一級硝基芳烴藉由光催化以合成相對應芳香胺之研究

Photochemical Conversion of Primary Nitroarenes to Corresponding Aromatic Amines

黃樺宣(Hua-Hsuan Huang)

指導教授 ： 莊 敬

中原大學/理學院/化學研究所/碩士(2014年)

https://doi.org/10.6840/cycu201400763

摘要

本論文為一級硝基芳烴藉由光催化進行兩步一鍋化反應，以合成一級芳香胺之研究。研究中發現，反應於306 nm之紫外光時效率較佳；而Al2O3的酸鹼性質會對產率造成較大的影響。待反應完成，僅需以酸鹼萃取法分離產物，僅少數產物需再以管柱層析分離純化。研究中亦嘗試在無sensitizer的存在下，將一級硝基芳烴溶於異丙醇中，進行光還原反應還原以合成一級芳香胺。本研究也以連續流反應結合光催化改善了原來照光反應不易放大的問題，並縮短了反應所需的時間，提升反應效率。有別以往的文獻，實驗過程簡單，且無須過度金屬參與反應，所使用之溶劑得以回收，符合綠色化學之概念。

關鍵字

光反應 ； 硝基芳烴 ； 芳香胺

並列摘要

In this thesis, primary aromatic amines were synthesized from the corresponding nitroarenes via photoreaction. The reaction was found to be more efficient when irradiated with a broad band of 306 nm UV light; and the acidity of aluminium oxide was found to be important. When reactions are completed, products could be isolated by acid-base extraction, or by column chromatography. We also tried to synthesize primary aromatic amines from the corresponding nitroarenes without sensitizer in 2-propanol by photoreaction. The photoinduced reduction of primary nitroarenes using a continuous flow system to shorten reaction time and increase efficiency of the reaction were also investigated. Without the usage of transition metal and by recycling the solvent, this photochemical reduction of nitroarene fits the concept of green chemistry.

並列關鍵字

nitroarenes ； photoreaction ； aromatic amines

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