CN104073278A - Method for converting lignin into liquid fuel through adopting two-step method - Google Patents
Method for converting lignin into liquid fuel through adopting two-step method Download PDFInfo
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- CN104073278A CN104073278A CN201410335709.7A CN201410335709A CN104073278A CN 104073278 A CN104073278 A CN 104073278A CN 201410335709 A CN201410335709 A CN 201410335709A CN 104073278 A CN104073278 A CN 104073278A
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Abstract
The invention discloses a method for converting lignin into liquid fuel through adopting a two-step method, and relates to a method for converting biomass into liquid fuel. The method comprises the steps as follows: firstly, lignin, a hydrogenation catalyst and an alkaline solution are put into a reaction kettle for depolymerization reaction, an HCL solution and ethyl acetate are added after the reaction for filtration and solid drying, liquor separation of the oil phase and water phase is carried out, and anhydrous magnesium sulfate is put into the oil phase for filtration and rotary steaming; secondly, the lignin, the hydrogenation catalyst and water are put into the reaction kettle for reaction and ethyl acetate is put into the solution for filtration, a catalyst for recycling is dried, and the liquid rotary steaming is carried out. Through adopting the alkaline solution to degrade the lignin, the liquid product yield is increased, the production rate of phenols in a liquid product is increased, and the yield of solid residues is reduced; moreover, through putting the catalytic hydrogenation in the water phase in lignin phenols, the selectivity of hydrocarbon of a product is high enough to reach 92.92 percent, the selectivity of naphthenic hydrocarbon in the hydrocarbon of the product reaches 63.58 percent, as a result, liquid products high in yield are obtained and the hydro-conversion of liquid products is easier to realize, and hydrocarbon fuel with high selectivity is obtained.
Description
Technical field
The present invention relates to a kind of method that Wood Adhesives from Biomass is liquid fuel, particularly relate to a kind of method that xylogen two-step approach is converted into liquid fuel.
Background technology
In the face of the exhaustion day by day of fossil energy in global range, exploitation renewable energy source substitutes fossil energy with part, and maintaining human social becomes the problem that people more and more pay close attention to.Biomass energy is uniquely in all renewable energy sources can be converted into liquid, gas and solid-fuelled renewable energy source, and can partly substitute fossil energy, therefore, develop and utilize biomass energy to have great meaning for setting up resource-conserving and environment-friendly society.Biomass three major polymers: cellulose, hemicellulose and three kinds of components of xylogen form.At present, the utilization of Mierocrystalline cellulose and hemicellulose is mainly to obtain respectively bio-ethanol and hydroxymethylfurfural or other furfuran compound by fermentation and catalyzed conversion, and the utilization of xylogen also exists some difficulties.Although xylogen only accounts for 15%～30% of whole biomass components, calorific value but accounts for 40%, is on the earth, to be rich in the renewable resources that aromatic hydrocarbons structure is maximum, is also unique non-oil resource that renewable aryl compound can be provided.
In recent years, the catalyzed degradation of xylogen is prepared the focus that phenolic compound becomes research gradually.The phenolic compound that degraded obtains can obtain various free phenolss through further separation, but owing to also not having at present suitable separation means that they are completely separated, and because phenols is generally all applied to the industries such as medicine intermediate, tobacco, essence and flavoring agent, demand is less relatively, therefore, it can not be more considerable economic benefit by lignin conversion completely that lignin degradation is prepared phenolic compound, is necessary to open up a new path.Using lignin phenol as hardware and software platform compound, and being further converted to the hydrocarbon fuel that added value is higher, demand is larger is a method of utilizing with potential value.
Xylogen two-step approach is converted into hydro carbons also relevant research in the past.Method is first by xylogen depolymerization in the alkaline solution that comprises alcohol (methyl alcohol, ethanol), and then uses CoMo/Al
2o
3carry out catalytic hydrogenation processing, product is mainly C
7-C
11alkylbenzene, polyalkylated naphthenic hydrocarbon and alkylnaphthalene.Another kind method is in two-step approach, all to using water as solvent, usings Ru/C (or Pd/C) and phosphoric acid to carry out depolymerization-hydrogenation as catalyzer, contains part C in product
9, C
13-18naphthenic hydrocarbon.
Yet all there is problem separately: first method CoMo/Al in these two kinds of methods at present
2o
3need vulcanized gas, may pollution products, and also catalyzer can coking; Second method, due to Shui Bu dissolved lignin, can cause depolymerization efficiency lower, and solid residue yield is higher.Therefore, how can increase product liquid yield, reducing solid residue yield, to improve again hydrocarbon selective be the key that two-step approach is prepared hydrocarbon fuel simultaneously.
Summary of the invention
The object of this invention is to provide the product liquid (lignin phenol) that can obtain higher yields, can realize relatively easily its hydrocracking again, obtain a kind of method that xylogen two-step approach is converted into liquid fuel of highly selective hydrocarbon fuel.
The present invention includes following steps:
1) xylogen, hydrogenation catalyst and basic solution are joined in reactor and carry out depolymerization reaction, after reaction, add again HCl solution and ethyl acetate, filter, solid drying, liquid separation oil phase and water add anhydrous magnesium sulfate in oil phase, revolve steaming after filtration;
2) lignin phenol, hydrogenation catalyst and water are joined to reaction kettle for reaction, then add ethyl acetate, filter, catalyzer is dry, reclaims, and liquid revolves steaming, obtains liquid fuel.
In step 1) in, described basic solution can be selected from alkaline aqueous solution or alkaline alcohol/aqueous solution; In described alkaline alcohol/aqueous solution, the volumetric concentration of alcohol can be 15%～85%, and preferably 30%～70%; The alkali using in basic solution can be selected from least one in sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, magnesium hydroxide, salt of wormwood etc.; The mass percentage concentration of alkali can be 1%～8%, and preferably 1%～5%; The condition of described depolymerization reaction can be: 250～350 ℃ of temperature, initial hydrogen pressure 1～5MPa, time 0.5～8h; It is 10%HCl solution that described HCl solution can adopt mass concentration; Described liquid separation oil phase can adopt the separated oil phase of separating funnel and water with water.
In step 2) in, described hydrogenation catalyst can adopt dual-function catalyst or single nickel series hydrogenating catalyst; Described dual-function catalyst can adopt the combination of hydrogenation catalyst and acid catalyst, hydrogenation catalyst can be selected from a kind of in the noble metal catalysts such as Pd/C, Ru/C, and acid catalyst can be selected from a kind of in hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, HZSM-5 molecular sieve etc.; The preferably combination of noble metal catalyst and phosphoric acid; The mass concentration of acid can be 0.5%～4.0%, and preferably 1.0%～2.5%; Described single nickel series hydrogenating catalyst can be selected from Raney Ni, Ni/SiO
2, Ni/ZrO
2, Ni/SiO
2-ZrO
2a kind of Deng in catalyzer; The charge capacity of Ni can be 5%～50%, and preferably 10%～30%; The condition of described reaction can be: 250～320 ℃ of temperature, pressure 1～5MPa, time 1～8h.
Beneficial effect of the present invention is as follows:
Alkaline solution lignin degrading can increase the yield of product liquid, especially improves the productive rate of phenols in product liquid, and can reduce the yield of solid residue.
Lignin phenol is shortening in water, and products therefrom hydrocarbon selective is high, can reach 92.92%, and wherein the selectivity of naphthenic hydrocarbon reaches 63.58%.
Embodiment
Xylogen, hydrogenation catalyst and 100ml basic solution are joined in reactor, pass into respectively nitrogen and hydrogen each 3 times after question response still good seal, the nitrogen of discharging the air in reactor and passing into, finally passes into hydrogen to required pressure.Regulate respectively temperature of reaction and mixing speed, then start reaction.After reaction finishes, reactor being put into ice-water bath is cooled to below 40 ℃, then hydrogen in reactor is discharged, and open reactor and take out degraded product, then add ethyl acetate to extract oil phase, now degraded product is divided into two-phase: oil phase and water (solid residue is also therein).Then add 10%HCl solution, shake up, standing, with PH test paper, survey product liquid potential of hydrogen, until PH=1～2.Then degraded product filters and to be divided into solid and liquid, and solid is put into the calculating yield of weighing after the dry 24h of moisture eliminator, the separated oil phase of separating funnel and water for liquid, and water is abandoned it, adds appropriate anhydrous magnesium sulfate in oil phase, shakes up standing 2h.Last filtering separation anhydrous magnesium sulfate, oil phase revolves the calculated yield of weighing after steaming.The liquid that degraded obtains, productive rate solid, gas calculate by following formula:
Y
oil=[(M
oil/ g)/(M
xylogen/ g)] * 100%
Y
gu=[(M
gu/ g)/(M
xylogen/ g)] * 100%
Y
gas=1-Y
oil-Y
gu
S
phenol=∑ A
i(A
irefer to the corresponding peak area of the detected every kind of phenols of GC-MS)
Wherein, M
oil, M
gu, M
xylogenrepresent respectively the quality of bio oil, solid, xylogen; S
phenolrepresent the selectivity of phenolic compound.
Oil phase is that lignin phenol is extracted with ethyl acetate rear extraction portion and divides and revolve steaming, weighs and obtains the quality of oil phase, and then be extracted with ethyl acetate and join in reactor, then reactor is put into water-bath, regulates water-bath temperature to 70 ℃, steams ethyl acetate.After in autoclave, add a certain amount of noble metal hydrogenation catalyst+acid catalyst (or single nickel series hydrogenating catalyst) and 100ml water to carry out aqueous catalysis hydrogenation reaction.Add after completion of the reaction ethyl acetate to extract oil phase, then filter, after catalyzer is dry, reclaim, the separated oil phase of separating funnel and water for liquid, water is abandoned it, and oil phase revolves steaming.
S
hydrocarbon=∑ A
i(A
irefer to the corresponding peak area of the detected every kind of hydro carbons of GC-MS)
S
alcohol/
ketone=∑ A
i(A
irefer to the corresponding peak area of the detected every kind of alcohol/ketone of GC-MS)
Wherein, S
hydrocarbonand S
alcohol/
ketonerepresent respectively the selectivity of phenolic compound alcohol/ketone compounds.
Below provide specific embodiment.
Embodiment 1
According to above-mentioned experimental technique, select noble metal catalyst as hydrogenation catalyst, set reaction conditions: liquid-solid ratio is 100: 3,280 ℃ of temperature of reaction, initial hydrogen pressure 4MPa, reaction times 2h, mixing speed 300r/min.Xylogen degradation results in aqueous sodium hydroxide solution is as shown in table 1.
Table 1
According to above-mentioned experimental technique, select noble metal catalyst+acid catalyst as hydrogenation catalyst, set reaction conditions: 270 ℃ of temperature of reaction, initial hydrogen pressure 4MPa, reaction times 6h, mixing speed 600r/min.The composition of lignin phenol and their hydrogenation products are as shown in table 2.
Table 2
Embodiment 2
Similar to embodiment 1 method, select noble metal catalyst as hydrogenation catalyst, set reaction conditions: liquid-solid ratio is 100: 3,270 ℃ of temperature of reaction, initial hydrogen pressure 4MPa, reaction times 8h, mixing speed 300r/min.Xylogen degradation results in sodium hydroxide ethanol/water solution is as shown in table 3.
Table 3
Similar to embodiment 1 method, select noble metal catalyst+acid catalyst as hydrogenation catalyst, set reaction conditions: 270 ℃ of temperature of reaction, initial hydrogen pressure 4MPa, reaction times 6h, mixing speed 600r/min.The composition of lignin phenol and their hydrogenation products are as shown in table 4.
Table 4
Embodiment 3
Similar to embodiment 1 method, select single nickel catalyst as hydrogenation catalyst, set reaction conditions: liquid-solid ratio is 100: 3,300 ℃ of temperature of reaction, initial hydrogen pressure 2MPa, reaction times 4h, mixing speed 300r/min.Xylogen degradation results in aqueous sodium hydroxide solution is as shown in table 5.
Table 5
Similar to embodiment 1 method, select single nickel catalyst as hydrogenation catalyst, set reaction conditions: 290 ℃ of temperature of reaction, initial hydrogen pressure 4MPa, reaction times 8h, mixing speed 600r/min.The composition of lignin phenol and their hydrogenation products are as shown in table 6.
Table 6
Embodiment 4
Similar to embodiment 1 method, select single nickel catalyst as hydrogenation catalyst, set reaction conditions: liquid-solid ratio is 100: 3,300 ℃ of temperature of reaction, initial hydrogen pressure 2MPa, reaction times 4h, mixing speed 300r/min.Xylogen degradation results in aqueous sodium hydroxide solution is as shown in table 7.
Table 7
Similar to embodiment 1 method, select single nickel catalyst as hydrogenation catalyst, set reaction conditions: 290 ℃ of temperature of reaction, initial hydrogen pressure 4MPa, reaction times 8h, mixing speed 600r/min.
Table 8
The composition of lignin phenol and their hydrogenation products are as shown in table 8.
Claims (10)
1. xylogen two-step approach is converted into a method for liquid fuel, it is characterized in that comprising the following steps:
1) xylogen, hydrogenation catalyst and basic solution are joined in reactor and carry out depolymerization reaction, after reaction, add again HCl solution and ethyl acetate, filter, solid drying, liquid separation oil phase and water add anhydrous magnesium sulfate in oil phase, revolve steaming after filtration;
2) lignin phenol, hydrogenation catalyst and water are joined to reaction kettle for reaction, then add ethyl acetate, filter, catalyzer is dry, reclaims, and liquid revolves steaming, obtains liquid fuel.
2. a kind of method that xylogen two-step approach is converted into liquid fuel as claimed in claim 1, is characterized in that in step 1) in, described basic solution is selected from alkaline aqueous solution or alkaline alcohol/aqueous solution.
3. a kind of method that xylogen two-step approach is converted into liquid fuel as claimed in claim 2, the volumetric concentration that it is characterized in that alcohol in described alkaline alcohol/aqueous solution is 15%～85%, preferably 30%～70%.
4. a kind of method that xylogen two-step approach is converted into liquid fuel as claimed in claim 1, it is characterized in that in step 1) in, the alkali using in basic solution is selected from least one in sodium hydroxide, potassium hydroxide, lithium hydroxide, calcium hydroxide, magnesium hydroxide, salt of wormwood; The mass percentage concentration of alkali can be 1%～8%, and preferably 1%～5%.
5. a kind of method that xylogen two-step approach is converted into liquid fuel as claimed in claim 1, is characterized in that in step 1) in, the condition of described depolymerization reaction is: 250～350 ℃ of temperature, initial hydrogen pressure 1～5MPa, time 0.5～8h.
6. a kind of method that xylogen two-step approach is converted into liquid fuel as claimed in claim 1, is characterized in that in step 1) in, it is 10%HCl solution that described HCl solution adopts mass concentration; Described liquid separation oil phase can adopt the separated oil phase of separating funnel and water with water.
7. a kind of method that xylogen two-step approach is converted into liquid fuel as claimed in claim 1, is characterized in that in step 2) in, described hydrogenation catalyst adopts dual-function catalyst or single nickel series hydrogenating catalyst; Described dual-function catalyst adopts the combination of hydrogenation catalyst and acid catalyst, and hydrogenation catalyst is selected from a kind of in Pd/C, Ru/C catalyzer, and acid catalyst is selected from a kind of in hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, HZSM-5 molecular sieve; The preferably combination of noble metal catalyst and phosphoric acid.
8. a kind of method that xylogen two-step approach is converted into liquid fuel as claimed in claim 7, is characterized in that sour mass concentration is 0.5%～4.0%, preferably 1.0%～2.5%.
9. a kind of method that xylogen two-step approach is converted into liquid fuel as claimed in claim 7, is characterized in that described single nickel series hydrogenating catalyst is selected from Raney Ni, Ni/SiO
2, Ni/ZrO
2, Ni/SiO
2-ZrO
2a kind of in catalyzer; The charge capacity of Ni can be 5%～50%, and preferably 10%～30%.
10. a kind of method that xylogen two-step approach is converted into liquid fuel as claimed in claim 1, is characterized in that in step 2) in, the condition of described reaction is: 250～320 ℃ of temperature, pressure 1～5MPa, time 1～8h.
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Cited By (9)
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|---|---|---|---|---|
| CN104312604A (en) * | 2014-10-30 | 2015-01-28 | 中国林业科学研究院林产化学工业研究所 | Method for improving creosote content in biomass molding fuel tar |
| CN104387223A (en) * | 2014-10-29 | 2015-03-04 | 华东师范大学 | Method for catalytically converting lignin into aromatic hydrocarbon by using two-step process |
| CN105167174A (en) * | 2015-07-16 | 2015-12-23 | 华南理工大学 | Leaching liquor capable of effectively reducing lignin content in tobacco waste as well as preparation method and application of leaching liquor |
| CN106753549A (en) * | 2016-12-20 | 2017-05-31 | 中国科学院广州能源研究所 | A kind of method that lignin depolymerization lightweight phenolic product hydrotreating prepares HC fuel |
| CN107207973A (en) * | 2015-02-10 | 2017-09-26 | 克里斯能量有限公司 | Depolymerization method |
| CN109701600A (en) * | 2019-01-14 | 2019-05-03 | 沈阳航空航天大学 | Lignocellulosic simple substance zinc coupling and the micro/meso porous multistage original position the HZSM-5 hydrogen supply catalyst preparation of more metals and method for upgrading |
| CN112852468A (en) * | 2020-12-23 | 2021-05-28 | 北京林业大学 | Method for preparing biological oil rich in phenolic compounds by liquefying eucalyptus black liquor |
| CN112980487A (en) * | 2021-02-25 | 2021-06-18 | 中国石油大学(华东) | Method for preparing aromatic hydrocarbon by two-stage catalytic pyrolysis of biomass |
| CN115888802A (en) * | 2022-11-08 | 2023-04-04 | 喀什大学 | Bimetal supported catalyst, preparation method and application thereof, and method for catalyzing depolymerization of lignin |
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Cited By (13)
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| CN104387223A (en) * | 2014-10-29 | 2015-03-04 | 华东师范大学 | Method for catalytically converting lignin into aromatic hydrocarbon by using two-step process |
| CN104387223B (en) * | 2014-10-29 | 2016-08-24 | 华东师范大学 | It is the method for aromatic hydrocarbons by two-step method catalyzed conversion lignin |
| CN104312604A (en) * | 2014-10-30 | 2015-01-28 | 中国林业科学研究院林产化学工业研究所 | Method for improving creosote content in biomass molding fuel tar |
| CN107207973B (en) * | 2015-02-10 | 2020-03-27 | 克里斯能量有限公司 | Depolymerization process |
| CN107207973A (en) * | 2015-02-10 | 2017-09-26 | 克里斯能量有限公司 | Depolymerization method |
| US10457874B2 (en) | 2015-02-10 | 2019-10-29 | Ciris Energy, Inc | Depolymerization process |
| CN105167174A (en) * | 2015-07-16 | 2015-12-23 | 华南理工大学 | Leaching liquor capable of effectively reducing lignin content in tobacco waste as well as preparation method and application of leaching liquor |
| CN106753549A (en) * | 2016-12-20 | 2017-05-31 | 中国科学院广州能源研究所 | A kind of method that lignin depolymerization lightweight phenolic product hydrotreating prepares HC fuel |
| CN109701600A (en) * | 2019-01-14 | 2019-05-03 | 沈阳航空航天大学 | Lignocellulosic simple substance zinc coupling and the micro/meso porous multistage original position the HZSM-5 hydrogen supply catalyst preparation of more metals and method for upgrading |
| CN109701600B (en) * | 2019-01-14 | 2022-01-07 | 沈阳航空航天大学 | Preparation and quality improvement method of lignocellulose simple substance zinc coupling and multi-metal micro/mesoporous multi-stage HZSM-5 in-situ hydrogen supply catalyst |
| CN112852468A (en) * | 2020-12-23 | 2021-05-28 | 北京林业大学 | Method for preparing biological oil rich in phenolic compounds by liquefying eucalyptus black liquor |
| CN112980487A (en) * | 2021-02-25 | 2021-06-18 | 中国石油大学(华东) | Method for preparing aromatic hydrocarbon by two-stage catalytic pyrolysis of biomass |
| CN115888802A (en) * | 2022-11-08 | 2023-04-04 | 喀什大学 | Bimetal supported catalyst, preparation method and application thereof, and method for catalyzing depolymerization of lignin |
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