Screening ionic liquids solvent for separation of oil and hydroxybenzene mixtures based on COSMO-RS model

LIU Qian1 ZHANG Xianglan1 LI Wei2

(1.School of Chemical and Environmental Engineering, China University of Mining and Technology (Beijing) , Beijing, China 100083)
(2.School of Chemical Engineering, Beijing Institute of Petro-chemical Technology, Beijing, China 102600)

【Abstract】Phenolic compound separation of low temperature coal tar (LTCT) is important for its effective utilization. Based on the COSMO-RS model, with m-cresol and cumene as model compounds, ionic liquids were used as extractants for the separation of the oil and phenol system. A σ-profile database including 27 anions and 48 cations were established by Turbomole, screening the 1 296 ionic liquids by COSMOtherm. The influences of cations and anions on the separation of the m-cresol and cumene were investigated and some of them were verified by liquid-liquid equilibrium (LLE) data of ternary system, which indicated that the selection method of ionic liquid solvents was effective. The results show that the influences of the anions on the separation are more than those of the cations. Some ionic liquids are effective on separation, which contain Clor CH3COOin anions, because of the stronger hydrogen bond interaction between these ionic liquids and m-cresol. The increase of length of alkyl chain and the number of side chains can improve the separation effect of ionic liquid to m-cresol. The LLE data of ternary system of bmimOAc–m-cresol–cumene, bmimCl–m-cresol–cumene, emimOAc–m-cresol–cumene and TPAC–m-cresol–cumene by experiment show that the four kinds of ionic liquids have greater distribution coefficient and selectivity for m-cresol, and the order of extraction and separation effect was: emimOAc > bmimOAc > TPAC > bmimCl, which is consistent with the results obtained by COSMO-RS simulation screening, indicating that the screening has high accuracy.

【Keywords】 ionic liquids; phenolic compounds; COSMO-RS model; activity coefficient; separation; liquid-liquid equilibrium;

【DOI】

【Funds】 National Key Research and (2016YFB0600305)

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(Translated by REN XF)

    References

    [1] GE Y Z, JIN H. Recovery of phenols from coal tar and waste water by precipitation [J]. Journal of Chinese Coal Society, 1995, 20 (5): 545–550 (in Chinese).

    [2] ZHAO Y, MAO X F, ZHANG X J, et al. Preliminary exploration of extracting phenolic compounds in medium and low temperature coal tar by glycerin solution [J]. Clean Coal Technology, 2014, 20 (4): 55–57 (in Chinese).

    [3] JIA Y Z, JIA L. The hydroxybenzene using and pick-up in coal tar [J]. Contemporary Chemical Industry, 2008, 37 (2): 194–196 (in Chinese).

    [4] SHI Q. Identification and separation of phenolic compounds from diesel fuel in residual oil fluid catalytic cracking process [J]. Journal of China University of Petroleum (Edition of Nature Science), 2000, 24 (6): 18–20 (in Chinese).

    [5] HARA T, JONES L, LI N C, et al. Ageing of SRC liquids [J]. Fuel, 1981, 60 (12): 1143–1148.

    [6] GAO Z N, LIU L L, ZHU X M, et al. The composition analysis of coal derived light oil [J]. International Journal of Coal Science & Technology, 2008, 14 (1): 136–139.

    [7] YU P, YAO L, LUO Y B. Degradation treatment of highly concentrated phenol-containing industrial waste water [J]. Industrial Water Treatment, 2002, 22 (9): 5–8 (in Chinese).

    [8] MATSUMURA A, SATO S, KODERA Y, et al. Methanol-mediated extraction for coal liquid (2): The effect of phase separation caused by methanol on naphtha fraction derived from Wyoming coal [J]. Fuel Processing Technology, 2000, 68 (1): 13–21.

    [9] SATO S, MATSUMURA A, SAITO I, et al. Methanol-mediated extraction of coal liquid (5): Conceptual design and mass balance of a continuous methanol-mediated extraction process [J]. Energy & Fuels, 2002, 16 (6): 1337–1342.

    [10] MCCLENNEN W H, MEUZELAAR H L C, METCALF G S, et al. Characterization of phenols and indanols in coal-derived liquids: use of Curie-point vaporization gas chromatography/mass spectrometry [J]. Fuel, 1983, 62 (12): 1422–1429.

    [11] YI L, LI W Y, FENG J, et al. Recent progress on coal-based liquid oil separation technology [J]. CIESC Journal, 2017, 68 (10): 3678–3692 (in Chinese).

    [12] JIANG G C, ZHANG S J, WANG Y G, et al. Selective separation of aromatic components in low temperature coal tar [J]. CIESC Journal, 2015, 66 (6): 2131–2138 (in Chinese).

    [13] SATO S, MATSUMURA A. Extraction of phenol in water phase using liquefiel dimethyl ether [J]. Journal of the Japan Petroleum Institute, 2003, 46 (6): 375–378.

    [14] LI J, HE W J, QI Z W, et al. Screening ionic liquids for separation of methanol and dimethyl-carbonate mixtures based on COSMO-RS method [J]. Petrochemical Technology, 2016, 45 (12): 1499–1505 (in Chinese).

    [15] LEI Z G, XI X M, DAI C N, et al. Extractive distillation with the mixture of ionic liquid and solid inorganic salt as entrainers [J]. AIChE Journal, 2014, 60 (8): 2994–3004.

    [16] HOU Y C, PENG W, YANG C M, et al. Extraction of phenolic compounds from simulated oil with imidazolium based ionic liquids [J]. CIESC Journal, 2013, 64 (S1): 118–123 (in Chinese).

    [17] LIN Z Q, HOU Y C, REN S H, et al. Phase equilibria of phenol + toluene + quaternary ammonium salts for the separation of phenols from oil with forming deep eutectic solvents [J]. Fluid Phase Equilibria, 2016, 429: 67–75.

    [18] WANG Z, HOU Y C, REN S H, et al. Oil entrainment during separating phenols from model oils via forming deep eutectic solvents [J]. CIESC Journal, 2015, 66 (S1): 247–252 (in Chinese).

    [19] YANG X Q, HE C C, CHEN K X, et al. Screening of ionic liquids for separation of acetonitrile and water azeotropic mixtures based on COSMO-RS method [J]. Chemical Industry and Engineering Progress, 2011, 30 (S2): 55–61 (in Chinese).

    [20] CAI F F, WU X Y, Chen C, et al. Isobaric vapor–liquid equilibrium for methanol + dimethyl carbonate + phosphoric-based ionic liquids [J]. Fluid Phase Equilibria, 2013, 352: 47–53.

    [21] GUTIERREZ J P, MEINDERSMA G W, HAAN A B D. COSMO-RS-based ionic-liquid selection for extractive distillation processes [J]. Industrial & Engineering Chemistry Research, 2012, 51 (35): 11518–11529.

    [22] KLAMT A. Conductor-like screening model for real solvents: a new approach to the quantitative calculation of solvation phenomena [J]. Journal of Physical Chemistry, 1995, 99 (7): 2224–2235.

    [23] KLAMT A, JONAS V, BURGER T, et al. Refinement and parametrization of COSMO-RS [J]. Journal of Physical Chemistry A, 1998, 102 (26): 5074–5085.

    [24] KLAMT A, ECKERT F. COSMO-RS: a novel and efficient method for the a priori prediction of thermophysical data of liquids [J]. Fluid Phase Equilibria, 2000, 172 (1): 43–72.

    [25] ECKERT F, KLAMT A. Fast solvent screening via quantum chemistry: COSMO–RS approach [J]. AIChE Journal, 2002, 48 (2): 369–385.

    [26] LI R, CUI X B, WU T, et al. Selection of ionic liquid solvent for liquid–liquid extraction based on COSMO–SAC model [J]. CIESC Journal, 2013, 64 (2): 452–469 (in Chinese).

    [27] CORDERI S, CALVAR N, GOMEZ E, et al. Quaternary (liquid + liquid) equilibrium data for the extraction of toluene from alkanes using the ionic liquid [Emim][MSO4] [J]. Journal of Chemical Thermodynamics, 2014, 76 (1): 79–86.

    [28] SCHAFER A, KLAMT A, SATTEL D, et al. COSMO Implementation in TURBOMOLE: extension of an efficient quantum chemical code towards liquid systems [J]. Physical Chemistry Chemical Physics, 2000, 2 (10): 2187–2193.

    [29] ANDZELM J, KOLMEL C, KLAMT A. Incorporation of solvent effects into density functional calculations of molecular energies and geometries [J]. Journal of Chemical Physics, 1995, 103 (21):9 312–9320.

    [30] KLAMT A, ECKERT F, DIEDENHOFEN M. Prediction or partition coefficients and activity coefficients of two branched compounds using COSMOtherm [J]. Fluid Phase Equilibria, 2009, 285 (1): 15–18.

    [31] PRETEL E J, LOPEZ P A, BOTTINI S B, et al. Computer-aided molecular design of solvents for separation processes [J]. Chemical Engineering & Technology, 2010, 29 (1): 33–43.

    [32] BANERJEE T, SINGH M K, KHANNA A. Prediction of binary VLE for imidazolium based ionic liquid systems using COSMO-RS [J]. Industrial & Engineering Chemistry Research, 2006, 45 (9): 3207–3219.

    [33] HOU Y C, REN Y H, PENG W, et al. Separation of phenols from oil using imidazolium-based ionic liquids [J]. Industrial & Engineering Chemistry Research, 2013, 52 (50): 18071–18075.

    [34] PENG W. Extraction of phenolic compounds from oils using ionic liquids [D]. Beijing: Beijing University of Chemical Technology, 2012 (in Chinese).

This Article

ISSN:0438-1157

CN: 11-1946/TQ

Vol 69, No. 12, Pages 5100-5111

December 2018

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Article Outline

Abstract

  • Introduction
  • 1 Screening of ionic liquids
  • 2 Experimental materials and methods
  • 3 Results and discussion
  • 4 Conclusions
  • Symbol description
  • Appendix 1
  • Appendix 2
  • References