期刊
ORGANIC PROCESS RESEARCH & DEVELOPMENT
卷 26, 期 9, 页码 2674-2684出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.2c00108
关键词
Birch reduction; electroreduction; electrochemistry; dearomatization; continuous flow; Taylor vortex reactor
资金
- UKRI Programme Grant [EP/P013341/1]
- University of Nottingham EPSRC Impact Acceleration Account
- EPSRC Doctoral Prize Fellowship Fund
The development of a single-pass electrochemical Birch reduction in a small footprint electrochemical reactor is reported, achieving high selectivity and productivity by varying the current and solution composition.
We report the development of a single-pass electrochemical Birch reduction carried out in a small footprint electrochemical Taylor vortex reactor with projected productivities of >80 g day(-1) (based on 32.2 mmol h(-1)), using a modified version of our previously reported reactor [Org. Process Res. Dev. 2021, 25, 7, 1619-1627], consisting of a static outer electrode and a rapidly rotating cylindrical inner electrode. In this study, we used an aluminum tube as the sacrificial outer electrode and stainless steel as the rotating inner electrode. We have established the viability of using a sacrificial aluminum anode for the electrochemical reduction of naphthalene, and by varying the current, we can switch between high selectivity (>90%) for either the single ring reduction or double ring reduction with >80 g day(-1) projected productivity for either product. The concentration of LiBr in solution changes the fluid dynamics of the reaction mixture investigated by computational fluid dynamics, and this affects equilibration time, monitored using Fourier transform infrared spectroscopy. We show that the concentrations of electrolyte (LiBr) and proton source (dimethylurea) can be reduced while maintaining high reaction efficiency. We also report the reduction of 1-aminonaphthalene, which has been used as a precursor to the API Ropinirole. We find that our methodology produces the corresponding dihydronaphthalene with excellent selectivity and 88% isolated yield in an uninterrupted run of >8 h with a projected productivity of >100 g day(-1).
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据