交联菲罗啉负载铜催化剂用于合成三甲基苯醌

郭婉婉; 李如月; 黄军

doi:10.11949/j.issn.0438-1157.20181322

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交联菲罗啉负载铜催化剂用于合成三甲基苯醌

催化、动力学与反应器 | 更新时间：2026-07-24

- 交联菲罗啉负载铜催化剂用于合成三甲基苯醌
- Copper catalyst supported on cross-linked phenanthroline for oxidative synthesis of 2,3,5-trimethyl-1,4-benzoquinone
- 化工学报 2019年70卷第3期页码：929-936
- 作者机构：
  
  南京工业大学化工学院，江苏南京 211816
- 作者简介：
  
  郭婉婉（1993—），女，硕士研究生，13770635576@163.com
  黄军（1973—），男，博士，教授，junhuang@njtech.edu.cn
- 基金信息：
  
  国家自然科学基金项目(21676140)
- DOI：10.11949/j.issn.0438-1157.20181322
  中图分类号： TQ 466.5
- 收稿：2018-11-12，
  
  修回：2018-12-05，
  
  网络首发：2026-07-24，
  
  纸质出版：2019-03-05
- 稿件说明：
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郭婉婉, 李如月, 黄军. 交联菲罗啉负载铜催化剂用于合成三甲基苯醌[J]. 化工学报, 2019, 70(3): 929-936

GUO Wanwan, LI Ruyue, HUANG Jun. Copper catalyst supported on cross-linked phenanthroline for oxidative synthesis of 2,3,5-trimethyl-1,4-benzoquinone[J]. CIESC Journal, 2019, 70(3): 929-936
郭婉婉, 李如月, 黄军. 交联菲罗啉负载铜催化剂用于合成三甲基苯醌[J]. 化工学报, 2019, 70(3): 929-936 DOI： 10.11949/j.issn.0438-1157.20181322.

GUO Wanwan, LI Ruyue, HUANG Jun. Copper catalyst supported on cross-linked phenanthroline for oxidative synthesis of 2,3,5-trimethyl-1,4-benzoquinone[J]. CIESC Journal, 2019, 70(3): 929-936 DOI： 10.11949/j.issn.0438-1157.20181322.

摘要

烷基取代的苯醌可用作多种生物活性化合物的功能结构单元。提出了一种在温和条件下，用氧气氧化2

6-三甲基苯酚（TMP）得到2

5-三甲基-1

4-苯醌（TMQ，维生素E前体）的方法。利用Friedel-Crafts烷基化反应，成功制备了一种基于1

10-菲罗啉的交联多孔聚合物负载铜催化剂Cu/PPhen。采用氮气吸附脱附、SEM、FTIR和XPS对催化剂Cu/PPhen-4进行了一系列的表征，获得了催化剂的基本结构特征。并考察了催化剂的加入量、溶剂、氧气压力、反应温度以及反应时间等因素对Cu/PPhen-4催化氧化制备2

5-三甲基-1

4-苯醌的影响，得到最佳的工艺条件。当2

6-三甲基苯酚的加入量为136 mg时，催化剂量为150 mg，乙腈量为2 ml，0.5 MPa的氧气，40℃下反应4 h，2

5-三甲基-1

4-苯醌的收率可以达到99%。催化剂Cu/PPhen-4具有较好的稳定性，可以回收至少五次，活性几乎没有下降。

Abstract

Alkyl-substituted benzoquinones were versatile building blocks for a variety of biologically active compounds. The catalytic oxidation of 2

6-trimethylphenol (TMP) to 2

5-trimethyl-1

4-benzoquinone (TMQ

vitamin E precursor) with oxygen gas was proposed under mild conditions. The cross-linked porous polymer (PPhen) was synthesized by Friedel-Crafts alkylation of 1

10-phenanthroline

and the related Cu catalysts (Cu/PPhen) were prepared. The prepared Cu/PPhen catalysts were characterized by nitrogen adsorption and desorption isotherms

scanning electron microscope (SEM)

Fourier transform infrared spectroscopy (FTIR)

and X-ray photoelectron spectroscopy (XPS) .The basic structure of the Cu/PPhen catalysts were obtained. Reaction conditions

such as catalyst loading

solvent

oxygen pressure

reaction temperature and reaction time were studied

and 2

5-trimethyl-1

4-benzoquinone was obtained in 99% yield with the optimized reaction conditions. The optimized reaction conditions were achieved as 136 mg 2

6-trimethylphenol with 150 mg the Cu/PPhen-4 catalyst in 2 ml acetonitrile

under 0.5 MPa O

at 40℃ for 4 h. The Cu/PPhen-4 catalyst has good stability and can be recovered at least five times with almost no decrease in activity.

关键词

Keywords

references

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