氨基功能化介孔超分子聚合物的温和构筑及其CO2吸附性能

doi:10.16085/j.issn.1000-6613.2021-2535

化工进展 ›› 2022, Vol. 41 ›› Issue (10): 5510-5517.DOI: 10.16085/j.issn.1000-6613.2021-2535

氨基功能化介孔超分子聚合物的温和构筑及其CO₂吸附性能

邱明月¹^,²(), 李东娜²(), 刘书磊², 易群¹, 范海明³, 李向远⁴, 李剑川⁴, 史利娟¹^,²^,⁴(), 张鼎¹

^1.武汉工程大学化工与制药学院，湖北武汉 430205
^2.太原理工大学省部共建煤基能源清洁高效利用国家重点实验室，山西太原 030024
^3.中国石油大学(华东)山东省油田化学重点实验室，山东青岛 266580
^4.天脊煤化工集团股份有限公司，山西长治 046000

收稿日期:2021-12-13 修回日期:2022-02-24 出版日期:2022-10-20 发布日期:2022-10-21
通讯作者: 史利娟
作者简介:邱明月（1996—），女，硕士研究生，研究方向为绿色化学。E-mail：qmy112616@163.com
李东娜（1994—），女，硕士研究生，研究方向为绿色化学。E-mail：1746647622@qq.com。
基金资助:
国家自然科学基金(U1810125);山西省自然科学基金面上基金(201901D111082);山东省油田化学重点实验室开放基金;中央高校基本科研业务费专项资金(19CX05006A)

Facile construction of amino-functionalized mesoporous supramolecular polymers for CO₂ adsorption

QIU Mingyue¹^,²(), LI Dongna²(), LIU shulei², YI Qun¹, FAN Haiming³, LI Xiangyuan⁴, LI Jianchuan⁴, SHI Lijuan¹^,²^,⁴(), ZHANG Ding¹

^1.School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430205, Hubei, China
^2.State Key Laboratory of Clean and Efficient Utilization of Coal-based Energy, Taiyuan University of Technology, Taiyuan 030024, Shanxi, China
^3.Shandong Key Laboratory of Oilfield Chemistry, China University of Petroleum (East China), Qingdao 266580, Shandong, China
^4.Shanxi Tianji Coal Chemical Company Limited, Changzhi 046000, Shanxi, China

Received:2021-12-13 Revised:2022-02-24 Online:2022-10-20 Published:2022-10-21
Contact: SHI Lijuan

摘要/Abstract

摘要：

以3,3'-二硫代双(丙酰肼)和对苯二甲醛为组装基元，通过动态共价键采用界面组装法在常温常压下温和构筑了具有丰富CO₂吸附位点的介孔超分子聚合物PDP。利用动态共价键的动态可逆性，通过合成后修饰法将两种具有丰富氨基位点的化合物（聚乙烯亚胺及四乙烯五胺）组装于PDP结构上，构建了两种氨基功能化超分子聚合物材料PDPP和PDPT。相较于PDP，修饰后超分子聚合物CO₂吸附性能有了极大提升，PDPT在80℃下CO₂吸附量可达27.79cm³/g。动态亚胺组装策略具有制备条件温和、结构功能可控等特性，为开发CO₂高吸附性能材料提供了全新思路。

关键词: 界面组装, 合成后修饰, 亚胺交换, 二氧化碳吸附, 聚乙烯亚胺, 四乙烯五胺

Abstract:

A series of mesoporous supramolecular polymers (PDP) with abundant CO₂ adsorption sites were constructed through the interfacial assembly of 3,3'-dithiobenzide and p-benzaldehyde at room temperature and ambient pressure. Two kinds of amino-functionalized supramolecular polymers (PDPP and PDPT) were constructed by using imine exchange with polyethylene imine and tetraethylene pentamine. Compared to PDP, the CO₂ adsorption ability of the modified supramolecular polymers was greatly improved. The CO₂ adsorption capacity of PDPT can reach 27.79cm³/g at 80℃. This dynamic imine assembly strategy provided a mild and controllable approach for the development of materials with high CO₂ adsorption performance.

Key words: interfacial assembly, post-synthetic modification, imine exchange, carbon dioxide adsorption, polyethyleneimine, tetraethylene pentamine

中图分类号:

TQ317.4

邱明月, 李东娜, 刘书磊, 易群, 范海明, 李向远, 李剑川, 史利娟, 张鼎. 氨基功能化介孔超分子聚合物的温和构筑及其CO₂吸附性能[J]. 化工进展, 2022, 41(10): 5510-5517.

QIU Mingyue, LI Dongna, LIU shulei, YI Qun, FAN Haiming, LI Xiangyuan, LI Jianchuan, SHI Lijuan, ZHANG Ding. Facile construction of amino-functionalized mesoporous supramolecular polymers for CO₂ adsorption[J]. Chemical Industry and Engineering Progress, 2022, 41(10): 5510-5517.

图/表 13

图1 合成示意图(1) 3,3'-二硫代双(丙酰肼) 的构筑反应式；(2) 超分子聚合物PDP的构筑反应式

图2 3,3'-二硫代双(丙酰肼)的氢谱核磁

图3 亚胺交换的胺分子结构式

图4 CO2动态吸附装置1—钢瓶；2—压力计；3—安全阀；4—流量计；5—三通；6—混合槽；7—样品柱；8—恒温器；9—气体分析仪

图5 DTP、PA、PDP、PDPP及PDPT的红外谱图（因受到仪器信号强度影响，不同样品对应的红外谱图峰强度不太一致，故谱图强度PDP-3、PDPP和PDPT同比例乘1.5倍，使C̿ N双键峰强度基本一致）

图6 PDP、PDPP及PDPT的SEM图

图7 PDP、PDPP和PDPT的XRD谱图

图8 PDP、PDPP及PDPT的N2吸脱附曲线及孔径分布曲线

表1 PDP、PDPP及PDPT的比表面积及孔容

样品	BET比表面积^①/m²·g^-1	微孔比表面积^②/m²·g^-1	总孔体积^③/cm³·g^-1	介孔体积^⑤/cm³·g^-1
PDP-1	72.57	0.00	0.27	0.27
PDP-2	77.91	0.00	0.36	0.36
PDP-3	58.20	0.00	0.28	0.28
PDPP	37.27	0.23	0.19	0.19
PDPT	23.12	0.00	0.14	0.14

图9 热重及同步热分析曲线

图10 CO2吸附性能

图11 PDP和PDPT在80℃、不同CO2占比条件下CO2吸附量

表2 CO2吸附性能文献汇总表

载体类型	负载胺类	胺负载量（质量分数）/%	CO₂吸附条件	CO₂吸附量/cm³∙g^-1	参考文献
超分子聚合物	TEPA	18.23	80℃，1bar	27.79	—
AOMC	PEI	60.00	75℃，1bar	24.41	［40］
MWCNT	PEI	16.00	70℃，0.2bar	21.95	［42］
13X分子筛	MEA	50.00	75℃，0.15bar	18.37	［43］
SBA-15(p)-AP-70T	TEPA	70	75℃，0.1bar	127.46	［44］
SBA15-P	PEI	17.70	25℃，0.1bar	14.78	［45］

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氨基功能化介孔超分子聚合物的温和构筑及其CO₂吸附性能

Facile construction of amino-functionalized mesoporous supramolecular polymers for CO₂ adsorption

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