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咪唑离子液体催化二糖一锅法转化为5-羟甲基糠醛

One-pot conversion of disaccharide into 5-hydroxymethylfurfural catalyzed by imidazole ionic liquid.

作者信息

Qu Yongshui, Li Li, Wei Quanyuan, Huang Chongpin, Oleskowicz-Popiel Piotr, Xu Jian

机构信息

State Key Laboratory of Biochemical Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing, 100190, China.

Beijing University of Chemical Technology, Beijing, 100029, China.

出版信息

Sci Rep. 2016 May 16;6:26067. doi: 10.1038/srep26067.

DOI:10.1038/srep26067
PMID:27181523
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4867639/
Abstract

Conversion of carbohydrate into 5-hydroxymethylfurfural (5- HMF), a versatile, key renewable platform compound is regarded as an important transformation in biomass-derived carbohydrate chemistry. A variety of ILs, not only acidic but also alkaline ILs, were synthesized and used as catalyst in the production of 5-HMF from disaccharide. Several factors including reaction temperature, IL dosage, solvent and reaction time,were found to influence the yield of 5-HMF from cellobiose. Of the ILs tested, hydroxy-functionalized ionic liquid (IL), 1-hydroxyethyl-3-methylimidazolium tetrafluoroborate ([AEMIM]BF4) showed the highest catalytic activity and selectivity. 5-HMF yield of 68.71% from sucrose was obtained after 6 hrs at 160 °C. At the same condition with cellobiose as substrate, 5-HMF yield was 24.73%. In addition, 5-HMF also exhibited good stablity in this reaction system. Moreover, a kinetic analysis was carried out in both acidic and alkaline IL-catalyzed system, suggesting main side reaction in the conversion of fructose catalyzed by acidic and alkaline IL was polymerization of fructose and 5-HMF degradation, respectively.

摘要

将碳水化合物转化为5-羟甲基糠醛(5-HMF),一种用途广泛的关键可再生平台化合物,被视为生物质衍生碳水化合物化学中的重要转化。合成了多种离子液体(ILs),不仅有酸性离子液体,还有碱性离子液体,并将其用作从二糖生产5-HMF的催化剂。发现包括反应温度、离子液体用量、溶剂和反应时间在内的几个因素会影响从纤维二糖生产5-HMF的产率。在所测试的离子液体中,羟基官能化离子液体(IL),1-羟乙基-3-甲基咪唑四氟硼酸盐([AEMIM]BF4)表现出最高的催化活性和选择性。在160℃下反应6小时后,蔗糖的5-HMF产率达到68.71%。在以纤维二糖为底物的相同条件下,5-HMF产率为24.73%。此外,5-HMF在该反应体系中也表现出良好的稳定性。此外,还对酸性和碱性离子液体催化体系进行了动力学分析,表明酸性和碱性离子液体催化果糖转化过程中的主要副反应分别是果糖聚合和5-HMF降解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/23fb8b0d0e45/srep26067-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/6341ab3d8795/srep26067-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/906a0a93da64/srep26067-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/dd3e88b2e6a3/srep26067-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/3a9d26e12bf3/srep26067-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/4f91fa7d1ab9/srep26067-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/23fb8b0d0e45/srep26067-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/6341ab3d8795/srep26067-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/906a0a93da64/srep26067-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/dd3e88b2e6a3/srep26067-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/3a9d26e12bf3/srep26067-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/4f91fa7d1ab9/srep26067-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5291/4867639/23fb8b0d0e45/srep26067-f6.jpg

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