CN107163260A - A kind of method for improving alkali lignin sulfonation yield - Google Patents
A kind of method for improving alkali lignin sulfonation yield Download PDFInfo
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Abstract
The invention belongs to improve alkali lignin reactivity field, a kind of method for improving alkali lignin sulfonation yield is disclosed.This method is by being pre-processed to alkali lignin to improve alkali lignin sulfonation yield, and the pretreatment comprises the following steps：Alkali lignin adds to the methylimidazole acetate of 1 ethyl 3 or the methylimidazole villaumite of 1 ethyl 3 are well mixed to be handled, water terminating reaction is added after the completion of processing, then centrifuged, be freeze-dried and obtain pretreated alkali lignin.Carry out vacuum distillation and reclaim the methylimidazole acetate of 1 ethyl 3 or the methylimidazole villaumite of 1 ethyl 3.The dissolving environmental protection used of the preprocess method of the present invention, can be with circulating and recovering, and pollution-free generation, technique is simple, it is easy to operate, suitable for industrialized production, has a good application prospect.
Description
Technical field
The invention belongs to improve alkali lignin reactivity field, and in particular to a kind of side of raising alkali lignin sulfonation yield
Method.
Background technology
Lignin, as one of the abundantest natural polymer of reserves on the earth, its reserves is only second to cellulose, occupies
Two.In world wide, about 3,000 ten thousand tons of lignin discarded objects are obtained by various chemical pulp processes every year.It is used as biomass essence
Accessory substance during refining, most lignin are burned off in alkali recovery process as fuel, but the calorific value of lignin
Low, the burning of a large amount of lignins causes the waste of biomass energy.Can be with higher value application lignin it would therefore be highly desirable to probe into out one kind
Method, so as to rationally utilize the biomass resource.
Lignin molecule contains substantial amounts of active group, such as methoxyl group, phenolic hydroxyl group, alcoholic extract hydroxyl group, carbon-carbon double bond, carbonyl, this
The presence of a little functional groups shows that lignin has the potential for preparing several functions material.Conventional lignin modified method includes sulphur
Change, graft copolymerization, amination, alkylation, oxidation, condensation etc..Sulfonating reaction is maximally efficient utilization lignin in the above method
Method of modifying.Lignin after sulfonation turns into sulfonated lignin, or lignosulphonates, at this stage extensively using surfactant, mixed
The numerous areas such as solidifying soil water reducer, tertiary oil recovery auxiliary agent, agricultural chemical agents.Exist between the molecular cell for constituting lignin a variety of
It is connected chemically, the activity that sulfonic group in 3 D stereo network structure, lignosulfonate modifying process is only capable of replacing lignin surface is presented
Group, sulfonic group is hard to permeate into lignin intramolecule, causes the intramolecular group of lignin to participate in sulfonating reaction, so that
Cause sulphonation rate low.To improve the sulfonation efficiency of lignin, Deng Guosong et al. is carried out at activation by highly basic oxidant to alkali lignin
Manage (Chinese papermaking, 2005,24 (12):29-32).The use of highly basic oxidant causes the increase of water pollution processing pressure, no
It is a kind of method of environmental protection.
The content of the invention
In place of shortcoming and defect in order to solve above prior art, alkali wood is improved it is an object of the invention to provide one kind
The method of plain sulfonation yield.
The object of the invention is achieved through the following technical solutions：
A kind of method for improving alkali lignin sulfonation yield, this method to alkali lignin by being pre-processed to improve alkali lignin
Sulfonation yield, the pretreatment comprises the following steps：By alkali lignin add 1- ethyl-3-methylimidazoles acetate or 1- ethyls-
3- methylimidazole villaumites are well mixed to be handled, and water terminating reaction is added after the completion of processing, is then centrifuged and freezed and be dry
It is dry to obtain pretreated alkali lignin.1- ethyl-3-methylimidazole acetate is reclaimed by vacuum distillation after the completion of above-mentioned reaction
Or 1- ethyl-3-methylimidazole villaumites.
Preferably, described alkali lignin includes needlebush, leaf wood or grass as raw material by all kinds of soda pulping process nights
The alkali lignin for extracting and coming, also including being commercialized all kinds of alkali lignins sold.
Preferably, the alkali lignin purity is 80~95%.
Preferably, the alkali lignin water content is 1~3%.
Preferably, the alkali lignin particle diameter is in 80~100 mesh.
Preferably, the purity of described 1- ethyl-3-methylimidazoles acetate or 1- ethyl-3-methylimidazole villaumites is 95
~99%.
Preferably, the consumption of 1- ethyl-3-methylimidazoles acetate or 1- the ethyl-3-methylimidazole villaumite is over dry
The 400%-500% of alkali lignin quality.
Preferably, the processing after the addition 1- ethyl-3-methylimidazoles acetate or 1- ethyl-3-methylimidazole villaumites
Temperature is 80~90 DEG C.
Preferably, the processing after the addition 1- ethyl-3-methylimidazoles acetate or 1- ethyl-3-methylimidazole villaumites
Time is 60~120min.
Preferably, the rotating speed of the centrifugation is 3000~3500r/min.
The preparation method and resulting product of the present invention has the following advantages that and beneficial effect：
(1) the green ring of 1- ethyl-3-methylimidazoles acetate or 1- ethyl-3-methylimidazoles villaumite used in the present invention
Protect, be easy to recycle.
(2) the method preparation technology for improving alkali lignin sulfonation yield is simple, it is easy to operate, suitable for industrialized production.
(3) reactivity of alkali lignin is significantly increased after pre-processing, and sulfonation efficiency is improved.
Embodiment
With reference to embodiment, the present invention is described in further detail, but the implementation of the present invention is not limited to this.
Embodiment 1
Taking the alkali lignin that the anthraquinone black liquor of pulp making of wheat straw soda extracts, (purity is 85%, and particle diameter is 80 mesh, and water content is
3%) the mixing pretreatment of 1- ethyl-3-methylimidazoles acetate, is added, deionized water terminating reaction is added after the completion of processing, with
(rotating speed 3000r/min), freeze-drying are centrifuged afterwards obtains pretreated alkali lignin.Carry out vacuum distillation and reclaim 1- second
Base -3- methylimidazole acetate.Treatment conditions are：The consumption of 1- ethyl-3-methylimidazole acetate is over dry alkali lignin quality
400%, treatment temperature be 80 DEG C, processing time is 60min.The sulfonation modifying technique of lignin is as follows：Pretreated alkali wood
Plain sample is added in deionized water, and the consumption of water is the 300% of lignin quality, magnetic agitation (300r/min, 20min), plus
Heat adds hydrogen peroxide to 95 DEG C, controls 95 DEG C of temperature, reacts 1 hour, is subsequently added formaldehyde and sodium sulfite, is kept for 95 DEG C
Lower reaction 3h, wherein formaldehyde consumption 40% (with respect to over dry lignin), sodium sulfite consumption are 30% (with respect to over dry lignin).
The sulfonation modifying technique of control group 1 is as follows：(purity is for alkali lignin that the anthraquinone black liquor of pulp making of wheat straw soda is extracted
85%, particle diameter is 80 mesh, and water content is 3%) to be added in deionized water, and the consumption of water is the 300% of lignin quality, and magnetic force is stirred
(300r/min, 20min) is mixed, 95 DEG C are heated to, 10% sodium hydroxide is added and is used as oxidant (with respect to over dry lignin), constant temperature
10-15min.Hydrogen peroxide is added, hydrogen peroxide use is 1% (with respect to over dry lignin), controls 95 DEG C of temperature, reacts 1 hour,
Formaldehyde and sodium sulfite are subsequently added, keeps reacting 3h, wherein formaldehyde consumption 40% (with respect to over dry lignin), sulfurous acid at 95 DEG C
Sodium consumption is 30% (with respect to over dry lignin).
The contrast table of the different pretreatments method lignosulfonate efficiency of table 1
| Sample | Sulfonation degree (mmol/g) | Solubility (%) (pH=7,25 DEG C) in water |
| Embodiment 1 | 1.65 | 95.5 |
| Control group 1 | 1.50 | 90.4 |
The data of table 1 can be seen that using the pretreated alkali lignin sulfonation degree of 1- ethyl-3-methylimidazole acetate than strong
Alkali lignin after alkali oxidation processes improves 10%, and the solubility in water improves 5.6%, the raising of sulfonation degree and solubility, table
Face can significantly improve the sulfonation efficiency of wheat straw alkali lignin by the pretreatment of 1- ethyl-3-methylimidazoles acetate.
Embodiment 2
Taking the alkali lignin that the alkaline sulfurous method black liquor of pulp making of Eucalyptus extracts, (purity is 80%, and particle diameter is 85 mesh, and water content is
1%) the mixing pretreatment of 1- ethyl-3-methylimidazoles acetate, is added, deionized water terminating reaction is added after the completion of processing, with
(rotating speed 3200r/min), freeze-drying are centrifuged afterwards obtains pretreated alkali lignin.Carry out vacuum distillation and reclaim 1- second
Base -3- methylimidazole acetate.Treatment conditions are：The consumption of 1- ethyl-3-methylimidazole acetate is over dry alkali lignin quality
450%, treatment temperature be 85 DEG C, processing time is 90min.The sulfonation modifying technique of lignin is as follows：Pretreated alkali wood
Plain sample is added in deionized water, and the consumption of water is the 300% of lignin quality, magnetic agitation (300r/min, 20min), plus
Heat adds hydrogen peroxide to 95 DEG C, controls 95 DEG C of temperature, reacts 1 hour, is subsequently added formaldehyde and sodium sulfite, is kept for 95 DEG C
Lower reaction 3h, wherein formaldehyde consumption 40% (with respect to over dry lignin), sodium sulfite consumption are 30% (with respect to over dry lignin).
The sulfonation modifying technique of control group 2 is as follows：Taking alkali lignin that the alkaline sulfurous method black liquor of pulp making of Eucalyptus extracts, (purity is
80%, particle diameter is 85 mesh, and water content is 1%), to be added in deionized water, and the consumption of water is the 300% of lignin quality, magnetic force
Stir (300r/min, 20min), be heated to 95 DEG C, add 10% sodium hydroxide and be used as oxidant (with respect to over dry lignin), constant temperature
10-15min.Hydrogen peroxide is added, hydrogen peroxide use is 1% (with respect to over dry lignin), controls 95 DEG C of temperature, reacts 1 hour,
Formaldehyde and sodium sulfite are subsequently added, keeps reacting 3h, wherein formaldehyde consumption 40% (with respect to over dry lignin), sulfurous acid at 95 DEG C
Sodium consumption is 30% (with respect to over dry lignin).
The contrast table of the different pretreatments method lignosulfonate efficiency of table 2
| Sample | Sulfonation degree (mmol/g) | Solubility (%) (pH=7,25 DEG C) in water |
| Embodiment 2 | 1.61 | 94.3 |
| Control group 2 | 1.40 | 87.7 |
The data of table 2 can be seen that using the pretreated alkali lignin sulfonation degree of 1- ethyl-3-methylimidazole acetate than strong
Alkali lignin after alkali oxidation processes improves 15%, and the solubility in water improves 7.5%, the raising of sulfonation degree and solubility, table
Face can significantly improve the sulfonation efficiency of Eucalyptus alkali lignin by the pretreatment of 1- ethyl-3-methylimidazoles acetate.
Embodiment 3
Taking commercialization alkali lignin, (purity is 95%, and particle diameter is 90 mesh, and water content is 2%), to add 1- ethyl -3- methyl miaows
The mixing pretreatment of azoles acetate, adds deionized water terminating reaction, is then centrifuged (rotating speed 3500r/ after the completion of processing
Min), freeze-drying obtains pretreated alkali lignin.Carry out vacuum distillation and reclaim 1- ethyl-3-methylimidazole acetate.Place
Manage bar part is：The consumption of 1- ethyl-3-methylimidazole acetate is the 500% of over dry alkali lignin quality, and treatment temperature is 90 DEG C,
Processing time is 120min.The sulfonation modifying technique of lignin is as follows：Pretreated alkali lignin sample is added in deionized water,
The consumption of water is the 300% of lignin quality, and magnetic agitation (300r/min, 20min) is heated to 95 DEG C, adds hydrogen peroxide, control
95 DEG C of temperature processed, reacts 1 hour, is subsequently added formaldehyde and sodium sulfite, keeps reacting 3h, wherein formaldehyde consumption 40% at 95 DEG C
(with respect to over dry lignin), sodium sulfite consumption is 30% (with respect to over dry lignin).
The sulfonation modifying technique of control group 3 is as follows：Being commercialized alkali lignin, (purity is 95%, and particle diameter is 90 mesh, and water content is
2%) it is added in deionized water, the consumption of water is the 300% of lignin quality, magnetic agitation (300r/min, 20min), heating
To 95 DEG C, add 10% sodium hydroxide and be used as oxidant (with respect to over dry lignin), constant temperature 10-15min.Add hydrogen peroxide, mistake
Hydrogen oxide consumption is 1% (with respect to over dry lignin), controls 95 DEG C of temperature, reacts 1 hour, is subsequently added formaldehyde and sodium sulfite,
Keep reacting 3h, wherein formaldehyde consumption 40% (with respect to over dry lignin) at 95 DEG C, sodium sulfite consumption is 30% (with respect to over dry wood
Element).
The contrast table of the different pretreatments method lignosulfonate efficiency of table 3
| Sample | Sulfonation degree (mmol/g) | Solubility (%) (pH=7,25 DEG C) in water |
| Embodiment 3 | 1.68 | 95.9 |
| Control group 3 | 1.54 | 91.3 |
The data of table 3 can be seen that using the pretreated alkali lignin sulfonation degree of 1- ethyl-3-methylimidazole acetate than strong
Alkali lignin after alkali oxidation processes improves 9%, and the solubility in water improves 5.0%, the raising of sulfonation degree and solubility, surface
The sulfonation efficiency of commercialization alkali lignin can be significantly improved by being pre-processed by 1- ethyl-3-methylimidazoles acetate.
Embodiment 4
Taking the alkali lignin that the anthraquinone black liquor of pulp making of wheat straw soda extracts, (purity is 85%, and particle diameter is 80 mesh, and water content is
2%) the mixing pretreatment of 1- ethyl-3-methylimidazoles villaumite, is added, deionized water terminating reaction is added after the completion of processing, then
Centrifuged (rotating speed 3000r/min), freeze-drying and obtain pretreated alkali lignin.Progress vacuum distillation recovery 1- ethyls-
3- methylimidazole villaumites.Treatment conditions are：The consumption of 1- ethyl-3-methylimidazole villaumites is the 400% of over dry alkali lignin quality,
Treatment temperature is 80 DEG C, and processing time is 60min.The sulfonation modifying technique of lignin is as follows：Pretreated alkali lignin sample adds
Enter into deionized water, the consumption of water is the 300% of lignin quality, and magnetic agitation (300r/min, 20min) is heated to 95 DEG C,
Hydrogen peroxide is added, 95 DEG C of temperature is controlled, reacted 1 hour, formaldehyde and sodium sulfite is subsequently added, keeps reacting 3h at 95 DEG C,
Wherein formaldehyde consumption 40% (with respect to over dry lignin), sodium sulfite consumption is 30% (with respect to over dry lignin).
The sulfonation modifying technique of control group 4 is as follows：(purity is for alkali lignin that the anthraquinone black liquor of pulp making of wheat straw soda is extracted
85%, particle diameter is 80 mesh, and water content is 2%) to be added in deionized water, and the consumption of water is the 300% of lignin quality, and magnetic force is stirred
(300r/min, 20min) is mixed, 95 DEG C are heated to, 10% sodium hydroxide is added and is used as oxidant (with respect to over dry lignin), constant temperature
10-15min.Hydrogen peroxide is added, hydrogen peroxide use is 1% (with respect to over dry lignin), controls 95 DEG C of temperature, reacts 1 hour,
Formaldehyde and sodium sulfite are subsequently added, keeps reacting 3h, wherein formaldehyde consumption 40% (with respect to over dry lignin), sulfurous acid at 95 DEG C
Sodium consumption is 30% (with respect to over dry lignin).
The contrast table of the different pretreatments method lignosulfonate efficiency of table 4
| Sample | Sulfonation degree (mmol/g) | Solubility (%) (pH=7,25 DEG C) in water |
| Embodiment 4 | 1.61 | 95.1 |
| Control group 4 | 1.51 | 90.5 |
The data of table 4 can be seen that compares highly basic using the pretreated alkali lignin sulfonation degree of 1- ethyl-3-methylimidazole villaumites
Alkali lignin after oxidation processes improves 6%, the solubility raising 5.1% in water, the raising of sulfonation degree and solubility, and surface is borrowed
The pretreatment of 1- ethyl-3-methylimidazoles villaumite is helped to significantly improve the sulfonation efficiency of wheat straw alkali lignin.
Embodiment 5
Taking the alkali lignin that the alkaline sulfurous method black liquor of pulp making of Eucalyptus extracts, (purity is 80%, and particle diameter is 90 mesh, and water content is
1%) the mixing pretreatment of 1- ethyl-3-methylimidazoles villaumite, is added, deionized water terminating reaction is added after the completion of processing, then
Centrifuged (rotating speed 3300r/min), freeze-drying and obtain pretreated alkali lignin.Progress vacuum distillation recovery 1- ethyls-
3- methylimidazole villaumites.Treatment conditions are：The consumption of 1- ethyl-3-methylimidazole villaumites is the 450% of over dry alkali lignin quality,
Treatment temperature is 85 DEG C, and processing time is 100min.The sulfonation modifying technique of lignin is as follows：Pretreated alkali lignin sample adds
Enter into deionized water, the consumption of water is the 300% of lignin quality, and magnetic agitation (300r/min, 20min) is heated to 95 DEG C,
Hydrogen peroxide is added, 95 DEG C of temperature is controlled, reacted 1 hour, formaldehyde and sodium sulfite is subsequently added, keeps reacting 3h at 95 DEG C,
Wherein formaldehyde consumption 40% (with respect to over dry lignin), sodium sulfite consumption is 30% (with respect to over dry lignin).
The sulfonation modifying technique of control group 2 is as follows：Taking alkali lignin that the alkaline sulfurous method black liquor of pulp making of Eucalyptus extracts, (purity is
80%, particle diameter is 90 mesh, and water content is 1%), to be added in deionized water, and the consumption of water is the 300% of lignin quality, magnetic force
Stir (300r/min, 20min), be heated to 95 DEG C, add 10% sodium hydroxide and be used as oxidant (with respect to over dry lignin), constant temperature
10-15min.Hydrogen peroxide is added, hydrogen peroxide use is 1% (with respect to over dry lignin), controls 95 DEG C of temperature, reacts 1 hour,
Formaldehyde and sodium sulfite are subsequently added, keeps reacting 3h, wherein formaldehyde consumption 40% (with respect to over dry lignin), sulfurous acid at 95 DEG C
Sodium consumption is 30% (with respect to over dry lignin).
The contrast table of the different pretreatments method lignosulfonate efficiency of table 5
| Sample | Sulfonation degree (mmol/g) | Solubility (%) (pH=7,25 DEG C) in water |
| Embodiment 2 | 1.57 | 90.4 |
| Control group 2 | 1.45 | 88.1 |
The data of table 5 can be seen that compares highly basic using the pretreated alkali lignin sulfonation degree of 1- ethyl-3-methylimidazole villaumites
Alkali lignin after oxidation processes improves 8.3%, and the solubility in water improves 2.6%, the raising of sulfonation degree and solubility, surface
The sulfonation efficiency of Eucalyptus alkali lignin can be significantly improved by the pretreatment of 1- ethyl-3-methylimidazoles villaumite.
Embodiment 6
Taking commercialization alkali lignin, (purity is 95%, and particle diameter is 100 mesh, and water content is 3%), to add 1- ethyl -3- methyl
The mixing pretreatment of imidazoles villaumite, adds deionized water terminating reaction, is then centrifuged (rotating speed 3500r/ after the completion of processing
Min), freeze-drying obtains pretreated alkali lignin.Carry out vacuum distillation and reclaim 1- ethyl-3-methylimidazole villaumites.Processing
Condition is：The consumption of 1- ethyl -3- methyl miaow villaumites is the 500% of over dry alkali lignin quality, and treatment temperature is 90 DEG C, during processing
Between be 120min.The sulfonation modifying technique of lignin is as follows：Pretreated alkali lignin sample is added in deionized water, the use of water
Measure as the 300% of lignin quality, magnetic agitation (300r/min, 20min), be heated to 95 DEG C, add hydrogen peroxide, control temperature
95 DEG C, react 1 hour, be subsequently added formaldehyde and sodium sulfite, keep reacting 3h at 95 DEG C, wherein formaldehyde consumption 40% is (relative
Over dry lignin), sodium sulfite consumption is 30% (with respect to over dry lignin).
The sulfonation modifying technique of control group 6 is as follows：Being commercialized alkali lignin, (purity is 95%, and particle diameter is 100 mesh, and water content is
3%) it is added in deionized water, the consumption of water is the 300% of lignin quality, magnetic agitation (300r/min, 20min), heating
To 95 DEG C, add 10% sodium hydroxide and be used as oxidant (with respect to over dry lignin), constant temperature 10-15min.Add hydrogen peroxide, mistake
Hydrogen oxide consumption is 1% (with respect to over dry lignin), controls 95 DEG C of temperature, reacts 1 hour, is subsequently added formaldehyde and sodium sulfite,
Keep reacting 3h, wherein formaldehyde consumption 40% (with respect to over dry lignin) at 95 DEG C, sodium sulfite consumption is 30% (with respect to over dry wood
Element).
The contrast table of the different pretreatments method lignosulfonate efficiency of table 6
| Sample | Sulfonation degree (mmol/g) | Solubility (%) (pH=7,25 DEG C) in water |
| Embodiment 6 | 1.65 | 95.4 |
| Control group 6 | 1.52 | 90.8 |
The data of table 6 can be seen that using the pretreated alkali lignin sulfonation degree of 1- ethyl -3- methyl miaow villaumites than highly basic oxygen
Alkali lignin after change processing improves 8.5%, the solubility raising 5.1% in water, the raising of sulfonation degree and solubility, and surface is borrowed
The pretreatment of 1- ethyl-3-methylimidazoles villaumite is helped to significantly improve the sulfonation efficiency of commercialization alkali lignin.
Above-described embodiment is preferably embodiment, but embodiments of the present invention are not by above-described embodiment of the invention
Limitation, other any Spirit Essences without departing from the present invention and the change made under principle, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (10)
1. it is a kind of improve alkali lignin sulfonation yield method, it is characterised in that this method by alkali lignin is pre-processed with
Alkali lignin sulfonation yield is improved, the pretreatment specifically includes following steps：Alkali lignin is added into 1- ethyl-3-methylimidazole vinegar
Hydrochlorate or 1- ethyl-3-methylimidazoles villaumite, which are well mixed, to be handled, and water terminating reaction is added after the completion of processing, is then carried out
Centrifugation and freeze-drying obtain pretreated alkali lignin.
2. a kind of method for improving alkali lignin sulfonation yield according to claim 1, it is characterised in that：Described alkali lignin
Pass through including needlebush, leaf wood or grass as raw material in all kinds of soda pulping process nights and extract obtained alkali lignin, also including business
Change all kinds of alkali lignins sold.
3. a kind of method for improving alkali lignin sulfonation yield according to claim 1, it is characterised in that：The alkali lignin is pure
Spend for 80~95%.
4. a kind of method for improving alkali lignin sulfonation yield according to claim 1, it is characterised in that：The alkali lignin contains
Water is 1~3%.
5. a kind of method for improving alkali lignin sulfonation yield according to claim 1, it is characterised in that：The alkali lignin grain
Footpath is 80~100 mesh.
6. a kind of method for improving alkali lignin sulfonation yield according to claim 1, it is characterised in that：Described 1- second
The purity of base -3- methylimidazoles acetate or 1- ethyl-3-methylimidazole villaumites is 95~99%.
7. a kind of method for improving alkali lignin sulfonation yield according to claim 1, it is characterised in that：The 1- ethyls-
The consumption of 3- methylimidazoles acetate or 1- ethyl-3-methylimidazole villaumites is the 400%-500% of over dry alkali lignin quality.
8. a kind of method for improving alkali lignin sulfonation yield according to claim 1, it is characterised in that：The treatment temperature
For 80~90 DEG C.
9. a kind of method for improving alkali lignin sulfonation yield according to claim 1, it is characterised in that：The processing time
For 60~120min.
10. a kind of method for improving alkali lignin sulfonation yield according to claim 1, it is characterised in that：The centrifugation
Rotating speed is 3000~3500r/min.
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