水介质下金属基催化剂催化糠醛加氢的研究进展

doi:10.3969/j.issn.1673-5854.2022.04.006

生物质化学工程 ›› 2022, Vol. 56 ›› Issue (4): 39-48.doi: 10.3969/j.issn.1673-5854.2022.04.006

水介质下金属基催化剂催化糠醛加氢的研究进展

夏海虹¹^,², 周铭昊¹^,²^,³, 陈昌洲¹^,², 刘朋¹^,², 李静¹^,², 蒋剑春¹^,²^,*()

1. 中国林业科学研究院林产化学工业研究所; 江苏省生物质能源与材料重点实验室; 国家林业和草原局林产化学工程重点实验室; 林木生物质低碳高效利用国家工程研究中心, 江苏南京 210042
2. 南京林业大学江苏省林业资源高效加工利用协同创新中心, 江苏南京 210037
3. 扬州大学化学化工学院, 江苏扬州 225002

收稿日期:2021-03-30 出版日期:2022-07-30 发布日期:2022-07-23
通讯作者: 蒋剑春 E-mail:jiangjc@icifp.cn
作者简介:蒋剑春, 院士, 博士生导师, 研究领域: 生物质能源与材料; E-mail: jiangjc@icifp.cn
夏海虹(1987-), 女, 湖北随州人, 助理研究员, 硕士, 主要从事生物质能源与材料研究
基金资助:
国家自然科学基金资助项目(31971609)

Research Progress on Furfural Hydrogenation Using Metal Catalysis in Aqueous Medium

Haihong XIA¹^,², Minghao ZHOU¹^,²^,³, Changzhou CHEN¹^,², Peng LIU¹^,², Jing LI¹^,², Jianchun JIANG¹^,²^,*()

1. Institute of Chemical Industry of Forest Products, CAF; Key Lab. of Biomass Energy and Material, Jiangsu Province; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Bionass, Nanjing 210042, China
2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China
3. School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China

Received:2021-03-30 Online:2022-07-30 Published:2022-07-23
Contact: Jianchun JIANG E-mail:jiangjc@icifp.cn

摘要/Abstract

摘要：

糠醛是连接生物原料和生物炼制工业的桥梁。糠醛在水介质中的还原性转化是制备各种精细化学品的重要途径, 经多相催化剂催化可以得到大量的下游产品, 如(四氢)糠醇、2-甲基(四氢)呋喃、内酯、乙酰丙酸盐、环戊酮、环戊醇等。催化剂的活性主要取决于金属及载体的性质, 以及温度、时间、溶剂和压力等反应条件。本文针对不同的非贵金属(Cu、Ni和Co)和贵金属(Pd、Ru、Pt和Au)基催化剂对糠醛加氢制备环戊酮和环戊醇的研究进展进行了综述, Ru、Pd、Au和Cu基催化剂较其他催化剂有更高的选择性, Cu-Ni双金属催化剂具有优异的催化活性和选择性, 但稳定性有待提高。对金属表面发生氢化反应的机理进行了探讨, 结果表明: 水介质和较弱的路易斯酸性位点在环重排的反应中起关键作用, 同时提出了糠醛在水介质中的加氢反应的未来研究方向。

关键词: 水相, 环戊酮, 环戊醇, 非均相催化, 糠醛, 高附加值化学品

Abstract:

Furfural is the bridge connecting raw biomass to the biorefinery industry. The reductive transformations of furfural in aqueous medium is an important way to prepare a wide variety of fine chemicals. Plenty of downstream products can be obtained by heterogeneous catalyst, such as(tetrahydro) furfuryl alcohol, 2-methyl(tetrahydro) furan, lactone, levulinate, cyclopentanone, cyclopentanol, and so on. The activity of catalyst mainly depends on the properties of metal and support, as well as reaction conditions, such as temperature, time, solvent, and pressure and so on. The research progress of furfural hydrogenation for preparing cyclopentanone and cyclopentanol using different non-noble metal(Cu, Ni, and Co) and precious metals(Pd, Ru, Pt, and Au) based catalyst were summarized. It was found that Ru, Pd, Au, and Cu-based catalysts have higher selectivity than other catalysts, and Cu-Ni bimetallic catalysts have excellent catalytic activity and selectivity, while their stability needs to be improved. The mechanism of the hydrogenation reaction on the metal surface was discussed, and the results showed that the aqueous medium and weaker Lewis acid sites play an important role in the reaction of ring rearrangement. Meanwhile, the future research direction of the hydrogenation reaction of furfural in aqueous medium is proposed.

Key words: water phase, cyclopentanone, cyclopentanol, heterogeneous catalyst, furfural, value-added chemicals

中图分类号:

TQ35

夏海虹, 周铭昊, 陈昌洲, 刘朋, 李静, 蒋剑春. 水介质下金属基催化剂催化糠醛加氢的研究进展[J]. 生物质化学工程, 2022, 56(4): 39-48.

Haihong XIA, Minghao ZHOU, Changzhou CHEN, Peng LIU, Jing LI, Jianchun JIANG. Research Progress on Furfural Hydrogenation Using Metal Catalysis in Aqueous Medium[J]. Biomass Chemical Engineering, 2022, 56(4): 39-48.

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催化剂 catalyst	溶剂 solvent	压力/MPa pressure	温度/℃ temperature	时间/h time	转化率/% conversion	产物 product	产率/% yield	参考文献 reference
Cu-Ni/SBA-15	H₂O	4	160	4	>99	CPO	61	[42]
CuNiAl氧化物oxidate	H₂O	4	130	8	100	CPO	95.8	[43]
CuZnAl氧化物oxidate	H₂O	4	150	6	97.9	CPO	60.3	[44]
Cu/Co₃O₄	H₂O	2	170	1	100	CPO	67	[45]
Cu/Ni@C	H₂O	5	130	5	99.3	CPO	96.9	[46]
Cu-Zn/CNT	H₂O	4	140	10	95.1	CPO	85.3	[47]
Cu/ZnO	H₂O	4	140	6	100	CPO	82	[48]
CuMgAl氧化物oxidate	H₂O	4	140	10	98.5	CPL	93.4	[49]
CuZnAl氧化物oxidate	H₂O	4	150	10	100	CPL	84	[50]

催化剂 catalyst	溶剂 solvent	压力/MPa pressure	温度/℃ temperature	时间/h time	转化率/% conversion	产物 product	产率/% yield	参考文献 references
Ni/HY	H₂O	4	150	9	96.4	CPO	83.4	[51]
NiSAT 320 RS	H₂O	8	175	0.5	98.3	CPO	61	[52]
Ni/SiO₂-Al₂O₃	H₂O	8	175	0.5	100	CPO	57.3	[52]
NiCu/SBA-15	H₂O	4	160	4	99	CPO	62	[42]
雷尼镍Raney Ni	H₂O(MeOH)	1	180	4	97.8	CPO	38.1	[53]
Ni/CNT	H₂O	5	140	10	96.5	CPL	83.6	[54]
NiMo/CNT	H₂O	5	150	6	100	CPL	88.6	[55]

催化剂 catalyst	溶剂 solvent	压力/MPa pressure	温度/℃ temperature	时间/h time	转化率/% conversion	产率/% yield	参考文献 references
Co/ZrO₂	H₂O	2	160	4	100	68(CPL)	[56]
Co/ZrO₂-La₂O₃	H₂O	2	160	4	100	82(CPL)	[56]
Ni-Co/TiO₂	H₂O		150	4	100	75.5(CPL)	[57]
CuCo@C	H₂O	0.5	150	9	100	90.2(CPO)	[58]

催化剂 catalyst	溶剂 solvent	压力/MPa pressure	温度/℃ temperature	时间/h time	转化率/% conversion	产率/% yield	参考文献 reference
Pd/C	H₂O	3	160	1	97.8	67.1	[59]
Pd-Cu/C	H₂O	3	160	1	98	92.1	[60]

催化剂 catalyst	溶剂 solvent	压力/MPa pressure	温度/℃ temperature	时间/h time	转化率/% conversion	产率/% yield	参考文献 reference
5% Ru/C	H₂O	3	175	1	100	57.3	[59]
Ru/MIL-101	H₂O	4	160	2.5	99	95	[61]
3% Ru/C	H₂O	4	160	2.5	72	28.8	[61]
6% Ru/CNT	H₂O	1	160	5	99	90.1	[62]

水介质下金属基催化剂催化糠醛加氢的研究进展

Research Progress on Furfural Hydrogenation Using Metal Catalysis in Aqueous Medium

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