Abstract: A process comprising a heterogenous reaction between a solid metal organic framework supported heteropolyacid catalyst and a hydrocarbon feed to form a modified hydrocarbon stream. The modified hydrocarbon stream comprises essentially of C6+ hydrocarbons.
Type:
Grant
Filed:
October 13, 2021
Date of Patent:
May 9, 2023
Assignee:
Phillips 66 Company
Inventors:
Camille Malonzo May, Jose Edgar Mendez-Arroyo, Jianhua Yao
Abstract: A process for producing high octane bio-based alkylate is provided. The process involves reacting isobutane and bio-ethylene using an ionic liquid catalyst. Reaction conditions can be chosen to assist in attaining, or to optimize, desirable alkylate yields and/or properties.
Type:
Grant
Filed:
September 28, 2022
Date of Patent:
May 9, 2023
Assignee:
CHEVRON U.S.A. INC.
Inventors:
Bong-Kyu Chang, Hye-Kyung Cho Timken, Michelle K. Young, Cong-Yan Chen, Stephen Joseph Miller
Abstract: This disclosure provides improved processes for converting benzene/toluene via methylation with methanol/dimethyl ether for producing, e.g., p-xylene. In an embodiment, a process comprises contacting a methylation agent feed with an aromatic hydrocarbon feed in the presence of a methylation catalyst in a methylation reactor at increased pressure. Reduced methylation catalyst deactivation can be achieved with increased pressure in the methylation reactor.
Type:
Grant
Filed:
March 18, 2020
Date of Patent:
May 9, 2023
Assignee:
ExxonMobil Chemical Patents Inc.
Inventors:
Seth M. Washburn, Hsu Chiang, Tan-Jen Chen
Abstract: An alkylation process is described. The process involves alkylation of isobutane and ethylene in a loop reactor using an ionic liquid catalyst as a continuous phase. The alkylate typically has a research octane number of at least about 93, and the olefin conversion is typically at least about 95%.
Type:
Grant
Filed:
September 28, 2022
Date of Patent:
May 9, 2023
Assignee:
CHEVRON U.S.A. INC.
Inventors:
Huping Luo, Hye-Kyung Cho Timken, Bong-Kyu Chang
Abstract: Removal of solids accumulations that are attached to an inlet tube sheet of a heat exchanger in a hydrogenation reactor system by injecting a flush liquid through an injection port on the heat exchanger. Injecting the flush liquid removes portions of the solids accumulations.
Abstract: Catalyst systems for tetramerizing ethylene to form 1-octene may include a catalyst which may include a chromium compound coordinated with a ligand and a co-catalyst which may include an organoaluminum compound. The ligand may have a chemical structure according to Chemical Structure (I), wherein R5 is a (C1-C15) alkyl group, a (C3-C15) cyclohydrocarbyl group, a (C3-C15) cycloheterohydrocarbyl group, or a (C1-C15) aryl group, and RA, RB, RC, RD, RE, RF, RG, RH, R1, R2, R3, R4, R6, R7, R8, and R9 are independently chosen from a hydrogen atom, a (C1-C50) hydrocarbyl group, or a (C1-C50) heterohydrocarbyl group.
Type:
Grant
Filed:
August 31, 2022
Date of Patent:
May 2, 2023
Assignees:
Saudi Arabian Oil Company, King Fahd University of Petroleum and Minerals
Inventors:
E A Jaseer, Samir Barman, Nestor Garcia Villalta, Motaz Khawaji, Wei Xu, Fahad Almalki
Abstract: A process for sulfuric acid catalyzed alkylation involving the use of surfactants which form bi-continuous micro-emulsions with the sulfuric acid and the hydrocarbon is described. The bi-continuous phase facilitates and improves the sulfuric acid catalyzed alkylation reactions. The concentration of the surfactant is selected based on the type of olefin feed. Easy to alkylate feeds, such as 2-butene, use lower concentrations of surfactant, while feeds which are harder to alkylate, such as propene or isobutene, use higher concentrations of the surfactant. In addition, increasing the concentration of sulfuric acid when a surfactant is included resulted in higher calculated RON. The use of a surfactant and a high concentration of sulfuric acid can provide a calculated RON over 100 and close to theoretical yields.
Type:
Grant
Filed:
September 9, 2021
Date of Patent:
May 2, 2023
Assignee:
UOP LLC
Inventors:
Christopher P. Nicholas, Susie C. Martins, David E. Mackowiak, Hayim Abrevaya, Joel T. Walenga
Abstract: Disclosed herein are processes and reaction systems for controlling a temperature of an oligomerization reaction zone using a heat exchange system.
Abstract: A fuel production plant includes an electrolysis apparatus; an ethanol generation apparatus that decomposes sugars to generate ethanol and carbon dioxide; and a hydrocarbon generation apparatus that generates hydrocarbons by reacting carbon dioxide with hydrogen. The fuel production plant further includes a hydrogen supply part that supplies hydrogen generated in the electrolysis apparatus to the hydrocarbon generation apparatus by coupling the electrolysis apparatus to the hydrocarbon generation apparatus, an oxygen supply part that supplies oxygen generated in the electrolysis apparatus to the ethanol generation apparatus by coupling the electrolysis apparatus to the ethanol generation apparatus, and a carbon dioxide supply part that supplies carbon dioxide generated in the ethanol generation apparatus to the hydrocarbon generation apparatus by coupling the ethanol generation apparatus to the hydrocarbon generation apparatus.
Abstract: The invention relates to oligomerization of olefins, such as ethylene, to higher olefins, such as a mixture of 1-hexene and 1-octene, using a catalyst system that comprises a) a source of chromium b) one or more activators and c) a phosphacycle-containing ligating compound. Additionally, the invention relates to a phosphacycle-containing ligating compound and a process for making said compound.
Type:
Grant
Filed:
February 11, 2022
Date of Patent:
April 11, 2023
Assignee:
Dow Global Technologies LLC
Inventors:
Jerzy Klosin, Kara A. Milbrandt, Scott D. Boelter, David R. Wilson, Mari S. Rosen, Dean M. Welsh, Peter M. Margl, Kyoung Moo Koh, David M. Pearson, Rafael Huacuja
Abstract: Catalyst systems for tetramerizing ethylene to form 1-octene may include a catalyst which may include a chromium compound coordinated with a ligand and a co-catalyst which may include an organoaluminum compound. The ligand may have a chemical structure according to Chemical Structure (I), wherein R5, R6, and R7 are each independently chosen from a (C1-C50) hydrocarbyl group or a (C1-C50) heterohydrocarbyl group, and wherein the (C1-C50) hydrocarbyl or (C1-C50) heterohydrocarbyl groups of R5, R6, and R7 have greater than 10 carbon atoms combined and RA, RB, RC, and RD and R1, R2, R3, and R4, are independently chosen from a hydrogen atom or a (C1-C50) hydrocarbyl group.
Type:
Grant
Filed:
August 31, 2022
Date of Patent:
April 11, 2023
Assignees:
Saudi Arabian Oil Company, King Fahd University of Petroleum and Minerals
Abstract: A method is disclosed of producing hydrocarbons from a recycled or renewable organic material, wherein the recycled or renewable organic material contains from 5 to 30 wt-% oxygen as organic oxy-gen compounds and from 1 to 1000 ppm phosphorous as phosphorous compounds.
Abstract: Provided herein is an alkane dehydrogenation catalyst, a method of manufacturing an alkane dehydrogenation catalyst, and a method of converting alkanes to alkenes.
Type:
Grant
Filed:
March 10, 2021
Date of Patent:
April 11, 2023
Assignees:
UCHICAGO ARGONNE, LLC, FORGE NANO
Inventors:
Christopher L. Marshall, Zheng Lu, Jeffrey W. Elam, Christopher Nicholas, Paul T. Barger, Martha Leigh Abrams, Arrelaine Dameron, Ryon W. Tracy
Abstract: A process and system for the conversion of a feedstock comprising C3-C5 light alkanes to a C5+ hydrocarbon product, for example, a BTX-rich hydrocarbon product, by performing the alkane activation (first-stage) and the oligomerization/aromatization (second-stage) in separate stages, which allows each conversion process to occur at optimal reaction conditions thus increasing the overall hydrocarbon product yield. The alkane activation or first-stage is operated at a higher temperature than the second-stage since light alkanes are much less reactive than light olefins. Since aromatization of olefins is more efficient at higher pressure, the second-stage is maintained at a higher pressure than the first-stage. Further, fixed-bed catalysts are used in each of the first-stage and the second-stage.
Type:
Grant
Filed:
October 21, 2020
Date of Patent:
March 7, 2023
Assignee:
Phillips 66 Company
Inventors:
Jianhua Yao, Hong Xie, Jonathan Marda, Dhananjay Ghonasgi, Sourabh Pansare
Abstract: The present disclosure relates to a catalyst system comprising i) (a) a bicyclic 2-[(phosphinyl)aminyl] cyclic imine chromium salt or (b) a chromium salt and a bicyclic 2-[(phosphinyl)aminyl] cyclic imine and ii) an organoaluminum compound. The present disclosure also relate to a process comprising: a) contacting i) ethylene; ii) a catalyst system comprising (a) a 2-[(phosphinyl)aminyl] cyclic imine chromium salt complex or (b) a chromium salt and a bicyclic 2-[(phosphinyl)aminyl] cyclic imine; ii) an organoaluminum compound, and iii) optionally an organic reaction medium; and b) forming an oligomer product in a reaction zone.
Type:
Grant
Filed:
November 8, 2021
Date of Patent:
February 21, 2023
Assignee:
Chevron Phillips Chemical Company, LP
Inventors:
Steven M. Bischof, Orson L. Sydora, Daniel H. Ess, Uriah J. Kilgore, Doo-Hyun Kwon
Abstract: Systems and processes for dehydrogenating one or more alkanes using electrically heated dehydrogenation reactors. The source of electric energy or power can be a power grid, solar panel, windmill, hydropower, nuclear power, fuel cell, gas turbines, steam turbines, portable generator or the like. The systems and processes provided herein result in a simpler dehydrogenation process which is particularly beneficial at a small scale and at remote locations, including the well site.
Type:
Grant
Filed:
June 21, 2021
Date of Patent:
February 14, 2023
Assignee:
PURDUE RESEARCH FOUNDATION
Inventors:
Rakesh Agrawal, Zewei Chen, Peter Oladipupo
Abstract: The present invention pertains to a method for recovering a selective homogeneous hydrogenation catalyst and a method for reusing the recovered selective homogeneous hydrogenation catalyst. The method for recovering a selective homogeneous hydrogenation catalyst comprises: a step for synthesizing cyclododecene by selectively hydrogenating a first reaction solution containing cyclododecatriene, triphenylphosphine, formaldehyde, and ruthenium chloride, wherein a selective homogeneous hydrogenation catalyst is prepared during the selective hydrogenation reaction from the triphenylphosphine, formaldehyde, and ruthenium chloride to synthesize the cyclododecene; and a step for distilling and separating unreacted cyclododecatriene and cyclododecadiene, as well as the product cyclododecene, from a second reaction solution in which the cyclododecene synthesis has been completed, and recovering the selective homogeneous hydrogenation catalyst.
Abstract: Methods for determining ethylene concentration in an ethylene oligomerization reactor using an ultrasonic flow meter are described, and these methods are integrated into ethylene oligomerization processes and related oligomerization reactor systems.
Type:
Grant
Filed:
September 9, 2021
Date of Patent:
February 7, 2023
Assignee:
Chevron Phillips Chemical Company, LP
Inventors:
Bruce E. Kreischer, Kendall M. Hurst, Eric D. Schwerdtfeger, Steven M. Bischof, Jared Fern, Kent E. Mitchell, James Hillier
Abstract: The present invention relates to a process for the dimerization of alkenes comprising (1) providing a gas stream comprising one or more alkenes; and (2) contacting the gas stream provided in (1) with a catalyst for obtaining a mixture M1 comprising one or more dimerization products of the one or more alkenes, wherein the catalyst in (2) comprises a zeolitic material having a framework structure type selected from the group consisting of MOR, BEA, FER, MFI, TON, FAU, and mixtures of two or more thereof, wherein the framework structure of the zeolitic material comprises YO2, wherein Y stands for one or more tetravalent elements.
Type:
Grant
Filed:
January 30, 2020
Date of Patent:
February 7, 2023
Assignee:
BASF SE
Inventors:
Trees Maria De Baerdemaeker, Andrei-Nicolae Parvulescu, Ivana Jevtovikj, Craig Jon Cain-Borgman, Ulrich Mueller, Andreas Kuschel