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高温下 5-羟甲基糠醛与咪唑基离子液体之间的意外反应。

An unexpected reaction between 5-hydroxymethylfurfural and imidazolium-based ionic liquids at high temperatures.

机构信息

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.

出版信息

Molecules. 2011 Oct 11;16(10):8463-74. doi: 10.3390/molecules16108463.

DOI:10.3390/molecules16108463
PMID:21989309
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6264421/
Abstract

A new compound was detected during the production of 5-hydroxymethylfurfural (HMF) from glucose and cellulose in the ionic liquid 1-butyl-3-methylimidazolium chloride ([Bmim]Cl) at high temperatures. Further experiments found that it was derived from the reaction of HMF with [Bmim]Cl. The structure of new compound was established as 1-butyl-2-(5'-methyl-2'-furoyl)imidazole (BMI) based on nuclear magnetic resonance and mass spectrometry analysis, and a possible mechanism for its formation was proposed. Reactions of HMF with other imidazolium-based ionic liquids were performed to check the formation of BMI. Our results provided new insights in terms of side reactions between HMF and imidazolium-based ionic liquids, which should be valuable for designing better processes for the production of furans using biomass and related materials.

摘要

在高温下，离子液体 1-丁基-3-甲基咪唑氯化物([Bmim]Cl)中葡萄糖和纤维素生成 5-羟甲基糠醛(HMF)的过程中检测到一种新的化合物。进一步的实验发现，它是由 HMF 与[Bmim]Cl 的反应生成的。根据核磁共振和质谱分析，确定新化合物的结构为 1-丁基-2-(5'-甲基-2'-糠酰基)咪唑(BMI)，并提出了其形成的可能机制。还进行了 HMF 与其他基于咪唑的离子液体的反应，以检查 BMI 的形成。我们的结果为 HMF 与基于咪唑的离子液体之间的副反应提供了新的见解，这对于使用生物质和相关材料设计生产呋喃的更好工艺应该是有价值的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/8a43d92db5c2/molecules-16-08463-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/403b85ae2616/molecules-16-08463-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/3f69ddcdd776/molecules-16-08463-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/f2c474508c68/molecules-16-08463-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/a0356adea750/molecules-16-08463-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/3db13d963d2d/molecules-16-08463-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/afe2454df04b/molecules-16-08463-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/9e49a145f5ff/molecules-16-08463-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/cbf5b8b621ac/molecules-16-08463-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/f01d28ccfdb8/molecules-16-08463-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/8a43d92db5c2/molecules-16-08463-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/403b85ae2616/molecules-16-08463-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/3f69ddcdd776/molecules-16-08463-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/f2c474508c68/molecules-16-08463-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/a0356adea750/molecules-16-08463-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/3db13d963d2d/molecules-16-08463-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/afe2454df04b/molecules-16-08463-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/9e49a145f5ff/molecules-16-08463-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/cbf5b8b621ac/molecules-16-08463-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/f01d28ccfdb8/molecules-16-08463-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2c3/6264421/8a43d92db5c2/molecules-16-08463-sch001.jpg

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Chem Rev. 2011 Feb 9;111(2):397-417. doi: 10.1021/cr100171a. Epub 2010 Oct 25.
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The presence of functional groups key for biodegradation in ionic liquids: effect on gas solubility.
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Microwave-assisted conversion of lignocellulosic biomass into furans in ionic liquid.微波辅助离子液体中木质纤维素生物质转化为呋喃。
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