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化学进展 2022, Vol. 34 Issue (1): 131-141 DOI: 10.7536/PC201242 前一篇   后一篇

• 综述 •

催化转化呋喃类生物质制备芳香烃化合物的研究

曾滴1,2, 刘雪晨1, 周沅逸1,2, 王海鹏1,2, 张玲1,2,*(), 王文中1,2,3,*()   

  1. 1 中国科学院上海硅酸盐研究所高性能陶瓷与超微结构国家重点实验室 上海 200050
    2 中国科学院大学材料科学与光电工程中心 北京 100049
    3 中国科学院大学杭州高等研究院 化学与材料科学学院 杭州 310024
  • 收稿日期:2020-12-25 修回日期:2021-02-03 出版日期:2022-01-20 发布日期:2021-03-04
  • 通讯作者: 张玲, 王文中
  • 基金资助:
    国家自然科学基金项目(51972327); 国家自然科学基金项目(51772312); 国家自然科学基金项目(51961165107)
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Renewable Aromatic Production from Biomass-Derived Furans

Di Zeng1,2, Xuechen Liu1, Yuanyi Zhou1,2, Haipeng Wang1,2, Ling Zhang1,2(), Wenzhong Wang1,2,3()   

  1. 1 State Key Laboratory of High Performance Ceramics and Superfine Microstructure, Shanghai Institute of Ceramics, Chinese Academy of Sciences,Shanghai 200050, China
    2 Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences,Beijing 100049, China
    3 School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences,Hangzhou 310024, China
  • Received:2020-12-25 Revised:2021-02-03 Online:2022-01-20 Published:2021-03-04
  • Contact: Ling Zhang, Wenzhong Wang
  • Supported by:
    National Natural Science Foundation of China(51972327); National Natural Science Foundation of China(51772312); National Natural Science Foundation of China(51961165107)

芳香烃化合物是一类与人类生产生活密切相关的重要有机化工原料。基于石油资源的日益枯竭及其生产过程中带来的环境污染问题,寻找新的合成芳香烃化合物的绿色化学路线成为有机合成领域中的研究热点。呋喃类生物质主要来源于植物系生物质,廉价和分子多样性使其成为合成芳香烃化合物的重要候选原料。通过热催化或低温催化反应,呋喃类生物质与乙烯、丙烯等亲二烯体可进行Diels-Alder环加成和脱水等反应芳构化为芳香烃化合物。以呋喃类生物质为基础的催化反应可高效利用可再生能源,工业应用前景广阔。目前呋喃类生物质催化转化制备芳香烃化合物的研究大部分依赖高温高压的高能耗反应条件,且面临“一锅法”副反应繁杂的问题,例如水解、烷基化、异构化和低聚等。本文综述了基于不同呋喃生物质分子所取得的研究成果和面临的问题,简要介绍 Diels-Alder环加成的反应机理,详细讨论催化剂组分、溶剂效应和亲二烯体对反应效率的影响,并对未来基于生物质的芳香烃化合物合成路径进行展望。

关键词： 呋喃类生物质, 芳香烃化合物, 催化反应, Diels-Alder环加成

As one of the most important renewable chemicals, aromatic compounds are closely related to human production and life. Increasing concerns about diminishing oil resources and the relevant environmental pollution have gradually motivated interests in exploring new green chemistry routes towards aromatic hydrocarbons synthesis. Prized for the low cost and molecular diversity, biomass-derived furans arise as vital candidate raw materials for the production of aromatic compounds in the new century. Through Diels-Alder cycloaddition and the subsequent dehydration, furans could react with enophiles (such as ethylene and propylene) to obtain value-added aromatics including para-xylene. To our knowledge there exist broad industrial application prospects and economic benefits, and the catalytic reation of biomass-derived furans can effectively utilize renewable, abundant, sustainable energy. However, most of the reported catalytic conversion requires elevated temperature and high pressure, and the one-pot method usually results in multifarious and unrestricted side effects, such as hydrolysis, alkylation, isomerization and oligomerization. In this review, we summarize recent developments in the research achievements and issues of aromatic synthesis based on different biomass-derived furan molecules. The mechanism of Diels-Alder cycloaddition reaction is briefly introduced, followed by its influencing factors: catalyst composition, solvent effect and enophile. Then, perspectives and challenges for biomass-based aromatic synthesis are discussed.

Contents

1 Introduction

2 The mechanism of catalytic conversion

2.1 The mechanism of reaction

2.2 Possible side reactions

3 Influence factors

3.1 Solid acid catalyst composition

3.2 Solvents effect

3.3 Dienophile

4 From biomass-derived furans to aromatic hydrocarbons

4.1 By 2,5-dimethylfuran

4.2 By 2-methylfuran

4.3 By 5-hydroxymethylfurfural

4.4 By furfural

4.5 By other biomass-derived furans

5 Conclusion and outlook

Key words: biomass-derived furans, aromatic hydrocarbons, catalytic reaction, Diels-Alder cycloaddition
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表1 呋喃生物质的基本物理性质
Table 1 Basic physical properties of biomass-derived furans
Items DMF MF FU FA FUR HMF
Molecular formula C6H8O C5H6O C4H4O C5H6O2 C5H4O2 C6H6O3
Molecular weight 96.13 82.1 68.07 98.1 96.08 126.11
Boiling point/ ℃ 92~94 63~66 67 170 161.7 115
Flash point/°F 29 -8 160 149 137 175
Density (d/25 ℃) 0.905 0.91 0.936 1.135 1.16 1.243
图1 呋喃类生物质催化转化为芳香烃化合物可能经历的反应机理图
Fig. 1 Schematic representations of the reaction network of the production of aromatic from furan compounds
图2 DMF和乙烯转化过程中可能发生的副反应类型
Fig. 2 Possible side reactions of the reaction of DMF and ethylene
图3 各种催化剂对DMF与乙烯反应合成对二甲苯的催化性能[27]
Fig. 3 Catalytic performance of various catalysts for the p-xylene production from the reaction of DMF with ethylene[27]
图4 呋喃与丙烷共加料的级联反应方案[46]
Fig. 4 Furan with the co-feeding of propane proposed to follow a cascade reaction scheme[46]
表2 呋喃生物质在多种催化剂上发生的Diels-Alder环加成反应
Table 2 Catalytic performances of various catalysts for the cycloaddition of biomass-derived furans
Catalyst Substrates Temperature (K)
/Pressure (bar)/Time (h)		 Conversion (%) and
Selectivity (%)		 ref
WO3/SBA-15 DMF, ethylene 523 K/54 bar/24 h 64.4% and 88% 56
SiO2-SO3H DMF, ethylene 523 K/45 bar/6 h 95% and 89% 57
Sc(OTf)3 and [Emim]NTf2 DMF, acrylic 288 K/Normal pressure/6 h 87% and 68% 33
H-BEA Zeolite MF, ethylene 623 K/20 bar/12 h 99% and 46% 58
Sn-Bate HMF, ethylene 463 K/70 bar/6 h 61% and 31% 59
CH3ONa FUR, acetylene 303~333 K/Normal pressure/49 h
51% and 72%
60
HZSM-5 FU, methanol 723 K/30 bar/0.25 h 100% and 29.4% 61
NaHCO3 FA, activated acrylates 353 K/Normal pressure/22 h 77% and 88% 62
图5 MF和甲醇偶联转化的反应模型[70]
Fig. 5 Proposed reaction chemistry for the coupling conversion of MF and methanol[70]
图6 糠醛和丙烯腈合成间二甲苯二胺的反应路线[60]
Fig. 6 Pathway to meta-xylylenediamine from furfural and acrylonitrile[60]
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