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Materials Engineering

Preparation and physicochemical properties of cyclopropyl methyl ketazine

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  • 1. Beijing Key Laboratory of Ionic Liquids Clean Process, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China 2. School of Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China 3. Key Laboratory of Science and Technology on Particle Materials, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China 4. Zhengzhou Institute of Emerging Industrial Technology, Zhengzhou, Henan 450000, China

Received date: 2020-03-19

  Revised date: 2020-04-05

  Online published: 2021-03-01

Supported by

Design and Synthesis of Hypergolic Ionic Liquids with Ring Strains and Application as High-Energetic Propellants

Abstract

Ketazines as useful intermediates have been extensively applied in many industrial fields, including dyes, pharmaceuticals, aviation fuels, photosensitive materials, as well as polymerizable monomers. In this work, a new ketazine derivative (cyclopropyl methyl ketazine, C10N2H16) was prepared from cyclopropyl methyl ketone and hydrazine hydrate. Under the atmospheric pressure, the reaction was studied under different mole ratios of cyclopropyl methyl ketone to hydrazine, reaction temperatures, and reaction times. With the optimized reaction conditions of 2.0:1, 363.2 K, 101.3 kPa and 7 h, the yield of cyclopropyl methyl ketazine was up to 93.6% through the chromatograph measurements. The structure of cyclopropyl methyl ketazine was characterized by IR and NMR spectra after it was purified through distillation. In order to prove the existence of isomers, Gaussian 09 program to optimize the structures was used and the energy values (single point energy) of cyclopropyl methyl ketazine was calculated. Furthermore, a comprehensive set of the physicochemical parameters for cyclopropyl methyl ketazine was provided, including density [ρ=0.884~0.947 g/cm3], dynamic viscosity (η=1.39~2.88 mPa?s), liquid heat capacity [Cp=2.03~2.32 J/(g?K)] and surface tension (σ=22.1~25.0 mN/m) in temperature range (280?400 K). The data of ρ, η and σ exhibited the negative correlations with temperature, while Vm, α and Cp showed the positive correlations with temperature, which all had a good fitting degree for equations. Considering the cyclopropyl methyl ketazine reaction systems, the vapor?liquid equilibria (VLE) of binary system (cyclopropyl methyl ketone?cyclopropyl methyl ketazine) was measured and correlated with NRTL model to acquire the binary interaction parameters. The obtained data and correlations are valuable for industrial processes, and could be the good references for industrial design.

Cite this article

Wenzhao ZHAO Peng ZHAO Long LIU Yangfeng XIA, Yanqiang ZHANG . Preparation and physicochemical properties of cyclopropyl methyl ketazine[J]. The Chinese Journal of Process Engineering, 2021 , 21(2) : 183 -192 . DOI: 10.12034/j.issn.1009-606X.220091

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