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Conversion of Cellulose to 5-Hydroxymethylfurfural in Water-Tetrahydrofuran and Byproducts Identification
Ning Shi,Qi-ying Liu,Tie-jun Wang*,Qi Zhang,Jun-ling Tu,Long-long Ma
Author NameAffiliationE-mail
Ning Shi CAS Key Laboratory of Renewable Energy, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, ChinaUniversity of Chinese Academy of Sciences, Beijing 100049, China  
Qi-ying Liu CAS Key Laboratory of Renewable Energy, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China  
Tie-jun Wang* CAS Key Laboratory of Renewable Energy, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China mall@ms.giec.ac.cn 
Qi Zhang CAS Key Laboratory of Renewable Energy, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China  
Jun-ling Tu CAS Key Laboratory of Renewable Energy, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, ChinaUniversity of Chinese Academy of Sciences, Beijing 100049, China  
Long-long Ma CAS Key Laboratory of Renewable Energy, Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China  
Abstract:
Conversion of cellulose into platform chemical 5-hydroxymethylfurfural (HMF) in water-tetrahydrofuran (THF) co-solvents under acidic condition was studied. 38.6% of HMF was obtained with low cellulose concentration of 2.4wt%, but levulinic acid (LA) and solid humins became the main products with high cellulose concentration. The soluble byproducts were analyzed by high performance liquid chromatography/multiple stage tandem mass spec-trometry, and chemicals with formula of C9H16O4、 C10H14O4、 C11H12O4、C12H10O5 and C12H16O8 were detected. THF could participate in the reaction via ring-opening into 1,4-butanediol followed by esterification with LA into C9H16O4 or etherification with HMF into C10H14O4. C11H12O4 was formed by esterification of HMF with LA, C12H10O5 was formed by self-etherification of HMF, while C12H16O8 was formed by acetalization of HMF with glucose. Self-etherification of HMF and etherification of HMF with 1,4-butanediol were identified as two main side reactions.
Key words:  Cellulose, 5-Hydroxymethylfurfural, Tetrahydrofuran, Etherification, High performance liquid chromatography/multiple stage tandem mass spectrometry
FundProject:
在水-四氢呋喃中纤维素转化为5-羟甲基糠醛及副产物鉴定
石宁,刘琪英,王铁军*,张琦,涂军令,马隆龙
摘要:
在酸性条件下,水-四氢呋喃混合溶剂中转化纤维素制备了平台化合物5-羟甲基糠醛(HMF).在纤维素浓度仅为2.4wt%时,可以得到38.6%的HMF,但是随着纤维素浓度的增加,胡敏素和乙酰丙酸成为主要产物.利用液相色谱-多级串联质谱联用技术检测到了分子式为C9H16O4、 C10H14O4、 C11H12O4、C12H10O5 和C12H16O8的一系列副产物.C9H16O4是通过四氢呋喃开环为1,4-丁二醇再与乙酰丙酸酯化反应得到,而C10H14O4是通过四氢呋喃开环后与HMF醚化得到.C11H12O4是由5-羟甲基糠醛与乙酰丙酸发生酯化反应得到,C12H10O5是由HMF自身醚化得到,而C12H16O8是HMF与葡萄糖经过缩醛反应得到.HMF的自身醚化反应及HMF与1,4-丁二醇的醚化反应是主要的副反应.
关键词:  纤维素,5-羟甲基糠醛,四氢呋喃,液相色谱-质谱联用
DOI:10.1063/1674-0068/27/06/711-717
分类号: