Patents by Inventor Charles J. HARLAN

Charles J. HARLAN has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Publication number: 20240092947
    Abstract: The present disclosure relates to supported catalyst systems for olefin polymerization, catalyst system precursors, methods of producing the precursors and catalyst systems and polyolefins formed from the catalyst systems.
    Type: Application
    Filed: November 17, 2021
    Publication date: March 21, 2024
    Inventors: Lubin LUO, Francis C. RIX, Kevin A. Stevens, Chi-l KUO, Xiaodan ZHANG, Jacqueline A. LOVELL, Charles J. HARLAN, Xuan YE, Brian R. BERG
  • Publication number: 20240018278
    Abstract: The present disclosure relates to processes for forming alumoxanes and catalyst systems thereof for olefin polymerization. In at least one embodiment, a process includes forming a solution by, in an aliphatic hydrocarbon having a boiling point of less than about 70 degrees Celsius, introducing at least one hydrocarbyl aluminum with at least one non-hydrolytic oxygen-containing compound and a support material. The molar ratio of aluminum to non-hydrolytic oxygen in the solution is greater than or equal to 1.5, and the combining is conducted at a temperature of less than about 70 degrees Celsius. The process includes distilling the solution at a pressure of greater than about 0.5 atm to form a supported alumoxane precursor. The process further includes heating the supported alumoxane precursor to a temperature greater than the boiling point of the aliphatic hydrocarbon fluid and less than about 160 degrees Celsius to form a supported alumoxane.
    Type: Application
    Filed: November 17, 2021
    Publication date: January 18, 2024
    Inventors: Francis C. RIX, Charles J. HARLAN, KyKA LE, Xiaodan ZHANG
  • Publication number: 20240010660
    Abstract: The present disclosure relates to a precursor for making an activator in a catalyst system for olefin polymerization and methods of producing the precursor, the catalyst system, and the polyolefin. In at least one embodiment, an alumoxane precursor includes (i) the reaction product of at least one non-hydrolytic oxygen-containing compound and at least one hydrocarbyl aluminum; and (ii) an aliphatic hydrocarbon fluid. The reaction product can be identified by first set of signals in an 1HNMR spectrum in a region from about 4.5 ppm to about 5.1 ppm and a second set of signals in a region from about 5.1 ppm to about 6.5 ppm. The ratio of the first to the second set of signals is greater than or equal to about 2.8. The alumoxane precursor is easy to store and ship compared to MAO, which is an intermediate product in conventional methods for forming supported alumoxane.
    Type: Application
    Filed: November 17, 2021
    Publication date: January 11, 2024
    Inventors: Francis C. RIX, Ky KA LE, Charles J. HARLAN
  • Publication number: 20230416418
    Abstract: The present disclosure provides aromatic-solvent-free supported catalyst compounds and catalyst systems comprising asymmetric bridged metallocenes containing a ligand having at least one saturated ring, catalyst systems including such compounds, and uses thereof. These supported catalyst compounds and catalyst systems can be used to prepare polymer comprising no aromatic solvent.
    Type: Application
    Filed: November 17, 2021
    Publication date: December 28, 2023
    Applicant: EXXONMOBIL CHEMICAL PATENTS INC.
    Inventors: Nikola S. LAMBIC, Francis C. RIX, Lubin LUO, Charles J. HARLAN, An Ngoc-Michael NGUYEN
  • Publication number: 20230406868
    Abstract: A method including: preparing an alumoxane precursor from an organic oxygen source, a hydrocarbyl aluminum, and an organic solvent; heating the alumoxane precursor to form an alumoxane suspension; removing solid methylaluminoxane from the alumoxane suspension by filtering the alumoxane suspension to form a filtered solution; and combining the filtered solution with a support to form a supported alumoxane precursor.
    Type: Application
    Filed: November 17, 2021
    Publication date: December 21, 2023
    Inventors: Francis C. RIX, KY KA LE, Charles J. HARLAN
  • Publication number: 20230322972
    Abstract: This invention relates to a supported catalyst system comprising: (i) at least one first catalyst component comprising a group 4 metallocycle containing metallocene complex; (ii) at least one second catalyst component comprising a 2,6-bis(imino)pyridyl iron complex; (iii) activator; and (iv) support. The catalyst system may be used for preparing polyolefins, such a bimodal polyethylene, typically in a gas phase polymerization.
    Type: Application
    Filed: September 29, 2021
    Publication date: October 12, 2023
    Inventors: Matthew W. HOLTCAMP, Laughlin G. MCCULLOUGH, Kevin A. STEVENS, Dongming LI, Robert L. HALBACH, Ramyaa MATHIALAGAN, Charles J. HARLAN, Timothy M. BOLLER
  • Patent number: 11739169
    Abstract: It has become desirable to limit or exclude aromatic solvents, such as toluene, from polymerization reactions. For polymerization reactions employing a non-metallocene transition metal complex as a precursor to a polymerization catalyst, exclusion of aromatic solvents may be difficult due to the limited solubility of such complexes in aliphatic hydrocarbon solvents. Aliphatic hydrocarbon solutions suitable for conducting olefin polymerization reactions, particularly solution polymerization reactions, may comprise: a non-metallocene transition metal complex dissolved in an aliphatic hydrocarbon solvent at a concentration ranging from about 2 mM to about 20 mM at 25° C. in the presence of an organoaluminum compound. A molar ratio of aluminum of the organoaluminum compound to transition metal of the transition metal complex is about 1:1 or greater, and the organoaluminum compound comprises at least about 8 carbons per aluminum.
    Type: Grant
    Filed: April 9, 2021
    Date of Patent: August 29, 2023
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: John R. Hagadorn, Peijun Jiang, Francis C. Rix, Charles J. Harlan, Jo Ann M. Canich
  • Patent number: 11591417
    Abstract: Provided herein are methods and systems for at least partially deactivating at least one component of a reactor effluent from gas phase polyolefin polymerization processes utilizing at least one glycol.
    Type: Grant
    Filed: October 26, 2018
    Date of Patent: February 28, 2023
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Chi-I Kuo, Bruce J. Savatsky, Micah A. McClure, Kevin M. Ferreira, Charles J. Harlan, Valerie H. Markham
  • Publication number: 20230002514
    Abstract: Non-coordinating borate activators deposited upon a support material may be effective for promoting olefin polymerization in the presence of a suitable transition metal complex, particularly for gas phase and slurry polymerization reactions. The non-coordinating borate activators may be deposited upon the support material using substantially aliphatic hydrocarbon solvents, preferably in the absence of aromatic solvents, such as toluene.
    Type: Application
    Filed: August 4, 2020
    Publication date: January 5, 2023
    Inventors: Charles J. Harlan, Margaret T. Whalley, Catherine A. Faler, John R. Hagadorn
  • Publication number: 20220275015
    Abstract: The present disclosure provides metallocene catalyst compounds including at least one —Si— containing linker, catalyst systems including such compounds, and uses thereof. Catalyst compounds of the present disclosure can be hafnium-containing compounds having one or more cyclopentadiene ligand(s) substituted with one or more silyl neopentyl groups and linked with at least one —Si-containing linker. In another class of embodiments, the present disclosure is directed to polymerization processes to produce polyolefin polymers from catalyst systems including one or more olefin polymerization catalysts, at least one activator, and an optional support.
    Type: Application
    Filed: July 28, 2020
    Publication date: September 1, 2022
    Inventors: Matthew W. Holtcamp, Charles J. Harlan, Subramaniam Kuppuswamy, Matthew S. Bedoya
  • Patent number: 11279723
    Abstract: A process to synthesize a Group 4 ansa-metallocene. The process includes reacting an alkaline earth metal dianion dicyclopentadiene ligand-Lewis base complex with a Group 4 metal tetrahalide in the presence of an alkali metal halide, and forming the Group 4 ansa-metallocene dihalide with high yield and purity.
    Type: Grant
    Filed: June 20, 2019
    Date of Patent: March 22, 2022
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Charles J. Harlan, Matthew W. Holtcamp, Subramaniam Kuppuswamy, Steven C. Haas
  • Publication number: 20220056168
    Abstract: The present disclosure provides processes for polymerizing olefin(s). Methods can include combining a catalyst component slurry with a catalyst component solution to form a third catalyst composition and introducing the third composition into a polymerization reactor. The present disclosure further provides methods for preparing catalyst component slurries, catalyst component solutions, and the third catalyst compositions. In at least one embodiment, a method includes contacting a first composition and a second composition in a line to form a third composition, the first composition including a contact product of a first catalyst, a second catalyst, a support, an activator, a mineral oil, and a wax, and the second composition comprising a contact product of an activator, a diluent, and the first catalyst or second catalyst.
    Type: Application
    Filed: October 30, 2019
    Publication date: February 24, 2022
    Inventors: Joshua P. Olson, Chi-l Kuo, Charles J. Harlan, Kevin A. Stevens, Justin A. Federici
  • Publication number: 20220033535
    Abstract: The present disclosure provides processes for polymerizing olefin(s). In at least one embodiment, a method for producing a polyolefin is provided. The method includes contacting a first composition and a second composition in a line to form a third composition. The first composition includes a contact product of a first catalyst, a second catalyst, a support, a first activator, and a diluent, and the mol ratio of first catalyst to second catalyst is from 90:10 to 40:60. The second composition includes a contact product of the second catalyst, a second activator, and a second diluent. The third composition includes a mol ratio of first catalyst to second catalyst of from 89:11 to 10:90. The method includes introducing the third composition from the line into a gas-phase fluidized bed reactor, exposing the third composition to polymerization conditions, and obtaining a polyolefin.
    Type: Application
    Filed: October 30, 2019
    Publication date: February 3, 2022
    Inventors: Kevin A. Stevens, David F. Sanders, Matthew W. Holtcamp, Charles J. Harlan, Xuan Ye, Adriana S. Silva, Matthew S. Bedoya, Joshua P. Olson
  • Publication number: 20220033537
    Abstract: In an embodiment, a method for producing a polyolefin includes contacting a first composition and a second composition in in a line to form a third composition, wherein: the first composition comprises a contact product of a first catalyst, a second catalyst, a support, a first activator, and a diluent, wherein the mol ratio of second catalyst to first catalyst is from 60:40 to 40:60, the second composition comprises a contact product of the third catalyst, a second activator, and a second diluent, and the third composition comprises a mol ratio of the third catalyst to the second catalyst to the first catalyst of from 10:35:55 to 60:15:25, such as 30:20:30; introducing the third composition from the line into a gas-phase fluidized bed reactor; exposing the third composition to polymerization conditions; and obtaining a polyolefin.
    Type: Application
    Filed: October 30, 2019
    Publication date: February 3, 2022
    Inventors: Kevin A. Stevens, David F. Sanders, Matthew W. Holtcamp, Charles J. Harlan, Xuan Ye, Adriana S. Silva, Matthew S. Bedoya, Joshua P. Olson
  • Publication number: 20220033536
    Abstract: In an embodiment, a method for producing a polyolefin is provided. The method includes: contacting a first composition and a second composition in a line to form a third composition, wherein: the first composition comprises a contact product of a first catalyst, a second catalyst, a support, and a diluent, wherein the mol ratio of second catalyst to first catalyst is from 60:40 to 40:60, the second composition comprises a contact product of the second catalyst and a second diluent; introducing the third composition from the line into a gas-phase fluidized bed reactor; exposing the third composition to polymerization conditions; and obtaining a polyolefin.
    Type: Application
    Filed: October 30, 2019
    Publication date: February 3, 2022
    Inventors: Kevin A. Stevens, David F. Sanders, Matthew W. Holtcamp, Charles J. Harlan, Xuan Ye, Adriana S. Silva, Matthew S. Bedoya, Joshua P. Olson
  • Patent number: 11225539
    Abstract: This invention relates to supported catalyst compositions of transition metal complexes of a dianionic, tridentate ligand that features a central neutral heterocyclic Lewis base and two phenolate donors, where the tridentate ligand coordinates to the metal center to form two eight-membered rings. Preferably the bis(phenolate) complexes are represented by Formula (I): where M, L, X, m, n, E, E?, Q, R1, R2, R3, R4, R1?, R2?, R3?, R4?, A1, A1?, A3A2, and A2?A3? are as defined herein, where A1QA1? are part of a heterocyclic Lewis base containing 4 to 40 non-hydrogen atoms that links A2 to A2? via a 3-atom bridge with Q being the central atom of the 3-atom bridge.
    Type: Grant
    Filed: February 11, 2020
    Date of Patent: January 18, 2022
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Charles J. Harlan, Nikola S. Lambic, John R. Hagadorn, Jo Ann M. Canich
  • Patent number: 11186601
    Abstract: This invention relates to metallocene compounds represented by the formula: catalyst systems comprising said metallocene compound and an activator or a reaction product of the metallocene compound with the at least one activator, and polymerization processes using such metallocene compounds and activators, where Cpa and Cpb are optionally-substituted cyclopentadienyl rings; A is bridging group; q is zero or 1; Q is O, O(CR3R4)m, (CR3R4)mO, or (CR3R4)m; m is 0 to 18; Z is (CR3R4)2; LA is a Lewis acid; M is a transition metal; X1 and X2 are independently R5 or OR5; R1 and R2 are independently selected from optionally-substituted hydrocarbyl groups; R3 and R4 are independently selected from the group consisting of H, halogen, and an optionally-substituted hydrocarbyl group; and R5 is alkyl, aryl, perfluoroalkyl, or perfluoroaryl.
    Type: Grant
    Filed: August 27, 2019
    Date of Patent: November 30, 2021
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Matthew W. Holtcamp, Charles J. Harlan, Subramaniam Kuppuswamy, Matthew S. Bedoya, Kevin A. Stevens
  • Patent number: 11161922
    Abstract: The present disclosure provides a method for preparing a catalyst system comprising contacting in an aliphatic solvent at a temperature of from less than 0° C. to ?60° C. at least one support material having absorbed water and at least one hydrocarbyl aluminum compound to form a supported alumoxane (catalyst precursor) and contacting the supported alumoxane with at least one catalyst compound having a Group 3 through Group 12 metal atom or lanthanide metal atom. The supported alumoxane may be heated prior to contact with the catalyst compound.
    Type: Grant
    Filed: September 17, 2018
    Date of Patent: November 2, 2021
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Lubin Luo, Anupriya Jain, Charles J. Harlan
  • Publication number: 20210332164
    Abstract: It has become desirable to limit or exclude aromatic solvents, such as toluene, from polymerization reactions. For polymerization reactions employing a non-metallocene transition metal complex as a precursor to a polymerization catalyst, exclusion of aromatic solvents may be difficult due to the limited solubility of such complexes in aliphatic hydrocarbon solvents. Aliphatic hydrocarbon solutions suitable for conducting olefin polymerization reactions, particularly solution polymerization reactions, may comprise: a non-metallocene transition metal complex dissolved in an aliphatic hydrocarbon solvent at a concentration ranging from about 2 mM to about 20 mM at 25° C. in the presence of an organoaluminum compound. A molar ratio of aluminum of the organoaluminum compound to transition metal of the transition metal complex is about 1:1 or greater, and the organoaluminum compound comprises at least about 8 carbons per aluminum.
    Type: Application
    Filed: April 9, 2021
    Publication date: October 28, 2021
    Inventors: John R. Hagadorn, Peijun Jiang, Francis C. Rix, Charles J. Harlan, Jo Ann M. Canich
  • Patent number: 11142591
    Abstract: A process including contacting one or more monomers, at least one catalyst system, and a condensing agent including ?10 mol % tetramethylsilane under polymerizable conditions to produce a polyolefin polymer is provided.
    Type: Grant
    Filed: September 7, 2017
    Date of Patent: October 12, 2021
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: John R. Hagadorn, Charles J. Harlan, Richard B. Pannell, Chi-I Kuo