WO2005017001A1 - Dissolution method for lignocellulosic materials - Google Patents
Dissolution method for lignocellulosic materials Download PDFInfo
- Publication number
- WO2005017001A1 WO2005017001A1 PCT/FI2004/000476 FI2004000476W WO2005017001A1 WO 2005017001 A1 WO2005017001 A1 WO 2005017001A1 FI 2004000476 W FI2004000476 W FI 2004000476W WO 2005017001 A1 WO2005017001 A1 WO 2005017001A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- lignocellulosic material
- ionic liquid
- liquid solvent
- solution
- alkyl
- Prior art date
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Classifications
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- 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
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- 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
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- 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
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Definitions
- the present invention is directed to a method for dissolving wood, straw and other natural lignocellulosic materials, and to the resulting solution, as well as to methods for separating cellulose and other organic compounds, such as lignin and extractives, from the resulting solution.
- Pulp obtained from plant fiber is the raw material for the production of paper, paperboard, fiberboard, and other similarly manufactured products. In its purified form, it is a source of cellulose for rayon, cellulose esters and other cellulose derived products.
- Wood is the primary source of fiber for pulp.
- Other sources include straws, grasses and canes.
- Pulp fibers can principally be extracted from any vacular plant found in nature, also from nonwood sources such as straws and grasses, eg, rice, esparto, wheat, and sabai; canes and reeds, eg, primarily bagasses or sucar cane; several varieties of bamboo; bast fibers, eg, jute, flax, kenaf, linen, ramie, and cannabis; leaf fibers, eg, abaca or manila hemp and sisal.
- the chemical components found in wood fall into two categories: low molecular weight substances and macromolecular substances.
- the macromolecular substances account for about 90 to 99% of the wood material.
- About 65 to 75% of the macromolecular substanses consists of polysaccharides, mainly cellulose and hemicellulose, the remainder being lignin.
- Cellulose is the main component of the wood material.
- the basic structural element of the cell wall is cellulose. Lignin and hemicelluloses are distributed throughout the cell wall in an incompletely understood manner.
- the intercellular substance, which is pimarly lignin, must be softened or dissolved to free individual fibers.
- Wood also contains about 3 to 10% of extracellular, low molecular weight constituents, many of which can be extracted from the wood using neutral solvents and therefore are commonly called extractives including fats, fatty esters, terpenes, resin acids etc. (Kirk-Othmer, Encyclopedia of Chemical Technology, 1996, 4th Ed., Vol. 20, p. 493-498). Wood as a source of pulp is divided into softwoods or evergreens, which are gymnosperms, and hardwoods or broad-leaved trees, which are dicotyledon angiosperms.
- the softwood which are preferred for most pulp products because of their longer fibers, generally contain a higher (26-32% on an extractives-free basis) percentage of lignin and a lower (14-17%) percentage of hemicellulose than the hardwoods.
- the latter contain 17-26% lignin and 18-27% hemicellulose.
- Lignin is a highly branched alkylaromatic thermoplastic polymer, and is incompletely characterized.
- Pulp fibers are classified according to the method of manufacture as mechanical, chemical, chemimechanical and semichemical.
- CMP Chemithermomechanical pulp
- the most important chemical wood pulping process is the kraft or sulfate process.
- the alkaline pulping liquor or digesting solution contains about a three-to- one ratio of sodium hydroxide (NaOH) and sodium sulfide Na 2 S.
- NaOH sodium hydroxide
- Na 2 SO 4 sodium sulfide
- the alternative term, ie, the sulfate process is derived from the use of sodium sulfate, Na 2 SO 4 , as a makeup chemical in the recovery process.
- Sodium sulfate is reduced to sodium sulfide in the recovery furnace by reaction with carbon black liquor (Kirk-Othmer, Encyclopedia of Chemical Technology, 1996, 4th Ed., Vol. 20, p. 493-546).
- Crude tall oil is a dark oily liquid with 26-42% resin acids or rosin, 36-48% fatty acids, and 10-38% neutrals.
- CTO is a very important source of oleic/linoleic fatty acids and resin acids or rosin (Kirk-Othmer, Encyclopedia of Chemical Technology, 1997, 4th Ed., Vol. 23, p. 616-622).
- the present kraft pulping process yields strong cellulose fibers by digesting pinewood chips for about two hours with an aqueous mixture of sodium hydroxide and sodium sulfide at 165-175°C under pressure. After filtration of fibers, pulping black liquour must be concentrated by multistage evaporation. At this stage, the tall oil is in soap form and must be converted into CTO by neutralizing with sulfuric acid. The proceeding is then followed by fractional distillation to separate rosin, and fatty acids and purification of the fatty acid fraction.
- US 1 943 176 discloses a process for the preparation of solutions of cellulose by dissolving cellulose under heating in a liquefied N-alkylpyridinium or N-benzylpyridinium chloride salt, preferably in the presence of an anhydrous nitrogen-containing base, such as pyridine. These salts are known as ionic liquids.
- the cellulose to be dissolved is preferably in the form of regenerated cellulose or bleached cellulose or linter.
- the cellulose solutions are suitable for various chemical reactions, such as esterification.
- US 1 943 176 also suggests separating cellulose from the cellulose solution by means of suitable precipitating agents, such as water or alcohol to produce for example cellulose threads or films or masses.
- cellulose solvents are known.
- viscose rayon is prepared from cellulose xanthate utilizing carbon disulfide as both reagent and solvent.
- US 3 447 939 discloses dissolving natural or synthetic polymeric compounds, such as cellulose in a cyclic mono(N-methylamine-N-oxide), especially N-methylmorpholine-N-oxide.
- WO 03/029329 discloses a dissolution method very similar to the one disclosed in US 1 943 176.
- the main improvement resides in the application of microwave radiation to assist in dissolution.
- the cellulose to be dissolved is fibrous cellulose, wood pulp, linters, cotton balls or paper, i.e. cellulose in a highly pure form.
- the inventors of WO 03/029329 have published an article (Swatloski, R.P.; Spear S.K.; Holbrey, J.D.; Rogers, R.D. Journal of American Chemical Society, 2002, 124, p.
- molten salts is maybe the most broadly applied term for ionic compounds in the liquid state. There is a difference between molten salts and ionic liquids, however.
- Ionic liquids are salts that are liquid around room temperature (typically -100°C to 200°C, but this might even exceed 300°C) (Wassercheid, P.; Welton, T. Ionic Liquids in Synthesis 2003, WILEY-VCH, p. 1-6, 41-55 and 68-81). Therefore, the term RTIL (room temperature ionic liquids) is commonly applied for these solvents.
- RTILs are non-flammable, non-volatile and they possess high thermal stabilities.
- these solvents are organic salts or mixtures consisting of at least one organic component.
- RTILs are relatively cheap and easy to manufacture. They can also be reused after regeneration.
- ionic liquids are excellent media for utilizing microwave techniques.
- Rogers et al. published in 2002 a method for dissolution of pure cellulose fibers into ionic liquids in the microwave field (Swatloski, R.P.; Spear S.K.; Holbrey, J.D.; Rogers, R.D. Journal of American Chemical Society, 2002, 124, p. 4974-4975). Furthermore, they were able to precipitate the fibers back by mixing this fiber-containing solution with water.
- Another object of the invention is to provide a complete or substantially complete delignification of lignocellulosic materials.
- a further object is to provide a solution of lignocellulosic materials.
- the present invention is based on the surprising discovery that untreated wood, straw and other natural lignocellulosic materials can be dissolved into ionic liquids assisted with microvawes and/or pressure. Surprisingly, the trial to dissolve soft wood into an ionic liquid (BMIMCI) proved successful.
- the present invention opens new possibilities for wood processing.
- the delignification of wood or straw or other natural lignocellulosic fiber sources by dissolution accomplishes a possibility to total delignification in a single step.
- the invention makes it possible to precipitate fibers as well as other wood or straw etc. derived organic compounds from the solution. It also accomplishes the distillation and extraction of volatile wood and straw etc. composites.
- a method for dissolving lignocellulosic material comprising mixing the lignocellulosic material with an ionic liquid solvent under microwave irradiation and/or under pressure in the substantial absence of water to completely dissolve the lignocellulosic material.
- microwave irradiation is applied to assist in dissolution.
- the pressure is preferably below 2.0 MPa, more preferably below 1.0 MPa and most preferably between 0.2 MPa and 0.9 MPa.
- the dissolution of the lignocellulosic material can be carried out at a temperature between 0°C and 250°C, preferably at a temperature between 20°C and 200°C and more preferably at a temperature between 50°C and 170°C, such as between 80°C and 150°C.
- the heating can be carried out by microwave irradiation.
- the solution is agitated until complete dissolution is obtained.
- auxiliary organic solvents or co-solvents such as nitrogen- containing bases, e.g. pyridine disclosed in US 1 943 176, are necessary.
- nitrogen- containing bases e.g. pyridine disclosed in US 1 943 176
- solvents are omitted.
- the ionic liquid solvent is molten at a temperature between -100°C and 200°C, preferably at a temperature of below 170°C, and more preferably between -50°C and 120°C.
- the cation of the ionic liquid solvent in preferably a five- or six-membered heterocyclic ring optionally being fused with a benzene ring and comprising as heteroatoms one or more nitrogen, oxygen or sulfur atoms.
- the heterocyclic ring can be aromatic or saturated.
- the cation can be one of the following: Imidazolium Pyrazolium Oxazolium
- R 1 and R 2 are independently a C ⁇ -C 6 alkyl or C 2 -C 6 alkoxyalkyl group
- R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently hydrogen, a Ct-C 6 alkyl, C 2 -C 6 alkoxyalkyl or C C 6 alkoxy group.
- R 1 and R 2 are preferably both C 1 -C 4 alkyl, and R 3 -R 9 , when present, are preferably hydrogen.
- C ⁇ -C 6 alkyl includes methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, pentyl, the isomers of pentyl, hexyl and the isomers of hexyl.
- C 1 -C 6 alkoxy contains the above Ci-C ⁇ alkyl bonded to an oxygen atom.
- C 2 -C 6 alkoxyalkyl is an alkyl group substituted by an alkoxy group, the total number of carbon atoms being from two to six.
- R ⁇ 1 - R are as defined above.
- An especially preferred cation is the imidazolium cation having the formula:
- R 1 -R 5 are as defined above.
- R 3 -R 5 are preferably each hydrogen and R 1 and R 2 are independently Ci-C ⁇ alkyl or C2-C 6 alkoxyalkyl. More preferably one of R 1 and R 2 is methyl and the other is Ci-C ⁇ alkyl.
- the anion of the ionic liquid solvent can be halogen such as chloride, bromide or iodide;
- pseudohalogen such as thiocyanate or cyanate
- C ⁇ -C 6 carboxylate such as formate, acetate, propionate, butyrate, lactate, pyruvate, maleate, fumarate or oxalate;
- Ci-C ⁇ alkyl sulfonate substituted by one or more halogen atoms such as trifluoromethane sulfonate (triflate);
- halogen substituents are preferably fluoro.
- the anion of the ionic liquid solvent is preferably selected among those providing a hydrophilic ionic liquid solvent.
- Such anions include halogen, pseudohalogen or C-i-C 6 carboxylate.
- the halogen is preferably chloride, bromide or iodide, and the pseudohalogen is preferably thiocyanate or cyanate.
- the anion is preferably a halogenid, especially chloride.
- the melting point for the preferred ionic liquid solvent 1-butyl-3-methyl-imidazolium chloride is about 60°C.
- lignocellulosic material as used in this specification means a natural material containing cellulose and lignin that has not been subjected to a pulping or defibering process. Thus, chemical and mechanical pulps and the like are not included in said term.
- the lignocellulosic material is preferably native wood that has not been subjected to any chemical or mechanical pulping process. Besides wood also other native lignocellulosic materials can be used, such as straw.
- the lignocellulosic material is prior to the dissolution reduced to a desired size and form, e.g. to small chips, and, if necessary, dried.
- the phrase "in the substantial absence of water” means that not more than a few percent by weight water is present is the dissolution. Preferably, the water content is less that 1 percent by weight.
- a solution comprising dissolved lignocellulosic material in an ionic liquid solvent that is substantially free of water.
- the ionic liquid solvent and the lignocellulosic material are as defined above.
- the lignocellulosic material can be present in an amount of about 1% to 30% by weight of the solution. Preferably the amount is about 10% to 20%.
- a method for separating cellulose from a lignocellulosic material comprising mixing the lignocellulosic material with an ionic liquid solvent under microwave irradiation and/or under pressure in the substantial absence of water to completely dissolve the lignocellulosic material, thereby obtaining a solution of the lignocellulosic material, and thereafter precipitating the cellulose by adding a non-solvent for the cellulose.
- the ionic liquid solvent and the lignocellulosic material are as defined above.
- the lignin is removed from said solution before precipitating the cellulose.
- Said non-solvent is a liquid that is miscible with the ionic liquid solvent and includes water, an alcohol, a ketone, acetonitrile or an ether.
- the alcohol can for example be methanol or ethanol.
- the ketone can for example be acetone.
- the ether can for example be furan or dioxane.
- the non-solvent is preferably water, an alcohol or a ketone.
- the non-solvent can be separated from the ionic liquid solvent, for example by distilling or drying in case water is used as the non-solvent. Thereafter the ionic liquid solvent can be reused.
- a method for the delignification of a lignocellulosic material comprising mixing the lignocellulosic material with an ionic liquid solvent under microwave irradiation and/or under pressure in the substantial absence of water to completely dissolve the lignocellulosic material, thereby obtaining a solution of the lignocellulosic material, and thereafter subjecting the solution to extraction to separate lignin from the solution.
- the ionic liquid solvent and the lignocellulosic material are as defined above.
- the invention additionally provides a method for the separation of extractives or a component thereof from a lignocellulosic material comprising mixing the lignocellulosic material with an ionic liquid solvent under microwave irradiation and/or under pressure in the substantial absence of water to completely dissolve the lignocellulosic material, thereby obtaining a solution of the lignocellulosic material, and thereafter separating the extractives or a component thereof from said solution.
- the ionic liquid solvent and the lignocellulosic material are as defined above.
- Typical extractives to be separated by this method includes fats, fatty esters, terpenes and resin acids.
- the extractives or a component thereof can be separated from the solution by extraction or by distillation.
- the basic consept of the invention can be applied e.g. for
- BMIMCI ionic liquid
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- Engineering & Computer Science (AREA)
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- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Description
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002532989A CA2532989A1 (en) | 2003-08-15 | 2004-08-13 | Dissolution method for lignocellulosic materials |
BRPI0413435-4A BRPI0413435A (en) | 2003-08-15 | 2004-08-13 | dissolution method for lignocellulosic materials |
US10/568,458 US20080023162A1 (en) | 2003-08-15 | 2004-08-13 | Dissolution Method |
EP04742219A EP1654307A1 (en) | 2003-08-15 | 2004-08-13 | Dissolution method for lignocellulosic materials |
Applications Claiming Priority (2)
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FI20031156 | 2003-08-15 | ||
FI20031156A FI115835B (en) | 2003-08-15 | 2003-08-15 | leaching |
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WO2005017001A1 true WO2005017001A1 (en) | 2005-02-24 |
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PCT/FI2004/000476 WO2005017001A1 (en) | 2003-08-15 | 2004-08-13 | Dissolution method for lignocellulosic materials |
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US (1) | US20080023162A1 (en) |
EP (1) | EP1654307A1 (en) |
BR (1) | BRPI0413435A (en) |
CA (1) | CA2532989A1 (en) |
FI (1) | FI115835B (en) |
WO (1) | WO2005017001A1 (en) |
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Also Published As
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EP1654307A1 (en) | 2006-05-10 |
US20080023162A1 (en) | 2008-01-31 |
CA2532989A1 (en) | 2005-02-24 |
FI115835B (en) | 2005-07-29 |
FI20031156A (en) | 2005-02-16 |
FI20031156A0 (en) | 2003-08-15 |
BRPI0413435A (en) | 2006-10-10 |
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