镍配合物催化1-丁醇高效制备2-乙基-1-己醇

doi:10.1016/S1872-2067(26)64997-2

催化学报 ›› 2026, Vol. 84: 368-374.DOI: 10.1016/S1872-2067(26)64997-2

镍配合物催化1-丁醇高效制备2-乙基-1-己醇

朱鑫涛^a^,¹, 夏秋玲^a^,¹, 胡越^b^,^c(), 谢银君^b^,^c()

^a 宁波大学材料科学与化学工程学院, 浙江宁波 315201
^b 中国科学院宁波材料技术与工程研究所, 全省先进燃料电池与电解池技术重点实验室, 浙江宁波 315201
^c 中国科学院大学, 北京 100049

收稿日期:2025-09-15 接受日期:2025-11-12 出版日期:2026-05-18 发布日期:2026-04-16
通讯作者: *电子信箱: huyue@nimte.ac.cn (胡越),
xieyinjun@nimte.ac.cn (谢银君).
作者简介:¹共同第一作者.
基金资助:
国家自然科学基金(22571311);宁波市“3315计划” C类创新团队(2020A-32-C)

Highly efficient upgrading of 1-butanol into 2‐ethyl‐1‐hexanol catalyzed by nickel pincer complexes

Xintao Zhu^a^,¹, Qiuling Xia^a^,¹, Yue Hu^b^,^c(), Yinjun Xie^b^,^c()

^a School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315201, Zhejiang, China
^b Zhejiang Key Laboratory of Advanced Fuel Cells and Electrolyzers Technology, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, Zhejiang, China
^c University of Chinese Academy of Sciences, Beijing 100049, China

Received:2025-09-15 Accepted:2025-11-12 Online:2026-05-18 Published:2026-04-16
Contact: * E-mail: huyue@nimte.ac.cn (Y. Hu),
xieyinjun@nimte.ac.cn (Y. Xie).
About author:¹Contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22571311);3315 Program of Ningbo(2020A-32-C)

摘要/Abstract

摘要：

2-乙基-1-己醇(2-EH)是一种重要的化工中间体, 广泛应用于增塑剂、涂料、润滑剂等领域. 其传统工业生产路线依赖化石资源, 且涉及多步合成, 存在原子经济性差和环境压力大等问题. 利用生物质衍生的1-丁醇通过Guerbet反应合成2-EH, 因其原料可再生、原子经济性高且仅副产水, 被视为一种极具潜力的绿色替代路线. 然而, 该反应面临热力学和动力学挑战, 如醇脱氢步骤能垒较高、后续羟醛缩合与加氢步骤选择性难以控制等, 导致转化率和选择性普遍较低. 现有催化体系多依赖于贵金属(如Ru, Ir)催化剂, 并常需添加溶剂, 且难以同时实现高转化率和高催化周转数(TON). 开发能够媲美甚至超越贵金属催化剂性能的丰产金属催化剂, 对于实现长链醇的可持续生产具有重要意义.

本研究创新性地设计并合成了一类基于喹啉骨架的新型PNNⁱ^PrH型钳形镍配合物, 并成功将其应用于1-丁醇及其它直链醇的Guerbet反应制备相应的长链醇. 该催化体系在无溶剂条件下, 以[Ni]-1为催化剂、催化量的NaH为碱, 于150 ºC氮气氛围中反应, 即可高效催化1-丁醇转化为2-EH. 通过系统优化配体结构、镍前体、碱、反应时间及反应器体积等关键参数, 最终实现了最高86%的1-丁醇转化率和80%的2-EH收率. 尤为突出的是, 该反应在极低催化剂负载量(0.003 mol%)下仍可顺利进行, TON高达20533, 展现了较好的催化效率和选择性, 甚至超越了绝大多数已报道的贵金属催化体系. 动力学研究表明, 反应无诱导期, 反应速率在后期因底物与碱的消耗以及副产物水的累积而下降. 催化剂回收实验表明, 蒸馏回收原料及产物后剩余的催化剂残余物仍具备较高催化活性, 证明其良好的重复使用性和放大潜力. 底物拓展实验表明, 该体系对一系列直链醇(如1-丙醇、1-戊醇、1-己醇等)均具有良好适用性, 能高效、高选择性地将其转化生成相应的长链醇(C₆‒C₂₄). 基于前期研究基础和文献报道, 本文提出了合理的催化循环机理: 首先正丁氧阴离子取代乙酸根后与镍发生配位; 随后通过镍与氮原子的协同作用使正丁醇脱氢生成镍氢物种和正丁醛; 正丁醛经历碱促进的羟醛缩合生成关键中间体2-乙基-2-己烯醛, 随后被镍氢物种还原得到目标产物2-EH, 并使镍催化剂再生, 完成催化循环.

综上, 本研究开发了一种高效的镍催化体系, 可用于将1-丁醇及相关短链醇升级转化为高附加值的长链(C₆‒C₂₄)醇产品, 同时实现了高转化率和高催化周转数, 为从可再生原料可持续生产高附加值长链醇提供了高效、经济且环境友好的新策略, 显著推动了丰产金属催化剂在借氢反应及绿色催化合成领域的应用.

关键词: 1-丁醇升级, 镍钳形配合物, 2-乙基-1-己醇, Guerbet反应, 均相催化

Abstract:

The Guerbet reaction of biomass-derived 1-butanol offers a sustainable route to valuable 2-ethyl-1-hexanol (2-EH), yet faces significant challenges, including low conversions, poor selectivity and reliance on noble metal catalysts and additional solvents. Herein, we report a highly efficient nickel pincer-catalyzed system that achieves new records of 86% 1-butanol conversion and 80% 2-EH yield. This constitutes the first homogeneous non-noble metal catalyst for 1-butanol upgrading to higher alcohols with both high conversion and high TON. Furthermore, the protocol demonstrates broad applicability, enabling selective valorization of diverse alcohol feedstocks to their elongated counterparts.

Key words: 1-Butanol upgrading, Nickel pincer complex, 2‐Ethyl‐1‐hexanol, Guerbet process, Homogeneous catalysis

朱鑫涛, 夏秋玲, 胡越, 谢银君. 镍配合物催化1-丁醇高效制备2-乙基-1-己醇[J]. 催化学报, 2026, 84: 368-374.

Xintao Zhu, Qiuling Xia, Yue Hu, Yinjun Xie. Highly efficient upgrading of 1-butanol into 2‐ethyl‐1‐hexanol catalyzed by nickel pincer complexes[J]. Chinese Journal of Catalysis, 2026, 84: 368-374.

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Entry	[Ni]-1 (%)	Base	Conv.^b (%)	Yield^b (%)	TON of Ni ^c
1	[Ni]-1 (0.1 mol%)	NaH	53	47	534
2	[Ni]-1 (0.1 mol%)	^tBuOK	41	41	405
3	[Ni]-1 (0.1 mol%)	^tBuONa	44	44	438
4	[Ni]-1 (0.1 mol%)	CH₃ONa	30	27	302
5	[Ni]-1 (0.1 mol%)	EtONa	48	34	475
6	[Ni]-1 (0.1 mol%)	NaOH	52	44	520
7	[Ni]-1 (0.1 mol%)	K₂CO₃	22	12	224
8	[Ni]-1 (0.1 mol%)	LiH	26	17	258
9 ^d	[Ni]-1 (0.1 mol%)	NaH	61	55	614
10 ^d,e	[Ni]-1 (0.1 mol%)	NaH	72	65	720
11 ^d,e,f	[Ni]-1 (0.1 mol%)	NaH	86	80	855
12 ^f,g,h	[Ni]-1 (0.1 mol%)	NaH	64	54	635
13 ^e,f,i	[Ni]-1 (0.005 mol%)	NaH	71	67	14120
14 ^e,f,i	[Ni]-1 (0.003 mol%)	NaH	62	55	20533
15 ^d,e,f,j	Recovered catalyst	NaH	35	27	345

Entry	[Ni]-1 (%)	Base	Conv.^b (%)	Yield^b (%)	TON of Ni ^c
1	[Ni]-1 (0.1 mol%)	NaH	53	47	534
2	[Ni]-1 (0.1 mol%)	^tBuOK	41	41	405
3	[Ni]-1 (0.1 mol%)	^tBuONa	44	44	438
4	[Ni]-1 (0.1 mol%)	CH₃ONa	30	27	302
5	[Ni]-1 (0.1 mol%)	EtONa	48	34	475
6	[Ni]-1 (0.1 mol%)	NaOH	52	44	520
7	[Ni]-1 (0.1 mol%)	K₂CO₃	22	12	224
8	[Ni]-1 (0.1 mol%)	LiH	26	17	258
9 ^d	[Ni]-1 (0.1 mol%)	NaH	61	55	614
10 ^d,e	[Ni]-1 (0.1 mol%)	NaH	72	65	720
11 ^d,e,f	[Ni]-1 (0.1 mol%)	NaH	86	80	855
12 ^f,g,h	[Ni]-1 (0.1 mol%)	NaH	64	54	635
13 ^e,f,i	[Ni]-1 (0.005 mol%)	NaH	71	67	14120
14 ^e,f,i	[Ni]-1 (0.003 mol%)	NaH	62	55	20533
15 ^d,e,f,j	Recovered catalyst	NaH	35	27	345

镍配合物催化1-丁醇高效制备2-乙基-1-己醇

Highly efficient upgrading of 1-butanol into 2‐ethyl‐1‐hexanol catalyzed by nickel pincer complexes

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