Purification of 2,6-dimethylnaphthalene containing in light cycle oil by distillation-solvent extraction-solute crystallization combination

Su Jin Kim

Journal of Industrial and Engineering Chemistry, Vol.79, 146-153, November, 2019

DOI10.1016/j.jiec.2019.06.018 Export Citation

Purification of 2,6-dimethylnaphthalene containing in light cycle oil by distillation-solvent extraction-solute crystallization combination

Su Jin Kim^†

Department of Chemical Engineering, Chungwoon University, Incheon 22100, Republic of Korea

E-mail:

Purification of about 1% 2,6-dimethylnaphthalene (2,6-DMN) present in light cycle oil (LCO) was investigated by the combination of distillation to concentrate 10 types of DMN isomers (DMNs) from LCO, solvent extraction to separate between DMNs and paraffin compounds from DMNs-enriched distillate, and solute crystallization (SC) to purity 2,6-DMN from DMNs-enriched extract. Aqueous solution of dimethylformamide (DMF) and mixture of methanol and acetone were used solvent of extraction and SC, respectively. Through the combination of distillation-DMF extraction-SC, the crystal containing 99.6% 2,6-DMN was recovered. I confirmed that the combination examined by this work was one of the very useful combination for the purification of 2,6-DMN present in the LCO.

Keywords:Light cycle oil;2,6-Dimethylnaphthalene;Distillation-DMF extraction-solute;crystallization combination;Purification;Bicyclic aromatic compound

[References]

Kim SJ, Kim SC, Sep. Sci. Technol., 38, 4097 (2003)
Kim SJ, Egashira R, Kawasaki J, J. Japan Pet. Inst., 38, 114 (1995)
Kim SJ, Kim SC, Kawasaki J, Sep. Sci. Technol., 38(1), 179 (2003)
Kim SJ, Kim SC, Sep. Sci. Technol., 39(5), 1093 (2004)
Alsahhaf TA, Kapetanovic E, Fluid Phase Equilib., 118(2), 271 (1996)
Vakili-Nezhaad GR, Modarress H, Mansoori GA, Sep. Sci. Technol., 35(5), 743 (2000)
Radwan GM, Almuhtaseb SA, Fahim MA, Fluid Phase Equilib., 129(1-2), 175 (1997)
Jiao TT, Zhuang XL, He HY, Li CS, Chen HN, Zhang SJ, Ind. Eng. Chem. Res., 54(9), 2573 (2015)
Jiao TT, Li CS, Zhuang XL, Cao SS, Chen HN, Zhang SJ, Chem. Eng. J., 266, 148 (2015)
Kang HC, Kim SJ, Polycyclic Aromatic Compd., 36, 745 (2016)
Kim SJ, Chun YJ, Sep. Sci. Technol., 40(10), 2095 (2005)
Kim SJ, Polycyclic Aromatic Compd., 39, 60 (2019)
Egashira R, Kawasaki J, J. Japan Pet. Inst., 40, 107 (1997)
Kim SJ, Kang HC, Kim YS, Jeong HJ, Bull. Korean Chem. Soc., 31, 1143 (2010)
Sharma A, Goswami AN, Rawat BS, Krishina R, J. Membr. Sci., 32, 19 (1987)
Motoyuki M, Yamamoto K, Yoshida S, Yamamoto S, Sapre AV, McWilliams JP, Donnelly SP, Hellring SD, US Patent 6,018,087 (2000).
Yamamoto Y, Sato Y, Ebina T, Yokoyama C, Takahasi S, Mito Y, Tanabe H, Nishiguchi N, Nagaoka K, Fuel, 70, 565 (1991)
Motoyuki M, Yamamoto K, Sapre AV, McWilliams JP, Donnelly SP, US Patent 6,018,086 (2000).
Uchida H, Iwai Y, Amiya M, Arai Y, Ind. Eng. Chem. Res., 36(2), 424 (1997)
Xiong WP, Zeng GM, Yang ZH, Zhou YY, Zhang C, Cheng M, Liu Y, Hu LA, Wan J, Zhou CY, Xu R, Li X, Chemosphere, 210, 1061 (2018)
Ahmed MJ, Environ. Toxicol. Pharmacol., 50, 1 (2017)
Xiong WP, Tong J, Yang ZH, Zeng GM, Zhou YY, Wang DB, Song PP, Xu R, Zhang C, Cheng M, J. Colloid Interface Sci., 493, 17 (2017)
Mochida I, Fei YQ, Sakanishi K, Chem. Lett., 515 (1990).
Hall S, Tang R, Baeyens J, Dewil R, Polycyclic Aromatic Compd., 29, 160 (2009)
Motoyuki M, Yamamoto K, Sapre AV, McWilliams JP, US Patent 6,011,190 (2000).
McAuliffe C, Nature (December),1092 (1963).

[1] Kim SJ, Kim SC, Sep. Sci. Technol., 38, 4097 (2003)

[2] Kim SJ, Egashira R, Kawasaki J, J. Japan Pet. Inst., 38, 114 (1995)

[3] Kim SJ, Kim SC, Kawasaki J, Sep. Sci. Technol., 38(1), 179 (2003)

[4] Kim SJ, Kim SC, Sep. Sci. Technol., 39(5), 1093 (2004)

[5] Alsahhaf TA, Kapetanovic E, Fluid Phase Equilib., 118(2), 271 (1996)

[6] Vakili-Nezhaad GR, Modarress H, Mansoori GA, Sep. Sci. Technol., 35(5), 743 (2000)

[7] Radwan GM, Almuhtaseb SA, Fahim MA, Fluid Phase Equilib., 129(1-2), 175 (1997)

[8] Jiao TT, Zhuang XL, He HY, Li CS, Chen HN, Zhang SJ, Ind. Eng. Chem. Res., 54(9), 2573 (2015)

[9] Jiao TT, Li CS, Zhuang XL, Cao SS, Chen HN, Zhang SJ, Chem. Eng. J., 266, 148 (2015)

[10] Kang HC, Kim SJ, Polycyclic Aromatic Compd., 36, 745 (2016)

[11] Kim SJ, Chun YJ, Sep. Sci. Technol., 40(10), 2095 (2005)

[12] Kim SJ, Polycyclic Aromatic Compd., 39, 60 (2019)

[13] Egashira R, Kawasaki J, J. Japan Pet. Inst., 40, 107 (1997)

[14] Kim SJ, Kang HC, Kim YS, Jeong HJ, Bull. Korean Chem. Soc., 31, 1143 (2010)

[15] Sharma A, Goswami AN, Rawat BS, Krishina R, J. Membr. Sci., 32, 19 (1987)

[16] Motoyuki M, Yamamoto K, Yoshida S, Yamamoto S, Sapre AV, McWilliams JP, Donnelly SP, Hellring SD, US Patent 6,018,087 (2000).

[17] Yamamoto Y, Sato Y, Ebina T, Yokoyama C, Takahasi S, Mito Y, Tanabe H, Nishiguchi N, Nagaoka K, Fuel, 70, 565 (1991)

[18] Motoyuki M, Yamamoto K, Sapre AV, McWilliams JP, Donnelly SP, US Patent 6,018,086 (2000).

[19] Uchida H, Iwai Y, Amiya M, Arai Y, Ind. Eng. Chem. Res., 36(2), 424 (1997)

[20] Xiong WP, Zeng GM, Yang ZH, Zhou YY, Zhang C, Cheng M, Liu Y, Hu LA, Wan J, Zhou CY, Xu R, Li X, Chemosphere, 210, 1061 (2018)

[21] Ahmed MJ, Environ. Toxicol. Pharmacol., 50, 1 (2017)

[22] Xiong WP, Tong J, Yang ZH, Zeng GM, Zhou YY, Wang DB, Song PP, Xu R, Zhang C, Cheng M, J. Colloid Interface Sci., 493, 17 (2017)

[23] Mochida I, Fei YQ, Sakanishi K, Chem. Lett., 515 (1990).

[24] Hall S, Tang R, Baeyens J, Dewil R, Polycyclic Aromatic Compd., 29, 160 (2009)

[25] Motoyuki M, Yamamoto K, Sapre AV, McWilliams JP, US Patent 6,011,190 (2000).

[26] McAuliffe C, Nature (December),1092 (1963).