Solvent effects on heterogeneous catalysis in the selective hydrogenation of cinnamaldehyde over a conventional Pd/C catalyst†,Catalysis Science & Technology

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Solvent effects on heterogeneous catalysis in the selective hydrogenation of cinnamaldehyde over a conventional Pd/C catalyst†
Catalysis Science & Technology ( IF 4.4 ) Pub Date : 2018-06-21 00:00:00 , DOI: 10.1039/c8cy00943k
Yan Li _{1,

2,

3,

4,

5} , Haiyang Cheng _{1,

2,

3,

4,

5} , Weiwei Lin _{1,

2,

3,

4,

5} , Chao Zhang _{1,

2,

3,

4,

5} , Qifan Wu _{1,

2,

3,

4,

5} , Fengyu Zhao _{1,

2,

3,

4,

5} , Masahiko Arai _{1,

2,

3,

4,

5}

Affiliation

Solvent effects in the selective hydrogenation of an α,β-unsaturated aldehyde of cinnamaldehyde (CAL) were investigated under gas–liquid–solid reaction conditions. A conventional 5 wt% Pd/C catalyst and twelve organic solvents were used, including apolar solvents (three) and protic (two) and aprotic (seven) polar ones. The total rate of CAL hydrogenation strongly depended on the solvents used. The relationship between the rate of CAL hydrogenation observed and a few different solvent parameters was examined. The main product was hydrocinnamaldehyde (HCAL) with a selectivity of 80% or higher in most of the solvents examined except for pyridine and 4-methylpyridine. In these two solvents, the CAL hydrogenation was slow and the main product was changed to cinnamyl alcohol (COL) with a selectivity of about 60%. The addition of a small volume of pyridine to other solvents such as 2-propanol and tetrahydrofuran could change the rate of hydrogenation and switch the main product from HCAL to COL. Possible interactions among the solvents, CAL substrate, and Pd/C catalyst were examined by FTIR (attenuated total reflection (ATR-) and diffuse reflectance modes (DR-)) and TPD to discuss the solvent effects observed in the Pd-catalyzed heterogeneous CAL hydrogenation.

中文翻译：

在常规Pd / C催化剂上肉桂醛选择性加氢中，溶剂对非均相催化的影响†

在气-液-固反应条件下，研究了肉桂醛的α，β-不饱和醛（CAL）选择性加氢中的溶剂效应。使用常规的5 wt％Pd / C催化剂和十二种有机溶剂，包括非极性溶剂（三种）和质子性溶剂（两种）和非质子性溶剂（七种）。CAL加氢的总速率在很大程度上取决于所用的溶剂。检查了观察到的CAL加氢速率与一些不同溶剂参数之间的关系。主要产物是氢肉桂醛（HCAL），除吡啶和4-甲基吡啶外，在大多数所考察的溶剂中，其选择性为80％或更高。在这两种溶剂中，CAL加氢缓慢，主产物变为选择性的肉桂醇（COL），选择性约为60％。在其他溶剂（如2-丙醇和四氢呋喃）中加入少量吡啶可改变氢化速率，并将主要产物从HCAL转换为COL。通过FTIR（衰减全反射（ATR-）和漫反射模式（DR-））和TPD检查了溶剂，CAL底物和Pd / C催化剂之间可能的相互作用，以讨论在Pd催化的非均相CAL中观察到的溶剂效应氢化。

更新日期：2018-06-21

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