Preparation Of Furfural (i.e., Furan-2-aldehyde) Patents (Class 549/489)
  • Patent number: 11642811
    Abstract: The present disclosure provides an environment-friendly mildew prevention method for bamboo. The mildew prevention method for bamboo includes the following steps: soaking the bamboo in an acid solution to obtain a reaction system; subjecting the reaction system to a hydrolysis reaction to obtain a hydrolyzed product; and washing and drying the hydrolyzed product in sequence to obtain mildew-proof bamboo, where the acid solution is an inorganic acid solution or an organic acid solution; the inorganic acid solution has a mass concentration of 0.5-8%; the organic acid solution has a mass concentration of 2-40%. The present disclosure uses an inorganic acid solution or an organic acid solution to treat the bamboo, and reduces the content of starch in the bamboo through a hydrolysis reaction, thereby reducing a carbon source with starch as the main nutrient on which a mildew fungus depends and achieving the purpose of preventing the bamboo from mildewing.
    Type: Grant
    Filed: July 19, 2021
    Date of Patent: May 9, 2023
    Assignee: INTERNATIONAL CENTER FOR BAMBOO AND RATTAN
    Inventors: Zixuan Yu, Daochun Qin, Rong Zhang, Hankun Wang
  • Patent number: 11142510
    Abstract: The present invention discloses a system and a method for continuously preparing furfural using an acid-containing pentose solution. The system comprises a stripping reaction column, a separation unit, and a purification unit. The method comprises a stripping reaction step, a separation step, and a purification step. The system and the method of the present invention can use a liquid inorganic acid as a catalyst, has a strong catalytic capability and a low reaction temperature, and is capable of treating low concentration sugar liquids. The present invention adopts heating through directly vapor stripping to rapidly carry away a generated furfural along with the vapor while reacting a pentose, avoiding side reactions of the furfural in an acidic liquid environment. The reaction process of the present invention does not require any extracting agent, and the furfural carried away along with the vapor is easy to separate after cooling.
    Type: Grant
    Filed: June 5, 2020
    Date of Patent: October 12, 2021
    Assignee: ECO Environmental Energy Research Institute Limited
    Inventors: Bin Xu, Kam Shing Siu, Junde Lu, Connie Hiu Ying Chow
  • Patent number: 11040950
    Abstract: In a method and an apparatus furfural is recovered from a steam stream (3) which is formed in a treatment of a pretreated wood based material (1). The pretreated wood based material (1) which comprises at least carbohydrates is treated in a steam treatment stage (2) in which the steam is released. The steam stream (3) which comprises furfural is supplied out from the steam treatment stage (2). A pretreated and steam-treated wood based material (4) which comprises carbohydrates is supplied out from the steam treatment stage (2), and the steam stream (3) is treated in a recovery stage (12a, 12b) for recovering a furfural based fraction (14a,14b).
    Type: Grant
    Filed: December 22, 2017
    Date of Patent: June 22, 2021
    Assignee: UPM-KYMMENE CORPORATION
    Inventors: Juha Tamper, Jere Salminen, Mauno Miettinen, Sami Turunen, Meri Ventola, Vilho Nissinen
  • Patent number: 10829463
    Abstract: The invention relates to a process for separating furanic compounds from a feedstock additionally containing dimethoxysulfoxide (DMSO). These furanic compounds are in particular 5-hydroxymethylfurfural (5-HMF), 2,5-diformylfuran (DFF), 2,5-furanedicarboxylic acid (FDCA) or dimethyl 2,5-furandicarboxylate (DMFDCA). The process successively comprises a) bringing the feedstock into contact with water originating from step c), then b) a liquid-liquid extraction with an organic solvent followed by a back extraction c) by the water added in order to obtain an organic extract rich in furanic compounds. The extract may then be subjected to a crystallization step d) and then a filtration in order to obtain the solid furanic compound. The water-rich or solvent-rich effluents are advantageously recycled respectively to the back extraction and the extraction.
    Type: Grant
    Filed: September 10, 2018
    Date of Patent: November 10, 2020
    Assignee: IFP Energies Nouvelles
    Inventors: Marc Jacquin, Sophie Drozdz
  • Patent number: 10710954
    Abstract: A novel approach for the conversion of biomass based hemicellulose prehydrolysate to high value succinic acid has been investigated using a heterogeneous acid catalyst, Amberlyst 15 and hydrogen peroxide. A vital intermediate in this process, furfural, was oxidized in a biphasic system to produce succinic acid. Production of furfural in good yields is a limiting step in such processes for a number of reasons. Among the organic solvents evaluated, toluene was found to be an ideal solvent for furfural extraction and facilitated the conversion of furfural to succinic acid. Simultaneous extraction of furfural into the organic solvent as it is produced, increased the overall yield. It was observed that the developed method resulted in a succinic acid yield of 49% from the furfural obtained from hemicellulose prehydrolysate. It was found that 50 mg of Amberlyst 15 per mmole of furfural resulted in 100% FA conversion in less time.
    Type: Grant
    Filed: December 19, 2018
    Date of Patent: July 14, 2020
    Inventors: Sudip Kumar Rakshit, Sai Swaroop Dalli
  • Patent number: 10316011
    Abstract: The present invention relates to a process for the production of 2,5-furandicarboxylic acid (FDCA) via oxidation of 5-hydroxymethyl-2-furfural (HMF), said HMF being present in a solution in a high-boiling polar solvent and water. The process is characterized by the combination of —a first oxidation step wherein the HMF is at least partly oxidized in said solution to yield a first reaction mixture comprising at least one monoacid selected from the group consisting of -hydroxymethylfuran-2-carboxylic acid (HMFA), 5-formylfuran-2-carboxylic acid (FFCA) and, optionally, FDCA —an extraction step after the first oxidation step wherein said high-boiling polar solvent is extracted from said first reaction mixture by means of an extraction solvent, wherein said at least one monoacid remains in an aqueous phase, —a second oxidation step wherein said at least one monoacid is oxidized to FDCA.
    Type: Grant
    Filed: December 7, 2016
    Date of Patent: June 11, 2019
    Assignees: ANNIKKI GMBH, NOVOLANA GMBH
    Inventors: Gunter Tekautz, Dirk Kirschneck, Walter Linhart
  • Patent number: 10316009
    Abstract: The invention relates generally to the preparation of hydroxymethyl furfural derivatives such as 5-carboxymethyl furfural derivatives, ethers such as 5-alkoxymethyl furfural derivatives, 5-hydroxymethyl furfural, levulinic acid, levulinic acid esters, and/or formic acid, formic acid esters from sugar.
    Type: Grant
    Filed: August 19, 2016
    Date of Patent: June 11, 2019
    Assignee: GFBIOCHEMICALS IP ASSETS B.V.
    Inventors: Brian D. Mullen, Cora M. Leibig, Roger Schoonover, Arie De Rijke, Kevin Jon Bechtold
  • Patent number: 10125344
    Abstract: The apparatus includes: a pretreatment tank where biomass and a first acid solution are stirred to extract sugar components from the biomass; a hydrolysis tank where water is added to the pretreated mixture transferred from the pretreatment tank such that the concentration of the acid is reduced and the sugar components are hydrolyzed to produce an acid hydrolyzate; a first sugar-acid separation tank where the acid hydrolyzate is separated into a second acid solution and a first hydrolyzate; a second sugar-acid separation tank where the first hydrolyzate is separated into a third acid solution and a second hydrolyzate; a fermentation tank where the second hydrolyzate is fermented to produce bioenergy; and an acid solution concentration tank where a mixture of the second acid solution transferred from the first sugar-acid separation tank and the third acid solution transferred from the second sugar-acid separation tank is concentrated to a higher level for reuse.
    Type: Grant
    Filed: September 21, 2015
    Date of Patent: November 13, 2018
    Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY
    Inventors: Young Soon Um, Hong Gon Kim, Byoung Sung Ahn, Sang Deuk Lee, Chang Soo Kim, Dong Jin Suh, Kyung Min Lee
  • Patent number: 10099992
    Abstract: The invention relates to a method for separating formic acid from a reaction mixture which comprises, in addition to formic acid, a polyoxometalate ion of general formula [PMoxVyO40]n?, where 6?x?11, 1?y?6, x+y=12 and 3<n<10, where n, x and y are each integers, wherein the separation occurs by means of an extraction using a linear primary alcohol, wherein the carbon chain of the alcohol comprises 5 to 12 carbon atoms, and the reaction mixture is present in a protic solvent.
    Type: Grant
    Filed: January 18, 2016
    Date of Patent: October 16, 2018
    Assignee: OXFA GMBH
    Inventors: Jakob Albert, Andreas Bösmann, Jenny Reichert, Peter Wasserscheid
  • Patent number: 10040774
    Abstract: Processes for the preparation of furfural from a xylose containing feedstock and more particularly to an elevated temperature conversion of a xylose containing feedstock to furfural in acidic conditions are described. The described process uses a mixture of two solvents in which the humins are formed and solubilized. The described process is operated in continuous mode with no significant amounts of solid by-products formation.
    Type: Grant
    Filed: January 13, 2016
    Date of Patent: August 7, 2018
    Assignee: BASF SE
    Inventors: Sunil Sadashiv Divekar, Pramod Shankar Kumbhar, Rahul Vasantrao Bagal, Amit Madanlal Katariya
  • Patent number: 10005749
    Abstract: Methods and processes for the production of valuable organic products and alcohols from biomass material using a closed-loop process having numerous advantages over prior production methods are described. In the process, the biomass is subjected to acid-catalyzed digestion, followed by a separation of the digestion product stream into a solid product stream and a liquid product stream, the liquid product stream thereafter undergoing acid-catalyzed dehydration in the presence of an organic solvent, and thereafter separating the organic products in the organic layer from the aqueous layer. During the process, aqueous and organic fluid streams are fed back into various portions of the production process to increase the concentration of active portions and maximize product recovery.
    Type: Grant
    Filed: August 13, 2015
    Date of Patent: June 26, 2018
    Assignee: SHELL OIL COMPANY
    Inventors: Juben Nemchand Chheda, Jean Paul Andre Marie Joseph Ghislain Lange
  • Patent number: 9884834
    Abstract: A process is provided for improved levulinic acid production form biomass, wherein furfural is recovered from vapor flow from the levulinic acid production reactor. The reaction conditions can be chosen to enable good yield for both products and minimization of undesired side products.
    Type: Grant
    Filed: December 22, 2016
    Date of Patent: February 6, 2018
    Assignee: NESTE OYJ
    Inventor: Antti Pasanen
  • Patent number: 9815807
    Abstract: An object of the present invention is to provide a method for suppressing the corrosion of a reactor and reducing waste in the production of 2-furaldehyde from a sugar raw material containing a hexose as a constituent component, and another object of the invention is to provide an industrially advantageous method for producing 2-furaldehyde, which suppresses a decrease in the activity of a catalyst in a case of using an acid catalyst and provides a higher yield. The present invention relates to a method for producing 2-furaldehyde comprising heating a sugar raw material containing a hexose as a constituent component in an aprotic polar solvent in the presence of a solid acid catalyst.
    Type: Grant
    Filed: June 27, 2016
    Date of Patent: November 14, 2017
    Assignee: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Toru Okoshi, Hideto Tsuji
  • Patent number: 9802910
    Abstract: Provided is a method for preparing 5-hydroxymethyl-2-furfural using an acid catalyst in the presence of an ethylene glycol-based solvent. The method for preparing the 5-hydroxymethyl-2-furfural involves using a linear or cyclic ethylene glycol-based compound as a solvent and producing the 5-hydroxymethyl-2-furfural from fructose, in the presence of the acid catalyst, thereby reducing the dependency on petroleum in response to greenhouse gas emission regulations. Also, a high yield of the 5-hydroxymethyl-2-furfural can be obtained from fructose, and the solvent and the catalyst can be efficiently separated, collected, and reused after a reaction has completed.
    Type: Grant
    Filed: August 28, 2014
    Date of Patent: October 31, 2017
    Assignee: KOREA INSTITUTE OF INDUSTRIAL TECHNOLOGY
    Inventors: Jin Ku Cho, Sang Yong Kim, Bo Ra Kim, Seung Han Shin
  • Patent number: 9719179
    Abstract: The systems and methods disclosed herein process produced/flowback water, such as high total dissolved solids produced water, to generate high purity, high value products with little to no waste. The generated high purity, high value products include caustic soda, hydrochloric acid, and/or sodium hypochlorite. Further, the methods and systems disclosed herein generate high quality brine for electrolysis through the systematic removal of contaminants such as but not limited to suspended solids, iron, sulfides, barium, radium, strontium, calcium, magnesium, manganese, fluoride, heavy metals, organic carbon, recoverable hydrocarbons, silica, lithium, and/or nitrogen containing compounds. Further, some products generated by the systems and methods disclosed herein may be recovered and reutilized or sold for other uses, such as carbon dioxide, calcium oxide, chlorine, magnesium oxide, calcium carbonate, and/or barium sulfate.
    Type: Grant
    Filed: November 18, 2013
    Date of Patent: August 1, 2017
    Assignee: High Sierra Energy, LP
    Inventors: Mark A. Marcin, Thomas R. Sage
  • Patent number: 9708239
    Abstract: The invention provides a process to separate levulinic acid from a biomass hydrolysate said process comprising extraction using as an organic solvent a substituted benzene comprising (i) at least one OR1 group wherein R1 is H or CH3; and (ii) at least one C1-3 alkyl group, wherein each of the at least one OR1 group is ortho positioned to at least one C1-3 alkyl group. Using said substituted benzene as extraction solvent gives good extraction efficiency, the extraction can advantageously be carried out at elevated temperature, and is very suitable for subsequent distillation steps.
    Type: Grant
    Filed: April 24, 2014
    Date of Patent: July 18, 2017
    Assignee: Georgia-Pacific LLC
    Inventor: Pierre Louis Woestenborghs
  • Patent number: 9637463
    Abstract: The present disclosure provides methods to produce substituted furans (e.g., halomethylfurfural, hydroxymethylfurfural, and furfural), by acid-catalyzed conversion of biomass using a gaseous acid in a multiphase reactor, such as a fluidized bed reactor.
    Type: Grant
    Filed: July 21, 2015
    Date of Patent: May 2, 2017
    Assignee: MICROMIDAS, INC.
    Inventors: Makoto Nathanael Masuno, John Bissell, II, Ryan L. Smith, Brian Higgins, Alex B. Wood
  • Patent number: 9481626
    Abstract: Processes for producing formic acid from a carbohydrate-containing material include hydrolyzing a carbohydrate-containing material (e.g., cellulose) in the presence of a mineral acid to form an intermediate hydrolysate comprising one or more sugars, and hydrolyzing the intermediate hydrolysate to form a hydrolysate product including formic acid.
    Type: Grant
    Filed: June 30, 2014
    Date of Patent: November 1, 2016
    Assignee: Biofine Technology, LLC
    Inventor: Stephen W. Fitzpatrick
  • Patent number: 9346730
    Abstract: A process for producing furfural and levulinic acid from lignocellulose-comprising biomass is disclosed. The biomass is slurried using water and optionally an acid, subjected to hydrolysis, and then subjected to a solid/liquid separation to yield at least an aqueous fraction comprising C5 and C6 sugars and a solid fraction comprising cellulose and lignin. Furfural is obtained by adding an organic solvent to the aqueous fraction, heating at 120-220° C. for a sufficient time to form furfural, cooling, and separating an organic phase comprising at least part of the furfural from an aqueous phase. Levulinic acid is obtained by suspending the solid fraction in water and optionally an acid, heating the suspension to 140-220° C., and separating an aqueous fraction comprising the levulinic acid from a solid fraction.
    Type: Grant
    Filed: July 12, 2013
    Date of Patent: May 24, 2016
    Assignee: DSM IP ASSETS B.V.
    Inventors: Johannes Gerardus De Vries, Johannes Augustinus Kroon, Rudy Francois Maria Jozef Parton, Pierre Louis Woestenborghs, Arie De Rijke
  • Patent number: 9181209
    Abstract: Furfural is produced by mixing an aqueous feedstock solution containing C5 sugar and/or C6 sugar with a heated, high boiling, water-miscible solvent, such as sulfolane, and a soluble acid catalyst. Furfural product and water are distilled off through a multistage distillation column, leaving non-volatile solvent behind. Typical furfural yields with sulfolane as the reaction solvent are about 80% at as high as 99% conversion. Also, certain by-products (e.g., humins) solubilized in the reaction solvent can be precipitated by addition of water or aqueous feedstock solution and then removed by filtration, thereby providing a convenient and effective way of removing these undesirable byproducts from the reaction mixture.
    Type: Grant
    Filed: December 28, 2012
    Date of Patent: November 10, 2015
    Assignee: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Paul Joseph Fagan, Ronnie Ozer, Eric J. Till
  • Patent number: 9181211
    Abstract: Furfural is produced by mixing an aqueous feedstock solution containing C5 sugar and/or C6 sugar with a heated high boiling, water-miscible solvent, such as sulfolane, and a solid acid catalyst. Furfural product and water can be distilled off, leaving non-volatile solvent behind. Furfural yields of over 70% at as high as 99% conversion have been obtained with this process with sulfolane as the reaction solvent and zeolite beta as the solid acid catalyst. Also, certain by-products (e.g., humins) solubilized in the reaction solvent can be precipitated by addition of water or aqueous feedstock solution and then removed by filtration, thereby providing a convenient and effective way of removing these undesirable byproducts from the reaction mixture.
    Type: Grant
    Filed: December 28, 2012
    Date of Patent: November 10, 2015
    Assignee: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: David Richard Corbin, Paul Joseph Fagan, Ronnie Ozer, Bhuma Rajagopalan, Eric J. Till
  • Patent number: 9181210
    Abstract: Processes for making furfural and 5-hydroxymethylfurfural from sugars are provided. The processes can be carried out using a batch process or a continuous mode of operation. An aqueous sugar solution is pressurized with CO2, thereby producing carbonic acid in situ that catalyzes the dehydration reaction to produce furfural from C5 sugars and 5-methylhydroxyfurfural from C6 sugars.
    Type: Grant
    Filed: December 28, 2012
    Date of Patent: November 10, 2015
    Assignee: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Keith W Hutchenson, Michael Stephen McKinnon, Bhuma Rajagopalan
  • Patent number: 9174909
    Abstract: A method of producing levulinic acid from biomass is described. The method includes two acid treatment steps: first, treating biomass with a first aqueous acidic solution at a pH, for a time, and temperature such that at least a portion of pentosans contained within the biomass is extracted from the biomass, to yield pentosan-extracted biomass; second, treating the pentosan-extracted biomass with a second aqueous acidic solution at a pH, for a time, and a temperature, such that at least a portion of hexosans contained within the pentosan-extracted biomass are converted to levulinic acid.
    Type: Grant
    Filed: February 2, 2012
    Date of Patent: November 3, 2015
    Assignee: Wisconsin Alumni Research Foundation
    Inventor: Troy Runge
  • Patent number: 9150937
    Abstract: In an embodiment of the present disclosure, a method for preparing a sugar is provided. The method includes mixing an organic acid and a solid acid catalyst to form a mixing solution, adding a cellulosic biomass to the mixing solution to proceed to a dissolution reaction, and adding water to the mixing solution to proceed to a hydrolysis reaction to obtain a sugar.
    Type: Grant
    Filed: January 9, 2014
    Date of Patent: October 6, 2015
    Assignee: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Wei-Chun Hung, Ruey-Fu Shih, Jia-Yuan Chen, Hui-Tsung Lin, Hom-Ti Lee, Hou-Peng Wan
  • Patent number: 9126964
    Abstract: The present disclosure provides methods to produce substituted furans (e.g., halomethylfurfural, hydroxymethylfurfural, and furfural), by acid-catalyzed conversion of biomass using a gaseous acid in a multiphase reactor, such as a fluidized bed reactor.
    Type: Grant
    Filed: June 6, 2012
    Date of Patent: September 8, 2015
    Assignee: MICROMIDAS, INC.
    Inventors: Makoto N. Masuno, John Bissell, Ryan L. Smith, Brian Higgins, Alex Be. Wood
  • Patent number: 9090580
    Abstract: The invention relates to a method for preparing furfural by reacting pentose in water and in the presence of carboxylic acid and of a heterogeneous acid catalyst, the method being conducted in an aqueous solution of carboxylic acid as a reaction medium. The present invention also relates to the preparation of furfural by reaction of pentose in water and in the presence of carboxylic acid and of a heterogeneous acid catalyst. The invention also relates to an aqueous solution of carboxylic acid rich in furfural.
    Type: Grant
    Filed: August 24, 2012
    Date of Patent: July 28, 2015
    Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.), UNIVERSITE CLAUDE BERNARD LYON I
    Inventors: Nadine Essayem, Rodrigo Lopez De Souza, Franck Rataboul, Aude-Claire Doiseau
  • Patent number: 9090581
    Abstract: A carbohydrate-containing feedstock is converted in a process by contacting the feedstock in a first step with an alcohol in the presence of a first acid catalyst at a temperature below 100° C. to yield an intermediate product, and contacting at least part of the intermediate product in a second step with an alcohol in the presence of a second acid catalyst at a temperature of at least 100° C. Products of such conversion may include hydroxymethylfurfural, hydroxymethylfurfural ethers, levulinic acid, esters thereof and furfural.
    Type: Grant
    Filed: December 28, 2011
    Date of Patent: July 28, 2015
    Assignee: FURANIX TECHNOLOGIES B.V.
    Inventors: Ana Sofia Vagueiro de Sousa Dias, Gerardus Johannes Maria Gruter, Robert-Jan van Putten
  • Publication number: 20150140616
    Abstract: Processes are described for producing furfural from a mixture of pentoses and hexoses, by dehydrating and cyclizing pentoses to provide furfural using a water-soluble acid at elevated temperatures in the presence of a low-boiling, water-immiscible organic solvent, such as toluene, which is effective for extracting the furfural into an organic phase portion. In certain embodiments, a fermentation step occurs prior to the dehydration step to convert hexoses in the mixed pentoses and hexoses to ethanol while conserving pentoses therein for making furfural.
    Type: Application
    Filed: January 28, 2015
    Publication date: May 21, 2015
    Inventors: Tom Binder, Ahmad Hilaly, William Christopher Hoffman, Alexandra Sanborn
  • Patent number: 9024047
    Abstract: Furfural is obtained selectively and in good purity from non-fermentable branched sugars found in soluble waste streams of lignocellulosic biomass. In a monophasic method, stillage or syrup is contacted with water and an acid catalyst under suitable reaction conditions to convert the branched non-fermentable branched sugars to furfural. Additionally, the stillage or syrup can be treated with a water-immiscible organic solvent to form a biphasic mixture comprising an aqueous phase and an organic phase. The furfural that is produced preferentially partitions into the organic phase, from which it may be recovered.
    Type: Grant
    Filed: December 20, 2011
    Date of Patent: May 5, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: Rahul B Kasat, Subramaniam Sabesan
  • Patent number: 9012664
    Abstract: Furfural is produced by contacting a feedstock solution containing C5 sugar and/or C6 sugar with a solid acid catalyst using reactive distillation. Both high yield and high conversion are obtained, without production of insoluble char in the reaction vessel. Degradation of furfural is minimized by its low residence time in contact with the solid acid catalyst. Higher catalyst lifetime can be achieved because the catalyst is continually washed with the refluxing aqueous solution and not sitting in high-boiling byproducts like humins, which are known to be deleterious to catalyst lifetime.
    Type: Grant
    Filed: December 28, 2012
    Date of Patent: April 21, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: David Richard Corbin, Paul Joseph Fagan, Stuart B Fergusson, Keith W Hutchenson, Pranit S Metkar, Ronnie Ozer, Carmo Joseph Pereira, Bhuma Rajagopalan, Sourav Kumar Sengupta, Eric J. Till
  • Patent number: 9006471
    Abstract: The invention is directed to a process for production of furfural from pentoses and/or water-soluble pentosans, said process comprising converting said pentoses and/or water soluble pentosans in aqueous solution in a first step to furfural and in a second step feeding the aqueous solution containing furfural obtained in step one to the top of a distillation column to produce an aqueous, liquid downflow, which column is heated at the bottom part thereof, using at least one reboiler to produce an upflow steam flow, recovering a water and furfural containing vapor product stream from the top of said column, compressing said vapor flow and condensing it on the hot side of the reboiler at the bottom of said column to produce sufficient steam in said bottom part of the column to produce said upflow steam flow, and to recover an aqueous furfural containing solution as the condensate in the reboiler.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: April 14, 2015
    Assignee: Technische Universiteit Delft
    Inventors: Wiebren de Jong, Gianluca Marcotullio
  • Publication number: 20150087031
    Abstract: The present invention relates to methods of processing lignocellulosic material to obtain hemicellulose sugars, cellulose sugars, lignin, cellulose and other high-value products. Also provided are hemicellulose sugars, cellulose sugars, lignin, cellulose, and other high-value products.
    Type: Application
    Filed: May 3, 2013
    Publication date: March 26, 2015
    Inventors: Robert Jansen, Claire Gregoire, philip Travisano, Lee Madsen, Neta Matis, Yael Har-Tal, Shay Eliahu, James Alan Lawson, Noa Lapidot, Luke Burke, Aharon M. Eyal, Timothy Allen Bauer, Hagit Sade, Paul Mcwilliams, Ziv-Vladimir Belman, Bassem Hallac, Michael Zviely, Yelena Gershinksy, Adam Carden
  • Patent number: 8952186
    Abstract: The present invention relates to a method for dehydrating a carbohydrate-comprising composition.
    Type: Grant
    Filed: June 21, 2012
    Date of Patent: February 10, 2015
    Assignee: BASF SE
    Inventors: Alois Kindler, Klemens Massonne
  • Publication number: 20150031904
    Abstract: Provided herein is a method for producing 5-hydroxymethyl-2-furfural (HMF) from maize syrup containing fructose including a conversion step in which a reaction product containing the 5-hydroxymethyl-2-furfural is produced by mixing and heating the maize syrup, a dioxane solvent and a solid acid catalyst, thus providing an advantage that the solvent can be easily isolated and the isolated solvent can be reused because dioxane is used as the solvent, and an advantage that the catalyst can be easily isolated and the isolated catalyst can be easily reused because a nonuniform solid acid catalyst is used.
    Type: Application
    Filed: July 26, 2012
    Publication date: January 29, 2015
    Inventors: Jin Ku Cho, Jaewon Jeong, Sangyong Kim, Bora KIM, Baek-Jin Kim, Seunghan Shin, Dohoon Lee
  • Patent number: 8901325
    Abstract: A method for producing furfural from lignocellulosic biomass material is provided, comprising (a) contacting the lignocellulosic biomass material with a mixture comprising water and an organic acid at a temperature of at least 100° C. and a pressure of at most 10 bar (absolute) to obtain a first liquid stream comprising hydrolyzed hemicellulose and a second stream comprising lignin and cellulose; (b) maintaining the first liquid stream comprising hydrolyzed hemicellulose at a temperature of at least 130° C. to obtain a second liquid stream comprising furfural; and (c) separating the furfural obtained in step b) from the second liquid stream.
    Type: Grant
    Filed: December 16, 2010
    Date of Patent: December 2, 2014
    Assignee: Shell Oil Company
    Inventors: Evert Van Der Heide, Ting Zhang
  • Patent number: 8871976
    Abstract: The invention includes a compound represented by the following structural formula: wherein is described herein. The compounds of the invention are useful in staining embryonic stem cells.
    Type: Grant
    Filed: August 26, 2011
    Date of Patent: October 28, 2014
    Assignees: National University of Singapore, Agency for Science, Technology and Research
    Inventors: Young-Tae Chang, Sung Chan Lee, Nam Young Kang
  • Patent number: 8871957
    Abstract: The present invention relates to a metal catalyst composition for producing furfural derivatives from raw materials of lignocellulosic biomass, and method for producing furfural derivatives using the composition. The present invention comprises ruthenium chloride (RuCl3) and chromium chloride (CrCl2). The chromium chloride (CCl2) is from 300 to 500 parts by weight on the basis of 100 parts by weight of the ruthenium chloride (RuCl3). Unlike conventional furfural derivatives producing process that should go through multi step processes such as pre-process, saccharification process, etc, the present invention has an advantage of producing furfural derivatives from lignocellulosic raw material only through simple reaction process in one reaction apparatus by mixing various kinds of metal catalyst at an optimum ratio.
    Type: Grant
    Filed: April 14, 2011
    Date of Patent: October 28, 2014
    Assignee: Korea Institute of Industrial Technology
    Inventors: Jin Ku Cho, Sangyong Kim, Dohoon Lee, Bora Kim, Jaewon Jeong
  • Publication number: 20140309440
    Abstract: The invention relates to a method for preparing furfural by reacting pentose in water and in the presence of carboxylic acid and of a heterogeneous acid catalyst, the method being conducted in an aqueous solution of carboxylic acid as a reaction medium. The present invention also relates to the preparation of furfural by reaction of pentose in water and in the presence of carboxylic acid and of a heterogeneous acid catalyst. The invention also relates to an aqueous solution of carboxylic acid rich in furfural.
    Type: Application
    Filed: August 24, 2012
    Publication date: October 16, 2014
    Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S), Université Claude Bernard Lyon 1
    Inventors: Nadine Essayem, Rodrigo Lopez De Souza, Franck Rataboul, Aude-Claire Doiseau
  • Publication number: 20140288298
    Abstract: The present invention provides a method for efficiently producing monosaccharides, oligosaccharides, and furfurals from biomass. A biomass is hydrolyzed under conditions under which monosaccharides, oligosaccharides, and furfurals are produced while continuously supplying an aqueous suspension of the biomass from a supply port of a continuous primary hydrolysis device and moving the suspension through the device. A hydrolysis solution is continuously discharged from a discharge port of the continuous hydrolysis device, and a hydrolysis solution containing monosaccharides, oligosaccharides, and furfurals are extracted from an intermediate extraction port provided at any position between the supply port and the discharge port of the continuous primary hydrolysis device. The extracted hydrolysis solution is then subjected to secondary hydrolysis.
    Type: Application
    Filed: November 2, 2012
    Publication date: September 25, 2014
    Applicant: Oji Holdings Corporation
    Inventors: Seiji Nakagame, Nobuhisa Dano, Takayuki Obuchi, Shinya Hagiwara, Yosuke Uchida, Koki Kisara, Tomoaki Sasaki
  • Publication number: 20140228579
    Abstract: The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pri3P)Ru(NCMe)2]+[PF6]?.
    Type: Application
    Filed: September 11, 2013
    Publication date: August 14, 2014
    Applicant: Brock Unviersity
    Inventors: Georgii Nikonov, Dmitry Gutsulyak, Sun Hwa Lee
  • Patent number: 8772514
    Abstract: A method of preparing furfural compounds and a mixture for preparing the same are disclosed. First, a solution is prepared by mixing an organic ammonium salt and a hydroxyl organic solvent. Then, a carbohydrate is mixed with the solution to form a mixture. The mixture is heated to a reaction temperature for conversion of the carbohydrate to produce the furfural compounds.
    Type: Grant
    Filed: October 17, 2011
    Date of Patent: July 8, 2014
    Assignee: Industrial Technology Research Institute
    Inventors: Ruey-Fu Shih, Hsi-Yen Hsu, Jinn-Jong Wong
  • Patent number: 8772515
    Abstract: Described is a process to produce hydroxymethyl furfural (HMF) from biomass-derived sugars. The process includes the steps of reacting a C5 and/or C6 sugar-containing reactant derived from biomass in a monophasic or biphasic reaction solution comprising water and a co-solvent. The co-solvent can be beta-, gamma-, and/or delta-lactones derived from biomass, tetrahydrofuran (THF) derived from biomass, and/or methyltetrahydrofuran (MTHF) derived from biomass. The reaction takes place in the presence of an acid catalyst and a dehydration catalyst for a time and under conditions such that at least a portion of glucose or fructose present in the reactant is converted to HMF.
    Type: Grant
    Filed: October 11, 2012
    Date of Patent: July 8, 2014
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: James A. Dumesic, Jean Marcel Ribeiro Gallo, David Alonso
  • Publication number: 20140186903
    Abstract: In some variations, the invention provides a process for producing furfural, 5-hydroxymethylfurfural, and/or levulinic acid from cellulosic biomass, comprising: fractionating the feedstock in the presence of a solvent for lignin, sulfur dioxide, and water, to produce a liquor containing hemicellulose, cellulose-rich solids, and lignin; hydrolyzing the hemicellulose contained in the liquor, to produce hemicellulosic monomers; dehydrating the hemicellulose to convert at least a portion of C5 hemicelluloses to furfural and to convert at least a portion of C6 hemicelluloses to 5-hydroxymethylfurfural; converting at least some of the 5-hydroxymethylfurfural to levulinic acid and formic acid; and recovering at least one of the furfural, the 5-hydroxymethylfurfural, or the levulinic acid. Other embodiments provide a process for dehydrating hemicellulose to convert oligomeric C5 hemicelluloses to furfural and to convert oligomeric C6 hemicelluloses to 5-hydroxymethylfurfural.
    Type: Application
    Filed: November 18, 2013
    Publication date: July 3, 2014
    Applicant: API Intellectual Property Holdings, LLC
    Inventors: Theodora RETSINA, Vesa PYLKKANEN, Kimberly NELSON, Ryan O'CONNOR
  • Patent number: 8764947
    Abstract: A method and system for disposal of furfural wastewater, wherein raw crop material is transported into a hydrolysis reactor after crushed and mixed with acid to be hydrolyzed to form raw furfural liquid, and then said raw furfural liquid is transported into a distillation column to be distilled, during which furfural wastewater is discharged from said distillation column. Firstly said furfural wastewater is transported into a wastewater evaporation system to be heated it into wastewater vapor which is then transported back into said hydrolysis reactor to form recycle of said furfural wastewater. Wastewater vapor residues generated therein can be utilized directly to combust in boiler, mix with acid, or prepare end product acetate. The system for disposal of furfural wastewater comprises at least a wastewater evaporation system connecting with a heat resource which is one of steam, electricity, coal, oil, gas, plant straws or wastewater vapor residues.
    Type: Grant
    Filed: November 8, 2006
    Date of Patent: July 1, 2014
    Assignee: Jinan Shengquan Group Share-Holding Co., Ltd.
    Inventors: Yilin Tang, Chengzhen Jiang, Shaofeng Gao, Dongsheng LV, Zujiang Shen, Xuanwei Suo
  • Publication number: 20140171664
    Abstract: Furfural is produced from a xylan-containing lignocellulosic feedstock which is contacted with water in the presence of an acid catalyst. Specifically, the catalyst is sulfuric acid characterized by a room temperature pH in the range of about 0.2 to about 0.6. The use of sulfuric acid in place of phosphoric lowers costs and avoids the high viscosity of very low pH phosphoric acid.
    Type: Application
    Filed: August 10, 2012
    Publication date: June 19, 2014
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Christopher Burket, Keith W. Hutchenson
  • Publication number: 20140163245
    Abstract: A process for making furfural using papermaking black liquor from the kraft pulping process as a feed material. First, the lignin is removed from the black liquor by carbonizing the black liquor to a pH below pH 10 to insolubilize the lignin, neutralize NaOH and other inorganic components of the black liquor. The next step is to treat the carbonated black liquor that contains the hemicellulose to remove the high molecular weight components. In a preferred embodiment the treatment uses multiple sequential steps. The first step of the treatment is to use ultrafiltration, centrifugation or dissolved-air floatation to separate the high molecular weight components. The second filtration is to pass the hemicellulose containing black liquor stream through a nanofilter to remove low molecular weight components. The conversion of xylans in the hemicellulose-containing mixture to furfural is accomplished using a catalytic process. The xylans are converted to pentose sugars and then converted to furfural.
    Type: Application
    Filed: April 26, 2012
    Publication date: June 12, 2014
    Inventors: Michael A. Lake, John C. Blackburn
  • Patent number: 8748638
    Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.
    Type: Grant
    Filed: July 25, 2013
    Date of Patent: June 10, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Vladimir Grushin, Leo Ernest Manzer, Walter Partenheimer
  • Publication number: 20140051873
    Abstract: Furfural is obtained selectively and in good purity from non-fermentable branched sugars found in soluble waste streams of lignocellulosic biomass. In a monophasic method, stillage or syrup is contacted with water and an acid catalyst under suitable reaction conditions to convert the branched non-fermentable branched sugars to furfural. Additionally, the stillage or syrup can be treated with a water-immiscible organic solvent to form a biphasic mixture comprising an aqueous phase and an organic phase. The furfural that is produced preferentially partitions into the organic phase, from which it may be recovered.
    Type: Application
    Filed: December 20, 2011
    Publication date: February 20, 2014
    Applicant: E I Du Pont de Nemours and Company
    Inventors: Rahul B. Kasat, Subramaniam Sabesan
  • Patent number: 8642790
    Abstract: 5-hydroxymethylfurfural of the formula II is prepared via a 5-acyloxymethylfurfural as an intermediate.
    Type: Grant
    Filed: February 15, 2008
    Date of Patent: February 4, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Dietmar Reichert, Martin Sarich, Friedhelm Merz
  • Publication number: 20140018555
    Abstract: A process for producing furfural and levulinic acid from lignocellulose-comprising biomass is disclosed. The biomass is slurried using water and optionally an acid, subjected to hydrolysis, and then subjected to a solid/liquid separation to yield at least an aqueous fraction comprising C5 and C6 sugars and a solid fraction comprising cellulose and lignin. Furfural is obtained by adding an organic solvent to the aqueous fraction, heating at 120-220° C. for a sufficient time to form furfural, cooling, and separating an organic phase comprising at least part of the furfural from an aqueous phase. Levulinic acid is obtained by suspending the solid fraction in water and optionally an acid, heating the suspension to 140-220° C., and separating an aqueous fraction comprising the levulinic acid from a solid fraction.
    Type: Application
    Filed: July 12, 2013
    Publication date: January 16, 2014
    Inventors: Johannes Gerardus De Vries, Johannes Augustinus Kroon, Rudy Francois Maria Jozef Parton, Pierre Louis Woestenborghs, Arie De Rijke