炔醇选择加氢催化剂研究进展

doi:10.1016/S1872-2067(20)63773-1

催化学报 ›› 2021, Vol. 42 ›› Issue (12): 2105-2121.DOI: 10.1016/S1872-2067(20)63773-1

炔醇选择加氢催化剂研究进展

陈霄, 石闯, 梁长海^*()

大连理工大学化工学院, 精细化工国家重点实验室&先进材料与催化工程实验室, 辽宁大连116024

收稿日期:2020-12-02 接受日期:2020-12-02 出版日期:2021-12-18 发布日期:2021-05-06
通讯作者: 梁长海
基金资助:
国家重点研发计划项目(2016YFB0600305);国家自然科学基金(21573031);国家自然科学基金(21403026);国家自然科学基金(21073023);大连市科技创新基金(2019J12GX028);大连市科技创新基金(2018RQ09);2020年中-法“蔡元培”交流合作项目

Highly selective catalysts for the hydrogenation of alkynols: A review

Xiao Chen, Chuang Shi, Changhai Liang^*()

State Key Laboratory of Fine Chemicals, Laboratory of Advanced Materials and Catalytic Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, China

Received:2020-12-02 Accepted:2020-12-02 Online:2021-12-18 Published:2021-05-06
Contact: Changhai Liang
About author:* Tel/Fax: +86-411-84986353; E-mail: changhai@dlut.edu.cn
Supported by:
National Key Research & Development Program of China(2016YFB0600305);National Natural Science Foundation of China(21573031);National Natural Science Foundation of China(21403026);National Natural Science Foundation of China(21073023);Science and Technology Innovation Fund in Dalian City(2019J12GX028);Science and Technology Innovation Fund in Dalian City(2018RQ09);Project Partenariats Hubert Curien (PHC) Cai Yuanpei grant

摘要/Abstract

摘要：

炔醇选择加氢制备相应的烯醇在医药、农药、食品添加剂、香精、香料和聚合物单体等众多高端精细化学品合成中是一个非常重要的化工过程. 通过一系列复杂的平行和连续的反应, 炔醇可加氢生产若干个关键中间体. 提高对烯醇的选择性和保持催化剂的效率是工业生产的关键, 也是一个巨大的挑战. 迄今为止, 各种有效的贵金属和非贵金属催化剂得到了广泛的发展, 尤其是钯基和镍基多相催化剂取得了显著进展. 从经典的Lindlar催化剂和Raney-Ni催化剂到生物基金属催化新材料, 本文系统综述了近几十年炔醇选择加氢催化剂的设计, 从催化剂本身的金属活性中心、助剂(第二金属、有机配体和稳定剂)的作用、载体的性质(孔结构、酸碱性、金属与载体强相互作用)以及反应条件等因素对催化活性、目标产物的选择性和稳定性的影响进行了系统的综述. 借助先进的表征技术、理论计算和实验研究, 本文还阐述了炔醇选择加氢反应的机理. 研究发现: (1)在所有贵金属催化剂中, Pd基催化剂对炔醇半加氢制烯醇的效率最高, 且选择性最好. 稳定剂和抑制剂的加入可以提高中间体的选择性, 但在一定程度上降低了催化活性. 此外, Zn, In和Cu等第二金属的掺杂可以调节金属Pd的几何效应和电子结构, 从而调节底物和中间产物的吸附, 并抑制过度加氢. 与传统的Lindlar型催化剂相比, 这种Pd基合金或金属间化合物可广泛应用于炔醇的选择性加氢反应, 显著提高烯醇的选择性, 且不需要引入有毒添加剂. (2) Ni基材料作为可替代贵金属催化剂, 可分别实现炔醇的高选择性加氢制备烯醇或烷醇. 然而, 与贵金属催化剂相比, 其反应条件相对苛刻. 炔醇加氢产物分布很大程度上取决于助剂的引入和载体的酸性. 此外, 碳物种易沉积在Ni表面造成活性位点被覆盖, 且在水热环境下Ni颗粒因团聚而失活, 因此, 用于炔醇选择加氢反应的镍基催化剂稳定性仍有待提高.

尽管炔醇选择加氢反应在学术界和工业界都有广泛研究, 但对于这些催化体系, 特别是催化剂的结构性能关系和反应机理, 仍有待进一步明确. (1)原位表征技术和理论计算的发展, 将有助于人们理解炔醇选择性加氢的催化过程, 并指导研究者根据炔醇加氢的特点设计出具有良好选择性的高效催化剂. (2)烯醇类产品一般应用于医药中间体和高分子单体, 对产品纯度要求较高. 因此, 在不引入有毒添加剂的情况下, 设计高效、高选择性催化剂至关重要. (3)水相或醇相中炔醇选择加氢反应对催化剂的水热稳定性有很高的要求. 通过锚定和包覆来增强金属与载体的相互作用, 抑制金属纳米粒子的聚集和流失是一种有效的手段. 此外, 在炔醇选择加氢反应中引入耐水载体可以有效提高催化剂的稳定性. (4)短碳链炔醇催化选择加氢反应一直是研究的热点. 然而, 关于长碳链炔醇的选择加氢反应过程, 国内外报道相对较少. 基于长碳链炔醇底物分子的空间位阻效应, 有必要设计具有特殊孔道结构的选择加氢催化剂. (5)目前, 绝大多数炔醇选择加氢过程还处于间歇性操作. 随着市场对烯醇的需求不断增加, 为了获得高品质的产品, 连续化操作将是一个必然趋势.

关键词: 炔醇, 烯醇, 选择加氢, 金属催化剂, 催化剂设计

Abstract:

The semi-hydrogenation of alkynols to enols is a crucial process in the production of pharmaceuticals, agrochemicals, fragrances, and flavors that involves a complex set of parallel and consecutive isomerization and hydrogenation reactions and proceeds via several key intermediates. In view of the industrial importance of large-scale enol production through alkynol hydrogenation, various noble and non-noble metal (e.g., Ni and Pd)-based catalysts promoting this transformation have been developed. This paper reviews the design of highly selective catalysts for the semi-hydrogenation of alkynols, focusing on the role of additives, second metals, catalyst supports, and reaction conditions and combining catalytic reaction kinetics with theoretical calculations to establish the reaction mechanism and the decisive factors for boosting selectivity. Finally, a strategy for designing highly efficient and selective catalysts based on the characteristics of aqueous-phase alkynol hydrogenation is proposed.

Key words: Alkynol, Enol, Selective hydrogenation, Metal-based catalyst, Catalyst design

陈霄, 石闯, 梁长海. 炔醇选择加氢催化剂研究进展[J]. 催化学报, 2021, 42(12): 2105-2121.

Xiao Chen, Chuang Shi, Changhai Liang. Highly selective catalysts for the hydrogenation of alkynols: A review[J]. Chinese Journal of Catalysis, 2021, 42(12): 2105-2121.

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图/表 27

Table 1 Schematic alkynol hydrogenation pathways.

No.	Alkynol	Schematic hydrogenation pathway
1	3-Hexyn-1-ol
2	3-Phenyl-2-propyn-1-ol
3	2-Butyne-1,4-diol
4	2-Methyl-3-butyne-2-ol
5	1,1-Diphenyl-2-propyn-1-ol
6	Dehydroisophytol

Scheme 1 General mechanism of alkyne hydrogenation.

Table 2 Performance of previously reported Pd-based catalysts for the selective hydrogenation of alkynols.

No.	Catalyst	Substrate	T (°C)	P (MPa)	Alkynol conversion (%)	Enol selectivity (%)	Ref.
1	PVP-Pd	2-Butyne-1,4-diol	50	2	100	96	[29]
2	Pd/CaCO₃	2-Butyne-1,4-diol	50	2.1	—	99.5	[10]
3	Pd/CaCO₃-NH₃	2-Butyne-1,4-diol	50	2.4	—	100	[11]
4	Pd/CaCO₃	3-Hexyn-1-ol	-10	0.1	100	95.3	[30]
5	PdPb/CaCO₃	2-Methyl-3-butyn-2-ol	80	0.1	99	95	[15]
6	Pd/ACF	2-Butyne-1,4-diol	30	0.6	80	97	[34]
7	Pd/C	2-Butyne-1,4-diol	65	0.3	65	73	[35]
8	Pd/C	2-Butyne-1,4-diol	50	2.1	—	99.2	[10]
9	c-Pd/C	2-Methyl-3-butyn-2-ol	20	0.1	24-35	100	[12]
10	Pd NCs@NCM	3-Phenyl-2-propyn-1-ol	45	H₂ balloon	93.1	97.7	[36]
11	c-Pd/TiS	3-Hexyn-1-ol	30	0.3	97	99	[32]
12	c-Pd/TiS	2-Methyl-3-butyn-2-ol	30	0.3	97	95	[32]
13	Pd/SiO₂	3-Hexyn-1-ol	RT	0.1-0.2	85	80	[38]
14	Pd/GPMHS40	3-Hexyn-1-ol	40	—	100	>90	[39]
15	Pd@MonoSil-ArSO₃	3-Hexyn-1-ol	RT	0.115	94 ± 1	94 ± 1	[40]
16	Pd/SiO₂-Schiff	2-Butyne-1,4-diol	50	2	95.2	100	[41]
17	Pd/Al₂O₃	2-Butyne-1,4-diol	60	0.45	90.8	95.3	[42]
18	Pd/γ-Al₂O₃	2-Butyne-1,4-diol	50	0.6	100	94	[43]
19	Pd/Mg(Al)O	2-Butyne-1,4-diol	50	0.6	90	88	[46]
20	Pd@TiO₂	3-Hexyn-1-ol	RT	—	61.4	63	[47]
21	Pd/TiO₂	3-Hexyn-1-ol	40	0.2	100	60-87	[48]
22	Pd/ZnO	2-Methyl-3-butyn-2-ol	130	1	10	96	[50]
23	Pd@Cu₂O	3-Phenyl-2-propyn-1-ol	20	0.1	96.1	91.0	[36]
24	Pd/ZPGly20	2-Butyne-1,4-diol	RT	0.1	98.3	97.3	[52]
		2-Methyl-3-butyn-2-ol	RT	0.1	75.3	94.9
		3-Hexyn-1-ol	RT	0.1	99.6	90.6
		3-Phenyl-2-propyn-1-ol	RT	0.1	95	93.7
25	Pd/FCN resin	2-Butyne-1,4-diol	22	—	90	94.7	[53]
26	Pd/OFP resin	2-Butyne-1,4-diol	22	0.1	90	85	[54]
27	D/Pd	3-Hexyn-1-ol	—	0.1	75	80	[55]
28	Pd@borate	2-Butyne-1,4-diol	RT	0.176	93.3	75.5	[56]
		2-Methyl-3-butyn-2-ol	RT	0.14	92	93.9
		3-Hexyn-1-ol	RT	0.126	99.5	94.5
		3-Phenyl-2-propyn-1-ol	RT	0.15	96.2	79
29	Pd/MOF-5	2-Butyne-1,4-diol	20	0.1	95	95	[57]
30	Pd/MIL-101(Cr)	2-Butyne-1,4-diol	50	0.5	100	94	[58]
31	PVP-Pd/ZIF-8	2-Butyne-1,4-diol	50	2	99.7	97.5	[59]
32	PdCu/CaCO₃	3-Hexyn-1-ol	-10	0.1	100	95.7	[30]
33	PdAu/SiO₂	3-Hexyn-1-ol	20	2	15	100	[38]
34	PdCu/ZnO	Dehydroisophytol	80	0.4	99	95-97	[60]
35	PdAg/ZnO	Dehydroisophytol	80	0.4	99	97-98	[60]
36	PdAu	2-Methyl-3-butyn-2-ol	30	—	98.2	98.9	[62]
37	PdBi/SiO₂	2-Methyl-3-butyn-2-ol	50	0.1	100	94-96	[63]
38	PdZn/Al₂O₃	2-Methyl-3-butyn-2-ol	100	0.1	25	90	[66]
39	PdZn/TiO₂	2-Methyl-3-butyn-2-ol	60	0.5	95	81.5-88.9	[68]
40	Pd/ZnO/SMF	2-Butyne-1,4-diol	80	1.5	99	99	[69]
41	Pd/ZnO/SMF	2-Methyl-3-butyn-2-ol	35	0.5	99.9	94.5	[69]
42	PdIn/In₂O₃	2-Methyl-3-butyn-2-ol	80	0.1	99	95	[15]

Table 2 Performance of previously reported Pd-based catalysts for the selective hydrogenation of alkynols.

No.	Catalyst	Substrate	T (°C)	P (MPa)	Alkynol conversion (%)	Enol selectivity (%)	Ref.
1	PVP-Pd	2-Butyne-1,4-diol	50	2	100	96	[29]
2	Pd/CaCO₃	2-Butyne-1,4-diol	50	2.1	—	99.5	[10]
3	Pd/CaCO₃-NH₃	2-Butyne-1,4-diol	50	2.4	—	100	[11]
4	Pd/CaCO₃	3-Hexyn-1-ol	-10	0.1	100	95.3	[30]
5	PdPb/CaCO₃	2-Methyl-3-butyn-2-ol	80	0.1	99	95	[15]
6	Pd/ACF	2-Butyne-1,4-diol	30	0.6	80	97	[34]
7	Pd/C	2-Butyne-1,4-diol	65	0.3	65	73	[35]
8	Pd/C	2-Butyne-1,4-diol	50	2.1	—	99.2	[10]
9	c-Pd/C	2-Methyl-3-butyn-2-ol	20	0.1	24-35	100	[12]
10	Pd NCs@NCM	3-Phenyl-2-propyn-1-ol	45	H₂ balloon	93.1	97.7	[36]
11	c-Pd/TiS	3-Hexyn-1-ol	30	0.3	97	99	[32]
12	c-Pd/TiS	2-Methyl-3-butyn-2-ol	30	0.3	97	95	[32]
13	Pd/SiO₂	3-Hexyn-1-ol	RT	0.1-0.2	85	80	[38]
14	Pd/GPMHS40	3-Hexyn-1-ol	40	—	100	>90	[39]
15	Pd@MonoSil-ArSO₃	3-Hexyn-1-ol	RT	0.115	94 ± 1	94 ± 1	[40]
16	Pd/SiO₂-Schiff	2-Butyne-1,4-diol	50	2	95.2	100	[41]
17	Pd/Al₂O₃	2-Butyne-1,4-diol	60	0.45	90.8	95.3	[42]
18	Pd/γ-Al₂O₃	2-Butyne-1,4-diol	50	0.6	100	94	[43]
19	Pd/Mg(Al)O	2-Butyne-1,4-diol	50	0.6	90	88	[46]
20	Pd@TiO₂	3-Hexyn-1-ol	RT	—	61.4	63	[47]
21	Pd/TiO₂	3-Hexyn-1-ol	40	0.2	100	60-87	[48]
22	Pd/ZnO	2-Methyl-3-butyn-2-ol	130	1	10	96	[50]
23	Pd@Cu₂O	3-Phenyl-2-propyn-1-ol	20	0.1	96.1	91.0	[36]
24	Pd/ZPGly20	2-Butyne-1,4-diol	RT	0.1	98.3	97.3	[52]
		2-Methyl-3-butyn-2-ol	RT	0.1	75.3	94.9
		3-Hexyn-1-ol	RT	0.1	99.6	90.6
		3-Phenyl-2-propyn-1-ol	RT	0.1	95	93.7
25	Pd/FCN resin	2-Butyne-1,4-diol	22	—	90	94.7	[53]
26	Pd/OFP resin	2-Butyne-1,4-diol	22	0.1	90	85	[54]
27	D/Pd	3-Hexyn-1-ol	—	0.1	75	80	[55]
28	Pd@borate	2-Butyne-1,4-diol	RT	0.176	93.3	75.5	[56]
		2-Methyl-3-butyn-2-ol	RT	0.14	92	93.9
		3-Hexyn-1-ol	RT	0.126	99.5	94.5
		3-Phenyl-2-propyn-1-ol	RT	0.15	96.2	79
29	Pd/MOF-5	2-Butyne-1,4-diol	20	0.1	95	95	[57]
30	Pd/MIL-101(Cr)	2-Butyne-1,4-diol	50	0.5	100	94	[58]
31	PVP-Pd/ZIF-8	2-Butyne-1,4-diol	50	2	99.7	97.5	[59]
32	PdCu/CaCO₃	3-Hexyn-1-ol	-10	0.1	100	95.7	[30]
33	PdAu/SiO₂	3-Hexyn-1-ol	20	2	15	100	[38]
34	PdCu/ZnO	Dehydroisophytol	80	0.4	99	95-97	[60]
35	PdAg/ZnO	Dehydroisophytol	80	0.4	99	97-98	[60]
36	PdAu	2-Methyl-3-butyn-2-ol	30	—	98.2	98.9	[62]
37	PdBi/SiO₂	2-Methyl-3-butyn-2-ol	50	0.1	100	94-96	[63]
38	PdZn/Al₂O₃	2-Methyl-3-butyn-2-ol	100	0.1	25	90	[66]
39	PdZn/TiO₂	2-Methyl-3-butyn-2-ol	60	0.5	95	81.5-88.9	[68]
40	Pd/ZnO/SMF	2-Butyne-1,4-diol	80	1.5	99	99	[69]
41	Pd/ZnO/SMF	2-Methyl-3-butyn-2-ol	35	0.5	99.9	94.5	[69]
42	PdIn/In₂O₃	2-Methyl-3-butyn-2-ol	80	0.1	99	95	[15]

Fig. 2. Pd NPs supported on hierarchically porous silica grafted with polymethylhydrosiloxane for the selective hydrogenation of 3-hexyn-1-ol. Reprinted with permission from Ref. [39]. Copyright © 2017, American Chemical Society.

Fig. 4. Schematic fabrication of Pd/Fe-Co-Ni LDH nanocages and their use as catalysts for MBY hydrogenation. Reprinted with permission from Ref. [49]. Copyright © 2020 Elsevier B.V. All rights reserved.

Fig. 5. Synthesis (top) and images of MonoBor (left), Pd(NO3)2-impregnated MonoBor (center), and Pd@MonoBor (right) monolithic columns (i.d. = 3 mm, length = 25 mm). Reprinted with permission from Ref. [53]. Copyright © 2013 Elsevier Inc. All rights reserved.

Fig. 6. Kinetic data for BYD hydrogenation over (a) 1 wt% PVP-Pd@ZIF-8 and (b) PVP-Pd colloid. Reprinted from Ref. [59] with permission from the Royal Society of Chemistry.

Fig. 10. Catalytic performances of Pd-In/In2O3-250 and PdPb/CaCO3 for the semi-hydrogenation of MBY. (a) Time-conversion and (b) selectivity-conversion profiles. Reprinted with permission from Ref. [15]. Copyright @2019, the Royal Society of Chemistry.

Table 3 Activities of Pt-based catalysts for the selective hydrogenation of BYD.

No.	Catalyst	T (°C)	P (MPa)	Alkynol conversion (%)	Enol selectivity (%)	Ref.
1	Pt/CaCO₃	50	2.4	~95	83	[72]
2	Pt/CaCO₃-NH₃	50	2.4	—	100	[72]
3	Pt-Li/CaCO₃	50	2.4	99.6	83	[73]
4	Pt-Cs/CaCO₃	50	2.4	—	99	[73]
5	PtCu/Cu_xFe_yO@C	120	4	100	96.1	[74]
6	Pt@ZIF-8	120	3	100	94	[75]
7	Pt/SBA-15	120	3	~100	68	[75]
8	Pt nano-sol	120	3	~95	68	[75]
9	Pt/SiC	100	1	96	96	[76]
10	Pt/bovine-bone	55	0.6	~100	83	[77]
11	Pt/PANI	22	0.1	85	75	[78]
12	Pt/P4VP	22	0.1	85	80	[79]
13	Pt/graphite	40	0.5	70	~55	[80]

Fig. 11. One-step synthesis of the Pt@ZIF-8 catalyst for the selective hydrogenation of BYD to BED. Reprinted with permission from Ref. [75]. Copyright © 2016 Dalian Institute of Chemical Physics, Chinese Academy of Sciences.

Fig. 12. Schematic structural evolution of the Pt/SiC catalyst for the selective hydrogenation of BYD to BED. Reprinted from Ref. [76] with permission from the Royal Society of Chemistry.

Fig. 13. (a) MBY and MBE conversions after 1-h hydrogenation over Au@Au6Pd1, Au@Au4Pd1, Au@Au3Pd1, Au@Au2Pd1, Au@Au2Pd3, Au@Au1Pd4, and Au@Au0Pd5 at 30 °C. (b) Semi-hydrogenation selectivity of different nanocubes for MBE at a conversion of ~95%. Time-dependent hydrogenation conversions of MBY and MBE selectivities of Au@Au6Pd1 (c), Au@Au4Pd1 (d), and Au@Au2Pd1 (e) nanocubes. (f) Four-cycle durability test of Au@Au4Pd1 nanocubes. Reprinted with permission from Ref. [62]. Copyright 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Table 4 Activities of previously reported Ni-based catalysts for the selective hydrogenation of BYD.

No.	Catalyst	Reactor	T (°C)	P (MPa)	BYD conversion (%)	Selectivity (%)		Ref.
No.	Catalyst	Reactor	T (°C)	P (MPa)	BYD conversion (%)	BDO	BED	Ref.
1	Raney Ni	batch	70	6.9	100	93	trace	[83]
2	Raney Ni	CSTR	70	6.9	100	98-99	trace	[83]
3	Raney Ni	fixed bed	120	13.8	100	95.3	trace	[84]
4	Raney Ni	batch	40	atmospheric pressure	100	91.6	trace	[85]
5	Raney 350-NiSi_x	fixed bed	90	3	84.8	9.3	80.4	[88]
6	Ni/AlPO₄-P	batch	40	0.3-0.7	10.3 μmol s^-1 g^-1	—	92.5	[89]
7	NiCu/AlPO₄-P	batch	40	0.3-0.7	9.51 μmol s^-1 g^-1	—	97.9	[89]
8	Ni-3Fe/Al₂O₃	slurry-bed	120	4	99.9	0.5	97.3	[90]
9	Ni/Al₂O₃	slurry-bed	120	4	65	62	30	[91]
10	Ni/Al₂O₃-SiO₂	slurry-bed	120	4	93.6	75.2	19.5	[91]
11	9Ni1Cu@SiO₂	batch	50	1	100	90.5	—	[92]

Fig. 14. Hydrogenation of BYD over the Ni33 catalyst in STR mode. Reaction conditions: T = 70 °C, P = 6.89 MPa, catalyst mass = 9.6 g, aqueous BYD volume = 40 mL (3.09 mM/mL), stir rate = 1900 rpm. Reprinted with permission from Ref. [84]. Copyright © 2017, American Chemical Society.

Fig. 15. Effect of contact time on BYD conversion (a) and the selectivities for BED and BDO (b) formation over Raney Ni-Si catalysts at 3 MPa H2 and 90 °C. Reprinted with permission from Ref. [88]. Copyright © 2014, Springer Nature.

Fig. 16. Results of stability testing for Ni/Al2O3 and Ni-3Fe/Al2O3: Effects of run time on (a) BYD conversion and (b) cis-BED selectivity. Reproduced with permission from Ref. [90]. Copyright @2019, the Royal Society of Chemistry.

Fig. 17. Proposed mechanism of BYD hydrogenation over phyllosilicate-derived NiCu@SiO2 catalysts. Reprinted with permission from Ref. [92]. Copyright 2019, WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Fig. 18. Effect of alkyne conversion on BYD selectivity for four different Pt catalysts with increasing occupation/blockage of defect sites. Reprinted with permission from ref. [80]. Copyright © 2012, American Chemical Society.

Fig. 19. (a) Comparison of metal-based catalysts in terms of their specific activity and selectivity for BED formation during BYD hydrogenation. (b) Detailed view of data enclosed in the red box of (a).

Fig. 20. A: Hydrogenation of BYD over catalyst RN1-32 in STR mode. (H2 Uptake vs. Time.) B: Hydrogenation of BYD over catalyst RN1-32 in STR mode. (Concentration vs. Time.) Reprinted with permission from Ref. [84]. Copyright © 2017, American Chemical Society.

Fig. 21. Natural bond orbital charge (qNBO) (left) and changes in the natural electron configuration (ΔnNEC) before and after BD adsorption on Ni22 (111) (right). The color of atoms in the left panel changes from red (positively charged) to green (negatively charged). Reprinted with permission from Ref. [96]. Copyright © 2012, Elsevier B.V. All rights reserved.

Fig. 22. Mechanisms of hydrogenation on the Pd9(H)2 cluster for BYD as a model reactant. Both reaction paths are representative of all investigated reactants. Upper and lower diagrams illustrate C≡C to C=C and C=C to C-C hydrogenation, respectively. Reprinted with permission from Ref. [97]. Copyright © 2014, American Chemical Society.

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炔醇选择加氢催化剂研究进展

Highly selective catalysts for the hydrogenation of alkynols: A review

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