Separation of Dicyclopentaidene in a C5 stream using a tetraethoxydimethyl disiloxane-derived silica composite membrane

Hyeon-Gook Kim; Hye Ryeon Lee; Choong-Sun Lim; Bongkuk Seo

Journal of Industrial and Engineering Chemistry, Vol.79, 79-86, November, 2019

DOI10.1016/j.jiec.2019.05.016 Export Citation

Separation of Dicyclopentaidene in a C5 stream using a tetraethoxydimethyl disiloxane-derived silica composite membrane

Hyeon-Gook Kim, Hye Ryeon Lee, Choong-Sun Lim, and Bongkuk Seo^†

Advanced Industrial Chemistry Research Center, Advanced Convergent Chemistry Division, Korea Research Institute of Chemical Technology (KRICT), 45 Jonggaro, Ulsan, 44412 Korea

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Hybrid separation of dicyclopentadiene (DCPD) in a C5 stream was performed using a 1,1,3,3-tetraethoxy- 1,3-dimethyl disiloxane (TEDMDS)-derived silica composite membrane. High purity DCPD, the key monomer of the C5 stream can be concentrated by removing CPD through pervaporation from the CPDDCPD mixtures obtained by conventional distillation. Silica membranes were prepared using 1,1,3,3- tetraethoxy-1,3-dimethyl disiloxane (TEDMDS) by “spacer” and “template” techniques, which allowed for control the pore size of silica membranes using bridged alkoxides that have pendant groups. TEDMDSderived silica membranes calcined at 450 °C showed a high total flux of 0.06-0.5 kg·m-2 h-1 with a CPD separation factor of 6-33 in a 95 wt% DCPD mixture, for feed temperature of 50-70 °C. The silica membranes prepared in this study shows relatively a high flux and acceptable separation factor. Therefore, they may find applications in commercial processes alongside the conventional distillation, by saving energy and reducing byproducts.

Keywords:Dicyclopentadiene (DCPD);Hybrid separation;C5 stream;TEDMDS(1,1,3,3-tetraethoxy-1,3-dimethyl disiloxane);Pervaporation

[References]

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[2] Cai Z, Shen B, Liu W, Xin Z, Ling H, Energy Fuels, 23, 2077 (2009)

[3] Will R, Yoneyama M, Goh JT, Charlesworth R, Linak E, Ormonde E, DCPD and Piperylene, IHS CHEMICAL, Special Report Prospectus, (2015).

[4] Bondaletov VG, Manankova AA, Bondaletova LI, Vishnevskaya AL, Ogorodnikov VD, Bul. Tomsk Polytech. Univ., 311, 98 (2007)

[5] Sibi MG, Singh B, Kumar R, Pendem C, Sinha AK, Membr. J., 14, 976 (2012)

[6] Hsu HC, Wang SJ, Ou JDY, Wong DSH, Ind. Eng. Chem. Res., 54(40), 9798 (2015)

[7] Xiong ZQ, Mi ZT, Zhang XW, React. Kinet. Catal. Lett., 85(1), 89 (2005)

[8] Keenam MJ, Sharp DW, Schucker RC, Production of polymerization grade dicyclopentadiene, US Patent 5,401,891.

[9] Kim HG, Son HJ, Lee DK, Kim DW, Park HJ, Cho DH, Korean J. Chem. Eng., 34(7), 2099 (2017)

[10] Bergstrom C, Koskinen J, Halme E, Lindstrom M, Perala M, Method for preparing norbornene and substituted derivatives of norbornene US Patent, 6,294,706B1, (2001).

[11] Zou JJ, Zhang XW, Kong J, Wang L, Fuel, 87(17-18), 3655 (2008)

[12] Xing E, Zhang X, Wang L, Mi Z, Green Chem., 9, 589 (2007)

[13] Ma Y, Fu J, Gao Z, Zhang L, Li C, Wang T, Catalysts, 7, 103 (2017)

[14] Lin CM, Chen CH, Lin CH, Su WC, Juang TY, ACS Omega, 3, 4295 (2008)

[15] Kolon Industries Inc, Method for purification of dicyclopentadiene with falling film evaporating system KR100569591B1, (2002).

[16] Le NL, Nunes SP, Sustainable Mater.Technol., 7, 1 (2016)

[17] Shao P, Huang RYM, J. Membr. Sci., 287(2), 162 (2007)

[18] Wee SL, Tye CT, Bhatia S, Sep. Purif. Technol., 63(3), 500 (2008)

[19] Ravanchi MT, Kaghazchi T, Kargari A, Desalination, 235(1-3), 199 (2009)

[20] Nam SY, Membr. J., 17, 1 (2007)

[21] Smitha B, Suhanya D, Sridhar S, Ramakrishna M, J. Membr. Sci., 241(1), 1 (2004)

[22] van Wyk S, van der Ham AGJ, Kersten SRA, Chem. Eng. Process. Process Intensif., 130, 148 (2018)

[23] Tanaka K, Taguchi A, Hao JQ, Kita H, Okamoto K, J. Membr. Sci., 121(2), 197 (1996)

[24] Faiz R, Li K, Desalination, 287, 82 (2012)

[25] Chapman PD, Oliveira T, Livingston AG, Li K, J. Membr. Sci., 318(1-2), 5 (2008)

[26] Bolto B, Hoang M, Xie ZL, Chem. Eng. Process., 50(3), 227 (2011)

[27] Liu G, Wei W, Jin W, ACS Sustainable Chem. Eng., 2, 546 (2014)

[28] Villaluenga JPG, Tabe-Mohammadi A, J. Membr. Sci., 169(2), 159 (2000)

[29] Arruebo M, Falconer JL, Noble RD, J. Membr. Sci., 269(1-2), 171 (2006)

[30] Lee HR, Kanezashi M, Yoshioka T, Tsuru T, Desalin. Water Treat., 17, 120 (2010)

[31] Lee HR, Kanezashi M, Shimomura Y, Yoshioka T, Tsuru T, AIChE J., 57(10), 2755 (2011)

[32] Kanezashi M, Kawano M, Yoshioka T, Tsuru T, Ind. Eng. Chem. Res., 51, 944 (2012)

[33] Lee HR, Lee J, Seo B, J. Nanosci. Nanotechnol., 14, 8626 (2014)

[34] Lee HR, Seo B, Membr. J., 25, 15 (2015)

[35] Bowen TC, Li S, Noble RD, Falconer JL, J. Membr. Sci. 225, 165 (2003); given-name>Li, Noble RD, Falconer JL, J. Membr. Sci., 225, 165 (2003).

[36] Bondaletov VG, Manankova AA, Bondaletova LI, Vishnevskaya AL, Ogor-odnikov VD, Bull. Tomsk Polytech. Univ., 311(3), 98 (2007)