金属卤化物促进糖类催化转化制备5-羟甲基糠醛

引用本文: 任秋鹤, 黄义争, 马红, 高进, 徐杰. 金属卤化物促进糖类催化转化制备5-羟甲基糠醛[J]. 催化学报, 2014, 35(4): 496-500. doi: 10.1016/S1872-2067(14)60012-7 shu

Citation: Qiuhe Ren, Yizheng Huang, Hong Ma, Jin Gao, Jie Xu. Catalytic conversion of carbohydrates to 5-hydroxymethylfurfural promoted by metal halides[J]. Chinese Journal of Catalysis, 2014, 35(4): 496-500. doi: 10.1016/S1872-2067(14)60012-7 shu

金属卤化物促进糖类催化转化制备5-羟甲基糠醛

任秋鹤 ^a,b, ,
黄义争 ^a, ,
马红 ^a, ,
高进 ^a, ,
徐杰 ^{a,
,}

通讯作者: 徐杰

基金项目:
中国科学院知识创新工程重要方向项目(KSCX2-EW-G-5) (KSCX2-EW-G-5)

中国科学院战略性先导科技专项-应对气候变化的碳收支认证及相关问题(XDA05010203) (XDA05010203)

国家自然科学基金(21233008). (21233008)

摘要: 研究了碱金属卤化物对AlCl₃催化葡萄糖转化制备5-羟甲基糠醛(HMF)的促进作用. 结果表明, NaF对反应有显著抑制作用, 而NaI和NaBr对反应有显著促进作用, 而且NaI比NaBr的促进效果更明显. 在N, N-二甲基乙酰胺(DMAC)中, 以NaI为添加剂, 130 ℃反应15 min, AlCl₃催化葡萄糖转化制备HMF, 葡萄糖转化率由71%提高到86%, HMF收率由36%提高到62%. AlCl₃-NaI-DMAC体系也可用于果糖、甘露糖等单糖, 蔗糖、麦芽糖、纤维二糖等二糖, 以及菊粉等多糖的转化. 以蔗糖为原料, HMF收率可达63%.

关键词:

English

Catalytic conversion of carbohydrates to 5-hydroxymethylfurfural promoted by metal halides

Qiuhe Ren ^a,b, ,
Yizheng Huang ^a, ,
Hong Ma ^a, ,
Jin Gao ^a, ,
Jie Xu ^{a,
,}

1.
a Dalian National Laboratory for Clean Energy, State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;

Corresponding author: 徐杰

Received Date: 24 November 2013
Available Online: 20 April 2014
Fund Project:
中国科学院知识创新工程重要方向项目(KSCX2-EW-G-5)

中国科学院战略性先导科技专项-应对气候变化的碳收支认证及相关问题(XDA05010203)

国家自然科学基金(21233008).

Abstract: The promotion effect of alkali metal halides toward the AlCl₃-catalyzed conversion of glucose to 5-hydroxymethylfurfural (HMF) was investigated. The results show that NaF inhibited the reaction. However, NaI and NaBr promoted the reaction significantly, and the promotion effect of NaI was more obvious than that of NaBr. In N,N-dimethylacetamide (DMAC), when NaI was used as an additive for the AlCl₃-catalyzed conversion of glucose at 130 ℃ for 15 min, glucose conversion increased from 71% to 86%, and the HMF yield increased from 36% to 62%. The AlCl₃-NaI-DMAC system could also be used for the catalytic conversion of other carbohydrates such as fructose, mannose, sucrose, maltose, cellobiose, and inulin to HMF. When sucrose was used as the feedstock, a 63% HMF yield was achieved.

Key words:

1. [1] Yeh T M, Dickinson J G, Franck A, Linic S, Thompson L T, Savage P E. J Chem Technol Biotechnol, 2013, 88: 13[1] Yeh T M, Dickinson J G, Franck A, Linic S, Thompson L T, Savage P E. J Chem Technol Biotechnol, 2013, 88: 13
2. [2] Gallezot P. Chem Soc Rev, 2012, 41: 1538[2] Gallezot P. Chem Soc Rev, 2012, 41: 1538
3. [3] Zhou C H, Xia X, Lin C X, Tong D S, Beltramini J. Chem Soc Rev, 2011, 40: 5588[3] Zhou C H, Xia X, Lin C X, Tong D S, Beltramini J. Chem Soc Rev, 2011, 40: 5588
4. [4] Van Putten R J, Van Der Waal J C, De Jong E, Rasrendra C B, Heeres H J, De Vries J G. Chem Rev, 2013, 113: 1499[4] Van Putten R J, Van Der Waal J C, De Jong E, Rasrendra C B, Heeres H J, De Vries J G. Chem Rev, 2013, 113: 1499
5. [5] Rosatella A A, Simeonov S P, Frade R F M, Afonso C A M. Green Chem, 2011, 13: 754[5] Rosatella A A, Simeonov S P, Frade R F M, Afonso C A M. Green Chem, 2011, 13: 754
6. [6] 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[6] 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
7. [7] Nie J F, Xie J H, Liu H C. Chin J Catal (聂俊芳, 解佳翰, 刘海超. 催化学报), 2013, 34: 871[7] Nie J F, Xie J H, Liu H C. Chin J Catal (聂俊芳, 解佳翰, 刘海超. 催化学报), 2013, 34: 871
8. [8] Du Z T, Ma J P, Wang F, Liu J X, Xu J. Green Chem, 2011, 13: 554[8] Du Z T, Ma J P, Wang F, Liu J X, Xu J. Green Chem, 2011, 13: 554
9. [9] Ma J P, Du Z T, Xu J, Chu Q H, Pang Y. ChemSusChem, 2011, 4: 51[9] Ma J P, Du Z T, Xu J, Chu Q H, Pang Y. ChemSusChem, 2011, 4: 51
10. [10] Ma J P, Pang Y, Wang M, Xu J, Ma H, Nie X. J Mater Chem, 2012, 22: 3457[10] Ma J P, Pang Y, Wang M, Xu J, Ma H, Nie X. J Mater Chem, 2012, 22: 3457
11. [11] Ma J P, Wang M, Du Z T, Chen C, Gao J, Xu J. Polym Chem, 2012, 3: 2346[11] Ma J P, Wang M, Du Z T, Chen C, Gao J, Xu J. Polym Chem, 2012, 3: 2346
12. [12] Ma J P, Yu X F, Xu J, Pang Y. Polymer, 2012, 53: 4145[12] Ma J P, Yu X F, Xu J, Pang Y. Polymer, 2012, 53: 4145
13. [13] Che P H, Lu F, Zhang J J, Huang Y Z, Nie X, Gao J, Xu J. Bioresour Technol, 2012, 119: 433[13] Che P H, Lu F, Zhang J J, Huang Y Z, Nie X, Gao J, Xu J. Bioresour Technol, 2012, 119: 433
14. [14] Chen J Z, Lu F, Zhang J J, Yu W Q, Wang F, Gao J, Xu J. ChemCatChem, 2013, 5: 2822[14] Chen J Z, Lu F, Zhang J J, Yu W Q, Wang F, Gao J, Xu J. ChemCatChem, 2013, 5: 2822
15. [15] Jia X Q, Ma J P, Che P H, Lu F, Miao H, Gao J, Xu J. J Energy Chem, 2013, 22: 93[15] Jia X Q, Ma J P, Che P H, Lu F, Miao H, Gao J, Xu J. J Energy Chem, 2013, 22: 93
16. [16] Cai J Y, Ma H, Zhang J J, Song Q, Du Z T, Huang Y Z, Xu J. Chem Eur J, 2013, 19: 14215[16] Cai J Y, Ma H, Zhang J J, Song Q, Du Z T, Huang Y Z, Xu J. Chem Eur J, 2013, 19: 14215
17. [17] Qi X H, Guo H X, Li L Y, Smith R L. ChemSusChem, 2012, 5: 2215[17] Qi X H, Guo H X, Li L Y, Smith R L. ChemSusChem, 2012, 5: 2215
18. [18] Stahlberg T, Fu W J, Woodley J M, Riisager A. ChemSusChem, 2011, 4: 451[18] Stahlberg T, Fu W J, Woodley J M, Riisager A. ChemSusChem, 2011, 4: 451
19. [19] Roman-Leshkov Y, Chheda J N, Dumesic J A. Science, 2006, 312: 1933[19] Roman-Leshkov Y, Chheda J N, Dumesic J A. Science, 2006, 312: 1933
20. [20] Wang L, Zhang J, Zhu L F, Meng X J, Xiao F S. J Energy Chem, 2013, 22: 241[20] Wang L, Zhang J, Zhu L F, Meng X J, Xiao F S. J Energy Chem, 2013, 22: 241
21. [21] Karinen R, Vilonen K, Niemelae M. ChemSusChem, 2011, 4: 1002[21] Karinen R, Vilonen K, Niemelae M. ChemSusChem, 2011, 4: 1002
22. [22] Zhao H B, Holladay J E, Brown H, Zhang Z C. Science, 2007, 316: 1597[22] Zhao H B, Holladay J E, Brown H, Zhang Z C. Science, 2007, 316: 1597
23. [23] Yong G, Zhang Y G, Ying J. Angew Chem Int Ed, 2008, 47: 9345[23] Yong G, Zhang Y G, Ying J. Angew Chem Int Ed, 2008, 47: 9345
24. [24] Zhang Z H, Wang Q, Xie H B, Liu W J, Zhao Z B. ChemSusChem, 2011, 4: 131[24] Zhang Z H, Wang Q, Xie H B, Liu W J, Zhao Z B. ChemSusChem, 2011, 4: 131
25. [25] Hu S Q, Zhang Z F, Song J L, Zhou Y X, Han B X. Green Chem, 2009, 11: 1746[25] Hu S Q, Zhang Z F, Song J L, Zhou Y X, Han B X. Green Chem, 2009, 11: 1746
26. [26] Beckerle K, Okuda J. J Mol Catal A, 2012, 356: 158[26] Beckerle K, Okuda J. J Mol Catal A, 2012, 356: 158
27. [27] Rasrendra C B, Soetedjo J N M, Makertihartha I G B N, Adisasmito S, Heeres H J. Top Catal, 2012, 55: 543[27] Rasrendra C B, Soetedjo J N M, Makertihartha I G B N, Adisasmito S, Heeres H J. Top Catal, 2012, 55: 543
28. [28] Yan H P, Yang Y, Tong D M, Xiang X, Hu C W. Catal Commun, 2009, 10: 1558[28] Yan H P, Yang Y, Tong D M, Xiang X, Hu C W. Catal Commun, 2009, 10: 1558
29. [29] Ren Q H, Huang Y Z, Ma H, Wang F, Gao J, Xu J. Bioresources, 2013, 8: 1563[29] Ren Q H, Huang Y Z, Ma H, Wang F, Gao J, Xu J. Bioresources, 2013, 8: 1563
30. [30] Binder J B, Raines R T. J Am Chem Soc, 2009, 131: 1979[30] Binder J B, Raines R T. J Am Chem Soc, 2009, 131: 1979
31. [31] Lewkowski J. Arkivoc, 2001, 2: 17[31] Lewkowski J. Arkivoc, 2001, 2: 17
32. [32] Fagnou K, Lautens M. Angew Chem Int Ed, 2002, 41: 26[32] Fagnou K, Lautens M. Angew Chem Int Ed, 2002, 41: 26
33. [33] Maruoka K, Ooi T. Chem Eur J, 1999, 5: 829[33] Maruoka K, Ooi T. Chem Eur J, 1999, 5: 829
34. [34] Duquesnoy E, Castola V, Casanova J. Carbohydr Res, 2008, 343: 893[34] Duquesnoy E, Castola V, Casanova J. Carbohydr Res, 2008, 343: 893
35. [35] Roslund M U, Tähtinen P, Niemitz M, Sjöholm R. Carbohydr Res, 2008, 343: 101[35] Roslund M U, Tähtinen P, Niemitz M, Sjöholm R. Carbohydr Res, 2008, 343: 101
36. [36] Horvat J, Klaic B, Metelko B, Sunjic V. Tetrahedron Lett, 1985, 26: 2111[36] Horvat J, Klaic B, Metelko B, Sunjic V. Tetrahedron Lett, 1985, 26: 2111

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

金属卤化物促进糖类催化转化制备5-羟甲基糠醛

通讯作者: 徐杰

English

Catalytic conversion of carbohydrates to 5-hydroxymethylfurfural promoted by metal halides

Corresponding author: 徐杰

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

金属卤化物促进糖类催化转化制备5-羟甲基糠醛

通讯作者: 徐杰

English

Catalytic conversion of carbohydrates to 5-hydroxymethylfurfural promoted by metal halides

Corresponding author: 徐杰

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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