氢键作用对5-羟基糠醛与咪唑类离子液体分离的影响
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- 英文论文题名：The Effect of Hydrogen Bonding on the Separation of 5-Hydroxymethylfural from Imidazolium Based Ionic Liquids
- 论文作者：王慧勇 ; 刘书燕 ; 李虹培 ; 王键吉
- 英文论文作者：Huiyong Wang ; Shuyan Liu ; Hongpei Li ; Jianji Wang ; School of Chemistry and Chemical Engineering ; Key Laboratory of Green Chemical Media and Reactions ; Ministry of Education Henan Normal University
- 年：2016
- 作者机构：河南师范大学化学化工学院绿色化学介质与反应教育部重点实验室;
- 论文关键词：离子液体 ; 5-羟基糠醛 ; 氢键相互作用
- 会议召开时间：2016-07-01
- 会议录名称：中国化学会第30届学术年会摘要集-第三十三分会：绿色化学
- 语种：中文
- 分类号：O641.3
- 学会代码：ZGHY
- 会议名称：中国化学会第30届学术年会-第三十三分会 ; 绿色化学
- 会议地点：中国辽宁大连
- 主办单位：中国化学会
- 学会名称：中国化学会
- 页数：1
- 文件大小：143k
- 原文格式：D
- 会议级别：全国
摘要
5-羟基糠醛(5-HMF)是一类非常重要的平台化合物[1]。离子液体在5-HMF的制备过程中表现出了优越的性能[2]。然而5-HMF与离子液体很难分离,成为该化学过程实际应用的主要瓶颈之一。从原理上讲,要实现5-HMF从离子液体体系中的有效分离,研究离子液体与5-HMF的相互作用是十分必要的。鉴于此,本文利用傅里叶变换红外(FT-IR)和~1H NMR光谱研究了离子液体[C_4mim]X(X=[CH_3COO]~-、[C_2H_5COO]~-、[CF_3COO]~-、[CH_3OSO_3]~-、[HSO_4]~-、[NO_3]~-、[N(CN)_2]~-、[BF_4]~-)与5-HMF的相互作用,分析了阴离子的性质对离子液体与5-HMF相互作用的影响,得到如下主要结论:1.5-HMF中的C=O与咪唑环上的氢质子形成的氢键很弱,与阳离子上的烷烃链没用相互作用;5-HMF与离子液体的相互作用主要归因于5-HMF中O-H的质子与离子液体阴离子形成的氢键相互作用。2.离子液体阴离子与5-HMF形成氢键能力的大小顺序为:[CH_3COO]~-,[C_2H_5COO]~->[HSO_4]~->[CF_3COO]~->[N(CN)_2]~->[NO_3]~->[CH_3OSO_3]~->[BF_4]~-,这说明具有较强氢键接受能力的阴离子容易与5-HMF形成氢键。
5-Hydroxymethylfurfural(5-HMF) derived from biomass has been considered as a green platform chemical.Ionic liquids(ILs) have shown superior performance in the conversation of biomass to 5-HMF.Nevertheless,the separation of 5-HMF from ILs becomes a technical bottleneck for ILs application in the preparation of 5-HMF.To resolve this problem,understanding the interactions between ILs and 5-HMF is essential.In this work,FT-IR and~1H NMR spectroscopy were combined to investigate the interactions between 5-HMF and ILs composed of1-butyl-3-methylimidazolium cation[C_4mim]~+ and eight different anions.It was found that interactions between ILs and 5-HMF were mainly ascribed to the strong hydrogen bond of anions with O-H group of 5-HMF.The formation ability of hydrogen bonds decreases in the order:[CH_3COO]~-,[C_2H_5COO]~->[HSO_4]~->[CF_3COO]~->[N(CN)_2]~->[NO_3]~->[CH_3OSO_3]~->[BF_4]~-,which suggests that the anions with stronger hydrogen bond acceptor ability have stronger interaction with 5-HMF.
5-Hydroxymethylfurfural(5-HMF) derived from biomass has been considered as a green platform chemical.Ionic liquids(ILs) have shown superior performance in the conversation of biomass to 5-HMF.Nevertheless,the separation of 5-HMF from ILs becomes a technical bottleneck for ILs application in the preparation of 5-HMF.To resolve this problem,understanding the interactions between ILs and 5-HMF is essential.In this work,FT-IR and~1H NMR spectroscopy were combined to investigate the interactions between 5-HMF and ILs composed of1-butyl-3-methylimidazolium cation[C_4mim]~+ and eight different anions.It was found that interactions between ILs and 5-HMF were mainly ascribed to the strong hydrogen bond of anions with O-H group of 5-HMF.The formation ability of hydrogen bonds decreases in the order:[CH_3COO]~-,[C_2H_5COO]~->[HSO_4]~->[CF_3COO]~->[N(CN)_2]~->[NO_3]~->[CH_3OSO_3]~->[BF_4]~-,which suggests that the anions with stronger hydrogen bond acceptor ability have stronger interaction with 5-HMF.
引文
[1]Roman-Leshkov,Y.;Barrett,C.J.;Liu,Z.Y.;Dumesic,J.A.Nature,2007,447:982.
[2]Zhao,H.B.;Holladay,J.E.;Brown,H.;Zhang,Z.C.Science,2007,316:1597.
[2]Zhao,H.B.;Holladay,J.E.;Brown,H.;Zhang,Z.C.Science,2007,316:1597.