The synthesis of N -ethyl- n -butylamine by amines disproportionation
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The synthesis of N-ethyl-n-butylamine by amines disproportionation Lu-feng Xu • Jia-min Huang • Chao Qian • Xin-zhi Chen • Lie Feng • Yun-bin Chen • Chao-hong He
Received: 3 May 2012 / Accepted: 23 August 2012 / Published online: 7 September 2012 Ó Springer Science+Business Media B.V. 2012
Abstract A synthesis of N-ethyl-n-butylamine with simple separation method in a fixed-bed reactor using CuO–NiO–PtO/c-Al2O3 as the catalyst was proposed and investigated. The present catalytic system gave high activity and good selectivity, and the reaction conditions such as temperature and liquid hourly space velocity were optimized. Since no water was generated, the protocol proved to be easy to separate, and N-ethyl-n-butylamine was collected at 110 °C by distillation. The yield and the purity were 60.7 and 99.5 %, respectively. Keywords Catalyst
N-Ethyl-n-butylamine Disproportionation Fixed-bed reactor
Introduction N-Ethyl-n-butylamine is an important pesticide and pharmaceutical intermediate, which can be used for the synthesis of herbicides, such as pebulate and benfluralin L. Xu J. Huang C. Qian X. Chen C. He State Key Laboratory of Chemical Engineering, Zhejiang University, Hangzhou, People’s Republic of China L. Xu J. Huang C. Qian X. Chen (&) C. He Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, People’s Republic of China e-mail: [email protected] L. Xu College of Chemical and Materials Engineering, Quzhou College, Quzhou 324000, People’s Republic of China L. Feng Y. Chen Zhejiang Jianye Chemical Co., Ltd., Hangzhou 311600, People’s Republic of China
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[1], and the synthesis of nervous system drugs, such as milnacipran [2]. There are many methods for the synthesis of N-ethyl-n-butylamine, and the most commonly used method is N-alkylation of amine with aryl/alkyl halides [3, 4]. However, the use of aryl/alkyl halides is unfriendly to the environment, and this procedure generates large amounts of inorganic salts as byproducts [5]. The relatively green method for the synthesis of N-ethyl-n-butylamine is the catalytic amination of alcohols [6–8], generally by using the Cu, Ni, and Co catalysts. However, this method generates water as a byproduct, which will reduce the activity of the catalyst and may form azeotrope with the raw material alcohol and the product amine, thus rendering the purification of the target product difficult. The process for the amines disproportionation is a class of common side reactions in the synthesis of aliphatic amines. Some researchers have studied the amines disproportionation phenomenon in a number of systems, trying to suppress the disproportionation to improve the selectivity of primary products; however, the results showed that preventing the amines disproportionation reactions from the source was very difficult, and only possible by reducing the activity of the catalyst to reduce the amines disproportionation [7, 9, 10]. The research of the amines disproportionation reaction as the main reaction i
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