Abstract: The present invention relates to, inter alia, pharmaceutical compositions comprising EPA and one or more cardiovascular agents, and to therapeutic methods for treating various diseases and disorders using the same.
Type:
Grant
Filed:
April 29, 2010
Date of Patent:
June 15, 2021
Assignee:
Amarin Pharmaceuticals Ireland Limited
Inventors:
Mehar Manku, Ian Osterloh, Pierre Wicker, Rene Braeckman, Paresh Soni
Abstract: Some embodiments of the present invention relate to processes to recover rhodium from a hydroformylation process. In some embodiments, the process to recover rhodium from the hydroformylation process comprises (a) treating a catalyst-containing stream from the hydroformylation process with 2.5 to 20 weight percent, based on the total weight of the stream, of a water-soluble organic amine of the following structure: wherein R32, R33, and R34 are each independently alkyls and ethoxylates, and wherein no more than one of R32, R33, and R34 is alkyl; (b) heating the resulting solution in the presence of syngas to a temperature of at least 65° C. to generate a rhodium-rich phase and a supernatant; and (c) removing the supernatant to recover the rhodium-rich phase.
Abstract: A method is useful for the continuous production of ketones from a compound with at least one epoxide group in at least one fixed bed reactor. A catalyst composition is used with at least one noble metal and at least one metal oxide. To reduce the proportions of high-boilers which form in the reaction, an inert gas is introduced so that a carbon monoxide partial pressure of 50 mbar or less is set in the reactor.
Type:
Grant
Filed:
June 3, 2019
Date of Patent:
June 15, 2021
Assignee:
Evonik Operations GmbH
Inventors:
Kévin Micoine, Luca Cameretti, Ralf Meier, Marcus Matthias Stergar, Dominik Schulte-Althoff, Axel Prinz
Abstract: Glycine is an organic compound that can be used in the making of a synthetic acid that obviates all the drawbacks of strong acids such as hydrochloric acid. The new compound is made by dissolving glycine in water, in a weight ratio of approximately 1:1 to 1:1.5. The solution is mixed until the glycine is essentially fully dissolved in the water. Once dissolution is complete, hydrogen chloride gas is dissolved in the solution to produce the new compound, which can be referred to as hydrogen glycine. Also disclosed is a method for adjusting the pH of a fluid, the method comprising adding an effective amount of a solution to the fluid for adjusting the pH thereof to a desired level, wherein the solution is prepared by mixing glycine in water to form a glycine solution; and adding hydrogen chloride to the glycine solution.
Type:
Grant
Filed:
June 29, 2020
Date of Patent:
June 15, 2021
Assignee:
GREEN PRODUCTS & TECHNOLOGIES, L.L.C.
Inventors:
John T. MacDonald, II, John Thomas MacDonald, III
Abstract: The invention relates to a method for producing terpene aldehydes and terpene ketones by oxidatively dehydrogenating the corresponding terpene alcohols, comprising or consisting of the following steps: (a) providing terpene alcohols or terpene-alcohol-containing reactants; (b) bringing the starting substances from step (a) in contact with a heterogeneous ruthenium catalyst; (c) heating the mixture from step (b) to at least 150° C. in the presence of oxygen; optionally (d) separating the terpene aldehydes or terpene ketones from the obtained reaction mixture.
Type:
Grant
Filed:
August 26, 2017
Date of Patent:
June 8, 2021
Assignee:
SYMRISE AG
Inventors:
Anna Kulik, Reinhard Eckelt, Angela Köckritz, Katja Neubauer
Abstract: The present invention relates to, according to a primary aspect, a method for manufacturing a mixture comprising rotundone. A further aspect of the present invention relates to mixtures containing rotundone as well as their use for generating, imparting or modifying, preferably enhancing, one or several taste and/or olfactory impressions. Moreover, the invention relates to a pharmaceutical preparation for nutrition, for oral care or for pleasure or a cosmetic pharmaceutical preparation or a pharmaceutical preparation intended for oral consumption or an intermediate good for manufacturing a pharmaceutical preparation for nutrition, for oral care or for pleasure or a cosmetic pharmaceutical preparation or a pharmaceutical preparation intended for oral consumption comprising a mixture according to the invention and furthermore to a method for manufacturing said preparation or intermediate good.
Type:
Grant
Filed:
February 27, 2017
Date of Patent:
June 8, 2021
Assignee:
SYMRISE AG
Inventors:
Michael Backes, Tobias Vössing, Nadine Heinemeier, Lars Meier, Dietmar Schatkowski, Willi Krieger, Katharina Reichelt, Susanne Otte-Hölscher
Abstract: A process for preparing an aromatic polyamine mixture including 4,4?-methylenedi(phenylamine) and higher homologues of MDA is provided. The process includes steps of (i) reaction of aniline with formaldehyde by means of an acid catalyst to form a crude product mixture (I), (ii) neutralization of the crude product mixture (I) and removal of the salts formed; (iii) isolation of aniline; (iv) distillation of the resulting crude product mixture so as to separate off (iv-1) a mixture (II) of MDA isomers (II-1) containing from 8 to 20% by weight of 4,4?-methylenedi(phenylamine) and not more than 0.3% by weight of secondary components (II-2) and (iv-2) a low boiler mixture of at least 55% by weight of secondary components (II-2) and MDA isomers (II-1); and (v) recirculation of the mixture (II).
Type:
Grant
Filed:
January 12, 2017
Date of Patent:
June 8, 2021
Inventors:
Viktor Ladnak, Silvia Tauro, Kerstin Heinen, Kai Thiele, Klaus-Peter Metzner, Torsten Mattke
Abstract: A method for producing unsaturated macrocyclic monoketones comprising the following steps: (a) preparing macrocyclic dienes with a ring size of at least 9 carbon atoms; (b) contacting the starting materials from step (a) with (b1) a palladium(II) salt and/or a palladium(II) complex; and (b2) an oxidant; and (b3) a solvent; and optionally (b4) a ligand; and optionally (b5) a co-catalyst; and optionally (b6) an acid.
Type:
Grant
Filed:
October 25, 2017
Date of Patent:
June 1, 2021
Assignee:
Symrise AG
Inventors:
Tom Brunzel, Angela Köckritz, Andreas Martin, Diego A. Jaime Trevino
Abstract: [Problem] The present invention provides an industrially-preferable, cost-efficient, low-cost production method for 4-hydroxy-2-hydroxymethyl-2-cyclopenten-1-one (a compound represented by formula (I)) useful as a medicine, an agricultural chemical, or a raw material or intermediate of a medicine, an agricultural chemical, or the like. [Solution] According to the present invention, this compound represented by formula (I) is produced by subjecting an easily available compound represented by formula (II) (tri-O-acetyl-D-glucal) to a heating reaction in pressurized water.
Type:
Grant
Filed:
February 12, 2019
Date of Patent:
May 25, 2021
Assignees:
Tohoku University, Genesis Research Institute, Inc.
Abstract: A process for preparing C4 to C13 monohydroxy compounds from a bottom fraction arising in the distillation of a crude mixture of C4 to C13 oxo-process aldehydes from cobalt-catalyzed or rhodium-catalyzed hydroformylation, or in the distillation of a crude mixture of C4 to C13 oxo-process alcohols, which comprises contacting the bottom fraction in the presence of hydrogen with a catalyst comprising copper oxide and aluminum oxide, at a temperature of 150° C. to 300° C. and a pressure of 20 bar to 300 bar and subjecting the resulting crude hydrogenation product to distillation, and the amount of C4 to C13 monohydroxy compounds present in the crude hydrogenation product after the hydrogenation being greater than the amount of C4 to C13 monohydroxy compounds given stoichiometrically from the hydrogenation of the ester and aldehyde compounds present in the bottom fraction, including the C4 to C13 monohydroxy compounds still present in the bottom fraction before the hydrogenation.
Type:
Grant
Filed:
May 14, 2018
Date of Patent:
May 25, 2021
Assignee:
BASF SE
Inventors:
Stephan Zuend, Rainer Papp, Boris Breitscheidel, Armin Lange De Oliveira
Abstract: A method for preparing dimethylolbutanal including performing an aldol reaction of n-butyraldehyde (n-BAL) and paraformaldehyde (PFA) in the presence of water and an alkylamine catalyst, in which a weight ratio of the paraformaldehyde:water is 1:0.35 to 1:0.85.
Type:
Grant
Filed:
July 10, 2019
Date of Patent:
May 18, 2021
Assignee:
LG CHEM, LTD.
Inventors:
Min Ji Choi, Sungshik Eom, Dawon Jung, Tae Yun Kim, Dong Hyun Ko, Mi Young Kim
Abstract: Methods and systems for preparing acetone from cumene hydroperoxide (CHP) are disclosed. The methods and systems involve an acetone purification column configured to separate acetone from other components of the product/reactant stream. The acetone purification column is equipped with a side draw configured to route a portion of the column contents to a caustic treating vessel where the contents are reacted with a dilute aqueous alkaline solution to remove aldehydes from the acetone product. The contents of the caustic treating vessel are then routed back to the acetone purification column. Using a separate caustic treating vessel for the aldehydes removal provides increased contact time between the acetone product and the alkaline solution, thereby affording greater aldehydes removal.
Abstract: The present disclosure is directed to methods of preparing prostaglandin J natural products by stereoretentive metatheses reactions and intermediates used in the synthesis of these natural products, including the use of intermediates of Formula (I-A), where R1 is defined in the specification
Type:
Grant
Filed:
July 7, 2020
Date of Patent:
May 4, 2021
Assignee:
California Institute of Technology
Inventors:
Jiaming Li, Chen Xu, Tonia S Ahmed, Robert H Grubbs, Brian M. Stoltz
Abstract: A method of obtaining ketones from a fermentation process may include collecting an off-gas and a fermented broth from a fermenter, transferring the off-gas from the fermenter to a ketone recuperation module and the fermented broth to a fluid separating module, and isolating the ketones from both the off-gas and the fermented broth. The off-gas and the fermented broth may both comprise a ketone.
Type:
Grant
Filed:
June 4, 2020
Date of Patent:
April 27, 2021
Assignee:
Braskem S.A.
Inventors:
Liliana Zanelli de O Martins Ikari, Fernanda Munhoz Anderle, Melina Gesteira Souza, Lucas Gualberto Santos Costa
Abstract: Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.
Type:
Grant
Filed:
April 14, 2020
Date of Patent:
April 20, 2021
Assignee:
TRUSTEES OF BOSTON UNIVERSITY
Inventors:
John A. Porco, Aaron B. Beeler, Lauren E. Brown, Richard V. Trilles
Abstract: Some embodiments of the present invention relate to processes for reducing heavies formation in a solution comprising one or more aldehydes, such as a reaction fluid in a hydroformylation process. In some embodiments, the process comprises providing 0.1 to 5 wt. percent of an organic nitrogen compound based on the total weight of the aldehyde solution, the organic nitrogen compound comprising: wherein each of R1-R5 are independently hydrogen, an alkyl, or an aryl radical.
Abstract: The present invention aims to provide a method for preparing an aldehyde, which can prepare a target aldehyde with high selectivity and can also suppress the production of by-products. The present invention relates to a method for preparing an ?,?-unsaturated aldehyde. The method includes a step of reacting a compound of formula (I) with a compound of formula (II) to provide an ?,?-unsaturated aldehyde of formula (III). An alkali metal hydroxide and an alkanol having 1 to 4 carbon atoms are used in the step. The amount of the alkali metal hydroxide is 8 mol % or more and 12 mol % or less with respect to the compound of formula (I). The total amount of water contained in materials that are used in the reaction is 10 mol % or more and 50 mol % or less with respect to the compound of formula (I).
Abstract: Methods of purifying crude 4-hydroxyacetophenone using one or more solvents as well as products comprising or consisting of crystallized 4-hydroxyacetophenone and one, two or more solvent(s). The products may be obtained or obtainable from the methods for purifying crude 4-hydroxyacetophenone.
Type:
Grant
Filed:
August 24, 2020
Date of Patent:
April 20, 2021
Assignees:
SYMRISE AG, SINO-HIGH (CHINA) CO. LTD.
Inventors:
Ravikumar Pillai, Sven Siegel, Ev Suess, Karolin Bolte, Yan Liuxin
Abstract: A method comprising synthesizing a cyclic organic compound (3) via reaction of an substituted alkene (1) with an unsubstituted or substituted acrylic acid (2) in the presence of a sulfonic acid reagent to make the cyclic organic compound (3) R1(H)C?C(H)R2 (1)
Abstract: The invention relates to a crystal (C) consisting of at least 95% by weight of 4,4?-dichlorodiphenylsulfoxide, 0 to 2% by weight of impurities and 0 to 3% by weight of an organic solvent (os). Moreover, the present invention relates to a crystal composition (CC) comprising crystals (C) and a process for the production of the crystal composition (CC) and the crystal (C).
Type:
Grant
Filed:
February 7, 2020
Date of Patent:
April 13, 2021
Assignee:
BASF SE
Inventors:
Indre Thiel, Christian Schuetz, Stefan Blei, Jun Gao, Lukas Metzger