Condensation of alpha-Carbonyl Aldehydes Leads to the Formation of Solid Humins during the Hydrothermal Degradation of Carbohydrates

doi:10.1021/acsomega.9b00508

	Condensation of alpha-Carbonyl Aldehydes Leads to the Formation of Solid Humins during the Hydrothermal Degradation of Carbohydrates
	Shi, Ning 1; Liu, Qiying 2,3,4; Ju, Rongmei 1; He, Xiong 1; Zhang, Yulan 1; Tang, Shiyun 1; Ma, Longlong 2,3,4
刊名	ACS OMEGA
	2019-04-01
卷号	4 期号:4 页码:7330-7343
ISSN号	2470-1343
DOI	10.1021/acsomega.9b00508
通讯作者	Shi, Ning(shining@git.edu.cn)
英文摘要	Catalytic hydrothermal conversion of carbohydrates could provide a series of versatile valuable platform chemicals, but the formation of solid humins greatly decreased the efficiency of the process. Herein, by studying the hydrothermal degradation behavior and analyzing the degradation paths of kinds of model compounds including carbohydrates, furan compounds, cyclic ketone derivatives, and some simple short carbon-chain oxy-organics, we demonstrate that a-carbonyl aldehydes and alpha-carbonyl acids are the key primary precursors for humin formation during the hydrothermal conversion process. Then, we analyzed the hydrothermal degradation paths of two simple alpha-carbonyl aldehydes including glyoxal and pyruvaldehyde and found that the alpha-carbonyl aldehydes could undergo aldol condensation followed by acetal cyclization and dehydration to form solid humins rich of furan ring structure or undergo Cannizaro route (hydration followed by 1,2-hydride shift) to form corresponding alpha-hydroxy acids. On the basis of the hydrothermal behavior of the acarbonyl aldehydes, we mapped the hydrothermal degradation routes of carbohydrates (glucose, fructose, and xylose) and illuminated the formation details of alpha-carbonyl aldehydes, alpha-hydroxy acids, gamma-lactones, furfural derivatives, and humins. Finally, we deduced the typical structure fragments of humins from three alpha-carbonyl aldehydes of pyruvaldehyde, 2,5-dioxo-6-hydroxy-hexanal, and 3-deoxyglucosone, all of which could be formed during the hydrothermal degradation of hexose.
资助项目	Guizhou province science and technology plan project[[2017]5789-08] ; National Natural Science Foundation of China[51576199] ; Natural Science Foundation of Guangdong Province[2017A030308010]
WOS关键词	ACID-CATALYZED CONVERSION ; HIGH-YIELD PRODUCTION ; HOT COMPRESSED STEAM ; LACTIC-ACID ; STRUCTURAL-CHARACTERIZATION ; MOLECULAR-STRUCTURE ; LEVULINIC ACID ; CELLULOSE ; GLUCOSE ; DEHYDRATION
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000466552500135
资助机构	Guizhou province science and technology plan project ; National Natural Science Foundation of China ; Natural Science Foundation of Guangdong Province
内容类型	期刊论文
源URL	[http://ir.giec.ac.cn/handle/344007/25003]
专题	中国科学院广州能源研究所
通讯作者	Shi, Ning
作者单位	1.Guizhou Inst Technol, Sch Chem Engn, Guiyang 550003, Guizhou, Peoples R China 2.Chinese Acad Sci, Guangzhou Inst Energy Convers, Guangzhou 510640, Guangdong, Peoples R China 3.CAS Key Lab Renewable Energy, Guangzhou 510640, Guangdong, Peoples R China 4.Guangdong Prov Key Lab New & Renewable Energy Res, Guangzhou 510640, Guangdong, Peoples R China
推荐引用方式 GB/T 7714	Shi, Ning,Liu, Qiying,Ju, Rongmei,et al. Condensation of alpha-Carbonyl Aldehydes Leads to the Formation of Solid Humins during the Hydrothermal Degradation of Carbohydrates[J]. ACS OMEGA,2019,4(4):7330-7343.
APA	Shi, Ning.,Liu, Qiying.,Ju, Rongmei.,He, Xiong.,Zhang, Yulan.,...&Ma, Longlong.(2019).Condensation of alpha-Carbonyl Aldehydes Leads to the Formation of Solid Humins during the Hydrothermal Degradation of Carbohydrates.ACS OMEGA,4(4),7330-7343.
MLA	Shi, Ning,et al."Condensation of alpha-Carbonyl Aldehydes Leads to the Formation of Solid Humins during the Hydrothermal Degradation of Carbohydrates".ACS OMEGA 4.4(2019):7330-7343.