Solid—liquid equilibrium and yield correlation model of melt crystallization of dimethylphenol isomer mixtures

Zhang Yuxi; Yang Li; Ma Yixin; Zhang Yan; Cao Junya; Cheng Jingcai; Yang Chao

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Solid—liquid equilibrium and yield correlation model of melt crystallization of dimethylphenol isomer mixtures

Updated：2026-03-13

- Solid—liquid equilibrium and yield correlation model of melt crystallization of dimethylphenol isomer mixtures
- Solid—liquid equilibrium and yield correlation model of melt crystallization of dimethylphenol isomer mixtures
- 中国化学工程学报（英文） 2026年89卷第1期页码：112-122
- Affiliations：
  
  School of Chemical and Environmental Engineering, China University of Mining and Technology, Beijing 100083, China
  State Key Laboratory of Petroleum Molecular & Process Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China
  School of Chemical Engineering, University of Chinese Academy of Sciences, Beijing 100049, China
- Author bio：
  
  Corresponding authors. E-mail addresses: yangli@ipe.ac.cn(L. Yang)
  jccheng@ipe.ac.cn(J. Cheng).
- Funds：
  
  the National Natural Science Foundation of China(22308358;22208346;22421003);IPE Project for Frontier Basic Research(QYJC-2023-05);CAS Project for Young Scientists in Basic Research.(YSBR-038)
- DOI：
  中图分类号：
- 收稿：2025-05-23，
  
  修回：2025-08-20，
  
  录用：2025-08-21，
  
  网络首发：2025-09-12，
  
  纸质出版：2026-01
- Accepted：
Scan QR Code
Zhang Yuxi, Yang Li, Ma Yixin, 等. Solid—liquid equilibrium and yield correlation model of melt crystallization of dimethylphenol isomer mixtures[J]. 中国化学工程学报（英文）, 2026,89(1):112-122.

Zhang Yuxi, Yang Li, Ma Yixin, et al. Solid—liquid equilibrium and yield correlation model of melt crystallization of dimethylphenol isomer mixtures[J]. Chinese Journal of Chemical Engineering, 2026, 89(1): 112-122.
Zhang Yuxi, Yang Li, Ma Yixin, 等. Solid—liquid equilibrium and yield correlation model of melt crystallization of dimethylphenol isomer mixtures[J]. 中国化学工程学报（英文）, 2026,89(1):112-122. DOI：

Zhang Yuxi, Yang Li, Ma Yixin, et al. Solid—liquid equilibrium and yield correlation model of melt crystallization of dimethylphenol isomer mixtures[J]. Chinese Journal of Chemical Engineering, 2026, 89(1): 112-122. DOI：

摘要

Abstract

Dimethylphenols serve as important intermediates in synthesizing pharmaceuticals and agrochemicals

yet traditional distillation struggles to separate their isomers due to minimal boiling point differences

and the development of melt crystallization is hampered by lacking solid—liquid equilibrium (SLE) data for some isomers. Therefore

the SLE data of both binary and ternary mixtures of 2

3-dimethylphenol (2

3-DMP)

5-dimethylphenol (3

5-DMP)

and 3

4-dimethylphenol (3

4-DMP) were determined by using differential scanning calorimetry in this work. Additionally

crystallographic analysis was conducted to investigate the thermodynamic characteristics of these mixtures. The experimental results indicated that all the systems investigated in this research exhibited eutectic behavior. The experimentally obtained SLE data were well correlated with the Wilson and non-random two-liquid models. The excess thermodynamic functions were calculated to analyze the types and intensities of the molecular interactions occurring in the mixtures. Furthermore

this study developed a model for the correlation between the theoretical crystallization yield and the actual cooling yield and final yield in melt crystallization. This study has furnished reliable data essential for developing and optimizing the melt crystallization process of mixtures of 2

3-DMP

5-DMP

and 3

4-DMP.

关键词

Keywords

references

O.A. Kholdeeva, N.N. Trukhan, M.P. Vanina, V.N. Romannikov, V.N. Parmon, J. Mrowiec-Białon', A.B. Jarze˛bski, A new environmentally friendly method for the production of 2, 3, 5-trimethyl- p -benzoquinone, Catal. Today 75 (1—4) (2002)203—209.

B.D. Raju, K.S. R. Rao, G.S. Salvapathi, P.S. S.Prasad, P. K. Rao, Aromatization of isophorone to 3, 5-xylenol over Cr 2 O 3 /SiO 2 catalysts, Appl. Catal. Gen. 193 (1—2) (2000) 123—128.

Quadintel, Global 3, 4-Xylenol (3, 4-Dimethylphenol, CAS 95-65-8) Market, 2020-2026, Quadintel, 2022. https://www.quadintel.com/toc/global-34-xylenol-34-dimethylphenol-cas-95-65-8-market/QI043.

APO Research, Global 3, 5-Dimethylphenol (meta-xylenol) Market Analysis and Forecast 2025-2031, APO Research, 2025. https://www.aporesearch. com/reports/chemical-material/global-35-dimethylphenol-meta-xylenolmarket-analysis-and-forecast-2025-2031.

C.P. Yan, X.T. Duan, W. Yan, G.H. Shang, Refinement of 2, 3, 5-trimethylphenol by fractional crystallization, Technol. Dev. Chem. Ind. 39 (2)(2010)12—14.

M.D. Qu, Z.M. E, Xylenol withdrawing in coal tar, Chem. Technol. Econ. (10) (2005) 34 — 35 + 39.

Y. Shi, G.Y. Yu, X.Q. Wang, Experimental determination and thermodynamic modeling of solid—liquid equilibrium of 2, 6-dimethylphenol, 3, 5-dimethylphenol and 2, 5-dimethylphenol binary and ternary systems, Thermochim. Acta 710 (2022) 179174.

R.J.L. Andon, D.P. Biddiscombe, J.D. Cox, R. Handley, D. Harrop, E.F.G. Herington, J.F. Martin, Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols, J. Chem. Soc. (1960) 5246, 1009.

X.H. Wu, Preparation method and application progress of 3, 5-xylenol, Zhejiang Chem. Ind. 54 (10) (2023) 27—32.

Y.B. Qi, J. Li, Process parameters influence on zone refining and thermodynamics analysis of 1, 2-diphenylethane, Chin. J. Chem. Eng. 42 (2022) 338—343.

B.Y. Zhang, L. Yang, H.L. Wang, C.L. Shen, Y.Y. Li, J.C. Cheng, C. Yang, Experiment and modeling of static layer melt crystallization in a crystallizer with an inner cooling tube, J. Cryst. Growth 593 (2022) 126739.

M. Nakahara, K. Nomura, T. Washiya, T. Chikazawa, I. Hirasawa, Removal of liquid and solid impurities from uranyl nitrate hexahydrate crystalline particles in crystal purification process, J. Nucl. Sci. Technol. 48 (3) (2011) 322—329.

M. Nakahara, K. Nomura, T. Koizumi, Purification rate of uranyl nitrate hexahydrate crystal for transuranium elements on isothermal sweating phenomenon, Ind. Eng. Chem. Res. 49(22)(2010)11661—11666.

A. König, M. Stepanski, A. Kuszlik, P. Keil, C. Weller, Ultra-purification of ionic liquids by melt crystallization, Chem. Eng. Res. Des. 86(7)(2008)775—780.

C.S. Luo, W.W. Chen, W.F. Han, Experimental study on factors affecting the quality of ice crystal during the freezing concentration for the brackish water, Desalination 260 (1—3) (2010) 231—238.

J. Jung, H. Lee, K.J. Kim, Purification of acetic acid wastewater using layer melt crystallization, Separ. Sci. Technol. 43(5)(2008)1021—1033.

Z.S. Fu, S.Z. Jia, Z.G. Gao, J.K. Wang, J.B. Gong, Model-based optimization of layer melt crystallization for isomers green separation, Sep. Purif. Technol. 378 (2025)134657.

W. Chen, S.Q. Li, S.F. Li, Purification of 2-pyrrolidone by falling film melt crystallization, Ind. Eng. Chem. Res. 60 (36)(2021)13286—13292.

C.X. Huang, Y. Fang, J. Wang, Y.J. Gao, C.H. Ju, Y .X. Leng, Measurement and modelling of ternary solid—liquid phase equilibrium of (DL-malic acid +maleic acid + water) from 283.15 K to 333.15 K, J. Chem. Thermodyn. 159 (2021)106470.

S.M. Mirpoorian, M. Vakili, S.H. Noie Baghban, P. Roohi, Determination and measurement of solid—liquid equilibrium for binary fatty acid mixtures based on NRTL and UNIQUAC activity models, J. Therm. Anal. Calorim. 137(2) (2019)679—688.

H. Feng, J. Qian, Y.F. Wu, X. Xu, Y.F. Feng, J.Y. Li, N. Wang, X. Huang, T. Wang, C. Xie, H.X. Hao, Thermodynamics and kinetics of the melt crystallization of fluoroethylene carbonate, Ind. Eng. Chem. Res. 64 (21) (2025) 10578—10587.

Q. Zhao, Y.H. Pan, Y.K. Xiong, P. Xu, Q.Y. Sun, H.M. Yin, F.M. Xue, Solubility, thermodynamic parameters, and dissolution properties of 17-α hydroxyprogesterone in 13 pure solvents, ACS Omega 9 (14) (2024) 16106—16117.

A. Li, N. Wang, X.T. Ji, Y.H. Huang, J.W. Zhao, J. Feng, B.H. Hou, T. Wang, X. Huang, H.X. Hao, Solid—liquid equilibrium of GLA—NaCl system and its application for separating GLA and NaCl, Ind. Eng. Chem. Res. 63 (10)(2024) 4585—4594.

A.K. Lavrinenko, I.Y. Chernyshov, E.A. Pidko, Machine learning approach for the prediction of eutectic temperatures for metal-free deep eutectic solvents, ACS Sustain. Chem. Eng. 11(42)(2023)15492—15502.

D.W. Wei, S.N. Han, X. Shen, Solid—liquid phase equilibria of ( n -octadecane with myristic, and palmitic acid) binary mixtures used as phase change materials(PCMs), J. Chem. Thermodyn. 101(2016)7—11.

G. Poeti, E. Fanelli, M. Braghetti, A differential scanning calorimetric study of some phenol derivatives, J. Therm. Anal. 24 (2)(1982)273—279.

S.V.R. Mastrangelo, Adiabatic calorimeter for determination of cryoscopic data, Anal. Chem. 29(5)(1957) 841—845.

A. Codoner, I. Monzo, F. Tomas, R. Valero, Apparent dipole moments and molar volumes of dimethylphenols in some nonpolar solvents, J. Phys. Chem. 90(10) (1986)2244—2247.

F.L. Ma, S.J. Xu, F. Wang, Y.Q. Bu, Y.F. Wang, L. Zhu, Measurement and correlation of 2, 3-2, 5-2, 6-dimethylphenol solid-liquid phase equilibrium at atmospheric pressure, Chem. Eng. 49 (5) (2021) 48—52+68.

D. Trache, K. Khimeche, R. Benelmir, A. Dahmani, DSC measurement and prediction of phase diagrams for binary mixtures of energetic materials' stabilizers, Thermochim. Acta 565(2013)8—16.

U. Doman'ska, J. Łachwa, Thermodynamics of binary mixtures of N -methyl-2-pyrrolidinone and ketone. Experimental results and modelling of the(solid+liquid) equilibrium and the (vapour + liquid) equilibrium. The modified UNIFAC (Do) model characterization, J. Chem. Thermodyn. 37 (7) (2005) 692—704.

S. Chelouche, D. Trache, S.P. Pinho, K. Khimeche, Experimental and modeling studies of binary organic eutectic systems to be used as stabilizers for nitrate esters-based energetic materials, Fluid Phase Equilib. 498(2019)104—115.

R.S.B. Reddi, V.S.A.K. Satuluri, U.S. Rai, R.N. Rai, Thermal, physicochemical and microstructural studies of binary organic eutectic systems, J. Therm. Anal. Calorim. 107(1)(2012)377—385.

A. Su, S.F. Li, Measurement and correlation of solid—liquid phase equilibria for binary and ternary systems consisting of N -vinylpyrrolidone, 2-pyrrolidone and water, Chin. J. Chem. Eng. 26(4)(2018)806—811.

T.T. Shen, H. Peng, X. Ling, Experimental measurements and thermodynamic modeling of melting temperature of the binary systems n -C 11 H 24 — n -C 14 H 30 , n -C 12 H 26 — n -C 13 H 28 , n -C 12 H 26 — n -C 14 H 30 , and n -C 13 H 28 — n -C 15 H 32 for cryogenic thermal energy storage, Ind. Eng. Chem. Res. 58 (32) (2019) 15026—15035.

D. Trache, K. Khimeche, Study on the influence of ageing on thermal decomposition of double-base propellants and prediction of their in-use time, Fire Mater. 37(4)(2013)328—336.

J.A. Nelder, R. Mead, A simplex method for function minimization, Comput. J. 7(4) (1965)308—313.

Y.C. Shen, S.H. Zong, L.P. Dang, H.Y. Wei, Solubility and thermodynamics of probenecid-4, 4'-azopyridine cocrystal in pure and binary solvents, J. Mol. Liq. 290(2019)111195.

W.E. Acree, Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochim. Acta 189(1) (1991)37—56.

N. Singh, N.B. Singh, U.S. Rai, O.P. Singh, Structure of eutectic melts; binary organic systems, Thermochim. Acta 95(1) (1985)291—293.

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