CN103949216A - Preparation method of carbon material for adsorbing hydrophilic ionic liquid - Google Patents
Preparation method of carbon material for adsorbing hydrophilic ionic liquid Download PDFInfo
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000003575 carbonaceous material Substances 0.000 title claims abstract description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 34
- 238000001179 sorption measurement Methods 0.000 claims abstract description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 239000011148 porous material Substances 0.000 claims abstract description 9
- 238000003763 carbonization Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 7
- 230000004913 activation Effects 0.000 claims abstract description 6
- 229920002678 cellulose Polymers 0.000 claims abstract description 6
- 239000001913 cellulose Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 239000004005 microsphere Substances 0.000 claims abstract 4
- 239000000463 material Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000012153 distilled water Substances 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- -1 polytetrafluoroethylene Polymers 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 5
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 5
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 5
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 229910001220 stainless steel Inorganic materials 0.000 claims description 5
- 239000010935 stainless steel Substances 0.000 claims description 5
- 235000010980 cellulose Nutrition 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 3
- 238000004438 BET method Methods 0.000 claims 1
- 238000000921 elemental analysis Methods 0.000 claims 1
- 238000003760 magnetic stirring Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 238000004626 scanning electron microscopy Methods 0.000 claims 1
- 239000003463 adsorbent Substances 0.000 abstract description 22
- 230000000694 effects Effects 0.000 abstract description 4
- 239000002351 wastewater Substances 0.000 abstract description 3
- 125000003636 chemical group Chemical group 0.000 abstract 1
- 238000001027 hydrothermal synthesis Methods 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 description 8
- 238000013019 agitation Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 238000002389 environmental scanning electron microscopy Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RLLPVAHGXHCWKJ-IEBWSBKVSA-N (3-phenoxyphenyl)methyl (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-IEBWSBKVSA-N 0.000 description 1
- LVHMJHXXLZIOOJ-UHFFFAOYSA-N C(CCC)N1CN(C=C1)C.[Br] Chemical compound C(CCC)N1CN(C=C1)C.[Br] LVHMJHXXLZIOOJ-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000252212 Danio rerio Species 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 238000005255 carburizing Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 241001233061 earthworms Species 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003891 environmental analysis Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Carbon And Carbon Compounds (AREA)
Abstract
本发明提供了一种吸附亲水性离子液体的碳材料的制备方法，是以纤维素为原材料，先在高压水热反应釜中进行水热反应，得到富含羟基、羧基等含氧基团的碳微球，该碳微球再在马弗炉中在氮气氛围保护下用KOH进行活化，得到比表面积大且表面富含氧基团的海绵状碳材料。纤维素的不完全水热碳化可以得到表面富含含氧基团的碳微球，而KOH活化可以在保留表面含氧化学基团的情况下，大大提高碳材料的比表面积，改善其孔道结构，最终得到对亲水性离子液体具有独特吸附性能的碳材料吸附剂，其吸附效率和吸附容量大大提高。本发明所需原材料常见易得，制备方法简单，得到的碳材料吸附剂对于废水中亲水性离子液体的吸附、回收与循环利用具有良好效果。
The invention provides a method for preparing a carbon material that absorbs hydrophilic ionic liquids. Using cellulose as a raw material, the hydrothermal reaction is first carried out in a high-pressure hydrothermal reactor to obtain oxygen-containing groups rich in hydroxyl groups and carboxyl groups. The carbon microspheres were activated with KOH in a muffle furnace under the protection of a nitrogen atmosphere to obtain a sponge-like carbon material with a large specific surface area and rich oxygen groups on the surface. The incomplete hydrothermal carbonization of cellulose can obtain carbon microspheres rich in oxygen-containing groups on the surface, while KOH activation can greatly increase the specific surface area of carbon materials and improve their pore structure while retaining the oxygen-containing chemical groups on the surface. , and finally a carbon material adsorbent with unique adsorption properties for hydrophilic ionic liquids is obtained, and its adsorption efficiency and adsorption capacity are greatly improved. The raw materials required by the invention are common and easy to obtain, the preparation method is simple, and the obtained carbon material adsorbent has good effects on the adsorption, recovery and recycling of hydrophilic ionic liquids in waste water.
Description
Technical field
The invention belongs to preparation and environment and the Application in Chemical Engineering field of living beings class adsorbent, specifically, the incomplete hydrothermal carbonization and the KOH thereof that relate to by cellulose biomass activate, thereby obtain high-specific surface area and pore volume while rich surface containing the method for the material with carbon element adsorbent containing oxygen functional group.
Background technology
When referring at normal temperature or approach normal temperature, ionic liquid in liquid salt, conventionally by organic cation and inorganic anion, formed.Because ionic liquid has good heat endurance and the vapour pressure that can't detect, thereby be considered to a kind of green solvent all the time and be widely used in the fields such as material preparation, energy storage, living beings utilization, chemical industry, catalysis and environmental analysis.But nearest result of study shows that ionic liquid exists certain toxicity to biologies such as flea, algae, zebra fish, earthworms, thereby environment and the ecosystem are existed to certain potential risk.Due to the stability of ionic liquid, be difficult to decompose by chemical method, be also difficult to be degraded by microorganisms, therefore absorption is to a kind of effective ways of ionic liquid being separated from waste water before environment at ionic liquid discharge of wastewater.
Active carbon is the conventional adsorbent of adion liquid at present, although but traditional method for preparation of active carbon makes it have huge specific area, but the oxy radical on surface seldom, its surface is hydrophobic, thereby traditional active carbon only has good adsorption effect to hydrophobic ionic liquid, and not good to hydrophilic ionic liquid adsorption effect.Therefore, for using the processing of hydrophilic ionic-liquid more widely, need to develop the preparation method of new adsorbent, prepared adsorbent is except having huge specific area and pore volume, and abundant polar group also should be contained in its surface.
In the present invention, we utilize cellulosic incomplete hydrothermal carbonization, obtain being rich in the carbosphere of the function group such as hydroxyl and carboxyl.The oxygen content of this carbosphere is very high, but due to the very low (220-280 of carburizing temperature
oc), thus specific area very little.This carbosphere is further activated with KOH under nitrogen atmosphere, obtained having the material with carbon element adsorbent of large specific area and oxy radical simultaneously.Compare with traditional active carbon, this adsorbent improves greatly to the adsorption capacity of hydrophilic ionic-liquid.
Successively utilize the method preparation of this cellulosic hydrothermal carbonization and KOH activation to there is the method for the carbon adsorbent of larger specific area and high polarity oxy radical simultaneously, and the absorption for polar by it, there is not yet before this report.
Summary of the invention
The present invention is directed to the problem that traditional active carbon is little to hydrophilic ionic-liquid adsorption capacity, adsorption efficiency is low, a kind of method of preparing novel cellulose base material with carbon element adsorbent is provided, this adsorbent is high to hydrophilic ionic-liquid adsorption efficiency, adsorption capacity is large, and can recycle.
The preparation method of the material with carbon element of the absorption hydrophilic ionic-liquid that the present invention proposes, is to take fiber rope as raw material, utilizes successively cellulosic incomplete hydrothermal carbonization and KOH activation to obtain the spongy material with carbon element adsorbent of black.This material specific area is 900 ~ 1500 m
2/ g, pore volume is at 0.4 ~ 0.9 cm
3/ g, carbon content is 55 ~ 75%, and oxygen content is 20 ~ 40%, the functional groups such as rich surface hydroxyl, carboxyl.Specifically comprise the following steps:
(1) under magnetic agitation, successively add the microcrystalline cellulose of 1 ~ 4 mass parts and the distilled water of 10 mass parts, continue to stir 30min;
(2) mixed liquor of step (1) preparation is proceeded in the stainless steel autoclave of inner liner polytetrafluoroethylene to heated sealed to 220 ~ 280
oc constant temperature 6 ~ 12h, 1000 revs/min of rotating speeds stir;
(3) reaction is cooled to room temperature after finishing, and distilled water and alternately washing of ethanol for the black powder of generation, remove whole moisture in 80 ℃ of freeze-day with constant temperature 12h, obtains particle diameter at the carbosphere of 3 ~ 5 microns;
(4) after the carbosphere material obtaining in step (3) and KOH powder are mixed with the mass ratio of 1:1 to 1:4, put into Muffle furnace, pass into nitrogen, under nitrogen atmosphere 600
ounder C, heat treatment is 1 ~ 6 hour;
(5) solid obtaining in step (4) alternately cleans to pH and is neutral with the HCl solution of 0.1 ~ 1 mol/L and distilled water, in 80 ℃ of freeze-day with constant temperature 12h, obtains being the material with carbon element of the absorption hydrophilic ionic-liquid of black;
(6) this material with carbon element proves that after SEM, FT-IR and elementary analysis it is the spongy carbon material that contain-OH of rich surface ,-COOH, C=O etc. contain oxygen functional group.
[advantage of the present invention and good effect]:
The present invention has following advantages: the one, and the raw material sources of absorbent preparation are the biomass celluloses that nature extensively exists, they are reproducible, wide material sources; The 2nd, the hydrothermal carbonization adopting in absorbent preparation process and follow-up activation temperature are relatively low; Easy operating and the saving energy; The 3rd, the adsorbent preparing not only has huge specific area and pore volume, and rich surface contains oxygen functional group containing polarity, it has better absorption property to hydrophilic ionic-liquid, adsorbance to typicalness hydrophilic ionic-liquid 1-butyl-3-methylimidazole bromine salt reaches 102.9 mg/g, is 4 times of common active carbon.In addition, adsorption and enrichment is easy to reclaim by pickling desorption to the ionic liquid on adsorbent, and sorbent circulation is used.
[accompanying drawing explanation]:
Fig. 1 is ESEM (SEM) figure of the carbosphere that obtains of cellulosic incomplete hydrothermal carbonization, and Fig. 2 is that hydro-thermal carbosphere is further with ESEM (SEM) figure of the spongy material with carbon element adsorbent obtaining after KOH activation.
[specific embodiment]:
embodiment 1:
(1) under magnetic agitation, successively add the microcrystalline cellulose of 20 g and the distilled water of 60 mL, continue to stir 30min;
(2) mixed liquor of step (1) preparation is proceeded in the stainless steel autoclave of inner liner polytetrafluoroethylene to heated sealed to 250
oc constant temperature 10 h, 1000 revs/min of rotating speeds stir;
(3) reaction is cooled to room temperature after finishing, and distilled water and alternately washing of ethanol for the black powder of generation, remove whole moisture in 80 ℃ of freeze-day with constant temperature 12h, obtains particle diameter at the carbosphere of 3 ~ 5 microns;
(4) after the carbosphere material obtaining in step (3) and KOH powder are mixed with the mass ratio of 1:4, put into Muffle furnace, pass into nitrogen, under nitrogen atmosphere 600
ounder C, heat treatment is 2 hours;
(5) solid obtaining in step (4) alternately cleans to pH and is neutral with the HCl solution of 1 mol/L and distilled water, in 80 ℃ of freeze-day with constant temperature 12h, obtains being the material with carbon element of the absorption hydrophilic ionic-liquid of black;
(6) this material with carbon element proves that after SEM, FT-IR and elementary analysis it is the spongy carbon material that contain-OH of rich surface ,-COOH, C=O etc. contain oxygen functional group.This material specific area is 1240 m
2/ g, pore volume is at 0.655 cm3/g, carbon content 61%, oxygen content is 36%.
(7) test shows, this material with carbon element adsorbent prepared by the present embodiment, 25
o1-butyl-3-methylimidazole bromine salt ion the liquid aqueous solution (pH 8.0) that is 50 mg/L to 20 mL concentration under C carries out Static Adsorption, and this adsorbent of 0.05 g reaches 98% at 30 min with the interior clearance to 1-butyl-3-methylimidazole bromine salt ion liquid.Adsorption isotherm result of the test shows that its maximal absorptive capacity reaches 65.7 mg/g.
embodiment 2:
(1) under magnetic agitation, successively add the microcrystalline cellulose of 10 g and the distilled water of 60 mL, continue to stir 30min;
(2) mixed liquor of step (1) preparation is proceeded in the stainless steel autoclave of inner liner polytetrafluoroethylene to heated sealed to 260
oc constant temperature 8 h, 1000 revs/min of rotating speeds stir;
(3) reaction is cooled to room temperature after finishing, and distilled water and alternately washing of ethanol for the black powder of generation, remove whole moisture in 80 ℃ of freeze-day with constant temperature 12h, obtains particle diameter at the carbosphere of 3 ~ 5 microns;
(4) after the carbosphere material obtaining in step (3) and KOH powder are mixed with the mass ratio of 1:2, put into Muffle furnace, pass into nitrogen, under nitrogen atmosphere 600
ounder C, heat treatment is 4 hours;
(5) solid obtaining in step (4) alternately cleans to pH and is neutral with the HCl solution of 1 mol/L and distilled water, in 80 ℃ of freeze-day with constant temperature 12h, obtains being the material with carbon element of the absorption hydrophilic ionic-liquid of black;
(6) this material with carbon element proves that after SEM, FT-IR and elementary analysis it is the spongy carbon material that contain-OH of rich surface ,-COOH, C=O etc. contain oxygen functional group.This material specific area is 1040 m
2/ g, pore volume is at 0.565 cm3/g, carbon content 65%, oxygen content is 30%;
(7) test shows, this material with carbon element adsorbent prepared by the present embodiment, 25
o1-butyl-3-methylimidazole bromine salt ion the liquid aqueous solution (pH 8.0) that is 50 mg/L to 20 mL concentration under C carries out Static Adsorption, and this adsorbent of 0.05 g reaches 96% at 30 min with the interior clearance to 1-butyl-3-methylimidazole bromine salt ion liquid.Adsorption isotherm result of the test shows that its maximal absorptive capacity reaches 61.3 mg/g.
embodiment 3:
(1) under magnetic agitation, successively add the microcrystalline cellulose of 20 g and the distilled water of 50 mL, continue to stir 30min;
(2) mixed liquor of step (1) preparation is proceeded in the stainless steel autoclave of inner liner polytetrafluoroethylene to heated sealed to 250
oc constant temperature 12 h, 1000 revs/min of rotating speeds stir;
(3) reaction is cooled to room temperature after finishing, and distilled water and alternately washing of ethanol for the black powder of generation, remove whole moisture in 80 ℃ of freeze-day with constant temperature 12h, obtains particle diameter at the carbosphere of 3 ~ 5 microns;
(4) after the carbosphere material obtaining in step (3) and KOH powder are mixed with the mass ratio of 1:4, put into Muffle furnace, pass into nitrogen, under nitrogen atmosphere 600
ounder C, heat treatment is 2 hours;
(5) solid obtaining in step (4) alternately cleans to pH and is neutral with the HCl solution of 1 mol/L and distilled water, in 80 ℃ of freeze-day with constant temperature 12h, obtains being the material with carbon element of the absorption hydrophilic ionic-liquid of black;
(6) this material with carbon element proves that after SEM, FT-IR and elementary analysis it is the spongy carbon material that contain-OH of rich surface ,-COOH, C=O etc. contain oxygen functional group.This material specific area is 1360 m
2/ g, pore volume is at 0.712 cm3/g, carbon content 59%, oxygen content is 36%;
(7) test shows, this material with carbon element adsorbent prepared by the present embodiment, 25
o1-butyl-3-methylimidazole bromine salt ion the liquid aqueous solution (pH 11.0) that is 50 mg/L to 20 mL concentration under C carries out Static Adsorption, and this adsorbent of 0.05 g reaches 99.5% at 30 min with the interior clearance to 1-butyl-3-methylimidazole bromine salt ion liquid.Adsorption isotherm result of the test shows that its maximal absorptive capacity reaches 102.9 mg/g.
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Cited By (13)
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| EP2982649A1 (en) * | 2014-08-08 | 2016-02-10 | AVA-Co2 Schweiz AG | Method for the production of high quality activated carbons and activated carbons produced using the method |
| CN105597706A (en) * | 2015-12-23 | 2016-05-25 | 北京化工大学 | Preparation method for porous polymeric ionic liquid for carbon dioxide adsorption |
| CN105664847A (en) * | 2016-01-13 | 2016-06-15 | 南昌航空大学 | Method for preparing high-specific surface area porous carbon material based on oil tea seed husk and application thereof |
| CN105883805A (en) * | 2016-04-20 | 2016-08-24 | 南昌航空大学 | Preparation method of camellia seed shell based carbon microspheres with high specific surface area |
| CN106345412A (en) * | 2016-10-20 | 2017-01-25 | 南京大学 | Method for removing 1-butyl-3-methylimidazol ionic liquid pollutants out of water through adsorption method |
| US9914679B2 (en) | 2014-12-12 | 2018-03-13 | Uop Llc | Processes for removing entrained ionic liquid from a hydrocarbon phase |
| CN111011161A (en) * | 2019-12-26 | 2020-04-17 | 郑州大学 | A kind of red mud soil matrix and preparation method thereof |
| CN112645307A (en) * | 2021-01-28 | 2021-04-13 | 太原理工大学 | Method for preparing hydrophilic carbon material |
| CN112973628A (en) * | 2021-02-06 | 2021-06-18 | 重庆文理学院 | Preparation method of activated carbon rich in basic functional groups |
| CN113247985A (en) * | 2021-07-09 | 2021-08-13 | 生态环境部华南环境科学研究所 | TBBPA-containing sewage treatment method, porous carbon microsphere material and preparation method |
| CN114749211A (en) * | 2022-05-18 | 2022-07-15 | 农业农村部环境保护科研监测所 | A kind of sulfonic acid carbon microsphere and its preparation method and application |
| CN115318257A (en) * | 2022-05-25 | 2022-11-11 | 贵州大学 | Preparation method of sauce-flavor wine vinasse-based porous carbon composite ionic liquid gas adsorbent |
| CN118164724A (en) * | 2024-03-18 | 2024-06-11 | 昆明理工大学 | A cement-modified activated carbon composite cementitious material, preparation method thereof and concrete |
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Cited By (17)
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|---|---|---|---|---|
| EP2982649A1 (en) * | 2014-08-08 | 2016-02-10 | AVA-Co2 Schweiz AG | Method for the production of high quality activated carbons and activated carbons produced using the method |
| US9914679B2 (en) | 2014-12-12 | 2018-03-13 | Uop Llc | Processes for removing entrained ionic liquid from a hydrocarbon phase |
| CN105597706A (en) * | 2015-12-23 | 2016-05-25 | 北京化工大学 | Preparation method for porous polymeric ionic liquid for carbon dioxide adsorption |
| CN105597706B (en) * | 2015-12-23 | 2017-12-12 | 北京化工大学 | A kind of preparation method of porous polymeric ionic liquid for carbon dioxide adsorption |
| CN105664847B (en) * | 2016-01-13 | 2018-08-17 | 南昌航空大学 | A kind of preparation and application of the porous carbon materials of the high-specific surface area based on tea seed shell base |
| CN105664847A (en) * | 2016-01-13 | 2016-06-15 | 南昌航空大学 | Method for preparing high-specific surface area porous carbon material based on oil tea seed husk and application thereof |
| CN105883805A (en) * | 2016-04-20 | 2016-08-24 | 南昌航空大学 | Preparation method of camellia seed shell based carbon microspheres with high specific surface area |
| CN105883805B (en) * | 2016-04-20 | 2018-01-12 | 南昌航空大学 | A kind of preparation method of the high-specific surface area carbosphere based on tea seed shell base |
| CN106345412A (en) * | 2016-10-20 | 2017-01-25 | 南京大学 | Method for removing 1-butyl-3-methylimidazol ionic liquid pollutants out of water through adsorption method |
| CN111011161A (en) * | 2019-12-26 | 2020-04-17 | 郑州大学 | A kind of red mud soil matrix and preparation method thereof |
| CN112645307A (en) * | 2021-01-28 | 2021-04-13 | 太原理工大学 | Method for preparing hydrophilic carbon material |
| CN112973628A (en) * | 2021-02-06 | 2021-06-18 | 重庆文理学院 | Preparation method of activated carbon rich in basic functional groups |
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Application publication date: 20140730 |