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Received July 11, 2018
Accepted December 5, 2018
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Integrated production of polymer-grade lactide from aqueous lactic acid by combination of heterogeneous catalysis and solvent crystallization with ethanol
1Green Carbon Catalysis Research Group, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeongro, Yuseoung, Daejeon 34114, Korea 2Department of Chemistry, Sungkyunkwan University, Suwon 16419, Korea 3Department of Advanced Materials and Chemical Engineering, University of Science and Technology (UST), 113 Gwahangno, Yuseong, Daejeon 34113, Korea
dwhwang@krict.re.kr
Korean Journal of Chemical Engineering, February 2019, 36(2), 203-209(7), 10.1007/s11814-018-0205-7
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Abstract
Lactide, a six-membered dimeric cyclic ester of lactic acid, is a key building block of polylatic acid, a representative bio-based biodegradable polymer. As an alternative to the conventional lactide production process of a twostep polymerization and depolymerization from lactic acid, we developed a novel continuous and one-step synthesis of optically pure lactide from lactic acid under atmospheric conditions with SnO2-SiO2 nanocomposites as heterogeneous catalyst. In this catalytic process, lactide was obtained in vapor phase together with water vapor and the unreacted lactic acid. After optimization of crystallization process using ethanol solvent, lactide crystals with 99 wt% purity and a lactide yield of 78 wt% were obtained. Based on these results, an integrated process for high-yield polymer-grade lactide production from aqueous lactic acid could be constructed by combination of the heterogeneous catalysis and crystallization with ethanol, which is more environmentally friendly as compared to the conventional two-step prepolymer process.
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References
Tuck CO, Perez E, Horvath IT, Sheldon RA, Poliakoff M, Science, 337(6095), 695 (2012)
Saygin D, Gielen DJ, Draeck M, Worrell E, Patel MK, Renew. Sust. Energ. Rev., 40, 1153 (2014)
Corma A, Iborra S, Velty A, Chem. Rev., 107(6), 2411 (2007)
Inkinen S, Hakkarainen M, Albertsson AC, Sodergard A, Biomacromol., 12, 523 (2011)
Jacobsen S, Degee PH, Fritz HG, Dubois PH, Jerome R, Polym. Eng. Sci., 39(7), 1311 (1999)
Saito N, Okada T, Horiuchi H, Murakami N, Takahashi J, Nawata M, Ota H, Nozaki K, Takaoka K, Nature Biotechnol., 19, 332 (2001)
Gruber PR, Hall ES, Kolstad JJ, Iwen ML, Benson RD, Borchardt RL, US Patent 5,247,059 (1993).
Meerdink J, Sadergard NDA, US Patent 8,053,584 B2 (2011).
Yoo DK, Kim D, Macromol. Res., 13, 510 (2006)
Upare PP, Hwang YK, Chang JS, Hwang DW, Ind. Eng. Chem. Res., 51(13), 4837 (2012)
Upare PP, Lee M, Hwang DW, Hwang YK, Chang JS, Catal. Commun., 56, 179 (2014)
Dusselier M, Van Wouwe P, Dewaele A, Jacobs PA, Sels BF, Science, 349(6243), 78 (2015)
Van Wouwe P, Dusselier M, Vanleeuw E, Sels B, ChemSusChem, 9, 907 (2016)
Upare PP, Yoon JW, Hwang DW, Lee UH, Hwang YK, Hong DY, Kim JC, Lee JH, Kwak SK, Shin H, Kim H, Chang JS, Green Chem., 18, 5978 (2016)
Yamaguchi Y, Arimura T, US Patent 5,502,215 (1996).
Tsukegi T, Motoyama T, Shirai Y, Nishida H, Endo T, Polymer Degrad. Stabil., 92, 552 (2007)
Koay GFL, Chuah TG, Zainal-Abidin S, Ahmad S, Choong TSY, Ind. Crop. Prod., 34, 1135 (2011)
Chen TC, Ju YH, Ind. Eng. Chem. Res., 40(17), 3781 (2001)
Xu WL, Huang YB, Qian JH, Sha O, Wang YQ, Sep. Purif. Technol., 41(2), 173 (2005)
Ohara H, Okuyama H, Ogaito M, Fujii Y, Kawamoto T, Kawabe T, Horibe Y, US Patent 6,313,319 B1 (2001).
Xiaoning L, Rongqing W, Ying L, Jun W, C.N. Patent 101,157,680 (2006).
Chen Z, Xie C, Xu Z, Wang YL, Zhao HP, Hao HX, J. Chem. Eng. Data, 58(1), 143 (2013)
Alfonsi K, Colberg J, Dunn PJ, Fevig T, Jennings S, Johnson TA, Kleine HP, Knight C, Nagy MA, Perry DA, Stefaniak M, Green Chem., 10, 31 (2008)
Erbetta CDC, Alves RJ, Resende JM, Freitas RFS, Sousa RS, J. Biomaterials Nanobiotechnol., 3, 208 (2012)
Saygin D, Gielen DJ, Draeck M, Worrell E, Patel MK, Renew. Sust. Energ. Rev., 40, 1153 (2014)
Corma A, Iborra S, Velty A, Chem. Rev., 107(6), 2411 (2007)
Inkinen S, Hakkarainen M, Albertsson AC, Sodergard A, Biomacromol., 12, 523 (2011)
Jacobsen S, Degee PH, Fritz HG, Dubois PH, Jerome R, Polym. Eng. Sci., 39(7), 1311 (1999)
Saito N, Okada T, Horiuchi H, Murakami N, Takahashi J, Nawata M, Ota H, Nozaki K, Takaoka K, Nature Biotechnol., 19, 332 (2001)
Gruber PR, Hall ES, Kolstad JJ, Iwen ML, Benson RD, Borchardt RL, US Patent 5,247,059 (1993).
Meerdink J, Sadergard NDA, US Patent 8,053,584 B2 (2011).
Yoo DK, Kim D, Macromol. Res., 13, 510 (2006)
Upare PP, Hwang YK, Chang JS, Hwang DW, Ind. Eng. Chem. Res., 51(13), 4837 (2012)
Upare PP, Lee M, Hwang DW, Hwang YK, Chang JS, Catal. Commun., 56, 179 (2014)
Dusselier M, Van Wouwe P, Dewaele A, Jacobs PA, Sels BF, Science, 349(6243), 78 (2015)
Van Wouwe P, Dusselier M, Vanleeuw E, Sels B, ChemSusChem, 9, 907 (2016)
Upare PP, Yoon JW, Hwang DW, Lee UH, Hwang YK, Hong DY, Kim JC, Lee JH, Kwak SK, Shin H, Kim H, Chang JS, Green Chem., 18, 5978 (2016)
Yamaguchi Y, Arimura T, US Patent 5,502,215 (1996).
Tsukegi T, Motoyama T, Shirai Y, Nishida H, Endo T, Polymer Degrad. Stabil., 92, 552 (2007)
Koay GFL, Chuah TG, Zainal-Abidin S, Ahmad S, Choong TSY, Ind. Crop. Prod., 34, 1135 (2011)
Chen TC, Ju YH, Ind. Eng. Chem. Res., 40(17), 3781 (2001)
Xu WL, Huang YB, Qian JH, Sha O, Wang YQ, Sep. Purif. Technol., 41(2), 173 (2005)
Ohara H, Okuyama H, Ogaito M, Fujii Y, Kawamoto T, Kawabe T, Horibe Y, US Patent 6,313,319 B1 (2001).
Xiaoning L, Rongqing W, Ying L, Jun W, C.N. Patent 101,157,680 (2006).
Chen Z, Xie C, Xu Z, Wang YL, Zhao HP, Hao HX, J. Chem. Eng. Data, 58(1), 143 (2013)
Alfonsi K, Colberg J, Dunn PJ, Fevig T, Jennings S, Johnson TA, Kleine HP, Knight C, Nagy MA, Perry DA, Stefaniak M, Green Chem., 10, 31 (2008)
Erbetta CDC, Alves RJ, Resende JM, Freitas RFS, Sousa RS, J. Biomaterials Nanobiotechnol., 3, 208 (2012)
