Effect of organic solvent and Brønsted acid on 5-hydroxymethylfurfural preparation from glucose over CrCl3

作者: Yan Yang , Wentao Liu , Ningning Wang , Haijun Wang , Zhanxin Song

DOI: 10.1039/C5RA02057C

关键词:

摘要: In the present work, influence of organic solvent on mechanism 5-hydroxymethylfurfural (HMF) preparation from glucose over CrCl3 and role Bronsted acid (N-methyl-2-pyrrolidone hydrogen sulfate ([NMP]HSO4), N-methyl-2-pyrrolidone bromide ([NMP]Br), chlorine ([NMP]Cl), H2SO4, HBr HCl) during reaction were researched by a complementary computational experimental study. It was found that dimethyl sulfoxide (DMSO) gave lowest conversion surrounding CrCl3, forming six-coordinated structure (CrCl3–3DMSO). Glucose in N,N-dimethylformamide (DMF) not selective. N,N-Dimethylacetamide (DMA) n-butyl alcohol exhibited superior selectivity towards HMF glucose. Then different acids DMA expounded. On increasing dosage [NMP]HSO4, decreased. A study HSO4− could also combine with six-coordinate complexes. Addition [NMP]Br [NMP]Cl accelerated generation significantly but didn’t increase yield. An method preliminarily confirmed they mainly responsible for fructose dehydration to HMF. subsequent further verified two kinds ILs had no effect isomerization.

参考文章(42)
X.U. Junming, Jiang Jianchun, Zuo Zhiyue, Li Jing, Synthesis of tributyl citrate using acid ionic liquid as catalyst Process Safety and Environmental Protection. ,vol. 88, pp. 28- 30 ,(2010) , 10.1016/J.PSEP.2009.11.002
Shunmugavel Saravanamurugan, Marta Paniagua, Juan A Melero, Anders Riisager, None, Efficient isomerization of glucose to fructose over zeolites in consecutive reactions in alcohol and aqueous media. Journal of the American Chemical Society. ,vol. 135, pp. 5246- 5249 ,(2013) , 10.1021/JA400097F
C. Adamo, V. Barone, Toward reliable adiabatic connection models free from adjustable parameters Chemical Physics Letters. ,vol. 274, pp. 242- 250 ,(1997) , 10.1016/S0009-2614(97)00651-9
Suqin Hu, Zhaofu Zhang, Jinliang Song, Yinxi Zhou, Buxing Han, Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid Green Chemistry. ,vol. 11, pp. 1746- 1749 ,(2009) , 10.1039/B914601F
Emiel J. M. Hensen, Gang Yang, Evgeny A. Pidko, The Mechanism of Glucose Isomerization to Fructose over Sn‐BEA Zeolite: A Periodic Density Functional Theory Study Chemsuschem. ,vol. 6, pp. 1688- 1696 ,(2013) , 10.1002/CSSC.201300342
Jan A. Geboers, Stijn Van de Vyver, Roselinde Ooms, Beau Op de Beeck, Pierre A. Jacobs, Bert F. Sels, Chemocatalytic conversion of cellulose: opportunities, advances and pitfalls Catalysis Science & Technology. ,vol. 1, pp. 714- 726 ,(2011) , 10.1039/C1CY00093D
Yuriy Román-Leshkov, Juben N Chheda, James A Dumesic, Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose Science. ,vol. 312, pp. 1933- 1937 ,(2006) , 10.1126/SCIENCE.1126337
Yongshui Qu, Chongpin Huang, Yanlei Song, Jie Zhang, Biaohua Chen, Efficient dehydration of glucose to 5-hydroxymethylfurfural catalyzed by the ionic liquid,1-hydroxyethyl-3-methylimidazolium tetrafluoroborate. Bioresource Technology. ,vol. 121, pp. 462- 466 ,(2012) , 10.1016/J.BIORTECH.2012.06.081
Bing Liu, Zehui Zhang, Zongbao Kent Zhao, Microwave-assisted catalytic conversion of cellulose into 5-hydroxymethylfurfural in ionic liquids Chemical Engineering Journal. ,vol. 215, pp. 517- 521 ,(2013) , 10.1016/J.CEJ.2012.11.019