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WO2025003577A1 - Procédé de production d'un produit de lignine - Google Patents

Procédé de production d'un produit de lignine Download PDF

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Publication number
WO2025003577A1
WO2025003577A1 PCT/FI2024/050364 FI2024050364W WO2025003577A1 WO 2025003577 A1 WO2025003577 A1 WO 2025003577A1 FI 2024050364 W FI2024050364 W FI 2024050364W WO 2025003577 A1 WO2025003577 A1 WO 2025003577A1
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WO
WIPO (PCT)
Prior art keywords
lignin
acid
solution
mixture
soluble
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/FI2024/050364
Other languages
English (en)
Inventor
Päivi Rousu
Maija Rouhiainen
Juha Rainer Anttila
Laura Kupiainen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chempolis Oy
Original Assignee
Chempolis Oy
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chempolis Oy filed Critical Chempolis Oy
Publication of WO2025003577A1 publication Critical patent/WO2025003577A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/005—Lignin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H8/00—Macromolecular compounds derived from lignocellulosic materials
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
    • A23K10/32—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms from hydrolysates of wood or straw
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
    • A23K10/37—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms from waste material
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
    • A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48—Furfural
    • C07D307/50—Preparation from natural products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G1/00—Lignin; Lignin derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C11/00—Regeneration of pulp liquors or effluent waste waters
    • D21C11/0007—Recovery of by-products, i.e. compounds other than those necessary for pulping, for multiple uses or not otherwise provided for

Definitions

  • the present invention relates to a method for producing a lignin product. More particularly, the invention relates to an improved method for producing a precipitated lignin product with high purity in an efficient and controlled way.
  • WO 2011/154293 Al discloses a process for separation of lignins and sugars from an extraction liquor involving concentrating the extraction liquor, mixing the concentrated liquor with water in equal parts, stirring the resultant mixture to obtain a stable suspending of the lignins in the solution, filtering the solution comprising the suspended lignins.
  • WO 2021/198555 Al discloses a method for the separation of lignin from an organic solvent, comprising multiple two-step cycles involving a first step of adding an aqueous solution to a lignin-containing organic solvent to precipitate lignin, and a second step of subjecting the resultant lignin-reduced solution to the first step of addition of an aqueous solution. Precipitated lignin is separated and recovered in each step. The multi-step addition of an aqueous solution to a lignincontaining solution provides lignin precipitates with a different molecular weight distribution.
  • WO 2019/162277 Al discloses a method of production of lignin and hemicellulose from a plant lignocellulosic material comprising contacting a plant lignocellulosic material with an extraction solution comprising acetic acid, formic acid and water to obtain a solid fraction and a liquid fraction. The liquid fraction is separated, concentrated and mixed with equal part by weight of water to provide a suspension comprising solid particle in suspension.
  • the method is based on an organosolv pulping of a lignocellulosic material in which cellulose, lignin and hemicellulose present in the lignocellulosic material are separated in two main streams, i.e., cellulosic pulp and a solution of soluble lignin and hemicellulosic sugars, by using an aqueous organic solvent as a cooking liquor.
  • the cooking liquor is acidic and includes formic acid and acetic acid, water and furfural.
  • hemicellulosic sugars and a portion of lignin are dissolved in the cooking liquor.
  • organosolv pulping means that delignification of the lignocellulosic material is performed with organic acids in an aqueous solution constituting a cooking liquor.
  • the organic acids include formic acid and acetic acid.
  • the organosolv pulping of a lignocellulosic material is thus performed in acidic conditions wherein the total content of organic acids in the cooking liquor is about 65% wt.% to about 90% wt.%.
  • the cooking liquor used in the organosolv pulping may contain a low amount alcohol (s), such as methanol and ethanol, of at most 8 wt.%. Due to the low content of alcohol in the cooking liquor, organosolv pulping in the present invention does not correspond to organosolv delignification with alcohols.
  • s such as methanol and ethanol
  • a soluble lignin-containing organic solution obtained from cooking of a lignocellulosic material with an aqueous organic solvent is described here as "a spent cooking liquor”.
  • the spent cooking liquor thus contains, e.g.., soluble lignin, hemicellulosic sugars, inorganics, proteins and extractives, and also components of original cooking liquor.
  • soluble lignin-containing organic solution and "spent cooking liquor” are interchangeable.
  • soluble lignin is precipitated from the spent cooking liquor using an aqueous solution which comprises organic acids. It was surprisingly found, firstly, that a lignin precipitate of high purity was obtained using specific precipitation conditions involving employing an aqueous organic solution comprising acids as a precipitant solution, and secondly, using a dynamic mixer in mixing the spent cooking liquor and an aqueous organic solution in a continuous manner affected the precipitated lignin product yield and properties, and thirdly, quick cooling of the lignin precipitate provided beneficial filterability of the lignin precipitate.
  • Acidic precipitant solution obtainable from the organosolv pulping process provides a lignin precipitate of high purity and diminishes need of fresh water.
  • lignin precipitate of high purity means a precipitated lignin product which contains a decreased amount of sugars, inorganics and proteins.
  • beneficial filterability means a precipitated lignin product which filtrates with an increased rate.
  • the method of the invention employs specific precipitation conditions whereby lignin filterability of a lignin precipitate is improved.
  • Significant energy savings are achieved with method of the invention by utilizing acidic process streams, and a spent cooking liquor of high dry matter content in the precipitation, while a high quality lignin product is achieved.
  • the present invention provides an efficient and economic method for producing and recovering a pure precipitated lignin product having minor amounts of impurities, such as protein, by filtration using an acidic precipitant solution and quick cooling after the precipitation.
  • the lignin precipitate of high purity ensures efficient recovery of the lignin product by filtration whereby clogging of the filter is avoided.
  • the method of the invention efficiently employs acidic process streams avoiding need for fresh water thus providing savings in energy costs.
  • An object of the present invention is to provide a method for producing a lignin product, comprising the steps of:
  • Soluble lignin-containing organic solution is originated from an organo- solv pulping method of a lignocellulosic material.
  • the soluble lignin-containing organic solution may contain a low amount of alcohol(s), such as methanol and ethanol.
  • the amount of ethanol is at most 5 wt.%.
  • the amount of methanol is at most 6 wt.%.
  • the total content of alcohol(s) in the soluble lignin-containing organic solution is at most 8 wt.%.
  • the soluble lignin-containing organic solution comprises formic acid, acetic acid, and water. In another embodiment, the soluble lignin-containing organic solution comprises formic acid, acetic acid, water and furfural.
  • the soluble lignin -containing organic solution comprises about 65 wt.% to about 90 wt.% of organic acids in total based on the liquid part (i.e., volatile components including formic acid, acetic acid, furfural, alcohol(s), water) of the soluble lignin-containing organic solution.
  • the organic acids are formic acid and acetic acid.
  • the dry matter content of the soluble lignin-containing organic solution is in the range of about 50% to about 90%. In another embodiment, the dry matter is from about 60% to about 85%. In a further embodiment, the dry matter is from about 70% to about 80%.
  • the aqueous precipitant solution comprises about 5% to about 40% of acid(s). In another embodiment, the aqueous precipitant solution comprises about 20% to about 30% of acid(s).
  • the acid(s) is(are) organic acid(s). In an embodiment, the acid is selected from formic acid, acetic acid and a mixture thereof.
  • the aqueous precipitant solution comprises an acidic process stream from organosolv pulping process of the lignocellulosic material.
  • the aqueous precipitant solution consists of an acidic process side stream from organosolv pulping process of the lignocellulosic material. Using at least partly acidic process side streams originated from organosolv pulping process in the lignin precipitation, savings in fresh water and in energy costs are achieved.
  • the aqueous precipitant solution is added to the soluble lignin-containing organic solution in a weight ratio of about 0.7:1 to about 2.5:1. In an embodi- ment, the aqueous precipitant solution is added in a weight ratio of about 1:1 to about 2:1.
  • the aqueous precipitant solution to the soluble lignin -containing organic solution provides a mixture.
  • the content of organic acids in total based on the liquid part (i.e., volatile components including formic acid, acetic acid, furfural, alcohol(s), water) of the mixture is at most 60 wt.%.
  • the total organic acid content is in the range of about 5 wt.% to about 60 wt.% based on the liquid part.
  • the temperature of the mixture of the soluble lignin-containing organic solution and the aqueous precipitant solution before cooling is in the range of 40°C to about 90°C. In an embodiment, the temperature is about 50°C to about 90°C. In an embodiment, the temperature is about 60°C to about 85°C. In another embodiment, the temperature of the mixture is in the range of about 65°C to about 80°C. It is not necessary that the temperature of the soluble lignin -containing organic solution and the aqueous precipitant solution are initially the same. The temperature of the precipitant solution may be lower than that of the soluble lignin -containing organic solution. For example, the precipitant solution and the soluble lignin-containing organic solution may have a temperature of about 60°C and about 95°C, respectively.
  • cooling of the mixture is started.
  • the mixture containing precipitated lignin is cooled to about 20°C to about 50°C.
  • cooling of the mixture is performed or about 2 sec to about 2 hours.
  • cooling of the mixture is performed within 60 minutes. Duration of cooling is dependent on the efficiency of a heat exchanger employed in the method. Shorter cooling time is achieved with a more efficient heat exchanger. Fast cooling ensures that uniform particle size of a lignin is achieved providing, in turn, enhanced filterability of the precipitated lignin product.
  • the precipitated lignin product is separated and recovered.
  • the separation is carried out by filtration.
  • the precipitated lignin product may be washed, e.g., with water to remove any residual impurities in the product.
  • the precipitated lignin product produced by the method of the invention comprises at least 50% of acid insoluble lignin determined with NREL TP-510- 42618 method (August 2012). Lignin determined by this method is also known "Klason lignin".
  • the content of the impurities including protein, acids, pentosan hemicellulose, inorganics, e.g., ash of biomass, of the precipitated lignin product produced by the method of the invention is in the range of about 2 wt.% to about 30 wt.%.
  • the invention provides a precipitated lignin product comprising at least 50% of acid insoluble lignin determined with NREL TP-510- 42618 method (March 2012). Lignin determined by this method is also known "Klason lignin”.
  • the precipitated lignin product of the invention contains about 2 wt.% to about 30 wt.% of impurities including protein, acids, pentosan hemicellulose, inorganics, e.g., ash of biomass.
  • pentosans The content of pentosans was determined according to standard "TAPP1 T223 cm-10 Pentosans in wood and pulp", wherein furfural is analysed with HPLC.
  • Wheat straw lignocellulosic material was delignified with a cooking liquor containing water, formic acid and acetic acid to provide a soluble lignin-containing spent cooking liquor.
  • the soluble lignin-containing spent cooking liquor was concentrated to a dry matter content of 57%.
  • the content of formic acid and acetic acid in total based on the liquid part of the soluble lignin-containing spent cooking liquor was 77%.
  • Table 1 shows the effect of the precipitant solutions on the purity of the precipitated lignin products. The percentages are based on weight and on dry matter of the precipitated lignin.
  • the example illustrates an effect of different cooling times on filterability of lignin precipitates.
  • Two soluble lignin-containing spent cooking liquors were tested having a different dry matter content. Pure water was used as a precipitant solution. The precipitant solution was added to the spent cooking liquors with vigorous stirring to provide mixtures. The temperature of the mixtures was 80°C. The spent cooking liquors containing precipitated lignin were cooled to a room temperature of about 22°C before filtering.
  • Precipitated lignin was filtered using a filter paper having a retention capacity of 0.6 gm.
  • Total filtration time describes the minimum time required to stop dropping of a filtrate.
  • the results of Table 2 relate to a lignin precipitation from a soluble lignin-containing spent cooking liquor having a dry matter content of 35% before lignin precipitation.
  • the precipitant solution water was added to the spent cooking liquor in a ratio of 1:1.
  • the results of Table 3 relate to a lignin precipitation from a soluble lignin-containing spent cooking liquor having a dry matter content of 79% before lignin precipitation.
  • the precipitant solution was added to the spent cooking liquor in a ratio of 1:1 and 2:1.
  • Soluble lignin-containing spent cooking liquor having a dry matter content of 79% before lignin precipitation was provided.
  • the organic acid content of the liquid part of the soluble lignin-containing spent cooking liquor was 76 wt.%.
  • An aqueous solution containing formic acid and acetic acid in total of 20% was used as a precipitant solution.
  • the precipitant solution was added to the spent cooking liquor in a ratio of 2:1 (w/w) to provide a mixture.
  • the mixture had a formic acid and acetic content in total of 25 wt.% based on the liquid part of the mixture.
  • the temperature of the mixture was 80°C. Cooling and filtration were carried out as described in reference example 2.
  • Table 5 shows fresh water and energy savings obtained by using an acidic precipitant solution in accordance with the method of the invention instead of pure water.
  • the spent cooking liquor containing soluble lignin solution used for precipitation had a dry matter content of 70% (w/w). Flow rate of the spent cooking liquor was 30.5 t/h.
  • Precipitant solution B was an acidic process stream containing at least 5% of acids and consisting of a condensate of hemicellulose filtrate produced in an organosolv pulping of a cellulosic material.
  • Precipitant solution A contained 50% (w/w) of pure water and 50% (w/w) of the acidic process stream.
  • Each precipitant solution was added to the spent cooking liquor in the ratio of 2:1. Flow rate of the precipitant solution was 61 t/h.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Food Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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Abstract

L'invention concerne un procédé de production d'un produit de lignine précipité comprenant les étapes consistant à : fournir une solution organique soluble contenant de la lignine; fournir une solution aqueuse d'agent précipitant comprenant d'environ 5 % à environ 40 % d'acide(s); ajouter la solution aqueuse d'agent précipitant à la solution organique soluble contenant de la lignine pour obtenir un mélange dont la température est comprise entre environ 40 °C et environ 90 °C; refroidir le mélange contenant un produit de lignine précipité pendant environ 2 secondes à environ 2 heures; séparer et récupérer le produit de lignine précipité à partir du mélange.
PCT/FI2024/050364 2023-06-30 2024-06-28 Procédé de production d'un produit de lignine Pending WO2025003577A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI20235772A FI20235772A1 (en) 2023-06-30 2023-06-30 Process for producing a lignin product
FI20235772 2023-06-30

Publications (1)

Publication Number Publication Date
WO2025003577A1 true WO2025003577A1 (fr) 2025-01-02

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PCT/FI2024/050364 Pending WO2025003577A1 (fr) 2023-06-30 2024-06-28 Procédé de production d'un produit de lignine
PCT/FI2024/050366 Pending WO2025003579A1 (fr) 2023-06-30 2024-06-28 Additif alimentaire pour animaux et procédé de préparation d'un additif alimentaire pour animaux

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PCT/FI2024/050366 Pending WO2025003579A1 (fr) 2023-06-30 2024-06-28 Additif alimentaire pour animaux et procédé de préparation d'un additif alimentaire pour animaux

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WO (2) WO2025003577A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2101754A1 (fr) * 1991-02-01 1992-08-02 Jairo H. Lora Cuisson de matieres lignocellulosiques et recuperation des sous-produits du procede
WO2011154293A1 (fr) 2010-06-08 2011-12-15 Compagnie Industrielle De La Matiere Vegetale - Cimv Procédé pour la séparation de lignines et de sucres d'une liqueur d'extraction
WO2019162277A1 (fr) 2018-02-20 2019-08-29 Compagnie Industrielle De La Matiere Vegetale - Cimv Procédé de production de lignine et d'hémicellulose à partir d'un matériau lignocellulosique végétal
WO2021198555A1 (fr) 2020-03-31 2021-10-07 Chempolis Oy Séparation de la lignine

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI80191C (fi) * 1988-03-30 1990-05-10 Valio Meijerien Foerfarande och konserveringsmedel foer ensilering av foder.
NO308983B1 (no) * 1998-11-09 2000-11-27 Borregaard Ind Tilsetningsmiddel til kraftfôr, anvendelse derav og kraftfôr

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2101754A1 (fr) * 1991-02-01 1992-08-02 Jairo H. Lora Cuisson de matieres lignocellulosiques et recuperation des sous-produits du procede
WO2011154293A1 (fr) 2010-06-08 2011-12-15 Compagnie Industrielle De La Matiere Vegetale - Cimv Procédé pour la séparation de lignines et de sucres d'une liqueur d'extraction
WO2019162277A1 (fr) 2018-02-20 2019-08-29 Compagnie Industrielle De La Matiere Vegetale - Cimv Procédé de production de lignine et d'hémicellulose à partir d'un matériau lignocellulosique végétal
WO2021198555A1 (fr) 2020-03-31 2021-10-07 Chempolis Oy Séparation de la lignine

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WO2025003579A1 (fr) 2025-01-02
FI20235772A1 (en) 2024-12-31

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