WO2010026244A1 - Verfahren zur integrierten herstellung von zellstoff und niedermolekularer wertstoffe - Google Patents
Verfahren zur integrierten herstellung von zellstoff und niedermolekularer wertstoffe Download PDFInfo
- Publication number
- WO2010026244A1 WO2010026244A1 PCT/EP2009/061529 EP2009061529W WO2010026244A1 WO 2010026244 A1 WO2010026244 A1 WO 2010026244A1 EP 2009061529 W EP2009061529 W EP 2009061529W WO 2010026244 A1 WO2010026244 A1 WO 2010026244A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cellulose
- fraction
- depolymerization
- lignin
- enriched
- Prior art date
Links
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- 239000000463 material Substances 0.000 title claims abstract description 54
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- 238000000034 method Methods 0.000 title claims description 171
- 239000007858 starting material Substances 0.000 claims abstract description 45
- 238000012545 processing Methods 0.000 claims abstract description 19
- 239000002609 medium Substances 0.000 claims description 118
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- 239000000203 mixture Substances 0.000 claims description 94
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- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical class CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- ITRNXVSDJBHYNJ-UHFFFAOYSA-N tungsten disulfide Chemical compound S=[W]=S ITRNXVSDJBHYNJ-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000002916 wood waste Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
- C07C37/52—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes
- C07C37/54—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms by splitting polyaromatic compounds, e.g. polyphenolalkanes by hydrolysis of lignin or sulfite waste liquor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
-
- 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
-
- 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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
Definitions
- the present invention relates to an integrated process for the production of pulp and at least one low molecular weight material, in which a lignocellulose-containing starting material is prepared and subjected to digestion with a treatment medium, from the digested material a cellulose-enriched fraction and a cellulose depleted fraction isolated and subjecting the cellulose-depleted fraction to a treatment to obtain at least one low molecular weight valuable substance.
- cellulose is the most important representative in the group of organic biopolymers and a very versatile raw material.
- biomass available as a source of raw materials however, cellulose hardly ever occurs in pure or sufficiently enriched form, but essentially as a constituent of lignocellulose.
- the digestion and fractionation of lignocellulose into its main constituents cellulose, lignin and, where appropriate, hemicellulose are central tasks of a biorefinery concept yet to be created, which should enable the effective and economical use of this renewable raw material.
- Pulp is the basis for making wood-free paper that has the property of not yellowing.
- the pulp for paper is mainly made from wood chips (wood chips), but other vegetable fibers are used.
- This group of digestion processes also includes alkaline oxygen digestion, alkali peroxide digestion, etc.
- alkaline digestion processes it has proven to be beneficial to add a small amount of anthraquinone (eg soda-anthraquinone digestion).
- the anthraquinone stabilizes the polysaccharides by suppressing their degradation from the chain end.
- various treatment media which are capable of selectively dissolve the accompanying substances of cellulose, especially the lignin, as selectively.
- Digestions with organic solvents are referred to as Organosolv method. So z.
- low-boiling alcohols methanol, ethanol
- lignin By boiling a lignocellulosic material in these alcohols, lignin can be partially hydrolyzed and solubilized. In this method, a larger part of the hemicelluloses is dissolved, so that the obtained pulps usually still contain significant amounts of lignin but little hemicelluloses.
- Organosolv processes which lead to lignin-poor pulps are in many cases designed in two stages, with one organic and one aqueous alkaline digestion medium being used in one step, eg. B. in the so-called Organocell method.
- the residual lignin can be removed in subsequent bleaching operations, e.g. B. by ozone or oxygen, only rarely with chlorine removed.
- WO 2006/031 175 describes a process for the isolation of lignin from a black liquor, in which they are acidified and dewatered to precipitate the lignin.
- No. 2,057,117 describes a process for the preparation of vanillin in which a starting material selected from lignocellulose, a crude lignin extract and lignin sulphonic acid, is heated under an elevated pressure with an aqueous alkali metal hydroxide solution and sulfuric acid is added to the resulting reaction mixture. to precipitate organic matter and convert the vanillin into a soluble form.
- US Pat. No. 2,104,701 describes a process for the preparation of vanillin which comprises heating a starting material selected from lignocellulose, a crude lignin extract and lignosulphonic acid with an aqueous alkali metal hydroxide solution under elevated pressure and from the resulting reaction mixture the lignin with a water-insoluble alcohol extracted.
- US Pat. Nos. 5,959,167 and 6,172,272 describe processes for obtaining fuel from lignin by subjecting it to base-catalyzed depolymerization in the presence of a supercritical alcohol and hydroprocessing. The products obtained are characterized by their significant content of paraffins and saturated cyclic hydrocarbon compounds.
- WO 2006/1 19357 describes a process for obtaining fuel from lignin, in which this is subjected to a base-catalyzed partial depolymerization and a hydroprocessing to obtain a biofuel.
- DE-OS-19 26 673 describes a process for the hydrolysis of a lignin material for the preparation of phenolic substances of low molecular weight.
- the lignin material comes from the alkaline digestion of lignocellulose. It is considered critical to subject the lignin to intermediate isolation and to use a base-free lignin material for depolymerization.
- No. 3,375,283 describes the preparation of methoxyphenols from wastewaters of pulp production and especially from a black liquor from the Kraft process. It is an essential feature of this process that the black liquor is first evaporated to dryness at a temperature below 150 ° C., ie below the depolymerization temperature. The dried residue is then subjected to pyrolysis at a temperature in the range of 300 to 600 0 C while circulating the pyrolysis. The pyrolysis gases are subjected to condensation, whereby a condensate enriched in methoxyphenols is obtained in addition to noncondensable gases, ie CO, CO 2, CH 3 SH and H 2 S. The gases can be burned for heat recovery or used to recover methylmercaptan. A recovery and recycling of the pulping chemicals from pulping with the goal of a closed material cycle is not described.
- a first subject of the invention is therefore an integrated process for the production of pulp and at least one low molecular weight valuable material in which
- step d) isolated from the treatment product obtained in step c) the valuable material (s).
- low molecular weight recyclables in the context of the invention comprises compounds other than pulp having a lower molecular weight than the compounds contained in the lignocellulose-containing starting material. These are z. B. selected from hydrogen and non-functionalized and functionalized aliphatic, cycloaliphatic and aromatic hydrocarbons.
- alkanes such as methane, ethane, propane, butane, etc.
- alkenes alkadienes
- alkanols such as methanol, ethanol, etc.
- aliphatic aldehydes such as formaldehyde, acetaldehyde, etc.
- cyloalkanes Cycloalkenes, cycloalkadienes, cycloalkanols, cycloalkadienols, cycloalkane polyols having more than 2 OH groups
- aromatic hydrocarbons such as benzene, alkylated benzenes, eg, toluene and xylene; more highly condensed aromatic hydrocarbons and mono-, di-, and polyalkylated higher-condensed aromatics
- aromatic alcohols such as phenols, mono-, di- and polyalkylated phenols; higher-fused aromatics having one, two or
- step e) optionally subjecting the material (s) isolated in step d) to a separation and / or at least one subsequent conversion
- step f) isolating a residue from the treatment product in step d) and subjecting it to further processing to obtain at least one component contained in the treatment medium used in step a), and
- step g) the component (s) of the treatment medium obtained in step f) is recycled in step a).
- a more specific embodiment is an integrated process for the production of pulp and an aromatic composition which comprises:
- step d) optionally subjecting the aromatics composition isolated in step d) to a separation and / or at least one subsequent reaction
- step d) in step d) from the Depolymerisations, a depleted of aromatics tene residue and subjected to further processing to obtain at least one component which is contained in the treatment medium used in step a), and
- step g) the component (s) of the treatment medium obtained in step f) is recycled in step a).
- the process for obtaining at least one valuable material is integrated into a pulping process. It is generally not necessary to isolate the components used for the treatment in step c) as an intermediate. In particular, it is not necessary to isolate the lignin as an intermediate for the preparation of an aromatic composition. As a rule, the treatment can be used to obtain at least one valuable substance in the starting material used to digest the lignocellulose-containing starting material
- Treatment medium done Specifically, the depolymerization takes place in order to obtain the aroma composition in which the lignocellulose is broken down. containing starting material containing treatment medium.
- the treatment medium used to obtain the aroma composition may contain, in addition to a liquid component, at least some of the components (process chemicals) or secondary products thereof used in the digestion of the lignocellulose-containing starting material.
- Treatment medium can be recycled after separation of the valuable substances.
- the supplementation and / or processing of the components of the treatment medium (process chemicals) consumed in the digestion of the lignocellulose-containing starting material and / or in the recovery of the valuable substances can be carried out in the existing stages of the pulping process. On the whole, it is possible to form closed product cycles with regard to the digestion chemicals used, treatment and washing media.
- the transport effort can be reduced.
- the resulting high-quality process product (aromatics) and non-inferior lignin pellets or wash liquor are transported, which have significantly greater specific volumes and weights relative to the desired product (eg phenol).
- the desired product eg phenol
- no return streams are transported to recirculate the process chemicals.
- Lignocellulose forms the structural framework of the plant cell wall and contains as its main components cellulose, lignin and hemicelluloses. Other ingredients are for. As silicates, ash (minerals), extractable low molecular weight organic compounds (so-called extractives such as terpenes, resins, fats), polymers such as proteins, nucleic acids and gum (so-called exudate), etc.
- silicates ash (minerals), extractable low molecular weight organic compounds (so-called extractives such as terpenes, resins, fats), polymers such as proteins, nucleic acids and gum (so-called exudate), etc.
- Cellulose is a generally highly crystalline biopolymer of D-anhydroglucopyranose with long chains of sugar units linked by ⁇ -1,4-glycosidic bonds.
- the individual polymer chains are interconnected by inter- and intramolecular hydrogen bonds and van der Waals interactions.
- Lignin is a high molecular weight derivative of phenylpropane and, depending on the natural source, has one or more methoxy groups on the phenyl rings and at least one hydroxy group on the propylene units.
- Typical structural units of lignin are p-hydroxyphenylpropane, guaiacylpropane and syringylpropane, which are linked together by ether bonds and carbon-carbon bonds.
- a lignocellulose-containing starting material (lignocellulosic material) is provided and subjected to digestion.
- the digestion is intended to permit at least partial separation of the lignocellulose-containing starting material into cellulose and cellulose accompanying substances.
- the cellulose impurities include lignin as well as hemicelluloses, silicates, ashes (minerals), extractable low-molecular-weight organic compounds (so-called extract substances, such as terpenes, resins, fats), polymers (proteins, nucleic acids), gum (so-called exudate), Etc.
- suitable lignocellulose-containing starting materials are, for. B. from wood and vegetable fibers available as starting material.
- Suitable lignocellulosic materials are the various types of wood, ie hardwoods such as maple, birch, pear, oak, alder, ash, eucalyptus, hornbeam, cherry, linden, walnut, poplar, willow, etc., and softwoods such as Douglas fir, spruce, yew , Hemlock, pine, larch fir, cedar, etc.
- Suitable lignocellulosic materials are still cellulosic natural fibers such as flax, hemp, sisal, jute, straw, coconut fibers, switchgrass (Panicum virgatum) and other natural fibers. Suitable lignocellulosic materials also fall, for example, as a residue in the woodworking industry. In addition to wood waste, this also includes sawdust, parquet sanding dust, etc. Suitable Lignocellulosic materials also fall as a backlog in agriculture, z. B. in the harvest of grain (wheat straw, corn straw, etc.), corn, sugar cane (bagasse), etc. Suitable lignocellulosic materials are also available as a residue in forestry, z. In the form of branches, barks, woodchips, etc. A good source of lignocellulosic materials are also short rotation crops, which enable high biomass production in a relatively small area.
- Woody wood cell wall is typically composed of Central European woods as follows: Hardwoods: 42-49% cellulose, hemicellulose 24-30%, lignin 25-30%, extractives 2-9%, ashes (minerals) 0.2-0.8%.
- Softwoods cellulose 42-51%, hemicellulose 27-40%, lignin 18-24%, extractives 1-10%, ashes 0.2-0.8%.
- lignocellulose-containing starting material may be advantageous to subject the lignocellulose-containing starting material to at least one pretreatment step prior to digestion.
- a mechanical comminution of cellulose-containing starting material eg. B. by shredding (shredding) and / or grinding. Due to their material properties, fiber-containing materials are preferably not subjected to pressure-shear comminution but to impact crushing. Suitable grinding devices are hammer mills, grinders operating on the principle of jet milling and beater wheel mills. The latter are especially suitable for high throughputs.
- the process according to the invention makes it possible to integrate the production of a valuable substance composition (for example an aroma composition) into a process for the production of cellulose.
- a valuable substance composition for example an aroma composition
- the integration succeeds in virtually all basic digestion processes.
- Suitable processes for producing pulp may, in principle, differ in at least one of the following features:
- step a the treatment medium used in step a), the treatment conditions used in step a), the components used in a further process step, the process conditions used in a further process step,
- the treatment medium used in step a) is capable of solubilizing at least part of the cellulose impurities of the lignocellulose-containing starting material under the digestion conditions specified below.
- an at least partial, preferably substantially complete, solubilization of the ligin contained in the lignocellulose-containing starting material takes place.
- This is understood to mean, preferably at least 50% by weight, especially preferably at least 75% by weight, based on the total weight of the lignin contained in the ligno-cellulose-containing starting material, are solubilized.
- the cellulose contained in the lignocellulose-containing starting material is not or only partially solubilized in the treatment medium. This is understood to mean that preferably at most 20% by weight, particularly preferably at most 10% by weight, based on the total weight of the cellulose contained in the lignocellulose-containing starting material, are solubilized.
- the term "solubilization” refers to the conversion into a liquid state and comprises the generation of solutions of the cellulase accompanying substances (especially of solutions of lignin), as well as the conversion into a different solubilized state.
- a lignocellulosic component is converted to a solubilized state, the individual molecules, e.g. B. polymer molecules, not necessarily completely surrounded by a solvation shell. It is essential that the lignocellulose component changes to a liquid state as a result of the solubilization.
- Solubilisates according to the invention are thus also colloidal solutions, microdispersions, gels, etc.
- the treatment medium used in step a) comprises at least one bar Grinding Conditions in Norway (20 0 C and 1, 01325) liquid compound.
- liquid compound This is preferably selected from water, acids, bases and organic solvents capable of at least partially solubilizing lignin without solubilizing larger amounts of cellulose.
- mixtures of these liquid compounds are also suitable.
- no mixtures of acids and base are used, but instead the corresponding salt in combination with at least one liquid compound.
- liquid acids and bases may be selected by those skilled in the art from those listed below.
- the organic solvents are preferably selected from alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol or phenol, diols and polyols, such as ethanediol and propanediol, aminoalcohols, such as ethanolamine, Diethanolamine or triethanolamine, aromatic hydrocarbons, such as benzene, toluene, ethylbenzene or xylenes, halogenated solvents, such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane or chlorobenzene, aliphatic solvents, such as pentane, hexane, heptane, octane, ligroin, petroleum ether, Cyclohexane or decalin, ethers, such as tetrahydrofuran, diethyl ether,
- the liquid compound is selected from water, water-miscible organic solvents and mixtures thereof.
- the liquid compound is selected from water, alcohols and mixtures thereof. So can as the liquid compound water, methanol, ethanol, a mixture of water with methanol and / or ethanol, or a mixture of methanol and ethanol are used.
- the treatment medium used in step a) may comprise at least one base.
- Suitable bases are alkali and alkaline earth metal hydroxides, e.g. For example, sodium hydroxide, potassium hydroxide, calcium hydroxide or magnesium hydroxide, alkali metal and alkaline earth metal hydrogen carbonates, z.
- Sodium carbonate, potassium carbonate, calcium carbonate or magnesium carbonate, alkaline earth metal oxides such as calcium oxide or magnesium oxide, and mixtures thereof.
- the treatment medium used in step a) can comprise at least one acid.
- Brönsted acids or Lewis acids are suitable.
- Suitable Brönsted acids are inorganic acids, their acid salts and anhydrides. These include, for example, mineral acids, such as hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid or amidosulfonic acid, but also ammonium salts, such as ammonium fluoride, ammonium chloride, ammonium bromide or ammonium sulfate.
- ammonium salts such as ammonium fluoride, ammonium chloride, ammonium bromide or ammonium sulfate.
- hydrogen sulfates such as sodium hydrogen sulfate, potassium hydrogen sulfate, calcium hydrogen sulfate or magnesium hydrogen sulfate.
- hydrogen sulfites such as sodium hydrogen sulfite, potassium hydrogen sulfite, calcium hydrogen sulfite or magnesium hydrogen sulfite.
- hydrogen phosphates and dihydrogen phosphates such as sodium hydrogen phosphate, sodium dihydrogen phosphate, potassium hydrogen phosphate or potassium dihydrogen phosphate.
- SO2, SO3 and CO2 are also suitable.
- Suitable Bronsted acids are also organic acids and their anhydrides, such as formic acid, acetic acid, methanesulfonic acid, trifluoroacetic acid or p-toluenesulfonic acid.
- Suitable Lewis acids are any metal or semimetallic halides in which the metal or metalloid has an electron pair gap. Examples include BF3, BCB, BBr 3, AlF 3, AlCl 3, AlBr 3, ethylaluminum dichloride, diethylaluminum chloride, TiF 4, TiCl 4, TiBr 4, VCI 5, FeF 3, FeCl 3, FeBr 3, ZnF 2, ZnCl 2, ZnBr 2, Cu (I) F, Cu (I) Cl, Cu (I) Br, Cu (II) F 2 , Cu (II) Cl 2 , Cu (II) Br 2 , Sb (III) F 3 , Sb (V) F 5, Sb (III) Cl 3, Sb (V) CI 5, Nb (V) CI 5, Sn (II) F 2, Sn (II) Cl 2, Sn (II) Br 2, Sn (IV) F 4 , Sn (IV) Cl 4 and Sn (IV) Br 4
- the treatment medium used in step a) may comprise at least one salt other than the aforementioned compounds.
- the salts are preferably selected from salts of the abovementioned acids and bases as well as their oxidation or reduction products. Suitable salts are, for. Ammonium, alkali metal or alkaline earth metal sulfates, such as sodium sulfate, potassium sulfate, calcium sulfate or magnesium siumsulfat. Also suitable are ammonium, alkali metal or alkaline earth metal sulfites, such as sodium sulfite, potassium sulfite, calcium sulfite or magnesium sulfite.
- ammonium, alkali metal or alkaline earth metal sulfides such as sodium sulfide, potassium sulfide, calcium sulfide or magnesium sulfide.
- alkali metal hydrogen sulfides such as sodium hydrogen sulfide or potassium hydrogen sulfide.
- the treatment medium used in step a) may contain other compounds other than the compounds mentioned above. These are in particular the customary process chemicals known to the person skilled in the art for the different digestion processes for the production of pulp from a lignocellulose-containing starting material. The following statements on individual embodiments of the digestion in step a) are referred to.
- the digestion in step a) can take place in one or more stages. In the simplest case, the digestion in step a) takes place in one stage. If the treatment is multi-stage, z. B. in 2, 3 or more than 3 stages, the individual stages may differ with respect to the treatment medium used and / or the treatment conditions. In a suitable embodiment of a two-stage digestion in step a) z. For example, in the first stage at least one organic solvent or a mixture of water and at least one organic solvent and in the second stage an alkaline aqueous medium can be used. Such a configuration is z.
- Example the organocell method described in more detail below, wherein in the first stage, the digestion with a water / alcohol mixture and carried out in the second stage, a digestion with aqueous NaOH.
- a two-stage digestion z. B. a subsequent stage at an elevated temperature and / or an elevated pressure than the previous stage.
- the digested material from only one of the stages or from several stages for further processing in step b) can be used. The condition for this, however, is that a lignin-enriched fraction can be isolated from the digested material of the respective stage.
- the digestion in step a) preferably takes place at ambient temperature or preferably above ambient temperature.
- the temperature is preferably in a range from about 40 to 300 ° C., more preferably from 50 to 250 ° C. In a specific embodiment, the temperature is initially increased successively or continuously in the course of the treatment until the desired final temperature is reached.
- the digestion in step a) can be carried out at reduced pressure, at ambient pressure or above the ambient pressure.
- the pressure in step a) is generally in a range of 0.01 bar to 300 bar, preferably 0.1 bar to 100 bar.
- the duration of the digestion in step a) is generally 0.5 minutes to 7 days, preferably 5 minutes to 96 hours.
- an alkaline treatment medium is used in step a).
- Suitable mineral acids are, for. As hydrochloric acid and especially sulfuric acid.
- the treatment with steam success preferably at a temperature in the range of about 1 10 to 300 0 C, particularly preferably 120 to 250 0 C.
- prehydrolysis generally involves 10 to 15% by weight of the lignocellulosic material, based on the total weight, in solution.
- deciduous trees usually 15 to 20 wt .-% of the lignocellulosic material, based on the total weight, go into solution in hardwoods.
- the digestion in step a) can then preferably be carried out by the sulphate process (force process).
- the treatment medium used in step a) then contains as main components NaOH and Na 2 S in an aqueous medium.
- the treatment medium used in step a) contains NaOH, Na 2 S, Na 2 CO 3 and Na 2 SO 4 in an aqueous medium.
- the temperature is carried out in the course of treatment first successively or continuously increased until the desired final temperature is reached.
- This can z. B. the treatment in a first stage at a temperature in the range of about 50 to 130 0 C and in a second stage in a range of about 130 to 250 0 C.
- the duration of the first stage is z. B. 5 to 50%, based on the total treatment time.
- the heating takes place with customary devices, for. B. by heat exchangers, heat baths, gas burners, etc.
- the pressure during the digestion of the lignocellulosic material in step a) is generally in a range from 0.1 bar to 100 bar, preferably 1 bar to 10 bar. In a special version, working at ambient pressure.
- the duration of digestion of the lignocellulosic material in step a) is generally 0.5 minutes to 7 days, preferably 5 minutes to 96 hours.
- the digestion in step a) can furthermore preferably be carried out by the soda process (soda process).
- the treatment medium used in step a) then contains as its main component NaOH in an aqueous medium which is substantially free of sulfur-containing compounds.
- An aqueous medium which is substantially free of sulfur-containing compounds is understood as meaning a medium to which no sulfur-containing compounds have been added as process chemicals.
- the lignocellulosic starting material used in step a) is preferably selected among annual plants such as flax, hemp, sisal, jute, straw, coconut fibers, switchgrass (Panicum virgatum) and other short rotation crops.
- the digestion of the lignocellulose material takes place after the soda in step a) at a temperature in a range of 70 to 300 0 C, Particularly preferably from 100 to 250 0 C.
- the pressure during the digestion of the lignocellulosic material in step a) by the soda process is generally in a range from 0.1 bar to 100 bar, preferably 1 bar to 10 bar.
- the duration of digestion of the lignocellulosic material in step a) by the soda process is generally 0.5 minutes to 7 days, preferably 5 minutes to 96 hours.
- the amount of NaOH used in the digestion of the lignocellulosic material in step a) by the soda process is generally in the range from 5 to 25 parts by weight, more preferably 7 to 20 parts by weight, based on the total weight of the starting lignocellulosic material.
- an alkaline treatment medium is used in step a) and the digestion takes place in an oxygen atmosphere.
- Such methods are also known and are also referred to as alkali-oxygen digestion.
- the pressure during the digestion of the lignocellulosic material in step a) is then generally in a range from 1, 1 bar to 100 bar, preferably 2 bar to 50 bar.
- an alkaline treatment medium is used in step a) and the digestion is carried out in the presence of hydrogen peroxide and / or another peroxide compound.
- Such methods are also known and are also referred to as alkali peroxide digestion.
- an alkaline treatment medium is used in step a) and the digestion is carried out in the presence of anthraquinone.
- the amount of anthraquinone used in the digestion of the lignocellulosic material in step a) is generally in the range from 0.001 to 5 parts by weight, more preferably 0.01 to 1 part by weight, based on the total weight of the lignocellulosic starting material used.
- a treatment medium which comprises at least one organic solvent is used in step a).
- Suitable organic solvents are those mentioned above, to which reference is made here.
- the C 1 -C 4 -alkanols are preferably selected from methanol, ethanol, n-propanol, isopropanol and n-butanol. Preferred are methanol, ethanol and mixtures thereof.
- Mixtures of at least one C 1 -C 4 -alkanol with water preferably contain 10 to 99% by weight, particularly preferably 20 to 95% by weight, of at least one C 1 -C 4 -alkanol, based on the total weight of the mixture.
- the digestion of the lignocellulosic material in step a) is carried out with a treatment medium comprising at least one organic solvent at a temperature in a range from 70 to 250 ° C., more preferably from 100 to 220 ° C.
- the pressure during the digestion of the lignocellulosic material in step a) with a treatment medium which comprises at least one organic solvent is generally in a range from 1 bar to 100 bar, preferably from 2 bar to 50 bar.
- an additive may additionally be used to increase the selectivity of the solubilization of individual cellulose Increase accompanying substances.
- Alkali metal hydroxides such as sodium hydroxide
- Ammonium hydrogen sulfite and alkali and alkaline earth metal hydrogen sulfites such as sodium hydrogen sulfite and magnesium hydrogen sulfite.
- mineral acids such as hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid or amidosulphonic acid and their ammonium, alkali metal and alkaline earth metal salts.
- organic acids such as oxalic acid, formic acid or acetic acid.
- peracids such as persulfuric acid or peracetic acid.
- Alcell method ethanol / water mixture as treatment medium.
- ASAM method Alkaline sulfite-anthraquinone-methanol treatment medium.
- Organocell method Two-stage process with an organic medium in the first stage and an alkaline medium in the second stage, eg. B. digestion with methanol and / or ethanol in the first stage and with methanol and / or ethanol, NaOH, and optionally anthraquinone in the second stage.
- Acetosolv process acetic acid / hydrochloric acid mixture as treatment medium.
- the depolymerization in step a) is not carried out in the presence of an alcohol in the supercritical state.
- step b) of the process according to the invention a cellulose-enriched fraction and at least one cellulose fraction are isolated from the digested material, the cellulose-depleted fraction comprising at least a portion of the treatment medium from step a).
- At least one cellulose-depleted fraction is isolated from the digested material containing at least one component selected from lignin, hemicellulose, cellulose, degradation products of the aforementioned components, and mixtures thereof.
- a cellulose-depleted fraction containing a mixture of two or more than two different components it is not critical for further treatment in step c) to use a cellulose-depleted fraction containing a mixture of two or more than two different components.
- a cellulose-depleted fraction or multiple cellulose-depleted fractions containing a main component which is then subjected to further treatment in step c).
- the main component is understood to mean that the cellulose-depleted fraction contains at least 20% by weight, preferably at least 50% by weight, of this component. especially at least 75 wt .-%, based on the total weight of the fraction contains.
- step b) the isolation of the cellulose-enriched fraction and the cellulose depleted fraction (s) by filtration, centrifugation, extraction, precipitation, distillation, stripping or a combination thereof.
- the person skilled in the art can control the composition of the cellulose-depleted fraction (s) via the isolation process.
- the isolation can be done in one or more stages. So it is z. B. possible in a first stage, for. By filtration and / or centrifuging, separation into the cellulose-enriched fraction and a first cellulose-depleted fraction. The first cellulose-depleted fraction may then be subjected to further separation in one or more further stages.
- Usual filtration processes are z. Cake and depth filtration (described, for example, in A. Rushton, AS Ward, RG Holdich: Solid-Liquid Filtration and Separation Technology, VCH Verlagsgesellschaft, Weinheim 1996, pages 177ff., KJ Ives, in A. Rushton (A. Hg.): Mathematical Models and Design Methods in Solid-Liquid Separation, NATO ASI series E No. 88, Martinus Nijhoff, Dordrecht 1985, pages 90ff.) And cross-flow filtrations (eg described in J. Altmann, S. Ripperger, J. Membrane Sci. 124 (1997), pages 1 19-128). Usual centrifugation methods are z. In G.
- a solvent immiscible with the treatment medium used in step a) or at least one miscibility solvent are used, in which the desired component (eg., Lignin) is soluble in a sufficient amount.
- the extractant is brought into intimate contact with the treatment medium and then a phase separation is carried out.
- the extraction can be carried out in one or more stages by conventional methods.
- distillation columns such as tray columns, which may be equipped with bells, sieve plates, sieve trays, packings, random packings, valves, side draws, etc.
- evaporators such as thin film evaporators, falling film evaporators, forced circulation evaporators, Sambay evaporators, etc., and combinations from that.
- evaporators such as thin film evaporators, falling film evaporators, forced circulation evaporators, Sambay evaporators, etc., and combinations from that.
- evaporators such as thin film evaporators, falling film evaporators, forced circulation evaporators, Sambay evaporators, etc.
- step b) comprises at least one stripping process
- this can be carried out in a customary manner, for. B. with CO2 or water vapor as the stripping gas, are performed.
- the treatment medium employed in step a) is capable of solubilizing at least a portion of the components contained in the lignocellulosic starting material, especially lignin.
- the cellulose contained in the lignocellulose-containing starting material is not or only partially solubilized in the treatment medium.
- the cellulose-enriched fraction and the (first) cellulose-depleted fraction are isolated by filtration or centrifugation. For acceleration, the filtration can be carried out under pressure increased at the cellulose side or at the outlet side.
- the cellulose-enriched fraction isolated in step b) is subjected to a purification to remove any remaining fractions of the treatment medium from step a).
- washing media are those in which at least some of the components contained in the treatment medium at the end of the digestion step a) are good and cellulose does not dissolve or only in small amounts.
- Preferred washing media are the liquid compounds previously described as part of the treatment medium.
- the washing medium is particularly preferably selected from the group consisting of water, water-miscible solvents and mixtures of water and at least one water-miscible solvent. Water is particularly preferably used as the washing medium.
- the cellulose-enriched fraction may be subjected to treatment with a washing medium one or more times in succession.
- the cellulose is brought into intimate contact with the washing medium in a suitable device and the washing medium is subsequently separated from the cellulose.
- suitable devices are for. B. stirred tank, which, if necessary, can be provided with a heater and a device for condensation and recycling of the washing medium.
- the washing medium is at least partially together with the or one of the cellulose-depleted fraction (s) isolated in step b) for further treatment in step c).
- the washing medium is at least partially combined with the cellulose-depleted fraction or, in the case of several, at least one cellulose-depleted fraction.
- the washing medium is completely combined with the cellulose-depleted fraction (s).
- a cellulose-enriched fraction and a hemicellulose-enriched fraction are isolated from the digested material obtained in step a).
- the hemicellulose-enriched fraction comprises at least part of the treatment medium from step a).
- the hemicellulose-enriched fraction is preferably subjected to a treatment by hydrocracking, decarboxylation or a combination thereof in step c).
- a cellulose-enriched fraction and a lignin-enriched fraction are isolated from the digested material obtained in step a).
- the lignin-enriched fraction comprises at least part of the treatment medium from step a).
- the lignin-enriched fraction is preferably subjected to depolymerization treatment in step c).
- the treatment medium used in step a) is capable of solubilizing at least part of the lignin contained in the lignocellulose-containing starting material.
- step b) the isolation of the cellulose-enriched fraction and the lignin-enriched fraction by
- the filtration can be carried out under pressure increased at the cellulose side or at the outlet side.
- the washing medium at least partially together with the lignin-enriched fraction isolated in step b) for depolymerization in step c).
- the washing medium at least partially associated with the lignin-enriched fraction.
- the wash medium is fully combined with the lignin-enriched fraction.
- lignin-enriched fraction is also understood to mean a fraction which additionally contains a liquid washing medium from the wash of the cellulose-enriched fraction.
- step c) at least one cellulose-enriched fraction is subjected to a treatment to obtain at least one valuable substance.
- the treatment in step c) is preferably selected from depolymerization, hydrocracking, decarboxylation and combinations thereof.
- a Torei--assured cellulose fraction is used, at least one under normal conditions (20 0 C and 1 bar 01325) contains liquid compound.
- the cellulose-depleted fraction used for the treatment in step c) preferably has a proportion of compounds which are liquid under normal conditions of at least 10% by weight, more preferably at least 20% by weight, in particular at least 30% by weight. , on.
- the liquid compounds contained in the cellulose depleted fraction comprise at least one liquid compound from the treatment medium used in step a).
- the details of suitable and preferred liquid compounds in step a) are fully incorporated by reference.
- the liquid compounds contained in the cellulose-depleted fraction may additionally contain at least one liquid compound of a washing medium obtained by washing the cellulose-enriched fraction.
- the details of suitable and preferred washing media in step b) are referred to in their entirety.
- a reactor whose surfaces in contact with the fraction contain nickel or consist of nickel.
- the cellulose-depleted fraction isolated in step b), which contains at least part of the treatment medium from step a), can be subjected to depolymerization in step c).
- the depolymerization in contrast for hydrocracking, not carried out with the addition of hydrogen and / or hydrogen-containing gases and / or hydrogen-transferring compounds.
- Depolymerization is understood according to the invention to mean the degradation of a polymeric educt to give low molecular weight products. This includes, in particular, the degradation of a lignin cake to obtain an aroma composition. If desired, the depolymerization can be carried out in the presence of at least one depolymerization catalyst.
- Suitable depolymerization catalysts are in principle all those catalysts which are also used as catalysts for the construction of the polymers. These include z. Silicic acid, alumina, aluminosilicates, layered aluminosilicates and zeolites such as mordenite, faujasite, zeolite X, zeolite-Y and ZSM-5, zirconia or titania.
- the temperature during the depolymerization is preferably in a range from 100 to 350 ° C., particularly preferably 150 to 300 ° C. If an alkaline, cellulose-depleted fraction which additionally contains at least one sulfide and / or hydrogen sulfide is used for the depolymerization in step c) Preferably, the temperature is preferably in the range of 150 to 250 ° C. In a specific embodiment, a black liquor is subjected to depolymerization at a temperature in the range of 150 to 250 ° C. The pressure during the depolymerization is preferably in a range from 1 to 250 bar, preferably 1, 1 to 40 bar.
- the residence time at the depolymerization temperature can be a few seconds to several days. In a specific embodiment, the residence time at the depolymerization temperature is 5 seconds to 5 minutes, more specifically 10 seconds to 3 minutes.
- the cellulose-depleted fraction isolated in step b) which contains at least part of the treatment medium from step a) as well as carbon-containing biomass can be subjected to hydrocracking in step c).
- hydrocracking is understood as meaning a treatment with hydrogen and / or hydrogen-containing gases and / or hydrogen-transferring compounds at elevated temperatures and, if appropriate, elevated pressure.
- the temperature during the hydrocracking is preferably in a range from 50 to 1000 ° C., more preferably from 75 to 60 ° C.
- the hydrocracking pressure is preferably in the range from 1 to 600 bar, preferably from 2 to 500 bar.
- Typical residence times are in the range from 1 minute to 24 hours, preferably from 15 minutes to 8 hours.
- the cracking gas alkanes preferably Ci-C4-alkanes
- the z. B. can be used as diesel oil and for heating purposes.
- a hemicellulose-enriched fraction is used for hydrocracking.
- the process is also very well suited for the combined hydrogenation treatment of cellulose-enriched fractions which have not been subjected to separation into hemicellulose, lignin, etc.
- the hydrogenation of the fraction fractionated with cellulose can be carried out without additional catalysts (ie without the addition of further hydrogenation catalysts to the digestion chemicals present) with very good results.
- additional catalysts ie without the addition of further hydrogenation catalysts to the digestion chemicals present
- Suitable catalysts contain z. Fe, Mo, Ni, Co, W and / or other hydrogenation-active metals and / or compounds and / or complexes thereof.
- the metals and / or their compounds and / or complexes can be applied to carriers, for.
- Example, on alumina, silica, aluminum silicates, zeolites and other carriers known in the art or carrier mixtures or even without carriers are used. Certain zeolites as such are suitable as catalysts.
- hydrogenating gas various hydrogen qualities can be used. Also suitable are admixtures such. B. CO, CO2, H2S, methane, ethane, water vapor, etc. Very well suited for. B. hydrogen qualities, as they arise in gasification reactions of carbon-containing materials with water vapor. Such materials may be residues from the processing of mineral oils, coal, wood, peat, or coal processing residues, such as hydrogenation. Also suitable are biomasses or the vegetable parts separated from domestic waste. Also very suitable is pure hydrogen.
- the cellulose-depleted fraction isolated in step b), which contains at least part of the treatment medium from step a), can be subjected to decarboxylation in step c). This is understood as a formal elimination of CO2. Methods for decarboxylation are known in the art.
- a cellulose-depleted fraction which contains at least part of the treatment medium from step a) is subjected to depolymerization. More preferably, a lignin-enriched fraction is subjected to depolymerization.
- the invention relates to an integrated process for the production of pulp and of an aromatic composition, in which
- step d) isolated from the depolymerization product obtained in step c) an aromatics composition.
- a black liquor from the digestion of a lignocellulose-containing starting material with an alkaline treatment medium is used for depolymerization in step c).
- a black liquor from the sulfate digestion (power digestion) is used for depolymerization in step c).
- a portion of the liquid compounds present may be removed from the lignin-enriched fraction prior to depolymerization in step c).
- Suitable devices are the usual distillation devices and evaporators, such. B. plate evaporator, rotary evaporator, falling film evaporator,
- the removal of the liquid compounds is then carried out in the context of the process for the production of pulp, in which the preparation of the aro matenzusammen applicant is integrated.
- a black liquor are used, which is taken before or during the individual evaporation steps of the underlying pulp process.
- the, lignin-enriched fraction used for the depolymerization in step c) a content of at standard conditions (20 0 C and 1 bar 01325) flüssi- to the compounds of at least 10 wt .-%, particularly preferably at least 20 wt .-% , in particular at least 30 wt .-%, on.
- the depolymerization of the lignin-enriched fraction in step c) preferably comprises the following substeps:
- step c4) optionally adjusting the pH.
- the lignin-enriched fraction is preferably heated to a temperature in the range from 150 to 350 ° C., more preferably from 200 to 300 ° C.
- the critical punk is preferably not exceeded during heating in step c1) and in the subsequent depolymerization in step c2), ie, during heating and depolymerization, the reaction mixture is preferably not in a supercritical state.
- Heat is preferably used for heating in step c1), which originates from the cooling step c3) or another process step of the integrated pulp production process.
- the lignin-enriched fraction in step d) is preferably passed through a heat exchanger.
- the lignin-enriched fraction may be subjected to additional heating with another heat source. This can be done by a suitable device to the reactor used for depolymerization in step c2), via which the reaction mixture can also be maintained at the depolymerization temperature.
- step c2) takes place in a suitable reactor, for. B. in a pressure vessel, which may additionally have a stirring device and a device for heating / cooling of the reactor contents.
- the pressure in the depolymerization in step c2) is generally in a range of 1 bar to 300 bar, preferably 2 bar to 100 bar.
- the duration of depolymerization in step c2) is generally 1 minute to 7 days, preferably 5 minutes to 5 hours.
- At least one compound may be added to the lignin-enriched fraction to promote depolymerization and / or control the composition of the flavor composition obtained in the process of the present invention.
- Suitable compounds are, in principle, the acids, bases and salts mentioned in step a) as a component of the treatment medium, to which reference is hereby made.
- a lignin-enriched fraction in an alkaline treatment medium is used for the depolymerization, then in a first embodiment it is possible to dispense with the addition of further compounds. This applies in particular if a black liquor from the sulfate digestion (force digestion) is used for the depolymerization in step c).
- a lignin-enriched fraction is used in an alkaline treatment medium for depolymerization, to which at least one further compound is additionally added.
- the lignin-enriched fraction at least one compound is added the is selected from bases, ammonium, alkali metal or alkaline earth metal sulfides, alkali metal hydrogen sulfides and mixtures thereof.
- step c1) The addition of at least one compound to promote depolymerization and / or to control the composition of the flavor composition obtained in the process of the invention may take place prior to step c1), during step c1), before step c2) or during step c2).
- a successive addition before or during one or both steps is also possible.
- the depolymerization in step c2) in the presence of a different from these compounds de- polymerization catalyst such.
- inorganic sulfides sodium sulfide, tungsten sulfide, copper sulfide, iron sulfide, etc.
- the composition of the resulting aro- matate composition can be controlled. So occurs z. B. in the absence of sulfur-containing compounds to a much lower proportion dealkylation, as in the presence of sulfur-containing compounds. So z. B. in a depolymerization at a temperature in the range of 250 to 300 0 C in the presence of NaOH a major product guaiacol. Under the same conditions, the NaOH partially, z. B.
- the depolymerization mixture obtained in step c2) is cooled in step c3) to a temperature which is preferably in a range from about 10 to 100 ° C., more preferably from 15 to 60 ° C.
- the depolymerization mixture obtained in step c2) has a pour point (ie a temperature at which the viscous liquid stops flowing)
- the depolymerization mixture is preferably cooled in step c3) to a temperature which is at least 0.1 ° C., particularly preferred at least 1 0 C above the pour point.
- the heat accumulating in step c3) is at least partially recycled in the integrated process for producing pulp and an aroma composition, e.g. In step d), as previously described.
- the pH in step c4) is preferably set to a value of at most 10. This is especially true if a black liquor from the sulfate digestion (power digestion) is used for depolymerization in step c).
- a preferred acid for neutralization is CO2.
- step c) The isolation of at least one valuable substance from the treatment product (s) obtained in step c) can take place by customary methods known to the person skilled in the art. As filtration, centrifugation, extraction, precipitation, crystallization, distillation, or a combination.
- the processes for isolating the cellulose-enriched fraction and the cellulose-depleted fraction (s) described in step b) are hereby incorporated by reference in their entirety.
- step d) the isolation of an aroma composition from a depolymerization product of a lignin-enriched fraction obtained in step c) is carried out.
- the isolation of an aroma composition from the demo polymerization product obtained in step c) is preferably carried out by extraction.
- at least part of the aromatics obtained in the depolymerization in step c) is separated, while the remaining residue (organic components and inorganic process chemicals) further processing and / or thermal utilization, preferably in the context of the integrated process for pulp production, fed can.
- a solvent for extraction, a solvent (extractant) can be used in which the aromatics obtained in the depolymerization are soluble in a sufficient amount and which is otherwise at least partially immiscible with the Depolymerisations.
- the extractant is then intimately contacted with the depolymerization product obtained in step c), followed by phase separation.
- the extraction can be configured in one or more stages. Suitable extractants are non-polar solvents, aprotic polar solvents, alcohols and mixtures thereof. These include z.
- Aromatic hydrocarbons such as benzene, toluene, ethylbenzene or xylene; aliphatic and cycloaliphatic hydrocarbons, such as pentane, hexane, heptane, octane, ligroin, petroleum ether, cyclohexane or decalin; halogenated solvents, such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane or chlorobenzene, alkanols and cycloalkanols, such as 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 1-octanol, cyclohexane and mixtures of the abovementioned solvents.
- the extraction can be discontinuous or continuous.
- discontinuous separation operations can be carried out in cascade succession, wherein the separated from the extractant phase residue is in each case brought into contact with a fresh portion of extractant and / or the extractant is passed in countercurrent.
- discontinuous implementation brings under mechanical movement, for.
- the depolymerization product and the extractant in a suitable vessel the mixture is allowed to rest for phase separation and one of the phases is removed by conveniently drawing off the heavier phase at the bottom of the vessel.
- the extractant and the depolymerization product are continuously fed to suitable apparatus in an analogous manner to the discontinuous variant.
- the extraction takes place z. B. in at least one mixer-separator combination or at least one extraction column.
- Suitable mixers are both dynamic and static mixers.
- the isolation of the aroma composition in step d) comprises the following substeps:
- step d1) extraction of the depolymerization product obtained in step c) to obtain an aromatics-enriched extract Aan) and an aromatic-enriched residue Aab),
- the pH of the de-polymerization product obtained in step c) can be adjusted by adding at least one acid or at least one base prior to extraction.
- the pH of the depolymerization product used in the first stage and the pH of the residue separated from the extractant phase at the respective stage can be adjusted by adding at least one acid or at least one base.
- Suitable acids are, for. As CO2, H2S, and mineral acids, such as hydrochloric acid, sulfuric acid and phosphoric acid.
- Suitable bases are, for.
- alkali metal bases such as sodium hydroxide or potassium hydroxide
- alkali metal carbonates such as soda or potassium carbonate
- alkali hydrogencarbonates such as sodium bicarbonate or potassium bicarbonate
- alkaline earth metal bases such as calcium hydroxide, calcium oxide, magnesium hydroxide or magnesium carbonate and ammonia or amines.
- an alkaline depolymerization product having a pH in the range of 8 to 14 is used for the extraction in step d). Before the extraction, it is preferable to adjust the pH of the depolymerization product to 1 to 9, preferably 6 to 8.
- monomeric aromatics are understood as meaning aromatics which have an aromatic ring.
- oligomeric aromatics are meant aromatics having 2, 3, 4, 5 or up to 10 aromatic rings.
- step d1 For the extraction in step d1), reference is made to the above general comments on the extraction.
- the separation of the extract Aan) in step d2) is preferably carried out by distillation.
- distillative separation of the extract Aan can be carried out by customary methods known to the person skilled in the art.
- Suitable apparatus for the separation by distillation include distillation columns, such as tray columns, which may be provided with bells, sieve plates, sieve trays, packages, internals, valves, side draws, etc.
- Particularly suitable partition wall columns which can be provided with 39abmann, returns, etc.
- evaporators such as thin film evaporators, falling film evaporators, Sambay evaporators, etc., and combinations thereof.
- the distillation is preferably carried out at a bottom temperature in the range of about 30 to 250 0 C, more preferably 50 to 200 0 C.
- the distillation may be carried out under normal pressure or reduced pressure.
- the pressure is preferably in a range of about 0.0005 bar to 1, 1 bar, more preferably 0.001 bar to 1, 0 bar.
- the distillation is carried out in two stages.
- the enriched in oligomeric aromatics fraction A O h g o) can be isolated as the bottom product and the extractant and the monomeric aromatics as a top product in a first stage.
- the top product of the first stage can then be separated in a second stage into an extractant-containing fraction Ex) and a monomeric aromatic-enriched fraction Amono).
- At least 80% by weight, particularly preferably at least 90% by weight, in particular at least 95% by weight, of the extractant can be recovered by the above-described separation of the extract Aan) and its recycling in step d3) ,
- step d4) at least part of the fraction A o h g o) and preferably the entire fraction A o h g o) can be recycled to the depolymerization step c).
- the fraction A O h g o) partially or completely within the framework of the integrated pulp production process. It can, for. B. together with the concentrated aromatics-depleted residue Aab) burned and used for heat recovery.
- the aromatics composition isolated in step d) contains, based on the total weight of the aroma composition, preferably at most 5% by weight, particularly preferably at most 1% by weight, of paraffins.
- the aromatics composition isolated in step d) contains, based on the total weight of the aroma composition, preferably at most 5% by weight, particularly preferably at most 1% by weight, of saturated cyclic hydrocarbon compounds.
- the aromatics composition isolated in step d) contains, based on the total weight of the aroma composition, preferably at least 80% by weight, particularly preferably at least 90% by weight, in particular at least 95% by weight, of monomeric aromatics.
- aromatics composition isolated in step d) contains aromatics which are e.g. B. are selected from phenolic compounds such as mono-, di-, and polyalkylated
- the aromatics composition isolated in step d) contains as aromatics, e.g. Phenol, p-cresol, guaiacol (2-methoxyphenol, 2-hydroxyanisole), catechol (1, 2-dihydroxybenzene, pyrocatechol), methyl guaiacols, ethyl guaiacols, methyl catechols and ethyl catechols.
- the separation of the aroma composition can, for. Example by extraction, distillation or a combination thereof.
- a special embodiment is the extraction with supercritical solvents, eg. With supercritical CO2.
- known processes for distillation, rectification and extraction can be used.
- vanillin (3-methoxy-4-hydroxy-benzaldehyde).
- the aromatics composition isolated from the oxidized sulfite waste liquors contains vanillin as a component.
- a process for the extraction of vanillin from oxidized sulphite waste liquors with CO2 is described in WO87 / 001695.
- the aroma composition isolated from the black liquor usually contains no or only small amounts of vanillin, but generally larger amounts of guaiacol, which can be oxidized by known methods to vanillin.
- the aromatics composition isolated in step d) is dealkylated.
- Processes for dealkylation of aromatics are known to the person skilled in the art and comprise, for example, As the hydrodealkylation or Dampfdealkylierung.
- the aromatics composition isolated in step d) is subjected to dehydroxylation.
- Suitable processes for the reduction of phenols and phenol ethers are, for. In J. March, Advanced Organic Chemistry, 4th edition, John Wiley & Sons, pp. 442-443 and the literature cited therein, to which reference is hereby made.
- the aromatics composition isolated in step d) is subjected to dealkylation and subsequent nuclear hydrogenation.
- the cyclohexanols, cyclohexanediols and cyclohexanepolyols, which may have been previously separated can be subjected to oxidation (dehydrogenation) to the corresponding cyclohexanones.
- the oxidation (dehydrogenation) is z. In J. March, Advanced Organic Chemistry, 4th edition, John Wiley & Sons, p. 1167-1171 and the literature cited therein, which is hereby incorporated by reference.
- This further processing preferably takes place in the context of the process for the production of pulp into which the preparation of the aroma composition is integrated according to the invention.
- the aim of the further processing is the most complete recovery of the process chemicals and the fullest possible thermal utilization of the obtained when digesting the lignocellulosic material non-recyclable organic components of the residue Aab).
- step f) comprises the following substeps:
- step f) The above-described further processing of the residue Aab) in step f) is in principle independent of whether the production of the pulp takes place after the sulphite, sulphate or soda decomposition or one of the abovementioned variants of these processes. Significant differences, however, arise in detail in the chemical recovery. This is known to the skilled worker in principle for all processes for the production of pulp.
- the further processing of the residue Aab) is explained using the example of a preferably used alkaline digestion process and especially of a sulphate (kraft) digestion.
- the concentration of the residue Aab) in step can be done by single or multi-stage evaporation.
- Preferred is a multi-stage evaporation in 2, 3, 4, 5 or more than 5 evaporation stages.
- Suitable evaporators are those previously mentioned in step c).
- z. B. can be designed as a vertical tube evaporator or horizontal tube evaporator. In vertical In the case of the predominantly used types, the liquid to be evaporated flows on the inside of the tubes.
- z. B. from the combustion f2 can be used.
- tube length is typically between 3 and 20 m.
- Typical pipe inside diameters are between 10 mm and 100 mm.
- Horizontal tube evaporators have a lower pressure loss compared to vertical tube evaporators.
- By jet or drop impact from tube to tube higher heat transfer coefficients compared to the vertical tube evaporation set. It is also possible to accommodate a larger heat exchange area based on the apparatus volume.
- step f1 If several evaporators are used in step f1), then these are preferably connected in such a way that optimum heat recovery is made possible (eg vapor compression, multi-effect evaporation).
- the solids content of the concentrated residue Aab) is preferably at least 40% by weight, more preferably at least 50% by weight, in particular at least 60% by weight.
- the combustion of the concentrated residue in step f2) takes place in a conventional incineration plant.
- This is generally provided with a heat exchanger to reuse the heat released during combustion in another area of the method according to the invention or in another method.
- This is z. B. the heat generated during combustion flue gas and used to generate steam.
- the flue gases are a further cleaning, z.
- Part of the energy thus obtained can in the process according to the invention, for. B. in the evaporation step f1, are used.
- the excess energy can be used elsewhere, for.
- the excess heat can be used to generate electricity.
- the concentrated residue Aab) is fed into the combustion chamber of an incinerator.
- the residue is preferably finely divided, z. B. by spraying. Residual liquid evaporates and the solid portion of the residue is pyrolyzed. Combustion usually takes place under reducing conditions.
- sodium sulphate is added for combustion (as a make-up chemical), which is reduced to sodium sulphide. At the same time sodium hydroxide is converted to sodium carbonate.
- step f3) in the sulfate process, the green liquor is subjected to causticization to convert sodium carbonate into sodium hydroxide.
- the resulting so-called white liquor can then be reused for digestion in step a).
- Caustification may be incorporated in a lime burning process. In this case, from calcium carbonate (as another make-up chemical) produced by burning calcium oxide (quicklime), this deleted, with calcium hydroxide (slaked lime) results and carried out with this Kaustreti, which in turn results calcium carbonate, which are then used again for lime burning can.
- FIG. 1 The method described above is shown generally schematically in FIG. 1
- FIG. 2 shows an integrated process for the production of pulp and an aroma composition in which
- step d) isolated from the depolymerization product obtained in step c) an aromatics composition.
- step c) subjecting the lignin-enriched fraction to depolymerization, and d) isolating an aromatherapy composition from the depolymerization product obtained in step c) by extraction,
- step d) optionally subjecting the aromatics composition isolated in step d) to a separation and / or at least one subsequent conversion
- step f) isolating an aromatics-enriched residue from the depolymerization product in step d) and subjecting it to further processing to obtain at least one component which is contained in the treatment medium used in step a), and
- step g) the component (s) of the treatment medium obtained in step f) is recycled in step a).
- FIG. 3 shows an embodiment of the method from FIG. 2, in which the preparation of aromatics is integrated into a sulphate (force) process.
- Example 1 Cleavage of black liquor at 290 0 C in an autoclave
- the extract was analyzed by GC chromatography in THF with heptadecane as internal standard.
- the aromatics phenol (0.25 wt.%), Guaiacol (1.8 wt.%), Pyrocatechol (4.4 wt.%) And vanillin (0.6 wt.%) Were quantified.
- Example 2 Cleavage of black liquor at 240 ° C. in an autoclave
- the extract was analyzed by GC chromatography in THF with heptadecane as internal standard.
- Example 3 Comparison with the splitting of dissolved kraft lignin at 290 ° C. in an autoclave
- Example 4 Cleavage at 290 0 C in a continuous reactor
- Example 5 447 g of an untreated black liquor with a pH of 12.5 were adjusted to pH 7.0 with CO2. Subsequently, 447 g of 1-hexanol as extracting agent were added and stirred vigorously at room temperature for 10 minutes. Then the phases were separated by gravity. After settling, 472 g of organic phase and 422 g of aqueous phase were obtained. The organic phase was evaporated, leaving 1, 8 g of evaporation residue left. The vapor was condensed and analyzed by gas chromatography (GC). 1, 2 area% of an aromatic-rich fraction was found in it. Assuming that the weight proportions correspond to the area proportions, it was possible to recover 5.7 g of aromatics-rich fraction from the untreated black liquor.
- GC gas chromatography
- Untreated black liquor according to the invention was thermally treated at 290 0 C for 1 min.
- 447 g of this black liquor treated according to the invention (ie the same amount as in Example 5) were adjusted to pH 7.7 with CO2.
- 447 g of 1-hexanol as extraction agent were again added thereto and stirred vigorously at room temperature for 10 minutes.
- the phases were separated in a centrifuge. After settling, 389 g of organic phase and 186 g of aqueous phase were obtained. Between the organic and the aqueous phase, after the phase separation, there was a third (about 164 g).
- a pure solid phase formed (about 155 g).
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- Extraction Or Liquid Replacement (AREA)
Abstract
Description
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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RU2011113398/05A RU2535222C2 (ru) | 2008-09-08 | 2009-09-07 | Способ интегрированного получения целлюлозы и пригодных для повторного использования низкомолекулярных веществ |
US13/062,732 US8853478B2 (en) | 2008-09-08 | 2009-09-07 | Method for the integrated production of cellulose and low-molecular-weight reusable materials |
BRPI0918489A BRPI0918489A2 (pt) | 2008-09-08 | 2009-09-07 | processo integrado para produzir polpa e pelo menos um material de valor de baixo peso molecular |
EP09782673A EP2334625A1 (de) | 2008-09-08 | 2009-09-07 | Verfahren zur integrierten herstellung von zellstoff und niedermolekularer wertstoffe |
CA2735396A CA2735396C (en) | 2008-09-08 | 2009-09-07 | Method for the integrated production of cellulose and low-molecular-weight reusable materials |
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EP08163886.8 | 2008-09-08 | ||
EP08163886 | 2008-09-08 |
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WO2010026244A1 true WO2010026244A1 (de) | 2010-03-11 |
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PCT/EP2009/061529 WO2010026244A1 (de) | 2008-09-08 | 2009-09-07 | Verfahren zur integrierten herstellung von zellstoff und niedermolekularer wertstoffe |
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US (1) | US8853478B2 (de) |
EP (1) | EP2334625A1 (de) |
BR (1) | BRPI0918489A2 (de) |
CA (1) | CA2735396C (de) |
RU (1) | RU2535222C2 (de) |
WO (1) | WO2010026244A1 (de) |
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WO2011138355A2 (de) | 2010-05-07 | 2011-11-10 | Basf Se | Verfahren zur herstellung von zellstoff und wenigstens einem organischen flüssigen oder verflüssigbaren wertstoff mit abgasrückführung |
US20110275869A1 (en) * | 2010-05-07 | 2011-11-10 | Basf Se | Process for producing synthesis gas and at least one organic liquid or liquefiable material of value |
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WO2015105882A1 (en) * | 2014-01-07 | 2015-07-16 | Api Intellectual Property Holdings, Llc | Processes for producing high-yield pulp and paper products |
RU2557227C1 (ru) * | 2014-05-23 | 2015-07-20 | Владимир Георгиевич Андреев | Способ переработки растительной биомассы |
US11078548B2 (en) | 2015-01-07 | 2021-08-03 | Virdia, Llc | Method for producing xylitol by fermentation |
AT519535A1 (de) * | 2016-12-23 | 2018-07-15 | Univ Wien Tech | Herstellungsverfahren |
US11174354B2 (en) | 2016-12-23 | 2021-11-16 | Technische Universität Wien | Production of lignin particles |
WO2020002361A1 (en) * | 2018-06-25 | 2020-01-02 | Katholieke Universiteit Leuven | Fractionation and depolymerisation of lignocellulosic material |
WO2020000008A1 (de) | 2018-06-27 | 2020-01-02 | Technische Universität Wien | Verfahren zur herstellung von ligninpartikeln |
WO2020101563A1 (en) * | 2018-11-15 | 2020-05-22 | Kat2Biz Ab | Method of forming monomers and furfural from lignocellulose |
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BRPI0918489A2 (pt) | 2015-12-01 |
RU2011113398A (ru) | 2012-10-27 |
CA2735396A1 (en) | 2010-03-11 |
EP2334625A1 (de) | 2011-06-22 |
CA2735396C (en) | 2016-09-06 |
RU2535222C2 (ru) | 2014-12-10 |
US8853478B2 (en) | 2014-10-07 |
US20110268652A1 (en) | 2011-11-03 |
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