Patents Assigned to Lyondell Chemical Technology
  • 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: 11827589
    Abstract: Methods of converting isobutylene to C5+ compounds. The methods may include contacting isobutylene with a skeletal isomerization catalyst to provide a mixture of C4 olefins, and then contacting the mixture of C4 olefins with a metathesis catalyst to convert the mixture of C4 olefins to a product mixture. The product mixture may include C5+ olefins.
    Type: Grant
    Filed: September 23, 2022
    Date of Patent: November 28, 2023
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Linn Fang, Daniel F. White, Lei Zhang
  • Patent number: 11806701
    Abstract: Methods for preparing molybdenum-based catalyst for epoxidation reactions using MPG sourced from a propylene oxide/styrene monomer (POSM) production process are described. Streams exiting from the POSM reactor are combined and separated to isolate an aqueous-based, MPG-containing purge stream from other recoverable byproducts of the POSM process. This MPG-containing purge stream is then used as is in the catalyst preparation of molybdenum-based catalyst for epoxidation. Alternatively, the MPG-containing purge stream can undergo additional purification treatments before being utilized in the catalyst preparation.
    Type: Grant
    Filed: June 25, 2021
    Date of Patent: November 7, 2023
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Ha H. Nguyen, Anthony S. Dearth, Harold V. Larson
  • Publication number: 20230339832
    Abstract: A method for removing metal salts from alkylaromatic oxidate streams used for alkene oxide production, or used in the co-production of propylene oxide and styrene monomer (“POSM”), and methods for caustic washing of oxidate streams formed in these processes. The concentration of metal salts carried over from a caustic washing may be reduced by washing the organic phase resulting from the caustic wash with water in the presence of carbon dioxide (CO2). The CO2 may be provided in any form, such as gaseous CO2, dry ice, carbonated water, supercritical (liquid) CO2, or any other suitable form.
    Type: Application
    Filed: April 20, 2023
    Publication date: October 26, 2023
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: David W. Leyshon, Sandor Nagy, Elizabeth I. Ross-Medgaarden
  • Publication number: 20230107520
    Abstract: Methods of converting isobutylene to C5+ compounds. The methods may include contacting isobutylene with a skeletal isomerization catalyst to provide a mixture of C4 olefins, and then contacting the mixture of C4 olefins with a metathesis catalyst to convert the mixture of C4 olefins to a product mixture. The product mixture may include C5+ olefins.
    Type: Application
    Filed: September 23, 2022
    Publication date: April 6, 2023
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Linn Fang, Daniel F. White, Lei Zhang
  • Publication number: 20230105219
    Abstract: Methods and systems for removing or reducing water and producing epoxide. The methods may include providing a first mixture that includes t-butyl hydroperoxide, t-butyl alcohol, and a first amount of water; and contacting at least a portion of the first mixture with a membrane to reduce the amount of water in the first mixture.
    Type: Application
    Filed: October 3, 2022
    Publication date: April 6, 2023
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Ha H. Nguyen, Xueyong Yang
  • Patent number: 11613510
    Abstract: A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of methylcyclohexane as a reaction solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted diphosphine ligand. The use of the methylcyclohexane increases the reaction rate while also giving a high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde and improving the separation of the hydroxyaldehyde products from the catalyst system.
    Type: Grant
    Filed: April 7, 2022
    Date of Patent: March 28, 2023
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Beaven S. Mandimutsira, Robert J. Rebman
  • Patent number: 11590477
    Abstract: Methods of preparing titanated silica catalysts, and titanated silica catalysts. The titanated silica catalysts may include a silica support, which may include spherical beads. Methods of olefin epoxidation, which may include contacting an olefin with a titanated silica catalyst in the presence of an oxidant.
    Type: Grant
    Filed: November 2, 2020
    Date of Patent: February 28, 2023
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Sandor Nagy, Nicholas Bruschi, Elizabeth I. Ross-Medgaarden, David W. Leyshon, Barbara Kimmich
  • Publication number: 20220401934
    Abstract: A skeletal isomerization process for isomerizing olefins is described. The process utilizes added hydrogen as a diluent to extend the isomerization catalyst's lifetime and increase the yield of skeletal isomer products compared to process that utilize inert gas diluents. The methods of this disclosure can be applied to feeds containing iso-olefins (for the production of linear olefins) or linear olefins (for the production of iso-olefins).
    Type: Application
    Filed: June 3, 2022
    Publication date: December 22, 2022
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Rick B. Watson, David W. Leyshon, Kevin P. Fogarty
  • Publication number: 20220396481
    Abstract: Disclosed herein are hydrogen peroxide solutions in non-aqueous solvents and processes for manufacturing the non-aqueous hydrogen peroxide solutions starting from an aqueous hydrogen peroxide solution. Exemplary non-aqueous solvents include alcohols such as tert-butyl alcohol. It has been discovered that when tert-butyl alcohol and an aqueous hydrogen peroxide solution are combined in certain ratios, and water from this mixture is removed by an azeotropic distillation, tert-butyl alcohol-based hydrogen peroxide solution comprising less than 1 wt % water are readily achieved.
    Type: Application
    Filed: June 2, 2022
    Publication date: December 15, 2022
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Ha H. Nguyen, Randy Magadan
  • Publication number: 20220324782
    Abstract: A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of methylcyclohexane as a reaction solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted diphosphine ligand. The use of the methylcyclohexane increases the reaction rate while also giving a high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde and improving the separation of the hydroxyaldehyde products from the catalyst system.
    Type: Application
    Filed: April 7, 2022
    Publication date: October 13, 2022
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Beaven S. Mandimutsira, Robert J. Rebman
  • Patent number: 11440858
    Abstract: A skeletal isomerization process for isomerizing olefins is described. The process includes the steps of feeding an olefin-containing feed to a reactor at a space velocity of 1-100 hr?1 for a first period of time at a first temperature, followed by discontinuing, or stopping, the olefin-containing feed for a second period of time while maintaining the reactor at a second temperature, before resuming the flow of the olefin-containing feed for a third period of time. The methods of this disclosure increase the yield of the skeletal isomers product while reducing the production of C5+ heavy olefins. Additionally, the methods of this disclosure can be applied to feeds containing iso-olefins (for the production of linear olefins) or linear olefins (for the production of iso-olefins).
    Type: Grant
    Filed: November 5, 2021
    Date of Patent: September 13, 2022
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Rick B. Watson, David W. Leyshon
  • Patent number: 11370726
    Abstract: Methods of improving the selectivity of selective hydrogenation of residual 1,3-butadiene in a C4 fraction of a hydrocarbon raffinate stream in a fixed-bed reactor are described. The methods may include co-feeding a competitive chemical species that increases the mechanistic selectivity to 1- and 2-butenes while increasing isomerization selectivity to 2-butene in the product stream. The hydrogenation reactor and competitive chemical species conditions may be tailored to selectively produce butenes over butane or iso-butane, where the butenes comprise 1-butene and/or 2-butene.
    Type: Grant
    Filed: April 27, 2020
    Date of Patent: June 28, 2022
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Sarthak Gaur, Daniel F. White
  • Patent number: 11370737
    Abstract: A process of co-feeding gaseous ethylene with liquid allyl alcohol in the presence of a catalyst to produce 1,4-butanediol and n-propanol may include: introducing a gaseous mixture of ethylene, carbon monoxide and hydrogen into a reactor in the presence of a hydroformylation catalyst in a solvent; introducing liquid allyl alcohol (AA) into the reactor; and carrying out hydroformylation reaction at a temperature between 50 and 100° C. to obtain hydroformylation products.
    Type: Grant
    Filed: September 21, 2021
    Date of Patent: June 28, 2022
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Beaven S. Mandimutsira, Roberto Alvarez
  • Patent number: 11358920
    Abstract: A process of producing allyl alcohol by reacting glycerin with ReO3—Al2O3 in the presence of gamma-valerolactone (GVL) in a reactor is described. More specifically, a process to produce allyl alcohol, comprising the step of: a) reacting glycerin with ReO3—Al2O3 in the presence of an inert solvent, GVL, in a reactor, and b) collecting the product comprising allyl alcohol.
    Type: Grant
    Filed: July 30, 2021
    Date of Patent: June 14, 2022
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Xueyong Yang, Daniel F. White, Chelsee A. Arceneaux, Pranit S. Metkar
  • Publication number: 20220135500
    Abstract: A skeletal isomerization process for isomerizing olefins is described. The process includes the steps of feeding an olefin-containing feed to a reactor at a space velocity of 1-100 hr?1 for a first period of time at a first temperature, followed by discontinuing, or stopping, the olefin-containing feed for a second period of time while maintaining the reactor at a second temperature, before resuming the flow of the olefin-containing feed for a third period of time. The methods of this disclosure increase the yield of the skeletal isomers product while reducing the production of C5+ heavy olefins. Additionally, the methods of this disclosure can be applied to feeds containing iso-olefins (for the production of linear olefins) or linear olefins (for the production of iso-olefins).
    Type: Application
    Filed: November 5, 2021
    Publication date: May 5, 2022
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Rick B. Watson, David W. Leyshon
  • Publication number: 20220135499
    Abstract: A skeletal isomerization process for isomerizing olefins is described. The process includes the steps of feeding an olefin-containing feed to a reactor having an isomerization catalyst with a small crystalline size that is less than 1 ?m in all directions. The small crystalline size increases the life of the catalyst and the yield of skeletal isomer products, as well as reducing the formation of heavy C5+ olefin byproducts, as compared to processes using conventional catalyst with crystalline sizes of 1 ?m or more.
    Type: Application
    Filed: November 5, 2021
    Publication date: May 5, 2022
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Rick B. Watson, David W. Leyshon
  • Publication number: 20220098138
    Abstract: A process of co-feeding gaseous ethylene with liquid allyl alcohol in the presence of a catalyst to produce 1,4-butanediol and n-propanol may include: introducing a gaseous mixture of ethylene, carbon monoxide and hydrogen into a reactor in the presence of a hydroformylation catalyst in a solvent; introducing liquid allyl alcohol (AA) into the reactor; and carrying out hydroformylation reaction at a temperature between 50 and 100° C. to obtain hydroformylation products.
    Type: Application
    Filed: September 21, 2021
    Publication date: March 31, 2022
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Daniel F. White, Beaven S. Mandimutsira, Roberto Alvarez
  • Publication number: 20220081376
    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: Application
    Filed: September 14, 2021
    Publication date: March 17, 2022
    Applicant: Lyondell Chemical Technology, L.P.
    Inventors: Lei Zhang, Pranit S. Metkar, Majid Keyvani, Daniel F. White
  • Patent number: 11261142
    Abstract: Improved systems and methods for producing propylene from olefins including isobutylene is disclosed. The improvements combine streams containing co-produced 1-butene, 2-butene, butadiene, and heavy olefins (C5+) exiting both a metathesis reactor and a skeletal isomerization reactor in a gasoline fractionation tower to remove the heavy olefins. The C4-containing distillate from the gasoline fractionation tower is then fed to a hydroisomerization unit to form mono-olefins and 2-butene. The resulting 2-butene rich stream can then be utilized in metathesis reactions to increase the production of propylene while increasing the lifetime of the metathesis catalyst.
    Type: Grant
    Filed: June 28, 2021
    Date of Patent: March 1, 2022
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: David W. Leyshon, Rick B. Watson