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

doi:10.1021/acsomega.9b00508

GIEC OpenIR

	Condensation of alpha-Carbonyl Aldehydes Leads to the Formation of Solid Humins during the Hydrothermal Degradation of Carbohydrates
	Shi, Ning 1; Liu, Qiying2,3,4 ; Ju, Rongmei 1; He, Xiong 1; Zhang, Yulan 1; Tang, Shiyun 1; Ma, Longlong2,3,4
	2019-04-01
发表期刊	ACS OMEGA
ISSN	2470-1343
卷号	4 期号:4 页码:7330-7343
通讯作者	Shi, Ning(shining@git.edu.cn)
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.
DOI	10.1021/acsomega.9b00508
关键词[WOS]	ACID-CATALYZED CONVERSION ; HIGH-YIELD PRODUCTION ; HOT COMPRESSED STEAM ; LACTIC-ACID ; STRUCTURAL-CHARACTERIZATION ; MOLECULAR-STRUCTURE ; LEVULINIC ACID ; CELLULOSE ; GLUCOSE ; DEHYDRATION
收录类别	SCI
语种	英语
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研究方向	Chemistry
项目资助者	Guizhou province science and technology plan project ; National Natural Science Foundation of China ; Natural Science Foundation of Guangdong Province
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000466552500135
出版者	AMER CHEMICAL SOC
引用统计	被引频次：55[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.giec.ac.cn/handle/344007/25004
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.