糠醛及其衍生物选择性加氢制备戊二醇的研究进展

谭静静; 苏以豪; 高宽; 崔静磊; 王永钊; 赵永祥

doi:10.1016/S1872-5813(21)60036-1

糠醛及其衍生物选择性加氢制备戊二醇的研究进展

doi: 10.1016/S1872-5813(21)60036-1

1.
山西大学化学化工学院精细化学品教育部工程研究中心，山西太原 030006
2.
山西大学资源与环境工程研究所，山西太原 030006

基金项目: 国家自然科学基金（22005182，21703275, U1710221），山西省高等学校科技创新项目（2020L0012）和山西省面上青年基金（201701D221030）资助

详细信息

通讯作者:
E-mail: tanjingjing@sxu.edu.cn

yxzhao@sxu.edu.cn

中图分类号: O643.3
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- 被引次数: 0
出版历程
- 收稿日期: 2020-12-18
- 修回日期: 2021-01-25
- 网络出版日期: 2021-03-30
- 刊出日期: 2021-06-30

Recent advances in the selective hydrogenation of furfural and its derivatives to pentanediol

1.
Engineering Research Center of Ministry of Education for Fine Chemicals, School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China
2.
Institute of Resources and Environmental Engineering, Shanxi University, Taiyuan 030006, China

Funds: The project was supported by the National Natural Science Foundation of China (22005182, 21703275, U1710221), the Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi (2020L0012), Shanxi Provincial Natural Science Foundation of China (201701D221030)

摘要

摘要: 1,2-戊二醇（1,2-PeD）和1,5-戊二醇（1,5-PeD）是高附加值精细化学品，用途广泛。以糠醛及其衍生物为原料经催化加氢制备1,2-PeD和1,5-PeD是绿色的生产工艺，具有良好的应用前景和研究价值。本文系统综述了国内外以糠醛及其衍生物糠醇、四氢糠醇为原料制备1,2-PeD和1,5-PeD的研究现状，重点总结了应用于糠醛、糠醇和四氢糠醇催化加氢制备1,2-PeD和1,5-PeD的催化剂，从催化剂类型、不同催化体系辅助酸/碱催化反应机理、活性金属与掺杂过渡金属氧化物间的协同催化、掺杂过渡金属氧化物的酸性以及不同催化体系中催化剂的构效关系等方面进行了详细阐述，并在此基础上对该研究方向的发展趋势进行了展望。为开发新型、高效、稳定催化糠醛及其衍生物加氢催化剂体系提供了理论指导和有益的借鉴。
- 糠醛 /
- 糠醇 /
- 四氢糠醇 /
- 催化加氢 /
- 1,2-戊二醇 /
- 1,5-戊二醇
Abstract: 1,2-pentanediol (1,2-PeD) and 1,5-pentanediol (1,5-PeD) are high-value fine chemicals with a wide range of uses. It is a green process with well application prospects and research value for the preparation of 1,2-PeD and 1,5-PeD from furfural and its derivatives. Here, the recent advances of furfural and its derivatives furfuryl alcohol and tetrahydrofurfuryl alcohol in the synthesis of 1,2-PeD and 1,5-PeD were reviewed systematically. We focused on the summary of the catalysts used in the catalytic hydrogenation of furfural, furfuryl alcohol and tetrahydrofurfuryl alcohol to prepare 1,2-PeD and 1,5-PeD. The design and application of the catalysts were elaborated from many aspects, including the catalyst type, the reaction mechanism with assist acid/base in different catalytic systems, the synergistic catalysis between active metals and doped transition metal oxides, the influence of acidity of doped transition metal oxides in the catalyst, the structure-activity relationships and so on. On this basis, the development trend of this research direction is prospected. It provides the theoretical guidance and useful reference for developing a new, efficient and stable catalyst system for the hydrogenation of furfural and its derivatives.
- furfural /
- furfuryl alcohol /
- tetrahydrofurfuryl alcohol /
- catalytic hydrogenation /
- 1,2-pentanediol /
- 1,5-pentanediol

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FIG. 721. FIG. 721.

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图 1 糠醛加氢制备1,2-戊二醇和1,5-戊二醇

Figure 1 Route of furfural hydrogenation to prepare 1,2-pentanediol and 1,5-pentanediol

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图 2 糠醛在Pt/水滑石催化剂上加氢为1,2-戊二醇的反应路径^[1]

Figure 2 Reaction pathway of furfural hydrogenation to 1,2-pentanediol on Pt/HT catalyst^[1]

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图 3 糠醛在Rh/OMS-2催化剂上加氢制备1,2-戊二醇的反应机理^[21]

Figure 3 Reaction mechanism of furfural hydrogenation to 1,2-pentanediol over Rh/OMS-2 catalyst^[21]

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图 4 Pd/MMT-K-10催化糠醛加氢制备1,2-戊二醇^[23]

Figure 4 Hydrogenation of furfural to 1,2-pentanediol over Pd/MMT-K-10 catalyst^[23]

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图 5 Cu-Mg₃AlO_4.5催化剂上进行糠醇氢解反应制备戊二醇的反应路径^[22]

Figure 5 Hydrogenolysis pathway for furfuryl alcohol to pentanediol over Cu-Mg₃AlO_4.5 catalyst^[22]

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图 6 Cop-Pt/Co₂AlO₄催化剂催化糠醛转化为1,5-戊二醇的机理图^[27]

Figure 6 Hydrogenation mechanism of furfural to 1,5-pentanediol over Cop-Pt/Co₂AlO₄ catalyst^[27]

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图 7 Co-TiO_y催化剂的形成机制^[30]

Figure 7 Formation mechanism of Co-TiO _y catalyst^[30]

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图 8 Rh-ReO_x/SiO₂催化四氢糠醇氢解为1,5-戊二醇的机理^[37]

Figure 8 Hydrogenolysis mechanism of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Rh-ReO _x /SiO₂^[37]

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图 9 Rh-ReO_x/C催化剂上四氢糠醇氢解为1,5-戊二醇的机理^[39]

Figure 9 Hydrogenolysis mechanism of tetrahydrofurfuryl alcohol to 1,5-pentanediol on Rh-ReO_x /C catalyst^[39]

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图 10 Pt/WO₃/ZrO₂催化四氢糠醇氢解制1,5-戊二醇反应机理模型^[42]

Figure 10 Hydrogenolysis mechanism model of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Pt/WO₃/ZrO₂catalyst^[42]

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图 11 四氢糠醇在Ni-WO_x/SiO₂催化剂上氢解制备1,5-戊二醇反应机理^[44]

Figure 11 Hydrogenolysis mechanism of tetrahydrofurfuryl alcohol to 1,5-pentanediol on Ni-WO _x /SiO₂ catalyst^[44]

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表 1 代表性催化剂催化糠醛（FA)/糠醇（FFA)加氢制备1,2-戊二醇的比较

Table 1 Performance comparison between some representative catalysts of hydrogenolysis FA/FFA to 1,2-PeD

Entry	Substrate	Catalyst	Reaction conditions/ batch reactor	Conversion x/ %	Selectivity of 1,2-PeD s/%	Yield of 1,2-PeD w/%	Ref.
1	FA	Pt/Al₂O₃	240 ℃, 2 MPa, 2 h	43.5	33.3	14.5	[17]
2	FA	Pt/CeO₂	165 ℃, 3 MPa,4 h	100	59.9	59.9	[18]
3	FA	Pt/ HT	150 ℃, 3 MPa, 6 h	100	73.0	73.0	[1]
4	FA	Rh/OMS-2	160 ℃, 3 MPa,8 h	100	87.0	87.0	[21]
5	FA	Pd/MMT-K10	220 ℃, 3.5 MPa,5 h	100	66.0	66.0	[23]
6	FA	Ru/Al₂O₃	200 ℃, 10 MPa, 1 h	100	32	32.0	[24]
7	FFA	Ru/MnO_x	150 ℃, 1.5 MPa, 4 h	89.2	42.1	37.5	[6]
8	FFA	Pt/CeO₂	165 ℃, 2 MPa, 24 h	100	77.0	77.0	[25]
9	FFA	10%Cu/Al₂O₃	140 ℃, 8 MPa, 8 h	85.8	48.1	41.3	[2]
10	FFA	10%Cu-Mg₃AlO_4.5	140 ℃, 6 MPa, 24 h	100	45.2	45.2	[22]
11	FFA	Cu_0.8Mg_5.2Al₂O₃	140 ℃, 4 MPa, 8 h	74.1	51	37.8	[26]

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表 2 代表性催化剂催化糠醛（FA）/糠醇（FFA）/四氢糠醇（THFA）加氢制备1,5-戊二醇的比较

Table 2 Performance comparison between some representative catalysts of hydrogenolysis FA/FFA/THFA to 1,5-PeD

Entry	Substrate	Catalyst	Reaction conditions	Conversion x/ %	Selectivity of 1,5-PeD s/%	Yield of 1,5-PeD w/%	Ref.
1	FA	Pt/Co₂AlO₄	140 ℃, 1.5 MPa, 24 h	100	27.2	27.2	[27]
2	FA	Pd-Ir-ReO_x_/SiO₂	40 ℃(8 h),100 ℃(72 h), 8 MPa	100	71.4	71.4	[14]
3	FA	Rh-Ir-ReO_x_/SiO₂	40 ℃(8 h),100 ℃ (72 h), 8 MPa	100	78.2	78.2	[13]
4	FFA	Co/TiO₂	140 ℃, 2.34 MPa,WHSV=5.8 h^-1	100	30.3	30.3	[30]
5	FFA	Cu-LaCoO₃	140 ℃, 6 MPa, 2 h	100	40.3	40.3	[31]
6	FFA	0.1Cu2.9CoAl	160 ℃, 4 MPa, 2 h	98	44.7	43.8	[32]
7	FFA	Ni-Y₂O₃	150 ℃, 2 MPa, 24 h	100	41.9	41.9	[33]
8	FFA	Ni-La(OH)₃	150 ℃, 2 MPa, 72 h	100	55.8	55.8	[35]
7	THFA	Rh-ReO_x/SiO₂	120 ℃, 8 MPa, 24 h	96	80	76.8	[36]
9	THFA	Rh-MoO_x/SiO₂	100 ℃, 8 MPa, 24 h	94.2	90.3	85.1	[12]
10	THFA	Ir-ReO_x/SiO₂	100 ℃, 8 MPa, 2 h	60.3	94.2	56.8	[38]
11	THFA	Rh-ReO_x/C	120 ℃, 3.4 MPa, 4 h	47.2	97.2	45.9	[10]
12	THFA	Rh-MoO_x/C	120 ℃, 3.4 MPa, 4 h	51.6	91.3	47.1	[10]
13	THFA	Rh/SiO₂ + MoO₃	120 ℃, 6 MPa, 20 h	27.9	80.6	22.5	[11]
14	THFA	Pt /WO₃ @ SiO₂	220 ℃, 6 MPa, 24 h	82.9	72.9	60.4	[40]
15	THFA	Pt/WO₃/ZrO₂	150 ℃, 5 MPa, 5 h	56	65	36.4	[42]
16	THFA	Pt/Y₂O₃-WO₃-ZrO₂	150 ℃, 4 MPa, WHSV=0.2 h^-1	88	68	59.8	[43]
17	THFA	Ni-WO_x/SiO₂	250 ℃, 3.4 MPa, 4 h	28.7	47.3	13.6	[44]
reaction conditions: entry 1−3, 5−15 and 17 were carried out in batch reactor, entry 4 and entry 16 were carried out in fix-bed reactor

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