Patents Examined by Sikarl A. Witherspoon
  • Patent number: 11225451
    Abstract: The present inventions relates to the preparation of 3,3,5-trimethylcyclohexylidene bisphenol. Especially, the present invention relates to the preparation of 3,3,5-trimethylcyclohexylidene bisphenol from 3,3,5-trimethylcyclohexanone and phenol in the presence of a gaseous acidic catalyst. The preparation comprises a first drying step and a second drying step wherein in the second drying step the temperature is increased in comparison to first drying step or in the second drying step the pressure is lowered in comparison to first drying step, or in second drying step both the temperature is increased and the pressure is lowered in comparison to the first drying step (d1).
    Type: Grant
    Filed: November 13, 2019
    Date of Patent: January 18, 2022
    Assignee: Covestro Intellectual Property GMBH & Co. KG
    Inventors: Johan Vanden Eynde, Kristof Heylen, Anja Ehrig, Lars Frye
  • Patent number: 11225450
    Abstract: This invention relates to a process for preparing a calixarene compound by reacting a phenolic compound and an aldehyde in the presence of at least one nitrogen-containing base as a catalyst to form the calixarene compound. The invention also relates to processes for high-yield, high solid-content production of a calixarene compound, with high selectivity toward a high-purity calix[8]arene compound, without carrying out a recrystallization step.
    Type: Grant
    Filed: November 2, 2020
    Date of Patent: January 18, 2022
    Assignee: SI GROUP, INC.
    Inventors: Cornelius Haase, Ricky Biittig, Allyson Staats, Philip David Atwood, Jim Webb, Kelly Chichak
  • Patent number: 11220474
    Abstract: A method for preparing dehydro-cyclofarnesal from dehydro-farnesal by cyclization in the presence of an acid may include the dehydro-farnesal being obtained from the farnesal by dehydrogenation and may further includes the cyclization being carried out in the presence of an acid selected from Lewis acids, Bronstedt acids, and zeolites. The synthesis of vitamin A using this method further includes the conversion of dehydro-cyclofarnesal into vitamin A.
    Type: Grant
    Filed: August 19, 2019
    Date of Patent: January 11, 2022
    Assignee: ADISSEO FRANCE S.A.S.
    Inventors: Patrick Rey, Robert Huet, Sylvain Aubry, Vivien Henryon
  • Patent number: 11214497
    Abstract: Disclosed are a perovskite compound, a method for producing the perovskite compound, a catalyst for a fuel cell including the perovskite compound, and a method for producing the catalyst. The perovskite compound overcomes the low stability of palladium due to its perovskite structural properties. Therefore, the perovskite compound can be used as a catalyst material for a fuel cell. In addition, the use of palladium in the catalyst instead of expensive platinum leads to an improvement in the price competitiveness of fuel cells. The catalyst is highly durable and catalytically active due to its perovskite structure.
    Type: Grant
    Filed: August 7, 2019
    Date of Patent: January 4, 2022
    Assignees: Korea Institute of Science and Technology, Industrial Cooperation Foundation Chonbuk National University, Global Frontier Center for Multiscale Energy Systems
    Inventors: Sung Jong Yoo, Sehyun Lee, Hee-Young Park, So Young Lee, Hyun Seo Park, Jin Young Kim, Jong Hyun Jang, Hyoung-Juhn Kim, Pil Kim, Jae Young Jung, Yeonsun Sohn
  • Patent number: 11208419
    Abstract: The invention discloses a phenylbenzofuran compound, preparation method therefor, composition containing the same and medical application thereof. The phenylbenzofuran compound is represented by the formula The preparation method includes a traditional Chinese medicine extraction method by using Sophorae Tonkinensis Radix Et Rhizoma coarse powder as a raw material, and a chemical synthesis method. Active component of the composition is phenylbenzofuran compound, and composition is a drug, food or health product. The application of the phenylbenzofuran compound in the preparation of a drug, a food or health product for preventing or treating a tumor, wherein the tumor is nasopharyngeal carcinoma. The phenylbenzofuran compound is prepared by traditional Chinese medicine extraction method and chemical synthesis method. It has been proved that phenylbenzofuran has certain inhibition effect on nasopharyngeal carcinoma cells CNE-1 and CNE-2 by tumor cell experiments in vitro.
    Type: Grant
    Filed: January 17, 2019
    Date of Patent: December 28, 2021
    Assignee: Guangxi Botanical Garden of Medicinal Plants
    Inventors: Jianhua Miao, Lingling Wu, Zhijun Song, Bingxiong Yan, Xiaolei Zhou, Shuo Wang, Caiyun Yao
  • Patent number: 11208326
    Abstract: Dinitrogen tetroxide (N2O4) is synthesized in an apparatus by the reaction of concentrated nitric acid with copper. Oxygen is applied as a carrier gas to convert NO to NO2, and water vapor is removed with a tube dryer. A molecular sieve is applied to reduce and remove impurities.
    Type: Grant
    Filed: July 18, 2019
    Date of Patent: December 28, 2021
    Assignee: VERO Biotech LLC
    Inventors: David H. Fine, Thorsten Schmidt, Bryan Johnson, Alessandra Miranda, Edward Bromberg, Marjorie Nelson
  • Patent number: 11203561
    Abstract: A method for separating monoethylene glycol (MEG) from one or more oxygenates. The method includes providing a stream comprising MEG and one or more oxygenates to a distillation column, providing a water feed stream to a bottom of the distillation column, and removing a recovery stream comprising MEG from the distillation column. The distillation column is operated at higher temperatures than the thermal stability of MEG and the one or more oxygenates.
    Type: Grant
    Filed: February 19, 2019
    Date of Patent: December 21, 2021
    Inventors: Pieter Huizenga, Kai Jürgen Fischer
  • Patent number: 11203010
    Abstract: A novel catalyst composition and its use in the dehydrogenation of alkanes to olefins. The catalyst comprises a Group VIII noble metal and a metal selected from the group consisting of manganese, vanadium, chromium, titanium, and combinations thereof, on a support. The Group VIII noble metal can be platinum, palladium, osmium, rhodium, rubidium, iridium, and combinations thereof. The support can be silicon dioxide, titanium dioxide, aluminum oxide, silica-alumina, cerium dioxide, zirconium dioxide, magnesium oxide, metal modified silica, silica-pillared clays, silica-pillared micas, metal oxide modified silica-pillared mica, silica-pillared tetrasilicic mica, silica-pillared taeniolite, zeolite, molecular sieve, and combinations thereof. The catalyst composition is an active and selective catalyst for the catalytic dehydrogenation of alkanes to olefins.
    Type: Grant
    Filed: July 31, 2018
    Date of Patent: December 21, 2021
    Inventors: Jeffrey T. Miller, Zhenwei Wu, Evan C. Wegener, Stephen Purdy, Nicole J. Libretto
  • Patent number: 11198665
    Abstract: A (Z)-solanone has the steric formula of: or with the name of (S,Z)-5-isopropyl-8-methyl-6,8-diene-2-one or (R,Z)-5-isopropyl-8-methyl-6,8-diene-2-one. A process for the preparation of the (Z)-type solanone and the use thereof in flavoring of cigarette shred are further disclosed. The process includes the following steps: (1) reacting isopentanal and methyl vinyl ketone, under the action of a catalyst and a co-catalyst, to give (S)-2-isopropyl-5-carbonylhexanal or (R)-2-isopropyl-5-carbonylhexanal; (2) reacting the (S)-2-isopropyl-5-carbonylhexanal or the (R)-2-isopropyl-5-carbonylhexanal obtained in step (1) with (iodomethyl)triphenylphosphonium iodide, to give (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or (R,Z)-7-iodo-5-isopropyl-6-ene-2-one; and (3) reacting the (S,Z)-7-iodo-5-isopropyl-6-ene-2-one or the (R,Z)-7-iodo-5-isopropyl-6-ene-2-one obtained in step (2) with pinacol isopropenylborate in the presence of a catalyst to give the (Z)-solanone.
    Type: Grant
    Filed: June 1, 2020
    Date of Patent: December 14, 2021
    Inventors: Sheng Lei, Zhihua Liu, Kai Wang, Zhenjie Li, Deshou Mao, Kunmiao Wang, Li Gao, Lei Fu, Yipeng Zhang, Wei Zhe, Ying Yang, Qianghui Zhou
  • 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: 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
    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: 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: 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
    Inventors: Shilei Zhang, Yujian Mao
  • 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: 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: 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
    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
    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: 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
    Inventors: Daijiro Tsukamoto, Masateru Ito, Katsushige Yamada, Masato Akahira, Daisuke Yamamoto, Koji Yamauchi