Abstract: In methods for preparing an alkyl carboxylic acid ester according to embodiments of the present invention, a first reaction product is produced by reaction of a carboxylic acid stream and a first alcohol stream in a preliminary reactor. A second reaction product is produced by at least partially removing alcohol and water from the first reaction product. The second reaction product is esterified by reaction with a second alcohol stream in a main reactor. An alkyl carboxylic acid ester is recovered from the main reactor.
Type:
Grant
Filed:
November 25, 2019
Date of Patent:
March 21, 2023
Assignee:
GS CALTEX CORPORATION
Inventors:
Kyoung Jun Lee, In Chang Choi, Woo Young Kim
Abstract: Provided is a compound represented by Formula (VI) for preparing lisdexamphetamine or a salt thereof. Also provided is a method for preparing lisdexamfetamine or a salt thereof including performing reduction and debenzylation of the compound represented by Formula (VI) by hydrogenation.
Abstract: Methods for the preparation of bio-based malonic acid and diester derivatives of malonic acid are provided. For example, a dialkyl malonate may be prepared by the steps of (i) separating calcium malonate crystals from a fermentation broth; (ii) obtaining dissolved malonic acid; (iii) crystallizing the dissolved malonic acid; and (iv) performing esterification to obtain the dialkyl malonate. The disclosed methods produce diester derivatives of malonic acid with fewer impurities, which is useful for many industrial processes. The diester derivatives of malonic acid can be purified from existing sources of malonic acid, or from malonic acid made from a renewable carbon source.
Type:
Grant
Filed:
February 12, 2019
Date of Patent:
March 7, 2023
Assignee:
LYGOS, INC.
Inventors:
Jeffrey A. Dietrich, Eric Steen, Johan van Walsem
Abstract: A method for manufacturing an isocyanate compound represented by formula (2) (2) wherein R1 represents a methyl group, an ethyl group, a cyclopropyl group, a chlorine atom, a bromine atom, or a methoxy group; and R2 represents an alkyl group having 1 to 6 carbon atoms, comprising reacting an aniline compound represented by formula (1) (1) wherein R1 and R2 are defined as above with a phosgene compound at a temperature of from 40° C. to the boiling point of the inert solvent in at least one kind of inert solvent.
Type:
Grant
Filed:
December 11, 2019
Date of Patent:
February 28, 2023
Assignee:
BASF SE
Inventors:
Volker Maywald, Roland Goetz, Daniel Saelinger, Birgit Gockel, Manfred Ehresmann, Markus Jegelka, Joaquim Henrique Teles
Abstract: A process for preparing dialkyl terephalate comprising the following steps:—i) providing furan-2,5-dicarboxylate; ii) esterifying the furan-2,5-dicarboxylate with alcohol to form furan-2,5-carboxylic acid dialkyl ester; iii) reacting the furan-2,5-carboxylic acid dialkyl ester with ethylene under Diels Alder conditions, elevated temperature and pressure and in the presence of a catalyst such that dialkyl terephthalate is produced; wherein the Diels-Alder reaction is free from solvent; wherein the catalyst comprises a clay comprising metal ions and having Lewis acidity.
Type:
Grant
Filed:
March 28, 2019
Date of Patent:
February 28, 2023
Assignee:
CONOPCO, INC.
Inventors:
Simon William Breeden, James Hanley Clark, Thomas James Farmer, Duncan James MacQuarrie, Con Robert McElroy, Joseph Kolawole Ogunjobi, David William Thornthwaite
Abstract: A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M1 represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).
Abstract: Methods for the production of 2,4-dihydroxybutyrate (2,4-DHB) from erythrose and other four-carbon sugars are disclosed. The improved methods facilitate the production of 2,4-DHB that is a precursor for biorenewable and animal nutrition chemicals among others.
Abstract: A process for producing a surfactant having two head groups and a single tail group per molecule, including steps of: producing a compound of Formula (1) from ethanol and carbon disulfide; producing a compound of Formula (2) from a carboxylic acid and bromine; producing a compound of Formula (3) from the compound of Formula (2) and methanol; producing a compound of Formula (4) from the compound of Formula (1) and the compound of Formula (3); and producing a compound of Formula (5) from the compound of Formula (4) by a direct oxidation process or by a peracid oxidation process. The surfactant produced by the process has lower critical micelle concentration and enables a lower surface tension of a liquid as compared with prior surfactants with two head groups per molecule, thereby enabling the amount of surfactant required and thus the cost to be substantially reduced.
Abstract: A process for producing alkyl methacrylates, in particular methyl methacrylate (MMA), includes production of methacrolein (MAL) in a first reaction stage; direct oxidative esterification (DOE) of the methacrolein with an alcohol, preferably methanol, to afford an alkyl methacrylate in a second reaction stage; and workup of the alkyl methacrylate crude product from the second reaction stage. An optimized workup of the reactor output from the oxidative esterification of methacrolein involves minimizing the amount of employed water, the amount of employed acid, and/or the amount of aqueous waste streams, through an optimized recycling of the generated process water streams.
Type:
Grant
Filed:
September 15, 2020
Date of Patent:
January 24, 2023
Assignee:
Röhm GmbH
Inventors:
Florian Zschunke, Belaid Ait Aissa, Andreas Rühling, Gerhard Kölbl, Steffen Krill, Daniel Helmut König
Abstract: The present invention provides novel compounds (e.g., compounds of Formula I) which activate the Kv7 potassium channels. Separate aspects of the invention are directed to pharmaceutical compositions comprising said compounds and uses of the compounds to treat disorders responsive to the activation of Kv7 potassium channels.
Type:
Grant
Filed:
July 30, 2020
Date of Patent:
January 10, 2023
Assignee:
H. Lundbeck A/S
Inventors:
Mario Rottlander, Xiaofang Wang, Debasis Das, Jian Hong, Shu Hui Chen, Anette Graven Sams, Krestian Larsen
Abstract: The current invention relates to a method of isolating polyunsaturated fatty acids containing lipids from a lipids containing biomass. The method involves providing a suspension of cells with a PUFAs-containing lipid; optionally lysing the cells; concentrating the suspension; adding base equivalents to the suspension based on the total dry matter present; feeding a continuous reactor with the suspension; and separating the lipids-containing light phase from the water and cell debris-containing heavy phase.
Type:
Grant
Filed:
December 18, 2018
Date of Patent:
January 3, 2023
Assignees:
EVONIK OPERATIONS GMBH, DSM IP ASSETS B.V.
Inventors:
Martin Heining, Michael Benjamin Johnson, Jochen Lebert, Holger Pfeifer
Abstract: A tubular reactor comprises a tubular shell, an external jacket, and a gas distribution device at the top of the shell, wherein at least one group of feed nozzles are distributed uniformly on the shell, each group comprising at least one phosgene nozzle and at least one diamine nozzle; a reaction material is sprayed through the nozzles and impinges with each other in a middle impingement zone to strengthen the reaction effect, the gas distribution device is arranged at the top of the shell and the upper part of the feed nozzle, and an inert medium distributed uniformly through the gas distribution device is refracted at the top of the shell into an impingement reaction zone, so as to reduce the temperature and concentration of the reaction zone.
Abstract: The present invention relates to a process for the preparation of iloprost of formula I through new intermediates, isolation of iloprost of formula I in solid form, as well as preparation of the 16(S)-iloprost and 16(R)-iloprost isomers of formulae (S)-I and (R)-I and isolation of iloprost of formula I and 16(S)-iloprost of formula (S)-I in solid, crystalline form.
Type:
Grant
Filed:
April 16, 2019
Date of Patent:
December 27, 2022
Assignee:
CHINOIN GYÓGYSZER ÉS VEGYÉSZETI TERMÉKEK GYÁRA ZRT.
Inventors:
Imre Rozsumberszki, Zsuzsanna Kardos, Irén Hortobágyi, Tibor Szabó, Csaba Váradi, Tamás Bán
Abstract: In the embodiments, an aqueous hydrochloric acid solution and an organic solvent instead of hydrogen chloride gas and solid triphosgene instead of phosgene gas may be used in the process of preparing a diisocyanate from a diamine through a diamine hydrochloride. In addition, the embodiments provide processes for preparing a diisocyanate composition and an optical lens, which are excellent in yield and quality with mitigated environmental problems by controlling the total content of metals, cations, or anions in a diamine hydrochloride composition.
Type:
Grant
Filed:
December 2, 2020
Date of Patent:
December 6, 2022
Assignees:
SKC CO., LTD., WOORI FINE CHEM CO., LTD.
Abstract: An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound. The above object can be achieved by a method for producing a compound represented by formula (1): wherein R1 represents an organic group, RA represents hydrogen or fluorine, R4a represents hydrogen or an organic group, R4b represents hydrogen or an organic group, R5a represents hydrogen or an organic group, R5b represents hydrogen or an organic group, and R2 represents hydrogen or an organic group; R2 is optionally connected to R4a to form a ring; the method comprising step A of reacting a compound represented by formula (2): wherein X1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3): wherein X2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.
Type:
Grant
Filed:
June 20, 2019
Date of Patent:
November 8, 2022
Assignees:
DAIKIN INDUSTRIES, LTD., UNIVERSITY PUBLIC CORPORATION OSAKA
Abstract: A process for chemically recycling polyethylene terephthalate (PET) which utilizes a microwave absorber to optimize glycolytic depolymerization of PET via microwave irradiation. The method of chemically degrading PET to its reactive intermediate, bis(2-hydroxyethyl) terephthalate (BHET), is carried out by: (a) combining PET with ethylene glycol and a catalytic system comprising a catalyst and a microwave absorber to produce a heterogeneous reaction mixture; and then (b) heating by microwave irradiating the reaction mixture to a temperature sufficient to produce a reaction product comprising BHET. The BHET monomer then can be purified and re-polymerized to form new, virgin PET.
Type:
Grant
Filed:
November 3, 2020
Date of Patent:
October 25, 2022
Assignee:
The University of North Carolina at Chapel Hill
Abstract: The present invention relates generally to compositions and methods for treating neurodegenerative diseases and disorders, particularly ophthalmic diseases and disorders. Provided herein are alkoxyl derivative compounds and pharmaceutical compositions comprising these compounds. The subject compositions are useful for treating and preventing ophthalmic diseases and disorders, including age-related macular degeneration (AMD) and Stargardt's Disease.
Type:
Grant
Filed:
May 1, 2020
Date of Patent:
September 20, 2022
Assignee:
Acucela Inc.
Inventors:
Ian L. Scott, Vladimir A. Kuksa, Mark W. Orme, Thomas L. Little, Jr., Anna Gall, Feng Hong
Abstract: Process for inhibiting the undesired free-radical polymerization of acrylic acid present in a liquid phase P, wherein the acrylic acid content of P is at least 10% by weight, the liquid phase P comprises in the range from 25 to 1000 ppmw of glyoxal based on the weight of the acrylic acid present in P and the liquid phase P is admixed with furfural in an amount that results in a furfural content in the range from 25 to 1000 ppmw based on the weight of the acrylic acid present in P. Liquid phase P, wherein the acrylic acid content of P is at least 10% by weight and the liquid phase P comprises in the range from 25 to 1000 ppmw of glyoxal and in the range from 25 to 1000 ppmw of furfural in each case based on the weight of the acrylic acid present in P.
Type:
Grant
Filed:
July 16, 2019
Date of Patent:
September 20, 2022
Inventors:
Nicole Janssen, Peter Zurowski, Ulrich Hammon, Sylke Haremza