled: November 6, 2013Publication date: February 12, 2015Applicant: UOP LLCInventors: Stanley Joseph Frey, Geoffrey William Fichtl, Paul Barger, Scott M. Roney, Steven Lee Krupa, Christopher P. Nicholas
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Publication number: 20150011812Abstract: In a process for producing cyclohexylbenzene, hydrogen and benzene are introduced to a first hydroalkylation reaction zone which contains a hydroalkylation catalyst and which is operated under at least partly liquid phase conditions sufficient to effect hydroalkylation of benzene to produce a mixed liquid/vapor phase effluent comprising cyclohexylbenzene and unreacted benzene, wherein at least a portion of the unreacted benzene is in the vapor phase. At least a portion of the effluent is cooled to condense a liquid phase stream containing at least some of the cyclohexylbenzene in the effluent portion and leave a residual stream containing at least some of the unreacted benzene and cyclohexylbenzene. At least a portion of the liquid stream is recycled to the first hydroalkylation reaction zone or to contact the mixed phase effluent exiting the first hydroalkylation reaction zone. Other methods of cooling the reaction effluent are disclosed.Type: ApplicationFiled: January 28, 2013Publication date: January 8, 2015Inventors: Christopher L. Becker, Hari Nair, James R. Lattner, Keith H. Kuechler
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Publication number: 20140378720Abstract: A process to produce polyalpha-olefins includes contacting a feed stream of at least one alpha-olefin monomer having 4 to 25 carbon atoms with a metallocene catalyst compound and an activator, and optionally an alkyl-aluminum compound, under polymerizations conditions in a reactor. The alpha-olefin monomer is present at 10% volume or more in the reactor and the feed stream includes less than 600 ppm of heteroatom containing compounds. The process further includes obtaining a polyalpha-olefin with at least 50 mole % C5 to C24 alpha-olefin monomer and kinematic viscosity at 100° C. of 5000 cSt or less.Type: ApplicationFiled: May 6, 2014Publication date: December 25, 2014Inventors: Margaret M. Wu, Norman Yang, Lisa S. Baugh, Jo Ann M. Canich, Steven P. Rucker, John F. Walzer, JR., Gordon H. Lee, Frederick Y. Lo, Andrew Jackson, Mark P. Hagemeister, Shakeel Tirmizi, Peijun Jiang, Chia S. Chee
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Publication number: 20140378697Abstract: This invention relates to process for producing biphenyl esters, the process comprising: (a) contacting a feed comprising toluene, xylene or mixtures thereof with hydrogen in the presence of a hydroalkylation catalyst to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluene, wherein the hydroalkylation catalyst comprises: 1) binder present at 40 wt % or less (based upon weight of final catalyst composition), 2) a hydrogenation component present at 0.2 wt % or less (based upon weight of final catalyst composition), and 3) an acidic component comprising a molecular sieve having a twelve membered (or larger) ring pore opening, channel or pocket and a largest pore dimension of 6.Type: ApplicationFiled: June 25, 2014Publication date: December 25, 2014Inventors: Emiel de Smit, Neeraj Sangar, Michael Salciccioli, Jihad M. Dakka, Lorenzo C. DeCaul, Terry E. Helton, Scott J. Weigel
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Publication number: 20140275664Abstract: Disclosed are processes for forming an oligomer product by contacting a feedstock olefin containing trisubstituted olefins with a solid acid catalyst. The oligomer product can be formed at an oligomerization temperature in a range from ?20° C. to 40° C. Polyalphaolefins produced from the oligomer product can have reduced viscosities at low temperatures.Type: ApplicationFiled: March 13, 2013Publication date: September 18, 2014Applicant: Chevron Phillips Chemical Company LPInventors: Hu Yang, Kenneth D. Hope, Jeff C. Gee
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Publication number: 20140249340Abstract: The invention relates to a process for the production of middle-distillate hydrocarbon-containing bases from a feedstock comprising butanol and pentanol, with said process comprising at least: a) Isomerizing dehydration of said feedstock; b) Separation of the water that is present in said olefinic effluent; c) Purification of the organic liquid effluent coming from b); d) Selective oligomerization of a feedstock that comprises at least a portion of the purified organic effluent coming from c), to produce a first oligomerization effluent; e) Oligomerization of said first oligomerization effluent in such a way as to produce a second oligomerization effluent; f) Fractionation of said second oligomerization effluent into at least three products, a light product, an intermediate product and a distillate product; g) Oligomerization of at least a portion of said intermediate product; h) Hydrogenation of at least a portion of said distillate product.Type: ApplicationFiled: March 4, 2014Publication date: September 4, 2014Applicant: IFP ENERGIES NOUVELLESInventors: Vivien Tom, Vincent Coupard, Francois Hugues, Raphael Huyghe
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Publication number: 20140221258Abstract: Provided herein are isoparaffins derived from hydrocarbon terpenes such as myrcene, ocimene and farnesene, and methods for making the same. In certain variations, the isoparaffins have utility as lubricant base stocks.Type: ApplicationFiled: February 13, 2012Publication date: August 7, 2014Applicant: AMYRIS, INC.Inventors: Nicholas Ohler, Karl Fisher, Shakeel Tirmizi
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Patent number: 8785702Abstract: A process for making diesel and turbine fuels including, providing an effective amount of branched olefins, adding active heterogeneous acid catalyst(s) to said branched olefins to produce a solvent-free mixture, heating said solvent-free mixture greater than about 100° C. for a desired amount of time depending on various conditions, to produce C16 dimers/catalyst mixture, removing said catalysts from said dimers/catalyst mixture, and adding hydrogenation catalyst(s) to said dimers under hydrogen atmosphere to produce a mixture of stable fuels.Type: GrantFiled: April 29, 2010Date of Patent: July 22, 2014Assignee: The United States of America as Represented by the Secretary of the NavyInventors: Benjamin G. Harvey, Roxanne L. Quintana, Michael E. Wright
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Publication number: 20140163267Abstract: The present invention is directed to renewable compositions derived from fermentation of biomass, and integrated methods of preparing such compositions.Type: ApplicationFiled: September 27, 2013Publication date: June 12, 2014Applicant: GEVO, INC.Inventors: Patrick R. GRUBER, Matthew W. Peters, Josefa M. Griffith, Yassin Al Obaidi, Leo E. Manzer, Joshua D. Taylor, David E. Henton
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Publication number: 20140148623Abstract: The invention provides for methods, compositions and systems using bioisoprene derived from renewable carbon for production of a variety of hydrocarbon fuels and fuel additives.Type: ApplicationFiled: April 26, 2013Publication date: May 29, 2014Applicant: DANISCO US INC.Inventor: Danisco US Inc.
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Publication number: 20140135541Abstract: Oligomerizing C4 and C5 olefins over a SPA catalyst provides an oligomerate product stream comprising C6+ olefins that meets a gasoline T-90 specification of 380° F. The oligomerate product stream can be taken to the gasoline pool without further upgrading.Type: ApplicationFiled: November 8, 2013Publication date: May 15, 2014Applicant: UOP LLCInventors: Christopher P. Nicholas, Christian D. Freet, Steven L. Krupa, Kurt M. Vanden Bussche, Todd M. Kruse
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Patent number: 8697925Abstract: A process for making diesel and turbine fuels including, providing an effective amount of branched olefins, adding active heterogeneous acid catalyst(s) to said branched olefins to produce a solvent-free mixture, heating said solvent-free mixture greater than about 100° C. for a desired amount of time depending on various conditions, to produce C16 dimers/catalyst mixture, removing said catalysts from said dimers/catalyst mixture, and adding hydrogenation catalyst(s) to said dimers under hydrogen atmosphere to produce a mixture of stable fuels.Type: GrantFiled: April 29, 2010Date of Patent: April 15, 2014Assignee: The United States of America as Represented by the Secretary of the NavyInventors: Benjamin G. Harvey, Roxanne L. Quintana, Michael E. Wright
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Publication number: 20140088319Abstract: The present invention discloses a catalytic system for preparing highly branched alkane from olefin, which contains novel nickel or palladium complexes. In the presence of the catalytic system, highly branched oily alkane mixture can be efficiently obtained from olefins (such as ethylene) under mild conditions. The alkane mixture has a low bromine number, and can be used as a processing aid(s) and lubricant base oil with high-performance. Provides also was a method for preparing the catalyst and a method for preparing an oily olefin polymer.Type: ApplicationFiled: April 23, 2012Publication date: March 27, 2014Applicant: Shanghai Institute of Organic Chemistry, Chinese Academy of SciencesInventors: Yong Tang, Wenjie Tao, Xiuli Sun, Junfang Li, Zheng Wang
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Publication number: 20140058146Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes processing the acetylene to form a stream having butadiene. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream is be treated to convert acetylene to butadiene. The method according to certain aspects includes controlling the level of carbon monoxide to prevent undesired reactions in downstream processing units.Type: ApplicationFiled: June 11, 2013Publication date: February 27, 2014Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin, Debarshi Majumder
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Publication number: 20140058128Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream is further processed to generate larger hydrocarbons in a second reactor. The reactor effluent stream can be processed before the second reactor to remove waste products such as carbon monoxide and nitrogen in the reactor effluent stream.Type: ApplicationFiled: June 11, 2013Publication date: February 27, 2014Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin
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Publication number: 20140058145Abstract: Methods and systems are provided for converting methane in a feed stream to acetylene. The method includes the further conversion of the acetylene to a hydrocarbon stream having olefins. The hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream is be treated to convert acetylene to another hydrocarbon, and in particular olefins. The method according to certain aspects includes controlling the level of contaminants in the hydrocarbon stream.Type: ApplicationFiled: August 14, 2013Publication date: February 27, 2014Inventors: Jeffery C. Bricker, John Q. Chen, Peter K. Coughlin, John J. Senetar, Debarshi Majumder
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Publication number: 20140051898Abstract: A renewable biofuel based on a highly efficient batch catalysis methodology for conversion of 1-butene to a new class of potential jet fuel blends. By tuning the catalyst and then using the dimer produced, the carbon use is about 95% or greater. This latter point will be particularly important in the future, where the source of raw materials (i.e., biomass/biofeedstock) is limited.Type: ApplicationFiled: February 11, 2013Publication date: February 20, 2014Applicant: US GOVERNMENT AS REPRESENTED BY THE SECRETARY OF DEPARTMENT OF THE NAVYInventors: Michael E. Wright, Benjamin G. Harvey, Roxanne L. Quintana
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Patent number: 8598394Abstract: The present invention relates to poly alpha-olefins (PAO's) which exhibit superior Noack volatility at low pour points. The poly alpha-olefin is prepared from an olefin feed comprised of a blend of octene, decene, and dodecene, the feed comprising at least 10 weight % octene and at least 30 weight % dodecene. The process includes both synthesis and distillation of the olefin and oligomerization olefin. The oligomerized olefin feed yields at least 50% low viscosity PAO having a nominal viscosity at 100° C. of about 4 cSt.Type: GrantFiled: June 30, 2008Date of Patent: December 3, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Maria Caridad Brillantes Goze, Phil Surana, Norman Yang
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Publication number: 20130317265Abstract: This disclosure provides for alpha olefin oligomers and polyalphaolefins (or PAOs) and methods of making the alpha olefin oligomers and PAOs. This disclosure encompasses metallocene-based alpha olefin oligomerization catalyst systems, including those that include at least one metallocene and an activator comprising a solid oxide chemically-treated with an electron withdrawing anion. The alpha olefin oligomers and PAOs prepared with these catalyst systems can have a high viscosity index combined with a low pour point, making them particularly useful in lubricant compositions and as viscosity modifiers.Type: ApplicationFiled: July 31, 2013Publication date: November 28, 2013Applicant: Chevron Phillips Chemical Company LPInventors: Brooke L. Small, Kenneth D. Hope, Qing Yang, Albert P. Masino, Max P. McDaniel, Richard M. Buck, William B. Beaulieu, Eduardo J. Baralt, Eric J. Netemeyer, Bruce Kreischer
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Patent number: 8536391Abstract: This disclosure provides for alpha olefin oligomers and polyalphaolefins (or PAOs) and methods of making the alpha olefin oligomers and PAOs. This disclosure encompasses metallocene-based alpha olefin oligomerization catalyst systems, including those that include at least one metallocene and an activator comprising a solid oxide chemically-treated with an electron withdrawing anion. The alpha olefin oligomers and PAOs prepared with these catalyst systems can have a high viscosity index combined with a low pour point, making them particularly useful in lubricant compositions and as viscosity modifiers.Type: GrantFiled: June 15, 2010Date of Patent: September 17, 2013Assignee: Chevron Phillips Chemical Company LPInventors: Brooke L. Small, Kenneth D. Hope, Qing Yang, Albert P. Masino, Max P. McDaniel, Richard M. Buck, William B. Beaulieu, Eduardo J. Baralt, Eric J. Netemeyer, Bruce Kreischer
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Publication number: 20130225459Abstract: The present invention relates to a low viscosity lubricant process, product, and composition characterized by low Noack volatility, low pour point, useful low temperature viscometrics, and high viscosity index and more particularly concerns a PAO composition having a kinetic viscosity at 100° C. in the range of about 4 cSt.Type: ApplicationFiled: March 28, 2013Publication date: August 29, 2013Applicant: INEOS USA LLCInventor: INEOS USA LLC
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Patent number: 8481796Abstract: A hydrocarbon composition that comprises species of at least 3 different carbon numbers, at least about 95 wt % non-normal hydrocarbons, no greater than 1000 wppm aromatics, no greater than 10 wt % naphthenes, and also has a certain boiling point range; and a process for making the hydrocarbon composition.Type: GrantFiled: January 27, 2006Date of Patent: July 9, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Keith H. Kuechler, Stephen Harold Brown, An Amandine Verberckmoes, Steven E. Silverberg, Marc P. Puttemans, Mark R. Welford, John S. Godsmark
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Publication number: 20130158307Abstract: A low viscosity poly(apha-olefin) (PAO) is produced by contacting one or more C3 to C24 alpha-olefins with an unbridged, substituted bis cyclopentadienyl transition metal compound, a non-coordinating anion activator, and an alkyl-aluminum compound. The molar ratio of transition metal compound to activator is 10:1 to 0.1:1, and the molar ratio of alkyl aluminum compound to transition metal compound is 1:4 to 4000:1. The transition metal compound has either (a) at least one non-isoolefin substitution on both cyclopentadienyl rings, or (b) at least two substitutions on at least one cyclopentadienyl ring. The PAO is comprised of at least 50 mole % of C3 to C24 alpha-olefins and has a kinematic viscosity at 100° C. of 20 cSt or less.Type: ApplicationFiled: May 21, 2012Publication date: June 20, 2013Inventors: Margaret May-Som Wu, Catalina L. Coker, John F. Walzer, JR., Peijun Jiang
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Patent number: 8450549Abstract: The invention provides for methods, compositions and systems using bioisoprene derived from renewable carbon for production of a variety of hydrocarbon fuels and fuel additives.Type: GrantFiled: June 17, 2010Date of Patent: May 28, 2013Assignee: Danisco US Inc.Inventors: Joseph C. McAuliffe, Sergey E. Paramonov, Karl J. Sanford
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Publication number: 20130131410Abstract: This disclosure relates to a liquid syndiotactic polyalphaolefin, sPAO, comprising one or more C4 to C24 monomers, said sPAO having: a) an rr triad content of 5 to 50% as measured by 13C NMR; b) an mr triad content of 25 to 60% as measured by 13C NMR, where the mr to mm triad ratio is at least 1.0; c) a pour point of Z ° C. or less, where Z=0.0648X?51.2, where X=kinematic viscosity at 100° C. as reported in centistokes (cSt); d) a kinematic viscosity at 100° C. of 100 cSt or more (alternatively 200 cSt or more); e) a ratio of mr triads to rr triad (as determined by 13C NMR) of less than 9; f) a ratio of vinylidene to 1,2-disubstituted olefins (as determined by 1H NMR) of less than 8; g) a viscosity index of 120 or more; and h) an Mn of 40,000 or less. This disclosure further relates to processes to make and use sPAOs, including those having any combination of characterics a) to h).Type: ApplicationFiled: January 2, 2013Publication date: May 23, 2013Applicant: ExxonMobil Chemical Patents Inc.Inventors: Margaret May-Som Wu, Steven P. Rucker, Jo Ann M. Canich
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Publication number: 20130090503Abstract: Provided is a process for preparing oligomers from an alkane. The process comprises (a) contacting an alkane under dehydrogenation conditions in the presence of a dehydrogenation catalyst such as an iridium catalyst complex comprising iridium complexed with a benzimidiazolyl-containing ligand to form olefins, and (b) contacting the olefins prepared in step (a) under oligomerization conditions with an oligomerization catalyst such as a nickel, platinum or palladium metal catalyst complex comprising the metal complexed with a nitrogen containing bi- or tridentate ligand to prepare oligomers of the olefins, and hydrogenating the olefin oligomers. In one embodiment, the ligands of the catalyst complexes in step (a) and step (b) can be the same.Type: ApplicationFiled: September 12, 2012Publication date: April 11, 2013Applicants: CHEVRON U.S.A. INC., RUTGERS, THE STATE UNIVERSITY OF NJInventors: Alan Stuart Goldman, Robert Timothy Stibrany, William L. Schinski
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Publication number: 20120209040Abstract: An improved process and apparatus for the selective reaction of terpenes (including mono-, sesqui-, di-terpenes, and others in the terpene family), alpha-olefin oligomers (OOA's), and related olefins to their respective dimeric product in high purity using heterogeneous acid catalyst concurrent with full utilization of energy created in the process. Embodiments of the invention carry out a unique and highly efficient dimerization of terpenes, alpha-olefin oligomers (OOA's), and olefins using cost effective catalysts and low cost equipment that are ideally suited for commercialization of jet/turbine and diesel biofuel processes producing fuels with high flashpoints and superb cold flow properties.Type: ApplicationFiled: March 21, 2012Publication date: August 16, 2012Inventor: Michael E. Wright
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Publication number: 20120197053Abstract: A method of producing liquid fuels by providing an olefin feed containing at least one C2-C20 olefin, oligomerizing a part of the feed in the presence of a first catalyst to form a first product comprising oligomers of the at least one olefin, and oligomerizing a portion of the first product in the presence of a second catalyst to produce a second product. A system of producing liquid hydrocarbons, the system including a first reactor configured to provide a first product by oligomerizing, in the presence of a first catalyst, at least a portion of an olefin feed comprising at least one olefin, a separator configured to provide an unreacted olefin-reduced first product by separating unreacted olefin from the first product, and a second reactor configured to provide a second product by oligomerizing, in the presence of a second catalyst, at least a portion of the unreacted olefin-reduced first product.Type: ApplicationFiled: July 27, 2011Publication date: August 2, 2012Applicant: SYNFUELS INTERNATIONAL., INC.Inventors: Joel CANTRELL, Duane Morrow, Edward R. Peterson
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Patent number: 8188327Abstract: This invention covers a process for dimerizing of isobutylene to Iso-octene and unique configuration is being disclosed, where the Feed is diluted to low level with recycle which has essentially no Iso-octene, dual catalyst system, new selectivator (IPA) and successive catalyst stages if needed to enhance the conversion. The process is very selective and provides higher isobutylene conversion. Additionally the invention also covers the hydrogenation of olefins to Paraffin, Iso-octene to Iso-octane product under moderate conditions and with dual or single catalyst system.Type: GrantFiled: February 1, 2010Date of Patent: May 29, 2012Inventor: Amarjit S. Bakshi
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Patent number: 8178740Abstract: A process for the use in the oligomerization of olefins is presented. The process produces a gasoline boiling range product having a high research octane number and almost no aromatics content. The process utilizes a solid catalyst comprising a zeolite that is treated with a phosphorous containing reagent to generate a catalyst having phosphorous content between 0.5 and 15 wt %.Type: GrantFiled: December 9, 2008Date of Patent: May 15, 2012Assignee: UOP LLCInventors: Christopher P. Nicholas, Laszlo T. Nemeth, Deng-Yang Jan
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Patent number: 8168838Abstract: A process for the preparation of a synthetic predominantly single carbon number hydrocarbon fluid comprises the steps of: contacting an alpha olefin having a carbon number of 4 to 30 with a single site catalyst under conditions effective to produce reactive hydrocarbon oligomers that contain reactive double bonds and comprising predominantly dimers, trimers, and tetramers wherein at least 10 weight percent of such reactive hydrocarbon oligomers at least one of trimers and tetramers; separating at least one of said trimers and tetramers in said reactive hydrocarbon oligomers; dimerizing said separated one of said trimers tetramers by contacting said separated one of said trimers or tetramers with a dimerization catalyst thereby producing an unsaturated synthetic hydrocarbon fluid; and contacting said unsaturated synthetic hydrocarbon fluid with hydrogen in the presence of a hydrogenation catalyst thereby producing a synthetic hydrocarbon fluid having predominantly single carbon number.Type: GrantFiled: January 19, 2010Date of Patent: May 1, 2012Assignee: Shell Oil CompanyInventors: William J Heilman, Yajnanarayana Halmuthur Jois, Abraham Robert De Kraker, Wei Song
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Patent number: 8134039Abstract: A process is described for the production of high-octane hydrocarbon compounds by means of the selective dimerization of isobutene, in the presence of C5 hydrocarbons and oxygenated compounds (branched alcohols or alternatively blends of linear or branched alcohols and alkyl ethers) characterized in that it utilizes a catalytic distillation as second reaction step.Type: GrantFiled: November 14, 2006Date of Patent: March 13, 2012Assignee: Snamprogetti S.p.A.Inventors: Marco Di Girolamo, Domenico Sanfilippo, Massimo Conte
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Patent number: 8124820Abstract: The present invention relates to a process for producing polyolefins wherein a feedstock comprising n-olefin or a mixture of n-olefins is dimerized in the presence of a solid acidic catalyst by passing the feedstock to a catalytic distillation apparatus comprising either a) a combination of a distillation column and a reactor comprising at least one catalyst bed, or b) a distillation column connected to one or more side reactors comprising at least one catalyst layer, recovering the unreacted n-olefin from the distillation column or the combination of the distillation column and the reactor at the upper part thereof as a side-stream to be combined with the feedstock, and the reaction product from the dimerization is hydrogenated.Type: GrantFiled: June 13, 2007Date of Patent: February 28, 2012Assignee: Neste Oil OyjInventors: Marja Tiitta, Anna-Mari Illikainen, Kari Kulmala, Vesa-Matti Lehtinen, Fredrik Nissfolk
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Patent number: 8067655Abstract: This invention is a process for producing diisobutylene from isobutylene. The process comprises first contacting a sulfonic acid resin with a reaction feed comprising isobutylene and tertiary butyl alcohol to produce a product stream comprising diisobutylene, isobutylene, tertiary butyl alcohol, and water. The product stream is distilled to produce a first overhead stream comprising water and isobutylene and a first bottoms stream comprising diisobutylene and tertiary butyl alcohol. Water is separated from the first overhead stream, and the resulting isobutylene-enriched stream is recycled back to the reaction step. The first bottoms stream is distilled to produce a second overhead stream comprising tertiary butyl alcohol and a bottoms product stream comprising diisobutylene.Type: GrantFiled: May 29, 2008Date of Patent: November 29, 2011Assignee: Lyondell Chemical Technology, L.P.Inventors: Natalie C. M. B. Nichols, Christopher P. Renaudo, David W. Leyshon
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Publication number: 20110230690Abstract: A process for oligomerizing olefinic, lower hydrocarbons. The process comprises the steps of feeding a fresh olefinic hydrocarbon feedstock to a reaction zone; contacting the olefinic hydrocarbons of the feedstock with an acidic catalyst in the reaction zone in order to dimerize at least a part of the olefinic hydrocarbons, withdrawing an effluent containing oligomerized olefins from the reaction zone; and conducting the effluent to a separation zone, wherein the oligomerization reaction product is separated from said effluent. According to the invention, the reaction is carried out in homogeneous phase comprising a solvent for olefinic hydrocarbons, maintained at supercritical conditions. By using supercritical carbon dioxide as a solvent deactivation rate of catalyst can be diminished. Carbon dioxide is easy to remove from the product mixture and spent reaction medium can be used for regeneration of the catalyst.Type: ApplicationFiled: August 25, 2008Publication date: September 22, 2011Inventors: Marja Tiita, Helka Turunen, Kaija Isokoski, Antti Pyhalahti
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Publication number: 20110207977Abstract: A method of producing an ?-olefin oligomer composition of the present invention is a method of producing an ?-olefin oligomer composition, the method including the step of causing the molecules of an ?-olefin to react with each other with a specific catalyst in the presence of hydrogen.Type: ApplicationFiled: October 27, 2009Publication date: August 25, 2011Applicant: IDEMITSU KOSAN CO., LTD.Inventors: Shinjiro Fujikawa, Kiyohiko Yokota, Masaki Okano, Minako Tsuji