CN113603899A - Method for pretreating lignocellulose by using Lewis base to assist neutral eutectic solvent - Google Patents
Method for pretreating lignocellulose by using Lewis base to assist neutral eutectic solvent Download PDFInfo
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- CN113603899A CN113603899A CN202110784081.9A CN202110784081A CN113603899A CN 113603899 A CN113603899 A CN 113603899A CN 202110784081 A CN202110784081 A CN 202110784081A CN 113603899 A CN113603899 A CN 113603899A
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- eutectic solvent
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- 239000002904 solvent Substances 0.000 title claims abstract description 53
- 230000005496 eutectics Effects 0.000 title claims abstract description 51
- 239000002879 Lewis base Substances 0.000 title claims abstract description 30
- 150000007527 lewis bases Chemical class 0.000 title claims abstract description 30
- 230000007935 neutral effect Effects 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 30
- 229920005610 lignin Polymers 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 239000001913 cellulose Substances 0.000 claims abstract description 12
- 229920002678 cellulose Polymers 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 12
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims abstract description 11
- 235000019743 Choline chloride Nutrition 0.000 claims abstract description 11
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims abstract description 11
- 229960003178 choline chloride Drugs 0.000 claims abstract description 11
- 239000011259 mixed solution Substances 0.000 claims abstract description 9
- 238000005406 washing Methods 0.000 claims abstract description 8
- 238000003916 acid precipitation Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims abstract description 7
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 238000003828 vacuum filtration Methods 0.000 claims abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 235000010265 sodium sulphite Nutrition 0.000 claims description 3
- 235000017166 Bambusa arundinacea Nutrition 0.000 claims description 2
- 235000017491 Bambusa tulda Nutrition 0.000 claims description 2
- 244000025254 Cannabis sativa Species 0.000 claims description 2
- 244000082204 Phyllostachys viridis Species 0.000 claims description 2
- 235000015334 Phyllostachys viridis Nutrition 0.000 claims description 2
- 239000011425 bamboo Substances 0.000 claims description 2
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 2
- 239000011121 hardwood Substances 0.000 claims 1
- 239000011122 softwood Substances 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract description 8
- 238000002203 pretreatment Methods 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 6
- 239000002028 Biomass Substances 0.000 abstract description 5
- 229920002488 Hemicellulose Polymers 0.000 abstract description 4
- 238000004537 pulping Methods 0.000 abstract description 4
- 230000018044 dehydration Effects 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 240000008042 Zea mays Species 0.000 description 15
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 15
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 15
- 235000005822 corn Nutrition 0.000 description 15
- 239000010902 straw Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 6
- 239000002023 wood Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 238000013478 data encryption standard Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000002551 biofuel Substances 0.000 description 3
- 231100000956 nontoxicity Toxicity 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 239000010907 stover Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 108010059892 Cellulase Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 229920002522 Wood fibre Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010170 biological method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229940106157 cellulase Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000002029 lignocellulosic biomass Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XPFJYKARVSSRHE-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].[Na+].[Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O XPFJYKARVSSRHE-UHFFFAOYSA-K 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compounds Of Unknown Constitution (AREA)
- Processing Of Solid Wastes (AREA)
Abstract
The invention belongs to the field of comprehensive utilization of biomass resources, and particularly relates to a method for pretreating lignocellulose by using a Lewis base-assisted neutral eutectic solvent. The method comprises the following steps: and (3) placing the air-dried and crushed plant fiber raw material into a prepared glycerin/choline chloride eutectic solvent, and then adding Lewis base. And (3) heating the solid-liquid mixture for pretreatment, carrying out vacuum filtration on the mixed solution, and washing the washing solution to obtain solid residues and liquid fractions. The regenerated lignin of the liquid fraction was collected by acid precipitation. The method takes Lewis base as a catalyst to assist the neutral eutectic solvent to pretreat the lignocellulose, has good effects of removing lignin and hemicellulose and retaining the cellulose, obviously improves the enzymolysis saccharification efficiency, and can recycle the eutectic solvent aqueous solution after concentration and dehydration. The pretreatment method provided by the invention has good application prospect in the fields of biomass pretreatment and pulping and papermaking.
Description
Technical Field
The invention belongs to the field of comprehensive utilization of biomass, and particularly relates to a method for pretreating lignocellulose by using a neutral eutectic solvent assisted by Lewis base.
Background
Lignocellulosic biomass such as agricultural and forestry crops and energy crops has the characteristics of being renewable, large in production amount, rich in carbohydrate and the like, and the new energy is fully utilized to be converted into biochemical and biofuel, so that the use of fossil energy can be reduced, and economic value and ecological benefit are brought. The cellulose, hemicellulose and lignin are closely interwoven through hydrogen bonds, covalent bonds and non-covalent bonds to form a complex three-dimensional structure. From the standpoint of conversion utilization of the wood-based feedstock, the structural resistance of the wood-based feedstock can affect the liquid permeability or enzyme accessibility during processing, thereby affecting the conversion cost thereof. Different pretreatment methods are usually required to improve the utilization efficiency, such as physical treatment, thermochemical treatment, biological method, etc. However, the conventional methods have respective disadvantages, which limit the application thereof, such as high cost, long period and low enzymatic saccharification efficiency.
The eutectic solvent (DES) consists of a hydrogen bond donor and a hydrogen bond acceptor, and is a new generation green solvent with no toxicity, good biocompatibility and low cost. More importantly, the DESs can significantly disrupt lignin-carbohydrate complexes (LCCs) and selectively extract hemicellulose and lignin. Among them, neutral DESs using glycerol, ethylene glycol, or the like as a hydrogen bond donor have advantages of low viscosity, high thermal stability, and the like, compared with other DESs, and can be applied on a large scale.
Kim et al (Kim, K.H., Dutta, T., et al. Biomass pretreatment using deep electrically soluble sugars from lignin derived phenols, 2018,20(4),809-815.) studies showed that pretreatment of lignocellulose with choline chloride/4-hydroxybenzyl alcohol resulted in only 0.4% lignin removal, with an enzymatic saccharification efficiency of only 32.0%. Procences (Procences, A., Johnson, E., et al. deep electrically active solvent pretreatment and sub-sequence saccharification of corn seed. Bioresource technology, 2015,192,31-6.) et al used choline chloride/glycerol to destructure corn cores, and found that saccharification efficiencies were only 1.79% at 15h pretreatment conditions and 2.79% lignin removal at 115 ℃. It is therefore an object of the present invention to provide a method for promoting the deconstruction of lignocellulose by a neutral eutectic solvent.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention aims to provide a method for pretreating lignocellulose by using a Lewis base-assisted neutral eutectic solvent.
The purpose of the invention is realized by at least one of the following technical schemes:
a method of pre-treating lignocellulose with a lewis base-assisted neutral eutectic solvent, comprising the steps of:
(1) placing the air-dried and crushed lignocellulose raw material into a prepared eutectic solvent, and then adding Lewis base;
(2) heating the solid-liquid mixture to obtain a mixed solution;
(3) vacuum filtering the mixed solution, and washing residues with washing solution to obtain solid fraction and liquid fraction rich in cellulose;
(4) and (4) carrying out an acid precipitation method on the liquid fraction to obtain regenerated lignin.
Further, the lignocellulose raw material in the step (1) is needle-leaved wood, broad-leaved wood, bamboo wood or grass raw material,
more preferably, the lignocellulose raw material is agricultural and forestry waste corn stalks.
Further, the wood fiber raw material in the step (1) is crushed and then screened by a 40-60-mesh sieve.
Further, the eutectic solvent in the step (1) is a mixture of ethylene glycol and choline chloride; preferably, the molar ratio of the ethylene glycol to the choline chloride is (2-3): 1,
further, the solid-to-liquid ratio of the lignocellulose raw material and the eutectic solvent in the step (1) is 1: 10-1: 20.
Further, the lewis base in step (1) includes at least one of sodium carbonate, sodium acetate and sodium sulfite;
further, the addition amount of the lewis base in the step (1) accounts for 15 to 25 percent of the lignocellulose raw material.
Further, the pretreatment conditions in the step (2) are as follows: the temperature is 100-120 ℃, and the time is 2-3 h
Further, the washing solution in the step (3) is acetone, ethanol or water. More preferably, the washing solution is a mixture of ethanol/water (v/v ═ 1: 1).
Further, the liquid part of the lignin removed in the step (4) is recycled after concentration and dehydration.
Furthermore, the eutectic solvent aqueous solution is recycled after rotary evaporation and dehydration.
The lignocellulose pretreatment method provided by the invention can be applied to the technical field of biofuel preparation or pulping and papermaking.
Compared with the prior art, the invention has the following advantages and effects:
(1) the pretreatment method provided by the invention has the advantages of low cost, no toxicity, easy synthesis, recycling and effective deconstruction of lignocellulose;
(2) the pretreatment method provided by the invention can effectively remove hemicellulose and lignin and obviously improve the accessibility of the cellulose. And the provided alkaline environment can protect the end group of the cellulose, and compared with other acidic pretreatments, the method can retain most of the cellulose, and is favorable for saccharification and enzymolysis in the later period.
(3) The pretreatment method provided by the invention has good application prospect in the fields of biofuel preparation or pulping and papermaking.
Detailed Description
The present invention is described below by way of examples, but the embodiments of the present invention are not limited by the examples, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and they are included in the scope of the present invention. The reagents or apparatus used are not indicated to the manufacturer, and are considered to be conventional products available by commercial purchase.
Example 1
A method of pre-treating lignocellulose with a lewis base-assisted neutral eutectic solvent, comprising the steps of:
mixing ethylene glycol and choline chloride according to a molar ratio of 2:1 to obtain a liquid eutectic solvent. And (3) placing the oven-dried corn straws which are sieved by a 40-mesh sieve into a eutectic solvent, wherein the mass ratio of the corn straws to the eutectic solvent is 1: 10. Then adding sodium acetate (15% of oven dried corn stalk) and mixing them uniformly. And (3) adding the solid-liquid mixture into a normal pressure reaction kettle for heating pretreatment, wherein the treatment time is 2 hours, the treatment temperature is 100 ℃, and the mixed solution after eutectic solvent treatment is obtained. After pretreatment, the mixture was vacuum filtered and washed with ethanol/water (v/v ═ 1:1) to give a solid residue (cellulose rich fraction) and a liquid fraction. The regenerated lignin in the liquid fraction was collected by acid precipitation.
Example 2
A method of pre-treating lignocellulose with a lewis base-assisted neutral eutectic solvent, comprising the steps of:
mixing ethylene glycol and choline chloride according to a molar ratio of 3:1 to obtain a liquid eutectic solvent. And (3) placing the oven-dried corn straws which are sieved by a 40-mesh sieve into a eutectic solvent, wherein the mass ratio of the corn straws to the eutectic solvent is 1: 15. Sodium sulfite (20% of oven dried corn stover) was then added and mixed well. And (3) adding the solid-liquid mixture into a normal pressure reaction kettle for heating pretreatment, wherein the treatment time is 2 hours, the treatment temperature is 110 ℃, and a mixed solution after eutectic solvent treatment is obtained. After pretreatment, the mixture was vacuum filtered and washed with ethanol/water (v/v ═ 1:1) to give a solid residue (cellulose rich fraction) and a liquid fraction. The regenerated lignin in the liquid fraction was collected by acid precipitation.
Example 3
A method of pre-treating lignocellulose with a lewis base-assisted neutral eutectic solvent, comprising the steps of:
mixing ethylene glycol and choline chloride according to a molar ratio of 2:1 to obtain a liquid eutectic solvent. And (3) placing the oven-dried corn straws which are sieved by a 40-mesh sieve into a eutectic solvent, wherein the mass ratio of the corn straws to the eutectic solvent is 1: 20. Then sodium carbonate (25% of oven dried corn stover) was added and mixed well. And (3) adding the solid-liquid mixture into a normal pressure reaction kettle for heating pretreatment, wherein the treatment time is 3h, the treatment temperature is 120 ℃, and a mixed solution after eutectic solvent treatment is obtained. After pretreatment, the mixture was vacuum filtered and washed with ethanol/water (v/v ═ 1:1) to give a solid residue (cellulose rich fraction) and a liquid fraction. The regenerated lignin in the liquid fraction was collected by acid precipitation.
Example 4
After the treatment of lignocellulose by the Lewis base assisted neutral eutectic solvent, the recycling of the lignocellulose comprises the following steps:
the liquid fraction from which lignin precipitated in example 3 was evaporated in a rotary evaporator at 60 c to remove ethanol/water. The recovered lewis base/eutectic solvent was then used without further purification to pretreat the corn stover as described in example 3, and was thus recycled for 4 times.
Comparative examples
To further illustrate the effect of lewis base on the efficiency of pretreatment of neutral eutectic solvents, lignocellulose was pretreated with only neutral eutectic solvents, as a comparative example, comprising the following steps:
mixing ethylene glycol and choline chloride according to a molar ratio of 2:1 to obtain a liquid eutectic solvent. And (3) placing the oven-dried corn straws which are sieved by a 40-mesh sieve into a eutectic solvent, wherein the mass ratio of the corn straws to the eutectic solvent is 1: 20. And (3) adding the solid-liquid mixture into a normal pressure reaction kettle for heating pretreatment, wherein the treatment time is 3h, the treatment temperature is 120 ℃, and a mixed solution after eutectic solvent treatment is obtained. After pretreatment, the mixture was vacuum filtered and washed with ethanol/water (v/v ═ 1:1) to give a solid residue (cellulose rich fraction) and a liquid fraction. The regenerated lignin in the liquid fraction was collected by acid precipitation.
Effect verification
The pretreated substrate was analyzed for compositional changes according to the national renewable energy laboratory standard NREL analysis method.
And (3) enzymolysis saccharification: 300mg of the cellulose residue was weighed into a centrifuge tube, and 15mL of 0.05mol/L, PH ═ 4.8 citric acid-sodium citrate buffer was added in an amount of 15FPU/g substrate cellulase. Mixing, placing in shaking table (50 deg.C, 150r/min), saccharifying for 72 hr, taking out, and measuring sugar release amount of reaction solution by ion chromatography.
TABLE 1 composition change and saccharification efficiency (%)
As can be seen from the data in Table 1, the lignocellulose pretreatment method disclosed by the embodiment of the invention has the characteristics of low cost, no toxicity and the like, is simple and feasible in preparation method, has a good deconstruction effect on lignocellulose, has the enzymolysis saccharification efficiency which is 3.8-4.9 times that of untreated lignocellulose, has the saccharification efficiency which is still 85.5% after four cycles, has a good recycling effect, and has a wide application prospect in the fields of biomass fuel and pulping and papermaking.
The above examples are only preferred embodiments of the present invention, which are intended to be illustrative and not limiting, and those skilled in the art should understand that they can make various changes, substitutions and alterations without departing from the spirit and scope of the invention.
Claims (10)
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| CN115160591A (en) * | 2022-07-04 | 2022-10-11 | 中国林业科学研究院林产化学工业研究所 | Method for quickly and efficiently deconstructing lignocellulose by using alkaline eutectic solvent |
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