Investigation of the Effect of Alkyl Chain Length on Molecular Interactions Between Methyl Benzoate with Alcohols: A Stu
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Investigation of the Effect of Alkyl Chain Length on Molecular Interactions Between Methyl Benzoate with Alcohols: A Study of Physicochemical Properties Tingting Chen1 · Xiao Feng1 · Yuqiao Yin1 · Yingjie Xu1 Received: 12 November 2019 / Accepted: 18 February 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Densities, speeds of sound, and viscosities of binary mixtures of methyl benzoate (MB) with ethanol, 1-propanol, and 1-butanol were measured at temperature ranging from T = 293.2 to 313.2 K and refractive indices were determined at T = 303.2 K. Excess molar volumes, VE, isentropic compressibility deviations ∆κs and viscosity deviations, Δη, were obtained and fitted with the Redlich–Kister equation with satisfactory results. Based on the measured and derived physicochemical properties, the influence of the alkyl chain length of the alcohol on the molecular interactions of the studied mixtures was explored. The results show that both hydrogen bond interaction between carbonyl group of MB and hydroxyl group of alcohol and the packing efficiency, such as accommodation of alcohol in the interstice of MB, play an important role in the microstructure of the mixtures, which leads to the disruption of alcohol with the addition of MB. Moreover, by comparing VE, ∆κs and Δη values of MB (1) + alcohol (2) systems at T = 303.2 K, it is found that the strength of hydrogen bond interaction and the packing efficiency significantly weakens with increasing alkyl chain length of alcohol in going from ethanol to 1-butanol, resulting in the VE values of the studied systems gradually changing from a negative deviation to an S shape, the ∆κs and Δη values have negative deviations, and the ∆nD values have positive deviations. The obtained results will provide thermodynamic guidance for the industrial purification of methyl benzoate. Keywords Physicochemical property · Methyl benzoate · Microstructure · Hydrogen bond interaction
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1095 3-020-01029-4) contains supplementary material, which is available to authorized users. * Yingjie Xu [email protected] 1
Department of Chemistry, Shaoxing University, Shaoxing 312000, China
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Vol.:(0123456789)
Journal of Solution Chemistry
1 Introduction Methyl benzoate (MB) is a clear colorless liquid benzoate ester and has a pleasant floral smell and good solvent capability, resulting in many industrial applications as a perfumery, preservative and pesticide [1]. Furthermore, MB can be used as a raw material to prepare benzyl alcohol by iron-catalyzed [2] or Cu/ZnO/Al2O3-catalyzed hydrogenation [3]. For example, Jiang et al. reported a method for preparing benzyl alcohol from hydrogenation of MB by using Cu/ZnO/Al2O3 as a catalyst in methanol solution, and the results showed that when the MB was hydrogenated over this catalyst at 433.2 K and 7 MPa of H 2 for 10 h, the conversion of MB could reach 93.89% and the selectivity of benzyl alcohol is 88% [3]. Recentl
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