Catalytic Amination of Octanol for Synthesis of Trioctylamine and Catalyst Characterization
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Catalytic Amination of Octanol for Synthesis of Trioctylamine and Catalyst Characterization Yunling Li • Qiuxiao Li • Lifei Zhi Minghui Zhang
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Received: 26 July 2011 / Accepted: 12 August 2011 / Published online: 23 August 2011 Ó Springer Science+Business Media, LLC 2011
Abstract Synthesis of trioctylamine by the amination of octanol and ammonia under atmospheric pressure over an excellent Ni–Cu catalyst supported on diatomite is studied in this article. The key factor for the synthesis is the preparation of catalyst with a high activity and selectivity. The activity and selectivity can be adjusted by varying the Ni to Cu ratios. The optimum molar ratio of Ni to Cu was 1.25:1. For the catalyst with a Ni/Cu ratio of 1.25:1, the conversion of octanol and the selectivity of trioctylamine reached 100 and 97.3%, respectively, at 5 h. The reaction of dioctylamine with octanol was the rate-determining step for the formation of trioctylamine. The Physical properties of catalysts, such as particle size, Brunauer–Emmett–Teller (BET) surface area, valence state of catalyst elements, morphology and reduction properties of catalysts were investigated by using X-ray diffraction, nitrogen adsorption–desorption isotherms (BET), X-ray photoelectron spectroscopy, Transmission electron microscopy, and temperature programmed reduction, respectively. The reaction scheme of catalytic amination of octanol with ammonia was discussed. Keywords Ni/Cu Catalytic amination Octanol Trioctylamine Characterization
Y. Li (&) College of Chemistry and Chemical Engineering, Shanxi University, 34# Wenyuan Str., Taiyuan 030001, Shanxi, People’s Republic of China e-mail: [email protected] Y. Li Q. Li L. Zhi M. Zhang China Research Institute of Daily Chemical Industry, Taiyuan, China
1 Introduction Long-chain alkyl tertiary amines including mono-, di-, and tri-alkyl tertiary amines (RNMe2, R2NMe and R3N, respectively), as important intermediates for cationic surfactants, amphoteric compounds and important organic intermediates, have extensive applications. These derivatives of tertiary amines can be used as detergents, fabric softener, antistatic agents, bactericides, cosmetic additives and so forth. Especially, tri-alkyl tertiary amines can be used as extraction agents to recover various metal ions and acids from water solutions and as phase transfer catalysts accelerating the reaction rates of some reactions [1–3]. Catalytic amination of fatty alcohols is a major process for the preparation of these amines at present. Studies on catalysts and synthetic processes for mono- and di-alkyl tertiary amines have been performed for a long time, and have been reported widely [1, 3–7]. Cu/Ni-based catalysts show excellent performances for the preparation of monoand di-alkyl tertiary amines [8–13]. Performances of Cu– Ni catalysts can be adjusted by varying Cu/Ni ratios or by adding a third element. Reported catalysts so far for the preparation of mono- and di-alkyl tertiary amines contain more Cu than Ni [3–13]. In Cu-rich-Cu/Ni-based catalyst
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