| 511 | 1 | 101 |
| 下载次数 | 被引频次 | 阅读次数 |
环糊精是直链淀粉在酶作用下水解生成的无毒、天然、廉价的环状低聚糖，其疏水空腔可以通过主客体作用包覆污染物中的疏水分子，尤其是芳香类分子，从而提高其吸附效率和吸附选择性。采用环糊精直接和交联剂反应或者采用环糊精对吸附剂进行修饰，可以得到含有环糊精的吸附剂。含有环糊精的吸附剂在吸附分离等领域有广阔的应用前景。文章综述了近年来环糊精在吸附分离材料方面的研究进展，总结了含环糊精吸附剂的不同合成方法；并针对含环糊精吸附剂对有机分子、重金属离子及有机染料等污染物的吸附特点进行分类和探讨；最后对含环糊精吸附剂的未来发展方向进行展望，旨在引起研究者对含有环糊精吸附剂的研究兴趣，并为其提供一些新的启发和思路。
Abstract：Cyclodextrins(CDs) are derived from the enzymatic hydrolysis of starch, CDs are nontoxic, natural and inexpensive torus-shaped cyclic oligosaccharides. The interior cavity of the CD molecule is hydrophobic,which could trap aromatic contaminants through the host-guest and hydrophobic interaction to improve the adsorption efficiency and selectivity. Adsorbents containing cyclodextrins can be synthesized by the direct reaction of cyclodextrin and crosslinker or by the modification of the adsorbents using cyclodextrin. Adsorbents containing cyclodextrins have important applications in the fields of adsorption and separation. This review focuses on the research progress of adsorbents containing cyclodextrins in recent years. Different methods of the synthesis of adsorbents containing cyclodextrins are also summarized, and the adsorption characteristics of adsorbents containing cyclodextrins for organic molecules, heavy metal ions and organic dyes are classified and discussed too. Finally, the outlook on the future development of adsorbents containing cyclodextrins is presented.We hope that, this paper can arouse the interest of researchers to the study of adsorbents containing cyclodextrins,and provide some inspiration and new ideas for readers.
1 Verma M,Lee I,Oh J,Kumar V,Kim H.Synthesis of EDTA-functionalized graphene oxide-chitosan nanocomposite for simultaneous removal of inorganic and organic pollutants from complex wastewater[J].Chemosphere,2022,287:132385.
2 Liu Y H,Chen Y N,Li Y P,Chen L,Jiang H J,Li H,Luo X L,Tang P,Yan H Q,Zhao M Y,Yuan Y,Hou S Z.Fabrication,application,and mechanism of metal and heteroatom co-doped biochar composites(MHBCs) for the removal of contaminants in water:A review[J].Journal of Hazardous Materials,2022,431:128584.
3 Mahmuda A,Tajuddin S,Ullah A K M A.Water quality assessment of an industrial zone polluted aquatic body in Dhaka,Bangladesh[J].American Journal of Environmental Protection,2014,3(5):232-237.
4 Li X Z,Yang Y,Xu X,Xu C Q,Hong J L.Air pollution from polycyclic aromatic hydrocarbons generated by human activities and their health effects in China[J].Journal of Cleaner Production,2016,112:1360-1367.
5 Ben W W,Zhu B,Yuan X J,Zhang Y,Yang M,Qiang Z M.Occurrence,removal and risk of organic micropollutants in wastewater treatment plants across China:comparison of wastewater treatment processes[J].Water Research,2018,130:38-46.
6 Bansod B K,Tejinder K,Ritula T,Shakshi R,Inderbir S.A review on various electrochemical techniques for heavy metal ions detection with different sensing platforms[J].Biosensors and Bioelectronic,2017,94:443-455.
7 Puga A,Moreira M M,Pazos M.Continuous adsorption studies of pharmaceuticals in multicomponent mixtures by agroforestry biochar[J].Journal of Environmental Chemical Engineering,2022,10:106977.
8 Shahid M K,Kashif A,Fuwad A,Choi Y.Current advances in treatment technologies for removal of emerging contaminants from water:a critical review[J].Coordination Chemistry Reviews,2021,442:213993.
9 Liu M Y,Zhang X T,Han R P,Qu L B.Crosslinked polyethylenimine/polyacrylonitrile blend membrane for multifunctional adsorption of heavy metals and endocrine disrupting chemicals in solution[J].Journal of Molecular Liquids,2022,365:120124.
10 Zhou Y B,Cheng G,Chen K,Lu J,Lei J Y,Pu S Y.Adsorptive removal of bisphenol A,chloroxylenol,and carbamazepine from water using a novel β-cyclodextrin polymer[J].Ecotoxicology and Environmental Safety,2019,170:278-285.
11 Fu F L,Wang Q.Removal of heavy metal ions from wastewaters:a review[J].Journal of Environmental Management,2011,92:407-418.
12 Hashim M A,Soumyadeep M,Sahu J N,Sengupta B.Remediation technologies for heavy metal contaminated groundwater[J].Journal of Environmental Management,2011,92:2355-2388.
13 Zagklis D P,Vavouraki A I,Kornaros M E,Paraskeva C A.Purification of olive mill wastewater phenols through membrane filtration and resin adsorption/desorption[J].Journal of Hazardous Materials,2015,285:69-76.
14 Xiao J D,Xie Y B,Cao H B.Organic pollutants removal in wastewater by heterogeneous photocatalytic ozonation[J].Chemosphere,2014,121:1-17.
15 Zhao L,Ji Y F,Kong D Y,Lu J H,Zhou Q S,Yin X M.Simultaneous removal of bisphenol A and phosphate in zero-valent iron activated persulfate oxidation process[J].Chemical Engineering Journal,2016,303:458-466.
16 M.Kamaraj,P.Suresh Babu,S.Shyamalagowri,M.K.S.Pavithra,J.Aravind,Woong Kim,M.Govarthanan.β-cyclodextrin polymer composites for the removal of pharmaceutical substances,endocrine disruptor chemicals,and dyes from aqueous solution-a review of recent trends[J].Journal of Environmental Management,2024,351:119830.
17 Sone B,Makamu E,Mohamed H E A,Oputu O,Fester V.Green-synthesized Zn O via Hyphaene thebaica fruit extracts:structure&catalytic effect on the ozonation of Coralene Rubine-S2G azo disperse dye[J].Environmental Nanotechnology,Monitoring&Management,2021,16:100515.
18 Muniyasamy A,Sivaporul G,Gopinath A,Lakshmanan R,Chellam P V.Process development for the degradation of textile azo dyes(mono-,di-,poly-) by advanced oxidation process-ozonation:Experimental&partial derivative modelling approach[J].Journal of Environmental Management,2020,265:110397.
19 Qu J H,Tian X,Zhang X B.Free radicals-triggered reductive and oxidative degradation of highly chlorinated compounds via regulation of heat-activated persulfate by low-molecular-weight organic acids[J].Applied Catalysis B:Environmental,2022,310:121359.
20 Santos D H S,Duarte J L S,Tavares M,Tavares M G.Electrochemical degradation and toxicity evaluation of reactive dyes mixture and real textile effluent over DSA?electrodes[J].Chemical Engineering Processing-Process Intensification,2020,153:107940.
21 Hamous H,Khenifi A,Orts F,Bonastre J,Cases F.Carbon textiles electrodes modified with RGO and Pt nanoparticles used for electrochemical treatment of azo dye[J].Journal of Electroanalytical Chemistry,2021,887:115154.
22 Wang W Y,Wu G Y,Zhu T,Yang Y,Zhang Y Y.Synthesis of-thiazole Schiff base modified SBA-15 mesoporous silica for selective Pb(II) adsorption[J].Journal of the Taiwan Institute of Chemical Engineers,2021,125:349-359.
23 Crini G,Morcellet M.Synthesis and applications of adsorbents containing cyclodextrins[J].Journal of Separation Science,2002,25:789-813.
24 Mohamed M H,Wilson L D,Pratt D Y,Guo R,Wu C,Headley J V.Evaluation of the accessible inclusion sites in copolymer materials containing beta-cyclodextrin[J].Carbohydrate Polymer,2012,87:1241-1248.
25 Ya?ez C,Araya M,Bollo S.Complexation of herbicide bentazon with native and modified β-cyclodextrin[J].Journal of Inclusion Phenomena and Macrocyclic Chemistry,2010,68:237-241.
26 Prabaharan M,Gong S Q.Novel thiolated carboxymethyl chitosan-g-β-cyclodextrin as mucoadhesive hydrophobic drug delivery carriers[J].Carbohydrate Polymers,2008,73(1):117-125.
27 Yilmaz E,Memon S,Yilmaz M.Removal of direct azo dyes and aromatic amines from aqueous solutions using two β-cyclodextrin-based polymers[J].Journal of Hazardous Materials,2010,174(1):592-597.
28 Nafie G,Vitale G,Ortega C,Antonio L,Nashaat N N.Nanopyroxene grafting with β-cyclodextrin monomer for wastewater applications[J].Material Interfaces,2017,9:42393-42407.
29 Tang P X,Sun Q M,Zhao L D,Tang Y L,Liu Y Q,Pu H Y,Gan N,Liu Y Y,Li H.A simple and green method to construct cyclodextrin polymer for the effective and simultaneous estrogen pollutant and metal removal[J].Chemical Engineering Journal,2019,366:598-607.
30 Cui Y Y,Bi Y P,Yang C X.Solvent regulation and template-free synthesis of β-cyclodextrin-based microporous organic network nanosheets for ultrafast and efficient removal of aromatic pollutants[J].Chemical Engineering Journal,2022,435:134829.
31 Ma J T,Zhang Y,Zhao B F,Jia Q.Supramolecular adsorbents in extraction and separation techniques:a review[J].Analytica Chimica Acta,2020,1122:97-113.
32 Li H Y,Meng B,Chai S H,Liu H L,Dai S.Hyper-crosslinked β-cyclodextrin porous polymer:an adsorptionfacilitated molecular catalyst support for transformation of water-soluble aromatic molecules[J].Chemical Science,2016,7(2):905-909.
33 Alsbaiee A,Smith B J,Xiao L L.Rapid removal of organic micropollutants from water by a porous β-cyclodextrin polymer[J].Nature,2015,529(7585):190-194.
34 Zhou Y B,Gu X C,Zhang R Z,Lu J.Influences of various cyclodextrins on the photodegradation of phenol and bisphenol A under UV light[J].Industrial&Engineering Chemistry Research,2015,54(1):426-433.
35 Shen H M,Zhu G Y,Yu W B.Fast adsorption of p-nitrophenol from aqueous solution using beta-cyclodextrin grafted silica gel[J].Applied Surface Science,2015,356:1155-1167.
36 Liu J,Yang Y M,Bai J W,Wen H,Chen F J,Wang B D.Hyper-cross-linked porous Mo S2-cyclodextrin-polymer frameworks:durable removal of aromatic phenolic micropollutant from water[J].Analytical Chemistry,2018,90:3621-3627.
37 Liu H H,Cai X Y,Wang Y.Adsorption mechanism-based screening of cyclodextrin polymers for adsorption and separation of pesticides from water[J].Water Research,2011,45(11):3499-3511.
38 Sikder T,Rahman M,Jakariya,Hosokawa T,Kurasaki M,Saito T.Remediation of water pollution with native cyclodextrins and modified cyclodextrins:a comparative overview and perspectives[J].Chemical Engineering Journal,2019,355:920-941.
39童林荟.环糊精化学基础与应用[M].北京:科学出版社,2001.
40刘育,厉斌,张毅民,卜显和,李玉梅,陈荣悌.超分子体系中的分子识别研究Ⅲ-环糊精双核铜配合物对芳香氨基酸的手性识别[J].科学通报,1995,40(20):1858-1861.
41 Chen I,Chen M,Xu C Y,Yam K L.Critical review of controlled release packaging to improve food safety and quality[J].Critical Reviews in Food Science and Nutrition,2019,59:2386-2399.
42王佳玉,齐德胜,吴自华,于双江,魏舒.β-环糊精基多孔聚合物用于水溶性有机小分子的吸附研究[J].长春理工大学学报(自然科学版),2020,43(4):129-135.
43 Tu Y Z,Xu G Z,Lu J,Hu X J,Xu J,Xie X C,Li A M.Amphiphilic hyper-crosslinked porous cyclodextrin polymer with high specific surface area for rapid removal of organic micro pollutants[J].Chemical Engineering Journal,2020,382:123015.
44 Nozaki T,Maeda Y,Kitano H.Cyclodextrin gels which have a temperature responsiveness[J].Polymer Chemistry,1997,35(8):1535-1541.
45 Takayuki H,Masaya K,Hiroyuki A,Makoto K,Masahiko S.Molecularly imprinted cyclodextrins as selective receptors for steroids[J].Macromolecules,1999,32(7):2265-2269.
46赵晓斌,何炳林.环糊精高聚物研究与开发应用进展[J].离子交换与吸附,1994,10(5):472-478.
47 Xu G Z,Xie X C,Qin L,Hu X J,Zhang D L,Xu J,Li D W,Ji X W,Huang Y,Tu Y Z,Jiang L,Wei D Y.Simple synthesis of a swellable porous β-cyclodextrin-based polymer for rapid removal of organic micro-pollutants from water[J].Green Chemistry,2019,21(22):6062-6072.
48 Wang J W,Dai L,Liu Y Q,Li R F,Yang X T,Lan G H,Qiu H Y,Xu B.Adsorption properties of β-cyclodextrin modified hydrogel for methylene blue[J].Carbohydrate Research,2021,501:108276.
49 Junthip J.Water-insoluble cyclodextrin polymer crosslinked with citric acid for paraquat removal from water[J].Journal of Macromolecular Science,2019,56(6):555-563.
50赵春雷,赵悦,王锐,宫红,姜恒.β-环糊精/环氧氯丙烷共聚物的合成及对双酚A的吸附研究[J].离子交换与吸附,2019,35(1):50-59.
51邹东雷,唐抒圆,熊厚峰,唐绍福,李春华,陈鹏.β-环糊精交联聚合物对氯苯的吸附特性[J].吉林大学学报(地球科学版),2012,42(4):1166-1172.
52陈永明,何炳林.胺修饰β-环糊精交联树脂的制备及吸附性能[J].高等学校化学学报,1996,17(7):1157-1159.
53吴宏翔,袁镇豫,王煜,郭旭虹,王杰.基于环糊精包合作用的聚氨酯复合吸附材料[J].华东理工大学学报(自然科学版),2020,46(6):737-744.
54 Zhou Y B,Cheng G,Chen K,Lu J,Lei J Y,Pu S Y.Adsorptive removal of bisphenol A,chloroxylenol,and carbamazepine from water using a novel β-cyclodextrin polymer[J].Ecotoxicology and Environmental Safety,2019,170(Apr.):278-285.
55 Wang Z H,Zhang P B,Hu F,Zhao Y F,Zhu L P.A crosslinked β-cyclodextrin polymer used for rapid removal of a broad-spectrum of organic micropollutants from water[J].Carbohydrate Polymers,2017,177:224-231.
56赵晓斌,何炳林.β-环糊精高聚物对芳香类化合物包络吸性能研究[J].功能高分子学报,1994,7(2):148-152.
57赵晓斌,何炳林.新型包络高分子清除酚类及安眠药类化合物研究(Ⅳ)[J].南开大学学报(自然科学版),1992(4):9-14.
58 Zhao X B,He B L.Sorption of unconjugated bilirubin by means of novel immobilized β-cyclodextrin polymers[J].Reactive Polymers,1994,24:1-8.
59 Zhao X B,He B L.Synthesis and characterization of polymer-immobilized β-cyclodextrin with an inclusion recognition functionality[J].Reactive Polymers,1994,24:9-16.
60 Xu W L,Liu J D,Sun Y P.Preparation of a cyclomaltoheptaose(β-cyclodextrin) cross-linked chitosan derivative via glyoxal of glutaraldehyde[J].Chinese Chemical Letters,2003,14(9):667-770.
61 Zhang X G,Wu Z M,Gao X J.Chitosan bearing pendant cyclodextrin carrier for controlled protein release[J].Carbohydrate Polymers,2009,77:394-401.
62 Jia J,Wu D Q,Yu J Y.Upgraded β-cyclodextrin-based broad-spectrum adsorbents with enhanced antibacterial property for high-efficient dyeing wastewater remediation[J].Journal of Hazardous Materials,2024,461:132610.
63喻红竹,曹佐英,陈晓青.β-环糊精化学修饰壳聚糖及其对水中酚吸附性能的研究[J].净水技术,2006,25(4):54-57.
64魏永峰,张苏敏.具有包络作用的壳聚糖的合成及其吸附性能[J].应用化学,2005,22(7):772-775.
65 Chiu S H,Chung T W,Giridhar R,Wu W T.Immobilization of β-cyclodextrin in chitosan beads for separation of cholesterol from egg yolk[J].Food Research International,2004,37(3):217-223.
66葛亚芳,李明春,辛梅华,谢峰.壳聚糖固载环糊精微球的制备及吸附硝基酚[J].化工进展,2010,29(2):233-237.
67 Kekes T,Kolliopoulos G,Tzia C.Hexavalent chromium adsorption onto crosslinked chitosan and chitosan/β-cyclodextrin beads:novel materials for water decontamination[J].Journal of Environmental Chemical Engineering,2021,9(4):105581.
68 Usman M,Ahmed A,Yu B,Wang S,Cong H L.Simultaneous adsorption of heavy metals and organic dyes byβ-cyclodextrin-Chitosan based cross-linked adsorbent[J].Carbohydrate Polymers,2021,255:117486.
69 Srivastava S K,Singh A K,Shaema A.Studies on the uptake of lead and zinc by lignin obtained from black liquor:a paper industry waste material[J].Environmental Technology,1994,15(4):353-361.
70何莼,李忠,赵桢霞,奚红霞.低成本木质素吸附剂对废水中Pb2+吸附性能的研究[J].离子交换与吸附,2006,22(6):481-488.
71胡春平,方桂珍,李志娜,金钟玲.木质素基β-环糊精醚的合成及对Cu2+的吸附性能[J].中国造纸学报,2008,23(4):148-152.
72 Mpatani F M,Aryee A A,Kani A N,Guo Q H,Dovi E,Qu L B,Li Z H,Han R P.Uptake of micro pollutantbisphenol A,methylene blue and neutral red onto a novel bagasse-β-cyclodextrin polymer by adsorption process[J].Chemosphere,2020,259:127439.
73鲁冠秀,刘庆文,孔祥怡,丛乐乐,宋岩,赵晴,杨清彪,李耀先.PVA/GA/β-CD纳米纤维的制备及染料吸附性能[J].高等学校化学学报,2018,38(8):1465-1469.
74张旺,陈铭,刁国旺.β-环糊精功能化聚丙烯腈纳米纤维的制备及对亚甲基蓝的吸附性能[J].高等学校化学学报,2011,32(9):2227-2230.
75范毅,冯钰铸,达世禄,施治国,徐丽.β-环糊精键合改性介孔硅胶的表征和吸附性能评价[J].应用化学,2004,24(9):878-883.
76 Huq R,Mercier L.Incorporation of cyclodextrin into mesostructured silica[J].Chemistry of Materials,2001,13(12):4512-4519.
77 Yang Z G,Liu X Z,Liu X P,Wu J F,YU Z S.Preparation of β-cyclodextrin/graphene oxide and its adsorption properties for methylene blue[J].Colloids and Surfaces B:Biointerfaces,2021,200:111605.
78邹静,王芳辉,杨艳丽,马少华.环糊精氧化石墨烯复合材料的制备及其对Cu2+的吸附性能研究[J].中国塑料,2019,33(4):17-21.
79 Morin-Crini N,Winterton P,Fourmentin S,Wilson L D,Fenyvesi V,Crini G.Water-insoluble β-cyclodextrinepichlorohydrin polymers for removal of pollutants from aqueous solutions by sorption processes using batch studies:A review of inclusion mechanisms[J].Progress in Polymer Science,2018,78:1-23.
80 Zhao D,Zhao L,Zhu C S,Huang W Q,Hu J L.Water-insoluble β-cyclodextrin polymer crosslinked by citric acid:synthesis and adsorption properties toward phenol and methylene blue[J].Journal of Inclusion Phenomenon Macrocyclic Chemistry,2009,63:195-201.
81 Sancey B,Trunfio G,Charles J,Badot P M,Crini G.Sorption onto crosslinked cyclodextrin polymers for industrial pollutant removal:an interesting environmental approach[J].Journal of Inclusion Phenomenon Macrocyclic Chemistry,2011,70:316-320.
82何炳林,赵晓斌.新型β-环糊精固载化高分子对内、外源性毒物的包络吸附研究[J].高等学校化学学报,1992,13(7):1006-1107.
基本信息:
DOI：10.16026/j.cnki.iea.2024040284
中图分类号:TQ424;X703
引用信息:
[1]金秋,王霄鹏,王丽霞等.含环糊精吸附剂的合成与应用[J].离子交换与吸附,2024,40(04):284-295.DOI:10.16026/j.cnki.iea.2024040284.
基金信息: