CN106987862B - A kind of method of the electrochemical degradation lignin in eutectic solvent - Google Patents
A kind of method of the electrochemical degradation lignin in eutectic solvent Download PDFInfo
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Abstract
The invention discloses a kind of method of the electrochemical degradation lignin in eutectic solvent, it is introduced into sulfonic lignin and is dissolved in eutectic solvent, the Electro-catalytic Oxidation Process lignin in the electrolytic cell that three electrodes are formed, lignin and eutectic solvent after recovery reaction in electrolyte are recycled.The invention provides a kind of mild condition, current utilization rate is high, conversion ratio and selectivity are high, can cycle utilize, the method for environment amenable lignin degrading, allow lignin degradation to obtain more useful fine chemical products, there is good development prospect and industrial application value.
Description
Technical field
The invention belongs to Liginon Resource increment conversion to utilize technical field, and it is wooden to be related to a kind of electrochemical oxidation degraded
Element, for producing the technical method of the fine chemicals such as vanillic aldehyde and guaiacol.
Background technology
Lignin is a kind of abundant renewable resource, can be used for preparing armaticity structures alone.Traditional industrial mistake
Journey obtains energy by the lignin that burns.The latest developments of bioengineering, on the one hand realize and be converted into cellulose biomass
Liquid fuel, on the other hand generate substantial amounts of lignin.Therefore, there is an urgent need to be with fuel by lignin increment conversion, add
Add the high value compound of agent and fine chemical product for representative.A variety of value products can be generated by raw material of lignin,
Therefore, the degradation process of lignin receives much concern.The core of lignin degradation is to be converted into lignin natural polymer to enter
The monomer or oligomer small molecule that one step utilizes.
The method of lignin degradation mainly has pyrolysis, enzymatic, homogeneous or heterogeneous catalysis.Pyrolysis lignin can be given birth to
Material oil, then as fuel.Enzymatic can crack lignin model compound, remove the lignin in timber.Homogeneously
Or heterogeneous catalysis also can successfully lignin degrading.But homogeneous or heterogeneous catalysis process often uses ruthenium, iron, copper and vanadium etc.
Metallic catalyst, catalytic reaction will be carried out under the harsh conditions such as HTHP.The recovery of metallic catalyst and catalyst inactivation
Limit the application of catalytic process.
Electrochemical degradation lignin is fairly obvious as a kind of potential sustainable transform mode, its advantage.On the one hand, instead
Only electronics transfer in answering, and catalyst rests on electrode surface all the time；On the other hand, degradation reaction is entered at normal temperatures and pressures
OK, mild condition.Patent of invention " a kind of method of electrochemical means lignin degrading "（CN 102277591 B）Made using water
For electroanalysis solvent, by preferred electrode materials, optimize electrode lay-out, the oxygen that anode generates is converted in close cathodic reduction
For hydrogen peroxide, so as to realize the appropriate oxidative degradation of lignin." a kind of electrochemical degradation lignin prepares 2,6- to patent of invention
The method of di-tert-butyl-4-methy phenol "（CN201310043286.7）Sodium hydroxide solution is used as electroanalysis solvent, with Pb/
PbO2 electrodes are electrolysed oxygen as auxiliary electrode, standard saturated calomel electrode as working electrode, Cu plate electrodes as reference electrode
Change lignin degrading, then 2,6- di-tert-butyl-4-methy phenols are made in acidified, separation and purifying.Patent of invention " ferrous sulfate
The method that electrochemical degradation lignin prepares dibutyl phthalate in solution "（CN 201310335441.2）Using sulfuric acid
Ferrous iron solution is electroanalysis solvent, the electrolytic oxidation lignin degrading in the electrolytic cell that three electrodes are formed, finally obtains O-phthalic
Dibutyl phthalate.In above-mentioned aqueous phase system, to be degraded along with the electrochemical oxidation of lignin, oxygen evolution reaction is synchronously carried out, i.e., and one
Portion of electrical current is used for the cleavage reaction of carbon-carbon bond and carbon-oxygen bond in lignin, and one part of current separates out for oxygen, current utilization rate
It is relatively low.
The content of the invention
In order to solve problems of the prior art, lignin degradation is allowed to obtain more useful fine chemical products,
The invention discloses a kind of method of the electrochemical degradation lignin in eutectic solvent, it is desirable to provide a kind of mild condition, electricity
Stream utilization rate is high, conversion ratio and selectivity are high, can cycle utilization, the method for environment amenable lignin degrading.
The technical proposal of the invention is realized in this way：
The invention discloses a kind of method of the electrochemical degradation lignin in eutectic solvent, comprise the following steps：
（1）Sulfonation pretreatment will be passed through first it be introduced into sulfonic lignin and be dissolved in eutectic solvent and form homogeneous body
System；
（2）The lignin homogeneous system prepared is added in the electrolytic cell of three electrodes composition, be selected from working electrode
One kind in nickel, platinum, gold, copper electrode, auxiliary electrode are platinum electrode or carbon electrode, and reference electrode is selected from silver/silver chloride electrode, satisfied
With one kind in calomel electrode or hydrogen electrode, electrolytic cell is formed, electricity is urged under the conditions of oxidizing potential is 0.5-1V, reacts 1-24h
Change oxidative degradation lignin to produce vanillic aldehyde and guaiacol；
Wherein, the eutectic solvent salt and hydrogen bond donor by being made up of, and wherein salt is selected from choline hydrochloride, methyl three
Phenyl bromide phosphine, N, the one or more in N- diethylaluminum ethoxide ammonium chlorides, hydrogen bond donor is by urea, ethylene glycol, glycerine
In one or more material mixings form.
Preferably, step（1）In, the solubility of lignin is 0.1-100g/L in the homogeneous system.
As a kind of preferred embodiment, the method for described electrochemical degradation lignin also includes：Electricity after recovery reaction
Lignin and eutectic solvent in solution liquid are recycled.Specifically recovery method can be：After sour diluting reaction
Electrolyte, it is collected by filtration and separates out insoluble lignin；By the solvable lignin in organic extractant phase supernatant liquor, then methyl is different
The stirring mixed with water of butyl ketone, centrifuge organic phase and aqueous phase；The methyl iso-butyl ketone (MIBK) in organic phase is distilled off, obtains
Arene compound caused by lignin oxidation's degraded, is distilled off the moisture in aqueous phase, obtains eutectic solvent, circulates and be used for
Lignin electrochemical oxidation is degraded.Preferably, the acid of dilute electrolyte is one kind in dilute sulfuric acid, watery hydrochloric acid, dust technology, acid group
Ion concentration is 0.001-0.1 mol/L, and the volume ratio of acid and electrolyte is（1-20）：1；The organic phase is ethyl acetate.
Compared with prior art, beneficial effects of the present invention are：
（1）The present invention utilizes three electrolysis devices, and electrochemical oxidation lignin degrading, keeps away in eutectic solvent system
Exempt from oxygen evolution reaction, improve current utilization rate, it is environmentally friendly；
（2）The sulfonation pretreating process of lignin introduces sulfonic lignin and adds wood using common process
The hydrophily of quality, make the degradation conditions of lignin gentle, selectivity is high, and degraded obtains the essence such as vanillic aldehyde and guaiacol
The high conversion rate of thin chemicals, making guaiacol yield, vanillic aldehyde yield is 34-37%, by lignin conversion rate up to 30-38%
Improve to 80-95%；
（3）Eutectic solvent system cost is cheap, can be recycled by simple distillation.
Embodiment
The technical scheme in the embodiment of the present invention will be clearly and completely described below, it is clear that described implementation
Example only part of the embodiment of the present invention, rather than whole embodiments.It is common based on the embodiment in the present invention, this area
The every other embodiment that technical staff is obtained under the premise of creative work is not made, belong to the model that the present invention protects
Enclose.
Embodiment 1
A kind of method of the electrochemical degradation lignin in eutectic solvent, through the following steps that realize：
（1）Choline hydrochloride and urea press 1:2 ratio Hybrid Heating, the colourless eutectic solvent of homogeneous transparent is obtained, will
It is introduced into sulfonic lignin and is dissolved in eutectic solvent and form homogeneous system, the concentration of lignin is 10g/L；
（2）The lignin homogeneous system prepared is added in the electrolytic cell of three electrodes composition, using nickel electrode as work
Electrode, platinum electrode are auxiliary electrode, and reference electrode is silver/silver chloride electrode, sets oxidizing potential as 0.5V, and the reaction time is
5h, Electro-catalytic Oxidation Process lignin, guaiacol yield are 38%, and vanillic aldehyde yield is 36%, lignin conversion rate 87%；
（3）By VAcid：VElectrolyteFor 1:Electrolyte of 5 ratio after 0.01mol/L dilute sulfuric acid diluting reaction, is collected by filtration
Insoluble lignin is separated out further to degrade as raw material；Ethyl acetate makees the solvable lignin in organic extractant phase supernatant liquor,
Again by methyl iso-butyl ketone (MIBK) stirring mixed with water, organic phase and aqueous phase are centrifuged；The methyl being distilled off in organic phase is different
Butyl ketone, arene compound of lignin oxidation's degraded generation based on vanillic aldehyde and guaiacol is obtained, water is distilled off
Moisture in phase, eutectic solvent is obtained, circulate and degraded for lignin electrochemical oxidation.
Embodiment 2
A kind of method of the electrochemical degradation lignin in eutectic solvent, through the following steps that realize：
（1）Choline hydrochloride and ethylene glycol press 1:2 ratio Hybrid Heating, the colourless eutectic solvent of homogeneous transparent is obtained,
It is introduced into sulfonic lignin and is dissolved in eutectic solvent and form homogeneous system, the concentration of lignin is 20g/L；
（2）The lignin homogeneous system prepared is added in the electrolytic cell of three electrodes composition, using platinum electrode as work
Electrode, carbon electrode are auxiliary electrode, and reference electrode is saturated calomel electrode, set oxidizing potential as 1V, reaction time 24h,
Electro-catalytic Oxidation Process lignin, guaiacol yield are 38%, and vanillic aldehyde yield is 37%, lignin conversion rate 95%；
（3）By VAcid：VElectrolyteFor 1:Electrolyte of 10 ratio after 0. 1mol/L watery hydrochloric acid diluting reaction, filtering are received
Collection separates out insoluble lignin and further degraded as raw material；Ethyl acetate is made solvable wooden in organic extractant phase supernatant liquor
Element, then by methyl iso-butyl ketone (MIBK) stirring mixed with water, centrifuge organic phase and aqueous phase；The methyl in organic phase is distilled off
Isobutyl ketone, arene compound of lignin oxidation's degraded generation based on vanillic aldehyde and guaiacol is obtained, is distilled off
Moisture in aqueous phase, eutectic solvent is obtained, circulate and degraded for lignin electrochemical oxidation.
Embodiment 3
A kind of method of the electrochemical degradation lignin in eutectic solvent, through the following steps that realize：
（1）N, N- diethylaluminum ethoxide ammonium chloride and glycerine press 1:3 ratio Hybrid Heating, it is colourless to obtain homogeneous transparent
Eutectic solvent, is introduced into sulfonic lignin and is dissolved in eutectic solvent and form homogeneous system, and the concentration of lignin is
40g/L；
（2）The lignin homogeneous system prepared is added in the electrolytic cell of three electrodes composition, using gold as working electrode,
Platinum electrode is auxiliary electrode, and reference electrode is hydrogen electrode, sets oxidizing potential as 1V, reaction time 3h, electrocatalytic oxidation drop
Lignin is solved, guaiacol yield is 36%, and vanillic aldehyde yield is 35%, lignin conversion rate 85%；
（3）By VAcid：VElectrolyteFor 1:Electrolyte of 20 ratio after 0.02mol/L dust technology diluting reaction, filtering are received
Collection separates out insoluble lignin and further degraded as raw material；Ethyl acetate is made solvable wooden in organic extractant phase supernatant liquor
Element, then by methyl iso-butyl ketone (MIBK) stirring mixed with water, centrifuge organic phase and aqueous phase；The methyl in organic phase is distilled off
Isobutyl ketone, arene compound of lignin oxidation's degraded generation based on vanillic aldehyde and guaiacol is obtained, is distilled off
Moisture in aqueous phase, eutectic solvent is obtained, circulate and degraded for lignin electrochemical oxidation.
Embodiment 4
A kind of method of the electrochemical degradation lignin in eutectic solvent, through the following steps that realize：
（1）Methyltriphenylphosphonium bromide and ethylene glycol press 1:3 ratio Hybrid Heating, obtain colourless low common of homogeneous transparent
Molten solvent, is introduced into sulfonic lignin and is dissolved in eutectic solvent and form homogeneous system, and the concentration of lignin is 80g/L；
（2）The lignin homogeneous system prepared is added in the electrolytic cell of three electrodes composition, using copper as working electrode,
Platinum electrode is auxiliary electrode, and reference electrode is silver/silver chloride electrode, sets oxidizing potential as 0.5V, reaction time 10h, electricity
Catalyzing oxidizing degrading lignin, guaiacol yield are 38%, and vanillic aldehyde yield is 37%, lignin conversion rate 90%；
（3）By VAcid：VElectrolyteFor 1:Electrolyte of 4 ratio after 0.05mol/L dilute sulfuric acid diluting reaction, is collected by filtration
Insoluble lignin is separated out further to degrade as raw material；Ethyl acetate makees the solvable lignin in organic extractant phase supernatant liquor,
Again by methyl iso-butyl ketone (MIBK) stirring mixed with water, organic phase and aqueous phase are centrifuged；The methyl being distilled off in organic phase is different
Butyl ketone, arene compound of lignin oxidation's degraded generation based on vanillic aldehyde and guaiacol is obtained, water is distilled off
Moisture in phase, eutectic solvent is obtained, circulate and degraded for lignin electrochemical oxidation.
Embodiment 5
A kind of method of the electrochemical degradation lignin in eutectic solvent, through the following steps that realize：
（1）N, N- diethylaluminum ethoxide ammonium chloride, methyltriphenylphosphonium bromide and ethylene glycol press 1:3:12 ratio mixing adds
Heat, obtain the colourless eutectic solvent of homogeneous transparent, be introduced into sulfonic lignin be dissolved in eutectic solvent formed it is homogeneous
System, the concentration of lignin is 10g/L；
（2）The lignin homogeneous system prepared is added in the electrolytic cell of three electrodes composition, using nickel as working electrode,
Platinum electrode is auxiliary electrode, and reference electrode is silver/silver chloride electrode, sets oxidizing potential as 1V, reaction time 15h, electricity is urged
Change oxidative degradation lignin, guaiacol yield is 38%, and vanillic aldehyde yield is 37%, lignin conversion rate 92%；
（3）By VAcid：VElectrolyteFor 1:Electrolyte of 2 ratio after 0.06mol/L dilute sulfuric acid diluting reaction, is collected by filtration
Insoluble lignin is separated out further to degrade as raw material；Ethyl acetate makees the solvable lignin in organic extractant phase supernatant liquor,
Again by methyl iso-butyl ketone (MIBK) stirring mixed with water, organic phase and aqueous phase are centrifuged；The methyl being distilled off in organic phase is different
Butyl ketone, arene compound of lignin oxidation's degraded generation based on vanillic aldehyde and guaiacol is obtained, water is distilled off
Moisture in phase, eutectic solvent is obtained, circulate and degraded for lignin electrochemical oxidation.
Embodiment 6
A kind of method of the electrochemical degradation lignin in eutectic solvent, through the following steps that realize：
（1）N, N- diethylaluminum ethoxide ammonium chloride, ethylene glycol and glycerine press 1:1:3 ratio Hybrid Heating, obtain uniformly
The eutectic solvent of clear, colorless, is introduced into sulfonic lignin and is dissolved in eutectic solvent and form homogeneous system, lignin
Concentration be 5g/L；
（2）The lignin homogeneous system prepared is added in the electrolytic cell of three electrodes composition, using nickel as working electrode,
Platinum electrode is auxiliary electrode, and reference electrode is silver/silver chloride electrode, sets oxidizing potential as 1V, reaction time 20h, electricity is urged
Change oxidative degradation lignin, guaiacol yield is 38%, and vanillic aldehyde yield is 37%, lignin conversion rate 94%；
（3）By VAcid：VElectrolyteFor 1:Electrolyte of 4 ratio after 0.01mol/L dust technology diluting reaction, is collected by filtration
Insoluble lignin is separated out further to degrade as raw material；Ethyl acetate makees the solvable lignin in organic extractant phase supernatant liquor,
Again by methyl iso-butyl ketone (MIBK) stirring mixed with water, organic phase and aqueous phase are centrifuged；The methyl being distilled off in organic phase is different
Butyl ketone, arene compound of lignin oxidation's degraded generation based on vanillic aldehyde and guaiacol is obtained, water is distilled off
Moisture in phase, eutectic solvent is obtained, circulate and degraded for lignin electrochemical oxidation.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
God any modification, equivalent substitution and improvements made etc., should be included in the scope of the protection with principle.
Claims (6)
- A kind of 1. method of the electrochemical degradation lignin in eutectic solvent, it is characterised in that comprise the following steps：（1）Sulfonation processing will be passed through first it be introduced into sulfonic lignin and be dissolved in eutectic solvent and form homogeneous system；（2）By the lignin homogeneous system prepared be added to three electrodes composition electrolytic cell in, with working electrode be selected from nickel, One kind in platinum, gold, copper electrode, auxiliary electrode are platinum electrode or carbon electrode, and reference electrode is selected from silver/silver chloride electrode, saturation One kind in calomel electrode or hydrogen electrode, electrolytic cell is formed, the electro-catalysis under the conditions of oxidizing potential is 0.5-1V, reacts 1-24h Oxidative degradation lignin is to produce vanillic aldehyde and guaiacol；Wherein, the eutectic solvent salt and hydrogen bond donor by being made up of, and wherein salt is selected from choline hydrochloride, methyl triphenyl Bromide phosphine, N, the one or more in N- diethylaluminum ethoxide ammonium chlorides, hydrogen bond donor is by urea, ethylene glycol, glycerine What one or more material mixings formed.
- 2. the method for electrochemical degradation lignin as claimed in claim 1, it is characterised in that：Step（1）In, the homogeneous body The concentration of lignin is 0.1-100g/L in system.
- 3. the method for electrochemical degradation lignin as claimed in claim 1, it is characterised in that also include：It is electrolysed after recovery reaction Lignin and eutectic solvent in liquid are recycled.
- 4. the method for electrochemical degradation lignin as claimed in claim 3, it is characterised in that：With the electrolysis after sour diluting reaction Liquid, it is collected by filtration and separates out insoluble lignin；By the solvable lignin in organic extractant phase supernatant liquor, then by methyl-isobutyl Ketone stirring mixed with water, centrifuge organic phase and aqueous phase；The methyl iso-butyl ketone (MIBK) in organic phase is distilled off, obtains wooden Arene compound caused by plain oxidative degradation, the moisture in aqueous phase is distilled off, obtains eutectic solvent, circulate for wooden Plain electrochemical oxidation degraded.
- 5. the method for electrochemical degradation lignin as claimed in claim 4, it is characterised in that：The acid of dilute electrolyte is dilute sulphur One kind in acid, watery hydrochloric acid, dust technology, acid ion concentration are 0.001-0.1 mol/L, and the volume ratio of acid and electrolyte is （1-20）：1.
- 6. the method for electrochemical degradation lignin as claimed in claim 4, it is characterised in that：The organic phase is acetic acid second Ester.
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| CN108823595B (en) * | 2018-07-12 | 2020-05-01 | 东北石油大学 | Method for electrolyzing lignin at high temperature in solar STEP process |
| CN109680296B (en) * | 2018-12-24 | 2020-11-03 | 河北工业大学 | Method for preparing eugenol by reacting ortho-methoxyphenol group decomposed from lignin with additional allyl |
| CN109518209B (en) * | 2019-01-15 | 2020-08-25 | 河北工业大学 | Method for preparing 3-tert-butyl 4-hydroxyanisole by electrocatalysis of 4-hydroxyanisole unit and tert-butyl chloride in lignin |
| CN113088542B (en) * | 2021-04-23 | 2023-10-24 | 淮阴师范学院 | Biomass pretreatment process and solvent recovery method used in treatment process thereof |
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