Vapor phase condensation of ethyl lactate into lactide over SnO2/SiO2 catalyst

TitleVapor phase condensation of ethyl lactate into lactide over SnO2/SiO2 catalyst
Publication TypeJournal Article
Year of Publication2018
AuthorsVarvarin, AM, Levytska, SI, Brei, VV
Abbreviated Key TitleDopov. Nac. akad. nauk Ukr.
DOI10.15407/dopovidi2018.01.073
Issue1
SectionChemistry
Pagination73-79
Date Published1/2018
LanguageUkrainian
Abstract

The vapor phase conversion of 20 % solutions of ethyl lactate in cyclohexane into lactide over various oxides with the supported phase of SnO2 is investigated in the continuous regime at 200—260 °C. It was found that SnO2/SiO2 catalyst provides 40 % conversion of ethyl lactate with 44 % selectivity toward lactide at 250 °C. A scheme of lactide formation from ethyl lactate with the participation of L-acid sites of the SnO2 surface is discussed.

Keywordsethyl lactate, lactide, supported catalyst, tin dioxide, vapor phase conversion
References: 
  1. Pat 5142023 USA, IPC C08G 63/08, C07D 319/13, Continuous process for manufacture of lactide polymers with controlled optical purity, Gruber, P.R., Hall, E.S., Kolstad, J.J., Iwen, M.L., Benson, R.D., Borchardt, R.L., Publ. 25.08.1992.
  2. Auras, R., Lim, L.-T., Selke, S.E.M., Tsuji, H. (Eds). (2010). Poly(lactic acid): synthesis, structures, properties, processing and applications. Hoboken, New Jersey: John Wiley & Sons, Inc. doi: https://doi.org/10.1002/9780470649848
  3. Lactic acid and poly lactic acid (PLA) market analysis by application (packaging, agriculture, transport, electronics, textiles) and segment forecasts to 2020. Grand view research, 2014.
  4. Pat. 5374743 USA, IPC C07D 319/00, Process for the synthesis of lactide or glycolide from lactic acid or glycolide acid oligomers, Thayer, C.A., Bellis, H.E., Publ. 20.12.1994.
  5. Kolstad, J.J. (1996). Crystallization kinetics of poly(L-lactide-co-meso-lactide). J. Appl. Polym. Sci., 62, pp. 1079-1091. doi: https://doi.org/10.1002/(SICI)1097-4628(19961114)62:7<1079::AID-APP14>3.0.CO;2-1
  6. Pat. 5138074 USA, IPC C07D 319/12, C07D 321/00, Continuous catalysed vapor phase dimeric cyclic ester process, Bellis, H.E., Bhatia, K.K., Publ. 11.08.1992.
  7. Pat. 5319107 USA, IPC C07D 319/00, C07D 319/12, Method to produce cyclic esters, Benecke, H. P., Cheung, A., Cremeans, G. E., Hillman, M. E. D., Lipinsky, E. S., Markle, R. A., Sinclai, R. G., Publ. 07.06.1994.
  8. Upare, P. P., Hwang, Y. K., Chang, J.-S. & Hwang, D. W. (2012). Synthesis of lactide from alkyl lactate via a prepolymer route. Ind. Eng. Chem. Res., 51. pp. 4837-4842. doi: https://doi.org/10.1021/ie202714n
  9. Pereira, C. S. M., Silva, V. M. T. M. & Rodrigues, A. E. (2011). Ethyl lactate as a solvent: properties, applications and production — a review. Green Chem., 13, pp. 2658-2671. doi: https://doi.org/10.1039/c1gc15523g
  10. Brei, V. V., Levytska, S. I. & Shistka, D. V. (2013). Selective conversion of dihydroxyacetone –ethanol mixture to ethyl lactate over amphoteric ZrO2—TiO2 catalyst. Dopov. Nac. akad. nauk Ukr., No. 5, pp. 125-129 (in Russian).
  11. Brei, V. V. & Mylin, A. M. (2016). Selective conversion of glycerol solution in ethanol into ethyl lactate over CeO2/Al2O3 catalyst. Ukr. khim. zhurn., 71, pp. 79-83 (in Ukrainian).
  12. Tanabe, K. (1973). Solid acids and bases. Moscow: Mir (in Russian).
  13. Varvarin, A. M, Mylin, A. M. & Brei, V. V. (2017). Selective dehydration of ethyl lactate into ethyl acrylate over NaY-faujasite. Chem., Phys. and Technol. Surf., 8, pp. 165-174. doi: https://doi.org/10.15407/hftp08.02.165
  14. Tsukegi, T., Motoyama, T., Shirai, Y., Nishida, H. & Endo, T. (2007). Racemization behavior of L,L-lactide during heating. Polym. Degrad. Stab., 92, pp. 552-559. doi: https://doi.org/10.1016/j.polymdegradstab.2007.01.009