Abstract: The present invention relates to a method for producing vanillin, including the steps of: (A) distilling a solution containing crude vanillin and an aliphatic dicarboxylic acid dialkyl ester to obtain a vanillin solution; and (B) subjecting the vanillin solution to anti-solvent crystallization. The method for producing vanillin according to the present invention enables production of high-purity vanillin with industrially sufficient efficiency without use of a special apparatus.
Abstract: The present disclosure relates to a process for producing high-purity acrylic acid using azeotropic distillation and using water as an entrainer. This disclosure provides a process for separating acrylic acid from recovered feed streams which comprise acrylic acid and saturated organic acids including propionic acid. The resulting acrylic acid product is of sufficient purity to produce acrylate esters and high molecular weight acrylic acid polymers.
Type:
Grant
Filed:
December 15, 2017
Date of Patent:
April 6, 2021
Assignee:
Eastman Chemical Company
Inventors:
Craig Alan Hoyme, Joseph Jerome Puhr, Robert Sterling Kline
Abstract: The present disclosure relates to a process for the manufacturing of a 3-5 halopropionylhalide, wherein the process comprises the steps of: a) providing a flow reactor comprising a reaction chamber; b) providing reactants comprising: i. acrylic acid; ii. a reaction co-agent selected from the group consisting of N,N-0 disubstituted amides; and iii. a halogenating agent; and c) incorporating the reactants into the reaction chamber of the flow reactor, thereby forming a reaction product stream comprising a 3-halopropionyl-halide; wherein the molar ratio of acrylic acid to the halogenating agent is 1 to at least 5 0.8; wherein the temperature of the reaction chamber of the flow reactor is greater than 60° C.; and wherein the residence time of the reaction product stream comprising the 3-halopropionylhalide in the reaction chamber of the flow reactor is greater than 10 minutes.
Type:
Grant
Filed:
December 12, 2018
Date of Patent:
April 6, 2021
Assignee:
3M Innovative Properties Company
Inventors:
Rudolf J. Dams, Rudy W. Van Campenhout, Matthias Conradi, Marine Movsisyan, Christian Stevens
Abstract: A process for purification of a crude product stream recovered from the production of acrylic acid by an aldolisation reaction is disclosed. The product stream comprises acrylic acid, formaldehyde, water, non-condensable vapours and optionally heavy by-products. The process comprises: providing the crude product stream in the vapour phase to a first separation column operated at a temperature and pressure to form an intermediate overhead stream comprising water, formaldehyde and methanol; and passing said intermediate overhead stream to a formaldehyde separation column operated at a temperature and pressure to enable a stream having a higher formaldehyde concentration than the formaldehyde concentration in the intermediate overhead stream to be formed and recovered from at or near the bottom of the formaldehyde separation column as a formaldehyde enriched stream.
Type:
Grant
Filed:
December 20, 2017
Date of Patent:
April 6, 2021
Assignee:
Johnson Matthey Davy Technologies Limited
Inventors:
Robert Gallen, Michael William Marshall Tuck
Abstract: A method and system for producing ketones, suitable for manufacture of base oil or diesel fuel components, from a feedstock of biological origin containing fatty acids and/or fatty acid derivatives, and being at least partly in liquid form, by subjecting the feedstock to a catalytic ketonisation reaction, wherein the ketonisation reaction is carried out in a system having one or more ketonisation reactor(s) (A?, B?) each with at least one ketonisation catalyst bed (G?). The method and system for producing ketones use a gas containing CO2 produced in the ketonisation reactors as a carrier gas.
Type:
Grant
Filed:
December 17, 2018
Date of Patent:
April 6, 2021
Assignee:
NESTE OYJ
Inventors:
Jaana Kanervo, Sami Toppinen, Pekka Nurmi
Abstract: The present invention provides processes for the preparation of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and novel intermediates used therein. In some embodiments the 3, 5-Dihydroxy-4-isopropyl-trans-stilbene is prepared from (E)-2-chloro-2-isopropyl-5-styrylcyclohexane-1,3-dione. Also disclosed are crystal forms of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and pharmaceutical compositions comprising same.
Type:
Grant
Filed:
April 15, 2020
Date of Patent:
March 30, 2021
Assignee:
DERMAVANT SCIENCES GMBH
Inventors:
Ian Paul Andrews, Nicholas Calandra, Tyler Andrew Davis, Ravinder Reddy Sudini
Abstract: Method and catalyst for producing methylbenzyl alcohol from ethanol by catalytic conversion. A route and corresponding catalysts for directly producing methylbenzyl alcohols through catalytic conversion starting from ethanol, providing an important alternative route for increasing the production of aromatic oxygenates. The selectivity of the methylbenzyl alcohols is up to 60%. At the same time, the prepared catalysts have excellent stability. Moreover, this innovative reaction route produces hydrogen as co-product without CO, thus can be directly used in chemical reactions and fuel cells. In addition, the route also produces high carbon number alcohols which can be used as fuels or oil additives to partially replace petroleum-based products, thus partly reducing the dependence on petroleum.
Abstract: Provided are methods of treating a mixture, such as a hydrocarbon mixture, that includes one or more C2-C4 carbonyl containing organic compounds. The methods may include contacting a hydrocarbon mixture with an aqueous liquid including an agent. The agent may reduce the amount of one or more C2-C4 carbonyl containing organic compounds in the mixture.
Abstract: The first aspect of the present invention is intended to provide a method for producing an oxidation reaction product of the hydrocarbon or a derivative thereof efficiently using hydrocarbon or a derivative thereof as a raw material. In order to achieve the above object, the first aspect of the present invention provides a method for producing an oxidation reaction product of a hydrocarbon or a derivative thereof. The method includes the step of irradiating a reaction system with light in the presence of a raw material and a chlorine dioxide radical. The raw material is hydrocarbon or a derivative thereof, the reaction system is a reaction system containing an organic phase, and the organic phase contains the raw material and the chlorine dioxide radical. In the step of irradiating a reaction system with light, the raw material is oxidized by the light irradiation to generate an oxidation reaction product of the raw material.
Abstract: An online continuous flow production process for directly preparing organic peroxides by using hydrogen peroxide as a raw material. This production process uses hydrogen peroxide, catalyst, and an oxidation substrate as a raw material. Substrate will be turned to designated peroxides sequentially through oxidation and workup. This process is performed in a plug-and-produce integrated continuous flow reactor, and the raw materials are continuously fed to the reactor. So, specified peroxide can be continuously obtained at the outlet of the plug-and-produce integrated continuous flow reactor.
Abstract: Methods for manufacturing phenoxyethanol from a reaction of a phenolate with a monohalohydrin. The phenolate is reacted with the monohalohydrin at a reaction temperature that is less than or equal to a boiling point of a reaction mixture to produce products that include the phenoxyethanol.
Type:
Grant
Filed:
April 13, 2018
Date of Patent:
March 9, 2021
Assignee:
Bausch Health Ireland Limited
Inventors:
Elżbieta Dąbrowska-Maś, Wojciech Raś, Bartłomiej Ataman, Kazimierz Smolak, Adam Pszeniczny
Abstract: Disclosed are a process for abating 3-cyclohexenone from a feed mixture comprising 3-cylclohexenone and cyclohexanone, comprising a hydrogenation step of contacting the feed mixture with hydrogen in the presence of a hydrogenation catalyst under hydrogenation conditions to obtain a hydrogenated mixture, cyclohexanone-containing products comprising 3-cyclohexenone and/or 2-cyclohexenone at low concentrations, and compositions of matter useful for making such cyclohexanone-containing products, particularly by using such processes.
Type:
Grant
Filed:
April 24, 2018
Date of Patent:
March 9, 2021
Assignee:
ExxonMobil Chemical Patents Inc.
Inventors:
Kendele S. Galvan, Christopher L. Becker, Jörg F. W. Weber, Ashley J. Malik
Abstract: The present invention provides an efficient process for the isolation of natural crystallized thymol product derived from crude natural Monarda citriodora (Jammu Monarda) oil useful for incorporation into foods and beverages in amounts due to strong antimicrobial, antibacterial, antioxidant properties as well as for use as a preservative. The recovery of crystallized thymol product obtained is more than 72% from Hexane-Jammu Monarda oil in a ratio 1:1 under specific conditions. A method for preparing natural thymol in crystal form involves providing crude Jammu Monarda oil in a Flask and gradually reducing the temperature of the flask containing Monarda oil:Hexane in a step-wise manner, thereby producing highly pure crystals (?95.5%) within 48 h. The methods disclosed herein are suitable for pharmaceutical GMP.
Type:
Grant
Filed:
January 3, 2019
Date of Patent:
March 9, 2021
Assignee:
Council of Scientific & Industrial Research
Abstract: The present invention relates to a method for the purification of natural vanillin, comprising a step involving the stripping of a liquid flow F2 containing natural vanillin. The invention also relates to the natural vanillin that can be obtained using the method of the invention, as well as a device for purifying natural vanillin.
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 14, 2019
Date of Patent:
March 2, 2021
Assignee:
P2 Science, Inc.
Inventors:
Patrick Foley, Neil Burns, Alexandre Chapeaux, Icilio Adami, Antonio Milicia
Abstract: Systems and methods are provided for conversion of gas phase reactants including CO and H2 to C2+ products using multiple catalysts in a single reactor while reducing or minimizing deactivation of the catalysts. Separate catalysts can be used that correspond to a first catalyst, such as a catalyst for synthesis of methanol from synthesis gas, and a second catalyst, such as a catalyst for conversion of methanol to a desired C2+ product. The separate catalysts can be loaded into the reactor in distinct layers that are separated by spacer layers. The spacer layers can correspond to relatively inert particles, such as silica particles. Optionally, the spacer layer can include an adsorbent, such as boron supported on alumina or boron carbide particles. The adsorbent can be suitable for selective adsorption of the one or more reaction products (such as one or more reaction by-products), to allow for further reduction or minimization of the deactivation of the conversion catalysts.
Type:
Grant
Filed:
January 9, 2020
Date of Patent:
February 16, 2021
Assignee:
ExxonMobil Research and Engineering Company
Inventors:
Jihad M. Dakka, Michael J. Sikorsky, Aruna Ramkrishnan, Chuansheng Bai, Anita S. Lee, Preeti Kamakoti, Anjaneya S. Kovvali, Jenna L. Walp
Abstract: A catalyst system for the conversion of glycerin to allyl alcohol, the catalyst system comprising: a rhenium compound selected from rhenium dioxide, rhenium trioxide, and a combination thereof. A method of producing allyl alcohol from glycerin via the catalyst system, the method comprising exposing glycerin to a temperature of greater than 140° C. in the presence of a catalyst comprising rhenium trioxide, rhenium dioxide, or a combination thereof to produce a product comprising allyl alcohol.
Type:
Grant
Filed:
February 25, 2019
Date of Patent:
February 16, 2021
Assignee:
Lyondell Chemical Technology, L.P.
Inventors:
Xueyong Yang, Daniel F. White, Beaven S. Mandimutsira
Abstract: A continuous flow production process for preparing organic peroxides directly from alcohols or alkanes takes very safe alcohols or alkanes as starting materials, and directly reacts to obtain designated peroxides. The production process is carried out in an integrated continuous flow reactor, and a safe starting source of alcohol or alkane is continuously added at the feed inlet of the integrated continuous flow reactor, and continuously provided with a designated peroxide at the discharge port of the integrated continuous flow reactor.
Abstract: The invention relates to a pharmaceutical combination of 2-aminoethanesulfonic acid with a pharmaceutical agent such as an antihypertensive agent and the use of 2-aminoethanesulfonic acid in a method to lower the bilirubin level in the blood.
Abstract: A method including hydroformylating, with syngas, allyl alcohol in an allyl alcohol feed, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a 1,4-butanediol (BDO) product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product. A method including hydroformylating, with syngas, allyl alcohol in a feed comprising bio-allyl alcohol, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a BDO product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product.
Type:
Grant
Filed:
February 25, 2019
Date of Patent:
February 16, 2021
Assignee:
Lyondell Chemical Technology, L.P.
Inventors:
Xueyong Yang, Daniel F. White, Beaven S. Mandimutsira