Efficient recovery of aromatic compounds from the wastewater of styrene monomer and propylene oxide co-production plant via hypercrosslinked aryl-rich starch-β-cyclodextrin polymeric sorbent

doi:10.1016/j.cjche.2022.04.009

Chinese Journal of Chemical Engineering ›› 2022, Vol. 49 ›› Issue (9): 150-160.DOI: 10.1016/j.cjche.2022.04.009

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Efficient recovery of aromatic compounds from the wastewater of styrene monomer and propylene oxide co-production plant via hypercrosslinked aryl-rich starch-β-cyclodextrin polymeric sorbent

Zhongwei Tan¹, Xingguo Xu¹, Yu Wan¹, Chengjun Kang², Zhaoqiang Zhang², Zhenxia Zhao¹, Fang Shen¹, Kungang Chai¹, Hongbing Ji^1,3

1. School of Chemistry and Chemical Engineering, Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, Guangxi University, Nanning 530004, China;
2. Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore 117585, Singapore;
3. Fine Chemical Industry Research Institute, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China

Received:2022-02-13 Revised:2022-04-21 Online:2022-10-19
Contact: Zhaoqiang Zhang,E-mail:chezzh@nus.edu.sg;Kungang Chai,E-mail:chaikungang@gxu.edu.cn;Hongbing Ji,E-mail:jihb@mail.sysu.edu.cn
Supported by:
This work was supported by National Natural Science Foundation of China (21868002 and 21961160741), the Natural Science Foundation of Guangxi Province (2018GXNSFAA281206, 2020GXNSFGA297001, 2020GXNSFAA297044), Dean Project of Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (2021Z010), Specific research project of Guangxi for research bases and talents (AD18126005), special funding for ‘Guangxi Bagui Scholars’, Guangxi scholarship fund for the middle-aged backbone teachers.

Efficient recovery of aromatic compounds from the wastewater of styrene monomer and propylene oxide co-production plant via hypercrosslinked aryl-rich starch-β-cyclodextrin polymeric sorbent

Zhongwei Tan¹, Xingguo Xu¹, Yu Wan¹, Chengjun Kang², Zhaoqiang Zhang², Zhenxia Zhao¹, Fang Shen¹, Kungang Chai¹, Hongbing Ji^1,3

1. School of Chemistry and Chemical Engineering, Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, Guangxi University, Nanning 530004, China;
2. Department of Chemical and Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore 117585, Singapore;
3. Fine Chemical Industry Research Institute, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China

通讯作者: Zhaoqiang Zhang,E-mail:chezzh@nus.edu.sg;Kungang Chai,E-mail:chaikungang@gxu.edu.cn;Hongbing Ji,E-mail:jihb@mail.sysu.edu.cn
基金资助:
This work was supported by National Natural Science Foundation of China (21868002 and 21961160741), the Natural Science Foundation of Guangxi Province (2018GXNSFAA281206, 2020GXNSFGA297001, 2020GXNSFAA297044), Dean Project of Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (2021Z010), Specific research project of Guangxi for research bases and talents (AD18126005), special funding for ‘Guangxi Bagui Scholars’, Guangxi scholarship fund for the middle-aged backbone teachers.

Abstract

Abstract: Adsorptive recovery of valuable components from industrial wastewater is highly desirable for avoiding resource wastage but remains a challenge. Herein, we develop an efficient continuous adsorption process for recovering aromatic compounds in wastewater from styrene monomer and propylene oxide co-production (SMPO) plant. Based on our insight into the potential of bio-based porous materials for adsorption application, starch-graft-polystyrene (SPS) and aryl-modified β-cyclodextrin (ACD) were prepared, and novel hypercrosslinked porous polymers combined SPS with ACD (HSPS-ACDs) were synthesized through external crosslinking approach. In a binary-component system, the best-performing one HSPS-ACD(H) with high ACD content and large specific surface area possessed superior capacities for the representative aromatic compounds, acetophenone (AP, 2.81 mmol·g^-1) and 1-phenylethanol (1-PE, 1.35 mmol·g^-1) compared with the previously reported materials. Further, the adsorption properties of aromatic compounds on HSPS-ACD(H) were investigated in batch mode. For practical application, continuous adsorption experiments were conducted in a HSPS-ACD(H)-packed fixed bed, where the target aromatic components in wastewater were effectively retained and further released by elution. Besides showing the reversible adsorption and efficient enrichment effect, the HSPS-ACD(H)-packed fixed bed also maintained great stability in multiple cycles. Moreover, quantum chemical calculations were performed to elucidate the potential mechanism of adsorption of AP and 1-PE onto HSPS-ACD(H).

Key words: Adsorption, Wastewater treatment, Aromatics, Hypercrosslinked polymer, β-cyclodextrin, Starch

摘要： Adsorptive recovery of valuable components from industrial wastewater is highly desirable for avoiding resource wastage but remains a challenge. Herein, we develop an efficient continuous adsorption process for recovering aromatic compounds in wastewater from styrene monomer and propylene oxide co-production (SMPO) plant. Based on our insight into the potential of bio-based porous materials for adsorption application, starch-graft-polystyrene (SPS) and aryl-modified β-cyclodextrin (ACD) were prepared, and novel hypercrosslinked porous polymers combined SPS with ACD (HSPS-ACDs) were synthesized through external crosslinking approach. In a binary-component system, the best-performing one HSPS-ACD(H) with high ACD content and large specific surface area possessed superior capacities for the representative aromatic compounds, acetophenone (AP, 2.81 mmol·g^-1) and 1-phenylethanol (1-PE, 1.35 mmol·g^-1) compared with the previously reported materials. Further, the adsorption properties of aromatic compounds on HSPS-ACD(H) were investigated in batch mode. For practical application, continuous adsorption experiments were conducted in a HSPS-ACD(H)-packed fixed bed, where the target aromatic components in wastewater were effectively retained and further released by elution. Besides showing the reversible adsorption and efficient enrichment effect, the HSPS-ACD(H)-packed fixed bed also maintained great stability in multiple cycles. Moreover, quantum chemical calculations were performed to elucidate the potential mechanism of adsorption of AP and 1-PE onto HSPS-ACD(H).

关键词: Adsorption, Wastewater treatment, Aromatics, Hypercrosslinked polymer, β-cyclodextrin, Starch

Zhongwei Tan, Xingguo Xu, Yu Wan, Chengjun Kang, Zhaoqiang Zhang, Zhenxia Zhao, Fang Shen, Kungang Chai, Hongbing Ji. Efficient recovery of aromatic compounds from the wastewater of styrene monomer and propylene oxide co-production plant via hypercrosslinked aryl-rich starch-β-cyclodextrin polymeric sorbent[J]. Chinese Journal of Chemical Engineering, 2022, 49(9): 150-160.

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Efficient recovery of aromatic compounds from the wastewater of styrene monomer and propylene oxide co-production plant via hypercrosslinked aryl-rich starch-β-cyclodextrin polymeric sorbent

Efficient recovery of aromatic compounds from the wastewater of styrene monomer and propylene oxide co-production plant via hypercrosslinked aryl-rich starch-β-cyclodextrin polymeric sorbent

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