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Preparation of para-Aminophenol from Nitrobenzene through Bamberger Rearrangement Using a Mixture of Heterogeneous and Homogeneous Acid Catalysts
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-02-09 00:00:00 , DOI: 10.1021/acs.oprd.7b00354 Roxan Joncour 1 , Amadéo Ferreira 2 , Nicolas Duguet 1 , Marc Lemaire 1
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2018-02-09 00:00:00 , DOI: 10.1021/acs.oprd.7b00354 Roxan Joncour 1 , Amadéo Ferreira 2 , Nicolas Duguet 1 , Marc Lemaire 1
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The direct preparation of para-aminophenol (PAP) from nitrobenzene (NB) through Bamberger rearrangement was studied in a biphasic medium using a mixture of NbOx/SiO2 and H2SO4 as an acid catalyst. After optimization of the reaction parameters, PAP was obtained with 85–88% selectivity that represents a 10% selectivity improvement compared to sulfuric acid alone. The optimized conditions were implemented in a scale-up reaction, and PAP was isolated in 84% yield (based on the recovered starting material) with 97% HPLC purity. Overall, this process requires less sulfuric acid than the traditional process, leading to a drastic reduction of the saline waste.
中文翻译：
均相和均相酸催化剂通过班伯格重排法从硝基苯制备对氨基苯酚
使用NbO x / SiO 2和H 2 SO 4的混合物作为酸催化剂，在双相介质中研究了通过班伯格重排从硝基苯（NB）直接制备对氨基苯酚（PAP）的方法。优化反应参数后，获得的PAP具有85-88％的选择性，与单独的硫酸相比，选择性提高了10％。在放大反应中实现了最佳条件，并以84％的收率（基于回收的起始原料）分离出PAP，HPLC纯度为97％。总体而言，与传统工艺相比，该工艺所需的硫酸更少，从而大大减少了盐水浪费。
更新日期：2018-02-09
中文翻译：
均相和均相酸催化剂通过班伯格重排法从硝基苯制备对氨基苯酚
使用NbO x / SiO 2和H 2 SO 4的混合物作为酸催化剂，在双相介质中研究了通过班伯格重排从硝基苯（NB）直接制备对氨基苯酚（PAP）的方法。优化反应参数后，获得的PAP具有85-88％的选择性，与单独的硫酸相比，选择性提高了10％。在放大反应中实现了最佳条件，并以84％的收率（基于回收的起始原料）分离出PAP，HPLC纯度为97％。总体而言，与传统工艺相比，该工艺所需的硫酸更少，从而大大减少了盐水浪费。
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