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使用钌离子催化氧化法氧化多核芳烃:芳环数在反应动力学和产物分布中的作用。

Oxidation of Polynuclear Aromatic Hydrocarbons using Ruthenium-Ion-Catalyzed Oxidation: The Role of Aromatic Ring Number in Reaction Kinetics and Product Distribution.

作者信息

Nowicka Ewa, Clarke Tomos J, Sankar Meenakshisundaram, Jenkins Robert L, Knight David W, Golunski Stanislaw, Hutchings Graham J, Willock David J, Francisco Manuel, Taylor Stuart H

机构信息

Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.

ExxonMobil, Research & Engineering Company, 1545 Route 22 East, Annandale, New Jersey, 08801, USA.

出版信息

Chemistry. 2018 Jan 12;24(3):655-662. doi: 10.1002/chem.201704133. Epub 2017 Dec 11.

DOI:10.1002/chem.201704133
PMID:29131412
Abstract

Oxidation of aromatic hydrocarbons with differing numbers of fused aromatic rings (2-5), have been studied in two solvent environments (monophasic and biphasic) using ruthenium-ion-catalyzed oxidation (RICO). RICO reduces the aromaticity of the polyaromatic core of the molecule in a controlled manner by selective oxidative ring opening. Moreover, the nature of the solvent system determines the product type and distribution, for molecules with more than two aromatic rings. Competitive oxidation between substrates with different numbers of aromatic rings has been studied in detail. It was found that the rate of polyaromatic hydrocarbon oxidation increases with the number of fused aromatic rings. A similar trend was also identified for alkylated aromatic hydrocarbons. The proof-of-concept investigation provides new insight into selective oxidation chemistry for upgrading of polyaromatic molecules.

摘要

使用钌离子催化氧化(RICO),在两种溶剂环境(单相和双相)中研究了具有不同稠合芳环数(2 - 5)的芳烃的氧化反应。RICO通过选择性氧化开环以可控方式降低分子多芳核的芳香性。此外,对于具有两个以上芳环的分子,溶剂体系的性质决定了产物类型和分布。已详细研究了具有不同芳环数的底物之间的竞争氧化。结果发现,多环芳烃的氧化速率随着稠合芳环数的增加而增加。对于烷基化芳烃也发现了类似的趋势。该概念验证研究为多芳族分子升级的选择性氧化化学提供了新的见解。

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