5-氯-2-戊酮与环丙基甲基酮物性及汽液相平衡

doi:10.7523/j.ucas.2023.005

中国科学院大学学报 ›› 2024, Vol. 41 ›› Issue (4): 461-467.DOI: 10.7523/j.ucas.2023.005

• 化学与生物学 • 上一篇

5-氯-2-戊酮与环丙基甲基酮物性及汽液相平衡

徐丽君^1,2, 李祥³, 李辉³, 刘龙², 张延强^2,3, 姜仁政¹

1. 沈阳化工大学化学工程学院, 沈阳 110142;
2. 中国科学院过程工程研究所中国科学院粉体材料技术重点实验室, 北京 100190;
3. 郑州中科新兴产业技术研究院, 郑州 450000

收稿日期:2022-09-23 修回日期:2023-02-04 发布日期:2023-03-15
通讯作者: 张延强,E-mail:yqzhang@ipe.ac.cn;姜仁政,E-mail:jiangrenzheng@syuct.edu.cn
基金资助:
国家自然科学基金(22178359,U21A20307)资助

Materialization properties and vapor-liquid phase equilibrium for 5-chloro-2-pentanone with cyclopropyl methyl ketone

XU Lijun^1,2, LI Xiang³, LI Hui³, LIU Long², ZHANG Yanqiang^2,3, JIANG Renzheng¹

1. School of Chemical Engineering, Shenyang University of Chemical Technology, Shenyang 110142, China;
2. CAS Key Laboratory of Science and Technology on Particle Materials, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China;
3. Zhengzhou Institute of Emerging Industrial Technology, Zhengzhou 450000, China

Received:2022-09-23 Revised:2023-02-04 Published:2023-03-15

摘要/Abstract

摘要： 测定5-氯-2戊酮和环丙基甲基酮的物化性质：密度、黏度、摩尔体积、热膨胀系数和表面张力。测定5-氯-2-戊酮(1)+环丙基甲基酮(2)二元体系的汽液相平衡 (VLE)，并应用Aspen Plus V11中Van Laar方程、Wilson方程和NRTL方程对实验数据进行关联，回归得到二元交互参数。实验结果通过热力学一致性检查。该研究不仅补充了汽液相平衡数据库，也为5-氯-2-戊酮与环丙基甲基酮的分离提供热力学数据。

关键词: 5-氯-2-戊酮, 环丙基甲基酮, 物性, 汽液相平衡, Aspen模拟

Abstract: The physical and chemical properties for 5-chloro-2-pentanone and cyclopropyl methyl ketone, including density, viscosity, molar volume, thermal expansion coefficient, and surface tension, were determined. The vapor-liquid phase equilibrium (VLE) of the binary system of 5-chloro-2-pentanone (1) + cyclopropyl methyl ketone (2) was further determined, and Van Laar equation, Wilson equation, and NRTL equation in Aspen Plus V11 were applied to correlate the experimental data. Moreover, the binary interaction parameters were also obtained by regression. The experimental results were confirmed by a thermodynamic consistency examination. This study not only complements the vapor-liquid phase balance database, but also provides thermodynamic data for the isolation of 5-chloro-2-pentanone and cyclopropyl methyl ketone.

Key words: 5-chloro-2-pentanone, cyclopropyl methyl ketone, materialization properties, vapor-liquid phase equilibrium, Aspen simulation

中图分类号:

O623.54+2

徐丽君, 李祥, 李辉, 刘龙, 张延强, 姜仁政. 5-氯-2-戊酮与环丙基甲基酮物性及汽液相平衡[J]. 中国科学院大学学报, 2024, 41(4): 461-467.

XU Lijun, LI Xiang, LI Hui, LIU Long, ZHANG Yanqiang, JIANG Renzheng. Materialization properties and vapor-liquid phase equilibrium for 5-chloro-2-pentanone with cyclopropyl methyl ketone[J]. Journal of University of Chinese Academy of Sciences, 2024, 41(4): 461-467.

参考文献

[1] Umesha B, Basavaraju Y B. Synthesis and pharmacological studies of new pyrazole analogues of podophyllotoxin[J]. Russian Journal of Bioorganic Chemistry, 2014, 40(4): 467-476. DOI: 10.1134/S106816201404013X.
[2] Khan G M, Hussain A, Hanif R M. Preparation and evaluation of 5, 9-dimethyl-2-cyclopropyl-2-decanol as a penetration enhancer for drugs through rat skin[J]. Pakistan Journal of Pharmaceutical Sciences, 2011, 24(4): 451-457.
[3] Butcher K J, Denton S M, Field S E, et al. Convergent asymmetric synthesis of two complex TRPV1 antagonists[J]. Organic Process Research & Development, 2011, 15(5): 1192-1200. DOI: 10.1021/op200177b.
[4] Oniciu D C, Pop E, Dasseux J L H, et al. Long hydrocarbon chain diols and diacids with central ether or ketone moieties that favorably alter lipid disorders[J]. Pharmazie, 2006, 61(2): 157-165.
[5] Hara R, Furukawa T, Kashima H, et al. Enantioselective total synthesis of (+)-taxusin[J]. Journal of the American Chemical Society, 1999, 121(13): 3072-3082. DOI:10.1021/ja984250f.
[6] Burmudžija A Z, Muškinja J M, Kosani Aｃ＇1 M M, et al. Cytotoxic and antimicrobial activity of dehydrozingerone based cyclopropyl derivatives[J]. Chemistry and Biodiversity, 2017, 14(8): e1700077. DOI: 10.1002/cbdv.201700077.
[7] Martel C R. Military jet fuels, 1944-1987[R]. Report number: AFWAL-TR-87-2062.Wright-Patterson Air Force Base, OH.
[8] Edwards T. Liquid fuels and propellants for aerospace propulsion:1903-2003[J]. Journal of Propulsion and Power, 2003, 19(6): 1089-1107. DOI: 10.2514/2.6946.
[9] 何笑荣, 邹定, 姜文清, 等. 降血脂新药匹伐他汀[J]. 中国新药杂志, 2005, 14(4): 483-487. DOI: 10.3321/j.issn: 1003-3734.2005.04.031.
[10] Mochizuki T, Aoki Y, Yoshikado T, et al. Physiologically-based pharmacokinetic model-based translation of OATP1B-mediated drug-drug interactions from coproporphyrin I to probe drugs[J]. Clinical and Translational Science, 2022, 15(6): 1519-1531. DOI: 10.1111/cts.13272.
[11] 杨季秋, 严晞, 廖志新, 等. 环丙基甲基酮和环丙烷羧酸的合成[J]. 化学世界, 1990, 31(8): 356-358. DOI: 10.19500/j.cnki.0367-6358.1990.08.008.
[12] 程捷，程维兹，胡小健，等. 环丙基甲基酮的制备方法:CN1994996[P].2007-07-11.
[13] Chen J J, Sun W X, Wang Y X, et al. Performant Au hydrogenation catalyst cooperated with Cu-doped Al₂O₃ for selective conversion of furfural to furfuryl alcohol at ambient pressure[J]. Green Energy & Environment, 2021, 6(4): 546-556. DOI: 10.1016/j.gee.2020.05.005.
[14] Dai J H. Synthesis of 2,5-diformylfuran from renewable carbohydrates and its applications: a review[J]. Green Energy & Environment, 2021, 6(1): 22-32. DOI: 10.1016/j.gee.2020.06.013.
[15] Xu Q, Hu X, Zhang L J, et al. Cross-polymerization between the model furans and phenolics in bio-oil with acid or alkaline catalysts[J]. Green Energy & Environment, 2021, 6(1): 138-149. DOI: 10.1016/j.gee.2020.03.009.
[16] Kuznetsov K I, Skorodumov S V, Granchenko P P. Measurements of the dynamic viscosity and density of KOH solutions at atmospheric pressure[J]. High Temperature, 2020, 58(6): 806-811. DOI: 10.1134/S0018151X20060127.
[17] Ramírez Verduzco L F. Density and viscosity of biodiesel as a function of temperature: Empirical models[J]. Renewable and Sustainable Energy Reviews, 2013, 19: 652-665. DOI: 10.1016/j.rser.2012.11.022.
[18] Li H, Wang H K, Chen X S, et al. Measurement and correlation of densities and viscosities of 11 α-hydroxy-16α, 17α-epoxyprogesterone in chloroform[J]. Russian Journal of Physical Chemistry A, 2012, 86(4): 580-583. DOI: 10.1134/s0036024412040127.
[19] Kuduva S S, Sarma J A R P, Katz A K, et al. Melting-points of the meta- and para-isomers of anisylpinacolone[J]. Journal of Physical Organic Chemistry, 2000, 13(11): 719-728. DOI: 10.1002/1099-1395(200011)13: 11<719: AID-POC308>3.0.CO;2-2.
[20] Andreas J M, Hauser E A, Tucker W B. Boundary tension by pendant DROPS¹[J].The Journal of Physical Chemistry, 1938, 42(8): 1001-1019. DOI: 10.1021/j100903a002.
[21] Fordham S. On the calculation of surface tension from measurements of pendant drops[J]. Proceedings of the Royal Society of London Series A Mathematical and Physical Sciences, 1948, 194(1036): 1-16. DOI: 10.1098/rspa.1948.0063.
[22] Yu L M Y, Lu J J, Chan Y W, et al. Constrained sessile drop as a new configuration to measure low surface tension in lung surfactant systems[J]. Journal of Applied Physiology (Bethesda, Md.: 1985), 2004, 97(2): 704-715. DOI: 10.1152/japplphysiol.00089.2003.
[23] Wang X D, Gao Y, Yang J B, et al. Density, viscosity, and vapor-liquid equilibrium data for the binary mixture at atmosphere pressure: cyclopropyl methyl ketone + 2-acetylbutyrolactone, cyclopropyl methyl ketone + 5-chloro-2-pentanone[J]. Journal of Chemical & Engineering Data, 2017, 62(11): 3642-3650. DOI: 10.1021/acs.jced.7b00344.
[24] Królikowska M, Gos N, Skonieczny M. Temperature and composition dependence of the thermodynamic properties of an aqueous solution of 1-ethyl-3-methylimidazolium formate and 1-ethyl-3-methylimidazolium acetate[J]. Journal of Chemical & Engineering Data, 2021, 66(8): 3300-3314. DOI: 10.1021/acs.jced.1c00349.
[25] Houng P, Murakami Y, Shimoyama Y. Flow patterns in microfluidic system of CO₂+1-propanol, ethanol, methanol, and hexane binary mixtures at high pressures[J]. Chemical Engineering Journal, 2020, 394: 124891. DOI: 10.1016/j.cej.2020.124891.
[26] Khalifa M, Housam B, Ahmed B. Modeling of the phase behavior of CO₂ in water, methanol, ethanol and acetone by different equations of state[J]. Fluid Phase Equilibria, 2018, 469: 9-25. DOI: 10.1016/j.fluid.2018.04.006.
[27] Królikowska M, Grzeszyk K, Skonieczny M, et al. New experimental data on thermodynamic properties of the aqueous solution of N,N-diethyl-N-methylammonium bromide and N,N-diethyl-N-methylammonium methanesulfonate[J]. Journal of Chemical & Engineering Data, 2021, 66(5): 2281-2294. DOI: 10.1021/acs.jced.1c00111.
[28] Jiang X M, Ward T L, van Swol F, et al. Numerical simulation of ethanol-water-NaCl droplet evaporation[J]. Industrial & Engineering Chemistry Research, 2010, 49(12): 5631-5643. DOI: 10.1021/ie902042z.
[29] Kariznovi M, Nourozieh H, Abedi J. Vapor-liquid phase equilibria and physical properties measurements for ternary systems (methane + decane + hexadecane)[J]. Journal of Chemical & Engineering Data, 2012, 57(9): 2535-2542. DOI: 10.1021/je300482b.
[30] 陈建芳. 改进的Rose釜用于测取糠醛-水稀溶液的汽液平衡数据[J]. 广州化工, 1998, 26(4): 43-45.
[31] Laar J J V. The vapor pressure of binary mixtures[J]. Zeitschrift für Physikalische Chemie, 1910, 72U(1): 723-751. DOI:10.1515/zpch-1910-7236.
[32] Wilson G M. Vapor-liquid equilibrium. XI. A new expression for the excess free energy of mixing[J]. Journal of the American Chemical Society, 1964, 86(2): 127-130. DOI: 10.1021/ja01056a002.
[33] Reid R C, Prausnitz J M, Poling B E. The properties of gases and liquids[M]. 4th ed. New York: McGraw-Hill, 1987.
[34] Voutsas E, Louli V, Boukouvalas C, et al. Thermodynamic property calculations with the universal mixing rule for EoS/GE models: results with the Peng-Robinson EoS and a UNIFAC model[J]. Fluid Phase Equilibria, 2006, 241(1/2): 216-228. DOI: 10.1016/j.fluid.2005.12.028.
[35] Wisniak J. The Herington test for thermodynamic consistency[J]. Industrial & Engineering Chemistry Research, 1994, 33(1): 177-180. DOI: 10.1021/ie00025a025.

5-氯-2-戊酮与环丙基甲基酮物性及汽液相平衡

Materialization properties and vapor-liquid phase equilibrium for 5-chloro-2-pentanone with cyclopropyl methyl ketone

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 1

编辑推荐

Metrics

本文评价

访问统计

联系我们