CN106117023B - The method that lignin methylation in-series reduction two-step method lignin degrading prepares single benzene ring compound - Google Patents
The method that lignin methylation in-series reduction two-step method lignin degrading prepares single benzene ring compound Download PDFInfo
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Abstract
The invention discloses the methods that lignin methylation in-series reduction two-step method lignin degrading prepares single benzene ring compound.Lignin, methanol and catalyst are added in microwave reaction tank by this method, and setting microwave reaction power is 50-1000W, and microwave frequency is 2450MHz ± 15Hz, 10-120min are reacted at 100-250 DEG C, benzylalcohol methylation lignin is made；Then cooling reaction solution is transferred in autoclave, and 5%Pd/C and formic acid is added, reacts 0.5-6.0h at 200-350 DEG C；After having reacted, cooling is filtered to remove insoluble matter, obtains the solution containing single benzene ring compound.The present invention using microwave selective methylates the benzylalcohol in lignin, benzylalcohol of then degrading again methylation lignin, and method can promote lignin degradation and obtain higher yield and the lower single benzene ring compound of oxygen content.
Description
Technical field
The present invention relates to the methods that lignin degrading prepares single benzene ring compound, methylate more particularly to a kind of lignin
The method that in-series reduction two-step method lignin degrading prepares single benzene ring compound.
Background technique
The fast development of global industry leads to demand of the human society to the energy and small molecule fragrance industrial chemicals rapidly
Increase with exploitation, processing and causes the lance seriously destroyed to ecological environment in the process using non-renewable traditional fossil energy
Shield is constantly prominent, so the mankind need to find a kind of sustainable resource of alternative fossil resource, to produce small molecule fragrance
Chemical products and the energy.Lignin is the second largest natural polymer, is that content is maximum containing benzene ring structure in nature
Renewable low-cost resource.Small molecule aromatic radical fine chemicals is prepared by raw material of lignin, hydrogenation deoxidation can also be passed through
Equal chemical means integrate the micromolecular aromachemicals and prepare advanced bio fuel.
Since lignin has complicated random three-dimensional netted non-crystal structure, be usually used at present depolymerization lignin prepare it is small
The small molecule that the technologies such as cracking, hydrogenolysis, oxidation, hydrolysis, ionic liquid and the Asia of molecule aromatic compound/overcritical are prepared
The yield of aromatic compound is to be improved and severe reaction conditions.Meanwhile degrade at present obtained single phenyl ring product oxygen content compared with
Height (Applied biochemistry and biotechnology, 2001,91 (1-9): 71-80；Energy&Fuels,
2015,29 (9): 5835-5840.), it is very big that prepared by high-rank fuel challenge to follow-up hydrogenation deoxidation.
Nguyen(Journal of the American Chemical Society,2014,136(4):1218-
1221.), Rahimi (Nature, 2014,515 (7526): 249-252.) and Lancefield (Angewandte Chemie,
2015,127 (1): 260-264.) etc. scholars propose two-step method degradation technique: first benzylalcohol is selectively oxidized to benzyl ketone, in turn
Lignin degrading again.The available higher conversion ratio of catalytic hydrogenolysis lignin and single benzene ring compound yield, therefore hydrogenolysis quilt
It is considered the technology of most potential lignin degrading, while the technology is also by domestic and international related focus of attention
(ChemSusChem,2014,7(8):2154-2158；Bioresource technology,2015,179:84-90；
Bioresource technology,2016,200:14-22.).However, the presence of Zhou et al. report benzyl ketone makes lignin
In main β-O-4 ehter bond cleavage activity reduce (ChemSusChem, 2014,7 (6): 1623-1626.).It is wooden to promote
The alcoholic extract hydroxyl group acetylation of C α and C γ are first improved the activity of hydrogenolysis β-O-4 ehter bond by element degradation industrial expansion, Marks et al.,
However the acetyl bromide that acetylation uses is malicious big and volatile (ACS Catalysis, 2015,5 (11): 7004-7007.).
Therefore, develop a kind of lignin degradation new technology to pushing the lignin degradation preparation small molecule aromatic compound there is important meaning
Justice.
Summary of the invention
The purpose of the present invention is for the existing technology presence for preparing single benzene ring type compounds using lignin as raw material
The problems such as single benzene ring type compounds yield is low and product high oxygen content, benzylalcohol in a kind of lignin is provided and is methylated and is dropped again
The benzylalcohol of lignin is methylated to the inventive technique property of can choose, is degraded simultaneously by the method that solution prepares single benzene ring compound
The available higher yield of benzylalcohol methylation lignin and hypoxic single phenyl ring product.
The purpose of the present invention is implemented by following technical solution:
The method that lignin methylation in-series reduction two-step method lignin degrading prepares single benzene ring compound, including following step
It is rapid:
1) catalyst of the lignin of 1 parts by weight, the methanol of 10-1000 parts by weight and 0.01-5 parts by weight is added to micro-
In wave reactor tank, setting microwave power is 50-1000W, and microwave frequency is 2450MHz ± 15Hz, is reacted at 100-250 DEG C
Benzylalcohol methylation lignin is made in 10-120min；The catalyst is HNO3、Mg(NO3)2、Al(NO3)3、Mn(NO3)2、Fe
(NO3)3、Co(NO3)2、Ni(NO3)2、Cu(NO3)2、Zn(NO3)2、H3PO4、Mg3(PO4)2、AlPO4、Mn3(PO4)2、FePO4、Co3
(PO4)2、Ni3(PO4)2、Cu3(PO4)2、Zn3(PO4)2、H2SO4、MgSO4、Al2(SO4)3、MnSO4、Fe2(SO4)3、CoSO4、
NiSO4、CuSO4、ZnSO4、HCl、MgCl2、AlCl3、MnCl2、FeCl3、CoCl2、NiCl2、CuCl2And ZnCl2One of or
It is a variety of；
2) the cooling reaction solution of step 1) is transferred in autoclave, and 0.01-0.3 parts by weight 5%Pd/C is added
With 0.3-8 parts by weight formic acid, 0.5-6.0h is reacted at 200-350 DEG C；
3) reaction solution of step 2) is cooling, be filtered to remove insoluble matter, obtain the solution containing single benzene ring compound.
To further realize the object of the invention, it is preferable that the lignin is that enzymolysis xylogen or alkali paper-making slurrying are black
Solid Wheat Straw Lignin from Alkali Pulping, the bagasse alkali-lignin, wood pulp alkali lignin of liquid recycling.
Preferably, the lignin is that biomass removes the lignin obtained after cellulose, hemicellulose.
Preferably, the mass ratio of lignin and methanol is 1:100-1:1000 in step 1).
Preferably, microwave power is 100-800W in step 1).
Preferably, reaction temperature is 100-200 DEG C in step 1), reaction time 10-100min.
Preferably, the mass ratio of lignin and 5%Pd/C are 0.01-0.2 in step 2).
Preferably, the mass ratio of lignin and formic acid is 0.5-5 in step 2).
Preferably, microwave frequency is 2450MHz in step 1).
Preferably, the time reacted at 200-350 DEG C is 1-4h.
The present invention has following outstanding advantages and effect:
1, using microwave selective benzylalcohol methylation lignin, method will be made after the methylation of lignin benzylalcohol in the present invention
Simply, high-efficient；
2, the present invention prepares benzylalcohol methylation lignin by using Microwave-assisted firing, and combines autoclave to benzyl
Alcohol methylation lignin is degraded.After the benzylalcohol methylation of lignin, C on β-O-4 ehter bond and C3 side chain can be reduced
The bond energy of α-C β key, therefore the present invention is conducive to the degradation of lignin, to substantially increase Lignin degradation rate and single phenyl ring
Compound yield.
3, when direct hydrogenolysis lignin, usual oxygen atom on the position side chain C α, and after the methylation of the benzylalcohol of lignin, side chain
Methoxyl group on the position C α is easy to fall off, this makes in single phenyl ring product on the position side chain C α containing less oxygen atom, therefore the present invention
Single benzene ring compound oxygen content can also be reduced.
4, the present invention provides a new degradation pathway for the efficient application of lignin, will push lignin degrading preparation
The development of single benzene ring compound the relevant technologies, the important meaning with sustainable development.
Detailed description of the invention
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of 1 gained benzylalcohol of embodiment methylation lignin.
Fig. 2 is main single benzene ring compound that lignin degradation described in embodiment 1 and comparative example 1 obtains.
Specific embodiment
For a better understanding of the invention, the present invention is further illustrated with reference to the accompanying drawings and examples, but this hair
Bright embodiment is unlimited so.
Embodiment 1
Take Wheat Straw Lignin from Alkali Pulping 1g and 0.1g Al (NO3)3It is added in 100g methanol, the power that microwave reactor is arranged is
100W, microwave frequency 2450MHz react 100min at 100 DEG C of Microwave-assisted firing.
After cooling, reaction solution is washed on sand core funnel device, is filtered, finally the vacuum drying oven at 50 DEG C is dry
Obtain benzylalcohol methylation lignin.The benzylalcohol methylation each 50mg of lignin obtained after the lignin before answering and reaction is negated to be dissolved in
In 0.5mL deuterated dimethyl sulfoxide (DMSO), hydrogen nuclear magnetic resonance spectrum analysis is carried out, the nuclear-magnetism before and after lignin methylation reaction is total
Fig. 1 is shown in vibration hydrogen spectrogram comparison.Fig. 1 is shown, is compared with the lignin hydrogen nuclear magnetic resonance spectrogram before reacting, benzylalcohol methylation lignin
Occurs new C α-methoxyl group signal peak at chemical shift 3.16ppm, this illustrates that the method for the present invention effectively will be wooden
The benzylalcohol methylation of element.
Cooling reaction solution is transferred in autoclave, and 0.05g 5%Pd/C is added and (loads 5wt%Pd in C
On, this field abbreviation 5%Pd/C) and 3g formic acid react 4h at 230 DEG C after air in nitrogen displacement kettle；After having reacted,
Cooling is filtered to remove insoluble matter, obtains the solution containing single benzene ring compound.
The solution containing single benzene ring compound is filtered, filtrate is directly taken to carry out gas chromatography-mass spectrometry analysis.Instrument uses PE-
5MS capillary column (30m × 0.25mm × 0.25 μm), carrier gas are helium, flow velocity 1.0mL/min；It 50 DEG C of initial column temperature, keeps
After 3min, 150 DEG C are raised to the rate of 10 DEG C/min, keeps 10min；250 DEG C are raised to the rate of 10 DEG C/min, is kept
10min；200 DEG C of injector temperature, 5 μ L of sample volume, split ratio 5；Ε Ι ion source, 200 DEG C of ion source temperature.Detect obtained master
Single benzene ring compound is wanted to see Fig. 2.Fig. 2 shows that single phenyl ring product after hydrogenolysis almost remains side chain, obtains on the position side chain C α not
Single phenyl ring product I containing oxygen atom, while can also obtain the single benzene for containing two oxygen atoms on the position side chain C α containing oxygen atom or side chain
Ring product II, and product II is compared with product I high oxygen content.
Defining and test result and 1 base of embodiment in relation to list phenyl ring product I and list phenyl ring product II in following example
This is identical, does not provide Detailed description of the invention one by one.Comparative example in relation to list phenyl ring product I and single phenyl ring product II define also with embodiment
1 is identical.
Embodiment 2
Take bagasse alkali lignin 1g and 0.2g Mn3(PO4)2It is added in 700g methanol, the function of microwave reactor is set
Rate is 500W, microwave frequency 2450MHz, reacts 35min at 200 DEG C of Microwave-assisted firing；Cooling reaction solution is transferred to
In autoclave, and 0.18g 5%Pd/C and 1g formic acid is added, after air in nitrogen displacement kettle, is reacted at 330 DEG C
1h；After having reacted, cooling is filtered to remove insoluble matter, obtains the solution containing single benzene ring compound.
Embodiment 3
Take enzymolysis xylogen 1g and 1g ZnSO4It being added in 300g methanol, the power that microwave reactor is arranged is 700W,
Microwave frequency is 2450MHz, reacts 20min at 190 DEG C of Microwave-assisted firing；Cooling reaction solution is transferred to autoclave
In, and 0.12g 5%Pd/C and 0.6g formic acid is added, after air in nitrogen displacement kettle, 2h is reacted at 300 DEG C；It has reacted
Afterwards, it cools down, be filtered to remove insoluble matter, obtain the solution containing single benzene ring compound.
Embodiment 4
Take bagasse alkali lignin 1g and 3g CuCl2It is added in 800g methanol, the power that microwave reactor is arranged is
150W, microwave frequency 2450MHz react 60min at 150 DEG C of Microwave-assisted firing；Cooling reaction solution is transferred to high pressure
In reaction kettle, and 0.02g 5%Pd/C and 1.5g formic acid is added, after air in nitrogen displacement kettle, reacts 3h at 250 DEG C；
After having reacted, cooling is filtered to remove insoluble matter, obtains the solution containing single benzene ring compound.
Embodiment 5
Take Wheat Straw Lignin from Alkali Pulping 1g and 0.4g MgSO4It is added in 200g methanol, the power that microwave reactor is arranged is
350W, microwave frequency 2450MHz react 30min at 180 DEG C of Microwave-assisted firing；Cooling reaction solution is transferred to high pressure
In reaction kettle, and 0.1g 5%Pd/C and 5g formic acid is added, after air in nitrogen displacement kettle, reacts 2.5h at 280 DEG C；Instead
After having answered, cooling is filtered to remove insoluble matter, obtains the solution containing single benzene ring compound.
Embodiment 6
Take wood pulp alkali lignin 1g and 0.5g MgCl2It is added in 400g methanol, the power that microwave reactor is arranged is
600W, microwave frequency 2450MHz react 80min at 130 DEG C of Microwave-assisted firing；Cooling reaction solution is transferred to high pressure
In reaction kettle, and 0.08g 5%Pd/C and 2.5g formic acid is added, after air in nitrogen displacement kettle, reacts 2h at 260 DEG C；
After having reacted, cooling is filtered to remove insoluble matter, obtains the solution containing single benzene ring compound.
Comparative example 1 (comparative example 1)
Take Wheat Straw Lignin from Alkali Pulping 1g, 0.05g 5%Pd/C and 3g formic acid into autoclave, with sky in nitrogen displacement kettle
After gas, 4h is reacted at 230 DEG C；After having reacted, cooling is filtered to remove insoluble matter, obtains the solution containing single benzene ring compound.Wood
Main single benzene ring compound that quality is degraded is shown in attached drawing 2.
Comparative example 2 (comparative example 3)
Take enzymolysis xylogen 1g, 0.12g 5%Pd/C and 0.6g formic acid into autoclave, with sky in nitrogen displacement kettle
After gas, 2h is reacted at 300 DEG C；After having reacted, cooling is filtered to remove insoluble matter, obtains the solution containing single benzene ring compound.
Comparative example 3 (comparative example 6)
Take wood pulp alkali lignin 1g, 0.08g 5%Pd/C and 2.5g formic acid into autoclave, in nitrogen displacement kettle
After air, 2h is reacted at 260 DEG C；After having reacted, cooling is filtered to remove insoluble matter, obtains the solution containing single benzene ring compound.
Implementation result explanation
The yield of the degradation rate of alkali lignin and single benzene ring compound is pressed following formula respectively and is calculated:
The degradation rate (wt%) of alkali lignin=(lignin residue after quality-reaction that alkali lignin is added before reacting
Quality)/react quality × 100% that preceding alkali lignin is added
The quality that alkali lignin is added before yield % (wt%)=mono- phenyl ring product quality/reaction of single benzene ring compound
× 100%
The quality of product I: product II=mono- phenyl ring product I: the quality of single phenyl ring product II=mono- phenyl ring product I matter
Amount/mono- phenyl ring product II quality: 1.0
Table 1 is the number that the embodiment of the present invention and comparative example obtain alkali lignin degradation rate with the yield of single benzene ring type compounds
According to.
Implementation result to illustrate the invention, by (new process) of the embodiment of the present invention and comparative example (old technology) catalytic degradation
The degradation rate of alkali lignin and the yield of single benzene ring type compounds compare after alkali lignin, and contrast effect is shown in Table 1.
The degradation effect of 1 lignin of table summarizes
As it can be seen from table 1 alkali lignin of degrading in the case where lignin of the invention methylates in-series reduction two-step method (is implemented
Example 1-6), the degradation rate of alkali lignin reaches 90wt% or more, and the yield of single benzene ring type compounds reach 17wt% with
On.However, the degradation rate of alkali lignin and single benzene ring compound are received when alkali lignin is reduced directly and degrades (comparative example 1-3)
Rate is significantly lower than new process of the present invention.Meanwhile compared with product II, the C3 side chain of product I is containing less oxygen, and product of the present invention
I: product II is all larger than 7.0, hence it is evident that higher than the 1.3-1.5:1.0 of comparative example, i.e., it is less that the present invention can obtain oxygen content
Single benzene ring compound.To sum up, the present invention can promote lignin degradation and obtain higher yield and the lower single benzene of oxygen content
Cycle compound, this development that lignin degrading will be pushed to prepare single benzene ring compound the relevant technologies.
Claims (4)
- The method that in-series reduction two-step method lignin degrading prepares single benzene ring compound 1. lignin methylates, it is characterised in that packet Include following steps:1) catalyst of the lignin of 1 parts by weight, the methanol of 100-1000 parts by weight and 0.01-5 parts by weight is added to microwave In reactor tank, setting microwave power is 100-800W, and microwave frequency is 2450MHz ± 15Hz, reacts 10- at 100-200 DEG C Benzylalcohol methylation lignin is made in 100min；The catalyst is HNO3、Mg(NO3)2、Al(NO3)3、Mn(NO3)2、Fe (NO3)3、Co(NO3)2、Ni(NO3)2、Cu(NO3)2、Zn(NO3)2、H3PO4、Mg3(PO4)2、AlPO4、Mn3(PO4)2、FePO4、Co3 (PO4)2、Ni3(PO4)2、Cu3(PO4)2、Zn3(PO4)2、H2SO4、MgSO4、Al2(SO4)3、MnSO4、Fe2(SO4)3、CoSO4、 NiSO4、CuSO4、ZnSO4、HCl、MgCl2、AlCl3、MnCl2、FeCl3、CoCl2、NiCl2、CuCl2And ZnCl2One of or It is a variety of；2) the cooling reaction solution of step 1) is transferred in autoclave, and be added 0.01-0.2 parts by weight 5%Pd/C and 0.5-5 parts by weight formic acid, reacts 1-4h at 200-350 DEG C；3) reaction solution of step 2) is cooling, be filtered to remove insoluble matter, obtain the solution containing single benzene ring compound.
- 2. lignin methylation in-series reduction two-step method lignin degrading according to claim 1 prepares single benzene ring compound Method, it is characterised in that: the lignin is the solid wheat straw alkali wood that enzymolysis xylogen or alkali paper-making black liquor of pulp making recycle Quality, bagasse alkali-lignin, wood pulp alkali lignin.
- 3. lignin methylation in-series reduction two-step method lignin degrading according to claim 1 prepares single benzene ring compound Method, it is characterised in that: the lignin is the lignin that biomass removes cellulose, obtains after hemicellulose.
- 4. lignin methylation in-series reduction two-step method lignin degrading according to claim 1 prepares single benzene ring compound Method, it is characterised in that: in step 1) microwave frequency be 2450MHz.
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| CN104558204A (en) * | 2015-01-20 | 2015-04-29 | 西安理工大学 | Green quick high-efficiency methylation method of cellulose |
| CN104558202A (en) * | 2015-01-20 | 2015-04-29 | 西安理工大学 | Green preparation method of methyl cellulose |
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| CN104558204A (en) * | 2015-01-20 | 2015-04-29 | 西安理工大学 | Green quick high-efficiency methylation method of cellulose |
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