离子液体在超声辅助—铁炭微电解体系中的降解与机理研究
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摘要
离子液体是近年迅速发展起来的新型介质和功能材料,因其几乎无蒸汽压,热稳定性高、液态范围宽、且具有良好的溶解能力和电化学性能,被广泛关注,成为可设计的绿色材料,并成功应用于化学合成与催化、萃取分离、能源、材料和电化学领域。然而,已有研究表明,许多常用的离子液体是有毒的,且难以生物降解,因此,探讨离子液体有效的化学去除方法非常必要。本文尝试采用超声辅助-零价铁/活性炭(US-ZVI/AC)微电解方法降解常用离子液体,在对实验条件进行优化的基础上,用UV、HPLC、HPLC-MS和GC-MS等技术研究了具有不同烷基侧链的咪唑离子液体、不同头基类型的离子液体以及某些功能性离子液体的降解过程和降解产物,提出了可能的降解途径。主要内容包括：
(1)以氯化1-丁基-3-甲基咪唑([C4mim]Cl]离子液体为代表,研究了US-ZVI/AC降解离子液体的效果。通过改变炭铁比、炭铁用量、pH值等观察离子液体的降解情况,利用HPLC、UV扫描法分析反应过程,通过测定离子液体降解前后的总有机碳(TOC)观察降解效果。结果表明：铁炭微电解法降解[C4mim]Cl的最佳条件为：炭铁比为2：1,用量为活性炭6g·L-1、零价铁3g·L-1,样品pH=3,45KHz的超声辅助能够大大提高[C4mim]Cl的降解效率；[C4mim]Cl的降解过程遵从准一级反应动力学规律；过量·OH清除剂的存在可以明显降低降解反应速率,但不能阻止降解反应的发生,说明·OH只是降解反应中起重要作用的活性组分之一。在降解110min时咪唑环的UV吸收带基本消失,[C4mim]Cl的降解率为95%以上,TOC去除率达到81.2%。
(2)改变1-烷基-3-甲基咪唑类离子液体中阳离子的烷基链长,或改变[C4mim]Cl中的阴离子,研究了咪唑类离子液体的降解率与其结构的关系；用GC-MS和HPLC-MS分析了1-烷基-3-甲基咪唑阳离子不同反应时间降解的中间产物,推测了降解机理。结果表明：在US-ZVI/AC微电解体系中,所研究的咪唑离子液体均能快速有效地降解；不同阴离子对1-丁基-3-甲基咪唑离子液体的降解速率和降解率无影响,而不同侧链的咪唑离子液体[Cnmim]Br(n=2,4,6,8,10)的降解速率稍有差异,即不同的烷基链长对降解的影响较小,降解反应遵从准一级反应动力学规律；在降解过程中,[Cnmim]+咪唑环上的3H,4H,5H先被氧化生成1-烷基-3-甲基-2,4,5-三氧咪唑,然后咪唑开环生成1-烷基-3-甲基脲,再分解生成N-烷基甲酰胺。在此过程中,81%以上的TOC被去除,说明降解产物N-烷基甲酰胺还可以进一步矿化。
(3)分析了不同头基类型的离子液体在US-ZVI/AC微电解体系中降解的中间产物,推测其降解机理。结果显示,在US-ZVI/AC微电解体系中,溴化1-丁基-1-甲基哌啶([C4mpip]Br)、溴化1-丁基-1-甲基吡咯([C4mpyr]Br)和溴化N-丁基-N-甲基吗啉([C4mmor]Br)也能有效降解,其降解效率与离子液体的头基类型有较大关系。与咪唑离子液体不同的是,[C4mpip]Br、[C4mpyr]Br和[C4mmor]Br的氧化降解发生在侧链上,丁基侧链氧化成醇,而后又顺序氧化依次生成了醛和羧酸,然后与杂环脱离,生成了N-甲基杂环化合物。三种离子液体的TOC去除率在69.6-73.8%之间,说明鉴定的最终产物N-甲基杂环化合物同样可以发生进一步的矿化。
(4)研究了功能离子液体氯化1-烯丙基-3-甲基咪唑([Amim]Cl)、溴化1-丁基-3-甲基苯并咪唑([Bmbim]Br)和四丁基氯化铵([Tba]Cl)在US-ZVI/AC微电解体系中的降解。结果表明,这些功能离子液体在US-ZVI/AC微电解体系中同样可以有效地降解,其中[Amim]Cl的降解途径与前述咪唑离子液体阳离子的降解途径相似,即[Amim]Cl的咪唑环先氧化后开环,生成脲或甲酰胺；[Bmbim]Br降解时,先发生咪唑环中2位C上的氧化,而后侧链断裂或咪唑开环,由于苯环的引入,导致降解过程与前述咪唑类离子液体的差异；[Tba]Cl的降解则通过逐步去除丁基来实现。三种离子液体的TOC去除率在82%以上,证明检出的降解产物均可发生进一步的分解、矿化,在US-ZVI/AC微电解体系中降解的效果非常显著。
在US-ZVI/AC微电解系统中,高的降解率和TOC去除率说明,这是一种卓有成效且环境友好的离子液体去除方法。本文的研究成果对于消除离子液体的环境影响、评价常用离子液体的环境行为具有重要的指导意义。
Ionic liquids (ILs), as novel media and functional materials, are developing rapidly in recent years due to their attracted properties such as negligible vapor pressure, high thermal stability, extended liquid-state temperature range, good dissolving ability and electrochemical properties. Regarded as green solvents and materials, ILs have been successfully used in chemical synthesis and catalysis, extraction and separation, energy materials and electrochemistry. However, it has been reported that the commonly used ILs are toxic and not biodegradable in nature, thus development of efficient chemical methods for the degradation of ILs is imperative. In this work, an ultrasonic irradiation and zero-valent iron activated carbon (US-ZVI/AC) micro-electrolysis system was applied to degradation of ionic liquid residues in water. The experimental conditions were optimized, and the degradation processes of imidazolium ILs with different alkyl side chains, ILs with different head group types and some functionalized ionic liquids were investigated, and some intermediates generated during the degradation were identified. On the basis of these observations, the degradation pathways were suggested. The main contents are as follows.
(1)1-Butyl-3-methylimidazolium chloride ([C4mim]Cl), a widely used ionic liquid, was chosen as a model ionic liquid to study the degradation efficiency of ionic liquids in US-ZVI/AC system. The degradation efficiency of [C4mim]Cl was investigated by changing AC/ZVI ratio, dosages of AC and ZVI, solution pH and so on. The degradation processes were analyzed by using UV and HPLC techniques and the degradation efficiency was observed by determination of TOC. It was shown that the optimized experimental conditions for [C4mim]Cl degradation were: AC/ZVI ratio of2:1, the AC dosage of6g·L-1, the ZVI dosage of3g·L-1, and solution pH value of3. The degradation efficiency of [C4mim]Cl could be improved greatly by ultrasonic irradiation frequency of45KHz, and the degradation could be described by a pseudo-first-order kinetics. The presence of excess hydroxyl radical scavenger could greatly reduce the reaction rate but could not prevent degradation of [C4mim]Cl, and the results confirmed that OH· participated in the reaction process and played an important role, but it was not the only reactive species involved in the degradation of [C4mim]Cl. The ultraviolet absorption band of [C4mim]Cl at212nm disappeared almost completely, and more than95%of [C4mim]C1could be degraded in aqueous solution and81.2%of [C4mim]Cl could be mineralized within110min.
(2) The relationship between the degradation degree and the chemical structure of ionic liquids was investigated by changing the length of alkyl chain in1-alkyl-3-methylimidazolium bromide ([Cnmim]Br, n=2,4,6,8,10) and the counter ion type of1-butyl-3-methylimidazolium cation ([C4mim]+). The degradation intermediates of [Cnmim]+at different reaction time were analyzed by GC-MS and HPLC-MS, and the degradation pathway was suggested. It was shown that the imidazolium ILs studied here can be degraded rapidly in US-ZVI/AC system, and the degradation of imidazolium ILs was not influenced by the type of counter anion but can be less influenced by their alkyl chain length. The degradation of [Cnmim]Br followed the pseudo-first-order kinetics model with respect to its concentration. In the degradation processes, the2,4,5positioned H atoms of1-alkyl-3-methylimidazolium ring were first oxidized to generate1-alkyl-3-methyl-2,4,5-trioxoimidazolidine, and then the ring was opened to form1-alkyl-3-methylurea which was further decomposed to form N-alkylformamide. More than81%of TOC removal of [Cnmim]Br suggested further mineralization of the N-alkylformamide.
(3) The degradation of the ILs with different head group types was investigated in US-ZVI/AC system and their degradation intermediates were identified by GC-MS and HPLC-MS in the same way mentioned above, and the degradation pathways were then suggested. The results showed that1-butyl-1-methylpiperidinium bromide ([C4mpip]Br),1-butyl-1-methylpyrrolidinium bromide ([C4mpyr]Br) and N-butyl-N-methylmorpholinium bromide ([C4mmor]Br) were also effectively degraded in the system, and the level of degradation is dependent on the type of cationic head group of the ILs. Unlike the imidazolium ILs discussed above, oxidation degradation of [C4mpip]Br,[C4mpyr]Br and [C4mmor]Br in the micro-electrolysis system was observed at the N-butyl side chains. The alcohols formed by oxidation were subsequently oxidized via aldehydes to carboxylic acids. N-methyl heterocyclic core was generated via the elimination of the oxidized butyl side chain. The TOC removal of these ILs was in the range of69.6-73.8%and this indicated partial mineralization of N-methyl heterocyclic core.
(4) Degradation of the functionalized ionic liquids1-allyl-3-methylimidazolium chloride ([Amim]Cl), N-butyl, methyl benzimidazolium bromide ([Bmbim]Br) and tetrabutyl ammonium chloride ([Tba]Cl) was investigated in US-ZVI/AC micro-electrolysis system. The degradation degree and intermediates were analyzed and degradation mechanisms were presumed. It is shown that the three functionalized ILs could also be effectively degraded and the degradation pathway of [Amim]Cl was similar to that of the imidazolium ILs discussed above: the imidazolium ring of [Amim]C1was first oxidized and then the ring was opened to form urea or formamide. The degradation of [Bmbim]Br was started by the oxidization of2-positioned C atom of the imidazolium ring, and then the alkyl side chain was broken or the imidazolium ring was opened. The difference in degradation pathway is probably caused by the presence of benzene ring. The degradation of [Tba]Cl was carried out through the gradual elimination of butyl groups. The TOC removal of the three ILs was greater than82%, which indicated the further mineralization of the degradation products identified and significant degradation effect of the ILs in the system.
The high degradation efficiency and TOC removal suggested that the ZVI/AC micro-electrolysis assisted by ultrasonic irradiation could serve as an efficient technology for the removal of ILs from aqueous solutions, and the degradation products are environmental friendly to a great extent. The results presented here may be useful for the assessment of the factors related to the environmental fate and environmental behavior of these commonly used ILs.
(1)以氯化1-丁基-3-甲基咪唑([C4mim]Cl]离子液体为代表,研究了US-ZVI/AC降解离子液体的效果。通过改变炭铁比、炭铁用量、pH值等观察离子液体的降解情况,利用HPLC、UV扫描法分析反应过程,通过测定离子液体降解前后的总有机碳(TOC)观察降解效果。结果表明：铁炭微电解法降解[C4mim]Cl的最佳条件为：炭铁比为2：1,用量为活性炭6g·L-1、零价铁3g·L-1,样品pH=3,45KHz的超声辅助能够大大提高[C4mim]Cl的降解效率；[C4mim]Cl的降解过程遵从准一级反应动力学规律；过量·OH清除剂的存在可以明显降低降解反应速率,但不能阻止降解反应的发生,说明·OH只是降解反应中起重要作用的活性组分之一。在降解110min时咪唑环的UV吸收带基本消失,[C4mim]Cl的降解率为95%以上,TOC去除率达到81.2%。
(2)改变1-烷基-3-甲基咪唑类离子液体中阳离子的烷基链长,或改变[C4mim]Cl中的阴离子,研究了咪唑类离子液体的降解率与其结构的关系；用GC-MS和HPLC-MS分析了1-烷基-3-甲基咪唑阳离子不同反应时间降解的中间产物,推测了降解机理。结果表明：在US-ZVI/AC微电解体系中,所研究的咪唑离子液体均能快速有效地降解；不同阴离子对1-丁基-3-甲基咪唑离子液体的降解速率和降解率无影响,而不同侧链的咪唑离子液体[Cnmim]Br(n=2,4,6,8,10)的降解速率稍有差异,即不同的烷基链长对降解的影响较小,降解反应遵从准一级反应动力学规律；在降解过程中,[Cnmim]+咪唑环上的3H,4H,5H先被氧化生成1-烷基-3-甲基-2,4,5-三氧咪唑,然后咪唑开环生成1-烷基-3-甲基脲,再分解生成N-烷基甲酰胺。在此过程中,81%以上的TOC被去除,说明降解产物N-烷基甲酰胺还可以进一步矿化。
(3)分析了不同头基类型的离子液体在US-ZVI/AC微电解体系中降解的中间产物,推测其降解机理。结果显示,在US-ZVI/AC微电解体系中,溴化1-丁基-1-甲基哌啶([C4mpip]Br)、溴化1-丁基-1-甲基吡咯([C4mpyr]Br)和溴化N-丁基-N-甲基吗啉([C4mmor]Br)也能有效降解,其降解效率与离子液体的头基类型有较大关系。与咪唑离子液体不同的是,[C4mpip]Br、[C4mpyr]Br和[C4mmor]Br的氧化降解发生在侧链上,丁基侧链氧化成醇,而后又顺序氧化依次生成了醛和羧酸,然后与杂环脱离,生成了N-甲基杂环化合物。三种离子液体的TOC去除率在69.6-73.8%之间,说明鉴定的最终产物N-甲基杂环化合物同样可以发生进一步的矿化。
(4)研究了功能离子液体氯化1-烯丙基-3-甲基咪唑([Amim]Cl)、溴化1-丁基-3-甲基苯并咪唑([Bmbim]Br)和四丁基氯化铵([Tba]Cl)在US-ZVI/AC微电解体系中的降解。结果表明,这些功能离子液体在US-ZVI/AC微电解体系中同样可以有效地降解,其中[Amim]Cl的降解途径与前述咪唑离子液体阳离子的降解途径相似,即[Amim]Cl的咪唑环先氧化后开环,生成脲或甲酰胺；[Bmbim]Br降解时,先发生咪唑环中2位C上的氧化,而后侧链断裂或咪唑开环,由于苯环的引入,导致降解过程与前述咪唑类离子液体的差异；[Tba]Cl的降解则通过逐步去除丁基来实现。三种离子液体的TOC去除率在82%以上,证明检出的降解产物均可发生进一步的分解、矿化,在US-ZVI/AC微电解体系中降解的效果非常显著。
在US-ZVI/AC微电解系统中,高的降解率和TOC去除率说明,这是一种卓有成效且环境友好的离子液体去除方法。本文的研究成果对于消除离子液体的环境影响、评价常用离子液体的环境行为具有重要的指导意义。
Ionic liquids (ILs), as novel media and functional materials, are developing rapidly in recent years due to their attracted properties such as negligible vapor pressure, high thermal stability, extended liquid-state temperature range, good dissolving ability and electrochemical properties. Regarded as green solvents and materials, ILs have been successfully used in chemical synthesis and catalysis, extraction and separation, energy materials and electrochemistry. However, it has been reported that the commonly used ILs are toxic and not biodegradable in nature, thus development of efficient chemical methods for the degradation of ILs is imperative. In this work, an ultrasonic irradiation and zero-valent iron activated carbon (US-ZVI/AC) micro-electrolysis system was applied to degradation of ionic liquid residues in water. The experimental conditions were optimized, and the degradation processes of imidazolium ILs with different alkyl side chains, ILs with different head group types and some functionalized ionic liquids were investigated, and some intermediates generated during the degradation were identified. On the basis of these observations, the degradation pathways were suggested. The main contents are as follows.
(1)1-Butyl-3-methylimidazolium chloride ([C4mim]Cl), a widely used ionic liquid, was chosen as a model ionic liquid to study the degradation efficiency of ionic liquids in US-ZVI/AC system. The degradation efficiency of [C4mim]Cl was investigated by changing AC/ZVI ratio, dosages of AC and ZVI, solution pH and so on. The degradation processes were analyzed by using UV and HPLC techniques and the degradation efficiency was observed by determination of TOC. It was shown that the optimized experimental conditions for [C4mim]Cl degradation were: AC/ZVI ratio of2:1, the AC dosage of6g·L-1, the ZVI dosage of3g·L-1, and solution pH value of3. The degradation efficiency of [C4mim]Cl could be improved greatly by ultrasonic irradiation frequency of45KHz, and the degradation could be described by a pseudo-first-order kinetics. The presence of excess hydroxyl radical scavenger could greatly reduce the reaction rate but could not prevent degradation of [C4mim]Cl, and the results confirmed that OH· participated in the reaction process and played an important role, but it was not the only reactive species involved in the degradation of [C4mim]Cl. The ultraviolet absorption band of [C4mim]Cl at212nm disappeared almost completely, and more than95%of [C4mim]C1could be degraded in aqueous solution and81.2%of [C4mim]Cl could be mineralized within110min.
(2) The relationship between the degradation degree and the chemical structure of ionic liquids was investigated by changing the length of alkyl chain in1-alkyl-3-methylimidazolium bromide ([Cnmim]Br, n=2,4,6,8,10) and the counter ion type of1-butyl-3-methylimidazolium cation ([C4mim]+). The degradation intermediates of [Cnmim]+at different reaction time were analyzed by GC-MS and HPLC-MS, and the degradation pathway was suggested. It was shown that the imidazolium ILs studied here can be degraded rapidly in US-ZVI/AC system, and the degradation of imidazolium ILs was not influenced by the type of counter anion but can be less influenced by their alkyl chain length. The degradation of [Cnmim]Br followed the pseudo-first-order kinetics model with respect to its concentration. In the degradation processes, the2,4,5positioned H atoms of1-alkyl-3-methylimidazolium ring were first oxidized to generate1-alkyl-3-methyl-2,4,5-trioxoimidazolidine, and then the ring was opened to form1-alkyl-3-methylurea which was further decomposed to form N-alkylformamide. More than81%of TOC removal of [Cnmim]Br suggested further mineralization of the N-alkylformamide.
(3) The degradation of the ILs with different head group types was investigated in US-ZVI/AC system and their degradation intermediates were identified by GC-MS and HPLC-MS in the same way mentioned above, and the degradation pathways were then suggested. The results showed that1-butyl-1-methylpiperidinium bromide ([C4mpip]Br),1-butyl-1-methylpyrrolidinium bromide ([C4mpyr]Br) and N-butyl-N-methylmorpholinium bromide ([C4mmor]Br) were also effectively degraded in the system, and the level of degradation is dependent on the type of cationic head group of the ILs. Unlike the imidazolium ILs discussed above, oxidation degradation of [C4mpip]Br,[C4mpyr]Br and [C4mmor]Br in the micro-electrolysis system was observed at the N-butyl side chains. The alcohols formed by oxidation were subsequently oxidized via aldehydes to carboxylic acids. N-methyl heterocyclic core was generated via the elimination of the oxidized butyl side chain. The TOC removal of these ILs was in the range of69.6-73.8%and this indicated partial mineralization of N-methyl heterocyclic core.
(4) Degradation of the functionalized ionic liquids1-allyl-3-methylimidazolium chloride ([Amim]Cl), N-butyl, methyl benzimidazolium bromide ([Bmbim]Br) and tetrabutyl ammonium chloride ([Tba]Cl) was investigated in US-ZVI/AC micro-electrolysis system. The degradation degree and intermediates were analyzed and degradation mechanisms were presumed. It is shown that the three functionalized ILs could also be effectively degraded and the degradation pathway of [Amim]Cl was similar to that of the imidazolium ILs discussed above: the imidazolium ring of [Amim]C1was first oxidized and then the ring was opened to form urea or formamide. The degradation of [Bmbim]Br was started by the oxidization of2-positioned C atom of the imidazolium ring, and then the alkyl side chain was broken or the imidazolium ring was opened. The difference in degradation pathway is probably caused by the presence of benzene ring. The degradation of [Tba]Cl was carried out through the gradual elimination of butyl groups. The TOC removal of the three ILs was greater than82%, which indicated the further mineralization of the degradation products identified and significant degradation effect of the ILs in the system.
The high degradation efficiency and TOC removal suggested that the ZVI/AC micro-electrolysis assisted by ultrasonic irradiation could serve as an efficient technology for the removal of ILs from aqueous solutions, and the degradation products are environmental friendly to a great extent. The results presented here may be useful for the assessment of the factors related to the environmental fate and environmental behavior of these commonly used ILs.
引文
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