By Alkyl Transfer, E.g., Disproportionation, Etc. Patents (Class 585/643)
  • Patent number: 11926587
    Abstract: Disclosed herein is a process for upgrading a raffinate butene (C4 Raffinate) stream to propylene which can produce polymer grade propylene (PGP) by a metathesis process, without consuming fresh ethylene as a feedstock. By recycling ethylene byproduct in the metathesis equilibrium, propylene selectivity can be further improved without negatively impacting butene conversion. Additionally, upon PGP separation, this technology can provide an effluent acceptable for alkylate production by achieving a balanced butene conversion and heavies coproduction. The disclosed process is a relatively low temperature process which can be deployed as a drop-in option for conventional ethylene/butene metathesis unit and provide additional flexibility to existing operations to balance the supply and demand of C2-C4 light olefins.
    Type: Grant
    Filed: September 14, 2021
    Date of Patent: March 12, 2024
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Lei Zhang, Pranit S. Metkar, Majid Keyvani, Daniel F. White
  • Patent number: 11858872
    Abstract: Disclosed herein are processes and systems that utilize olefin cross metathesis of triglycerides to produce jet fuel such as hydrocarbons with carbons numbers from C9 to C16. Jet range hydrocarbons may include paraffins, naphthenes, and aromatics with carbon numbers from 9 to 16 (C9-C16), and isomers thereof. The process described herein is versatile and may be suitable for producing jet range hydrocarbons from many different grades and sources of triglycerides. Further, the process described herein may be selective to jet range hydrocarbons which may result in increased yield as compared to hydrocracking or other processes for producing jet range hydrocarbons from triglycerides.
    Type: Grant
    Filed: March 30, 2021
    Date of Patent: January 2, 2024
    Assignee: ExxonMobil Technology and Engineering Company
    Inventor: Patrick L. Hanks
  • Patent number: 11565985
    Abstract: Systems and processes herein improve the conversion of propylene to ethylene via metathesis. On a mass basis, embodiments herein may be used to convert greater than 40% propylene, on a mass basis, to ethylene, such as 43% to 75%, on a mass basis. In one aspect, processes for the conversion of propylene to ethylene herein may include introducing a propylene feed stream to a metathesis reactor, and contacting the propylene with a metathesis catalyst in the metathesis reactor to convert the propylene to ethylene and 2-butene. An effluent from the metathesis reactor may be recovered, the effluent including ethylene, 2-butene, and unconverted propylene. The effluent may then be separated in a fractionation system to recover an ethylene fraction, a propylene fraction, a c4 fraction, and a C5+ fraction. The propylene fraction and the C4 fraction may then be fed to the metathesis reactor to produce additional ethylene.
    Type: Grant
    Filed: November 20, 2020
    Date of Patent: January 31, 2023
    Assignee: LUMMUS TECHNOLOGY LLC
    Inventor: Bala Ramachandran
  • Patent number: 11339332
    Abstract: Processes for producing olefins include introducing a hydrocarbon feed to a high-severity fluidized catalytic cracking system, contacting the hydrocarbon feed with a cracking catalyst under high-severity conditions in the high-severity fluidized catalytic cracking system to produce a cracking reaction effluent comprising butene, and passing at least a portion of the cracking reaction effluent, which includes at least butene, to a metathesis system. The processes further include contacting the portion of the cracking reaction effluent with a metathesis catalyst in the metathesis system, which causes at least a portion of the butene in the cracking C4 effluent to undergo a metathesis reaction to produce a metathesis reaction effluent comprising at least one of ethylene, propene, or both. The processes may further include separating a metathesis C5+ effluent from the metathesis reaction effluent and passing the metathesis C5+ effluent back to the high-severity fluidized catalytic cracking unit.
    Type: Grant
    Filed: January 29, 2020
    Date of Patent: May 24, 2022
    Assignee: Saudi Arabian Oil Company
    Inventors: Sohel K. Shaikh, Raed H. Abudawoud, Zhonglin Zhang, Munir D. Khokhar, Furqan Aljumah
  • Patent number: 10961171
    Abstract: Embodiments of methods of synthesizing a metathesis catalyst system, which include impregnating tungsten oxide on silica support in the presence of a precursor to produce a base catalyst; calcining the base catalyst; dispersing a solid metal-based co-catalyst onto the surface of the base catalyst to produce a doped catalyst; and calcining the doped catalyst to produce a metathesis catalyst system. Further embodiments of processes for the production of propylene, which include contacting a hydrocarbon feedstock comprising a mixture of 1-butene and 2-butene with embodiments of the metathesis catalyst system to produce, via metathesis conversion, a product stream comprising propylene.
    Type: Grant
    Filed: October 10, 2018
    Date of Patent: March 30, 2021
    Assignee: Saudi Arabian Oil Company
    Inventors: Munir D. Khokhar, Mohammed R. Alalouni, Noor A. Sulais, Brian Hanna, Sohel K. Shaikh
  • Patent number: 10583423
    Abstract: Embodiments of processes for producing propylene utilize a dual catalyst system comprising a mesoporous silica catalyst impregnated with metal oxide and a mordenite framework inverted (MFI) structured silica catalyst downstream of the mesoporous silica catalyst, where the mesoporous silica catalyst includes a pore size distribution of at least 2.5 nm to 40 nm and a total pore volume of at least 0.600 cm3/g, and the MFI structured silica catalyst has a total acidity of 0.001 mmol/g to 0.1 mmol/g. The propylene is produced from the butene stream via metathesis by contacting the mesoporous silica catalyst and subsequent cracking by contacting the MFI structured silica catalyst.
    Type: Grant
    Filed: July 19, 2018
    Date of Patent: March 10, 2020
    Assignees: Saudi Arabian Oil Company, King Fahd University of Petroleum & Minerals
    Inventors: Sulaiman Saleh Al-Khattaf, Arudra Palani, Tazul Islam Bhuiyan, Sohel Shaikh, Mohammad Naseem Akhtar, Abdullah M. Aitani, Mohammed A. Al-Yami
  • Patent number: 10456764
    Abstract: A catalyst bed configuration, in particular for olefin conversion by metathesis, comprising at least one main catalyst bed comprising a) at least one first catalyst component comprising a metathesis catalyst, and b) at least one second catalyst component comprising a catalyst for double bond isomerization, whereby the first and second catalyst are intimate mixed with each other, and at least one catalyst pre-bed arranged upstream of the at least one main catalyst bed comprising at least one compound selected from the group of alkaline earth oxides. The mass ratio of the at least one catalyst pre-bed to the at least one main catalyst bed is between 1:2 and 2.5:1, preferably between 1:1.5 and 2.5:1, more preferably between 1:1 and 2.5:1, most preferably between 1:1 and 2:1.
    Type: Grant
    Filed: July 22, 2014
    Date of Patent: October 29, 2019
    Assignee: Borealis AG
    Inventors: Eberhard Ernst, Mariana Stoyanova, Evgeny Kondratenko, David Linke
  • Patent number: 10308572
    Abstract: Embodiments of the present disclosure provide for methods of using a catalytic system to chemically transform a compound (e.g., a hydrocarbon). In an embodiment, the method does not employ grafting the catalyst prior to catalysis. In particular, embodiments of the present disclosure provide for a process of hydrocarbon (e.g., C1 to C20 hydrocarbon) metathesis (e.g., alkane, olefin, or alkyne metathesis) transformation, where the process can be conducted without employing grafting prior to catalysis.
    Type: Grant
    Filed: June 23, 2016
    Date of Patent: June 4, 2019
    Assignee: KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY
    Inventors: Jean-Marie Maurice Basset, Emmanuel Callens, Nassima Riache
  • Patent number: 10052618
    Abstract: Embodiments of processes for producing propylene utilize a dual catalyst system comprising a mesoporous silica catalyst impregnated with metal oxide and a mordenite framework inverted (MFI) structured silica catalyst downstream of the mesoporous silica catalyst, where the mesoporous silica catalyst includes a pore size distribution of at least 2.5 nm to 40 nm and a total pore volume of at least 0.600 cm3/g, and the MFI structured silica catalyst has a total acidity of 0.001 mmol/g to 0.1 mmol/g. The propylene is produced from the butene stream via metathesis by contacting the mesoporous silica catalyst and subsequent cracking by contacting the MFI structured silica catalyst.
    Type: Grant
    Filed: January 4, 2017
    Date of Patent: August 21, 2018
    Assignees: Saudi Arabian Oil Company, King Fahd University of Petroleum & Minerals
    Inventors: Sulaiman Saleh Al-Khattaf, Arudra Palani, Tazul Islam Bhuiyan, Sohel Shaikh, Mohammad Naseem Akhtar, Abdullah M. Aitani, Mohammed A. Al-Yami
  • Patent number: 10029959
    Abstract: The present invention relates to a process for obtaining an olefin by metathesis comprising feeding at least one stream comprising at least one olefin as starting material to at least one reactor comprising at least one main catalyst bed comprising a) at least one first catalyst component comprising a metathesis catalyst, and b) at least one second catalyst component comprising a catalyst for double bond isomerization, whereby the first and second catalyst are physically mixed with each other, wherein the at least one stream comprising at least one olefin as starting material is co-fed with hydrogen gas in a concentration range between 0.01 Vol % and 0.2 Vol % in respect to the total gas amount in the stream, and the metathesis process is conducted in the at least one reactor at a pressure between 0.1 MPa and 3.0 MPa and at a temperature between 250° C. and 300° C.
    Type: Grant
    Filed: December 30, 2014
    Date of Patent: July 24, 2018
    Assignee: Borealis AG
    Inventors: Mariana Stoyanova, Evgeny Kondratenko, David Linke, Eberhard Ernst, Rene Dicke
  • Patent number: 9815753
    Abstract: A method is provided comprising exposing a supported heterogeneous metathesis catalyst to an olefin compound for an activation time at an activation temperature; exposing the activated supported heterogeneous metathesis catalyst to a reactant capable of undergoing a metathesis reaction for a reaction time at a reaction temperature to produce metathesis products; and exposing the deactivated supported heterogeneous metathesis catalyst to a regenerating compound for a regeneration time at a regeneration temperature. The activity of the regenerated supported heterogeneous metathesis catalyst may be substantially the same or greater than the activity of the activated supported heterogeneous metathesis catalyst prior to deactivation. The activation temperature may be greater than the reaction temperature. The regenerating compound may be a second olefin compound or an inert gas.
    Type: Grant
    Filed: September 14, 2015
    Date of Patent: November 14, 2017
    Assignee: Northwestern University
    Inventors: Kunlun Ding, Peter C. Stair
  • Patent number: 9695096
    Abstract: A process for the conversion of linear pentenes to propylene is disclosed. The process may include feeding hydrogen and a C5-olefin containing stream comprising linear pentenes, dienes, acetylenes, and cyclopentene to a catalytic distillation reactor system. Concurrently in the catalytic distillation reactor system, the acetylenes and dienes may be hydrogenated and the C5-olefin containing stream may be fractionated, thereby recovering an overheads fraction comprising the linear pentenes, a side draw fraction comprising the cyclopentene, and a bottoms fraction. In some embodiments, at least a portion of the overheads fraction may then be fed to a metathesis reactor for converting the linear pentenes to propylene.
    Type: Grant
    Filed: July 12, 2012
    Date of Patent: July 4, 2017
    Assignee: Lummus Technology Inc.
    Inventors: Yongqiang Xu, Gary G. Podrebarac
  • Patent number: 9242908
    Abstract: A process for the production of C4 olefins, which may include: contacting a hydrocarbon mixture comprising alpha-pentenes with an isomerization catalyst to form an isomerization product comprising beta-pentenes; contacting ethylene and the beta-pentenes with a first metathesis catalyst to form a first metathesis product comprising butenes and propylene, as well as any unreacted ethylene and C5 olefins; and fractionating the first metathesis product to for an ethylene fraction, a propylene fraction, a butene fraction, and a C5 fraction.
    Type: Grant
    Filed: November 20, 2014
    Date of Patent: January 26, 2016
    Assignee: Lummus Technology Inc.
    Inventors: Sukwon Choi, Bala Ramachandran
  • Patent number: 8993823
    Abstract: A process for the metathesis of olefins has been developed. The process comprises contacting a hydrocarbon feedstock with a catalyst at metathesis conditions. The catalyst comprises a tungsten compound, which contains at least one tungsten-fluoro bond, dispersed or grafted onto a support. A specific example of the catalyst is the compound WOF(CH2CMe3)3 grafted onto a silica support. The feedstock comprises a first and a second olefin wherein the second olefin has a carbon number of at least two greater than the first olefin and the product is an olefin with a carbon number intermediate between the first and second olefin. Specifically the process produces propylene from ethylene and butylene.
    Type: Grant
    Filed: June 25, 2014
    Date of Patent: March 31, 2015
    Assignee: UOP LLC
    Inventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
  • Publication number: 20150087866
    Abstract: The present invention relates to the process of production of olefins by means of the dehydration of light alcohols using ionic liquids as an acidic medium. Furthermore, the present invention relates to the use of such olefins, for example, for the production of polymers and ethylene glycol.
    Type: Application
    Filed: August 30, 2012
    Publication date: March 26, 2015
    Applicants: UNIVERSIDADE FEDERAL DO RIO GRANDE DO SUL-UFRGS, BRASKEM S.A.
    Inventor: Michèle Oberson De Souza
  • Patent number: 8933285
    Abstract: Methods are provided for producing a jet fuel composition from a feedstock comprising a natural oil. The methods comprise reacting the feedstock with a low-weight olefin in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product. The methods further comprise hydrogenating the metathesized product under conditions sufficient to form a jet fuel composition.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: January 13, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Melvin L. Luetkens, Jr., Steven A. Cohen, Chander Balakrishnan
  • Publication number: 20140357922
    Abstract: A process for the metathesis of olefins has been developed. The process comprises contacting a hydrocarbon feedstock with a catalyst at metathesis conditions. The catalyst comprises a tungsten compound, which contains at least one tungsten-fluoro bond, dispersed or grafted onto a support. A specific example of the catalyst is the compound WOF(CH2CMe3)3 grafted onto a silica support. The feedstock comprises a first and a second olefin wherein the second olefin has a carbon number of at least two greater than the first olefin and the product is an olefin with a carbon number intermediate between the first and second olefin. Specifically the process produces propylene from ethylene and butylene.
    Type: Application
    Filed: June 25, 2014
    Publication date: December 4, 2014
    Inventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
  • Patent number: 8895794
    Abstract: We provide a process for producing high quality gasoline blending components, comprising: a) operating an alkylation reactor in an alkylate mode wherein a gasoline blending component is made having a RON of 90 or higher; and b) operating the alkylation reactor in a distillate mode wherein a second gasoline blending component and a distillate product is made, and wherein the second gasoline blending component has a RON of 85 or higher. Also, we provide an alkylation process unit, comprising: a control system connected to an alkylation reactor, that enables the alkylation reactor to operate in both an alkylate mode that produces a gasoline blending component having a RON of 90 or higher and in a distillate mode that produces a second gasoline blending component having a RON of 85 or higher.
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: November 25, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventors: Hye-Kyung Timken, Shawn Winter, Howard S. Lacheen, Sven Ivar Hommeltoft
  • Patent number: 8859779
    Abstract: Catalytic complexes including a metal atom having anionic ligands, at least one nucleophilic carbene ligand, and an alkylidene, vinylidene, or allenylidene ligand. The complexes are highly stable to air, moisture and thermal degradation. The complexes are designed to efficiently carry out a variety of olefin metathesis reactions.
    Type: Grant
    Filed: January 25, 2013
    Date of Patent: October 14, 2014
    Assignee: Materia, Inc.
    Inventors: Steven P. Nolan, Jinkun Huang
  • Patent number: 8772562
    Abstract: A process for converting feedstock triglycerides to lube basestocks. The process has the steps of (a) metathesizing the feedstock triglycerides with ethylene in the presence of a metathesis catalyst to form alpha olefins and medium-chain triglycerides and (b) hydroisomerizing the medium-chain triglycerides in the presence of a hydroisomerization catalyst and hydrogen to form methyl-branched triglycerides. The alpha olefins may be oligomerized in the presence of an oligomerization catalyst to form poly(alpha olefins).
    Type: Grant
    Filed: November 10, 2010
    Date of Patent: July 8, 2014
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Kun Wang, Margaret May-Som Wu, Alan Anthony Galuska, David Lawrence Stern
  • Patent number: 8742186
    Abstract: Described herein is a process for producing an alpha olefin by obtaining a feed stream of internal olefins having a first carbon number and alpha olefins having a first carbon number. The olefins are isomerized to increase the quantity of the alpha olefins. The olefins are then fractionated, subjecting the overhead material to catalytic metathesis to produce a mixed olefin effluent of internal olefins having a second carbon number and other hydrocarbons. The first isomerization reactor and fractionator are prepared to receive the olefins having a second carbon number, where the internal olefin intermediate is isomerized in the prepared first isomerization reactor. The second isomerization effluent is fractionated in the prepared first fractionator to separate the alpha olefins having the second carbon number from the internal olefins having the second carbon number. A corresponding system is also described, along with a heat pump that may be incorporated into the process.
    Type: Grant
    Filed: April 2, 2009
    Date of Patent: June 3, 2014
    Assignee: Lummus Technology Inc.
    Inventors: Robert J. Gartside, Shaun M. McGovern, Thulasidas Chellppannair
  • Patent number: 8735640
    Abstract: Methods are provided for refining natural oil feedstocks. The methods comprise reacting the feedstock with a low-molecular-weight olefin or mid-weight olefin in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters. In certain embodiments, the methods further comprise separating the olefins from the esters in the metathesized product. In certain embodiments, the methods further comprise transesterifying the esters in the presence of an alcohol to form a transesterified product.
    Type: Grant
    Filed: October 9, 2012
    Date of Patent: May 27, 2014
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Steven A. Cohen, Melvin L. Luetkens, Jr., Chander Balakrishnan, Robert Snyder, Yenamandra Viswanath, Efimia Metsi-Guckel, Robin Weitkamp
  • Patent number: 8729283
    Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.
    Type: Grant
    Filed: January 15, 2013
    Date of Patent: May 20, 2014
    Assignee: Energy & Environmental Research Center Foundation
    Inventor: Edwin S. Olson
  • Patent number: 8722950
    Abstract: The invention is for a process for producing propylene and hexene (along with ethylene, pentenes, product butenes, heptenes and octenes) by metathesis from butenes (iso-, 1- and cis and trans 2-) and pentenes and then aromatizing the hexenes (along with higher olefins, such as heptenes and octenes) to benzene (along with toluene, xylenes, ethylbenzene and styrene). Since the desired products of the metathesis reaction are propylene and hexene, the feed to the metathesis reaction has a molar ratio for 1-butene:2-butene which favors production of propylene and 3-hexene with the concentration of hexenes and higher olefins in the metathesis product being up to 30 mole %. An isomerization reactor may be used to obtain the desired molar ratio of 1-butene:2-butene for the feed composition into the metathesis reactor. After the metathesis reaction, of hexene and higher olefins are separated for aromatization to benzene and other aromatics.
    Type: Grant
    Filed: April 26, 2010
    Date of Patent: May 13, 2014
    Assignee: Saudi Basic Industries Corporation
    Inventors: Jaap W. van Hal, Scott A. Stevenson, Jim Allman, David L. Sullivan, Travis Conant
  • Patent number: 8704029
    Abstract: Processes for the conversion, under conditions and with a catalyst system effective for olefin metathesis, of hydrocarbon feedstocks comprising butylene, for example all or a large proportion of a single C4 olefin isomer such as butene-1, are described. Olefin products, and particularly propylene, are formed in the presence of a catalyst comprising a solid support and a tungsten hydride bonded to alumina present in the support. This occurs despite the expectation that the olefin metathesis reaction mechanism leads to the formation of olefin products having other carbon numbers.
    Type: Grant
    Filed: March 30, 2010
    Date of Patent: April 22, 2014
    Assignee: UOP LLC
    Inventors: Christopher P. Nicholas, Etienne Mazoyer, Mostafa Taoufik, Jean-Marie Basset, Paul T. Barger, James E. Rekoske
  • Patent number: 8704028
    Abstract: Processes for the conversion, under conditions and with a catalyst system effective for olefin metathesis, of hydrocarbon feedstocks comprising an acyclic symmetrical olefin (e.g., butene-2) are described. Olefin products of lower and higher carbon numbers (e.g., propylene and pentene) are formed in the presence of a catalyst comprising a solid support and a tungsten hydride bonded to alumina present in the support. This occurs despite the olefin metathesis reaction mechanism leading to a degenerative result, without any expected production of different carbon number products from acyclic symmetrical olefins.
    Type: Grant
    Filed: March 30, 2010
    Date of Patent: April 22, 2014
    Assignee: UOP LLC
    Inventors: Christopher P. Nicholas, Etienne Mazoyer, Mostafa Taoufik, Jean-Marie Basset, Paul T. Barger
  • Publication number: 20140094634
    Abstract: The invention describes a radial bed catalytic conversion unit having an outer cylindrical chamber (1), an inner chamber (2) which is also cylindrical, the annular zone included between the outer chamber and the inner chamber, termed the reaction zone (1), being filled with catalyst under slow gravitational flow, and the feed being introduced via an inlet pipe (E), connected to an intermediate box (F) which is in turn connected to a plurality of distribution tubes (3) disposed inside the reaction zone (I) in the vicinity of the outer chamber (1).
    Type: Application
    Filed: December 6, 2013
    Publication date: April 3, 2014
    Applicant: IFP Energies Nouvelles
    Inventors: Eric SANCHEZ, Gilles FERSCHNEIDER, Frederic BAZER-BACHI
  • Patent number: 8674155
    Abstract: Systems and methods for processing one or more hydrocarbons are provided. In one or more embodiments, the method can include thermally converting a hydrocarbon comprising methane to produce a first product comprising acetylene. The method can also include hydrogenating the first product to produce a second product comprising ethylene. The method can further include catalytically reacting the second product with one or more butene products to produce a third product comprising propylene.
    Type: Grant
    Filed: December 22, 2010
    Date of Patent: March 18, 2014
    Assignee: Kellogg Brown & Root, LLC
    Inventor: Curtis N. Eng
  • Patent number: 8647999
    Abstract: A method for manufacturing a catalyst, which comprises regenerating a catalyst comprising a CHA zeolite as an active ingredient and having an ethylene conversion lowered through reaction of producing propylene by bringing into contact with ethylene in a vapor phase, by bringing the catalyst into contact with a gas which does not comprise oxygen and comprises hydrogen having a hydrogen partial pressure of 0.01 MPa or more as an absolute pressure thereof.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: February 11, 2014
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Mikio Hayashi, Masahiro Hara, Masashi Yamaguchi, Yumiko Yoshikawa, Takahiko Takewaki, Tohru Setoyama, Naoyuki Sakamoto
  • Publication number: 20130331630
    Abstract: A method for suppressing dehydrogenation includes reacting an optionally functionalized olefin reactant in a metathesis reaction to form an olefin metathesis product; and providing a dehydrogenation suppression agent in admixture with (a) the olefin metathesis product and/or the optionally functionalized olefin reactant, and (b) a metal-containing material selected from the group consisting of residual metathesis catalyst, a hydrogen transfer agent, and a combination thereof, under conditions that are sufficient to passivate at least a portion of the metal-containing material. Methods of refining natural oils and methods of producing fuel compositions are also described.
    Type: Application
    Filed: June 6, 2013
    Publication date: December 12, 2013
    Inventors: Bradon J. Dreyer, Brian M. Pease
  • Patent number: 8569560
    Abstract: This disclosure relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by an olefin metathesis catalyst. According to one aspect, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting, in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with a cross metathesis partner comprised of an alpha olefinic reactant, under reaction conditions effective to allow cross-metathesis to occur, wherein the reaction conditions include a reaction temperature of at least 35° C. The methods, compositions, reactions and reaction systems herein disclosed have utility in the fields of catalysis, organic synthesis, and industrial chemistry.
    Type: Grant
    Filed: September 19, 2012
    Date of Patent: October 29, 2013
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Yann Schrodi, Richard L. Pederson, Hiroki Kaido, Michael J. Tupy
  • Publication number: 20130274533
    Abstract: Disclosed herein are processes in which precipitation permits removal of metal halides (e.g. AlCl3) from ionic liquids. After precipitation, the precipitated metal halides can be physically separated from the bulk ionic liquid. More effective precipitation can be achieved through cooling or the combination of cooling and the provision of metal halide seed crystals. The ionic liquids can be regenerated ionic liquid catalysts, which contain excess metal halides after regeneration. Upon removal of the excess metal halides, they can be reused in processes using ionic liquid catalysts, such as alkylation processes.
    Type: Application
    Filed: March 14, 2013
    Publication date: October 17, 2013
    Applicant: Chevron U.S.A. Inc.
    Inventors: Moinuddin Ahmed, Huping Luo, Krishniah Parimi, Bong-Kyu Chang, Sara Lindsay
  • Publication number: 20130261312
    Abstract: Supported olefin metathesis catalysts are disclosed, and more particularly, a supported catalyst complex comprising a catalyst composed of a Group 8 transition metal complex comprising a labile ligand and a non-labile ligand and a support, wherein the metal complex and the support are linked together by one or more linkers, in which one of the linkers connects the labile ligand of the complex to the support and the same or a different linker connects the non-labile ligand of the complex to the support. A method for preparing a supported catalyst complex is further disclosed. The invention further relates to the use of the supported olefin metathesis catalyst in performing metathesis reactions. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.
    Type: Application
    Filed: June 4, 2012
    Publication date: October 3, 2013
    Applicant: MATERIA, INC.
    Inventors: DARYL ALLEN, MICHAEL GIARDELLO
  • Patent number: 8487154
    Abstract: A process comprising adjusting a level of conjunct polymers in an ionic liquid catalyst between a low level that favors production of C5+ products boiling at 137.8° C. or below and a higher level that favors production of both C5+ products boiling at 137.8° C. or below and C5+ products boiling above 137.8° C.; wherein the adjusting is done in response to market demand. A process unit, comprising a reactor that operates with an ionic liquid catalyst comprising a low level or a higher level of conjunct polymers, and the alkylation reactor is switched between operating with the low and the higher levels in response to market demand. A process unit, comprising a reactor that operates in an alkylate mode and a distillate mode, and a catalyst regenerator that operates with varying severity to adjust the level of conjunct polymers in response to demand for gasoline or distillate.
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: July 16, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Hye-Kyung Timken, Shawn Winter, Howard S. Lacheen, Sven Ivar Hommeltoft
  • Publication number: 20130150643
    Abstract: Methods for olefin metathesis including contacting a olefin feed stream with a metathesis catalyst at a temperature and at a pressure sufficient to maintain the reactor olefin compositions in a mixed-phase condition including components in the liquid phase and components in the vapor phase, where the mixed-phase reaction conditions shift the equilibrium to desired product olefins.
    Type: Application
    Filed: December 8, 2011
    Publication date: June 13, 2013
    Applicant: SAUDI BASIC INDUSTRIES CORPORATION
    Inventors: Travis Conant, Scott A. Stevenson
  • Patent number: 8455708
    Abstract: A process for producing hydrocarbon products, comprising: a) operating a process unit in an alkylate mode wherein greater than 50 wt % of a C5+ hydrocarbon stream from the process unit boils at 137.8° C. or below, b) adjusting one or more process conditions in the process unit, and c) after the adjusting step, operating the process unit in a distillate mode wherein greater than 50 wt % of the C5+ hydrocarbon stream from the process unit boils above 137.8° C. Also, a process unit, comprising: a) an alkylation reactor; and b) a control system that enables the alkylation reactor to be operated in the alkylate mode and in the distillate mode; wherein the alkylation reactor can switch back and forth from operating in the alkylate mode to the distillate mode.
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: June 4, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Hye-Kyung Timken, Shawn Winter, Howard S. Lacheen, Sven Ivar Hommeltoft
  • Patent number: 8450551
    Abstract: The present invention provides in a method for producing propylene from a hydrocarbon raw material containing ethylene in an amount exceeding 50% by mass under the co-existence of water, a method for producing propylene stably over a long term from ethylene in a high yield and with the reaction/regeneration repeated. A method for producing propylene includes a step for catalytically converting a hydrocarbon raw material containing ethylene in an amount exceeding 50% by mass with a zeolite-containing catalyst while supplying water, wherein a zeolite contained in the zeolite-containing catalyst satisfies (1) to (3) shown below; (1) the zeolite is an MFI zeolite, (2) a zeolite crystallization index obtained from an X-ray diffraction spectrum is 3.3 or more, and (3) a molar ratio of silica/alumina (SiO2/Al2O3) is 20 to 300.
    Type: Grant
    Filed: March 1, 2010
    Date of Patent: May 28, 2013
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Yoshikazu Takamatsu, Ryusuke Miyazaki
  • Patent number: 8440874
    Abstract: A process for the production of propylene, the process including: contacting ethylene and a hydrocarbon stream comprising 1-butene and 2-butene with a bifunctional isomerization-metathesis catalyst to concurrently isomerizes 1-butene to 2-butene and to form a metathesis product comprising propylene; wherein the bifunctional isomerization-metathesis catalyst comprises: a catalyst compound may include at least one element selected from tungsten, tantalum, niobium, molybdenum, nickel, palladium, osmium, iridium, rhodium, vanadium, ruthenium, and rhenium for providing metathesis activity on a support comprising at least one element from Group IA, IIA, IIB, and IIIA of the Periodic Table of the Elements; wherein an exposed surface area of the support provides both isomerization activity for the isomerization of 1-butene to 2-butene; and reactive sites for the adsorption of catalyst compound poisons.
    Type: Grant
    Filed: September 4, 2009
    Date of Patent: May 14, 2013
    Assignees: Lummus Technology Inc., BASF Corporation
    Inventors: Bala Ramachandran, Sukwon Choi, Robert J. Gartside, Shane Kleindienst, Wolfgang Ruettinger, Saeed Alerasool
  • Publication number: 20130066130
    Abstract: Ionic liquid alkylation processes may comprise contacting at least one hydrocarbon stream with an ionic liquid catalyst in an ionic liquid alkylation zone under ionic liquid alkylation conditions, cooling at least one of a reactor effluent and a hydrocarbon phase of the reactor effluent, and recycling the cooled reactor effluent or cooled hydrocarbon phase to the ionic liquid alkylation zone. Ionic liquid alkylation systems for performing ionic liquid catalyzed alkylation processes are also disclosed.
    Type: Application
    Filed: September 12, 2011
    Publication date: March 14, 2013
    Applicant: Chevron U.S.A. Inc.
    Inventors: Huping Luo, Moinuddin Ahmed
  • Patent number: 8395005
    Abstract: A process for producing propylene and 1-butene is disclosed. The process comprises dimerizing ethylene in the presence of a dimerization catalyst to produce a dimerization mixture comprising 1-butene and 2-butenes. The dimerization mixture is distilled to produce a 1-butene stream containing 1-butene and ethylene, a 2-butenes stream, and a heavy stream. The 2-butenes stream is reacted with ethylene in the presence of a metathesis catalyst to produce a metathesis mixture comprising propylene, ethylene, and 2-butenes. Propylene is separated from the metathesis mixture.
    Type: Grant
    Filed: October 13, 2010
    Date of Patent: March 12, 2013
    Assignees: Equistar Chemicals, LP, Lyondell Chemical Technology, L.P.
    Inventors: Steven T. Coleman, Gary A. Sawyer, Robert S. Bridges
  • Patent number: 8389788
    Abstract: Processes for olefin metathesis, for example for the production of propylene, utilize a catalyst comprising a solid support and a tungsten hydride bonded to alumina present in the support. Conversion, selectivity, and/or catalyst stability advantages may be realized when a first olefin reactant (e.g., ethylene) is present in the hydrocarbon feedstock at a stoichiometric deficit relative to a second, higher carbon number olefin reactant (e.g., butylene).
    Type: Grant
    Filed: March 30, 2010
    Date of Patent: March 5, 2013
    Assignee: UOP LLC
    Inventors: Mostafa Taoufik, Etienne Mazoyer, Christopher P. Nicholas, Jean-Marie Basset
  • Patent number: 8389784
    Abstract: Ethanol obtained from ordinary biomass resources contains many impurities other than water and these impurities themselves or their decomposition products contaminate ethylene when the ethylene is produced by a dehydration reaction, whereby the activity of metathesis catalyst is adversely affected. A method for producing propylene of the present invention is characterized in that the ethanol obtained from biomass is converted to ethylene by a dehydration reaction, the ethylene is separated from the generated water, the separated ethylene is purified by adsorption in an adsorption tower filled with an adsorbent, and then a metathesis reaction is carried out along with a raw material containing n-butene. With the present invention, propylene having biomass-derived carbon and reduced-environmental burden can be efficiently produced without lowering the catalysis activity.
    Type: Grant
    Filed: November 13, 2006
    Date of Patent: March 5, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Toshihiro Takai, Daisuke Mochizuki, Michiaki Umeno
  • Publication number: 20130035532
    Abstract: This disclosure relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by an olefin metathesis catalyst. According to one aspect, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting, in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with a cross metathesis partner comprised of an alpha olefinic reactant, under reaction conditions effective to allow cross-metathesis to occur, wherein the reaction conditions include a reaction temperature of at least 35° C. The methods, compositions, reactions and reaction systems herein disclosed have utility in the fields of catalysis, organic synthesis, and industrial chemistry.
    Type: Application
    Filed: September 19, 2012
    Publication date: February 7, 2013
    Applicant: Elevance Renewable Sciences. Inc
    Inventor: Elevance Renewable Sciences. Inc
  • Patent number: 8324440
    Abstract: Silica supports having a surface area from about 250 m2/g to about 600 m2/g and an average pore diameter from about 45 ? to about 170 ?, used for supported tungsten catalysts, improves the activity of the resulting catalyst (i.e., its conversion level at a given temperature) for the metathesis of olefins, without compromising its selectivity to the desired conversion product(s). Exemplary catalysts and processes include those for the production of valuable light olefins such as propylene from a hydrocarbon feedstock comprising ethylene and butylene.
    Type: Grant
    Filed: February 5, 2010
    Date of Patent: December 4, 2012
    Assignee: UOP LLC
    Inventors: Kristoffer E. Popp, Mark A. Krawczyk, Christopher P. Nicholas, Jennifer F. Abrahamian
  • Patent number: 8314278
    Abstract: Disclosed herein is a process for producing isoprene that includes reacting a mixed C4 metathesis feed stream comprising isobutylene and at least one of 1-butene and 2-pentene in a first metathesis reactor in the presence of a first metathesis catalyst under conditions sufficient to produce an intermediate product stream comprising at least 30 wt. % 2-methyl-2-pentene based upon the olefin content of fresh feed in the mixed C4 feed stream, and at least one of ethylene and propylene, separating the 2-methyl-2-pentene, subjecting the separated 2-methyl-2-pentene to pyrolysis to produce a reaction product stream comprising isoprene, and separating the isoprene into an isoprene product stream using fractionation. A system used in producing isoprene is also disclosed.
    Type: Grant
    Filed: May 8, 2012
    Date of Patent: November 20, 2012
    Assignee: Lummus Technology Inc.
    Inventors: Robert J Gartside, Shane R Kleindienst
  • Patent number: 8288604
    Abstract: A method of rapid methylation of an aromatic compound or an alkenyl compound, which is capable of obtaining an aromatic compound or an alkenyl compound labeled with a methyl group or a fluoromethyl group under a mild condition rapidly in high yield using an organic boron compound whose toxicity is not so high as a substrate. A kit for preparing a PET tracer and a method of producing a PET tracer can be practiced using the rapid methylation method. In an aprotic polar solvent, methyl iodide or X—CH2F (wherein X is a functional group which can be easily released as an anion), and an organic boron compound in which an aromatic ring or an alkenyl group is attached to boron are subjected to cross-coupling in the presence of a palladium(0) complex, a phosphine ligand, and a base.
    Type: Grant
    Filed: August 24, 2007
    Date of Patent: October 16, 2012
    Assignees: Gifu University, Riken, Hamamatsu Photonics K.K.
    Inventors: Masaaki Suzuki, Hisashi Doi, Hideo Tsukada
  • Publication number: 20120232321
    Abstract: A method for synthesis of 1-decene oligomer is provided, wherein 1-decene is polymerized at 80-120° C., 0.8-1.4 MPa in the presence of aluminum trichloride catalyst supported on gamma-alumina and n-hexane solvent where the volume ratio of 1-decene to n-hexane is 3:8-4:1. The catalyst is treated as follows: impregnating gamma-alumina carrier in 0.5-2.0 mol of hydrochloric acid, sulfuric acid, nitric acid or mixtures thereof, then vacuum drying at 80-100° C. and calcining at 400-800° C.; dissolving 5-10 g of anhydrous aluminum trichloride in 100 ml of tetrachloromethane, trichloromethane or dichloromethane solvent; adding the obtained solution into 10-20 g of activated alumina carrier and obtaining the catalyst after vacuum drying. The conversion rate of 1-decene is 50 wt % or more. The oligomer has a kinematic viscosity at 40° C. of 6.0-25 mm2/s and a viscosity index of 160-262.
    Type: Application
    Filed: July 22, 2010
    Publication date: September 13, 2012
    Applicant: PETROCHINA COMPANY LIMITED
    Inventors: Fuling Huang, Puke Mi, Sihan Wang, Jinhua Qian, Qian Chen, Sheng Xu, Jianzhong Li, Gang Wang, Baojun Zhang, Min Liu, Guizhi Wang, Xuemei Han, Jiabo Qu, Panfeng Lu, Shukun Sun, Xiuhui Wang, Yuxin Gao, Deshun Zhang, Ling Jiang, Buwei Yu, Libo Wang, Yali Wang, Lingting Fan, Peng Wei, Wei Liu, Guiyue Guo
  • Patent number: 8258357
    Abstract: This invention relates to an integrated process for the efficient production of olefins from C4 feedstocks comprising butane and more particularly to a method of producing propylene and butadiene. The process combines a dehydrogenation unit with an olefin conversion unit to convert butane feedstock to propylene and butadiene products. The combined catadiene-OCT process produces yields of propylene from normal butane in excess of 70%.
    Type: Grant
    Filed: March 25, 2009
    Date of Patent: September 4, 2012
    Assignee: Lummus Technology Inc.
    Inventors: Kerman Dukandar, David Spence, Sunil Panditrao
  • Patent number: 8258358
    Abstract: A process for the production of propylene, the process including: fractionating a hydrocarbon stream comprising n-butenes, isobutylene, and paraffins into at least two fractions including a light C4 fraction comprising isobutylene and a heavy C4 fraction comprising n-butenes and paraffins; contacting at least a portion of the heavy C4 fraction with a metathesis catalyst to form a metathesis product comprising ethylene, propylene, C4+ olefins, and paraffins; fractionating the metathesis product into at least four fractions including an ethylene fraction, a propylene fraction, a C4 fraction comprising C4 olefins and paraffins, and a C5+ fraction; cracking the light C4 fraction and the C5+ fraction to produce a cracking product comprising ethylene, propylene, and heavier hydrocarbons; and fractionating the cracking product into at least two fractions including a light fraction comprising propylene and a fraction comprising C5 to C6 hydrocarbons.
    Type: Grant
    Filed: January 4, 2012
    Date of Patent: September 4, 2012
    Assignee: Lummus Technology Inc.
    Inventors: Robert J. Gartside, Bala Ramachandran
  • Publication number: 20120203048
    Abstract: A method for manufacturing a catalyst, which comprises regenerating a catalyst comprising a zeolite as an active ingredient and having an ethylene conversion lowered through reaction of producing propylene by bringing into contact with ethylene in a vapor phase, by bringing the catalyst into contact with a gas which does not comprise oxygen and comprises hydrogen having a hydrogen partial pressure of 0.01 MPa or more as an absolute pressure thereof.
    Type: Application
    Filed: February 10, 2012
    Publication date: August 9, 2012
    Applicant: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Mikio HAYASHI, Masahiro HARA, Masashi YAMAGUCHI, Yumiko YOSHIKAWA, Takahiko TAKEWAKI, Tohru SETOYAMA, Naoyuki SAKAMOTO