CN105199119B - A kind of method for making industrial lignin light - Google Patents
A kind of method for making industrial lignin light Download PDFInfo
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- CN105199119B CN105199119B CN201510600300.8A CN201510600300A CN105199119B CN 105199119 B CN105199119 B CN 105199119B CN 201510600300 A CN201510600300 A CN 201510600300A CN 105199119 B CN105199119 B CN 105199119B
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Abstract
The present invention discloses a kind of method for making industrial lignin light.1~5 parts by weight lignin is first dissolved in 500~20000 weight parts organic solvents by this method, forms lignin liquor；After lignin liquor magnetic agitation equilibrium, with ultraviolet light or visible light source irradiation 1~200 it is small when, obtain the lignin liquor of obvious light；The light lignin liquor of 1~10 parts by weight is added to the petroleum ether of 20~100 parts by weight, separates out lignin solid, after a large amount of distilled water flushings, the lignin solid powder of light color is obtained by freeze-drying.The method of the present invention is a step light method, and easy to operate, suitable for a variety of lignin, the organic solvent used in production process can reuse；Add oxidation processes compared to more traditional end-blocking, photo-irradiation treatment has the characteristics that low energy consumption, low cost, environmentally protective.The presence of lignin color is the main reason for paper pulp is dark, and the method for the present invention, which is used in Bleaching Technology, also good effect.
Description
Technical field
The present invention relates to lignin processing, more particularly to a kind of method for making industrial lignin light, belongs to natural height
The technical field of the derivative of molecular compound.
Background technology
Lignin is the second largest renewable resource that cellulose is only second in nature.Plant every year may be used by photosynthesis
Produce about 150,000,000,000 tons of lignin.In the industry based on cellulose such as pulping and paper-making, bio-ethanol, weaving, lignin is past
Discharged toward as byproduct.At present, less than 10%, most lignin are burned to return the effective rate of utilization of lignin for alkali
Receive, utilization rate is low and investment is huge.One of the reason for industrial lignin can not be utilized efficiently is that its colourity is deeper, if can find
A kind of environmentally friendly, simple light method, prepares light color or the lignin of white, the high-value-use of lignin will be wider
It is general, so as to play biomass resource advantage, improve the ecological environment.
Make industrial lignin light now, the research of the light lignin of preparation is simultaneously few.Chinese invention patent
2012105385177 disclose one plant of rice endophyte Pantoeasp.Sd-1 for being used for high-efficiency lignin degrading, and preserving number is
CGMCCNo.6698.The rice endophyte of the invention fades using alkali lignin as sole carbon source in 4 days postindustrial lignin of culture
Rate respectively reaches 52.38% and 69.06% with degradation rate.This method uses endophyte, complicates system, of high cost, and
And compare the property of heavy damage lignin in itself, influence its application.U.S. patent Nos US4184845, which discloses one kind, to be made
The method of sulfonation industry alkali lignin light, which is blocked phenolic hydroxyl group using propylene oxide or dimethyl suflfate, then is made
Desalination lignin color is aoxidized with air or oxygen, the colourity of lignin more than 80% can be eliminated.U.S. patent Nos
US4454066 discloses another method for making lignosulfonates fade and is equally first blocked phenolic hydroxyl group with alkylene oxide, subsequently
Aoxidized using the chloro- 2 hydroxyl -1- propyl sulfonic acids sodium of sulfuric acid or 3-, can be by lignosulfonates light.Both approaches are logical
Cross seal off phenolic hydroxyl group and further oxidation make industrial lignin light, it is necessary to which more reaction reagent, energy consumption is higher, and process
It is complicated.Qian etc. by alkali lignin acetylation by obtaining more light lignin, then by organic to acetylation lignin
Solution adds the method for water to make acetylation lignin self assembly, obtains the more shallow acetylation lignin nano-colloid ball of color
(QianY；DengYH；Li H；Qiu XQ,Reaction‐Free Lignin Whitening via a Self‐Assembly
of Acetylated Lignin,Green Chem,2014,53:24.).This method is more environmentally protective, but process is still
It is more complicated.
On the other hand, the paper pulp in present paper industry is broadly divided into mechanical pulp, chemical pulp according to processing method
And chemimechanical pulp；Refined pulp, bleached pulp, unbleached pulp, high-yield pulp, half chemical are divided into according to different purity
Slurry etc..Wherein, not only energy consumption is low, pollution is relatively fewer for high yield pulp (referring generally to mechanical pulp), but also is obtained relative to chemical pulp
Extracting rate is high.But the whiteness problem of high yield pulp become restrict its widely applied key issue, and paper pulp float
White process is to remove the process of lignin color, and the presence of lignin is the main reason for paper pulp is dark.In pulping and paper-making,
Traditional chlorine bleach, such as Chlorinated Bleaching, hypochlorite bleaching etc., can by association with pulp bleaching to certain whiteness, and cost compared with
It is low, but the chlorine-containing organic compounds such as more bioxin and chloroform can be produced in its bleaching process, these organic substance environments and life
State pollution is very big.Development is more environmentally friendly to become main trend completely without chlorine (TCF) bleaching, and this method is a kind of completely without chlorine drift
In vain.
The content of the invention
It is an object of the present invention to for the colourity problem (high level as influenced lignin caused by existing existing lignin
Utilize), there is provided one kind is suitable for a variety of lignin, and low energy consumption, low cost is environmentally protective, easy to operate simple industry wood
One step light method of quality.
The existing method for making industrial lignin fade is all complex, and for existing issue, the present invention provides one kind
Natural light, required organic reagent tetrahydrochysene can be selected in simple and effective one step light method of industrial lignin, light source needed for process
Furans may be recovered recycling, has and is suitable for a variety of lignin, low energy consumption, and low cost is environmentally protective, easy to operate simple
The advantages that, substantially retrieve, not yet find the similar method for making industrial lignin light.
As dark brown, the whiteness of its residual effect paper, is applied industrial lignin sheet as dye dispersant etc.
When influence product colourity.Some existing prior arts are how processing makes its lighter the problem of.But the prior art deposits body
The problems such as being complicated, of high cost, high energy consumption.Inventor has found：General illumination will not make the lighter of industrial lignin, and
And be placed on illumination in usual vehicle and can not make the lighter of industrial lignin, lignin is only in tetrahydrofuran, 2- methyl
One in tetrahydrofuran, 2- methylfurans, 2- chloromethyls tetrahydrofuran, dioxane, six ring of 4- methyl-1,3-dioxies and crown ether
Lignin liquor is formed in the solvent of kind, the lignin of obvious light can be just being obtained by ultraviolet light or visible light source irradiation
Solution (in the process, illumination makes above-mentioned organic solvent produce peroxy radical while lignin is produced Phenoxy radical,
Main chromophore existing for script in lignin is reduced by radical reaction：Quinoid structure；The mistake herein of lignin at the same time
π-π effects are reduced in journey, also make wooden to be known as light effect)；Add petroleum ether and separate out lignin solid, be dried to obtain light color
Lignin solid powder.The method of the present invention environmental protection, energy consumption is low, and cost is low.
The purpose of the present invention is achieved through the following technical solutions：
A kind of method for making industrial lignin light, comprises the following steps：
(1) 1~5 parts by weight lignin is dissolved in 500~20000 weight parts organic solvents, forms lignin liquor；Institute
Organic solvent is stated as tetrahydrofuran, 2- methyltetrahydrofurans, 2- methylfurans, 2- chloromethyls tetrahydrofuran, dioxane, 4- first
One kind in base -1,3- dioxane and crown ether；
(2) by after the lignin liquor magnetic agitation equilibrium in step (1), 1~200 is irradiated with ultraviolet light or visible light source
Hour, obtain the lignin liquor of obvious light；
(3) the light lignin liquor of 1~10 parts by weight in step (2) is added to the oil of 20~100 parts by weight
Ether, separates out lignin solid, and after a large amount of distilled water flushings, the lignin solid powder of light color is obtained by freeze-drying.
In order to further realize the object of the invention, it is preferable that lignin used is wooden from wood pulp alkali in step (1)
Element, bamboo pulp alkali lignin, Straw Pulp alkali lignin, enzymolysis xylogen, organic solvent extraction type lignin and by alkali lignin
One or more mixtures in acetylation lignin made from modification.
Preferably, concentration is 0.05g/L~10g/L to lignin in organic solvent in step (1).
Preferably, the rotating speed of the magnetic agitation is 100~1000 rpms, and the time is 1~30min.
Preferably, it is one or more in deuterium lamp, helium lamp, tungsten lamp and natural light that the visible light source, which is,.
Preferably, the power of the ultraviolet light is 10~200W, and wavelength is 200~800nm.
The present invention compared with the prior art, has the advantage that and effect：
1st, the present invention can make the industrial lignin light in solution using illumination, and illumination makes organic solvent produce peroxide
Free radical, makes lignin produce Phenoxy radical, reduces quinoid color group existing for script in lignin by radical reaction
Structure；π-π effects are also corresponding in lignin molecule at the same time weakens, and two aspect factors cause industrial lignin light.
2nd, the present invention can make a variety of industrial lignin lights, and required light source is chosen as sunlight, and solvent for use can return
Receive, while without using bleaching agent, there is applied widely, low energy consumption, low cost, environmentally protective.
3rd, the present invention can make industrial lignin light using illumination, and process is one-step method, than existing light side
Method, this method is easy, and light positive effect.
Brief description of the drawings
Fig. 1 is ultraviolet spectrogram before and after 1 alkali lignin illumination of embodiment.
Fig. 2 is fluorescence spectra before and after 1 alkali lignin illumination of embodiment.
Fig. 3 is grain size distribution before and after 1 alkali lignin illumination of embodiment.
Embodiment
To more fully understand the present invention, the present invention is described in detail with reference to the accompanying drawings and examples, still
The implementation of the present invention is not limited to this.
Embodiment 1
(1) 30mg wood pulp alkali lignins are placed in 100mL serum bottles, add 60mL tetrahydrofurans, obtain 500mg/L's
Alkali lignin tetrahydrofuran solution.With 1000 rpms of speed magnetic agitation 10 minutes, solution is uniformly mixed, obtains depth
The solution of brown.
(2) it is alkali lignin tetrahydrofuran solution 100W, 365nm the length ultraviolet light irradiation 80 obtained by step (1) is small
When.Solution colour substantially shoals after illumination, is changed into faint yellow from dark-brown.
(3) the alkali lignin tetrahydrofuran solution after the colour fading that will be obtained in step (2) is separated out with petroleum ether, tetrahydrofuran
Mass ratio with petroleum ether is 1：5.After a large amount of distilled water flushings, freeze-drying obtains the alkali lignin solid powder of light color.
From the alkali lignin solid powder color before and after illumination can be seen that illumination after solid powder color substantially shoal, by sepia
It is changed into faint yellow.
(4) it is 25mg/L that the alkali lignin tetrahydrofuran solution after the colour fading that will be obtained in step (2), which is diluted to concentration, into
Row ultraviolet spectra is tested.Fig. 1 be by Japanese Shimadzu UV-2450 it is ultraviolet-illumination that measures of visible spectrophotometer before and after alkali
The ultraviolet spectrogram of lignin liquor.As shown in Figure 1, absorbance is decreased obviously after illumination, (lignin is represented at 450nm
Colourity) absorbance drop to 0.0199 from 0.0723, and blue shift occurs, shows that the part chromophoric group of alkali lignin is destroyed
And there occurs π-π depolymerization so that lighter.
(5) the alkali lignin tetrahydrofuran solution after fading in step (2) is subjected to fluorescence spectrum test.Fig. 2 is to pass through
The fluorescence emission spectrogram of compound of alkali lignin before and after the illumination that Hitachi, Japan F-4500 Fluorescence Spectrometer measures, excitation wavelength selection
420nm.It can be seen that the fluorescence emission spectrum emission peak of alkali lignin is had been moved at 499.2nm at 506.8nm, also have obvious
Blue-shifted phenomenon, again showing that alkali lignin, there occurs π-π depolymerization so that lighter.
(6) the alkali lignin tetrahydrofuran solution after fading in step (2) is subjected to particle diameter test.Fig. 3 is to pass through the U.S.
Grain size distribution before and after the illumination that Brooker sea text ZetaPALS Zeta potential analyzers measure.It can be seen that lignin
Grain is obviously reduced, and is reduced to 121.11nm and 594.34nm from 291.16nm and 3513.31nm respectively, shows alkali lignin
π-π depolymerization, molecule particles diminish so that lignin lighter.
Embodiment 2
(1) the acetylation lignin that 10mg wood pulp alkali lignin acetylated modifications obtain is placed in 100mL serum bottles, added
Enter 40mL tetrahydrofurans, obtain the acetylation lignin tetrahydrofuran solution of 250mg/L.With 100 rpms of speed magnetic force
Stirring 10 minutes, is uniformly mixed solution.
(2) by the acetylation lignin tetrahydrofuran solvent obtained by step (1) with deuterium lamp irradiation 55 it is small when, substantially taken off
The acetylation lignin tetrahydrofuran solution of color.
(3) the acetylation lignin tetrahydrofuran solution after the colour fading that will be obtained in step (2) is separated out with petroleum ether, both
Mass ratio is 1：7.5.After a large amount of distilled water flushings, freeze-drying obtains the acetylation lignin solid powder of light color.
(4) using ultraviolet spectroscopy same as Example 1, fluorescence emission spectrum measure and particle size distribution measuring, knot
Fruit is essentially identical with Fig. 1, Fig. 2, Fig. 3 respectively.
Embodiment 3
(1) 30mg bamboo pulp alkali lignins are placed in 100mL serum bottles, add 60mL dioxane, obtain 500mg/L's
Alkali lignin dioxane solution.With 550 rpms of speed magnetic agitation 15 minutes, it is uniformly mixed solution.
(2) by the alkali lignin dioxane obtained by step (1) with helium lamp irradiation 40 it is small when, substantially faded alkali wood
Quality dioxane solution.
(3) the alkali lignin dioxane solution after the colour fading that will be obtained in step (2) is separated out with petroleum ether, both quality
Than for 1：10.Freeze-drying obtains the alkali lignin solid powder of light color.
(4) using ultraviolet spectroscopy same as Example 1, fluorescence emission spectrum measure and particle size distribution measuring, knot
Fruit is essentially identical with Fig. 1, Fig. 2, Fig. 3 respectively.
Embodiment 4
(1) 100mg Wheat Straw Lignin from Alkali Pulping is placed in 100mL serum bottles, adds 50mL12- crown ether -4, obtain 2g/L's
Alkali lignin crown ether solution.With 600 rpms of speed magnetic agitation 30 minutes, it is uniformly mixed solution.
(2) by the lignin crown ether solution tungsten lamp irradiation 70 obtained by step (1) it is small when, the alkali lignin that is substantially faded
Crown ether solution.
(3) the alkali lignin crown ether solution after the colour fading that will be obtained in step (2) is separated out with petroleum ether, both are at mass ratio
1：5.5.After a large amount of distilled water flushings, freeze-drying obtains the alkali lignin solid powder of light color.
(4) using ultraviolet spectroscopy same as Example 1, fluorescence emission spectrum measure and particle size distribution measuring, knot
Fruit is essentially identical with Fig. 1, Fig. 2, Fig. 3 respectively.
Embodiment 5
(1) 200mg enzymolysis xylogens are placed in 100mL serum bottles, add 50mL2-methylfuran, obtain 4g/L's
Enzymolysis xylogen 2-methylfuran solution.With 600 rpms of speed magnetic agitation 20 minutes, it is uniformly mixed solution.
(2) by enzymolysis xylogen 2-methylfuran solution 100W, 254nm length ultraviolet light irradiation obtained by step (1)
80 it is small when, enzymolysis xylogen 2-methylfuran solution for substantially being faded.
(3) enzymolysis xylogen 2-methylfuran solution after the colour fading that will be obtained in step (2) is separated out with petroleum ether, and two
Person's mass ratio is 1：5.5.After a large amount of distilled water flushings, freeze-drying obtains the enzymolysis xylogen solid powder of light color.
(4) using ultraviolet spectroscopy same as Example 1, fluorescence emission spectrum measure and particle size distribution measuring, knot
Fruit is essentially identical with Fig. 1, Fig. 2, Fig. 3 respectively.
Embodiment 6
(1) 30mg organic solvent extraction type lignin is placed in 100mL serum bottles, adds 60mL2-chloromethyl tetrahydrochysene
Furans, obtains lignin 2-chloromethyl tetrahydrofuran solution of 500mg/L.Divided with 550 rpms of speed magnetic agitation 15
Clock, is uniformly mixed solution.
(2) by 2-chloromethyl of lignin tetrahydrofuran obtained by step (1) with helium lamp irradiation 40 it is small when, substantially taken off
Lignin 2-chloromethyl tetrahydrofuran solution of color.
(3) the alkali lignin dioxane solution after the colour fading that will be obtained in step (2) is separated out with petroleum ether, both quality
Than for 1：10.Freeze-drying obtains the lignin solid powder of light color.
(4) using ultraviolet spectroscopy same as Example 1, fluorescence emission spectrum measure and particle size distribution measuring, knot
Fruit is essentially identical with Fig. 1, Fig. 2, Fig. 3 respectively.
Embodiment 7
(1) 130mg bamboo pulp alkali lignins are placed in 100mL serum bottles, add 65mL2-methyltetrahydrofuran, obtain
Alkali lignin 2-methyltetrahydrofuran solution of 2g/L.With 600 rpms of speed magnetic agitation 45 minutes, mix solution
Close uniform.
(2) by obtained by step (1) lignin 2-methyltetrahydrofuran solution tungsten lamp irradiation 60 it is small when, substantially taken off
Alkali lignin 2-methyltetrahydrofuran solution of color.
(3) alkali lignin 2-methyltetrahydrofuran solution after the colour fading that will be obtained in step (2) is separated out with petroleum ether,
Both mass ratioes are 1：6.2.After a large amount of distilled water flushings, freeze-drying obtains the alkali lignin solid powder of light color.
(4) using ultraviolet spectroscopy same as Example 1, fluorescence emission spectrum measure and particle size distribution measuring, knot
Fruit is essentially identical with Fig. 1, Fig. 2, Fig. 3 respectively.
Embodiment 8
(1) 100mg Wheat Straw Lignin from Alkali Pulping is placed in 100mL serum bottles, adds 40mL4-methyl-1,3-dioxy six
Ring, obtains alkali lignin 4-methyl-1,3-dioxane solution of 2.5g/L.With 600 rpms of speed magnetic agitation
45 minutes, it is uniformly mixed solution.
(2) by lignin 4-methyl-1,3 obtained by step (1)-dioxane solution tungsten lamp irradiation 42 it is small when, obtain
Alkali lignin 4-methyl-1,3-the dioxane solution substantially faded.
(3) alkali lignin 4-methyl-1,3-dioxane solution oil after the colour fading that will be obtained in step (2)
Ether separates out, both mass ratioes are 1：5.8.After a large amount of distilled water flushings, freeze-drying obtains the alkali lignin solid powder of light color
End.
(4) using ultraviolet spectroscopy same as Example 1, fluorescence emission spectrum measure and particle size distribution measuring, knot
Fruit is essentially identical with Fig. 1, Fig. 2, Fig. 3 respectively.
Embodiment 9
(1) unbleached paper is placed in 100mL serum bottles, adds 50mL tetrahydrofurans, paper is all submerged.
(2) by paper 100W, the 365nm length ultraviolet light irradiation 50 submerged by tetrahydrofuran it is small when, paper substantially becomes
In vain, it is changed into from brown color close to white.Paper White Degree is tested by 110 spectrophotometer of DATACOLOR companies of the U.S..Do not bleach
Paper White Degree is 0.6540, and after being handled by this method, Paper White Degree has reached 0.9166 (whiteness maximum is 1).Paper floats
A white application as the method for the present invention, industrial lignin sheet is as dark brown, the whiteness of its residual effect paper.This reality
Ultra violet lamp will be used again in unbleached paper immersion tetrahydrofuran by applying example so that paper reaches higher whiteness, and energy consumption
It is low, pollution it is relatively fewer.Promote the use of the method for the present invention and substitute traditional chlorine bleach, such as Chlorinated Bleaching, hypochlorite bleaching
Deng, can to avoid being produced in bleaching process to the chlorine-containing organic compounds such as environment and the great bioxin of ecological pollution and chloroform,
Organic solvent is recyclable at the same time, has accomplished total chlorine free bleaching, green, economical, sustainable.
Claims (6)
- A kind of 1. method for making industrial lignin light, it is characterised in that comprise the following steps：(1) 1~5 parts by weight lignin is dissolved in 500~20000 weight parts organic solvents, forms lignin liquor；It is described to have Solvent for tetrahydrofuran, 2- methyltetrahydrofurans, 2- methylfurans, 2- chloromethyls tetrahydrofuran, dioxane, 4- methyl- One kind in 1,3- dioxane and crown ether；(2) by after the lignin liquor magnetic agitation equilibrium in step (1), it is small to irradiate 1~200 with ultraviolet light or visible light source When, obtain the lignin liquor of obvious light；(3) the light lignin liquor of 1~10 parts by weight in step (2) is added to the petroleum ether of 20~100 parts by weight, analysis Go out lignin solid, after a large amount of distilled water flushings, the lignin solid powder of light color is obtained by freeze-drying.
- 2. the method according to claim 1 for making industrial lignin light, it is characterised in that：Wood used in step (1) Quality is from wood pulp alkali lignin, bamboo pulp alkali lignin, Straw Pulp alkali lignin, enzymolysis xylogen, organic solvent extraction type Lignin and by one or more mixtures in alkali lignin modified obtained acetylation lignin.
- 3. the method according to claim 1 for making industrial lignin light, it is characterised in that：Lignin in step (1) Concentration is 0.05g/L~10g/L in organic solvent.
- 4. the method according to claim 1 for making industrial lignin light, it is characterised in that：The magnetic agitation turns Speed is 100~1000 rpms, and the time is 1~30min.
- 5. the method according to claim 1 for making industrial lignin light, it is characterised in that：The visible light source is yes One or more in deuterium lamp, helium lamp, tungsten lamp and natural light.
- 6. the method according to claim 1 for making industrial lignin light, it is characterised in that：The power of the ultraviolet light For 10~200W, wavelength is 200~800nm.
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| CN109012608A (en) * | 2018-07-10 | 2018-12-18 | 北京林业大学 | The preparation method and application of lignin nanosphere |
| CN114854040B (en) * | 2022-06-07 | 2023-08-22 | 西南交通大学 | Light-colored lignin and preparation method and application thereof |
| CN114874457B (en) * | 2022-06-07 | 2023-06-27 | 西南交通大学 | Method for regulating lignin color |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06128890A (en) * | 1992-10-20 | 1994-05-10 | Honshu Paper Co Ltd | Bleaching of pulp |
| CN1554826A (en) * | 2003-12-20 | 2004-12-15 | 广西大学 | Photochemical paper pulp bleaching method and device |
| CN102454129A (en) * | 2010-10-26 | 2012-05-16 | 李朝旺 | Fiber self-coupled oxidative decomposition cleaning papermaking method |
-
2015
- 2015-09-18 CN CN201510600300.8A patent/CN105199119B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06128890A (en) * | 1992-10-20 | 1994-05-10 | Honshu Paper Co Ltd | Bleaching of pulp |
| CN1554826A (en) * | 2003-12-20 | 2004-12-15 | 广西大学 | Photochemical paper pulp bleaching method and device |
| CN102454129A (en) * | 2010-10-26 | 2012-05-16 | 李朝旺 | Fiber self-coupled oxidative decomposition cleaning papermaking method |
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