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化学进展 2022, Vol. 34 Issue (8): 1748-1759 DOI: 10.7536/PC211007 前一篇   后一篇

• 综述 •

生物基平台化合物催化转化制备糠醇

杨启悦1, 吴巧妹1, 邱佳容1, 曾宪海2, 唐兴2, 张良清1,*()   

  1. 1 福州大学先进制造学院 晋江 362251
    2 厦门大学能源学院 厦门 361102
  • 收稿日期:2021-10-11 修回日期:2021-12-17 出版日期:2022-08-20 发布日期:2022-04-01
  • 通讯作者: 张良清
  • 作者简介:

    作者简介：张良清 2019年毕业于厦门大学能源化工专业,获工学博士学位,2020年就职于福州大学。长期从事绿色化学和绿色精细化工材料等方面研究。2021年在生物质催化转化领域获批国家自然科学基金青年项目;在化学和催化等领域以第一作者发表中科院JCR 1区论文2篇,JCR 2区论文2篇,并授权4项发明专利。参与并完成多项催化转化和分离纯化等领域相关的国家自然科学基金项目、福建省发改委重大产业化投资项目和企业重大合作项目。

  • 基金资助:
    国家自然科学基金项目(22108038); 天津大学-福州大学自主创新基金合作项目(TF2022-10)
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Catalytic Conversion of Bio-Based Platform Compounds to Fufuryl Alcohol

Qiyue Yang1, Qiaomei Wu1, Jiarong Qiu1, Xianhai Zeng2, Xing Tang2, Liangqing Zhang1()   

  1. 1 School of Advanced Manufacturing, Fuzhou University, Jinjiang 362251, China
    2 College of Energy, Xiamen University, Xiamen 361102, China
  • Received:2021-10-11 Revised:2021-12-17 Online:2022-08-20 Published:2022-04-01
  • Contact: Liangqing Zhang
  • Supported by:
    National Natural Science Foundation of China(22108038); Tianjin University-Fuzhou University Independent Innovation Fund Cooperation Project(TF2022-10)

糠醇(FOL)作为一种重要且多用途的有机化工原料,可以有效地转化为各种高价值的化学品,如糠醛树脂、脲醛树脂、酚醛树脂、果酸、增塑剂和火箭燃料等。以糠醛(FAL)、木糖和果糖为原料经催化加氢制备FOL的绿色生产工艺,具有良好的应用前景和研究价值。本文系统总结了近年来国内外以FAL、木糖、果糖为原料制备FOL的研究现状,从催化剂类型、催化效率和催化机理等方面对制备FOL的催化剂进行了总结,并在此基础上对催化加氢制备FOL的发展趋势进行了展望,为开发更为新型、高效、绿色、稳定的催化剂体系提供理论指导和有益借鉴。

关键词： 糠醇, 催化剂, 糠醛, 木糖, 果糖

Furfuryl alcohol (FOL), as an important and promising organic chemical product, can be effectively converted into various high-value chemicals, such as furfural resin, urea-formaldehyde resin, phenolic resin, fruit acid, plasticizer, rocket fuel, etc. The green FOL production by catalytic hydrogenation using furfural (FAL), xylose, and fructose as raw materials has good application prospects and research values. This article systematically reviews the research status of the FOL production from FAL, xylose, and fructose on the recent advances, and summarizes from the aspects of catalyst types, catalytic efficiency and mechanism for FOL production. On this basis, the development trends of the FOL production by catalytic hydrogenation are prospected, which may provide theoretical guidance and useful reference for developing new efficient green and stable catalytic system.

Contents

1 Introduction

2 Preparation of FOL from different substrates by catalytic conversion

2.1 Preparation of FOL from FAL by catalytic conversion

2.2 Preparation of FOL from xylose by one-pot method

2.3 Preparation of FOL from fructose by one-pot method

3 Conclusion and outlook

Key words: furfuryl alcohol, catalyst, furfural, xylose, fructose
()
图1 FAL可能的反应途径
Fig. 1 Possible reaction pathways of FAL
图2 高附加值FOL衍生物
Fig. 2 High value-added FOL derivatives
表1 贵金属催化剂催化FAL制备FOL
Table 1 Preparation of FOL from FAL by noble metal catalysts
Entry Catalyst Solvent Temperature ( ℃) Time (h) Conversion (%) Selectivity (%) Run
(Stability)		 ref
1 Pt/m-CN-2 Isopropanol 70 2 98.5 99.3 5 (Stable) 37
2 Pt/(Fe, Co)-BTC-2 Isopropanol 70 2 98 99 5 (Stable) 38
3 Pt3Fe/CeO2 Isopropanol 100 4 99.8 100 6 (Stable) 39
4 Pt-0.2Co/TiO2 Methanol 50 2 100 97.5 / 40
5 0.5Pd/TiH2 Isopropanol 60 3 100 73 2 (Unstable) 41
6 Ru/Ph2P(CH2)4PPh2 / 140 1.3 >99.9 100 12 (Stable) 42
7 Ru(CO)/rGO Water 20 10 93.3 98 4 (Stable) 43
8 Au/Al2O3 / 140 / <40 100 / 32
9 Au/CeO2 / 200 / / 100 / 44
10 Ir-CoOx/A12O3 Ethanol 45 2 98 99 5 (Stable) 45
表2 非贵金属催化剂催化FAL制备FOL
Table 2 Preparation of FOL from FAL by non-noble metal catalysts
Entry Catalyst Solvent Temperature ( ℃) Time (h) Conversion (%) Selectivity (%) Run
(Stability)		 ref
1 Cu-N/OAC 2-propanol 150 6 99.5 98.4 5 (Stable) 46
2 Cu2Zn/SiO2-IS Water 120 4 81.9 94.8 4 (Unstable) 47
3 Chi30Cu CPME 190 5 78 / / 48
4 Cu@Mg/γ-Al2O3 / 170 5 >99 94 6 (Stable) 49
5 Ni@OMC 1-propanol 180 12 92.3 98.6 5 (Stable) 50
6 C@Ni3P-1 2-propanol 160 4 97 96.3 4 (Unstable) 51
7 D-WO3 Water/Ethanol 100 2 52 85 / 54
8 CuNi/MgAlO Methanol 100 4 >99 >99 6 (Stable) 55
9 NiCoZn@CN-600 Tetrahydrofuran 160 4 100 >99 5 (Stable) 56
10 Ni-Cu Decyl alcohol 130 2 / 100 / 57
11 7Ni-Cu/ZrO2 Isopropanol 200 4 99.7 / 5 (Unstable) 58
12 2%Ni-5%Cu/SiO2 Methanol 100 2 94 64 / 59
13 CZAl Water 100 4 >99 >99 5 (Stable) 60
表3 以醇作为氢源催化FAL制备FOL
Table 3 Preparation of FOL using alcohols as a hydrogen donor
Entry Catalyst Solvent Temperature ( ℃) Time (h) Conversion (%) Selectivity (%) Run
(Stability)		 ref
1 6% Ru/mZrH Ethanol 150 / 92 99 / 63
2 Co-Ru/C Benzyl alcohol 150 12 98 100 4 (Stable) 67
3 10%Ni-15%W/AC Isopropanol 260 5 83 / / 68
4 Ni-SAs/NC 2-propanol 130 3 95.6 96.8 4 (Stable) 69
5 Fe-L/C-800 2-butanol 160 15 91.6 83 5 (Stable) 64
6 γ-Fe2O3@HAP Isopropanol 180 10 96.2 95.3 6 (Stable) 70
7 Fe3O4/C Isopropanol 200 4 76.4 98.5 4 (Stable) 71
8 Zr@Co-2 2-propanol 160 4 93.9 97.3 7 (Stable) 72
9 Zr5Al5 2-propanol 130 5 95 / 4 (Unstable) 65
10 CoCuAl 2-propanol 200 2 100 63 3 (Unstable) 66
11 Ov-rich meso-LMO Isopropanol 180 3 99 96 5 (Stable) 74
12 TiO2 2-pentanol 25 0.5 >99 99 2 (Stable) 75
图3 木糖一锅法转化为FOL可能的反应路径
Fig. 3 Possible reaction routes of the one-pot transformation of xylose to FOL
表4 木糖制备FOL
Table 4 Preparation of FOL from xylose
Entry Catalyst Solvent Temperature ( ℃) Time (h) Conversion (%) Selectivity (%) Run
(Stability)		 ref
1 Pt/SiO2+ZrO2-SO4 Water/2-propanol 130 6 65 51 2 (Unstable) 78
2 Pt/ZrO2-SO4 Water/Isopropanol 130 1 32 27 1 (Unstable) 79
3 Ru/MWCNT Water/2-propanol 130 6 100 9 / 80
4 Pd/MWCNT Water/2-propanol 130 6 66 12 / 80
5 Zeolite Beta Water/Isopropanol 130 1 / 75 / 81
6 [Al]-SBA-15 Water/2-propanol 130 4 13 11 3 (Unstable) 82
7 Pt/SBA-15-SO3H Water/Isopropanol 130 6 65 / 1 (Unstable) 83
8 Cu/SBA-15-SO3H Water/n-butanol 140 6 94 / / 77
9 Ru-SRGO-2 Water/1.4-dioxane 150 4 100 70.4 5 (Stable) 84
10 Cu/ZnO/Al2O3+Hβ Water/γ-butyrolactone 150 / 100 87.2 / 87
11 Formic acid+Co-N-C Water/1.4-dioxane 160 0.5 100 69.5 5 (Stable) 88
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