Processes Utilizing An Organic Solvent Or A Compound Having Alcoholic Hydroxy Bonded Directly To An Acyclic Carbon, Or Product Thereof Patents (Class 530/507)
  • Patent number: 12129346
    Abstract: Biomass is processed in a close to equivolumetric mixture of an alcohol and water at elevated temperature, in the presence of a metal catalyst and hydrogen. During this one-pot fractionation process, the hot liquor disentangles the polymeric biomass and depolymerises lignin and hemicellulose, while the catalyst and reductive environment are essential to accumulate and target stable products at high yield (such as phenolics and polyols, respectively). The process is particularly industrially relevant because its overcomes difficult and complex separation protocols, at place in classic biorefinery technology; the process foresees simple product recuperation in one process step into the three fractions; the solid carbohydrate pulp (mainly cellulose) is retrieved upon filtration, while phase separation of n-butanol and water occurs below 125° C. The three resulting product streams provide a versatile platform for down-stream conversion towards added-value bio-based chemicals.
    Type: Grant
    Filed: June 25, 2019
    Date of Patent: October 29, 2024
    Inventors: Bert Sels, Tom Renders, Elias Cooreman, Sander Van Den Bosch
  • Patent number: 12084621
    Abstract: The present disclosure relates to a method and system for producing refined hydrocarbons from waste plastic pyrolysis oil. The method and system for producing refined hydrocarbons from waste plastic pyrolysis oil according to the embodiments of the present disclosure may minimize formation of an ammonium salt (NH4Cl) and may prevent an adhesion phenomenon of impurity particles in a reactor in a refining process of waste plastic pyrolysis oil containing impurities including chlorine and nitrogen. In addition, the method and system for producing refined hydrocarbons according to the embodiments of the present disclosure may have excellent refining efficiency and may implement a long-term operation of a process because deactivation of a catalyst used in the process is prevented, and may produce refined hydrocarbons having a low content of impurities and a low content of olefins from waste plastic pyrolysis oil.
    Type: Grant
    Filed: January 31, 2024
    Date of Patent: September 10, 2024
    Assignees: SK INNOVATION CO., LTD., SK GEO CENTRIC CO., LTD.
    Inventors: Yong Woon Kim, Seo Yeong Kang, Soo Kil Kang, Min Gyoo Park, Young Moo Park, Min Woo Shin, Jae Hwan Lee, Jin Seong Jang, Sang Hwan Jo
  • Patent number: 11884620
    Abstract: The present invention provides for a method to deconstruct a biomass: the method comprising: (a) introducing a solvent comprising a polyamine, or a mixture of polyamines, to a biomass to dissolve at least part of solid biomass in the solvent, wherein the polyamine is a Brønsted or Lewis base, and/or the polyamine is a hydrogen bond donor and/or acceptor; (b) optionally introducing an enzyme and/or a microbe to the solubilized biomass mixture such that the enzyme and/or microbe produces a sugar from the solubilized biomass mixture; (c) optionally separating the sugar from the solubilized biomass mixture; and (d) optionally separating the lignan from the solubilized biomass mixture.
    Type: Grant
    Filed: December 9, 2021
    Date of Patent: January 30, 2024
    Assignees: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA, NATIONAL TECHNOLOGY & ENGINEERING SOLUTIONS OF SANDIA, LLC
    Inventors: Ezinne Achinivu, Mood Mohan, Hemant Choudhary, Lalitendu Das, Venkataramana R. Pidatala, Harsha D. Magurudeniya, Kaixuan Huang, John M. Gladden, Blake A. Simmons
  • Patent number: 11667981
    Abstract: Processes for converting lignocellulose to feedstock and downstream products are disclosed. The processes may include acid treatment of lignocellulose to produce a fermentation feedstock. In various instances, the processes include recovery or recycling of acid, such as recovery of hydrochloric acid from concentrated and/or dilute streams. Downstream products may include acrylic acid-based products such as diapers, paper and paper-based products, ethanol, biofuels such as biodiesel and fuel additives, and detergents.
    Type: Grant
    Filed: November 20, 2020
    Date of Patent: June 6, 2023
    Assignee: VIRDIA, LLC
    Inventors: Aharon Eyal, Robert P. Jansen
  • Patent number: 11472761
    Abstract: The present invention relates to a process for the production of glycolaldehyde by thermolytic fragmentation of a carbohydrate feedstock comprising mono- and/or di-saccharide(s) and a system suitable for performing the process. The process and the system are suitable for industrial application, and the process may be performed in a continuous process.
    Type: Grant
    Filed: December 8, 2017
    Date of Patent: October 18, 2022
    Assignee: HALDOR TOPSØE A/S
    Inventors: Christian Mårup Osmundsen, Morten Boberg Larsen
  • Patent number: 11193022
    Abstract: The method for producing a resin composition of the present invention includes a step of obtaining a lignin-containing solution that contains a solubilized lignin prepared through a treatment of separating lignin in a lignin-containing solution and a solvent, and a step of adding a resin to the lignin-containing solution to thereby obtain a lignin/resin-containing solution. Also, the method for producing a resin composition of the present invention includes a step of mixing the lignin/resin-containing solution with at least one solvent selected from water and a hydrocarbon having a dipole moment of 0.25 d or less. The lignin-containing resin molded article of the present invention uses the resin composition obtained according to the production method of the present invention.
    Type: Grant
    Filed: September 4, 2017
    Date of Patent: December 7, 2021
    Assignee: IDEMITSU KOSAN CO., LTD.
    Inventors: Yoshihito Koyama, Shinobu Yamao, Masaki Okano
  • Patent number: 11091698
    Abstract: An anti-caking agent for soil includes, as effective ingredients: a lignin having a molecular weight peak, as measured by GPC molecular weight analysis using a UV detector at a wavelength of 254 nm, within the molecular weight range of 10,000 to 40,000; and a diatomaceous earth. A method of improving the growth of a plant uses the above described anti-caking agent for soil. The anti-caking agent for soil has the effect of reducing the caking of soil and improving the poor growth of a plant.
    Type: Grant
    Filed: September 25, 2018
    Date of Patent: August 17, 2021
    Assignee: Toray Industries, Inc.
    Inventors: Shigeyuki Funada, Takahiro Arai, Hiroyuki Kurihara, Katsushige Yamada
  • Patent number: 10246583
    Abstract: A reinforced polymer composite includes a polymer matrix and a strengthening agent. The strengthening agent includes highly crystalline cellulose nanocrystals (CNC) and a stabilizing agent. The crystalline cellulose nanocrystals (CNC) have dimensions of about 3 to 5 nm in width and about 100 to 300 nm in length and a density of about 1.6 g/cm3 and the stabilizing agent may be one of Boehmite nanoclay (Boe) and Cetyltrimethylammonium Bromide (CTAB) or a combination of both.
    Type: Grant
    Filed: June 3, 2015
    Date of Patent: April 2, 2019
    Inventors: Blake Teipel, Elisa Teipel, Matt Kirby, Ryan Vano
  • Patent number: 10155853
    Abstract: Provided is a method for producing a lignin degradation product that includes (1) a degradation step of degrading a raw material containing a plant biomass, in a mixed solvent of water and an aliphatic alcohol having from 4 to 10 carbon atoms, which separates into two phases at 0° C. or higher and 50° C. or lower, under the following conditions, and (2) after the degradation step, a liquid-liquid separation step of separating the lignin degradation product-containing organic phase from the solvent that has separated at the temperature for two-phase separation. The method produces a lignin degradation product at a high yield from lignin or a material containing lignin. Condition A: The concentration of the raw material to be in the mixed solvent is 1% by mass or more and 20% by mass or less. Condition B: The reaction temperature is 100° C. or higher and 350° C. or lower. Condition C: The reaction time is 0.1 hours or more and 10 hours or less.
    Type: Grant
    Filed: April 10, 2017
    Date of Patent: December 18, 2018
    Assignees: Idemitsu Kosan Co., Ltd., National University Corporation Hokkaido University
    Inventors: Satoshi Kajitani, Naonori Ryumon, Yoshihito Koyama, Takao Masuda, Teruoki Tago
  • Patent number: 10059730
    Abstract: Disclosed are lignins and lignin compositions having high purity. Also disclosed are lignins having unique structural characteristics, including less structural degradation than conventional lignins.
    Type: Grant
    Filed: March 14, 2014
    Date of Patent: August 28, 2018
    Assignee: Renmatix, Inc.
    Inventors: Ewellyn A. Capanema, Mikhail Y. Balakshin
  • Patent number: 9346904
    Abstract: The present invention provides a thermoplastic lignin polycondensate. The thermoplastic lignin polycondensate produces no fumes and odor even at a normal melt processing temperature. The melt viscosity of the thermoplastic lignin polycondensate can be measured even when heated to 200° C. or more. The thermoplastic lignin polycondensate can be prepared by selectively activating the hydroxyl reactive groups of lignin to suppress the crosslinking reaction of the hydroxyl reactive groups, which allows a linear or grafted linear growth of the lignin polycondensate.
    Type: Grant
    Filed: September 6, 2013
    Date of Patent: May 24, 2016
    Inventors: Jae-Do Nam, Dong Kwan Kim
  • Patent number: 9255188
    Abstract: Compositions comprising lignin and low levels of undesirable impurities, such as compounds containing sulfur, nitrogen, or metals, are disclosed.
    Type: Grant
    Filed: October 8, 2013
    Date of Patent: February 9, 2016
    Assignee: Renmatix, Inc.
    Inventors: Srinivas Kilambi, Kiran L. Kadam
  • Patent number: 9187512
    Abstract: A process for recovery of lignin from black liquor that contains either soluble or dispersed lignin by generating a “liquid lignin” at high yield is disclosed. Soluble lignin at a high pH is precipitated by reducing the pH of the black liquor stream by countercurrent reaction with carbon dioxide, at elevated temperature and pressure, creating a heavy lignin-rich phase and a light lignin-depleted phase. The heavy lignin-rich phase is separated and washed countercurrently with a non-sulfur containing acid, such as acetic acid, to displace metal cations from the lignin, creating a low-salt lignin, which is then formed into a low-dust, high-bulk density lignin fuel pellet. If desired, an oxidation step may be used to eliminate odor for lignins having high value green chemistry applications.
    Type: Grant
    Filed: March 29, 2012
    Date of Patent: November 17, 2015
    Inventors: Michael A. Lake, John C. Blackburn
  • Publication number: 20150141628
    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: November 10, 2014
    Publication date: May 21, 2015
    Inventors: Robert Jansen, Philip Travisano, Lee Madsen, Neta Matis, James Alan Lawson, Noa Lapidot, Aharon M. Eyal, Timothy Allen Bauer, Ziv-Vladimir Belman, Bassem Hallac, Michael Zviely
  • Publication number: 20150119560
    Abstract: A method for the preparation of lignin, characterized in that an acid is added to an alkaline alcoholic solution of lignin and the precipitated lignin is separated, and, optionally, from the filtrate alcohol is removed in order to get further lignin; as well as a method for the preparation of a concentrated alkaline, alcoholic solution of lignin by membrane filtration; the use of the lignin thus prepared; and the isolation of hydroxy cinnamic acids from the solution, from which the lignin has been separated.
    Type: Application
    Filed: December 29, 2014
    Publication date: April 30, 2015
    Applicant: ANNIKKI GMBH
    Inventors: Thomas TERS, Halim FUQAHA, Anton FRIEDL, Ewald SREBOTNIK, Florian ZIKELI, Kurt MESSNER
  • Publication number: 20150094459
    Abstract: Low transition temperature mixtures (LTTMs) or solvents are provided that can be used in methods and systems to dissolve and bydrolyze certain components from lignin-containing biomass (e.g., lignin) at mild conditions so that further degradation is prevented. The solvents, methods and systems according to the invention have various advantages over prior technology or approaches. For example, LTTMs are cheap solvents, renewable and/or non-toxic food ingredients. LTTMs dissolve lignin selectively from a lignin-containing biomass. A highly efficient (up to 90%) lignin recovery can be achieved. The recovered lignin is of higher quality. The remaining cellulose is also of higher. Much less water is needed, which means a tremendous reduction of the energy requirement in the recovery process, i.e. less energy needed for evaporating large quantities of water.
    Type: Application
    Filed: April 12, 2013
    Publication date: April 2, 2015
    Inventors: Maaike Christine Kroon, Maria Francisco Casal, Adriaan van den Bruinhorst
  • 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: 8969534
    Abstract: Described is a method to oxidize lignin or lignin sub-units. The method includes oxidation of secondary benzylic alcohol in the lignin or lignin sub-unit to a corresponding ketone in the presence of unprotected primarily aliphatic alcohol in the lignin or lignin sub-unit. The optimal catalyst system consists of HNO3 in combination with another Brønsted acid, in the absence of a metal-containing catalyst, thereby yielding a selectively oxidized lignin or lignin sub-unit. The method may be carried out in the presence or absence of additional reagents including TEMPO and TEMPO derivatives.
    Type: Grant
    Filed: February 20, 2013
    Date of Patent: March 3, 2015
    Assignee: Wisconsin Alumni Research Foundataion
    Inventors: Shannon S. Stahl, Alireza Rahimi
  • Publication number: 20150051386
    Abstract: The invention is directed to a process for the continuous acetylation of wood elements. The process particularly combines a batchwise impregnation step, with a continuous reaction step. In order to realize this, a collection step is built-in, so as to allow batches of impregnated wood elements to be fed into a reactor in a continuous manner. Very high acetylation contents can be obtained, at a level that had not been achievable before in a continuous and non-catalyzed acetylation process.
    Type: Application
    Filed: March 21, 2013
    Publication date: February 19, 2015
    Applicant: TITAN WOOD LIMITED
    Inventors: Bernardus Jozef Maria Pol, Stefan Van Dommele, Paul Bussemaker, Benjamin Painter, Gerrit Arie De Wit, Theodorus Gerardus Marinus Maria Kappen
  • Publication number: 20150051385
    Abstract: A process for production of C5 and C6 sugar enriched syrups from lignocellulosic biomass and fermentation products therefrom is described. A lignocellulosic biomass is treated with acetic acid with washing thereof with a C1-C2 acid-miscible organic solvent, (e.g., ethyl acetate). A soluble hemicellulose and lignin enriched fraction is obtained separately from a cellulose pulp enriched fraction and lignin is removed from the soluble hemicellulose fraction. The soluble hemicellulose and lignin enriched fraction is subjected to liquid/liquid separation to obtain an aqueous phase enriched in C5 sugars and C6 sugars and reduced in content of acetic acid. The syrup is suitable for fermentation. The process also produces fractions of organic-insoluble lignin, organic-soluble lignin, and acetate salts.
    Type: Application
    Filed: April 10, 2013
    Publication date: February 19, 2015
    Inventor: Thomas Binder
  • Publication number: 20150045544
    Abstract: A biomass fractionation apparatus includes a vessel having a processing chamber, an inlet configured to receive a biomass into the processing chamber, and an outlet configured to discharge processed biomass from the chamber. A bed plate is movably positioned within the processing chamber and includes a plurality of elongated fins extending outwardly therefrom in substantially parallel spaced-apart relationship. A cylindrical rotor is rotatably secured within the processing chamber in adjacent, spaced-apart relationship with the bed plate. The rotor has a plurality of elongated blades extending radially outwardly therefrom in circumferentially spaced-apart relationship. Upon rotation of the rotor, the blades are configured to accelerate a biomass within the processing chamber against the fins of the bed plate and to cause the bed plate to pulsate against the rotor.
    Type: Application
    Filed: August 8, 2014
    Publication date: February 12, 2015
    Inventor: Melvin Mitchell
  • Publication number: 20150034109
    Abstract: A process for producing lignin from one or more plants of genus Nicotiana is provided. The lignin can be derived inter alia from Nicotiana species biomass. A process such as is described in various embodiments herein also provides articles and compositions that include lignin produced from one or more plants of genus Nicotiana.
    Type: Application
    Filed: July 23, 2014
    Publication date: February 5, 2015
    Inventors: Michael Francis Dube, James E. Fay, III
  • Publication number: 20140357847
    Abstract: The method is for separation of lignin from original black liquor (BLIN) having a first precipitation phase (PR1/PR2) for precipitation of lignin by a first acidification using acidifier, CO2, at alkaline conditions, then separating a lignin cake with subsequent suspension of the lignin cake in a strong acid to leach our metals from the lignin followed by dewatering and obtaining a clean lignin product LP. The acidic liquid phase (FL1) subjected to a sulphur removal process wherein a calcium containing compound is added to the acidic liquid phase, whereby sulphur in the acidic liquid phase is reacting with the calcium compound forming solid gypsum which could be separated and bled off from the process. The remaining acidic liquid could then be returned to the recovery process without negatively affecting the sulphur balance of the mill.
    Type: Application
    Filed: June 28, 2011
    Publication date: December 4, 2014
    Inventors: Henrik Wallmo, Martin Wimby
  • Publication number: 20140271443
    Abstract: High glass transition temperature lignin derivatives and methods of making the same are disclosed herein. In addition, methods for making carbon nanofibers from the lignin derivatives is also provided. The lignin derivatives disclosed herein are suitable for electrospinning and provide increased efficiency in production of carbon nanofibers. The lignin derivatives may be obtained using the methods disclosed herein from pulping processes conducted on lignin stock material.
    Type: Application
    Filed: March 17, 2014
    Publication date: September 18, 2014
    Inventors: Darren A. Baker, Omid Hosseinaei
  • Publication number: 20140249300
    Abstract: Disclosed are methods for the benzylic oxidation of the lignin and related compounds. The methods include contacting lignin with a mixture containing manganese and iron, in the presence of oxygen to produce a carboxylic acid from lignin or a related compound. In some embodiments, the mixture includes cobalt.
    Type: Application
    Filed: September 10, 2012
    Publication date: September 4, 2014
    Applicant: University of Tennessee Research Foundation
    Inventors: Joseph J. Bozell, Sabornie Chatterjee
  • Patent number: 8822657
    Abstract: In one aspect, a process for treating woody plant material is provided, the process involving contacting the plant material with a continuous flow of an aqueous ethanol solution at elevated temperature and pressure under conditions that promote extraction of ethanol-soluble lignin from the plant material and retention of hemicellulose sugars, xylose and cellulose in the treated plant material solids. In another aspect, a process for extracting hemicellulose sugars from lignin-depleted plant material solids is provided, the process involving contacting lignin-depleted plant material with water at elevated temperature and pressure under conditions that promote extraction of hemicellulose sugars from the plant material; and recovering hemicellulose sugars from the liquid mixture.
    Type: Grant
    Filed: September 12, 2012
    Date of Patent: September 2, 2014
    Assignee: Vertichem Corporation
    Inventors: Helene Belanger, Ross L. Prestidge, Tony James Lough, James D. Watson, Jia-Long Yao, Clare Elton, Alan MacFarlane, Mohammed Mehdi Farid, John Chen
  • Publication number: 20140235838
    Abstract: Described is a method to oxidize lignin or lignin sub-units. The method includes oxidation of secondary benzylic alcohol in the lignin or lignin sub-unit to a corresponding ketone in the presence of unprotected primarily aliphatic alcohol in the lignin or lignin sub-unit. The optimal catalyst system consists of HNO3 in combination with another Brønsted acid, in the absence of a metal-containing catalyst, thereby yielding a selectively oxidized lignin or lignin sub-unit. The method may be carried out in the presence or absence of additional reagents including TEMPO and TEMPO derivatives.
    Type: Application
    Filed: February 20, 2013
    Publication date: August 21, 2014
    Applicant: Wisconsin Alumni Research Foundation
    Inventors: Shannon S. Stahl, Alireza Rahimi
  • Patent number: 8809426
    Abstract: A method for producing an APL is provided in one example embodiment and includes mixing a solvent, a catalyst, a reagent, and a HPL to create a solution, raising the temperature of the solution to a first reaction temperature, raising the temperature of the solution to a second reaction temperature, allowing reactions in the solution to occur for a predetermined amount of time, precipitating the solution to produce a precipitate, and washing, filtering, and drying the precipitate to produce the APL.
    Type: Grant
    Filed: May 10, 2013
    Date of Patent: August 19, 2014
    Assignee: Cyclewood Solutions, Inc.
    Inventors: Nhiem Cao, Kevin Oden, Wolfgang G. Glasser
  • Patent number: 8790542
    Abstract: The present invention provides for novel compositions and methods for recycling or recovering ionic liquid used in IL pretreated cellulose and/or lignocellulosic biomass (LBM).
    Type: Grant
    Filed: September 30, 2010
    Date of Patent: July 29, 2014
    Assignees: Sandia Corporation, The Regents of the University of California
    Inventors: Dean C. Dibble, Aurelia Cheng, Anthe George
  • Publication number: 20140206799
    Abstract: The present invention relates to softwood lignin derivatives having an aliphatic hydroxyl content of from about 2.5 mmol/g to about 7 mmol/g lignin, and the preparation method thereof. The lignin derivatives have a desired antioxidant activity characterized by radical scavenging index (RSI). Another aspect of the invention relates to compositions comprising the softwood lignin derivative. Another aspect of the invention relates to a use of the softwood lignin derivatives comprising incorporating the softwood lignin derivatives into polymer compositions.
    Type: Application
    Filed: February 24, 2014
    Publication date: July 24, 2014
    Applicant: Lignol Innovations Ltd.
    Inventors: Mikhail Yurevich BALAKSHIN, Alex Berlin, Humbert Thomas Dellicolli, Chadrick Adam Nathaniel Jordan Grunert, Vera Maximenko Gutman, Darwin Ortiz, Edward Kendall Pye
  • Publication number: 20140187760
    Abstract: A method of separating lignin from black liquor from a pulp mill by adjusting the pH of the black liquor is provided. Various additional steps can be used to further process the separated lignin, including washing, drying, and/or comminuting. In certain embodiments, solvents and byproducts are recycled so as to reduce waste and maintain chemical balance within a commercial lignin production facility.
    Type: Application
    Filed: December 28, 2012
    Publication date: July 3, 2014
    Applicant: WEYERHAEUSER NR COMPANY
    Inventor: Qiusheng Pu
  • Publication number: 20140163210
    Abstract: The present invention generally provides methods of improving lignin separation during biomass fractionation with an acid to release sugars and a solvent for lignin (such as ethanol). In some embodiments, a digestor is employed to fractionating a feedstock in the presence of a solvent for lignin, sulfur dioxide, and water, to produce a liquor containing hemicellulose, cellulose-rich solids, and lignin. A solid additive is added to the digestor, wherein the solid additive combines with at least a portion of the lignin. Then a mixture of lignin and the solid additive is separated from the liquor, prior to hemicellulose recovery. Optionally, a solid additive may also be introduced to a hydrolysis reactor for converting hemicellulose oligomers to monomers, to improve separation of acid-catalyzed lignin. In some embodiments, the solid additive is gypsum or a gypsum/lignin mixture.
    Type: Application
    Filed: October 29, 2013
    Publication date: June 12, 2014
    Applicant: API Intellectual Property Holdings, LLC
    Inventors: Theodora RETSINA, Vesa PYLKKANEN, Kimberly NELSON, Mark SZCZEPANIK
  • Publication number: 20140106426
    Abstract: A method for the production water insoluble reactive lignin having low sulfur content and lignosulfonates from lignocellulosic material in a batch or continuous process. Lignocellulosic material is fractionated to produce water insoluble native lignin and lignosulfonates in various ratios, while preserving the cellulose and hydrolyzed hemicelluloses using water, ethanol and sulfur dioxide.
    Type: Application
    Filed: October 8, 2013
    Publication date: April 17, 2014
    Applicant: API Intellectual Property Holdings, LLC
    Inventors: Theodora RETSINA, Vesa PYLKKANEN
  • Patent number: 8696865
    Abstract: At least one embodiment of the present inventions relates to a method of producing a softwood lignin derivative softwood lignin derivative. The method includes steps of pulping a fibrous biomass, heating the biomass, maintaining the elevated temperature for 1 minute or longer, separating the cellulosic pulp to form a lignin rich material, and recovering derivatives of native lignin wherein the derivatives have an aliphatic hydroxyl content of from about 2.5 mmol/g to about 7 mmol/g. The derivatives can have a phenolic hydroxyl content of from about 2 mmol/g to about 8 mmol/g and a normalized RSI of 10 or greater. The method can be a kraft process or a modification thereof.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: April 15, 2014
    Assignee: Lignol Innovations Ltd.
    Inventors: Mikhail Yurevich Balakshin, Alex Berlin, Humbert Thomas Dellicolli, Chadrick Adam Nathaniel Jordan Grunert, Vera Maximenko Gutman, Darwin Ortiz, Edward Kendall Pye
  • Publication number: 20140066608
    Abstract: The present invention is directed to a method to extract lignin from lignocellulosic biomass using lactic acid.
    Type: Application
    Filed: August 30, 2013
    Publication date: March 6, 2014
    Inventors: John R. Dorgan, Michael Paul Eyser, Clayton Perbix
  • Publication number: 20140046041
    Abstract: The present disclosure relates, at least in part, to compositions comprising lignocellulosic biomass and an organic solvent wherein the lignocellulosic biomass comprises 35% or greater of lignin material. The present disclosure relates, at least in part, to compositions comprising lignocellulosic biomass and an organic solvent wherein the lignocellulosic biomass comprises 50% or less of carbohydrate. In certain embodiments the present compositions may have a viscosity of 5000 cps or less.
    Type: Application
    Filed: September 16, 2013
    Publication date: February 13, 2014
    Applicant: Lignol Innovations Ltd.
    Inventors: Colin Robert SOUTH, Mikhail Yurevich BALAKSHIN, Ewellyn CAPANEMA
  • Publication number: 20130331555
    Abstract: Technology for separating lignin from alkaline solutions which arise in production of cellulose is presented. Isolated lignin can be applied, for instance, for production of carbon fibre, adhesives and binding materials, antioxidants and organic chemicals. Starting materials are non-woody plant materials, from which lignin is dissolved by sulphur free alkaline solutions at temperatures below 130° C. Lignin is precipitated by acid, and purified by hydrolyzing hemicellulose by acid or by enzymatic reactions or a combination of these. Lignin separated has a closely similar structure as lignin in plant material, and its content of functional atom groups can be controlled by changes in processing conditions.
    Type: Application
    Filed: March 6, 2012
    Publication date: December 12, 2013
    Inventors: Yrjö Mälkki, Jussi Sipilä
  • Publication number: 20130303738
    Abstract: A method for producing an APL is provided in one example embodiment and includes mixing a solvent, a catalyst, a reagent, and a HPL to create a solution, raising the temperature of the solution to a first reaction temperature, raising the temperature of the solution to a second reaction temperature, allowing reactions in the solution to occur for a predetermined amount of time, precipitating the solution to produce a precipitate, and washing, filtering, and drying the precipitate to produce the APL.
    Type: Application
    Filed: May 10, 2013
    Publication date: November 14, 2013
    Applicant: CYCLEWOOD SOLUTIONS, INC.
    Inventors: Nhiem Cao, Kevin Oden, Wolfgang G. Glasser, Bernard Robert McKellar
  • Patent number: 8580932
    Abstract: Thermostabilization of a protein where the protein contains access routes and wherein at least one amino acid in the bottleneck of the access route is mutated, includes identifying the amino acids of the bottleneck and the amino acids control exchange of the solvent between a buried protein core and surrounding environment and/or in the packing of the amino acids inside the access route. Modification of the amino acids are determined so that the packing of the amino acids inside the tunnel is improved and the access route prevents access of undesired solvent molecules to the protein core, while allowing passage of the compounds necessary at the protein core to enable the protein to perform its biological function.
    Type: Grant
    Filed: September 5, 2012
    Date of Patent: November 12, 2013
    Assignee: Masarykova Univerzita
    Inventors: Jiri Damborsky, Zbynek Prokop, Tana Koudelakova, Veronika Stepankova, Radka Chaloupkova, Eva Chovancova, Artur Wiktor Gora, Jan Brezovsky
  • Publication number: 20130255216
    Abstract: The present disclosure relates to reactive modified lignin, methods of preparing such modified lignin, and materials, such as polymer systems, incorporating the modified lignin. More specifically, the lignin can be modified by selectively masking reactive functional groups such that the material has a modulated reactivity and is thus better suited for incorporation into and/or formation of further materials, such as carbon fibers.
    Type: Application
    Filed: February 20, 2013
    Publication date: October 3, 2013
    Applicant: NORTH CAROLINA STATE UNIVERSITY
    Inventor: Dimitris S. Argyropoulos
  • Publication number: 20130253075
    Abstract: The present invention provides derivatives of native lignin having a certain aliphatic hydroxyl content. Surprisingly, it has been found that consistent and predictable antioxidant activity may be provided by selecting for derivatives of native lignin having a certain aliphatic hydroxyl content.
    Type: Application
    Filed: May 16, 2013
    Publication date: September 26, 2013
    Applicant: Lignol Innovations Ltd.
    Inventors: Mikhail Yurevich BALAKSHIN, Alex BERLIN, Humbert Thomas DELLICOLLI, Chadrick Adam Nathaniel Jordan GRUNERT, Vera Maximenko GUTMAN, Darwin ORTIZ, Edward Kendall PYE
  • Publication number: 20130252293
    Abstract: Provided is a process for producing biomass-based product from straw hemicellulose and utilizing the components thereof thoroughly. Steam-explosion and acid-hydrolysis are combined in the pre-treatment of straw in the process, thus a higher concentration of a sugar liquid can be obtained, and furfural and acetic acid can be recovered. The hemicellulose obtained by the pre-treatment can be used directly as ferment materials for producing butanol, succinic acid, butylene glycol, lactic acid, hydrogen and firedamp, which reduces the cost of these biomass-based products. The cellulose and lignin obtained by extracting the straw with an alkaline solution can produce products, such as sodium hydroxymethyl cellulose etc. In the process, all components in the straw can be utilized thoroughly and waste and pollutant will not be produced.
    Type: Application
    Filed: January 28, 2011
    Publication date: September 26, 2013
    Applicant: Institute of Process Engineering, Chinese Academy of Sciences
    Inventors: Hongzhang Chen, Lan Wang
  • Publication number: 20130232853
    Abstract: The present invention is directed generally to a method of production of biobased chemicals, biofuels, and lignin residues from lignin sources, including waste lignin. This method may allow for selectively producing biobased chemicals, biofuels, and lignin residues from lignin sources using certain processing methods. The methods for production of these biobased chemicals, biofuels, and lignin residues may be provided by chemical-induced processing, catalytic oxidative lignin depolymerisation processing, and catalytic hydroprocessing. Further, the catalytic hydroprocessing from processes including catalytic reduction processing, catalytic hydrodeoxygenation processing, and/or catalytic/dehydrogenation processing may also be used. The method described herein also provides a means in which waste from the process(es) may be reduced and/or recycled.
    Type: Application
    Filed: May 14, 2012
    Publication date: September 12, 2013
    Applicant: THESIS CHEMISTRY, LLC
    Inventors: John R. Peterson, Jignesh S. Patel, Vladimir Romakh, Benjamin M.T. Scott
  • Publication number: 20130217868
    Abstract: A method for the preparation of lignin from lignocellulosic material by pulping with alcohol, in particular with a C1-4 alcohol, water and a base, in particular NaOH, at a temperature below 100° C., in particular from 40° C. to 90° C., in particular from 50° C. to 70° C., characterized in that 3 to 12 parts of base, in particular 4 to 10 parts of base, in particular preferable 5 to 8 parts of base, are used per 100 parts of the dry lignocellulosic material to be pulped.
    Type: Application
    Filed: September 1, 2011
    Publication date: August 22, 2013
    Applicant: ANNIKKI GMBH
    Inventors: Karin Fackler, Thomas Ters, Ortwin Ertl, Kurt Messner
  • Publication number: 20130217869
    Abstract: A method for the preparation of lignin, characterized in that an acid is added to an alkaline alcoholic solution of lignin and the precipitated lignin is separated, and, optionally, from the filtrate alcohol is removed in order to get further lignin; as well as a method for the preparation of a concentrated alkaline, alcoholic solution of lignin by membrane filtration; the use of the lignin thus prepared; and the isolation of hydroxy cinnamic acids from the solution, from which the lignin has been separated.
    Type: Application
    Filed: October 28, 2011
    Publication date: August 22, 2013
    Applicant: ANNIKKI GMBH
    Inventors: Thomas Ters, Halim Fuqaha, Anton Friedl, Ewald Srebotnik, Florian Zikeli, Kurt Messner
  • Patent number: 8383784
    Abstract: A thermoplastic material made from lignin, polyol and a melting point reducer where the melting point reducer is miscible in the specific polyol employed and where the lignin, polyol and melting point reducer are all miscible when in their melted state.
    Type: Grant
    Filed: August 31, 2009
    Date of Patent: February 26, 2013
    Assignee: Weyerhaeuser NR Company
    Inventors: David W. Park, Amar N. Neogi, Ludwig Furtner, Jr.
  • Publication number: 20130012610
    Abstract: Lignin polymers having distinctive properties, including a generally high molecular weight and generally homogeneous size distribution, as well as preservation of native reactive side groups, are isolated by solvent extraction of plant materials. Methods for isolation of lignin polymers, and for use of the isolated lignin polymers are disclosed. Compositions containing lignin isolated from plant materials, such as carbon fiber composites, resins, adhesive binders and coatings, polyurethane-based foams, rubbers and elastomers, plastics, films, paints, nutritional supplements, food and beverage additives are disclosed. Xylose and xylose derivatives, furfural, fermentable sugars, cellulose and hemi-cellulose products may be used directly or further processed. The lignin polymers and other plant-derived products disclosed herein may be produced in abundance at low cost, and may be used as substitutes for feedstocks originating from fossil fuel or petrochemical sources in the manufacture of various products.
    Type: Application
    Filed: September 11, 2012
    Publication date: January 10, 2013
    Applicant: VERTICHEM CORPORATION
    Inventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON
  • Publication number: 20130005952
    Abstract: In one aspect, a process for treating woody plant material is provided, the process involving contacting the plant material with a continuous flow of an aqueous ethanol solution at elevated temperature and pressure under conditions that promote extraction of ethanol-soluble lignin from the plant material and retention of hemicellulose sugars, xylose and cellulose in the treated plant material solids. In another aspect, a process for extracting hemicellulose sugars from lignin-depleted plant material solids is provided, the process involving contacting lignin-depleted plant material with water at elevated temperature and pressure under conditions that promote extraction of hemicellulose sugars from the plant material; and recovering hemicellulose sugars from the liquid mixture.
    Type: Application
    Filed: September 12, 2012
    Publication date: January 3, 2013
    Applicant: VERTICHEM CORPORATION
    Inventors: Helene BELANGER, Ross L. PRESTIDGE, Tony James LOUGH, James D. WATSON, Jia-Long YAO, Clare ELTON, Alan MacFARLANE, Mohammed Mehdi FARID, John CHEN
  • Publication number: 20120184721
    Abstract: The present invention provides an apparatus for separating components of a solid feedstock, in particular lignocellulosic solid biomass feedstock, and a method for using the same. The apparatus feeds the solid feedstock in one direction and provides a reaction fluid or an extraction fluid in an opposite direction of the solid feedstock to rapidly separate various components from the solid feedstock.
    Type: Application
    Filed: March 19, 2012
    Publication date: July 19, 2012
    Applicant: PUREVISION TECHNOLOGY, INC.
    Inventors: Richard C. Wingerson, Chim Yong Chin
  • Patent number: 8202970
    Abstract: A method for improving the bioavailability of polysaccharides in lignocellulosic materials, involving reacting lignocellulosic materials with ammonia and ethanol.
    Type: Grant
    Filed: August 20, 2008
    Date of Patent: June 19, 2012
    Assignee: The United States of America, as represented by the Secretary of Agriculture
    Inventors: Nhuan P. Nghiem, Tae H. Kim, Kevin B. Hicks