Patents Examined by Sikarl A. Witherspoon
  • Patent number: 11198760
    Abstract: A method of producing a polyether polyol that includes reacting a low molecular weight initiator with ethylene oxide in the presence of a polymerization catalyst, the low molecular weight initiator having a number average molecular weight of less than 1,000 g/mol and a nominal hydroxyl functionality at least 2, and the polymerization catalyst being a Lewis acid catalyst having the general formula M(R1)1(R2)1(R3)1(R4)0 or 1. Whereas, M is boron, aluminum, indium, bismuth or erbium, R1, R2, and R3 each includes a same fluoroalkyl-substituted phenyl group, and optional R4 includes a functional group or functional polymer group. R1, R2, and R3 are the same fluoroalkyl-substituted phenyl group. The method further includes forming a polyether polyol having a number average molecular weight of greater than the number average molecular weight of the low molecular weight initiator in the presence of the Lewis acid catalyst.
    Type: Grant
    Filed: September 14, 2018
    Date of Patent: December 14, 2021
    Assignees: Dow Global Technologies LLC, Northwestern University
    Inventors: Arjun Raghuraman, William H. Heath, Sukrit Mukhopadhyay, Heather A. Spinney, David R. Wilson, Justin M. Notestein, SonBinh T. Nguyen
  • Patent number: 11189388
    Abstract: Methods for purifying the molybdenum-99 isotope are disclosed. Molybdenum-99 is loaded onto an anion exchange column and extracted. In some embodiments, the extraction solution may include nitric acid and nitrate salts. In other embodiments, a two stage elution is performed in which a nitric acid containing eluent and a hydroxide containing eluent are used in succession to extract molybdenum-99.
    Type: Grant
    Filed: August 14, 2017
    Date of Patent: November 30, 2021
    Assignee: Curium US LLC
    Inventors: Luis Antonio M. M. Barbosa, Frits Dekker, Marjolijn Gerritsen, Mark David Hermeler
  • Patent number: 11186533
    Abstract: A method for preparing 2,2?,4,4?-Tetrahydroxy-3-(2?-hydroxy-3?-methylbutyl-3?-alkenyl)chalcone includes the following steps: subjecting a Morus alba leaf to extraction with an aqueous solution of methanol or ethanol having a volume fraction of 40%-100%, concentrating an extract to remove methanol or ethanol and dissolving in water, subjecting to extraction with petroleum ether and ethyl acetate successively, and concentrating an ethyl acetate extract to obtain a paste; chromatographing the paste over a silica gel column using chloroform-methanol, collecting an eluate where the volume ratio of chloroform-methanol is 95/5; chromatographing the eluate over a reversed-phase column using methanol-water, collecting an eluate where the volume ratio of methanol-water is 60/40, and thereby the compound is obtained.
    Type: Grant
    Filed: September 21, 2018
    Date of Patent: November 30, 2021
    Assignee: SOUTH CHINA BOTANICAL GARDEN, CHINESE ACADEMY OF SCIENCES
    Inventors: Bao Yang, Yueming Jiang
  • Patent number: 11185852
    Abstract: The present invention relates to a catalyst composition for hydroformylation and a method of preparing an aldehyde using the same. More specifically, the present invention provides a catalyst composition for hydroformylation including a specific phosphite-based ligand and a transition metal compound in a specific amount range, thereby being capable of greatly lowering a use amount of an expensive transition metal compound and exhibiting excellent catalyst activity or stability. In addition, by using the catalyst composition in hydroformylation, excellent reaction efficiency may be provided and iso-aldehyde may be generated in high yield.
    Type: Grant
    Filed: February 2, 2018
    Date of Patent: November 30, 2021
    Assignee: LG CHEM, LTD.
    Inventors: Tae Yun Kim, Min Ji Choi, Sung Shik Eom, Mi Young Kim, Dong Hyun Ko, Da Won Jung
  • Patent number: 11180437
    Abstract: Disclosed is a method for preparing a 1,3-dicarbonyl compound based on a metal hydride/palladium compound system. The method includes the following steps: suspending a palladium compound and a metal hydride in a solvent under the protection of nitrogen, then adding an electron-deficient olefin compound, reacting same at 0° C.-100° C. for 0.3 to 10 hours, then adding a saturated ammonium chloride aqueous solution to stop the reaction, and then subjecting same to extraction, evaporation until dryness, and column chromatography purification to obtain the 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used by the present invention are reagents easily obtained in a laboratory. Compared to a common hydrogen hydrogenation method, the method is easier to operate, and has a higher safety, mild conditions, and a high reaction yield.
    Type: Grant
    Filed: March 16, 2021
    Date of Patent: November 23, 2021
    Assignee: SOOCHOW UNIVERSITY
    Inventors: Shilei Zhang, Yujian Mao
  • Patent number: 11174222
    Abstract: Provided is a process for preparing an organic diisocyanate of the formula: OCN—R—NCO (1), wherein R represents a bivalent hydrocarbon radical containing 3 to 20 carbon atoms, the carbon atoms being arranged in a way that the two nitrogen atoms are separated from each other by at least 3 carbon atoms, the process comprising, Step (I) preparing a diurethane of the formula wherein R is the same as in formula (1), R? and R? independently represent organic radicals selected from the group consisting of 4 to 36 carbon atoms, 4 to 74 hydrogen atoms, 0 to 12 oxygen atoms that have the oxidation state ?2, and 0 to 1 halogen atoms from a diarylurethane of the formula, wherein R is the same as in formula (1), Ar and Ar? independently represent a substituted or unsubstituted aryl or heteroaryl radical selected from the group containing a total of 4 to 20 carbon atoms by transesterification, Step (II) subjecting the diurethane of the formula (2) to a cleavage reaction to form the hydroxy compounds R?—OH and R?—O
    Type: Grant
    Filed: September 12, 2018
    Date of Patent: November 16, 2021
    Assignee: Covestro Deutschland AG
    Inventor: Michael Merkel
  • Patent number: 11173479
    Abstract: Provided herein is a novel process for producing shaped catalyst bodies in which a mixture having aluminum contents of Al±0 in the range from 80 to 99.8% by weight, based on the mixture used, is used to form a specific intermetallic phase, shaped catalyst bodies obtainable by the process of the invention, a process for producing an active catalyst fixed bed including the shaped catalyst bodies provided herein, the active catalyst fixed beds and also the use of these active catalyst fixed beds for the hydrogenation of organic hydrogenatable compounds or for formate degradation.
    Type: Grant
    Filed: September 10, 2018
    Date of Patent: November 16, 2021
    Assignee: BASF SE
    Inventors: Marie Katrin Schroeter, Irene de Wispelaere, Michael Schwarz, Rolf Pinkos, Inna Schwabauer
  • Patent number: 11161870
    Abstract: The subject disclosure is directed to functionalized bile acids, preparation thereof, and usage thereof for therapeutic and material applications. In one embodiment, a method of generating functionalized bile acid materials can comprise directly activating a carboxylic acid of a bile acid compound using a coupling agent comprising an amide or ester compound, thereby generating an intermediate bile acid derivative material. The method can further comprise attaching a functional group material to the intermediate bile acid derivative material by reacting the functional group material and the intermediate bile acid derivative material, thereby generating a functionalized bile acid material.
    Type: Grant
    Filed: February 7, 2020
    Date of Patent: November 2, 2021
    Assignee: INTERNATIONAL BUSINESS MACHINES CORPORATION
    Inventors: James L. Hedrick, Nathaniel H. Park
  • Patent number: 11161796
    Abstract: A method for the production of a fuel additive includes passing a hydrocarbon stream comprising crude mixed C4 hydrocarbons through a first hydrogenation unit to produce a first product stream; passing the first product stream from the first hydrogenation unit to a methyl tert-butyl ether synthesis unit forming methyl tert-butyl ether and a byproduct stream; passing the byproduct stream through a first distillation unit to separate the byproduct stream into a first 1-butene stream, an isobutane stream, and a 2-butene and n-butane stream; forming a second product stream by passing the 2-butene and n-butane stream to a selective conversion unit; passing the second product stream into a second distillation unit to form an n-butane stream and a second 1-butene stream; passing the second 1-butene stream to a fuel additive production unit; and passing the first 1-butene stream to the fuel additive production unit to form the fuel additive.
    Type: Grant
    Filed: September 16, 2019
    Date of Patent: November 2, 2021
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Guillermo Leal, Mohammed Bismillah Ansari, Vijay Dinkar Bodas, Sultan Eid Al-Otaibi, Mohammed A. Al-Ghamdi, Naif Mohammed Al-Naddah Al-Otaibi
  • Patent number: 11155510
    Abstract: A hydroformylation system for making aldehydes includes: (a) a primary reactor provided with catalyst feed, syngas feed and olefin feed adapted to convert the olefin and syngas to product aldehyde; (b) a first liquid vapor separator coupled to the primary reactor for receiving output therefrom, adapted to separate the product aldehyde into a crude aldehyde product stream and a vent stream containing syngas and unreacted olefin; (c) a vent reactor coupled to the first liquid vapor separator to receive the vent stream therefrom, the vent reactor also being coupled to the primary reactor which is configured to provide catalyst thereto, wherein the vent reactor is operative to convert unreacted olefin in the vent stream from the first liquid vapor separator to additional product aldehyde.
    Type: Grant
    Filed: July 6, 2020
    Date of Patent: October 26, 2021
    Assignee: OQ Chemicals Corporation
    Inventors: Kyle J. Zalman, Markus Heuwes, Christopher J. Bischoff
  • Patent number: 11148987
    Abstract: A method of reducing the salt content of a neutralized aralkyl hydroperoxide cleavage mass stream comprising passing the neutralized stream into a vessel, the vessel having an inlet, two outlets, an aqueous layer and a hydrocarbon layer wherein the neutralized stream enters the vessel through a first inlet and a hydrocarbon stream exits the vessel through a first outlet that is in fluid communication with the hydrocarbon layer.
    Type: Grant
    Filed: August 22, 2018
    Date of Patent: October 19, 2021
    Assignee: SHELL OIL COMPANY
    Inventors: Garry Morgan McCauley, Jamie Jerrick Juliette, David Randall Faske, Thomas Robert Porter
  • Patent number: 11149001
    Abstract: A method produces ?-caprolactam through adipamide as an intermediate, and characteristically includes a lactamization step of reacting adipamide, formed from a material compound, with hydrogen and ammonia in the presence of a catalyst containing: a metal oxide mainly containing an oxide(s) of one or more metallic elements selected from the group consisting of metallic elements of group 5 and groups 7 to 14 in the 4th to 6th periods of the periodic table; and a metal and/or a metal compound having a hydrogenation ability.
    Type: Grant
    Filed: December 5, 2017
    Date of Patent: October 19, 2021
    Assignee: TORAY INDUSTRIES, INC.
    Inventors: Daijiro Tsukamoto, Masateru Ito, Katsushige Yamada, Masato Akahira, Daisuke Yamamoto, Koji Yamauchi
  • Patent number: 11148986
    Abstract: A method for extracting polyol from a fermentation process is disclosed. The preparing method includes rectifying and purifying PDO (1,3-propanediol) from a polyol fermentation broth after concentration to form a steam condensate, wherein the concentration is a evaporative dehydration; and filtering the steam condensate through a reverse osmosis membrane to form a concentrated solution, wherein the retentate of the reverse osmosis flows back to the evaporative dehydration, and the penetrant of the reverse osmosis can be reused as a fermentation ingredient, as cleaning water or for sewage treatment; and the water content of the concentrated solution after the evaporative dehydration is 5-25 wt %; and the yield of PDO is 99.5%. The preparing method meets the requirements of water resources recycling, reduces the production loss of PDO and BDO (2,3-butanediol) during the concentration, and greatly cuts down on the amount of wastewater.
    Type: Grant
    Filed: May 7, 2020
    Date of Patent: October 19, 2021
    Assignee: SUZHOU SUZHEN BIOENGINEERING CO., LTD
    Inventors: Ji An Luo, Guozhu Shi, Yun Zhang, Bin Liu, Juanjuan Qian, Juan Ding, Wei Wang, Wei Ji
  • Patent number: 11148989
    Abstract: A process for preparing a dienynal compound of the following general formula (2): CH2?CHC?CCH?CH(CH2)nCHO??(2), wherein n represents an integer of 0 to 11, the process comprising a step of hydrolyzing a dialkoxyalkadienyne compound of the following general formula (1): CH2?CHC?CCH?CH(CH2)nCH(OR1)(OR2)??(1) wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 8, more preferably 1 to 4, or R1 and R2 may be bonded to each other to form a divalent hydrocarbon group, R1-R2, having from 2 to 10 carbon atoms, and n represents an integer of 0 to 11, to obtain the dienynal compound (2).
    Type: Grant
    Filed: September 2, 2020
    Date of Patent: October 19, 2021
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuki Miyake, Takeshi Kinsho, Ryo Komatsu
  • Patent number: 11148988
    Abstract: A system and method for crystallization and pelleting of a cannabinoid, including cannabidiol (CBD).
    Type: Grant
    Filed: September 18, 2020
    Date of Patent: October 19, 2021
    Assignee: Marquette Analytica
    Inventor: Robert Opperman
  • Patent number: 11141719
    Abstract: Disclosed herein are methods of treating a hydroformylation catalyst solution wherein the solution comprises rhodium, polyphosphoramidite ligands, and polyphosphoramidite ligand degradation products and wherein the hydroformylation catalyst solution is used to hydroformylate an olefin in an operating hydroformylation unit. In some embodiments, such methods comprise contacting the catalyst solution with a peroxide in the operating hydroformylation unit.
    Type: Grant
    Filed: November 6, 2017
    Date of Patent: October 12, 2021
    Assignee: Dow Technology Investments LLC
    Inventors: Michael A. Brammer, Marinus A. Bigi, Rick B. Watson
  • Patent number: 11141724
    Abstract: A method for efficiently catalyzing furfural to prepare cyclopentanone, and a catalyst and preparation method therefor, are disclosed, in the field of biomass catalytic conversion. The catalyst comprises uniformly dispersed metal active center nanoparticles and oxides obtained by LDHs calcination. The metal active center is single atom Pt/Cu alloy; the LDHs is used as a precursor to prepare a Cu-containing catalyst precursor; after a reduction in H2 atmosphere, small amount of Pt2+ is used for reacting with the Cu-containing catalyst precursor to obtain a monoatomic Pt/Cu catalyst; said catalyst is used to catalyze hydrogenation of an aqueous phase of furfural to prepare cyclopentanone, wherein the reaction temperature is 120-250° C., the reaction pressure is 0.1-5 MPa, the reaction time is 0.5-24 hours, and the reaction solvent is ultrapure water. Low-cost and efficient, the catalyst catalyzes the hydrogenation of an aqueous phase of furfural to prepare cyclopentanone.
    Type: Grant
    Filed: December 24, 2018
    Date of Patent: October 12, 2021
    Assignee: BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY
    Inventors: Jing He, Yanru Zhu, Zhe An
  • Patent number: 11142496
    Abstract: The present invention relates to a method for total chemical synthesis of 9-cis-?-carotene (9CBC), and further provides stable formulations thereof.
    Type: Grant
    Filed: May 21, 2017
    Date of Patent: October 12, 2021
    Assignee: Ramot at Tel-Aviv University Ltd.
    Inventors: Ehud Gazit, Ludmila Buzhansky, Michael Ioffe, Alon Sayer
  • Patent number: 11141677
    Abstract: Liquid-liquid extraction and distillation of a liquid feedstock of at least ethanol, water, acetaldehyde and at least one hydrocarbon-based impurity with a boiling point of between 20° C. and 100° C. at atmospheric pressure, or which generates, with at least one of the compounds of the liquid feedstock and/or with the organic extraction solvent and/or with the aqueous back-washing solvent, an azeotrope and a partition coefficient of between 0.1 and 5 at any point in a back-washing (BW) column of the extraction section, by (a) a liquid-liquid extraction step a washing (W) column, a back-washing (BW) column and at least one injection (F2) of a cut withdrawn in step b), located in the top half of the back-washing column, (b) distillation of an aldehyde and ethanol separation producing at least one aldehyde-rich effluent, one ethanol-rich effluent and one water-rich effluent.
    Type: Grant
    Filed: January 25, 2019
    Date of Patent: October 12, 2021
    Assignees: IFP Energies nouvelles, COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
    Inventors: Frederic Augier, Damien Leinekugel Le Cocq, Rejane Dastillung, Pierre Balz
  • Patent number: 11142492
    Abstract: Methods of isolating phenols from phenol-containing media. The methods include combining a phospholipid-containing composition with the phenol-containing medium to generate a combined medium, incubating the combined medium to precipitate phenols in the combined medium and thereby form a phenol precipitate phase and a phenol-depleted phase, and separating the phenol precipitate phase and the phenol-depleted phase. The methods can further include extracting phenols from the separated phenol precipitate phase. The extracting can include mixing the separated phenol precipitate phase with an extraction solvent to solubilize in the extraction solvent at least a portion of the phenols originally present in the phenol precipitate phase.
    Type: Grant
    Filed: August 26, 2020
    Date of Patent: October 12, 2021
    Assignee: WISCONSIN ALUMNI RESEARCH FOUNDATION
    Inventors: Bradley Bolling, Yuwei Wu, Danielle Voss, Matthew Dorris