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Progress in Chemistry 2022, Vol. 34 Issue (1): 131-141 DOI: 10.7536/PC201242 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
  • 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)
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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
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
Fig. 1 Schematic representations of the reaction network of the production of aromatic from furan compounds
Fig. 2 Possible side reactions of the reaction of DMF and ethylene
Fig. 3 Catalytic performance of various catalysts for the p-xylene production from the reaction of DMF with ethylene[27]
Fig. 4 Furan with the co-feeding of propane proposed to follow a cascade reaction scheme[46]
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
Fig. 5 Proposed reaction chemistry for the coupling conversion of MF and methanol[70]
Fig. 6 Pathway to meta-xylylenediamine from furfural and acrylonitrile[60]
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