Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Glycerol Monostearate by Esterification on H3PW12O40/MCM-41 Catalyst
Corresponding Author(s) : Guomin Xiao
Asian Journal of Chemistry,
Vol. 26 No. 22 (2014): Vol 26 Issue 22
Abstract
H3PW12O40/MCM-41 solid-acid catalyst with different phosphotungstic acid (H3PW12O40) loadings was prepared by impregnation method and used in the esterification of glycerol with stearic acid using N,N-dimethyl formamide as solvent. The catalyst was characterized by FT-IR spectroscopy, transmission electron microscopy and scanning electron microscopy. The effects of catalyst preparation and esterification parameters such as reaction time, stearic acid/glycerol ratio and reaction temperature on esterification were investigated simultaneously. The results showed that H3PW12O40/MCM-41 had the best catalytic properties when the H3PW12O40 loading was 30 % and the use of DMF had a significant improvement on the yield of monoglyceride. Under a reaction condition of 6 h, 433 K and glycerol/acid molar ratio 6:1, 91 % selectivity of glycerol monosteatate was achieved with a stearic acid conversion of 98 %.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- T. Noyhouzer and D. Mandler, Anal. Chim. Acta, 684, 1 (2011); doi:10.1016/j.aca.2010.10.021.
- J.F. van Staden and M.C. Matoetoe, Anal. Chim. Acta, 411, 201 (2000); doi:10.1016/S0003-2670(00)00785-6.
- Y. Bonfil and E. Kirowa-Eisner, Anal. Chim. Acta, 457, 285 (2002); doi:10.1016/S0003-2670(02)00016-8.
- J. Wang, Ü. Anik Kirgöz, J.-W. Mo, J. Lu, A. Nasser Kawde and A. Muck, Electrochem. Commun., 3, 203 (2001); doi:10.1016/S1388-2481(01)00142-4.
- M. Chirea, V. García-Morales, J.A. Manzanares, C. Pereira, R. Gulaboski and F. Silva, J. Phys. Chem. B, 109, 21808 (2005); doi:10.1021/jp0537815.
- R.M. Iost and F.N. Crespilho, Biosens. Bioelectron., 31, 1 (2012); doi:10.1016/j.bios.2011.10.040.
- Y. Liu, X. Zou and S. Dong, Electrochem. Commun., 8, 1429 (2006); doi:10.1016/j.elecom.2006.06.024.
- L. Cao, Q. Li, J. Ji, P. Yan and T. Wang, Int. J. Electrochem. Soc., 8, 3074 (2013).
- N. Muskal and D. Mandler, Electrochim. Acta, 45, 537 (1999); doi:10.1016/S0013-4686(99)00232-7.
- S. Ben-Ali, D.A. Cook, P.N. Bartlett and A. Kuhn, J. Electroanal. Chem., 579, 181 (2005); doi:10.1016/j.jelechem.2004.11.018.
- S.Y. Li, W.H. Ma, Y. Zhou, X.H. Chen, M.Y. Ma, Y.H. Xu, Z. Ding and X.H. Wu, Int. J. Electrochem. Sci, 8, 1802 (2013).
- F. Ivanauskas, I. Kaunietis, V. Laurinavicius, J. Razumienė and R. Šimkus, J. Math. Chem., 43, 1516 (2008); doi:10.1007/s10910-007-9237-7.
- L. Chu and X. Zhang, J. Nanosci. Nanotechnol., 12, 300 (2012); doi:10.1166/jnn.2012.5132.
- Y.-C. Tsai, J.-M. Chen, S.-C. Li and F. Marken, Electrochem. Commun., 6, 917 (2004); doi:10.1016/j.elecom.2004.07.003.
- W. Sun, Z. Zhai, D. Wang, S. Liu and K. Jiao, Bioelectrochemistry, 74, 295 (2009); doi:10.1016/j.bioelechem.2008.11.001.
- R.G. Freitas, R.T.S. Oliveira, M.C. Santos, L.O.S. Bulhões and E.C. Pereira, Mater. Lett., 60, 1906 (2006); doi:10.1016/j.matlet.2005.12.050.
- D. Farina, K. Yoshida, T. Stieglitz and K.P. Koch, J. Appl. Physiol., 104, 821 (2008); doi:10.1152/japplphysiol.00788.2007.
- S. Schubert, M. Hermenau, J. Meiss, L. Müller-Meskamp and K. Leo, Adv. Funct. Mater., 22, 4993 (2012); doi:10.1002/adfm.201201592.
- M. Bonne, K. Edler, J.G. Buchanan, D. Wolverson, E. Psillakis, M. Helton, W. Thielemans and F. Marken, J. Phys. Chem. C, 112, 2660 (2008); doi:10.1021/jp709783k.
- S. Harrer, S. Ahmed, A. Afzali-Ardakani, B. Luan, P.S. Waggoner, X. Shao, H. Peng, D.L. Goldfarb, G.J. Martyna, S.M. Rossnagel, L. Deligianni and G.A. Stolovitzky, Langmuir, 26, 19191 (2010); doi:10.1021/la102671g.
- M. Musameh and J. Wang, Anal. Chim. Acta, 606, 45 (2008); doi:10.1016/j.aca.2007.11.012.
- D.V. Chernyshov, N.V. Shvedene, E.R. Antipova and I.V. Pletnev, Anal. Chim. Acta, 621, 178 (2008); doi:10.1016/j.aca.2008.05.042.
- D. Wei and A. Ivaska, Anal. Chim. Acta, 607, 126 (2008); doi:10.1016/j.aca.2007.12.011.
- T. Torimoto, T. Tsuda, K. Okazaki and S. Kuwabata, Adv. Mater., 22, 1196 (2010); doi:10.1002/adma.200902184.
- M.J.A. Shiddiky and A.A.J. Torriero, Biosens. Bioelectron., 26, 1775 (2011); doi:10.1016/j.bios.2010.08.064.
- M. Opallo and A. Lesniewski, J. Electroanal. Chem., 656, 2 (2011); doi:10.1016/j.jelechem.2011.01.008.
- H. Liu, Y. Liu and J. Li, Phys. Chem. Chem. Phys., 12, 1685 (2010); doi:10.1039/b921469k.
- M.G. Freire, C.M. Neves, I.M. Marrucho, J.A. Coutinho and A.M. Fernandes, J. Phys. Chem. A, 114, 3744 (2010); doi:10.1021/jp903292n.
- Y. Wang, J. Wu, T. Zhan, W. Sun and K. Jiao, Sensor Lett., 7, 1106 (2009); doi:10.1166/sl.2009.1243.
- Y. She, Y. Tang, H. Liu and P. He, Chem. Cent. J., 4, 17 (2010); doi:10.1186/1752-153X-4-17.
- Y. Feng, Z.X. Liu, L.Y. Wang, H. Chen, Y.M. He and Q.H. Fan, Chin. Sci. Bull., 57, 4289 (2012); doi:10.1007/s11434-012-5479-2.
- A. Safavi, N. Maleki, S. Momeni and F. Tajabadi, Anal. Chim. Acta, 625, 8 (2008); doi:10.1016/j.aca.2008.07.007.
- P. Zhang, S. Dong, G. Gu and T. Huang, Bull. Korean Chem. Soc., 31, 2949 (2010); doi:10.5012/bkcs.2010.31.10.2949.
- J. Ping, J. Wu, Y. Ying, M. Wang, G. Liu and M. Zhang, J. Agric. Food Chem., 59, 4418 (2011); doi:10.1021/jf200288e.
- B.L. Li, Z.L. Wu, C.H. Xiong, H.Q. Luo and N.B. Li, Talanta, 88, 707 (2012); doi:10.1016/j.talanta.2011.11.070.
- S.B. Hocevar, I. Švancara, K. Vytras and B. Ogorevc, Electrochim. Acta, 51, 706 (2005); doi:10.1016/j.electacta.2005.05.023.
- T. Fukushima, A. Kosaka, Y. Yamamoto, T. Aimiya, S. Notazawa, T. Takigawa, T. Inabe and T. Aida, Small, 2, 554 (2006); doi:10.1002/smll.200500404.
- T. Fukushima, A. Kosaka, Y. Ishimura, T. Yamamoto, T. Takigawa, N. Ishii and T. Aida, Science, 300, 2072 (2003); doi:10.1126/science.1082289.
- F. Zhao, X. Wu, M. Wang, Y. Liu, L. Gao and S. Dong, Anal. Chem., 76, 4960 (2004); doi:10.1021/ac0494026.
- W. Tao, D. Pan, Q. Liu, S. Yao, Z. Nie and B. Han, Electroanalysis, 18, 1681 (2006); doi:10.1002/elan.200603560.
- F. Xiao, L. Liu, J. Li, J. Zeng and B. Zeng, Electroanalysis, 20, 2047 (2008); doi:10.1002/elan.200804288.
- F. Xiao, F. Zhao, J. Zeng and B. Zeng, Electrochem. Commun., 11, 1550 (2009); doi:10.1016/j.elecom.2009.05.060.
- B.G. Choi, H. Park, T.J. Park, D.H. Kim, S.Y. Lee and W.H. Hong, Electrochem. Commun., 11, 672 (2009); doi:10.1016/j.elecom.2009.01.006.
- X. Liu, Z. Ding, Y. He, Z. Xue, X. Zhao and X. Lu, Colloids Surf. B, 79, 27 (2010); doi:10.1016/j.colsurfb.2010.03.009.
- J. Dong, Y. Hu, S. Zhu, J. Xu and Y. Xu, Anal. Bioanal. Chem., 396, 1755 (2010); doi:10.1007/s00216-009-3423-3.
References
T. Noyhouzer and D. Mandler, Anal. Chim. Acta, 684, 1 (2011); doi:10.1016/j.aca.2010.10.021.
J.F. van Staden and M.C. Matoetoe, Anal. Chim. Acta, 411, 201 (2000); doi:10.1016/S0003-2670(00)00785-6.
Y. Bonfil and E. Kirowa-Eisner, Anal. Chim. Acta, 457, 285 (2002); doi:10.1016/S0003-2670(02)00016-8.
J. Wang, Ü. Anik Kirgöz, J.-W. Mo, J. Lu, A. Nasser Kawde and A. Muck, Electrochem. Commun., 3, 203 (2001); doi:10.1016/S1388-2481(01)00142-4.
M. Chirea, V. García-Morales, J.A. Manzanares, C. Pereira, R. Gulaboski and F. Silva, J. Phys. Chem. B, 109, 21808 (2005); doi:10.1021/jp0537815.
R.M. Iost and F.N. Crespilho, Biosens. Bioelectron., 31, 1 (2012); doi:10.1016/j.bios.2011.10.040.
Y. Liu, X. Zou and S. Dong, Electrochem. Commun., 8, 1429 (2006); doi:10.1016/j.elecom.2006.06.024.
L. Cao, Q. Li, J. Ji, P. Yan and T. Wang, Int. J. Electrochem. Soc., 8, 3074 (2013).
N. Muskal and D. Mandler, Electrochim. Acta, 45, 537 (1999); doi:10.1016/S0013-4686(99)00232-7.
S. Ben-Ali, D.A. Cook, P.N. Bartlett and A. Kuhn, J. Electroanal. Chem., 579, 181 (2005); doi:10.1016/j.jelechem.2004.11.018.
S.Y. Li, W.H. Ma, Y. Zhou, X.H. Chen, M.Y. Ma, Y.H. Xu, Z. Ding and X.H. Wu, Int. J. Electrochem. Sci, 8, 1802 (2013).
F. Ivanauskas, I. Kaunietis, V. Laurinavicius, J. Razumienė and R. Šimkus, J. Math. Chem., 43, 1516 (2008); doi:10.1007/s10910-007-9237-7.
L. Chu and X. Zhang, J. Nanosci. Nanotechnol., 12, 300 (2012); doi:10.1166/jnn.2012.5132.
Y.-C. Tsai, J.-M. Chen, S.-C. Li and F. Marken, Electrochem. Commun., 6, 917 (2004); doi:10.1016/j.elecom.2004.07.003.
W. Sun, Z. Zhai, D. Wang, S. Liu and K. Jiao, Bioelectrochemistry, 74, 295 (2009); doi:10.1016/j.bioelechem.2008.11.001.
R.G. Freitas, R.T.S. Oliveira, M.C. Santos, L.O.S. Bulhões and E.C. Pereira, Mater. Lett., 60, 1906 (2006); doi:10.1016/j.matlet.2005.12.050.
D. Farina, K. Yoshida, T. Stieglitz and K.P. Koch, J. Appl. Physiol., 104, 821 (2008); doi:10.1152/japplphysiol.00788.2007.
S. Schubert, M. Hermenau, J. Meiss, L. Müller-Meskamp and K. Leo, Adv. Funct. Mater., 22, 4993 (2012); doi:10.1002/adfm.201201592.
M. Bonne, K. Edler, J.G. Buchanan, D. Wolverson, E. Psillakis, M. Helton, W. Thielemans and F. Marken, J. Phys. Chem. C, 112, 2660 (2008); doi:10.1021/jp709783k.
S. Harrer, S. Ahmed, A. Afzali-Ardakani, B. Luan, P.S. Waggoner, X. Shao, H. Peng, D.L. Goldfarb, G.J. Martyna, S.M. Rossnagel, L. Deligianni and G.A. Stolovitzky, Langmuir, 26, 19191 (2010); doi:10.1021/la102671g.
M. Musameh and J. Wang, Anal. Chim. Acta, 606, 45 (2008); doi:10.1016/j.aca.2007.11.012.
D.V. Chernyshov, N.V. Shvedene, E.R. Antipova and I.V. Pletnev, Anal. Chim. Acta, 621, 178 (2008); doi:10.1016/j.aca.2008.05.042.
D. Wei and A. Ivaska, Anal. Chim. Acta, 607, 126 (2008); doi:10.1016/j.aca.2007.12.011.
T. Torimoto, T. Tsuda, K. Okazaki and S. Kuwabata, Adv. Mater., 22, 1196 (2010); doi:10.1002/adma.200902184.
M.J.A. Shiddiky and A.A.J. Torriero, Biosens. Bioelectron., 26, 1775 (2011); doi:10.1016/j.bios.2010.08.064.
M. Opallo and A. Lesniewski, J. Electroanal. Chem., 656, 2 (2011); doi:10.1016/j.jelechem.2011.01.008.
H. Liu, Y. Liu and J. Li, Phys. Chem. Chem. Phys., 12, 1685 (2010); doi:10.1039/b921469k.
M.G. Freire, C.M. Neves, I.M. Marrucho, J.A. Coutinho and A.M. Fernandes, J. Phys. Chem. A, 114, 3744 (2010); doi:10.1021/jp903292n.
Y. Wang, J. Wu, T. Zhan, W. Sun and K. Jiao, Sensor Lett., 7, 1106 (2009); doi:10.1166/sl.2009.1243.
Y. She, Y. Tang, H. Liu and P. He, Chem. Cent. J., 4, 17 (2010); doi:10.1186/1752-153X-4-17.
Y. Feng, Z.X. Liu, L.Y. Wang, H. Chen, Y.M. He and Q.H. Fan, Chin. Sci. Bull., 57, 4289 (2012); doi:10.1007/s11434-012-5479-2.
A. Safavi, N. Maleki, S. Momeni and F. Tajabadi, Anal. Chim. Acta, 625, 8 (2008); doi:10.1016/j.aca.2008.07.007.
P. Zhang, S. Dong, G. Gu and T. Huang, Bull. Korean Chem. Soc., 31, 2949 (2010); doi:10.5012/bkcs.2010.31.10.2949.
J. Ping, J. Wu, Y. Ying, M. Wang, G. Liu and M. Zhang, J. Agric. Food Chem., 59, 4418 (2011); doi:10.1021/jf200288e.
B.L. Li, Z.L. Wu, C.H. Xiong, H.Q. Luo and N.B. Li, Talanta, 88, 707 (2012); doi:10.1016/j.talanta.2011.11.070.
S.B. Hocevar, I. Švancara, K. Vytras and B. Ogorevc, Electrochim. Acta, 51, 706 (2005); doi:10.1016/j.electacta.2005.05.023.
T. Fukushima, A. Kosaka, Y. Yamamoto, T. Aimiya, S. Notazawa, T. Takigawa, T. Inabe and T. Aida, Small, 2, 554 (2006); doi:10.1002/smll.200500404.
T. Fukushima, A. Kosaka, Y. Ishimura, T. Yamamoto, T. Takigawa, N. Ishii and T. Aida, Science, 300, 2072 (2003); doi:10.1126/science.1082289.
F. Zhao, X. Wu, M. Wang, Y. Liu, L. Gao and S. Dong, Anal. Chem., 76, 4960 (2004); doi:10.1021/ac0494026.
W. Tao, D. Pan, Q. Liu, S. Yao, Z. Nie and B. Han, Electroanalysis, 18, 1681 (2006); doi:10.1002/elan.200603560.
F. Xiao, L. Liu, J. Li, J. Zeng and B. Zeng, Electroanalysis, 20, 2047 (2008); doi:10.1002/elan.200804288.
F. Xiao, F. Zhao, J. Zeng and B. Zeng, Electrochem. Commun., 11, 1550 (2009); doi:10.1016/j.elecom.2009.05.060.
B.G. Choi, H. Park, T.J. Park, D.H. Kim, S.Y. Lee and W.H. Hong, Electrochem. Commun., 11, 672 (2009); doi:10.1016/j.elecom.2009.01.006.
X. Liu, Z. Ding, Y. He, Z. Xue, X. Zhao and X. Lu, Colloids Surf. B, 79, 27 (2010); doi:10.1016/j.colsurfb.2010.03.009.
J. Dong, Y. Hu, S. Zhu, J. Xu and Y. Xu, Anal. Bioanal. Chem., 396, 1755 (2010); doi:10.1007/s00216-009-3423-3.