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基于氢键作用的含酚油混合物中酚的高效分离

纪柚安 赵晓胜 刘青 杨玉凤 韩江则

纪柚安, 赵晓胜, 刘青, 杨玉凤, 韩江则. 基于氢键作用的含酚油混合物中酚的高效分离[J]. 燃料化学学报. doi: 10.1016/S1872-5813(21)60137-8
引用本文: 纪柚安, 赵晓胜, 刘青, 杨玉凤, 韩江则. 基于氢键作用的含酚油混合物中酚的高效分离[J]. 燃料化学学报. doi: 10.1016/S1872-5813(21)60137-8
JI You-an, ZHAO Xiao-sheng, LIU Qing, YANG Yu-feng, HAN Jiang-ze. Efficient separation of phenols from phenols-containing oil mixtures via forming hydrogen bonds[J]. Journal of Fuel Chemistry and Technology. doi: 10.1016/S1872-5813(21)60137-8
Citation: JI You-an, ZHAO Xiao-sheng, LIU Qing, YANG Yu-feng, HAN Jiang-ze. Efficient separation of phenols from phenols-containing oil mixtures via forming hydrogen bonds[J]. Journal of Fuel Chemistry and Technology. doi: 10.1016/S1872-5813(21)60137-8

基于氢键作用的含酚油混合物中酚的高效分离

doi: 10.1016/S1872-5813(21)60137-8
基金项目: 河北科技大学人才引进科研启动基金(81/1181381)和河北省高等学校科学技术研究重点项目(ZD2021320)资助
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    Tel: 0311-88632183, E-mail: jiyouan@126.com

  • 中图分类号: TQ523.59

Efficient separation of phenols from phenols-containing oil mixtures via forming hydrogen bonds

Funds: The project was supported by the Scientific Research Foundation for the Introduction of Talents of Hebei University of Science and Technology (81/1181381) and the Key Projects of Science and Technology Research in Colleges and Universities of Hebei Province (ZD2021320)
  • 摘要: 本文采用米屈肼(THP)、吉拉尔特试剂T、吉拉德试剂P基于氢键作用分离油中的苯酚。结果发现,三种分离剂均可与苯酚形成低共熔溶剂(DES)而分离苯酚,其中米屈肼对苯酚的分离效率最高,可达96.5%;油中残余苯酚浓度低至1.3 g/L;10 min即可完成分离;苯酚的初始浓度不影响分离后油中最低残余苯酚浓度(约8.8 g/L)。采用正己烷洗涤的方法去除DES中夹带的中性油。结果发现,DES中的中性油与苯酚质量比降至0.04,说明酚产品纯度将大幅提高。米屈肼可再生并重复使用五次,性质不变。FT-IR表征发现米屈肼与苯酚间存在氢键作用。
  • 图  1  不同分离剂对甲苯中苯酚的分离效率。

    Figure  1  Separation of phenol separated by different separation agents

    conditions: initial phenol content, 100.0 g/L; temperature, 25 ℃; stirring time, 30 min; mole ratio, 0.8; oil mixture, toluene+phenol

    图  2  搅拌时间对苯酚分离效果的影响

    Figure  2  Effect of stirring time on phenol separation

    conditions: initial phenol content, 100.0 g/L; separation temperature, 25 ℃; THP to phenol content 0.8; mixture, toluene+phenol

    图  3  分离温度对苯酚分离效果的影响

    Figure  3  Effect of separation temperature on phenol separation

    conditions: initial phenol content, 100.0 g/L; separation temperature, 25 ℃; THP to phenol content 0.8; oil mixture, toluene+phenol

    图  4  米屈肼与苯酚物质的量比对苯酚分离效果的影响

    Figure  4  Effect of THP to phenol mole ratio on phenol separation

    conditions: initial phenol content, 100.0 g/L; separation temperature, 25 ℃; stirring time, 30 min; oil mixture, toluene+phenol

    图  5  米屈肼与苯酚物质的量比对苯酚分配系数的影响

    Figure  5  Effect of THP to phenol mole ratio on D of phenol conditions: initial phenol content, 100.0 g/L; separation temperature, 25 ℃; stirring time, 30 min

    图  6  不同米屈肼与苯酚物质的量比下甲苯的夹带

    Figure  6  The entrainment of toluene at different THP to phenol mole ratios

    conditions: initial phenol content, 100.0 g/L; separation temperature, 25 ℃; stirring time, 30 min

    图  7  苯酚初始浓度对苯酚分离效果的影响

    Figure  7  Effect of initial phenol content on phenol separation conditions: separation temperature, 25 ℃; stirring time, 30 min; THP to phenol content, 0.8; oil mixture, toluene+phenol

    图  8  米屈肼与苯酚物质的量比对苯酚分离效果的影响

    Figure  8  Effect of THP to phenol mole ratio on phenol separation

    conditions: mixture, n-hexane+phenol, initial phenol content, 10.0 g/L, separation temperature, 25 ℃; stirring time, 30 min

    图  9  米屈肼的再生与重复使用

    Figure  9  The regeneration and reuse of THP

    conditions: initial phenol content, 100.0 g/L, separation temperature, 25 ℃; stirring time, 30 min; THP to phenol content, 0.8

    图  10  米屈肼样品的1H NMR表征

    Figure  10  1H NMR spectra of THP samples

    图  11  米屈肼的回收率随重复使用次数的变化

    Figure  11  Recovery rate of THP as a function of cycle time

    图  12  米屈肼、苯酚、两者混合物的FT-IR谱图

    Figure  12  FT-IR spectra of THP, phenol, and their mixture

    图  13  米屈肼与苯酚作用示意图

    Figure  13  Diagram of interaction between THP and phenol

    表  1  实验试剂一览表

    Table  1  Chemicals used in this work

    ChemicalCAS numberSpecificationSupplier
    Phenol108-95-298%Aladdin Chemical Co., Ltd., Shanghai, China
    Toluene108-88-399%Beijing Tongguang Fine Chemicals Co., Ltd., Beijing, China
    n-hexane110-54-397%Beijing Tongguang Fine Chemicals Co., Ltd., Beijing, China
    Ether60-29-798%Beijing Tongguang Fine Chemicals Co., Ltd., Beijing, China
    Girard's reagent T123-46-698%Aladdin Chemical Co., Ltd., Shanghai, China
    Girard's reagent P1126-58-598%Aladdin Chemical Co., Ltd., Shanghai, China
    THP76144-81-598%Aladdin Chemical Co., Ltd., Shanghai, China
    D2O7789-20-099.9%Saen Chemical Technology Co., Ltd., Shanghai, China
    下载: 导出CSV
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  • 收稿日期:  2021-05-31
  • 修回日期:  2021-07-06
  • 网络出版日期:  2021-08-10

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