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Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein
Dai, Tao1; Li, Changzhi1; Zhang, Bo1; Guo, Haiwei1,2; Pan, Xiaoli1; Li, Lin1; Wang, Aiqin1; Zhang, Tao1,2
KeywordBiomass Decarbonylation Dehydrogenation Diels-alder Reaction Toluene
Source PublicationCHEMSUSCHEM
2016-12-20
ISSN1864-5631
DOI10.1002/cssc.201601267
Volume9Issue:24Pages:3434-3440
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordMETHYLERYTHRITOL PHOSPHATE-PATHWAY ; DIELS-ALDER ; P-XYLENE ; SUSTAINABLE PRODUCTION ; TEREPHTHALIC ACID ; ACRYLIC-ACID ; ACTIVE-SITE ; M-CRESOL ; CATALYSTS ; PHASE
AbstractToluene 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.
Language英语
WOS IDWOS:000394571500011
PublisherWILEY-V C H VERLAG GMBH
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/169637
Collection中国科学院大连化学物理研究所
Corresponding AuthorLi, Changzhi; Zhang, Tao
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Dai, Tao,Li, Changzhi,Zhang, Bo,et al. Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein[J]. CHEMSUSCHEM,2016,9(24):3434-3440.
APA Dai, Tao.,Li, Changzhi.,Zhang, Bo.,Guo, Haiwei.,Pan, Xiaoli.,...&Zhang, Tao.(2016).Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein.CHEMSUSCHEM,9(24),3434-3440.
MLA Dai, Tao,et al."Selective Production of Toluene from Biomass-Derived Isoprene and Acrolein".CHEMSUSCHEM 9.24(2016):3434-3440.
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