CN105126727A - Micro emulsion reactor used for lignin catalytic depolymerization - Google Patents
Micro emulsion reactor used for lignin catalytic depolymerization Download PDFInfo
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- CN105126727A CN105126727A CN201510439282.XA CN201510439282A CN105126727A CN 105126727 A CN105126727 A CN 105126727A CN 201510439282 A CN201510439282 A CN 201510439282A CN 105126727 A CN105126727 A CN 105126727A
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Abstract
The invention discloses a micro emulsion reactor used for lignin catalytic depolymerization. The micro emulsion reactor is used through following steps: 1) mixing and stirring organically-soluble lignin, sulfonic acid-functionalized acidic ionic liquid, a hydrocarbon compound, a hydrophobic organic solvent and deionized water; 2) performing a hydrothermal reaction at 150-300 DEG C; and 3) after the reaction is carried out for 5-120 min, filtering a reaction liquid, performing liquid separation to obtain an oil phase containing phenols, a water phase containing the ionic liquid and solid residues. The micro emulsion reactor is high in liquefaction rate of lignin and selectivity. After the reaction, because the lignin is reduced in hydrophilicity, the reaction spontaneously forms two phases, so that the solid residues are obtained through filtration and the water phase being rich in the ionic liquid is obtained through the liquid separation. Extra water is removed in a rotary evaporation manner to recycle the ionic liquid for the next reaction directly. The reactor has a significant process strengthening effect on the depolymerization of lignin.
Description
Technical field
The invention belongs to catalytic lignin depolymerization and prepare high value added product technical field, be specifically related to a kind of micro emulsion reactor for catalytic lignin depolymerization.
Background technology
Living beings are the energy that uniquely can provide carbon compound in regenerative resource, and have the remarkable advantages such as " neutral carbon ", wide material sources, annual production be huge, in whole energy resource system, occupy critical role.The key component of living beings comprises cellulose, hemicellulose and lignin.In recent years, by chemistry or the method Efficient Conversion cellulose such as biological with hemicellulose prepares bio-fuel and platform chemicals obtains good development.But as the second largest component lignin of living beings, be also the renewable resource that occurring in nature uniquely can provide aromatic, because the complexity of its structure and uncertainty become the difficult point of biomass conversion process. simultaneouslyThe lignin major part obtained from paper-making pulping night is every year used to combustion heat supplying, only has about 2% for other aspects, causes the waste of environmental pollution and resource.
Current lignin is micromolecular compound mainly through technical transforms such as pyrolysis, oxidation, liquefaction, hydrolysis.Wherein, catalyst is the key factor in lignin conversion process.Partenheimer etc. with Co/Mn/Zr/Br be catalyst at air, in aqueous acetic acid system, catalytic oxidation lignin obtains 18 kinds of aromatics such as parahydroxyben-zaldehyde, P-hydroxybenzoic acid, vanillic aldehyde, vanillic acid, syringaldehyde and syringic acid.Xu etc. utilize formic acid for hydrogen source, and Pt/C is that catalyst is degraded the organic molten lignin of switchgrass in ethanolic solution.Research finds, can promote under this system that macromolecular compound is transformed into Small molecular liquid product, reaction time has larger impact to the distribution of product and the character of liquid product, after reaction 4h, the lignin of 21% is transformed into 7 kinds of primary products, and after 20h, the relative molecular mass of the lignin of 76% reduces, find that in liquid product, O/C is than reduction by 50% by elementary analysis, and H/C is than increase by 10%.But because lignin is that solid catalyst is difficult to and substrate contact by alkyl phenol unit space net structure crosslinked together, reaction needed is carried out under comparatively exacting terms.In recent years, ionic liquid, owing to having feature and the good advantage such as lignin dissolution ability of homogeneous phase and heterogeneous catalyst, becomes study hotspot.2007, the research such as Pu found that the ionic liquid containing Methylsulfate and three fluosulfonic acid has solubility property to the lignin extracted in Southern Pine NBSK, thus ionic liquid is introduced the research of lignin.But current catalyzed conversion system intermediate ion liquid is difficult to and product separation, is unfavorable for again recycling.
Microemulsion is that one comprises aqueous phase, the thermodynamic stable system of oil phase and surfactant, because it can overcome inconsistent problem between traditional system Semi-polarity and nonpolar reactant.Hydrophilic and oleophilic substance is dissolved in aqueous phase and oil phase respectively, and assembles at oil-water interfaces, promotes the carrying out of reaction and improves selective.In recent years in drug delivery, the fields such as the preparation of nano particle receive larger concern.Micro emulsion reactor be a kind of microcosmic composition in simultaneously containing the required component that responds, be the microscopic pattern of macroreaction.
Summary of the invention
In order to solve the shortcoming and defect part of prior art, primary and foremost purpose of the present invention is to provide a kind of micro emulsion reactor for catalytic lignin depolymerization, realizes the efficient depolymerization of lignin and ionic-liquid catalyst and product separation.The object of the invention is achieved through the following technical solutions:
A kind of micro emulsion reactor for catalytic lignin depolymerization, comprise the following steps: organic molten lignin, sulfonic acid funtionalized acidic ion liquid (catalyst), hydrocarbon (additive), hydrophobic organic solvent and deionized water are mixed, stir, hydro-thermal reaction is carried out in 150-300 DEG C, after reaction 5min-2h, by reacting liquid filtering, separatory, obtains containing the oil phase of phenols, containing ionic liquid aqueous phase and solid residue.
After reaction, because lignin hydrophily weakens, the spontaneous formation two-phase of reactant liquor, obtain solid residue by filtering, separatory obtains the aqueous phase being rich in ionic liquid, revolves and steams removing superfluous water recovery ionic liquid, be directly used in and react next time.
Described ionic liquid has the cation with sulfonic acid group of imidazoles containing alkyl chain or pyridines; And containing chlorion, bisulfate ion, TFMS root or hydrogen phosphate be anion ion liquid.
Described sulfonic acid funtionalized acidic ion liquid obtains as follows:
(1) the N-alkyl imidazole/pyridine and the butane sultone that take equimolar amounts react 24 ~ 48h under 40-60 DEG C of condition; React rear washed with diethylether, vacuum drying at 40 ~ 70 DEG C, obtain white solid inner salt;
(2) acid of equimolar amounts and above-mentioned prepared inner salt is taken; Acid is added drop-wise in inner salt while stirring, 40-60 DEG C of reaction 24 ~ 48h;
(3) wash with absolute ether after reaction, vacuum drying 12 ~ 48h at 60 ~ 80 DEG C, obtains sulfonic acid funtionalized ionic liquid.
Described acid is 98% concentrated sulfuric acid, 36% concentrated hydrochloric acid or TFMS; The carbon chain lengths of described N-alkyl imidazole is 1 ~ 6 carbon atom.
Described organic molten lignin obtains as follows:
(1) pretreatment of agricultural wastes: adopt the method for mechanical crushing to be crushed to below 60 orders by after agricultural wastes fully drying, and by deionized water by abundant drying for standby after its soluble component and ash content washing;
(2) extraction of organic molten lignin: by the H of 1 ~ 100 mass parts
2sO
4fully mix with the agricultural wastes of 10 ~ 2000 mass parts, pass into inert atmosphere, reaction temperature is 100 ~ 200 DEG C, after reaction, by being separated and vacuum drying, namely obtains highly purified organic molten lignin.
In the organic molten lignin of 1g, the consumption of deionized water is 4 ~ 400mL, and the consumption of n-butanol is 4 ~ 400mL, and the consumption of alkane is 0.2 ~ 80mL, and the consumption of ionic liquid is 0.6 ~ 40mmol.
The temperature of described hydro-thermal reaction is 200 ~ 280 DEG C, and the reaction time is 0.25 ~ 1h.
Described hydrocarbon is n-hexane, cyclohexane or toluene; Hydrophobic organic solvent is n-butanol or MIBK.
Described vacuum drying temperature is 60 ~ 80 DEG C, and the time is 24 ~ 48h.
The inventive method adopts sulfonic acid funtionalized acidic ionic liquid catalysts, by building the microemulsion reactor being surfactant with organic molten lignin, making lignin and ionic-liquid catalyst in two-phase interface enrichment, lignin being carried out to the depolymerization of original position.After reaction, due to reducing from surface-active of lignin, the spontaneous formation two-phase of system, overcomes the breakdown of emulsion process of classical microemulsion system and the separation process of surfactant and product.Ionic-liquid catalyst and product separation can be reclaimed ionic-liquid catalyst by simple isolated by filtration.This system overcomes conventional ionic liquid and is difficult to and the shortcomings such as the break milk separation of product separation and microemulsion system, and has good process intensification and catalyzed conversion effect.
The present invention compared with prior art, has following advantage and beneficial effect:
(1) utilize the surface-active in-situ construction microemulsion reactor of lignin first, and efficiently liquefy under ionic liquid condition, liquefied fraction and selective all higher.
(2), after lignin degradation, the spontaneous breakdown of emulsion of microemulsion does not need the program crash Sturctures of Microemulsions through complexity.
(3) ionic liquid easily reclaims: be separated with organic phase in aqueous phase enrichment after the catalyst reaction that the present invention is used, and removal process is simple, very easily with separation of products.
Accompanying drawing explanation
Fig. 1 is the GC-MS figure of volatile products in the embodiment of the present invention 4, BSbimHSO
4for catalyst (a), catalyst-free (b).
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited thereto.
Embodiment 1
1, ionic liquid BSmimHSO
4preparation:
(1) the N-alkyl imidazole and the butane sultone that take equimolar amounts react 24h under 50 DEG C of conditions; React rear washed with diethylether, vacuum drying at 60 DEG C, obtain white solid inner salt; The carbon chain lengths of described N-alkyl imidazole is 1 ~ 6 carbon atom;
(2) acid of equimolar amounts and above-mentioned prepared inner salt is taken; The concentrated sulfuric acid is added drop-wise in inner salt while stirring, 50 DEG C of reaction 48h;
(3) wash with absolute ether after reaction, vacuum drying 48h at 80 DEG C, obtains ionic liquid BSmimHSO
4.
2, the preparation of bagasse lignin:
(1) pretreatment of agricultural wastes: adopt the method for mechanical crushing to be crushed to below 60 orders by after bagasse fully drying, and by deionized water by abundant drying for standby after its soluble component and ash content washing;
(2) extraction of organic molten lignin: by the H of 1 mass parts
2sO
4fully mix with the bagasse of 15 mass parts, pass into inert atmosphere, reaction temperature is 120 DEG C, after reaction, by being separated and vacuum drying, namely obtains highly purified bagasse lignin.
3, for the micro emulsion reactor of catalytic lignin depolymerization:
Accurately take 0.5g bagasse lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmol1-(4-sulfonic acid butyl)-3-methylimidazolium hydrogen sulphate salt (BSmimHSO
4) join in 100mL autoclave, react 0.5h at 250 DEG C.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 86.1%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with gas chromatograph-mass spectrometer (GC-MS) (GC-MS) is 19.22mg/g.
Embodiment 2
Accurately take 0.5g bagasse lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmol1-(4-sulfonic acid butyl)-3-ethyl imidazol(e) disulfate (BSeimHSO
4) join in 100mL autoclave, react 0.5h at 250 DEG C.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 87.9%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 20.14mg/g.
Embodiment 3
Accurately take 0.5g bagasse lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmol1-(4-sulfonic acid butyl)-3-propyl imidazole disulfate (BSpimHSO
4) join in 100mL autoclave, react 0.5h at 250 DEG C.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 88.6%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 26.38mg/g.
Embodiment 4
Accurately take 0.5g bagasse lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmol1-(4-sulfonic acid butyl)-3-butyl imidazole disulfate (BSbimHSO
4) join in 100mL autoclave, react 0.5h at 250 DEG C.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 89.1%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 29.60mg/g.
Embodiment 5
Accurately take 0.5g cassava lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmolBSbimHSO
4join in 100mL autoclave, at 250 DEG C, react 0.5h.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 94.8%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 17.41mg/g.
Embodiment 6
Accurately take 0.5g RICE STRAW LIGNIN, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmolBSbimHSO
4join in 100mL autoclave, at 250 DEG C, react 0.5h.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 94.8%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 23.40mg/g.
Embodiment 7
Accurately take 0.5g cornstalk lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmolBSbimHSO
4join in 100mL autoclave, at 250 DEG C, react 0.5h.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 91.1%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 42.06mg/g.
Embodiment 8
Accurately take 0.5g Corn cob lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmolBSbimHSO
4join in 100mL autoclave, at 250 DEG C, react 0.5h.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 93.0%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 47.52mg/g.
Embodiment 9
Accurately take 0.5g bagasse lignin, 10mL n-butanol, 30mL deionized water, 2mL n-hexane, 3.0mmolBSbimHSO
4join in 100mL autoclave, at 250 DEG C, react 0.5h.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 66.7%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 11.94mg/g.
Embodiment 10
Accurately take 0.5g bagasse lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 2.0mmolBSbimHSO
4join in 100mL autoclave, at 250 DEG C, react 0.5h.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 86.0%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 17.84mg/g.
Embodiment 11
Accurately take 0.5g bagasse lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmolBSbimHSO
4join in 100mL autoclave, at 230 DEG C, react 0.5h.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 90.6%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 11.82mg/g.
Embodiment 12
Accurately take 0.5g bagasse lignin, 20mL n-butanol, 20mL deionized water, 2mL n-hexane, 3.0mmolBSbimHSO
4join in 100mL autoclave, at 250 DEG C, react 1.0h.After reaction, be separated by reacting liquid filtering, obtain solid residue, 60 DEG C of vacuum drying 24h, calculating liquefied fraction is 85.6%.Carry out separatory to n-butanol water, n-butanol deionized water extracts 3 times, and is settled to 100mL with n-butanol, and measuring major phenolic monomer yield with GC-MS is 21.70mg/g.
Embodiment 13
The present embodiment step is with embodiment 4, and directly carry out next step reaction after the aqueous phase being rich in ionic liquid after reaction is boiled off unnecessary water, investigate the reusability of ionic-liquid catalyst, result is as shown in table 1.As can be seen from Table 1, catalyst has good repeat performance, and after 3 circulations, catalytic activity does not significantly reduce.
The reusability of table 1 sulfonic acid funtionalized ionic liquid
Above-described embodiment is the present invention's preferably embodiment; but embodiments of the present invention are not restricted to the described embodiments; change, the modification done under other any does not deviate from Spirit Essence of the present invention and principle, substitute, combine, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (10)
1. the micro emulsion reactor for catalytic lignin depolymerization, it is characterized in that, comprise the following steps: organic molten lignin, sulfonic acid funtionalized acidic ion liquid, hydrocarbon, hydrophobic organic solvent and deionized water are mixed, stir, hydro-thermal reaction is carried out, after reaction 5min-2h, by reacting liquid filtering in 150-300 DEG C, separatory, obtains containing the oil phase of phenols, containing ionic liquid aqueous phase and solid residue.
2. micro emulsion reactor according to claim 1, is characterized in that, described ionic liquid has the cation with sulfonic acid group of imidazoles containing alkyl chain or pyridines; And containing chlorion, bisulfate ion, TFMS root or hydrogen phosphate be anion ion liquid.
3. micro emulsion reactor according to claim 2, is characterized in that, the cation of described ionic liquid has the long alkyl chains of 1-6.
4. the micro emulsion reactor according to claim 1 or 2 or 3, is characterized in that, described sulfonic acid funtionalized acidic ion liquid obtains as follows:
(1) the N-alkyl imidazole/pyridine and the butane sultone that take equimolar amounts react 24 ~ 48h under 40-60 DEG C of condition; React rear washed with diethylether, vacuum drying at 40 ~ 70 DEG C, obtain white solid inner salt;
(2) acid of equimolar amounts and above-mentioned prepared inner salt is taken; Acid is added drop-wise in inner salt while stirring, 40-60 DEG C of reaction 24 ~ 48h;
(3) wash with absolute ether after reaction, vacuum drying 12 ~ 48h at 60 ~ 80 DEG C, obtains sulfonic acid funtionalized ionic liquid.
5. micro emulsion reactor according to claim 4, is characterized in that, described acid is 98% concentrated sulfuric acid, 36% concentrated hydrochloric acid or TFMS; The carbon chain lengths of described N-alkyl imidazole is 1 ~ 6 carbon atom.
6. the micro emulsion reactor according to claim 1 or 2 or 3, is characterized in that, described organic molten lignin obtains as follows:
(1) pretreatment of agricultural wastes: adopt the method for mechanical crushing to be crushed to below 60 orders by after agricultural wastes fully drying, and by deionized water by abundant drying for standby after its soluble component and ash content washing;
(2) extraction of organic molten lignin: by the H of 1 ~ 100 mass parts
2sO
4fully mix with the agricultural wastes of 10 ~ 2000 mass parts, pass into inert atmosphere, reaction temperature is 100 ~ 200 DEG C, after reaction, by being separated and vacuum drying, namely obtains highly purified organic molten lignin.
7. the micro emulsion reactor according to claim 1 or 2 or 3, is characterized in that, in the organic molten lignin of 1g, the consumption of deionized water is 4 ~ 400mL, the consumption of n-butanol is 4 ~ 400mL, and the consumption of alkane is 0.2 ~ 80mL, and the consumption of ionic liquid is 0.6 ~ 40mmol.
8. the micro emulsion reactor according to claim 1 or 2 or 3, is characterized in that, the temperature of described hydro-thermal reaction is 200 ~ 280 DEG C, and the reaction time is 0.25 ~ 1h.
9. the micro emulsion reactor according to claim 1 or 2 or 3, is characterized in that, described hydrocarbon is n-hexane, cyclohexane or toluene; Hydrophobic organic solvent is n-butanol or MIBK.
10. the micro emulsion reactor according to claim 1 or 2 or 3, it is characterized in that, described vacuum drying temperature is 60 ~ 80 DEG C, the time is 24 ~ 48h.
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|---|---|---|---|---|
| CN107573225A (en) * | 2017-09-11 | 2018-01-12 | 华南理工大学 | A kind of method that hydrogenolysis lignin prepares single phenolic compound in water/oily diphasic system |
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| CN102060642A (en) * | 2010-10-27 | 2011-05-18 | 华南理工大学 | Method for carrying out catalytic conversion with high efficiency on cellulose at low temperature by utilizing compound ion liquid system |
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| CN102911142A (en) * | 2012-10-24 | 2013-02-06 | 复旦大学 | Method for preparing 5-hydroxymethylfurfural |
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| CN102060642A (en) * | 2010-10-27 | 2011-05-18 | 华南理工大学 | Method for carrying out catalytic conversion with high efficiency on cellulose at low temperature by utilizing compound ion liquid system |
| CN102321251A (en) * | 2011-05-27 | 2012-01-18 | 华南理工大学 | Method for separating xylogen from agricultural waste by using compound ion liquid |
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| Title |
|---|
| JINXING LONG ET AL.: ""[C4H8SO3 Hmim]HSO4 as an efficient catalyst for direct liquefaction of bagasse lignin Decomposition properties of the inner structural units"", 《CHEMICAL ENGINEERING SCIENCE》 * |
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| CN107573225A (en) * | 2017-09-11 | 2018-01-12 | 华南理工大学 | A kind of method that hydrogenolysis lignin prepares single phenolic compound in water/oily diphasic system |
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