生物质基多元醇的多相催化选择性氢解★

doi:10.6023/A23020042

化学学报 ›› 2023, Vol. 81 ›› Issue (5): 533-547.DOI: 10.6023/A23020042 上一篇下一篇

所属专题：庆祝《化学学报》创刊90周年合辑

综述

生物质基多元醇的多相催化选择性氢解^★

刘露杰^a, 张建^b, 王亮^a, 肖丰收^a^,^b^,^*()

a 浙江大学化学工程与生物工程学院生物质化工教育部重点实验室浙江杭州 310027
b 北京化工大学软物质科学与工程高精尖创新中心北京 100029

投稿日期:2023-02-21 发布日期:2023-03-28

作者简介:

刘露杰, 男, 博士. 2021年毕业于Tohoku University获工学博士学位, 导师为Keiichi Tomishige教授, 主要研究生物质平台化合物多元醇的加氢脱氧研究. 同年, 加入浙江大学肖丰收教授课题组, 开展有关分子筛类加氢催化剂稳定性和构效关系的博士后工作研究.

张建, 男, 北京化工大学副教授. 2017 年毕业于浙江大学,获理学博士学位, 导师为肖丰收教授. 2019 年入职北京化工大学软物质科学与工程高精尖创新中心. 主要从事沸石基催化材料的合成、表征与催化生物质转化性能等方面的研究.

王亮, 男, 分别于2008和2013年从吉林大学获得理学学士和理学博士学位, 导师为肖丰收教授. 随后加入浙江大学从事博士后研究工作. 2018年10月, 在浙江大学化学与生物工程学院任“百人计划”研究员. 主要研究多孔催化材料及其在碳资源转化与精细化学品合成方面的应用.

肖丰收, 男, 浙江大学求是特聘教授. 于1983和1986年在吉林大学化学系分别获得学士和硕士学位. 1986~1990年间, 作为中日联合培养博士生, 分别在吉林大学、大连化学物理研究所、日本北海道大学学习, 1990获吉林大学博士学位, 并于1993~1994年间在美国加州大学戴维斯分校进行博士后研究. 他的研究工作主要从事沸石分子筛和纳米孔材料的合成、表征与催化性能等方面的研究.

^★ 庆祝《化学学报》创刊90周年.

基金资助:
受国家自然科学基金(22202176); 中国博士后科学基金(2021M702802)

Heterogeneous Catalysts for Selective Hydrogenolysis of Biomass-derived Polyols^★

Lujie Liu^a, Jian Zhang^b, Liang Wang^a, Fengshou Xiao^a^,^b()

a Key Lab of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, Zhejiang 310027
b Beijing Advanced Innovation Center for Soft Matter, Science and Engineering, Beijing University of Chemical Technology, Beijing 100029

Received:2023-02-21 Published:2023-03-28
Contact: *E-mail: fsxiao@zju.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
National Natural Science Foundation of China(22202176); China Postdoctoral Science Foundation(2021M702802)

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摘要/Abstract

由生物质资源衍生得到的糖醇是一种可再生碳原料, 并可以通过多相催化技术转化为高附加值的大宗化学品. 因此, 设计与制备具有高活性、高选择性和高稳定性的多相催化材料对于实现糖醇的定向转化具有重要意义. 近年来, 有关糖醇选择性氢解制备高附加值的一元醇、二元醇等已有许多报道, 其中典型的Ir-ReO_x和Pt-WO_x催化剂在性能上有了进一步突破. 此综述详细介绍了糖醇的选择性转化路径, 并从金属-金属氧化物的相互作用、催化剂的构效关系和糖醇C—O键断裂的机理等方面进行归纳, 并对糖醇定向转化的发展进行讨论与展望, 这些对于新型多相催化材料的设计以及糖醇转化潜在的工业应用具有意义.

关键词: 生物质基多元醇, 糖醇, 多相催化剂, 双功能催化剂, 加氢脱氧, 选择性氢解

Catalytic transformation of biomass-derived polyols into valuable chemicals has attracted attention from the viewpoint on using renewable carbon resources. Therefore, it is important for design and preparation of heterogeneous catalysts with high activity, high selectivity, and high stability for the selective conversion of biomass-derived polyols. Recently, it has been reported the selective production of mono-alcohols and/or diols by selective hydrogenolysis of sugar alcohols, where the Ir-ReO_x and Pt-WO_x as typical heterogeneous catalysts are highly efficient. In this review, we briefly summarized the routes for the selective conversion of sugar alcohols into mono-alcohols and/or diols, where the metal-metal oxide interaction for catalyst design, relationship between catalyst structure and performance, and reaction mechanism for the C—O hydrogenolysis are particularly discussed. In addition, the future trend for the selective hydrogenolysis of sugars is also prospected. This review might be helpful for design of novel heterogeneous catalysts in sugar alcohol conversion.

Key words: biomass-derived polyols, sugar alcohols, heterogeneous catalyst, bifunctional catalyst, hydrodeoxygenation, selective hydrogenolysis

引用此文

刘露杰, 张建, 王亮, 肖丰收. 生物质基多元醇的多相催化选择性氢解^★[J]. 化学学报, 2023, 81(5): 533-547.

Lujie Liu, Jian Zhang, Liang Wang, Fengshou Xiao. Heterogeneous Catalysts for Selective Hydrogenolysis of Biomass-derived Polyols^★[J]. Acta Chimica Sinica, 2023, 81(5): 533-547.

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图/表 16

图1. 生物质基多元醇的来源、转化及加氢脱氧中的催化过程示意图

Figure 1. Schematic diagram of the source, transformation, and catalytic process in hydrodeoxygenation of biomass-derived polyols

Catalyst	T/K	p(H₂)/MPa	1,3-PrD yield/%		Ref.
Pt-LiSiW/ZrO₂	453	5.0	23	0.2 (0.012)	[44]
Pt/WO_x/Al₂O₃	493	4.5	28	0.6 (0.68)	[45]
Pt/WO_x/Al₂O₃	493	4.5	39	1 (1.1)	[46]
Pt/WO₃/TiO₂/SiO₂	453	5.5	14	1 (0.51)	[47]
Pt/Ti₈₀W₂₀	453	5.5	15	1 (0.10)	[48]
Pt/WO_x/SiO₂-ZrO₂	453	5.0	28	1 (0.17)	[49]
Pt-WO₃/SBA-15	483	0.1	36	2 (0.51)	[50]
Pt/W-SBA-15	423	4.0	61	2 (13)	[51]
Pt/WO_x/AlOOH	453	5.0	66	2 (0.45)	[32]
Pt/WO₃/ZrO₂	403	4.0	32	2 (0.61)	[52]
Pt/WO_x/Al₂O₃	453	5.0	28	3 (1.4)	[53]
Pt/meso-WO_x	433 413	1.0 1.0	14 22	1 (0.020) 0.7 (0.015)	[54]
Pt-WO_x/SiO₂	453	8.0	—	3.3 (7.0)	[35]
Pt-WO_x/SiO₂	413 413	8.0 8.0	57 —	4.8 (20) 6.2 (26)	[34]
Pt/ZrW₃₈Mn₃	453	8.0	26	4 (0.21)	[55]
Pt-WO_x/t-ZrO₂	413	8.0	49	5.1 (1.3)	[56]
Pt^δ^＋WO_x/T-Ta₂O₅	433	5.0	40	30.8 (42)	[33]

表1. 甘油氢解制1,3-丙二醇反应中的Pt-WOx催化剂性能

Table 1. Catalytic performances of the Pt-WOx based-catalysts for hydrogenolysis of glycerol to 1,3-PrD

Catalyst	T/K	p(H₂)/MPa	1,3-PrD yield/%	P_1,3-PrD/(g•g_Ir^-1•h^-1) or P_1,3-PrD/(g•g_Re^-1•h^-1)	Ref.
Ir-Re/KIT-6 (Ir-Re alloy)	393	8.0	22	7 (7)	[57]
Ir-ReO_x/SiO₂＋H₂SO₄	393	8.0	38	18 (22)	[37]
Ir-ReO_x/SiO₂	393	8.0	32	22 (67)	[40]
Ir-ReO_x/Rutile	393	8.0	36	94 (323)	[39]

表2. 甘油氢解制1,3-丙二醇反应中的Ir-ReOx催化剂性能

Table 2. Catalytic performances of Ir-ReOx based-catalysts for hydrogenolysis of glycerol to 1,3-PrD

图2. 赤藓醇氢解的反应路径示意图[61]

Figure 2. Schematic diagram of erythritol hydrogenolysis[61]

图3. 1,4-脱水赤藓糖醇两步法和一步法制1,3-丁二醇的反应示意图[65]

Figure 3. Schematic diagram of one and two steps for the conversion of 1,4-anhydroerythritol transformation into 1,3-butanediol[65]

图4. 文献中木糖醇和山梨糖醇的转化路径示意图[66,76]

Figure 4. Schematic diagram of xylitol and sorbitol transformation route in literature[66,76]

图5. 木糖醇在Pt-WOx/SiO2催化剂上转化为戊醇的路径示意图[66]

Figure 5. Schematic diagram of xylitol conversion over Pt-WOx/SiO2 catalyst[66]

图6. 反应中Ir/rutile、Ir-FeOx/rutile和Irc-r-FeOx/rutile催化剂的结构模型[68]

Figure 6. Model structures of Ir/rutile, Ir-FeOx/rutile, and Irc-r-FeOx/rutile during the reaction[68]

图7. 4% (w)-Ir Ir-ReOx/SiO2 (Re/Ir=0.83) (a)[94]和20% (w)-Ir Ir-ReOx/SiO2 (Re/Ir=0.34) (b)的电镜图和催化剂模型结构[40]

Figure 7. TEM image and model structure of (a) 4% (w)-Ir Ir-ReOx/SiO2 (Re/Ir=0.83)[94] and (b) 20% (w)-Ir Ir-ReOx/SiO2 (Re/Ir=0.34)[40]

图8. Pt-WOx/SiO2催化剂上Br?nsted酸性位强度和WOx负载量的关系[35]

Figure 8. The relationship between Br?nsted acidity and WOx amount on Pt-WOx/SiO2 catalyst[35]

图9. 不同W负载量的Pt-WOx/SiO2 [4% (w) Pt]催化剂结构(a)和不同预处理的Pt-WOx/SiO2 [4% (w) Pt, W/Pt=0.25]催化剂的结构(b)[34]

Figure 9. Structures of Pt-WOx/SiO2 catalysts [4% (w) Pt] tuned by W amount (a), and Pt-WOx/SiO2 [4% (w) Pt, W/Pt=0.25] catalyst after different pretreatments during the reaction (b)[34]

图10. 2% (w)-Ir Ir-ReOx/rutile (a)和4% (w)-Ir Ir-ReOx/rutile的催化剂结构(b), 4% (w)-Ir Ir-ReOx/rutile的TEM图(c)和高分辨率的透射电镜(HRTEM)图(d), P1,3-PrD和Ir负载量的关系(e), P1,3-PrD和Re/Ir物质的量比的关系(f)[39,61]

Figure 10. Structures of (a) 2% (w)-Ir Ir-ReOx/rutile and (b) 4% (w)-Ir Ir-ReOx/rutile, (c) TEM image of 4% (w)-Ir Ir-ReOx/rutile and (d) high resolution transmission electron microscope (HRTEM) image of 4% (w)-Ir Ir-ReOx/rutile, (e) relationship between P1,3-PrD and Ir amount, and (f) relationship between P1,3-PrD and Re/Ir molar ratio[39,61]

图11. Ir-ReOx催化剂上甘油的直接氢解机理[37]

Figure 11. Direct hydrogenolysis mechanism for glycerol over Ir-ReOx catalyst[37]

图12. 甘油在Re3O6H2团簇的ReOx物种上不同的吸附模式(a)和Ir-ReOx催化剂上的甘油氢解机理(b)[105]

Figure 12. (a) Different modes of attachment of glycerol on Re species of the Re3O6H2 cluster and (b) mechanism for glycerol hydrogenolysis on the Ir-ReOx catalyst[105]

图13. Pt-WOx催化剂上1,2-二元醇脱除2号位羟基的碳氧鎓离子机理[107]

Figure 13. Oxocarbenium mechanism for 1,2-diols hydrodeoxygenation over Pt-WOx catalyst[107]

图14. Pt-WOx催化剂上甘油氢解至1,3-丙二醇的烯醇中间体机理

Figure 14. Enol mechanism for glycerol hydrogenolysis to 1,3-PrD over Pt-WOx catalysts

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生物质基多元醇的多相催化选择性氢解^★

Heterogeneous Catalysts for Selective Hydrogenolysis of Biomass-derived Polyols^★

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生物质基多元醇的多相催化选择性氢解★

Heterogeneous Catalysts for Selective Hydrogenolysis of Biomass-derived Polyols★

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摘要/Abstract

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生物质基多元醇的多相催化选择性氢解^★

Heterogeneous Catalysts for Selective Hydrogenolysis of Biomass-derived Polyols^★