WO2001046520A1 - Procede d'extraction/recuperation d'acides carboxyliques dans des lessives usees resultant de la production de cellulose a l'aide d'agents d'extraction - Google Patents

Procede d'extraction/recuperation d'acides carboxyliques dans des lessives usees resultant de la production de cellulose a l'aide d'agents d'extraction Download PDF

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Publication number
WO2001046520A1
WO2001046520A1 PCT/EP2000/013010 EP0013010W WO0146520A1 WO 2001046520 A1 WO2001046520 A1 WO 2001046520A1 EP 0013010 W EP0013010 W EP 0013010W WO 0146520 A1 WO0146520 A1 WO 0146520A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
carboxylic acids
acid
extraction
extractant
Prior art date
Application number
PCT/EP2000/013010
Other languages
German (de)
English (en)
Inventor
Sven Siegle
Original Assignee
Natural Pulping Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE1999162411 external-priority patent/DE19962411A1/de
Priority claimed from DE2000157878 external-priority patent/DE10057878A1/de
Application filed by Natural Pulping Ag filed Critical Natural Pulping Ag
Publication of WO2001046520A1 publication Critical patent/WO2001046520A1/fr

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Classifications

    • 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
    • D21C11/0042—Fractionating or concentration of spent liquors by special methods
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C11/00—Regeneration of pulp liquors or effluent waste waters
    • D21C11/0007—Recovery of by-products, i.e. compounds other than those necessary for pulping, for multiple uses or not otherwise provided for
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C3/00—Pulping cellulose-containing materials
    • D21C3/20—Pulping cellulose-containing materials with organic solvents or in solvent environment

Definitions

  • the present invention relates to a process for the recovery / recovery of carboxylic acids from leaching from pulp production.
  • the digestion is carried out in acetic acid to which 5 to 10% formic acid has been added, and in the Acetosolv process, the digestion is carried out in acetic acid with a small proportion of hydrochloric acid.
  • a new process for producing a pulp from lignocellulose-containing material, in which carboxylic acids are used, is in DE 100 57 878.0 the local applicant.
  • the raw material is broken down in an at least binary solvent mixture.
  • the solvent mixture has at least a first solvent A and a second solvent B.
  • the solvent A is selected from the group of the aliphatic organic mono- or polyfunctional carboxylic acids, hydroxycarboxylic acids or carboxylic acid derivatives, in particular carboxylic acid esters or carboxylic acid anhydrides.
  • the solvent B is a dipolar aprotic solvent with a boiling point between 80 ° C and 250 ° C and a refractive index n D 20 in the range between 1, 30 and 1, 55 or a solvent from the group of alkylene glycols, oligoalkylene glycols and polyalkylene glycols.
  • formic acid, acetic acid, propionic acid, butyric acid, tartaric acid, citric acid, oxalic acid, malonic acid and / or acetic anhydride and solvent B cyclohexanone, cyclohexanol, acetonitrile, nitromethane, dimethyl sulfoxide, xylene, dimethylformamide, hexanol, toluene are preferred for this process .
  • Butyl acetate, dimethylacetamide, HMPT, cyclopentanone, cyclopentanol, diethylene glycol, triethylene glycol, tetraethylene glycol, (PEG 200), PEG 400 and / or PEG 600 are used. It is particularly preferred to use formic acid and / or acetic acid as the carboxylic acids.
  • the Acetocell process which may have failed, suggests the use of acetic acid at high pressure and temperature for digestion.
  • lignin is extracted from the cellulose-containing material.
  • cellulose can break down into complex carbohydrates and soluble sugars during the digestion.
  • acetic acid Depending on the cellulose-containing material used, digestion also produces acetic acid in different proportions. If, for example, wood is used as the cellulose-containing material in the process known from WO 96/35013, which is carried out in formic acid, then among the Digestion conditions up to 5% acetic acid formed; If straw is used as the cellulose-containing material, the acetic acid content is only about 0.04 to 0.5%.
  • Lignin is also partially broken down and / or derivatized by the digestion, so that the leaching of the cellulose production also leads to degradation products of the lignin, e.g. Cumaryl, coniferyl and sinapinal alcohol, their derivatives such as syringa or guaiacyl aldehyde, syringol, guaiacol, short-chain condensation products such as esters, ethers or hemiacetals, and degradation products of the lignocellulose-containing material, such as sugar or their degradation products, can be found in different proportions.
  • the lignin e.g. Cumaryl, coniferyl and sinapinal alcohol, their derivatives such as syringa or guaiacyl aldehyde, syringol, guaiacol, short-chain condensation products such as esters, ethers or hemiacetals
  • degradation products of the lignocellulose-containing material such as sugar or their degradation
  • Lignin with double bonds, carbonyl and carboxy groups, derivatives such as vanillin, syringaldehyde, syringol, vanillic acid, syringic acid, 4-hydroxybenzoic acid, aceto-vanillin, acetosyringone and dihydroconiferyl alcohol are also produced during the digestion.
  • the type and the respective proportions of the lignin derivatives and degradation products contained in the waste liquor depend on the type and the reaction procedure in the respective digestion process. Conditions that promote the formation of degradation products are high temperatures, high acidity, oxidizing agents (for example H 2 O 2 , O 2 , O 3 peracids), long digestion times and chemical additives.
  • waste liquors from pulp production are thus highly complex mixtures which, depending on the cellulose-containing material used, also vary greatly, both with regard to the species contained in the waste liquor and with regard to their respective concentration.
  • a waste liquor from the natural pulping process according to WO 96/35013 can comprise, for example, the following components: approximately 67% formic acid, approximately 29% water, approximately 3-4% lignin, approximately 0.04-0.5% Acetic acid and at least 0.26% furfural.
  • the waste liquor also contains lignin derivatives, lignin degradation products, complex carbohydrates and soluble sugars.
  • WO 96/35013 proposes a simple distillation, by means of which, as a rule, over 95% of the formic acid can be recovered. The remaining portion remains with the lignin according to the state of the art. After the formic acid has been recycled by distillation, the distillation residue comprising the lignin and the higher carboxylic acids is added to water, whereupon lignin precipitates and can be separated from the remaining constituents.
  • a further disadvantage of this known process is that, due to the temperatures required for the distillation, the lignin is gradually condensed and tarred (a brown-black, tarry, lumpy, sticky mass) and further processing of the native lignin is no longer possible.
  • distillative formic acid recovery requires an increase in temperature up to 107 ° C, which is associated with an additional energy expenditure. A separation of the acetic acid formed during the digestion also does not take place in this process.
  • a formic acid / acetic acid / water mixture with a fluctuating composition is thus obtained.
  • Spray drying is expensive and requires a lot of energy.
  • the diluted acid mixture is then processed in distillation plants to create a recyclable cooking acid.
  • the lye powder, which comprises lignin and hemicellulose, is then burned for energy.
  • DE 36 26 968 A1 describes a method for extraction, among other things. also known from carboxylic acids from dilute aqueous solutions, in which s-butyl-di-n-octyl-phosphine oxide is used as the extractant.
  • a process for the extraction of carboxylic acids from aqueous solutions which comprise at most 2% by weight of carboxylic acids is likewise known from US Pat. No. 3,816,524, in which trialkylphosphine oxides are used as the extracting agent.
  • the object of the present invention is to improve the recovery or recovery of carboxylic acid from the lignin-containing waste liquors from pulp production and to provide an environmentally friendly process for the recovery of carboxylic acids.
  • the extracting agent used according to the invention should preferably have no halogens and / or no sulfur and / or no phosphorus, which is the case with the previously known extracting agents.
  • the carboxylic acid (s) used for the digestion process should preferably not include any halogens and / or sulfur and / or phosphorus compounds.
  • Suitable extraction agents are alkyl ethers, preferably the symmetrical alkyl ethers, in particular diisopropyl ether (DIPE) and di-t-butyl ether, but also the asymmetrical alkyl ethers such as methyl t-butyl ether and the cyclic ethers such as dioxane or 4,4-dimethyl-1, 3-dioxane proven.
  • DIPE diisopropyl ether
  • cyclic ethers such as dioxane or 4,4-dimethyl-1, 3-dioxane proven.
  • diisopropyl ether DIPE
  • DIPE diisopropyl ether
  • Diisopropyl ether is also a waste product in the chemical industry and is comparatively cheap. If diisopropyl ether is used as the extractant, the process should be carried out under a protective gas. The specific weight of the diisopropyl ether is less than that of the digestion solution, so that the extract phase is preferably taken off at the top of the extraction column.
  • the extraction process takes place at temperatures around 60 ° C. At these temperatures there is still no thermal change in the lignin.
  • diisopropyl ether used as the extraction agent, the lignin which precipitates and is separated off after the extraction in the extraction sump is still soluble in acetone, which proves that no structural change in the lignin has taken place as a result of the extraction process. The separated lignin can thus be sent to the desired further processing.
  • saturated or unsaturated hydrocarbons such as heptane or 4-methyl-3-pentene, saturated, unsaturated and / or cyclic alcohols with at least five carbon atoms, preferably at least six carbon atoms, particularly preferably at least seven carbon atoms, such as 4- Methyl-2-pentanol, alkyl and aryl esters such as acetic, propionic, formic, butanoic, terephthalic or benzoic esters.
  • saturated or unsaturated hydrocarbons such as heptane or 4-methyl-3-pentene
  • saturated, unsaturated and / or cyclic alcohols with at least five carbon atoms, preferably at least six carbon atoms, particularly preferably at least seven carbon atoms, such as 4- Methyl-2-pentanol, alkyl and aryl esters such as acetic, propionic, formic, butanoic, terephthalic or benzoic esters.
  • ethyl, n- and iso- Propyl, butyl, pentyl, hexyl and cyclohexyl esters are used
  • possible propionic acid esters are the ethyl and propyl esters
  • possible formic acid esters are the propyl and isopropyl esters.
  • Butanediol formate can also be used as the formic acid ester.
  • butanoic acid esters are, for example, methyl and ethyl esters, diethyl terephthalate can be used as terephthalate and ethyl ester as benzoate.
  • Tri-n-octylamine and tri-n-decylamine are suitable as extraction agents from the group of the alkyl and arylamines.
  • Cyclohexanone and cyclopentanone are preferably selected as cyclic alkyl ketones. Unsaturated alkyl ketones and methyl isobutyl ketone, methyl propylene ketone and methyl butyl ketone can also be used as extractants. Both branched and unbranched carboxylic acids can be selected as alkyl monocarboxylic acids. The alkyl monocarboxylic acids should preferably have at least six carbon atoms.
  • Suitable alkyl and aryl amides include Salicylamides with N-heterocycles, suitable aromatics are toluene or xylenes and, for example, furfural can be used as the aldehyde.
  • the process according to the invention is particularly suitable for the recovery of the carboxylic acids from leaching from the acid digestion process.
  • the waste liquor to be extracted preferably has no solids.
  • the digestion liquid is extracted with the extractant according to the invention, preferably continuously in countercurrent circulation.
  • the extractant is preferably bubbled through the solution to be extracted in the form of fine droplets, ie with a large surface area.
  • the carboxylic acids accumulate in the extractant according to the invention as a result of distribution coefficient.
  • the extraction agent is regenerated by distillation.
  • the extractant Since the boiling points of the carboxylic acids for most extractants, in particular when using the particularly preferred diisopropyl ether, are generally considerably higher than that of the extractant, the extractant is usually separated off from the extract phase, so that the carboxylic acids accumulate in the distillation residue.
  • the carboxylic acids, in particular formic and acetic acid, are then distilled off from the distillation residue, formic acid being obtained in a concentration of up to 99% in aqueous solution, ie in a far higher concentration than the azeotrope.
  • the distillation of the carboxylic acids also cleans them of any lignin entrained in the extraction.
  • the waste liquors to be extracted according to the invention generally have at least 10% by weight, preferably at least 20% by weight and particularly preferably at least 40% by weight, of carboxylic acids.
  • the percentage of formic acid recovered is at least 99%.
  • An important advantage of the process according to the invention is that the extraction of the digestion solution takes place at much lower temperatures than the distillation, so that there is no undesirable thermal change in the lignin (structural degradation by condensation and tarification) in the distillative process.
  • the process according to the invention even enables the recovery of formic acid which is much more concentrated than is possible according to the known distillative processes. If instead of the formic acid recovered by distillation in the natural pulping process (cf. WO 96/35013) the solvent used is not the recycled azeotropic formic acid / water but the more concentrated formic acid recycled by the process according to the invention, the pulp produced has otherwise remained the same Process conditions lower kappa numbers.
  • the possible use of more concentrated formic acid in the natural pulping process as a result of the recycling process according to the invention also leads to an acceleration of the entire digestion process and - due to the low kappa numbers achieved - to a simplification of the subsequent bleaching step which is required in many cases.
  • the use of more concentrated formic acid on the digestion process shows no adverse effects on the quality of the cellulose, such as a shortening of the chain lengths or deterioration of the tear properties.
  • the lignin can be separated from the digestion solution by means of membrane processes, ultrafiltration or vacuum evaporation.
  • a solvent in which lignin is not soluble should be used as the extraction agent.
  • dissolved lignin is to be available in a suitable solvent for further processing, it is advantageous to extract an extracting agent select in which lignin is soluble in addition to the carboxylic acids.
  • the lignin is then extracted together with the carboxylic acids and the extractant is separated off, so that lignin dissolved in relatively concentrated formic acid is available for further processing.
  • the formic acid can then be recovered after further processing of the dissolved lignin and used again as a solvent for the pulp production.
  • a further preferred embodiment of the process according to the invention provides for digestion in a carboxylic acid and at least one further solvent B according to DE 100 57 878.0 to use solvent B itself as the extractant.
  • DE 100 57 878.0 teaches that cyclohexanone, cyclohexanol, acetonitrile, nitromethane, dimethyl sulfoxide, xylene, dimethylformamide, hexanol, toluene, butyl acetate, dimethylacetamide, HMPT, cyclopentanone, cyclopentanol, diethylene glycol, triethylene glycol, as additional solvent B (PEG 200), PEG 400 and / or PEG 600 can be used.
  • Alcohols, ketones, aromatics, esters and amides, in particular cyclohexanone, cyclopentanone, butyl acetate, toluene and xylene, for example, are suitable both as additional solvent B and as an extractant.
  • FIG. 1 shows a schematic representation of the method according to the invention for an extraction with diisopropyl ether (DIPE) (extractant of lower density than waste liquor)
  • DIPE diisopropyl ether
  • the waste liquor from the pulp production is in the extraction column 11.
  • the waste liquor comprises about 67% formic acid (F), 29% water (W), 3-4% lignin (L), 0.04 in the pulp production using the natural pulping process up to 0.5% acetic acid (A), at least 0.26% furfural as well as dissolved sugars and complex carbohydrates.
  • the extractant preferably diisopropyl ether (DIPE)
  • DIPE diisopropyl ether
  • the extractant is passed from below in countercurrent through line 19 into the leach extraction column 11 and through the leach liquor (F, A, W, L) to be extracted, in particular the carboxylic acids (F, A) in skip the extract phase.
  • Traces of colloidally dissolved lignin also pass into the organic phase.
  • the extract phase comprising the carboxylic acids, especially formic acid (F), acetic acid (A), traces of lignin (L) and the extracting agent DIPE is of lower density than the extracted waste liquor when using DIPE and is separated off at the upper end of the extraction column 11 and through line 12 to the distillation device 13 for the extractant.
  • the extraction agent DIPE is distilled under mild conditions (temperature of approx. 70 ° C.) from the extracts combined from lines 12 and 21.
  • the distilled, recovered diisopropyl ether is then used for renewed extraction in column 11 or previously fed to decanter 34 for better 3-phase separation.
  • the extraction sump which has water (W), lignin (L) and residues of carboxylic acids (F, A), is removed from the extraction column 11 via line 15, the lignin is separated in the decanting device 34 and the moist lignin is used for the further Use in the drying device 17 dried.
  • the water W formed in the lignin drying 17 is fed through line 23 to a second distillation system 33 for the extractant in order to recover remaining traces of the extractant.
  • the extraction sump is separated into three phases: an organic phase (F, A, DIPE), an aqueous phase and a solid phase (L).
  • the extract phase derived from the decanting device 34 with line 20 has traces of DIPE as well as formic acid and acetic acid and can be used by means of the tap 18 either for renewed extraction into the waste liquor extraction column 11 (line 19) or for further separation of the diisopropyl ether and for recovery of the carboxylic acids are introduced into the distillation column 13 by means of the feed line 21.
  • the aqueous phase from the decanting device 34 which contains dissolved sugar and traces of DIPE, is likewise introduced via line 24 into the second DIPE distillation device 33 in order to recover the extracting agent almost quantitatively.
  • the extraction takes place at a temperature of approx. 60 ° C.
  • one volume of digestion solution with one to three volumes of diisopropyl ether is extracted for 1 to 8 hours in circulation, the extraction at a temperature between 30 and 67, preferably between 50 and 60 ° C. and particularly preferably about 60 ° C. should be done.
  • the particularly preferred embodiment of the method described in FIG. 1 can of course be modified depending on the extracting agent used, the desired yield, etc., for example by means of other connection variants.

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  • Extraction Or Liquid Replacement (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédé permettant de récupérer et/ou d'isoler des acides carboxyliques dans des lessives usées résultant de la production de cellulose. Lesdites lessives contiennent des acides carboxyliques, de la lignine, de l'eau, ainsi, éventuellement, que des hydrates de carbone complexes, du furfural et du sucre dissous. Ledit procédé est caractérisé en ce que les acides carboxyliques sont extraits des lessives usées à l'aide d'un agent d'extraction choisi dans le groupe des éthers, des hydrates de carbone saturés et insaturés, des alcools, des esters d'alkyle et d'aryle, des amines d'alkyle et d'aryle, des alkylcétones cycliques et/ou insaturées ainsi que de la méthylisobutylcétone, de la méthylbutylcétone et de la méthylpropylcétone, des acides monocarboxyliques alkylés, des amides d'alkyle et d'aryle, des composés aromatiques et des aldéhydes.
PCT/EP2000/013010 1999-12-22 2000-12-20 Procede d'extraction/recuperation d'acides carboxyliques dans des lessives usees resultant de la production de cellulose a l'aide d'agents d'extraction WO2001046520A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19962411.9 1999-12-22
DE1999162411 DE19962411A1 (de) 1999-12-22 1999-12-22 Verfahren zur Gewinnung/Rückgewinnung von Carbonsäuren aus Ablaugen der Zellstoffherstellung
DE10057878.0 2000-11-21
DE2000157878 DE10057878A1 (de) 2000-11-21 2000-11-21 Verfahren zur Herstellung einer Pulpe aus cellulosehaltigem Material

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WO2001046520A1 true WO2001046520A1 (fr) 2001-06-28

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WO (1) WO2001046520A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1297549C (zh) * 2004-11-12 2007-01-31 山东泉林纸业有限责任公司 一种由制浆黑液的酸析滤液制备糠醛的方法
WO2009130386A1 (fr) * 2008-04-21 2009-10-29 Kemira Oyj Procede de recuperation d’acide formique
CN109706769A (zh) * 2018-12-29 2019-05-03 齐鲁工业大学 一种小分子醛类有机物共混有机酸分离木质纤维素的方法

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US2714118A (en) * 1953-07-22 1955-07-26 Sonoco Products Co Recovery of chemicals from black liquor
EP0111699A1 (fr) * 1982-12-17 1984-06-27 Extraktionstechnik Gesellschaft für Anlagenbau m.b.H. Procédé de récupération de furfural et d'acides monocarboxyliques à partir de solutions aqueuses
EP0259583A2 (fr) * 1986-08-08 1988-03-16 Hoechst Aktiengesellschaft Procédé continu pour l'extraction d'acides carboxyliques, aldéhydes, cétones, alcools et phénols des solutions aqueuses diluées
EP0273758A2 (fr) * 1986-12-31 1988-07-06 Neste Oy Procédé de séparation de la lignine et du phénol des solutions phénoliques
EP0325891A1 (fr) * 1988-01-25 1989-08-02 Kunz Holding Gmbh & Co. Kg Procédé pour obtenir une pâte de cellulose blanchie
US5788812A (en) * 1985-11-05 1998-08-04 Agar; Richard C. Method of recovering furfural from organic pulping liquor

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2714118A (en) * 1953-07-22 1955-07-26 Sonoco Products Co Recovery of chemicals from black liquor
EP0111699A1 (fr) * 1982-12-17 1984-06-27 Extraktionstechnik Gesellschaft für Anlagenbau m.b.H. Procédé de récupération de furfural et d'acides monocarboxyliques à partir de solutions aqueuses
US5788812A (en) * 1985-11-05 1998-08-04 Agar; Richard C. Method of recovering furfural from organic pulping liquor
EP0259583A2 (fr) * 1986-08-08 1988-03-16 Hoechst Aktiengesellschaft Procédé continu pour l'extraction d'acides carboxyliques, aldéhydes, cétones, alcools et phénols des solutions aqueuses diluées
EP0273758A2 (fr) * 1986-12-31 1988-07-06 Neste Oy Procédé de séparation de la lignine et du phénol des solutions phénoliques
EP0325891A1 (fr) * 1988-01-25 1989-08-02 Kunz Holding Gmbh & Co. Kg Procédé pour obtenir une pâte de cellulose blanchie

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1297549C (zh) * 2004-11-12 2007-01-31 山东泉林纸业有限责任公司 一种由制浆黑液的酸析滤液制备糠醛的方法
WO2009130386A1 (fr) * 2008-04-21 2009-10-29 Kemira Oyj Procede de recuperation d’acide formique
WO2009130387A2 (fr) 2008-04-21 2009-10-29 Kemira Oyj Procédé de préparation de sel de formiate
WO2009130387A3 (fr) * 2008-04-21 2010-04-01 Kemira Oyj Procédé de préparation de sel de formiate
US8492586B2 (en) 2008-04-21 2013-07-23 Kemira Oyj Process for preparation of formate salt
US8530695B2 (en) 2008-04-21 2013-09-10 Kemira Oyj Process for recovery of formic acid
CN109706769A (zh) * 2018-12-29 2019-05-03 齐鲁工业大学 一种小分子醛类有机物共混有机酸分离木质纤维素的方法
CN109706769B (zh) * 2018-12-29 2021-10-01 齐鲁工业大学 一种小分子醛类有机物共混有机酸分离木质纤维素的方法

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