负载型酞菁用于水和空气中有机污染物的可见光催化降解研究进展

doi:10.16085/j.issn.1000-6613.2017-0018

摘要/Abstract

摘要： 负载化可以有效提高酞菁的光稳定性，降低其在溶液中的聚集，同时解决其回收再利用的问题，但酞菁负载的方法及载体种类众多，如何选择适合的负载方法和载体是应用过程中存在的重要问题。本文介绍了酞菁类光催化剂的结构特性和光催化机制，综述了用于水和空气中有机污染物可见光催化降解的负载型酞菁的载体种类及负载方法，对比分析了各种载体以及负载方法的优势、不足和适用范围，指出需要根据酞菁的物化性质及应用要求来选择载体与负载方法。而针对负载化酞菁新的应用要求，提出复合功能载体应是未来的发展方向。

关键词: 酞菁, 载体, 可见光催化, 污染, 有机化合物

Abstract: Immobilization of phthalocyanines(Pcs)onto supports can efficiently improve their photostability,reduce their aggregation,as well as solve the recycle problems of them. However,there are too many kinds of supports and immobilization methods for Pcs' immobilization,and how to choose the suitable one is a problem. This review focuses on the structure and photo mechanisms of Pcs,as well as the supports and immobilization methods of immobilized Pcs. Moreover,the comparison of each support and methodologies for immobilization and the application of these supports and methodologies are also mentioned. Accordingly,it is pointed that the support and immobilization method should be chosen according to the physicochemical properties of Pcs and application requirements. Besides,it is suggested that the composite support is the future development direction.

Key words: phthalocyanines, support, visible light photocatalysis, pollution, organic compounds

中图分类号:

O644.1

王傲, 孙康, 蒋剑春. 负载型酞菁用于水和空气中有机污染物的可见光催化降解研究进展[J]. 化工进展, 2017, 36(09): 3475-3484.

WANG Ao, SUN Kang, JIANG Jianchun. Immobilized phthalocyanines for visible light photodegradation of organic pollutants in water and air[J]. Chemical Industry and Engineering Progress, 2017, 36(09): 3475-3484.

参考文献

[1] ANDREOZZI R,CAPRIO V,INSOLA A,et al. Advanced oxidation processes(AOP) for water purification and recovery[J]. Catal. Today,1999,53(1):51-59.
[2] ESPLUGAS S,GIMENEZ J,CONTRERAS S,et al. Comparison of different advanced oxidation processes for phenol degradation[J]. Water Res.,2002,36(4):1034-1042.
[3] OPENLANDER T. Photochemical purification of water and air. Advanced oxidation processes (AOPs):principles,reaction mechanisms,reactor concepts[M]. Germany:Wiley,VCH:Weinheim,2003.
[4] HAY S O,OBEE T,LUO Z,et al. The viability of photocatalysis for air purification[J]. Molecules,2015,20(1):1319-1356.
[5] MARIN M L,JUANES L S,ARQUES A,et al. Organic photocatalysts for the oxidation of pollutants and model compounds[J]. Chem. Rev.,2012,112(3):1710-1750.
[6] BRASLAVSKY S E. Glossary of terms used in photochemistry,(IUPAC Recommendations 2006)[J]. Pure Appl. Chem.,2007,79(3):293-465.
[7] 何东林,黄洪,钟理. TiO₂可见光催化研究进展及其应用前景[J]. 化工进展,2015,34(s1):104-109. HE D L,HUANG H,ZHONG L. Research progress and applied prospect of TiO₂ visible light photocatalysis[J]. Chemical Industry and Engineering Progress,2015,34(s1):104-109.
[8] CAREY J H,LAWRENCE J,TOSINE H M. Photodechlorination of PCB's in the presence of titanium dioxide in aqueous suspensions[J]. Bull. Environ. Contam. Toxicol.,1976,16(6):697-701.
[9] DONG H,ZENG G,TANG L,et al. An overview on limitations of TiO₂-based particles for photocatalytic degradation of organic pollutants and the corresponding countermeasures[J]. Water Res.,2015,79:128-146.
[10] ZANGENEH H,ZINATIZADEH A A L,HABIBI M,et al. Photocatalytic oxidation of organic dyes and pollutants in wastewater using different modified titanium dioxides:a comparative review[J]. J. Ind. Eng. Chem.,2015,26:1-36.
[11] 陈颖芝,王鲁宁. 有机光催化剂的研究进展[J]. 化学工业与工程,2015,32(3):30-37. CHEN Y Z,WANG L N. Research progress of organic photocatalysts[J]. Chem. Ind. Eng.,2015,32(3):30-37.
[12] LACOMBE S,PIGOT T. Materials for selective photo-oxygenation vs. photocatalysis:preparation,properties and applications in environmental and health fields[J]. Catal. Sci. Technol.,2016,6(6):1571-1592.
[13] 徐延明,赵明,李坚,等. 氨基酞菁-二氧化钛可见-近红外光催化剂的制备及其性能[J]. 化工学报,2016,67(5):1915-1921. XU Y M,ZHAO M,LI J,et al. Visible near-infrared amino phthalocyanine-titanium dioxide photocatalyst:preparation and performance[J]. CIESC Journal,2016,67(5):1915-1921.
[14] ZHANG X,YU L,ZHUANG C,et al. Highly asymmetric phthalocyanine as a sensitizer of graphitic carbon nitride for extremely efficient photocatalytic H₂ production under near-infrared light[J]. ACS Catal.,2014,4(1):162-170.
[15] FERNANDEZ L,ESTEVES V I,CUNHA A,et al. Photodegradation of organic pollutants in water by immobilized porphyrins and phthalocyanines[J]. J. Porphyrins Phthalocyanines,2016,20:1-17.
[16] XU T,NI D,CHEN X,et al. Self-floating graphitic carbon nitride/zinc phthalocyanine nanofibers for photocatalytic degradation of contaminants[J]. J. Hazard. Mater.,2016,317:17-26.
[17] 张娟,胡颜荟,任腾杰,等. Ti-MCM-41负载酞菁铁光催化氧化脱硫[J]. 化工学报,2015,66(9):3437-3443. ZHANG J,HU Y H,REN T J,et al. Photocatalytic oxidation desulfurization by iron phthalocyanine supported on Ti-MCM-41[J]. CIESC Journal,2015,66(9):3437-3443.
[18] 陈振华,刘威尚,周文博,等. 负载化/固载化酞菁金属催化剂研究进展[J]. 工业催化,2012,20(8):6-12. CHEN Z H,LIU W S,ZHOU W B,et al. Advance on supported/immobilized phthalocyanine metal catalysts[J]. Ind. Catal., 2012,20(8):6-12.
[19] NYOKONG T. Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines[J]. Coord. Chem. Rev.,2007,251(13):1707-1722.
[20] YAKU H,FUJIMOTO T,MURASHIMA T,et al. Phthalocyanines:a new class of G-quadruplex-ligands with many potential applications[J]. Chem. Commun.,2012,48(50):6203-6216.
[21] DUMOULIN F,DURMUS M,AHSEN V,et al. Synthetic pathways to water-soluble phthalocyanines and close analogs[J]. Coord. Chem. Rev.,2010,254(23):2792-2847.
[22] STUZHIN P A,KHELEVINA O G,BEREZIN B D. Phthalocyanines:properties and applications[M]. New York:VCH,1996.
[23] LU Y,REDDY R G. The electrochemical behavior of cobalt phthalocyanine/platinum as methanol-resistant oxygen-reduction electrocatalysts for DMFC[J]. Electrochim. Acta,2007,52(7):2562-2569.
[24] OZCESMECI M,ECEVIT O B,SURGUN S,et al. Tetracationic fluorinated zinc (Ⅱ) phthalocyanine:synthesis,characterization and DNA-binding properties[J]. Dyes. Pigm.,2013,96(1):52-58.
[25] 沈永嘉. 酞菁的合成与应用[M]. 北京:化学工业出版社,2000. SHEN Y J. Synthesis and application of phthalocyanines[M]. Beijing:Chemical Industry Press,2000.
[26] 王傲. 多胺类酞菁及其水溶性衍生物的合成与性质研究[D]. 南京:南京师范大学,2013. WANG A. Studies on synthesis and properties of phthalocyanines and their soluble polyamine derivatives[D]. Nanjing:Nanjing Normal University,2013.
[27] JIANG J. Functional phthalocyanine molecular materials[M]. Berlin:Springer,2010.
[28] SOROKIN A B. Phthalocyanine metal complexes in catalysis[J]. Chem. Rev.,2013,113(10):8152-8191.
[29] 师雁,宁平,王学谦,等. 改性炭对H₂S吸附性能的研究[J]. 化工进展,2009,28(5):890-893. SHI Y,NING P,WANG X Q,et al. Treatment of H₂S by modified activated carbon[J]. Chemical Industry and Engineering Progress,2009,28(5):890-893.
[30] CHENG H,CHOU S,CHEN S,et al. Photoassisted Fenton degradation of phthalocyanine dyes from wastewater of printing industry using Fe(Ⅱ)/γ-Al₂O₃ catalyst in up-flow fluidized-bed[J]. J. Environ. Sci.,2014,26(6):1307-1312.
[31] CHANG C F,MAN C Y. Magnetic photocatalysts of copper phthalocyanine-sensitized titania for the photodegradation of dimethyl phthalate under visible light[J]. Colloid. Surface. A,2014,441:255-261.
[32] SUN W,LI J,MELE G,et al. Enhanced photocatalytic degradation of rhodamine B by surface modification of ZnO with copper (Ⅱ) porphyrin under both UV-vis and visible light irradiation[J]. J. Mol. Catal. A:Chem.,2013,366:84-91
[33] VALENTE A,PALMA C,FONSECA I M,et al. Oxidation of pinane over phthalocyanine complexes supported on activated carbon:effect of the support surface treatment[J]. Carbon,2003,41(14):2793-2803.
[34] WANG D J,GUO R,WANG S J,et al. Synthesis and characterization of cobalt phthalocyanine/MCM-41 and its photocatalytic activity on methyl orange under visible light[J]. Desalin. Water Treat,2016,57(52):25226-25234.
[35] DEROSA M C,CRUTCHLEY R J. Photosensitized singlet oxygen and its applications[J]. Coord. Chem. Rev.,2002,233:351-371.
[36] OLLER I,MALATO S,Sanchez-Perez J A. Combination of advanced oxidation processes and biological treatments for wastewater decontamination-a review[J]. Sci. Total Environ.,2011,409(20):4141-4166.
[37] WAN Y,CHEN S,WANG G,et al. Facile synthesis and characterization of zinc tetranitro phthalocyanine-MWCNTs nanocomposites with efficient visible-light-driven photocatalytic activity[J]. Acta Physica Polonica A,2016,130(3):785-790.
[38] KUMAR P,KUMAR A,SREEDHAR B,et al. Cobalt phthalocyanine immobilized on graphene oxide:an efficient visible-active catalyst for the photoreduction of carbon dioxide[J]. Chem. Eur. J.,2014,20(20):6154-6161.
[39] GOVAN J,GUNKO Y K. Recent advances in the application of magnetic nanoparticles as a support for homogeneous catalysts[J]. Nanomaterials,2014,4(2):222-241.
[40] MODISHA P,NYOKONG T,ANTUNES E. Photodegradation of orange-G using zinc octacarboxyphthalocyanine supported on Fe₃O₄ nanoparticles[J]. J. Mol. Catal. A:Chem.,2013,380:131-138.
[41] CALVETE M J F,SILVA M,PEREIRA M M,et al. Inorganic helping organic:recent advances in catalytic heterogeneous oxidations by immobilised tetrapyrrolic macrocycles in micro and mesoporous supports[J]. RSC Adv.,2013,3(45):22774-22789.
[42] 夏道宏,张杰,徐斌,等. 一种负载型脱硫剂的制备方法:200810113361.1[P]. 2009-12-02. XIA D H,ZHANG J,XU B,et al. Preparation method of load type desulfurizing agent:200810113361.1[P]. 2009-12-02.
[43] SHAO L,XING G,LV W,et al. Photodegradation of azo-dyes in aqueous solution by polyacrylonitrile nanofiber mat-supported metalloporphyrins[J]. Polym. Int.,2012,62(2):289-294.
[44] ZHANG M,MURAKAMI T,AJIMA K,et al. Fabrication of ZnPc/protein nanohorns for double photodynamic and hyperthermic cancer phototherapy[J]. P. Natl. Acad. Sci.,2008,105(39):14773-14778.
[45] OGUNBAYO T B,NYOKONG T. Phototransformation of 4-nitrophenol using Pd phthalocyanines supported on single walled carbon nanotubes[J]. J. Mol. Catal. A:Chem.,2011,337(1):68-76.
[46] ZANJANCHI M A,EBRAHIMIAN A,ARVAND M. Sulphonated cobalt phthalocyanine-MCM-41:an active photocatalyst for degradation of 2,4-dichlorophenol[J]. J. Hazard. Mater.,2010,175(1):992-1000.
[47] YAO Y,CHEN W,LU S,et al. Binuclear metallophthalocyanine supported on treated silk fibres as a novel air-purifying material[J]. Dyes Pigm.,2007,73(2):217-223.
[48] SHIBATA H,OHSHIKA S,OGURA T,et al. Preparation and photocatalytic activity under visible light irradiation of mesostructured titania particles modified with phthalocyanine in the pores[J]. J. Photochem. Photobiol. A,2011,217(1):136-140.
[49] 朱淑英,魏征,尹丽娜,等. 酞菁钴/MCM-41的合成、表征及催化性质[J]. 沈阳化工学院学报,2007,21(2):109-111. ZHU S Y,WEI Z,YIN L N,et al. Synthesis,characterization and catalytic performance of CoPc/MCM-41[J]. Journal of Shenyang Institute of Chemical Technology,2007,21(2):109-111.
[50] SOROKIN A B,TUEL A. Metallophthalocyanine functionalized silicas:catalysts for the selective oxidation of aromatic compounds[J]. Catal. Today,2000,57(1):45-59.
[51] SOROKIN A B,MANGEMATIN S,PERGRALE C. Selective oxidation of aromatic compounds with dioxygen and peroxides catalyzed by phthalocyanine supported catalysts[J]. J. Mol. Catal. A:Chem.,2002,182:267-281.
[52] 陈文兴,陈世良,吕慎水,等. 负载型酞菁催化剂的制备及其光催化氧化苯酚[J]. 中国科学(B辑),2007,37(4):369-373. CHEN W X,CHEN S L,LV S S,et al. Preparation of supported phthalocyanine catalyst and its photocatalytic oxidation of phenol[J]. Science in China:B, 2007,37(4):369-373.
[53] HUANG Z,ZHENG B,ZHU S,et al. Photocatalytic activity of phthalocyanine-sensitized TiO₂-SiO₂ microparticles irradiated by visible light[J]. Mater. Sci. Semicond. Process,2014,25:148-152.
[54] ZAKHAROV V Y,ZAKHAROVA O M,ROMANOVSKⅡ B V. Determination of dispersity of phthalocyanines in a zeolite matrix[J]. React. Kinet. Catal. Lett.,1977,6(2):133-137.
[55] 梁士昌,周家顺,邓文安,等. 分子筛超笼中酞菁钴的原位合成与表征[J]. 中国石油大学学报(自然科学版),2001,25(3):55-58. LIANG S C,ZHOU J S,DENG W A,et al. Synthesis and characterization of the encapsulated cobalt phthalocyanine in supercages of zeolite[J]. Journal of the University of Petroleum China,2001,25(3):55-58.
[56] WOHRLE D,BAZIAKINA N,SUVOROVA O,et al. Phthalocyanine coatings on silica and zinc oxide. synthesis and their activities in the oxidation of sulfide[J]. J. Porphyrins Phthalocyanines,2004,8(12):1390-1401.
[57] WAN Y,CONG T,LIANG Q,et al. Facile in-situ solvothermal method to synthesize ZnPc-MWCNTs composites with enhanced visible light photocatalytic activity[J]. Ceram. Int.,2016,42(2):2425-2430.