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MECHANISTIC STUDY OF THE CONVERSION FROM DMDFC TO DOHE IN THE LEVULINIC ACID FORMATION PROCESS BY THEORETICAL APPROACHES
Alternative TitleBioResources
Wang, Ze; Lin, Weigang; Song, Wenli
2011
Source PublicationBIORESOURCES
ISSN1930-2126
Volume6Issue:2Pages:1858-1867
AbstractA reaction route accounting for the formation of levulinic acid from 5-hydroxymethylfuran-2-carbaldehyde was deduced on the basis of the mechanism previously offered by Horvat, to match the steps with more details. A newly deduced reaction route was proposed between two intermediate products within this mechanism, and the probabilities of the two mechanisms were compared by Gaussian 03 software. It was found that the conversion from the intermediate 2,3-dihydroxy-5-methyl-2,3-dihydro-furan-2-carbaldehyde (DMDFC) to 2,5-dioxo-hex-3-enal (DOHE) in the original mechanism has a lower net energy barrier than that in the newly deduced mechanism, and thus should be more preferred. The mechanism indicates that DMDFC is first protonized, followed by a proton shift process, and thereafter an OH(-) ion is added, completing the hydration process. Thereafter, an intramolecular H-shift reaction proceeds, leading to conversion to the intended intermediate product DOHE by the consecutive processes of isomerization and dehydration.; A reaction route accounting for the formation of levulinic acid from 5-hydroxymethylfuran-2-carbaldehyde was deduced on the basis of the mechanism previously offered by Horvat, to match the steps with more details. A newly deduced reaction route was proposed between two intermediate products within this mechanism, and the probabilities of the two mechanisms were compared by Gaussian 03 software. It was found that the conversion from the intermediate 2,3-dihydroxy-5-methyl-2,3-dihydro-furan-2-carbaldehyde (DMDFC) to 2,5-dioxo-hex-3-enal (DOHE) in the original mechanism has a lower net energy barrier than that in the newly deduced mechanism, and thus should be more preferred. The mechanism indicates that DMDFC is first protonized, followed by a proton shift process, and thereafter an OH(-) ion is added, completing the hydration process. Thereafter, an intramolecular H-shift reaction proceeds, leading to conversion to the intended intermediate product DOHE by the consecutive processes of isomerization and dehydration.
KeywordLevulinic Acid Mechanism Transition State
SubtypeArticle
WOS HeadingsScience & Technology ; Technology
URL查看原文
Indexed BySCI
Language英语
WOS KeywordEFFICIENT ; GLUCOSE
WOS Research AreaMaterials Science
WOS SubjectMaterials Science, Paper & Wood
WOS IDWOS:000291559600071
Citation statistics
Cited Times:2[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Version出版稿
Identifierhttp://ir.ipe.ac.cn/handle/122111/6389
Collection研究所(批量导入)
AffiliationChinese Acad Sci, Inst Proc Engn, State Key Lab Multiphase Complex Syst, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Wang, Ze,Lin, Weigang,Song, Wenli. MECHANISTIC STUDY OF THE CONVERSION FROM DMDFC TO DOHE IN THE LEVULINIC ACID FORMATION PROCESS BY THEORETICAL APPROACHES[J]. BIORESOURCES,2011,6(2):1858-1867.
APA Wang, Ze,Lin, Weigang,&Song, Wenli.(2011).MECHANISTIC STUDY OF THE CONVERSION FROM DMDFC TO DOHE IN THE LEVULINIC ACID FORMATION PROCESS BY THEORETICAL APPROACHES.BIORESOURCES,6(2),1858-1867.
MLA Wang, Ze,et al."MECHANISTIC STUDY OF THE CONVERSION FROM DMDFC TO DOHE IN THE LEVULINIC ACID FORMATION PROCESS BY THEORETICAL APPROACHES".BIORESOURCES 6.2(2011):1858-1867.
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