Chinese Journal of Organic Chemistry >
Application of Polymeric Ionic Liquids in the Catalytic Conversion of Fructose to Lactic Acid
Received date: 2014-08-28
Revised date: 2014-09-26
Online published: 2014-10-30
Supported by
Project supported by the National Natural Science Foundation of China (No. 21476021) and the National Basic Research Program of China (No. 2010CB226902).
Preparation of lactic acid via chemical transformation of carbohydrates requires rigorous reaction conditions, such as high concentrations of alkali, high temperature, etc. This paper reports the use of polymeric ionic liquids ([IMEP]Cl) as catalyst for the hydrothermal conversion of fructose to lactic acid; the main variables of the reaction, temperature, substrate concentration, as well as the relative amount of [IMEP]Cl and NaOH were optimized. Results showed that, at 100 ℃, substrate concentration of 25 mmol/L, reaction time of 30 min, the highest yield of lactic acid was 65% with [IMEP]Cl and NaOH concentrations of 100 and 50 mmol/L respectively. This method reduces the reaction temperature and alkali concentration compared to traditional hydrothermal method, additionally it was found that [IMEP]Cl can be used during 5 catalytic cycles without losing its catalytic effect with a lactic acid yield of 55% in the 5th reuse cycle. This demonstrates that the use of polymer ionic liquids as catalysts has a better prospect for future developments. A possible reaction mechanism has been proposed, but further investigation is required.
Key words： polymeric ionic liquids; fructose; lactic acid
Wang Yamei , Wang Xincheng , Li Shunjie , Huang Chongpin , Song Yanlei , Chen Biaohua . Application of Polymeric Ionic Liquids in the Catalytic Conversion of Fructose to Lactic Acid[J]. Chinese Journal of Organic Chemistry, 2015 , 35(2) : 404 -410 . DOI: 10.6023/cjoc201408034
[1] Keshwani, D. R.; Cheng, J. J. Bioresour. Technol. 2009, 100(4), 1515.
[2] Sims, R. E. H.; Mabee, W.; Saddler, J. N.; Taylor, M. Bioresour. Technol. 2010, 101(6), 1570.
[3] Rom, L. Y.; Barrettc, J.; Liu, Z. Y. Nat. Biotechnol. 2007, 447, 982.
[4] Chang, C. Ph.D. Dissertation, Institute of Bioengineering, Zhejiang University, Hangzhou, 2006 (in Chinese). (常春, 博士论文, 浙江大学生物工程研究所, 杭州, 2006.)
[5] Zhu, G.-Y.; Ma, Y.-H.; Zhu, X. Chin. J. Org. Chem. 2010, 30, 142 (in Chinese). (朱广用, 马艳华, 朱宪, 有机化学, 2010, 30, 142.)
[6] Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044.
[7] Demirbas, M. F.; Balat, M. Energy Convers. Manage. 2006, 47(15～16), 2371.
[8] Gallezot, P. Chem. Soc. Rev. 2012, 41, 1538.
[9] Chandel, A. K.; da Silva, S. S.; Carvalho, W.; Singh, O. V. J. Chem. Technol. Biotechnol. 2012, 87(1), 11.
[10] Liu, Z. Ph.D. Dissertation, Zhejiang University, Hangzhou, 2012 (in Chinese). (刘镇, 博士论文, 浙江大学, 杭州, 2012.)
[11] San-Martin, M.; Pazos, C.; Coca, J. J. Chem. Technol. Biotechnol. 1992, 54, 1e6.
[12] Epane, G.; Laguerre, J. C.; Wadouachi, A.; Marek, D. Green Chem. 2010, 12(3), 502.
[13] Gao, C.; Ma, C.; Xu, P. Biotechnol. Adv. 2011, 29(6), 930.
[14] Bai, D.; Zhao, X.; Li, X.; Xu, S. Biochem. Eng. J. 2004, 18(1), 41.
[15] Salminen, S.; Ouwehand, A.; Wright, A. V.; Daly, C. Ann. N. Y. Acad. Sci. 1993, 429.
[16] Zeng, W.; Chen, F.-Q.; Zhan, X.-L; Chem. Ind. Eng. Progr. 2006, 25(7), 744 (in Chinese). (曾炜, 陈丰秋, 詹晓力, 化工进展 2006, 25(7), 744.)
[17] Wasewar, K. L.; Yawalkar, A. A.; Moulijn, J. A.; Pangarkar, V. G. Ind. Eng., Chem. Res. 2004, 43(19), 5969.
[18] Aida, T. M.; Tajima, K.; Watanabe, M.; Saito, Y.; Kuroda, K.; Nonaka, T.; Hattori, H.; Smith, R. L.; Arai, K. J. Supercrit. Fluids 2007, 42(1s), 110.
[19] Onda, A.; Ochi, T.; Kajiyoshi, K.; Yanagisawa, K. Catal. Commol.2008, 9(6), 1050.
[20] Onda, A.; Ochi, T.; Kajiyoshi, K.; Yanagisawa, K. Appl. Catal. A 2008, 343(1～2), 49.
[21] Yan, X.-Y.; Jin, F.-M.; Tohji, K.; Kishita, A.; Enomoto, H. AIChE J. 2010, 56, 2727.
[22] Zhang, S.-P.; Jin, F. -M.; Hu, J.-J.; Huo, Z.-B. Bioresour. Technol. 2010, 102(2011), 1998.
[23] Rasrendra, C. B.; Makertihartha, I.; Adisasmito, S.; Heeres, H. J. Top. Catal. 2010, 53(15～18), 1241.
[24] Hayashi, Y.; Sasaki, Y. Chem. Commol/Lun. 2005, 41(21), 2716。
[25] Holm, M. S.; Saravanamurugan, S.; Taarning, E. Science 2010, 328, 602.
[26] Chambon, F.; Rataboul, F.; Pinel, C.; Cabiac, A.; Guillon, E.; Essayem, N. Appl. Catal. B 2011, 105, 171.
[27] (a) Aslanov, L. A.; Zakharov, V. N.; Savilov, S. V. RU 2471709, 2013 [Chenm. Abstr. 2013, 158, 162458].
(b) Patil, A. B.; Pathak, P.; Shinde, V. S.; Godbole, S. V.; Mohahapatra, P. K. Dalton Trans. 2013, 42(5), 1519.
(c) Luo, S.-Z.; Mi, X.-L.; Zhang, L.; Liu, S.; Xu, H.; Cheng, J.-P. Tetrahedron 2007, 1923.
[28] Song, Y.-L.; Wang, X.-C.; Huang, C.-P.; Liang, F.-B.; Chen, B.-H. Chin. J. Org. Chem. 2013, 33, 1715 (in Chinese). (宋彦磊, 王新承, 黄崇品, 梁凤兵, 毓志超, 陈标华, 有机化学, 2013, 33, 1715.)
[29] Gao, Y.-J. M.S. Thesis, Zhejiang Normal University, Jinhua, 2009 (in Chinese). (高尤剑, 硕士论文, 浙江师范大学, 金华, 2009.)
[30] Wei, Z.-Z. M.S. Thesis, Shandong University, Jinan, 2012 (in Chinese). (韦珍珍, 硕士论文, 山东大学, 济南, 2012.)
[31] Li, J.; Sun, H.; Cai, X.-C.; Dai, L.-Y. Chin. J. Org. Chem. 2007, 27, 1296 (in Chinese). (李娟, 孙辉, 蔡晓晨, 戴立益, 有机化学, 2007, 27, 1296.)
[32] Hirao, M.; Ito, K.; Ohno, H. Electrochim. Acta 2000, 45, 1291.
[33] Shaplov, A. S.; Lozinskaya, E. I.; Ponkratov, D. O.; Malyshkina, I. A.; Vidal, F.; Aubert, P. H.; Okatova, O. V.; Pavlov, G. M.; Komarova, L. I.; Wandrey, C.; Vygodskii, Y. S. Electrochim. Acta 2011, 57, 74.
[34] Ohno, H.; Ito, K. Chem. Lett. 1998, 27, 751.
[35] Hirao, M.; Ito, K.; Ohno, H. Polym. Adv. Technol. 2000, 11, 534.
[36] Zhang, H.; Zhou, Z. -B.; Nie, J. Prog. Chem. 2013, 25(5), 761 (in Chinese). (张恒, 周志彬, 聂进, 化学进展, 2013, 25(5), 761.)
[37] He, H.-Y.; Zhang, S.-J.; Liu, X.-M.; Wang, J.-W.; Yao, X.-Q.; Zhang, X.-P. Fluid Phase Equilib. 2013, 169.
[38] Yan, R.-Y.; Yang, P.; Li, Z.-X.; Wang, H.; Diao, Y.-Y.; Wang, L.; Zhang, S.-J. Adv. Mater. Res. 2011, 1146.
[39] Dong, K.; Song, Y.-T.; Liu, X.-M.; Cheng, W.-G.; Yao, X. -Q.; Zhang, S.-J. J. Phys. Chem. B 2011, 1007.
[40] Kanazawa, A.; Ikeda, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 1099.
[41] Bicker, M.; Endres, S.; Ott, L.; Vogel, H. Mol. J. Catal. A: Chem.2005, 239, 151.
[42] Ellis, A. V.; Wilson, M. A. J. Org. Chem. 2002, 67, 8469.
[43] Rasrendra, C. B.; Fachri, B. A.; Makertihartha, I. G. B. N.; Adisasmito, S.; Heeres, H. J. ChemSusChem 2011, 4, 768.
/
| 〈 |
|
〉 |
