聚多巴胺/聚乙烯亚胺复合非织造布/Fe2+活化过硫酸盐催化氧化酸性红B的效果分析

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秦文欣¹,
张环^1,2,,,
李欣¹,
胥京福¹,
屈静¹,
吴茜¹
1.天津工业大学环境科学与工程学院，天津 300387
2.天津工业大学，省部共建分离膜与膜过程国家重点实验室，天津 300387

作者简介: 秦文欣(1994—)，女，硕士研究生。研究方向：功能材料及应用。E-mail：923769710@.qq.com.

通讯作者: 张环,zhanghuan@tiangong.edu.cn ;

中图分类号: X703

Effect analysis of catalytic oxidation of acid red B by polydopamine/ polyethyleneimine nonwoven/Fe²⁺ activated persulfate

QIN Wenxin¹,
ZHANG Huan^1,2,,,
LI Xin¹,
XU Jingfu¹,
QU Jing¹,
WU Qian¹
1.School of Environmental Science and Engineering, Tiangong University, Tianjin 300387, China
2.State Key Laboratory of Separation Membranes and Membrane Processes, Tiangong University, Tianjin 300387, China

Corresponding author: ZHANG Huan,zhanghuan@tiangong.edu.cn ;

CLC number: X703

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摘要:以聚丙烯(PP)非织造布为基体，采用多巴胺聚乙烯亚胺共沉积法制备了聚多巴胺/聚乙烯亚胺复合非织造布(PDA/PEI@PP)，研究了PDA/PEI@PP在Fe²⁺活化过硫酸盐(PS)降解酸性红B(ARB)的中的性能和反应机理。通过SEM对材料结构进行了表征，考察了不同体系(PS、PDA/PEI@PP/PS、Fe²⁺/PS和PDA/PEI@PP/Fe²⁺/PS)中ARB的降解效果，通过电子自旋共振波谱(ESR)和傅里叶红外光谱(FT-IR)分析了PDA/PEI@PP活化PS及自由基生成的机理，此外，考察了PDA/PEI@PP对Fe³⁺的还原作用。结果表明：PDA/PEI@PP非织造材料具有贯穿的孔道结构，利于PDA/PEI@PP表面官能团对PS的活化；PDA/PEI@PP对Fe²⁺/PS体系的催化氧化具有促进作用，当Fe²⁺初始浓度为0.5 mmol·L^?1时，90 min内对ARB的降解率为98%，反应速率常数为0.040 min^?1；在不添加Fe²⁺的情况下，PDA/PEI@PP可直接活化PS产生自由基降解ARB，降解率为56%；PDA/PEI@PP表面的邻苯二酚基团与邻醌基反应生成半醌，从而活化PS产生硫酸根自由基($ {\rm{SO}}_4^{ \cdot - } $

)和羟基自由基(·OH)；同时PDA/PEI@PP表面的邻苯二酚基团也对Fe³⁺具有还原作用，生成Fe²⁺持续活化PS。因此，PDA/PEI@PP对于Fe²⁺活化PS的促进作用主要是通过PDA/PEI@PP对PS协同活化和对Fe³⁺的还原作用来实现的。本研究为进一步提高Fe²⁺活化PS氧化降解染料废水的效率提供了一种较好的解决方案。
关键词: 聚多巴胺/聚乙烯亚胺复合非织造布(PDA/PEI@PP)/
邻苯二酚基团/
邻醌基/
Fe²⁺/
过硫酸盐/
酸性红B

Abstract:In this study, polypropylene (PP) nonwoven was taken as matrix, the co-deposition method of dopamine and polyethyleneimine was used to prepare the polydopamine/polyethyleneimine-functionalized polypropylene nonwoven (PDA/PEI@PP). The performance and mechanism of PDA/PEI@PP on Fe²⁺ activated persulfate (PS) and degrading acid red B (ARB) were studied. SEM was used to characterize the PDA/PEI@PP material. The ARB degradation effects in different systems of PS, PDA/PEI@PP/PS, Fe²⁺/PS and PDA/PEI@PP/Fe²⁺/PS were also studied. Electron spin-resonance spectroscopy (ESR) and Fourier transform infrared (FT-IR) were used to identify the mechanism of PDA/PEI@PP activated PS and radicals formation. In addition, the reduction of Fe³⁺ by PDA/PEI@PP was investigated. The results showed that the throughout pore structure was presented in PDA/PEI@PP nonwoven material, which facilitated PS activation by the surface functional groups of PDA/PEI@PP. PDA/PEI@PP could promote the catalytic oxidation of Fe²⁺/PS system, the degradation rate of ARB could reach 98% within 90 min when the initial content of Fe²⁺ was 0.5 mmol·L^?1, and the reaction rate constant was 0.040 min^?1. Without the addition of Fe²⁺, PDA/PEI@PP could directly activate PS, produce radicals for ARB degradation with a rate of 56%. On the surface of PDA/PEI@PP, the catechol groups reacted with o-quinone groups to produce semiquinone, which could activate PS and produce sulfate radical ($ {\rm{SO}}_4^{ \cdot - } $

) and hydroxyl radical (·OH). At the same time, the catechol groups on the surface of PDA/PEI@PP also could reduce the Fe³⁺ to Fe²⁺, which could sustainably activate PS. Therefore, the promoting effects of PDA/PEI@PP on Fe²⁺ activated PS are mainly due to the synergetic activation of PS and Fe³⁺ reduction by PDA/PEI@PP. The study provides a better solution for further improving the efficiency of oxidation degradation of dye wastewater by Fe²⁺ activated PS.
Key words:polydopamine/polyethyleneimine-functionalized polypropylene nonwoven(PDA/PEI@PP)/
catechol group/
o-quinone group/
ferrous iron/
persulfate/
acid red B.

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图1PP非织造材料和PDA/PEI@PP材料扫描电镜图
Figure1.SEM images of the PP nonwoven materials and PDA/PEI@PP materials

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图2不同反应体系对ARB降解性能和PS分解性能的影响
Figure2.Effects of different reaction systems on ARB degradation performance and PS decomposition performance

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图3催化反应动力学分析
Figure3.Kinetics analysis of catalytic reaction

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图4不同体系反应溶液中氧化性自由基的ESR图谱
Figure4.ESR spectra of oxidative radicals in reaction solutions of different systems

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图5PDA/PEI@PP/PS反应溶液中氧化性自由基的ESR图谱
Figure5.ESR spectra of oxidative radicals in PDA/PEI@PP/PS reaction solution

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图6PDA/PEI@PP活化PS前后FT-IR谱图
Figure6.FT-IR spectra before and after PDA/PEI@PP activation PS

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图7PDA/PEI@PP对Fe³⁺的还原
Figure7.Fe³⁺ reduction by PDA/PEI@PP

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图8PDA/PEI@PP对Fe²⁺/PS体系促进作用机制
Figure8.Promotion mechanism of PDA/PEI@PP on Fe²⁺/PS system

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图9PDA/PEI@PP循环使用次数对ARB降解的影响
Figure9.Effects of PDA/PEI@PP cycle times on ARB degradation

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出版历程

收稿日期:2020-01-13
录用日期:2020-03-07
网络出版日期:2020-12-08
-->刊出日期:2020-12-10

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聚多巴胺/聚乙烯亚胺复合非织造布/Fe²⁺活化过硫酸盐催化氧化酸性红B的效果分析

秦文欣¹,
张环^1,2,,,
李欣¹,
胥京福¹,
屈静¹,
吴茜¹

通讯作者: 张环,zhanghuan@tiangong.edu.cn ;

作者简介: 秦文欣(1994—)，女，硕士研究生。研究方向：功能材料及应用。E-mail：923769710@.qq.com 1.天津工业大学环境科学与工程学院，天津 300387
2.天津工业大学，省部共建分离膜与膜过程国家重点实验室，天津 300387
收稿日期: 2020-01-13
录用日期: 2020-03-07
网络出版日期: 2020-12-08
关键词: 聚多巴胺/聚乙烯亚胺复合非织造布(PDA/PEI@PP)/
邻苯二酚基团/
邻醌基/
Fe²⁺/
过硫酸盐/
酸性红B
摘要:以聚丙烯(PP)非织造布为基体，采用多巴胺聚乙烯亚胺共沉积法制备了聚多巴胺/聚乙烯亚胺复合非织造布(PDA/PEI@PP)，研究了PDA/PEI@PP在Fe²⁺活化过硫酸盐(PS)降解酸性红B(ARB)的中的性能和反应机理。通过SEM对材料结构进行了表征，考察了不同体系(PS、PDA/PEI@PP/PS、Fe²⁺/PS和PDA/PEI@PP/Fe²⁺/PS)中ARB的降解效果，通过电子自旋共振波谱(ESR)和傅里叶红外光谱(FT-IR)分析了PDA/PEI@PP活化PS及自由基生成的机理，此外，考察了PDA/PEI@PP对Fe³⁺的还原作用。结果表明：PDA/PEI@PP非织造材料具有贯穿的孔道结构，利于PDA/PEI@PP表面官能团对PS的活化；PDA/PEI@PP对Fe²⁺/PS体系的催化氧化具有促进作用，当Fe²⁺初始浓度为0.5 mmol·L^?1时，90 min内对ARB的降解率为98%，反应速率常数为0.040 min^?1；在不添加Fe²⁺的情况下，PDA/PEI@PP可直接活化PS产生自由基降解ARB，降解率为56%；PDA/PEI@PP表面的邻苯二酚基团与邻醌基反应生成半醌，从而活化PS产生硫酸根自由基($ {\rm{SO}}_4^{ \cdot - } $)和羟基自由基(·OH)；同时PDA/PEI@PP表面的邻苯二酚基团也对Fe³⁺具有还原作用，生成Fe²⁺持续活化PS。因此，PDA/PEI@PP对于Fe²⁺活化PS的促进作用主要是通过PDA/PEI@PP对PS协同活化和对Fe³⁺的还原作用来实现的。本研究为进一步提高Fe²⁺活化PS氧化降解染料废水的效率提供了一种较好的解决方案。

English Abstract

Effect analysis of catalytic oxidation of acid red B by polydopamine/ polyethyleneimine nonwoven/Fe²⁺ activated persulfate

QIN Wenxin¹,
ZHANG Huan^1,2,,,
LI Xin¹,
XU Jingfu¹,
QU Jing¹,
WU Qian¹

Corresponding author: ZHANG Huan,zhanghuan@tiangong.edu.cn ;

1.School of Environmental Science and Engineering, Tiangong University, Tianjin 300387, China
2.State Key Laboratory of Separation Membranes and Membrane Processes, Tiangong University, Tianjin 300387, China
Received Date: 2020-01-13
Accepted Date: 2020-03-07
Available Online: 2020-12-08
Keywords: polydopamine/polyethyleneimine-functionalized polypropylene nonwoven(PDA/PEI@PP)/
catechol group/
o-quinone group/
ferrous iron/
persulfate/
acid red B
Abstract:In this study, polypropylene (PP) nonwoven was taken as matrix, the co-deposition method of dopamine and polyethyleneimine was used to prepare the polydopamine/polyethyleneimine-functionalized polypropylene nonwoven (PDA/PEI@PP). The performance and mechanism of PDA/PEI@PP on Fe²⁺ activated persulfate (PS) and degrading acid red B (ARB) were studied. SEM was used to characterize the PDA/PEI@PP material. The ARB degradation effects in different systems of PS, PDA/PEI@PP/PS, Fe²⁺/PS and PDA/PEI@PP/Fe²⁺/PS were also studied. Electron spin-resonance spectroscopy (ESR) and Fourier transform infrared (FT-IR) were used to identify the mechanism of PDA/PEI@PP activated PS and radicals formation. In addition, the reduction of Fe³⁺ by PDA/PEI@PP was investigated. The results showed that the throughout pore structure was presented in PDA/PEI@PP nonwoven material, which facilitated PS activation by the surface functional groups of PDA/PEI@PP. PDA/PEI@PP could promote the catalytic oxidation of Fe²⁺/PS system, the degradation rate of ARB could reach 98% within 90 min when the initial content of Fe²⁺ was 0.5 mmol·L^?1, and the reaction rate constant was 0.040 min^?1. Without the addition of Fe²⁺, PDA/PEI@PP could directly activate PS, produce radicals for ARB degradation with a rate of 56%. On the surface of PDA/PEI@PP, the catechol groups reacted with o-quinone groups to produce semiquinone, which could activate PS and produce sulfate radical ($ {\rm{SO}}_4^{ \cdot - } $

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--> --> --> 基于硫酸根自由基($ {\rm{SO}}_4^{ \cdot - } $)的高级氧化技术具有选择性小、反应条件温和、高效、快速等优势，已引起国内外****的广泛关注^[1-2]。过硫酸盐(PS)在过渡金属、碱、热等作用下，可激发过硫酸盐中的过氧基(—O—O—)产生硫酸根自由基^[3-5]。过渡金属中的Fe²⁺因来源广泛、环境友好，因此，Fe²⁺活化是目前研究最多的一种活化方法。Fe²⁺活化PS也具有一些局限性，在加入少量Fe²⁺后，Fe²⁺被快速氧化成Fe³⁺，无法再生，故不利于反应持续有效地进行；但增加Fe²⁺的用量，会导致体系中自由基的淬灭反应。因此，Fe²⁺/PS体系中可引入具有还原性的物质，以保证PS活化过程持续有效进行。
近年来，一些含有氧化敏感型官能团结构的有机物如(醌类^[6]、酚类^[7-8]、醇类^[9])被证实对过硫酸盐具有活化作用。而这些有机化合物主要是通过自身含氧官能团电子的得失，形成苯氧自由基，从而引发电子转移激活PS。FANG等^[6]的研究表明，在一定条件下，对苯醌与对苯酚之间通过电子的转移，可生成具有活化PS作用的半醌自由基(HQ·)。邻苯醌在水相中有类似于对醌的3种形态：完全还原态(H₂Q)、中间氧化态(HQ·)、完全氧化态(Q)^[10]。多巴胺(DA)是一种具有邻苯二酚结构的有机化合物，可通过氧化自聚形成具有酚醌结构的聚多巴胺^[11-12]，其酚醌之间也可进行电子转移^[13]，可促进PS的活化生成硫酸根自由基。
本研究以PP非织造材料为基体，采用多巴胺(DA)和聚乙烯亚胺(PEI)共沉积法制备了PDA/PEI@PP材料，多巴胺和聚乙烯亚胺可通过交联共沉积作用附着在固体表面^[14]，制备得到稳定性好、亲水性强且具有酚醌共存结构的复合材料。LENG等^[15]的研究表明，具有电子穿梭作用的苯二酚对Fe³⁺具有还原作用，而PDA/PEI@PP表面也具有邻苯二酚结构^{[14, 16]}，对Fe³⁺可能具有一定的还原作用。因此，本研究将PDA/PEI@PP引入Fe²⁺活化过硫酸盐体系中，考察了同时具有邻苯醌和邻苯二酚结构的PDA/PEI@PP材料对Fe²⁺/PS体系的协同催化活化性能及相关的机理，探讨了PDA/PEI@PP材料在过硫酸体系中对Fe³⁺的还原作用，旨在为提高Fe²⁺活化PS氧化降解污染物提供一种新途径。

1. 材料与方法

1.1. 实验材料

主要原料与试剂：聚丙烯非织造布(PP)为工业级；多巴胺(DA)、三羟甲基-氨基甲烷(Tris)、聚乙烯亚胺(PEI)、过硫酸钠(Na₂S₂O₈，PS)、七水合硫酸亚铁、三氯化铁(无水)、酸性红B(acid red B，ARB)、碘化钾(KI)、碳酸氢钠、氢氧化钠、浓硫酸、盐酸、5,5-二甲基-1-吡咯啉-N-氧化物(DMPO)、邻菲罗啉、无水乙醇、叔丁醇均为分析纯，实验用水为超纯水。

1.2. PDA/PEI@PP材料的制备及表征

配制0.01 mmol·L^?1的Tris(三羟甲基-氨基甲烷)缓冲溶液，调节pH为8.5，加入一定量的多巴胺和聚乙烯亚胺，按照DA∶PEI=1∶1的质量比，配制成DA/PEI混合液。将用乙醇润湿的非织造布(1.0 g)置于DA/PEI混合溶液中，在恒温水浴中，25 ℃振荡反应12 h。反应后，用蒸馏水洗去非织造布表面未反应的聚合物，并在60 ℃的恒温干燥箱中烘至恒重，得到PDA/PEI@PP样品。通过扫描电镜(SEM)和傅里叶红外光谱(FT-IR)对PDA/PEI@PP材料表面形貌、结构和官能团进行分析。

1.3. 过硫酸盐体系催化ARB的降解实验

在实验过程中，向200 mL反应体系中分别投加PDA/PEI@PP、FeSO₄·7H₂O和过硫酸盐(PS)等其他组分，体系中ARB的浓度为0.2 mmol·L^?1。将反应液置于恒温水浴中，在25 ℃下均速搅拌，分别在0、2、5、10、20、30、40、50、60、70、80、90 min时移取3 mL待测样于比色皿中，测定ARB浓度。

1.4. 分析与测定方法

采用分光光度法测定ARB的浓度，采用KI显色法^[17]测定反应体系中PS的浓度，采用邻菲罗啉法测定溶液中的Fe²⁺。以DMPO作为捕捉剂，应用电子自旋共振波谱(ESR)仪对体系中的自由基进行检测和分析。ARB的去除率的计算方法如式(1)所示。ARB催化降解的反应符合动力学一级反应的特征，准一级动力学方程如式(2)所示。PS的分解率的计算方法如式(3)所示。
式中：R为ARB的去除率；C₀为ARB的初始浓度，mg·L^?1； C_t为t时的ARB浓度，mg·L^?1； k为反应速率常数，min^?1；y为与反应体系相关的参数。$R'$为PS的分解率；$C_0^{'}$为PS的初始浓度，mg·L^?1；$C_t^{'}$为t时的PS浓度，mg·L^?1。

3. 结论

1)冷场扫描电镜分析结果表明，PDA/PEI@PP保持PP非织造材料原有的孔道结构。通过热场扫描电镜，对材料纤维表面的分析结果表明，非织造纤维上均匀附着一层聚多巴胺/聚乙烯亚胺复合物。
2)将PDA/PEI@PP引入Fe²⁺/PS体系可有效促进Fe²⁺/PS体系对ARB的降解。Fe²⁺浓度的增加，对PDA/PEI@PP促进Fe²⁺/PS体系的ARB的降解和反应速率均有影响。
3) PDA/PEI@PP的引入增加了Fe²⁺/PS体系中羟基自由基的产率，且PDA/PEI@PP可在短时间内活化PS产生硫酸根自由基和羟基自由基。
4) PDA/PEI@PP上的邻苯二酚基团可与邻醌基反应，生成半醌基进而活化PS。通过PDA/PEI@PP对Fe³⁺的还原作用研究，发现PDA/PEI@PP上的邻苯二酚基对Fe³⁺也具有还原作用。
5)随着PDA/PEI@PP重复利用次数的增加，PDA/PEI@PP表面的邻苯二酚基团不断被消耗，从而生成醌基，因此，PDA/PEI@PP在Fe²⁺/PS体系中的促进作用也随之逐渐减弱。

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