CN106480766A - A kind of method that wood fibre is hydrogenated with separating lignin - Google Patents
A kind of method that wood fibre is hydrogenated with separating lignin Download PDFInfo
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- CN106480766A CN106480766A CN201610802102.4A CN201610802102A CN106480766A CN 106480766 A CN106480766 A CN 106480766A CN 201610802102 A CN201610802102 A CN 201610802102A CN 106480766 A CN106480766 A CN 106480766A
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- wood fibre
- hydrogenated
- lignin
- separating lignin
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- 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
- D21C3/22—Other features of pulping processes
- D21C3/222—Use of compounds accelerating the pulping processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- 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
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- Life Sciences & Earth Sciences (AREA)
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- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
A kind of method that wood fibre is hydrogenated with separating lignin, comprises the following steps：The first step, wood fibre, hydrogenation catalyst and mixed solvent is put into autoclave, and is passed through hydrogen；Second step, autoclave temperature is improved to 180 220 DEG C, response time 30 min 5 h；3rd step, filters after cooling, rinses residue with mixed solvent and dries.Present invention achieves the classified utilization of lignocellulosic components, the lignin in wood fibre is separated first, cellulose and hemicellulose that remaining physicochemical property is sufficiently close to, be conducive to product deep processing；Simplify technical process, conventional lignin separation uses water as medium, and after being changed to organic solvent, evaporation latent heat substantially reduces；Lignin degradation is that the reactivity after small molecule significantly improves, and can be further used for the high value added products such as phenolic resin.
Description
Technical field
The invention belongs to biomass pretreatment transformation technology field, relate generally in wood fibre the degraded of lignin with point
From method.
Background technology
The positive increasingly depleted of primary energy based on oil, coal, and biomass energy is using renewable or circulation
Organic substance, including crops, trees and other plant and its residuum etc. be raw material, carry out biobased products, bio-fuel and
The industry that bioenergy produces.Wood fibre contains cellulose, hemicellulose, lignin, and conventional preprocess method is papermaking
Alkaline boiling mode in industry, using alkali compoundss such as sodium sulfite, under 150-170 DEG C of pressurized conditions, by lignin, partly
Cellulose dissolution, residual fiber element is as paper making raw material.Many preprocess methods are all based on the improvement of this method at present.
Also there is not pertinent literature report wood fibre direct hydrogenation at present, the lignin degradation in wood fibre is separated.
From the point of view of wood fibre composition structure, the chemical property of its three big component differs greatly, and wherein lignin is mainly with phenol generalization
Based on compound, cellulose, hemicellulose mainly pass through, with pentose, hexose, the macromolecular compound that glycosidic bond is connected.Separately
Outward, the bond energy of the chemical bonds such as β-O-4, the 4-O-5 that in lignin, phenolic compound connects is significantly cooler in cellulose, half fiber
Element, from this view point, hydrogenation reaction first can depolymerization lignin, without destroy carbohydrate.Therefore, if adopted
Be hydrogenated with separating treatment wood fibre three big element it becomes possible to obtain corresponding high-purity chemical product respectively, not only simplify
Reaction and detached flow process, substantially increase the economic worth of product simultaneously.
Content of the invention
The technical problem solving：Cannot matterization comprehensive utilization entirely in order to solve wood fibre present in prior art；Raw
Production. art water consumption is huge, and product separates difficult；Lignin reaction's activity low it is difficult to the problem of higher value application, the present invention carries
A kind of wood fibre has been supplied to be hydrogenated with the method for separating lignin it is achieved that the classified utilization of each component of wood fibre；And simplify
Technical process, water consumption is few；Lignin degradation is that the reactivity after small molecule significantly improves.
Technical scheme：A kind of method that wood fibre is hydrogenated with separating lignin, comprises the following steps：The first step, will be wooden
Autoclave put into by fiber, hydrogenation catalyst and mixed solvent, and is passed through the hydrogen of 1-3MPa；Described mixed solvent is polarity
Organic solvent or its mixed system with water, polar organic solvent is 50 with the volume ratio of water:(100-0)；Second step, by pressure
Kettle temperature degree improves to 180-220 DEG C, response time 30min-5h；3rd step, filters after cooling, rinses residue simultaneously with mixed solvent
Dry.
Above-mentioned wood fibre is wood flour, the straw or Caulis et Folium Oryzae biomass material through pulverization process.
Above-mentioned hydrogenation catalyst is Raney's nickel, any one in Pd/C, Rh/C, Pt/MCM-41, or Pt metal or Ni bear
The mesoporous silicon carrying.
Above-mentioned polar organic solvent is methanol, ethanol, isopropanol, butanol, acetone, any one in oxolane.
Above-mentioned isopropanol and the volume ratio preferably 70 of water:30.
Initial hydrogen pressure is 2MPa.
Preferably reaction temperature is 220 DEG C, response time 3h.
Beneficial effect：Present invention achieves the classified utilization of lignocellulosic components, by the lignin in wood fibre first
Separate, cellulose and hemicellulose that remaining physicochemical property is sufficiently close to, be conducive to product deep processing；Simplify technical process,
Conventional lignin separation uses water as medium, and after being changed to organic solvent, evaporation latent heat substantially reduces；Lignin degradation is
Reactivity after small molecule significantly improves, and can be further used for the high value added products such as phenolic resin.
Brief description
Fig. 1 is the GC-MS spectrogram of the lignin of embodiment 1 degraded；
Fig. 2 is the photo of solid content (cellulose, hemicellulose) in embodiment 1.
Specific embodiment
A kind of method that wood fibre is hydrogenated with separating lignin, comprises the following steps：
The first step, wood fibre, hydrogenation catalyst and mixed solvent is put into autoclave, and is passed through the hydrogen of 1-3MPa
Gas；Hydrogenation catalyst is Raney's nickel, any one in Pd/C, Rh/C, Pt/MCM-41, preferably Raney's nickel；Polar organic solvent
It is methanol, ethanol, isopropanol, butanol, acetone, any one in oxolane, preferably isopropanol；Polar organic solvent and water
Mixed proportion be 50-100:50-0, preferably 70:30；
Second step, autoclave temperature is improved to 180-220 DEG C, response time 30min-5h；
3rd step, filters after cooling, uses solvent washing residue, dries at 100 DEG C.
Embodiment 1：
By bamboo scraps 16g, isopropanol 100mL (about 78.5g), water 40mL, it is anti-that Raney's nickel (Raney Ni) 10g is added to high pressure
Answer in kettle, and be passed through the hydrogen of 2MPa, open stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction knot
Open reactor after bundle, collect gas 1.23g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue, 100
Dry at DEG C, solid content 7.27g be obtained, yield 45.4%, through detection fibers element, hemicellulose level totally 94%.Filter
The filtrate obtaining, through rotary evaporation, obtains black liquor 6.67g, yield 41.7%.
Embodiment 2：
By poplar bits 16g, isopropanol 100mL (about 78.5g), water 40mL, Raney's nickel (Raney Ni) 10g is added to high pressure
In reactor, and it is passed through the hydrogen of 3MPa, opens stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction
Open reactor after end, collect gas 1.88g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue,
Dry at 100 DEG C, solid content 7.03g be obtained, yield 43.9%, through detection fibers element, hemicellulose level totally 92%.Cross
Filter the filtrate obtaining through rotary evaporation, obtain black liquor 6.27g, yield 39.2%.
Embodiment 3：
By bamboo scraps 16g, isopropanol 70mL (about 70.6g), water 30mL, it is anti-that Raney's nickel (Raney Ni) 10g is added to high pressure
Answer in kettle, and be passed through the hydrogen of 2MPa, open stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction knot
Open reactor after bundle, collect gas 1.45g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue, 100
Dry at DEG C, solid content 7.46g be obtained, yield 46.6%, through detection fibers element, hemicellulose level totally 95%.Filter
The filtrate obtaining, through rotary evaporation, obtains black liquor 6.52g, yield 40.7%.
Embodiment 4：
By bamboo scraps 16g, isopropanol 140mL (about 110g), Raney's nickel (Raney Ni) 10g is added in autoclave,
And it is passed through the hydrogen of 2MPa, open stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction is opened after terminating
Open reactor, collect gas 0.33g with collection and confinement of gases bag, liquid, through filtering, with above-mentioned solvent washing residue, dries at 100 DEG C
Dry, solid content 9.33g be obtained, yield 58.3%, through detection fibers element, hemicellulose level totally 83%.It is filtrated to get
Filtrate, through rotary evaporation, obtains black liquor 4.22g, yield 26.4%.
Embodiment 5：
By bamboo scraps 16g, isopropanol 100mL (about 78.5g), water 40mL, it is anti-that Raney's nickel (Raney Ni) 10g is added to high pressure
Answer in kettle, and be passed through the hydrogen of 2MPa, open stirring, be warmed up to 180 DEG C under 5 DEG C/min heating rate, be incubated 30min.Instead
Reactor should be opened after terminating, collect gas 0.09g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue,
Dry at 100 DEG C, solid content 12.73g be obtained, yield 79.6%, through detection fibers element, hemicellulose level totally 58%.
The filtrate being filtrated to get, through rotary evaporation, obtains black liquor 2.63g, yield 16.4%.
Embodiment 6：
By bamboo scraps 16g, isopropanol 100mL (about 78.5g), water 40mL, it is anti-that Raney's nickel (Raney Ni) 10g is added to high pressure
Answer in kettle, open stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 5h.Reaction opens reactor after terminating, and uses
Gas 3.59g collected by collection and confinement of gases bag, and liquid, through filtering, with above-mentioned solvent washing residue, is dried at 100 DEG C, is obtained solid
Shape thing 6.08g, yield 38.0%, through detection fibers element, hemicellulose level totally 94%.The filtrate being filtrated to get is through rotation
Evaporation, obtains black liquor 7.92g, yield 49.5%.
Embodiment 7：
By bamboo scraps 16g, isopropanol 100mL (about 78.5g), water 40mL, Pd/C 3g is added in autoclave, and leads to
Enter the hydrogen of 2MPa, open stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction is opened anti-after terminating
Answer kettle, collect gas 1.77g with collection and confinement of gases bag, liquid, through filtering, with above-mentioned solvent washing residue, is dried at 100 DEG C, altogether
Obtain solid content 8.76g, yield 54.8%, through detection fibers element, hemicellulose level totally 87%.The filtrate warp being filtrated to get
Cross rotary evaporation, obtain black liquor 5.35g, yield 33.4%.
Embodiment 8：
By bamboo scraps 16g, isopropanol 100mL (about 78.5g), water 40mL, Rh/C 3g is added in autoclave, and leads to
Enter the hydrogen of 2MPa, open stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction is opened anti-after terminating
Answer kettle, collect gas 1.85g with collection and confinement of gases bag, liquid, through filtering, is obtained solid content 8.23g, yield 51.4%, passes through
Detection fibers element, hemicellulose level totally 85%.The filtrate being filtrated to get, through rotary evaporation, obtains black liquor 4.88g, receives
Rate 30.5%.
Embodiment 9：
By Caulis et Folium Oryzae 16g, isopropanol 100mL (about 78.5g), water 40mL, it is anti-that Raney's nickel (Raney Ni) 10g is added to high pressure
Answer in kettle, and be passed through the hydrogen of 2MPa, open stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction knot
Open reactor after bundle, collect gas 3.93g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue, 100
Dry at DEG C, solid content 6.11g be obtained, yield 38.2%, through detection fibers element, hemicellulose level totally 73%.Filter
The filtrate obtaining, through rotary evaporation, obtains black liquor 3.54g, yield 22.1%.
Embodiment 10：
By bamboo scraps 16g, methanol 100mL (about 79.0g), water 40mL, Raney's nickel (Raney Ni) 10g is added to reaction under high pressure
In kettle, and it is passed through the hydrogen of 2MPa, opens stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction terminates
Open reactor afterwards, collect gas 3.12g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue, 100 DEG C
Lower drying, is obtained solid content 6.34g, yield 39.6%, through detection fibers element, hemicellulose level totally 91%.Filter
The filtrate arrived, through rotary evaporation, obtains black liquor 6.07g, yield 37.9%.
Embodiment 11：
By bamboo scraps 16g, ethanol 100mL (about 79.0g), water 40mL, Raney's nickel (Raney Ni) 10g is added to reaction under high pressure
In kettle, and it is passed through the hydrogen of 2MPa, opens stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction terminates
Open reactor afterwards, collect gas 1.23g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue, 100 DEG C
Lower drying, is obtained solid content 7.27g, yield 45.44%, through detection fibers element, hemicellulose level totally 94%.Filter
The filtrate arrived, through rotary evaporation, obtains black liquor 6.67g, yield 41.7%.
Embodiment 12：
By bamboo scraps 16g, butanol 100mL (about 82.0g), water 40mL, Raney's nickel (Raney Ni) 10g is added to reaction under high pressure
In kettle, and it is passed through the hydrogen of 2MPa, opens stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction terminates
Open reactor afterwards, collect gas 0.71g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue, 100 DEG C
Lower drying, is obtained solid content 10.17g, yield 63.6%, through detection fibers element, hemicellulose level totally 71%.Filter
The filtrate arrived, through rotary evaporation, obtains black liquor 3.94g, yield 24.6%.
Embodiment 13：
By bamboo scraps 16g, acetone 100mL (about 78.8g), water 40mL, Raney's nickel (Raney Ni) 10g is added to reaction under high pressure
In kettle, and it is passed through the hydrogen of 2MPa, opens stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction terminates
Open reactor afterwards, collect gas 2.51g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue, 100 DEG C
Lower drying, is obtained solid content 6.78g, yield 42.3%, through detection fibers element, hemicellulose level totally 85%.Filter
The filtrate arrived, through rotary evaporation, obtains black liquor 7.37g, yield 46.1%.
Embodiment 14：
By bamboo scraps 16g, oxolane 100mL (about 89.0g), water 40mL, Raney's nickel (Raney Ni) 10g is added to high pressure
In reactor, and it is passed through the hydrogen of 2MPa, opens stirring, be warmed up to 220 DEG C under 5 DEG C/min heating rate, be incubated 3h.Reaction
Open reactor after end, collect gas 3.13g with collection and confinement of gases bag, liquid through filtering, with above-mentioned solvent washing residue,
Dry at 100 DEG C, solid content 5.27g be obtained, yield 32.9%, through detection fibers element, hemicellulose level totally 79%.Cross
Filter the filtrate obtaining through rotary evaporation, obtain black liquor 8.25g, yield 51.6%.
Embodiment 15：
By poplar bits 16g, isopropanol 100mL (about 78.5g), water 40mL, mesoporous type hydrogenating reduction catalyst 5g is added to
In autoclave, and it is passed through the hydrogen of 2MPa, opens stirring, be warmed up to 200 DEG C under 5 DEG C/min heating rate, be incubated 3h.
Reaction opens reactor after terminating, and collects gas 1.68g with collection and confinement of gases bag, and liquid is through filtering, residual with above-mentioned solvent washing
Slag, dries at 100 DEG C, solid content 7.15g is obtained, yield 44.7%, common through detection fibers element, hemicellulose level
93%.The filtrate being filtrated to get, through rotary evaporation, obtains black liquor 6.23g, yield 38.9%.
Embodiment 16：
Liquid phase reduction prepares the mesoporous type hydrogenating reduction catalyst of metal active centres high degree of dispersion.
(1) by the water soluble salt of Pt, Pd, Ru noble metal and EDTA mixed dissolution, mol ratio m (precious metal salt):m(EDTA)
=1:(0.1-5)；
(2) by go back original reagent (as NaBH4) it is dissolved in water；
(3) add (1) resulting solution under agitation, and the carrier such as mesoporous silicon；
(4) (2) resulting solution is dropped in (3)；
(5) 3h, sucking filtration afterwards are reacted at 50 DEG C, ethyl acetate is washed, 105 DEG C of dryings obtain finished catalyst.
Embodiment 17：
The GC-MS spectrogram of the lignin of degraded in embodiment 3, and the cellulose after lignin separation.
Claims (7)
1. a kind of wood fibre is hydrogenated with the method for separating lignin it is characterised in that comprising the following steps：
The first step, wood fibre, hydrogenation catalyst and mixed solvent is put into autoclave, and is passed through the hydrogen of 1-3MPa；
Described mixed solvent is polar organic solvent or its mixed system with water, and polar organic solvent is 50 with the volume ratio of water:
(100-0)；
Second step, autoclave temperature is improved to 180-220 DEG C, response time 30 min-5 h；
3rd step, filters after cooling, rinses residue with mixed solvent and dries.
2. wood fibre as claimed in claim 1 is hydrogenated with the method for separating lignin it is characterised in that described wood fibre
For wood flour, straw or Caulis et Folium Oryzae through pulverization process biomass material.
3. wood fibre as claimed in claim 1 is hydrogenated with the method for separating lignin it is characterised in that hydrogenation catalyst is thunder Buddhist nun
Any one in nickel, Pd/C, Rh/C, Pt/MCM-41, or the mesoporous silicon of Pt metal or Ni load.
4. wood fibre as claimed in claim 1 is hydrogenated with the method for separating lignin it is characterised in that polar organic solvent is first
Any one in alcohol, ethanol, isopropanol, butanol, acetone, oxolane.
5. wood fibre as claimed in claim 4 is hydrogenated with the method for separating lignin it is characterised in that the volume of isopropanol and water
Ratio preferably 70:30.
6. wood fibre as claimed in claim 1 is hydrogenated with the method for separating lignin it is characterised in that initial hydrogen pressure is 2
MPa.
7. wood fibre as claimed in claim 1 is hydrogenated with the method for separating lignin it is characterised in that reaction temperature is 220 DEG C,
Response time 3h.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109322199A (en) * | 2018-09-28 | 2019-02-12 | 中国林业科学研究院林产化学工业研究所 | A kind of method of wood fibre full constituent comprehensive utilization |
| CN110590860A (en) * | 2019-09-29 | 2019-12-20 | 中国林业科学研究院林产化学工业研究所 | Method for preparing lignin oligomer by selective reductive degradation |
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| CN103508858A (en) * | 2012-06-29 | 2014-01-15 | 中国科学院大连化学物理研究所 | Method for preparing aromatic compounds employing catalytic cracking of industrial lignins |
| CN104276930A (en) * | 2013-07-08 | 2015-01-14 | 中国科学院大连化学物理研究所 | Method for preparation of phenolic compound by direct hydrogenolysis of lignin |
| CA2931672A1 (en) * | 2013-11-27 | 2015-06-04 | Kat2Biz Ab | Depolymerisation of lignin in biomass |
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| CN102476980A (en) * | 2010-11-30 | 2012-05-30 | 中国科学院大连化学物理研究所 | Application of tungsten-based catalyst in lignin catalytic hydrogenation for producing aromatic compound |
| CN103508858A (en) * | 2012-06-29 | 2014-01-15 | 中国科学院大连化学物理研究所 | Method for preparing aromatic compounds employing catalytic cracking of industrial lignins |
| CN104276930A (en) * | 2013-07-08 | 2015-01-14 | 中国科学院大连化学物理研究所 | Method for preparation of phenolic compound by direct hydrogenolysis of lignin |
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| CN109322199A (en) * | 2018-09-28 | 2019-02-12 | 中国林业科学研究院林产化学工业研究所 | A kind of method of wood fibre full constituent comprehensive utilization |
| CN110590860A (en) * | 2019-09-29 | 2019-12-20 | 中国林业科学研究院林产化学工业研究所 | Method for preparing lignin oligomer by selective reductive degradation |
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