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WO2021198556A1 - Extraction de produits d'extraction à partir de lignine - Google Patents

Extraction de produits d'extraction à partir de lignine Download PDF

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Publication number
WO2021198556A1
WO2021198556A1 PCT/FI2021/050217 FI2021050217W WO2021198556A1 WO 2021198556 A1 WO2021198556 A1 WO 2021198556A1 FI 2021050217 W FI2021050217 W FI 2021050217W WO 2021198556 A1 WO2021198556 A1 WO 2021198556A1
Authority
WO
WIPO (PCT)
Prior art keywords
lignin
cooking liquor
extractives
aqueous solution
range
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.)
Ceased
Application number
PCT/FI2021/050217
Other languages
English (en)
Inventor
Maija Rouhiainen
Laura Kupiainen
Sirpa Peltola
Päivi Rousu
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 WO2021198556A1 publication Critical patent/WO2021198556A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G1/00—Lignin; Lignin derivatives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
    • 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
    • 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
    • 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
    • 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
    • D21C3/00—Pulping cellulose-containing materials
    • D21C3/20—Pulping cellulose-containing materials with organic solvents or in solvent environment

Definitions

  • the present invention relates to a method of extracting extractives from a solid lignin fraction. More particularly, the invention relates to a method of ex tracting extractives from a solid lignin fraction which is derived from a dissolved lignin in a cooking liquor used in an organosolv pulping of a lignocellulosic mate rial.
  • organosolv pulping method lignin is extracted from a lignocellulosic material by using an organic solvent as a cooking liquor.
  • Lignin, hemiceliulose and extractives dissolve into the cooking liquor while cellulose is recovered as a solid fraction.
  • organic solvents including alcohols and acids and combinations thereof have been used in the organosolv pulping.
  • a cooking liquor may contain, for example, formic acid and acetic acid and water.
  • Lignin may be separated from hemiceliulose and extractives present in the cooking liquor by adding water to the cooking liquor. Addition of water pro prises a lignin precipitate which can be separated from the liquid cooking liquor.
  • An object of the present invention is to provide a method of extracting extractives from a solid lignin fraction, comprising extracting a solid lignin fraction comprising extractives with an organic solvent to provide an organic extract con taining the extractives.
  • the present invention provides a method for recovering valuable ex tractives present in a lignocellulosic material which may be appropriately em ployed in various applications, such as in medicines and in food industry.
  • the solid lignin fraction is obtained by precip itating dissolved lignin of the cooking liquor used in an organosolv pulping of a lig- nocellulosic material.
  • a lignocellulosic material suitable for organosolv pulping can be used in the invention.
  • the lignocellulosic material may be, for example, soft wood or hardwood, such as birch.
  • Herbaceous plants, such as common reed or reed canary grass pulp may also be used.
  • agricultural waste materials such as straw and bagasse, is applicable.
  • the lignocellulosic material is biomass of wheat straw, rice straw or bagasse, without limiting thereto.
  • the cooking liquor contains formic acid, acetic acid, furan compound(s) including furfural, and water.
  • the amount of formic acid of the solvent is in the range of about 30% to about 75% by weight of the solvent. In another embodiment, the amount of formic acid of the solvent is in the range of about 40% to about 55% by weight. In an embodiment, the amount of acetic acid in the solvent is in the range of about 6% to about 55% by weight of the solvent. In an embodiment, the amount of water in the organic solvent is in the range of about 13% to about 22% by weight. In an embodiment, the total amount of furan compounds of the solvent is in the range of about 0.01 to about 3% by weight.
  • the density of the organic solvent is in the range of about 1.1 g/cm 3 to about 1.2 g/cm 3 .
  • the organosolv pulping is carried out at a tempera ture range of about 105°C to about 170°C. In another embodiment, the pulping is carried out at about 120°C to about 165°C. In a further embodiment, the pulping is carried out at about 130°C to about 160°C.
  • cellulose is separated as a solid fraction from cooking liq uor while lignin, hemicellulose and extractives remain in the cooking liquor.
  • the dry matter content of the lignin-containing cooking liquor is typi cally in the range of about 0.5% to about 15%. In an embodiment, the dry matter content is in the range of about 0.5% to about 12%. In another embodiment, the dry matter content is in the range of about 9% to about 15%.
  • the lignin-containing cooking liquor is concentrated to a dry matter content of about 5% to about 85%. In an embodiment, the dry matter is in the range of 20% to about 80%. In another embodiment, the dry matter is in the range of about 50% to about 75%.
  • the concentration may be carried out in any suitable manner, such as by evaporation.
  • Dissolved lignin is precipitated by adding an aqueous solution to the lig nin-containing cooking liquor.
  • the aqueous solution is water.
  • the ratio of added aqueous solution with respect to a lignin-containing cooking liquor varies in the range of 0.01:1-4:1 parts by weight. In an embodiment, the ratio varies in the range of 0.3: 1-4:1 parts by weight. In another embodiment, the ratio varies from about 1:1 to about 1:2. In a further embodiment, the aqueous solution is added to the lignin-containing cooking liquor in equal parts by weight, i.e. 1:1. In a further embodiment, the aqueous solution is added to the lignin-con taining cooking liquor in a weight ratio of 1:2.
  • the lignin precipitate is separated from the cooking liquor.
  • the separa tion may be carried out by any convenient manner, including filtration, such as a pressure filter or a membrane filter, a separator or a centrifuge, such as a decanter centrifuge. Various combinations of the separation methods may also be employed. In an embodiment, the separation is carried out by filtration.
  • the lignin precipitate is then extracted with an organic solvent.
  • the organic solvent is acetone.
  • Wheat straw was delignified at a cooking temperature of 135°C for 35 minutes with a cooking liquor containing 51 wt-% of formic acid, the rest being acetic acid, water and furfural.
  • the density of the cooking liquor was 1.14 g/cm 3 .
  • the cooking liquor containing lignin was then filtered off from the resultant cellu lose pulp.
  • the lignin-containing cooking liquor was mixed with water in a weight ratio 1:1 whereby a solid lignin precipitate was formed.
  • the precipitated lignin was filtered off with a glass fiber filter with a pore size of 0.6 gm and left at room tem perature until dried.
  • the lignin precipitate was extracted with acetone.
  • Wheat straw was delignified at a cooking temperature of 130°C for 20 minutes with a cooking liquor containing 41 wt-% of formic acid, the rest being acetic acid, water and furfural.
  • the density of the cooking liquor was 1.125 g/cm 3 .
  • the cooking liquor containing lignin was then filtered off from the resultant cellu lose pulp.
  • the dry matter content of the cooking liquor was 15%.
  • the lignin-containing cooking liquor with a dry matter of 15% was mixed with water in a weight ratio 1:1 whereby a solid lignin precipitate was formed.
  • the precipitated lignin was separated with a separator.
  • the resultant su- pernatant was analysed by gas chromatography. The results are shown in Table 1.
  • Bagasse was delignified at a cooking temperature of 141°C for 37 minutes with a cooking liquor containing 51 wt-% of formic acid, the rest being acetic acid, water and furfural.
  • the density of the cooking liquor used for the delig- nification was 1.14 g/cm 3 .
  • the cooking liquor containing lignin was then filtered off from the resultant cellulose pulp.
  • the dry matter content of the lignin-contain ing cooking liquor was 9%.
  • the lignin-containing cooking liquor with a dry matter of 9% was mixed with water in a weight ratio 1:2 whereby a solid lignin precipitate was formed.
  • the precipitated lignin was separated with a separator.
  • the resultant supernatant was analysed by gas chromatography. The results are shown in Table 1.
  • the amounts of the extractives in Table 1 are percentages by weight. In “Ex 1, the percentage describes an amount in acetone. In Ex. 2 and Ex. 3, the per centage describes an amount in the supernatant. Table 1.
  • Table 1 shows that valuable triterpenyl compounds are selectively bound to lignin precipitate, i.e. are detected in the acetone extract derived from the lignin precipitate. Sterols and stands are partly bound to the lignin precipitate and recovered in the extract.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

L'invention concerne un procédé d'extraction de produits d'extraction d'une fraction de lignine solide, qui consiste à extraire une fraction de lignine solide comprenant des produits d'extraction avec un solvant organique pour obtenir un extrait organique contenant les produits d'extraction.
PCT/FI2021/050217 2020-03-31 2021-03-29 Extraction de produits d'extraction à partir de lignine Ceased WO2021198556A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI20205331 2020-03-31
FI20205331A FI129825B (en) 2020-03-31 2020-03-31 Extraction of extractives from lignin

Publications (1)

Publication Number Publication Date
WO2021198556A1 true WO2021198556A1 (fr) 2021-10-07

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ID=75746651

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FI2021/050217 Ceased WO2021198556A1 (fr) 2020-03-31 2021-03-29 Extraction de produits d'extraction à partir de lignine

Country Status (2)

Country Link
FI (1) FI129825B (fr)
WO (1) WO2021198556A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016033456A1 (fr) * 2014-08-29 2016-03-03 University Of Tennessee Research Foundation Procédé complet pour sélectivement séparer une biomasse lignocellulosique en constituants purifiés à un rendement élevé

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016033456A1 (fr) * 2014-08-29 2016-03-03 University Of Tennessee Research Foundation Procédé complet pour sélectivement séparer une biomasse lignocellulosique en constituants purifiés à un rendement élevé

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DEL RÍO JOSÉ C ET AL: "Lipophilic phytochemicals from sugarcane bagasse and straw", INDUSTRIAL CROPS AND PRODUCTS, ELSEVIER, NL, vol. 77, 22 October 2015 (2015-10-22), pages 992 - 1000, XP029316103, ISSN: 0926-6690, DOI: 10.1016/J.INDCROP.2015.09.064 *

Also Published As

Publication number Publication date
FI20205331A1 (en) 2021-10-01
FI129825B (en) 2022-09-15

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