Sn-Beta catalysed conversion of hemicellulosic sugars

Martin Holm; Yomaira J. Pagán-Torres; Saravanamurugan Shunmugavel; Anders Riisager; James A. Dumesic; Esben Taarning

doi:10.1039/c2gc16202d

Sn-Beta catalysed conversion of hemicellulosic sugars

Martin Holm, Yomaira J. Pagán-Torres, Saravanamurugan Shunmugavel, Anders Riisager, James A. Dumesic, Esben Taarning

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

Conversions of various pentoses and hexoses into methyl lactate has been demonstrated for the Sn-Beta catalyst. It is found that pentoses are converted to methyl lactate in slightly lower yields (∼40%) than what is obtained for hexoses (∼50%), but higher yields of glycolaldehyde dimethyl acetal are observed for the pentoses. This finding is in accordance to a reaction pathway that involves the retro aldol condensation of the sugars to form a triose and glycolaldehyde for the pentoses, and two trioses for hexoses. When reacting glycolaldehyde (formally a C2-sugar) in the presence of Sn-Beta, aldol condensation occurs, leading to the formation of methyl lactate, methyl vinylglycolate and methyl 2-hydroxy-4-methoxybutanoate. In contrast, when converting the sugars in water at low temperatures (100 °C), Sn-Beta catalyses the isomerisation of sugars (ketose–aldose epimers), rather than the formation of lactates.

Original language	English
Journal	Green Chemistry
Volume	14
Pages (from-to)	702-706
ISSN	1463-9262
DOIs	https://doi.org/10.1039/c2gc16202d
Publication status	Published - 2012

Bibliographical note

Electronic supplementary information (ESI) available: Detailed HPLC
analysis procedure, sugar isomerization distributions, carbon balances,
NMR spectra and MS fragmentation patterns of key components. See
DOI: 10.1039/c2gc16202d

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title = "Sn-Beta catalysed conversion of hemicellulosic sugars",

abstract = "Conversions of various pentoses and hexoses into methyl lactate has been demonstrated for the Sn-Beta catalyst. It is found that pentoses are converted to methyl lactate in slightly lower yields (∼40%) than what is obtained for hexoses (∼50%), but higher yields of glycolaldehyde dimethyl acetal are observed for the pentoses. This finding is in accordance to a reaction pathway that involves the retro aldol condensation of the sugars to form a triose and glycolaldehyde for the pentoses, and two trioses for hexoses. When reacting glycolaldehyde (formally a C2-sugar) in the presence of Sn-Beta, aldol condensation occurs, leading to the formation of methyl lactate, methyl vinylglycolate and methyl 2-hydroxy-4-methoxybutanoate. In contrast, when converting the sugars in water at low temperatures (100 °C), Sn-Beta catalyses the isomerisation of sugars (ketose–aldose epimers), rather than the formation of lactates.",

author = "Martin Holm and Pag{\'a}n-Torres, {Yomaira J.} and Saravanamurugan Shunmugavel and Anders Riisager and Dumesic, {James A.} and Esben Taarning",

note = "Electronic supplementary information (ESI) available: Detailed HPLC analysis procedure, sugar isomerization distributions, carbon balances, NMR spectra and MS fragmentation patterns of key components. See DOI: 10.1039/c2gc16202d",

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T1 - Sn-Beta catalysed conversion of hemicellulosic sugars

AU - Holm, Martin

AU - Pagán-Torres, Yomaira J.

AU - Shunmugavel, Saravanamurugan

AU - Riisager, Anders

AU - Dumesic, James A.

AU - Taarning, Esben

N1 - Electronic supplementary information (ESI) available: Detailed HPLC analysis procedure, sugar isomerization distributions, carbon balances, NMR spectra and MS fragmentation patterns of key components. See DOI: 10.1039/c2gc16202d

PY - 2012

Y1 - 2012

N2 - Conversions of various pentoses and hexoses into methyl lactate has been demonstrated for the Sn-Beta catalyst. It is found that pentoses are converted to methyl lactate in slightly lower yields (∼40%) than what is obtained for hexoses (∼50%), but higher yields of glycolaldehyde dimethyl acetal are observed for the pentoses. This finding is in accordance to a reaction pathway that involves the retro aldol condensation of the sugars to form a triose and glycolaldehyde for the pentoses, and two trioses for hexoses. When reacting glycolaldehyde (formally a C2-sugar) in the presence of Sn-Beta, aldol condensation occurs, leading to the formation of methyl lactate, methyl vinylglycolate and methyl 2-hydroxy-4-methoxybutanoate. In contrast, when converting the sugars in water at low temperatures (100 °C), Sn-Beta catalyses the isomerisation of sugars (ketose–aldose epimers), rather than the formation of lactates.

AB - Conversions of various pentoses and hexoses into methyl lactate has been demonstrated for the Sn-Beta catalyst. It is found that pentoses are converted to methyl lactate in slightly lower yields (∼40%) than what is obtained for hexoses (∼50%), but higher yields of glycolaldehyde dimethyl acetal are observed for the pentoses. This finding is in accordance to a reaction pathway that involves the retro aldol condensation of the sugars to form a triose and glycolaldehyde for the pentoses, and two trioses for hexoses. When reacting glycolaldehyde (formally a C2-sugar) in the presence of Sn-Beta, aldol condensation occurs, leading to the formation of methyl lactate, methyl vinylglycolate and methyl 2-hydroxy-4-methoxybutanoate. In contrast, when converting the sugars in water at low temperatures (100 °C), Sn-Beta catalyses the isomerisation of sugars (ketose–aldose epimers), rather than the formation of lactates.

U2 - 10.1039/c2gc16202d

DO - 10.1039/c2gc16202d

M3 - Journal article

SN - 1463-9262

VL - 14

SP - 702

EP - 706

JO - Green Chemistry

JF - Green Chemistry

ER -

Sn-Beta catalysed conversion of hemicellulosic sugars

Abstract

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