Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein

doi:10.1002/cssc.201601267

	Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein
	Li, Lin 2; Wang, Aiqin 2; Zhang, Tao 1,2; Dai, Tao 2; Li, Changzhi 2; Zhang, Bo 2; Guo, Haiwei 1,2; Pan, Xiaoli 2
刊名	CHEMSUSCHEM
	2016-12-20
卷号	9 期号:24 页码:3434-3440
关键词	Biomass Decarbonylation Dehydrogenation Diels-alder Reaction Toluene
ISSN号	1864-5631
DOI	10.1002/cssc.201601267
文献子类	Article
英文摘要	Toluene is a basic chemical that is currently produced from petroleum resources. In this paper, we report a new route for the effective synthesis of toluene from isoprene and acrolein, two reactants readily available from biomass, through a simple two-step reaction. The process includes Diels-Alder cycloaddition of isoprene and acrolein in a Zn-containing ionic liquid at room temperature to produce methylcyclohex-3-enecarbaldehydes (MCHCAs) as intermediates, followed by M (M = Pt, Pd, Rh)/Al2O3-catalyzed consecutive dehydrogenation-decarbonylation of the MCHCAs at 573 K to generate toluene with an overall yield up to 90.7 %. Model reactions indicated that a synergistic inductive effect of the C=C double bond and the aldehyde group in MCHCA plays a key role in initiating the consecutive dehydrogenation-decarbonylation, and that methyl benzaldehydes are the key intermediates in the gas-phase transformation of MCHCAs. Microcalorimetric adsorption of CO on different catalysts showed that decarbonylation of the substrate occurs more likely on the strong adsorption sites. To the best of our knowledge, it is the first report of Pt/Al2O3-catalyzed consecutive dehydrogenation-decarbonylation of a given compound in one reactor. This work provides a highly efficient and environmental friendly route to toluene by utilizing two compounds that can be prepared from biomass.
WOS关键词	METHYLERYTHRITOL PHOSPHATE-PATHWAY ; DIELS-ALDER ; P-XYLENE ; SUSTAINABLE PRODUCTION ; TEREPHTHALIC ACID ; ACRYLIC-ACID ; ACTIVE-SITE ; M-CRESOL ; CATALYSTS ; PHASE
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000394571500011
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/169636]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Zhang, Tao; Li, Changzhi
作者单位	1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
推荐引用方式 GB/T 7714	Li, Lin,Wang, Aiqin,Zhang, Tao,et al. Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein[J]. CHEMSUSCHEM,2016,9(24):3434-3440.
APA	Li, Lin.,Wang, Aiqin.,Zhang, Tao.,Dai, Tao.,Li, Changzhi.,...&Pan, Xiaoli.(2016).Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein.CHEMSUSCHEM,9(24),3434-3440.
MLA	Li, Lin,et al."Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein".CHEMSUSCHEM 9.24(2016):3434-3440.