Patents Examined by Sikarl A. Witherspoon
  • Patent number: 10435344
    Abstract: An inexpensive, stereoselective synthesis for nootkatone, tetrahydronootkatone, and their derivatives is disclosed utilizing ozonolysis. The starting materials used in the synthesis are inexpensive and the reactions are commercially feasible and amenable to scaling up. The principal starting material, (?)-?-Pinene, is on the GRAS list (generally recognized as safe).
    Type: Grant
    Filed: December 8, 2016
    Date of Patent: October 8, 2019
    Assignee: Board of Supervisors of Louisiana State University and Agricultural and Mechanical College
    Inventor: Roger Laine
  • Patent number: 10435346
    Abstract: A process for the distillation of an aldehyde mixture comprising a straight-chain aldehyde and a branched-chain aldehyde is described in which the process comprises: supplying a feed comprising the aldehyde mixture to a first separation vessel; operating said first separation vessel at a first temperature and a first pressure such that separation occurs; recovering a first stream comprising the straight-chain aldehyde from said first separation vessel and supplying said first stream to a second separation vessel; operating said second separation vessel at a second temperature and a second pressure such that separation occurs; recovering a product stream comprising the straight-chain aldehyde and a second stream comprising high-boiling components from said second separation vessel, and supplying said second stream to a third separation vessel; operating said third separation vessel at a third temperature and a third pressure such that separation occurs; and recovering a third stream comprising the aldehyde mix
    Type: Grant
    Filed: April 13, 2017
    Date of Patent: October 8, 2019
    Assignee: Johnson Matthey Davy Technologies Limited
    Inventors: Adrian Lord, Martin Lucas Smidt, Atul Manilal Shah
  • Patent number: 10428007
    Abstract: The present invention relates to a method for producing unsaturated aldehydes and unsaturated carboxylic acids. According to the present invention, a method for producing unsaturated aldehydes and unsaturated carboxylic acids which can impart activity and control temperature independently in fixed catalyst layer zones in a shell-and-tube reactor, thereby exhibiting improved yield and operation stability, is provided.
    Type: Grant
    Filed: October 17, 2017
    Date of Patent: October 1, 2019
    Assignee: LG CHEM, LTD.
    Inventors: Byung Yul Choi, Hyun Jong Shin, Junghoon Chang, Young Hyun Choe, Jun Seok Ko, Sang Hun Jeon
  • Patent number: 10428001
    Abstract: The disclosure relates to a method of performing ozonolysis or ozone-based oxidation on a liquid or emulsified reagent using a tubular falling firm reactor with one or multiple tubes wherein the combined ozone and carrier gas flow is co-current.
    Type: Grant
    Filed: August 7, 2018
    Date of Patent: October 1, 2019
    Assignee: P2 SCIENCE, INC.
    Inventors: Patrick Foley, Neil Burns, Alexandre Chapeaux, Icilio Adami, Antonio Milicia
  • Patent number: 10421704
    Abstract: Process for Pd-catalyzed hydroxycarbonylation of diisobutene: ratio of 3,5,5-trimethylhexanoic acid/H2O.
    Type: Grant
    Filed: November 13, 2018
    Date of Patent: September 24, 2019
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Rui Sang, Peter Kucmierczyk, Kaiwu Dong, Ralf Jackstell, Matthias Beller, Robert Franke
  • Patent number: 10414707
    Abstract: The present invention relates to a process for preparing 3-methyl-2-butenol (prenol) and 3-methyl-2-butenal (prenal) from 3-methyl-3-butenol (isoprenol), in which 3-methyl-3-butenol is subjected to a catalytic isomerization over a carbon-supported Pd catalyst in the presence of a gas mixture comprising 1% to 15% by volume of oxygen to obtain a first product mixture, and the first product mixture is subjected to an oxidative dehydrogenation over a Pd catalyst comprising SiO2 and/or Al2O3 as support material, or over a carbon-supported Pd/Au catalyst in the presence of a gas mixture comprising 5% to 25% by volume of oxygen.
    Type: Grant
    Filed: March 14, 2017
    Date of Patent: September 17, 2019
    Assignee: BASF SE
    Inventors: Martine Dehn, Bernhard Brunner, Klaus Ebel, Sabine Huber
  • Patent number: 10413892
    Abstract: A catalyst including: neodymium; sodium; and a ligand, which is a compound expressed by Structural Formula (1) below, wherein the neodymium and the ligand form a complex at a molar ratio of 1:2 (neodymium:ligand):
    Type: Grant
    Filed: November 21, 2016
    Date of Patent: September 17, 2019
    Assignee: Microbial Chemistry Research Foundation
    Inventors: Masakatsu Shibasaki, Naoya Kumagai, Akihito Nonoyama, Kazuki Hashimoto, Akira Saito
  • Patent number: 10407372
    Abstract: Embodiments of the present invention relate to processes for the hydroformylation of olefins to produce aldehydes. In some embodiments, processes of the present invention are capable of maintaining high C2-C4 olefin conversion and/or provide more compact hydroformlyation processes.
    Type: Grant
    Filed: March 15, 2017
    Date of Patent: September 10, 2019
    Assignee: Dow Technology Investments LLC
    Inventors: Kathleen Simpson, Gerald L. Smith
  • Patent number: 10399927
    Abstract: The present invention relates to a preparation method of a long-chain compound, which includes the following steps: (1) carrying out condensation reaction on H—R2 and R5N-Glu(OR4)—OR3, wherein, R3 is a carboxyl protecting group, R4 is a carboxyl activating group, and R5 is an amino protecting group; obtaining a compound of formula II; (2) removing carboxyl protecting group R3 and amino protecting group R5 of the compound shown in formula II to obtain a compound of formula III; (3) carrying out condensation reaction on the compound shown in formula III and to obtain a compound shown in formula I. The method reduces the time of deprotection, and all the reactions can be carried out in a solvent with low boiling point. The post-processing requires only simple washing and recrystallization to obtain the product with higher purity, so the method is suitable for large-scale production.
    Type: Grant
    Filed: February 29, 2016
    Date of Patent: September 3, 2019
    Assignee: HYBIO PHARMACEUTICAL CO., LTD.
    Inventors: Youjin Chen, Pengcheng Mi, Anjin Tao, Jiancheng Yuan
  • Patent number: 10399062
    Abstract: A process for preparing a catalyst includes impregnating a metal oxide carrier with an aqueous solution to form an impregnated carrier; drying the impregnated carrier to form a dried, impregnated carrier; and heat-treating the dried, impregnated carrier in air to form the catalyst; wherein: the aqueous solution includes a copper salt; and from about 3 wt % to about 15 wt % of a C3-C6 multifunctional carboxylic acid; and the catalyst includes from about 5 wt % to about 50 wt % copper oxide.
    Type: Grant
    Filed: March 30, 2016
    Date of Patent: September 3, 2019
    Assignee: BASF Corporation
    Inventors: Keenan Lee Deutsch, Rostam J. Madon
  • Patent number: 10399934
    Abstract: The present invention relates to a process for preparing alkanesulphonic acid by oxidizing an alkyl mercaptan, a dialkyl disulphide and/or a dialkyl polysulphide having three to nine sulphur atoms with an oxidizing agent, wherein additional oxidizing agent is fed into the oxidation if as yet unoxidized alkyl mercaptan and/or unoxidized dialkyl disulphide and/or at least one intermediate from the oxidation of the dialkyl disulphide and/or of the dialkyl polysulphide is present in the reaction output, and a corresponding apparatus for performance of oxidation reactions.
    Type: Grant
    Filed: November 30, 2016
    Date of Patent: September 3, 2019
    Assignee: Evonik Degussa GmbH
    Inventors: Benjamin Fonfe, Nadine Duerr, Harald Jakob, Chiu Kee Cheung, Andreas Doerflein, Sebastian Fuss
  • Patent number: 10392335
    Abstract: There is provided a method for producing hydroxypivalaldehyde (HPA), including steps (i) to (iii) below in this order, Step (i): a reaction step of reacting IBAL with FA to produce a reaction solution containing HPA, step (ii): an extraction step of extracting the reaction solution with an aldehyde solvent represented by formula (1) under basicity to obtain an extract containing HPA, and step (iii): a distillation and collection step of distilling the extract and then collecting HPA from the residue, wherein R represents a saturated alkyl group having 3 or more and 7 or less carbon atoms, further wherein the distillation step of the step (iii) is a step of distilling an extract in the presence of water, and an amount of the water which is subjected to the distillation is 100 parts by mass or more and 2,000 parts by mass or less with respect to a total amount, 100 parts by mass, of isobutyraldehyde (IBAL) derived from a raw material and an aldehyde solvent represented by formula (1) in an extract
    Type: Grant
    Filed: January 5, 2017
    Date of Patent: August 27, 2019
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yumi Sato, Masahiro Yamane
  • Patent number: 10392334
    Abstract: A method and a system for inexpensively producing a corresponding target ketone and/or alcohol by decomposing hydroperoxide rapidly and with high selectivity using an aqueous alkaline solution and by recovering and recycling alkali. The method includes neutralizing at least a part of a carboxylic acid in the oxidation reaction solution by contacting the oxidation reaction solution with a first alkaline solution including a carbonate of an alkali metal, and separating the reaction mixture into a first oil phase and a first water phase; decomposing the hydroperoxide and the ester compound in the first oil phase by contacting the first oil phase with a second alkaline solution having a higher pH value than the first alkaline solution, and separating the reaction mixture into a second oil phase and a second water phase; and recovering the carbonate of an alkali metal from the first water phase and recycling the carbonate of an alkali metal to the first alkaline solution.
    Type: Grant
    Filed: December 6, 2016
    Date of Patent: August 27, 2019
    Assignee: UBE INDUSTRIES, LTD.
    Inventors: Yoshinori Sugimura, Kazunori Kurosawa, Kazuo Yamato, Junichi Kugimoto, Joji Kawai, Wanna Sirisuksukon, Nantariya Ngamsup
  • Patent number: 10392590
    Abstract: A method and system for distilling alcohol in an alcohol production process is disclosed. The method can include fermenting a mixture of water and milled grain to produce alcohol-laden beer, which can be distilled in a beer column maintained at a subatmospheric pressure to produce a vapor, primarily including alcohol, and whole stillage. Stillage is separated from the whole stillage. Water is evaporated from the separated stillage to produce first-concentrated stillage and first effect steam. Water from the first-concentrated stillage is evaporated with heat from the first effect steam to produce second effect steam. In one embodiment, second effect steam can be used to supply sufficient heat to a side stripper for distilling the alcohol-laden beer. In another embodiment, the method can include generating steam from one or more steam generator to supply sufficient heat to the beer column for distilling the alcohol-laden beer.
    Type: Grant
    Filed: January 7, 2019
    Date of Patent: August 27, 2019
    Assignee: Fluid Quip Process Technologies, LLC
    Inventors: Neal Jakel, John Kwik, Michael Hora
  • Patent number: 10392333
    Abstract: A method for producing formaldehyde from methanol. The method includes the steps of packing a catalyst comprising platinum, bismuth and a support material into a reactor, introducing a reactant mixture containing methanol into the reactor such that the reactant mixture containing methanol is in close contact with the catalyst, and heating the reactant mixture containing methanol to a temperature for a period of time.
    Type: Grant
    Filed: December 19, 2018
    Date of Patent: August 27, 2019
    Assignee: Purdue Research Foundation
    Inventors: Arvind Varma, Yang Xiao
  • Patent number: 10384998
    Abstract: To provide a method for producing propionaldehyde directly from glycerol with high yield, gasified glycerol is brought into contact with a silica-type regular mesoporous body. More specifically, gasified glycerol is supplied to a catalyst layer containing a regular mesoporous body while heating the catalyst layer at a temperature ranging from 200 to 800° C. in such a manner that a W/F value can fall within the range from 0.001 to 1000 g·min/ml inclusive wherein W represents an amount (g) of a catalyst and F represents a supply rate (ml/min) of supplied glycerol.
    Type: Grant
    Filed: November 28, 2018
    Date of Patent: August 20, 2019
    Assignees: Mitsubishi Chemical Corporation, TOKUSHIMA UNIVERSITY
    Inventors: Yuki Kato, Wataru Ninomiya, Shigeru Sugiyama
  • Patent number: 10384999
    Abstract: Provided is a method of producing 2-hydroxy-1,4-naphthoquinone in a large amount, a high yield, and inexpensively. This method comprises oxidizing 2-hydroxynaphthalene with hydrogen peroxide in (1) an alkaline aqueous solution or in (2) a mixture of an alkaline aqueous solution with an inert organic solvent incompatible with water, in the presence of a vanadium catalyst.
    Type: Grant
    Filed: June 24, 2016
    Date of Patent: August 20, 2019
    Assignee: AGRO-KANESHO CO., LTD.
    Inventor: Seiji Kakinuma
  • Patent number: 10377690
    Abstract: Disclosed is a method for forming enals from corresponding alehydes in a single enclosed unit such as a divided wall reaction distillation unit. The method of the present invention includes (a) feeding an aldehyde feed stream comprising at least one aldehyde reactant into a reaction zone contained within said single enclosed unit; (b) reacting said at least one aldehyde reactant in said reaction zone in the presence of a catalyst to form an enal-containing reaction zone effluent comprising an enal; (c) purifying said enal-containing reaction zone effluent in a first separation zone within said single enclosed unit to form an enal-rich product mixture and a residual unreacted aldehyde mixture; and (d) collecting from said single enclosed unit at least a portion of said enal-rich product mixture. The method of the present invention results in high enal yields at a markedly reduced capital cost and energy consumption as compared to prior art processes.
    Type: Grant
    Filed: August 22, 2018
    Date of Patent: August 13, 2019
    Assignee: Eastman Chemical Company
    Inventors: Scott Allen Owens, Robert Lin, Jody Lee Rodgers
  • Patent number: 10370317
    Abstract: A method for producing ketones includes a) providing a feedstock of biological origin having fatty acids and/or fatty acid derivatives having an average chain length of 24 C-atoms or less; b) subjecting the feedstock to a catalytic ketonization reaction in the presence of aK2O/TiO2-catalyst; and c) obtaining from the ketonization reaction a product stream having ketones, which ketones have a longer average hydrocarbon chain length than the average hydrocarbon chain length in the feedstock, wherein step b) is carried out directly on the feedstock and in the presence of the K2O/TiO2-catalyst as the sole catalyst applied in the ketonization reaction.
    Type: Grant
    Filed: July 5, 2018
    Date of Patent: August 6, 2019
    Assignee: NESTE OYJ
    Inventors: Mika Kettunen, Jukka Myllyoja, Rami Piilola
  • Patent number: 10369550
    Abstract: The invention provides a catalyst system comprising: a) one or more silver tungstate-containing species; and b) one or more catalytic species suitable for hydrogenation, wherein the weight ratio of said one or more silver tungstate-containing species to the one or more catalytic species suitable for hydrogenation is greater than 2.5:1, on the basis of the total weight of the catalyst system; and a process for the preparation of monoethylene glycol from starting material comprising one or more saccharides, by contacting said starting material with hydrogen in a reactor at a reactor temperature in the range of from 145 to 190° C. in the presence of a solvent and said catalyst system.
    Type: Grant
    Filed: November 17, 2016
    Date of Patent: August 6, 2019
    Assignee: SHELL OIL COMPANY
    Inventors: Smita Edulji, Evert Van Der Heide