• •
收稿日期:
2024-03-14
修回日期:
2024-06-06
出版日期:
2024-07-11
通讯作者:
朱佳媚
作者简介:
赵非凡(2001—),男,硕士研究生,zhaofeifan135@163.com
基金资助:
Feifan ZHAO(), Jiamei ZHU(
), Jie KANG, Liang TAN, Jingyu DUAN
Received:
2024-03-14
Revised:
2024-06-06
Online:
2024-07-11
Contact:
Jiamei ZHU
摘要:
为拓展和探究离子液体在挥发性有机物(VOCs)吸收领域的潜在应用和机理分析,以乙醚、丙酮和二氯甲烷为VOCs代表,模拟计算了三种季鏻类离子液体(PILs),即三丁基(丙基)季鏻四氟硼酸盐([P4443][BF4])、三丁基(丙基)季鏻双三氟甲基磺酰亚胺盐([P4443][Tf2N])、三丁基(丙基)季鏻三氟乙酸盐([P4443][CF3COO])吸收单分子和多分子VOCs的活性位点、氢键、吸收能(Eabs)、电荷等。研究表明,PILs与三种VOCs之间形成了氢键并伴随电荷转移,阴离子对乙醚和丙酮吸收影响不显著;阴离子对二氯甲烷的吸收则起主要作用,[CF3COO]-的Eabs值明显较大。[P4443]+类离子对一般具有3个类似的吸收活性位点,其容纳VOCs分子的空间主要由阳离子提供。离子液体的双离子对空间结构分析表明,其中碱性弱、且体积较大阴离子组成的PILs更容易暴露其吸收位点。实验研究进一步表明,相比咪唑类离子液体,PILs表现出优异的VOCs吸收能力。
中图分类号:
赵非凡, 朱佳媚, 康洁, 檀亮, 段靖瑜. 三丁基(丙基)季鏻离子液体对VOCs的吸附性能及机理[J]. 化工学报, DOI: 10.11949/0438-1157.20240296.
Feifan ZHAO, Jiamei ZHU, Jie KANG, Liang TAN, Jingyu DUAN. Absorption characteristics and mechanism of VOCs by tributyl(propyl)phosphonium ionic liquid[J]. CIESC Journal, DOI: 10.11949/0438-1157.20240296.
构型 | [P4443]+ | [BF4]- | [Tf2N]- | [CF3COO]- | 1-乙醚 | 2-乙醚 | 3-乙醚 |
---|---|---|---|---|---|---|---|
[P4443][BF4] | 0.898 | -0.9 | - | - | - | - | - |
[P4443][BF4]∙DEE | 0.89 | -0.902 | - | - | 0.009 | - | - |
[P4443][BF4]∙2DEE | 0.887 | -0.893 | - | - | 0.010 | -0.007 | - |
[P4443][BF4]∙3DEE | 0.882 | -0.891 | - | - | 0.008 | -0.004 | 0.005 |
[P4443][Tf2N] | 0.928 | - | -0.930 | - | - | - | - |
[P4443][Tf2N]∙DEE | 0.913 | - | -0.924 | - | 0.013 | - | - |
[P4443][Tf2N]∙2DEE | 0.912 | - | -0.931 | - | 0.009 | 0.009 | - |
[P4443][Tf2N]∙3DEE | 0.901 | - | -0.930 | - | 0.009 | 0.010 | 0.009 |
[P4443][CF3COO] | 0.832 | - | - | -0.831 | - | - | - |
[P4443][CF3COO]∙DEE | 0.826 | - | - | -0.833 | 0.007 | - | - |
[P4443][CF3COO]∙2DEE | 0.828 | - | - | -0.833 | 0.002 | 0.006 | - |
[P4443][CF3COO]∙3DEE | 0.842 | - | - | -0.834 | 0.002 | 0.003 | -0.011 |
表1 PILs与PIL∙nDEE中阴阳离子和被吸收乙醚的Mulliken电荷(e)总和
Table 1 The sum of Mulliken charge (in e) of cations, anions and the absorbed ether in PILs and PIL∙nDEE
构型 | [P4443]+ | [BF4]- | [Tf2N]- | [CF3COO]- | 1-乙醚 | 2-乙醚 | 3-乙醚 |
---|---|---|---|---|---|---|---|
[P4443][BF4] | 0.898 | -0.9 | - | - | - | - | - |
[P4443][BF4]∙DEE | 0.89 | -0.902 | - | - | 0.009 | - | - |
[P4443][BF4]∙2DEE | 0.887 | -0.893 | - | - | 0.010 | -0.007 | - |
[P4443][BF4]∙3DEE | 0.882 | -0.891 | - | - | 0.008 | -0.004 | 0.005 |
[P4443][Tf2N] | 0.928 | - | -0.930 | - | - | - | - |
[P4443][Tf2N]∙DEE | 0.913 | - | -0.924 | - | 0.013 | - | - |
[P4443][Tf2N]∙2DEE | 0.912 | - | -0.931 | - | 0.009 | 0.009 | - |
[P4443][Tf2N]∙3DEE | 0.901 | - | -0.930 | - | 0.009 | 0.010 | 0.009 |
[P4443][CF3COO] | 0.832 | - | - | -0.831 | - | - | - |
[P4443][CF3COO]∙DEE | 0.826 | - | - | -0.833 | 0.007 | - | - |
[P4443][CF3COO]∙2DEE | 0.828 | - | - | -0.833 | 0.002 | 0.006 | - |
[P4443][CF3COO]∙3DEE | 0.842 | - | - | -0.834 | 0.002 | 0.003 | -0.011 |
构型 | [P4443]+ | [BF4]- | [Tf2N]- | [CF3COO]- | 1-丙酮 | 2-丙酮 | 3-丙酮 |
---|---|---|---|---|---|---|---|
[P4443][BF4]∙DMK | 0.890 | -0.897 | - | - | 0.006 | - | - |
[P4443][BF4]∙2DMK | 0.888 | -0.896 | - | - | 0.005 | 0.006 | - |
[P4443][BF4]∙3DMK | 0.887 | -0.879 | - | - | -0.002 | -0.001 | -0.003 |
[P4443][Tf2N]∙DMK | 0.913 | -0.926 | 0.011 | - | - | ||
[P4443][Tf2N]∙2DMK | 0.917 | - | -0.928 | - | 0.005 | 0.009 | - |
[P4443][Tf2N]∙3DMK | 0.912 | - | -0.928 | - | 0.009 | 0.009 | -0.001 |
[P4443][CF3COO]∙DMK | 0.849 | - | - | -0.845 | -0.007 | - | - |
[P4443][CF3COO]∙2DMK | 0.864 | - | - | -0.848 | -0.006 | -0.010 | - |
[P4443][CF3COO]∙3DMK | 0.866 | - | - | -0.847 | -0.006 | -0.007 | -0.006 |
表2 PILs 与 PIL∙nDMK中阴阳离子和被吸收丙酮的Mulliken电荷(e)总和
Table 2 The sum of Mulliken charge (in e) of cations, anions and the absorbed acetone in PILs and PIL∙nDMK
构型 | [P4443]+ | [BF4]- | [Tf2N]- | [CF3COO]- | 1-丙酮 | 2-丙酮 | 3-丙酮 |
---|---|---|---|---|---|---|---|
[P4443][BF4]∙DMK | 0.890 | -0.897 | - | - | 0.006 | - | - |
[P4443][BF4]∙2DMK | 0.888 | -0.896 | - | - | 0.005 | 0.006 | - |
[P4443][BF4]∙3DMK | 0.887 | -0.879 | - | - | -0.002 | -0.001 | -0.003 |
[P4443][Tf2N]∙DMK | 0.913 | -0.926 | 0.011 | - | - | ||
[P4443][Tf2N]∙2DMK | 0.917 | - | -0.928 | - | 0.005 | 0.009 | - |
[P4443][Tf2N]∙3DMK | 0.912 | - | -0.928 | - | 0.009 | 0.009 | -0.001 |
[P4443][CF3COO]∙DMK | 0.849 | - | - | -0.845 | -0.007 | - | - |
[P4443][CF3COO]∙2DMK | 0.864 | - | - | -0.848 | -0.006 | -0.010 | - |
[P4443][CF3COO]∙3DMK | 0.866 | - | - | -0.847 | -0.006 | -0.007 | -0.006 |
构型 | [P4443]+ | [BF4]- | [Tf2N]- | [CF3COO]- | 1-二氯甲烷 | 2-二氯甲烷 | 3-二氯甲烷 |
---|---|---|---|---|---|---|---|
[P4443][BF4]∙DCM | 0.895 | -0.891 | - | - | -0.003 | - | - |
[P4443][BF4]∙2DCM | 0.902 | -0.889 | - | - | -0.003 | -0.008 | - |
[P4443][BF4]∙3DCM | 0.893 | -0.885 | - | - | 0.000 | -0.006 | -0.001 |
[P4443][Tf2N]∙DCM | 0.908 | - | -0.915 | - | 0.006 | - | - |
[P4443][Tf2N]∙2DCM | 0.910 | - | -0.908 | - | 0.000 | -0.003 | - |
[P4443][Tf2N]∙3DCM | 0.901 | - | -0.905 | - | 0.002 | -0.005 | -0.001 |
[P4443][CF3COO]∙DCM | 0.837 | - | - | -0.827 | -0.014 | - | - |
[P4443][CF3COO]∙2DCM | 0.840 | - | - | -0.823 | -0.012 | -0.008 | - |
[P4443][CF3COO]∙3DCM | 0.847 | - | - | -0.828 | -0.006 | -0.009 | -0.005 |
表3 PILs与PIL∙nDCM中阴阳离子和被吸收二氯甲烷的Mulliken电荷(e)总和
Table 3 The sum of Mulliken charge (in e) of cations, anions and the absorbed dichloromethane in PILs and PIL∙nDCM
构型 | [P4443]+ | [BF4]- | [Tf2N]- | [CF3COO]- | 1-二氯甲烷 | 2-二氯甲烷 | 3-二氯甲烷 |
---|---|---|---|---|---|---|---|
[P4443][BF4]∙DCM | 0.895 | -0.891 | - | - | -0.003 | - | - |
[P4443][BF4]∙2DCM | 0.902 | -0.889 | - | - | -0.003 | -0.008 | - |
[P4443][BF4]∙3DCM | 0.893 | -0.885 | - | - | 0.000 | -0.006 | -0.001 |
[P4443][Tf2N]∙DCM | 0.908 | - | -0.915 | - | 0.006 | - | - |
[P4443][Tf2N]∙2DCM | 0.910 | - | -0.908 | - | 0.000 | -0.003 | - |
[P4443][Tf2N]∙3DCM | 0.901 | - | -0.905 | - | 0.002 | -0.005 | -0.001 |
[P4443][CF3COO]∙DCM | 0.837 | - | - | -0.827 | -0.014 | - | - |
[P4443][CF3COO]∙2DCM | 0.840 | - | - | -0.823 | -0.012 | -0.008 | - |
[P4443][CF3COO]∙3DCM | 0.847 | - | - | -0.828 | -0.006 | -0.009 | -0.005 |
图9 最稳定的(a) 2[P4443][BF4], (b) 2[P4443][Tf2N]和(c) 2[P4443][CF3COO]
Fig. 9 The most stable (a) 2[P4443][BF4], (b) 2[P4443][Tf2N] and (c) 2[P4443][CF3COO]
离子液体 | 乙醚吸收量 (g/g) | 丙酮吸收量 (g/g) | 二氯甲烷 吸收量(g/g) | 测试条件 | 来源 |
---|---|---|---|---|---|
[P4443][BF4] | 0.5644 | 1.5615 | 1.774 | 25 ℃, 50 kPa | 本文 |
[P4443][Tf2N] | 0.7123 | 1.5773 | 1.239 | 25 ℃, 50 kPa | 本文 |
[P4443][CF3COO] | 0.7378 | 1.5272 | 2.510 | 25 ℃, 50 kPa | 本文 |
[BMIM][BF4] | 0.2345 | 1.5484 | 0.956 | 25 ℃, 50 kPa | 本文 |
[BMIM][SCN] | - | - | 0.85 | 30 ℃, 50 kPa | [ |
[BMIM][Tf2N] | - | - | 0.38 | 30 ℃, 50 kPa | [ |
[OMIM][BF4] | - | - | 0.89 | 30 ℃, 50 kPa | [ |
[EMIM][CF3COO] | - | - | 1.047 | 30 ℃,0.03 MPa | [ |
表4 与参考文献对比分析离子液体的VOCs静态吸收容量
Table 4 Static absorption capacity of ionic liquids for VOCs compared with references
离子液体 | 乙醚吸收量 (g/g) | 丙酮吸收量 (g/g) | 二氯甲烷 吸收量(g/g) | 测试条件 | 来源 |
---|---|---|---|---|---|
[P4443][BF4] | 0.5644 | 1.5615 | 1.774 | 25 ℃, 50 kPa | 本文 |
[P4443][Tf2N] | 0.7123 | 1.5773 | 1.239 | 25 ℃, 50 kPa | 本文 |
[P4443][CF3COO] | 0.7378 | 1.5272 | 2.510 | 25 ℃, 50 kPa | 本文 |
[BMIM][BF4] | 0.2345 | 1.5484 | 0.956 | 25 ℃, 50 kPa | 本文 |
[BMIM][SCN] | - | - | 0.85 | 30 ℃, 50 kPa | [ |
[BMIM][Tf2N] | - | - | 0.38 | 30 ℃, 50 kPa | [ |
[OMIM][BF4] | - | - | 0.89 | 30 ℃, 50 kPa | [ |
[EMIM][CF3COO] | - | - | 1.047 | 30 ℃,0.03 MPa | [ |
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