Comparison of cellobiose and glucose transformation to ethylene glycol

doi:10.1016/S1872-2067(14)60151-0

Abstract

Abstract:

Cellobiose was used as a model feedstock to probe the reaction pathways of cellulose to ethylene glycol (EG). Its reactivity was compared with that of glucose using a catalyst composed of H₂WO₄ and Ru/C. EG can be produced by both the direct retro-aldol condensation of cellobiose and the retro-aldol condensation of glucose derived from cellobiose hydrolysis. The direct retro-aldol condensation of cellobiose further promoted the hydrolysis of cellobiose. Cellobiose has a lower reactivity for retro-aldol condensation than glucose, which decreased the formation rate of glycolaldehyde and made it more matched with the subsequent hydrogenation rate, thus leading to increased yield of EG from cellobiose.

Key words: Cellobiose, Reaction mechanism, Glucose, Ethylene glycol

Junying Zhang, Xiaofeng Yang, Baolin Hou, Aiqin Wang, Zhenlei Li, Hua Wang, Tao Zhang. Comparison of cellobiose and glucose transformation to ethylene glycol[J]. Chinese Journal of Catalysis, 2014, 35(11): 1811-1817.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(14)60151-0

https://www.cjcatal.com/EN/Y2014/V35/I11/1811

References

[1] Alonso D M, Bond J Q, Dumesic J A. Green Chem, 2010, 12: 1493
[2] Huber G W, Iborra S, Corma A. Chem Rev, 2006, 106: 4044
[3] Corma A, Iborra S, Velty A. Chem Rev, 2007, 107: 2411
[4] Dhepe P L, Fukuoka A. ChemSusChem, 2008, 1: 969
[5] Yu Y, Lou X, Wu H W. Energy Fuels, 2008, 22: 46
[6] Stöcker M. Angew Chem Int Ed, 2008, 47: 9200
[7] Rinaldi R, Schüth F. Energy Environ Sci, 2009, 2: 610
[8] Zhou C H, Xia X, Lin C X, Tong D S, Beltramini J. Chem Soc Rev, 2011, 40: 5588
[9] Kobayashi H, Komanoya T, Guha S K, Hara K, Fukuoka A. Appl Catal A, 2011, 409-410: 13
[10] Gallezot P. Chem Soc Rev, 2012, 41: 1538
[11] Wang Y L, Deng W P, Wang B J, Zhang Q H, Wan X Y, Tang Z C, Wang Y, Zhu C, Cao Z X, Wang G C, Wan H L. Nat Commun, 2013, 4: 2141
[12] Ma J P, Yu W Q, Wang M, Jia X Q, Lu F, Xu J. Chin J Catal (马继平, 于维强, 王敏, 贾秀全, 路芳, 徐杰. 催化学报), 2013, 34: 492
[13] Zhao C, Kou Y, Lemonidou A A, Li X B, Lercher J A. Angew Chem Int Ed, 2009, 48: 3987
[14] Alonso D M, Bond J Q, Dumesic J A. Green Chem, 2010, 12: 1493
[15] Peng B X, Yuan X G, Zhao C, Lercher J A. J Am Chem Soc, 2012, 134: 9400
[16] Li G Y, Li N, Li S S, Wang A Q, Cong Y, Wang X D, Zhang T. Chem Commun, 2013, 49: 5727
[17] Yang J F, Li N, Li G Y, Wang W T, Wang A Q, Wang X D, Cong Y, Zhang T. ChemSusChem, 2013, 6: 1149
[18] Wang S, Liu H C. Chin J Catal (王帅, 刘海超. 催化学报), 2014, 35: 631
[19] Zhang X C, Wang M, Wang Y H, Zhang C F, Zhang Z, Wang F, Xu J. Chin J Catal (张晓辰, 王敏, 王业红, 张超峰, 张哲, 王峰, 徐杰. 催化学报), 2014, 35: 703
[20] Dong X L, Xue S, Zhang J L, Huang W, Zhou J N, Chen Z A, Yuan D H, Xu Y P, Liu Z M. Chin J Catal (董兴隆, 薛松, 张今令, 黄为, 周建男, 陈兆安, 袁丹华, 徐云鹏, 刘中民. 催化学报), 2014, 35: 684
[21] Xiao Z H, Jin S H, Pang M, Liang C H. Green Chem, 2013, 15: 891
[22] Komanoya T, Kobayashi H, Hara K, Chun W J, Fukuoka A. ChemCatChem, 2014, 6: 230
[23] Ji N, Zhang T, Zheng M Y, Wang A Q, Wang H, Wang X D, Chen J G. Angew Chem Int Ed, 2008, 47: 8510
[24] Zhang Y H, Wang A Q, Zhang T. Chem Commun, 2010, 46: 862
[25] Zheng M Y, Wang A Q, Ji N, Pang J F, Wang X D, Zhan T. ChemSusChem, 2010, 3: 63
[26] Zhao G H, Zheng M Y, Wang A Q, Zhang T. Chin J Catal (赵冠鸿, 郑明远, 王爱琴, 张涛. 催化学报), 2010, 31: 928
[27] Pang J F, Zheng M Y, Wang A Q, Zhang T. Ind Eng Chem Res, 2011, 50: 6601
[28] Li C Z, Zheng M Y, Wang A Q, Zhang T. Energy Environ Sci, 2012, 5: 6383
[29] Ji N, Zheng M Y, Wang A Q, Zhang T, Chen J G. ChemSusChem, 2012, 5: 939
[30] Tai Z J, Zhang J Y, Wang A Q, Zheng M Y, Zhang T. Chem Commun, 2012, 48: 7052
[31] Tai Z J, Zhang J Y, Wang A Q, Pang J F, Zheng M Y, Zhang T. ChemSusChem, 2013, 6: 652
[32] Wang A Q, Zhang T. Acc Chem Res, 2013, 46: 1377
[33] Zhou L K, Pang J F, Wang A Q, Zhang T. Chin J Catal (周立坤, 庞纪峰, 王爱琴, 张涛. 催化学报), 2013, 34: 2041
[34] Zhao G H, Zheng M Y, Zhang J Y, Wang A Q, Zhang T. Ind Eng Chem Res, 2013, 52: 9566
[35] Zheng M Y, Pang J F, Wang A Q, Zhang T. Chin J Catal (郑明远, 庞纪峰, 王爱琴, 张涛. 催化学报), 2014, 35: 602
[36] Liu Y, Luo C, Liu H C. Angew Chem Int Ed, 2012, 51: 3249
[37] Huang Y B, Fu Y. Green Chem, 2013, 15: 1095
[38] Song J L, Fan H L, Ma J, Han B X. Green Chem, 2013, 15: 2619
[39] Kabyemela B M, Takigawa M, Adschiri T, Malaluan R M, Arai K. Ind Eng Chem Res, 1998, 37: 357
[40] Sasaki M, Furukawa M, Minami K, Adschiri T, Arai K. Ind Eng Chem Res, 2002, 41: 6642
[41] Yan N, Zhao C, Luo C, Dyson P J, Liu H C, Kou Y. J Am Chem Soc, 2006, 128: 8714
[42] Deng W P, Liu M, Tan X S, Zhang Q H, Wang Y. J Catal, 2010, 271: 22
[43] Delley B. J Chem Phys, 1990, 92: 508
[44] Delley B. J Chem Phys, 2000, 113: 7756
[45] Zhang J Y, Hou B L, Wang A Q, Li Z L, Wang H, Zhang T. AIChE J, 2014, DOI: 10.1002/aic.14554
[46] Zhang J Y, Hou B L, Wang A Q, Li Z L, Wang H, Zhang T. AIChE J, in Press