Reactivity studies in water on the acid-catalysed dehydration of psicose compared to other ketohexoses into 5-hydroxymethylfurfural

The conversion of the four possible ketohexoses (fructose, tagatose, sorbose and psicose) into 5-hydroxymethylfurfural (HMF) was explored in water using sulphuric acid as the catalyst (33 mM H2SO4, 120 °C). Significant differences in reactivity were observed and tagatose (48% conversion after 75 min...

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Vydáno v:	Carbohydrate research Ročník 446-447; s. 1 - 6
Hlavní autoři:	van Putten, Robert-Jan, van der Waal, Jan C., de Jong, Ed, Heeres, Hero J.
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	Netherlands Elsevier Ltd 29.06.2017
Témata:	5-Hydroxymethylfurfural Catalysis catalysts fructose Fructose - chemistry Furaldehyde - analogs & derivatives Furaldehyde - chemistry Hydrogen-Ion Concentration hydroxymethylfurfural Ketose methanol Methanol - chemistry Psicose sorbose Sugar dehydration sulfuric acid tagatose Water - chemistry Sugar dehydration Psicose 5-Hydroxymethylfurfural Ketose
ISSN:	0008-6215, 1873-426X, 1873-426X
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Abstract	The conversion of the four possible ketohexoses (fructose, tagatose, sorbose and psicose) into 5-hydroxymethylfurfural (HMF) was explored in water using sulphuric acid as the catalyst (33 mM H2SO4, 120 °C). Significant differences in reactivity were observed and tagatose (48% conversion after 75 min) and psicose (35% conversion after 75 min) were clearly more reactive than fructose and sorbose (around 20% conversion after 75 min). The selectivity to HMF was found to be higher for fructose and psicose than for tagatose and sorbose. 2-Hydroxyacetylfuran (HAF) was shown to be a by-product for mainly sorbose and tagatose (as high as 2% yield). The results indicate that the relative orientation of the hydroxyl groups on C3 and C4 has a major effect on the reactivity and selectivity. This suggests that the dehydration towards HMF takes place via a mechanism with cyclic intermediates in which the C3C4 bond is fixed in a ring structure. A reaction mechanism involving a bicyclic structure is proposed to explain the formation of HAF. The reactivity of the sugars was significantly lower in water than previously observed in methanol. [Display omitted] •Hydroxyl group orientation on C3 and C4 determines ketose reactivity in dehydration.•This suggests a reaction mechanism with cyclic intermediates.•Psicose would be the most favourable substrate for HMF production.•The orientation of the C4 hydroxyl is key in 2-hydroxyacetylfuran formation.•The reactivity of psicose and tagatose affects their application as sweeteners.
AbstractList	The conversion of the four possible ketohexoses (fructose, tagatose, sorbose and psicose) into 5-hydroxymethylfurfural (HMF) was explored in water using sulphuric acid as the catalyst (33 mM H2SO4, 120 °C). Significant differences in reactivity were observed and tagatose (48% conversion after 75 min) and psicose (35% conversion after 75 min) were clearly more reactive than fructose and sorbose (around 20% conversion after 75 min). The selectivity to HMF was found to be higher for fructose and psicose than for tagatose and sorbose. 2-Hydroxyacetylfuran (HAF) was shown to be a by-product for mainly sorbose and tagatose (as high as 2% yield). The results indicate that the relative orientation of the hydroxyl groups on C3 and C4 has a major effect on the reactivity and selectivity. This suggests that the dehydration towards HMF takes place via a mechanism with cyclic intermediates in which the C3C4 bond is fixed in a ring structure. A reaction mechanism involving a bicyclic structure is proposed to explain the formation of HAF. The reactivity of the sugars was significantly lower in water than previously observed in methanol. [Display omitted] •Hydroxyl group orientation on C3 and C4 determines ketose reactivity in dehydration.•This suggests a reaction mechanism with cyclic intermediates.•Psicose would be the most favourable substrate for HMF production.•The orientation of the C4 hydroxyl is key in 2-hydroxyacetylfuran formation.•The reactivity of psicose and tagatose affects their application as sweeteners. The conversion of the four possible ketohexoses (fructose, tagatose, sorbose and psicose) into 5-hydroxymethylfurfural (HMF) was explored in water using sulphuric acid as the catalyst (33 mM H2SO4, 120 °C). Significant differences in reactivity were observed and tagatose (48% conversion after 75 min) and psicose (35% conversion after 75 min) were clearly more reactive than fructose and sorbose (around 20% conversion after 75 min). The selectivity to HMF was found to be higher for fructose and psicose than for tagatose and sorbose. 2-Hydroxyacetylfuran (HAF) was shown to be a by-product for mainly sorbose and tagatose (as high as 2% yield). The results indicate that the relative orientation of the hydroxyl groups on C3 and C4 has a major effect on the reactivity and selectivity. This suggests that the dehydration towards HMF takes place via a mechanism with cyclic intermediates in which the C3C4 bond is fixed in a ring structure. A reaction mechanism involving a bicyclic structure is proposed to explain the formation of HAF. The reactivity of the sugars was significantly lower in water than previously observed in methanol.The conversion of the four possible ketohexoses (fructose, tagatose, sorbose and psicose) into 5-hydroxymethylfurfural (HMF) was explored in water using sulphuric acid as the catalyst (33 mM H2SO4, 120 °C). Significant differences in reactivity were observed and tagatose (48% conversion after 75 min) and psicose (35% conversion after 75 min) were clearly more reactive than fructose and sorbose (around 20% conversion after 75 min). The selectivity to HMF was found to be higher for fructose and psicose than for tagatose and sorbose. 2-Hydroxyacetylfuran (HAF) was shown to be a by-product for mainly sorbose and tagatose (as high as 2% yield). The results indicate that the relative orientation of the hydroxyl groups on C3 and C4 has a major effect on the reactivity and selectivity. This suggests that the dehydration towards HMF takes place via a mechanism with cyclic intermediates in which the C3C4 bond is fixed in a ring structure. A reaction mechanism involving a bicyclic structure is proposed to explain the formation of HAF. The reactivity of the sugars was significantly lower in water than previously observed in methanol. The conversion of the four possible ketohexoses (fructose, tagatose, sorbose and psicose) into 5-hydroxymethylfurfural (HMF) was explored in water using sulphuric acid as the catalyst (33 mM H2SO4, 120 °C). Significant differences in reactivity were observed and tagatose (48% conversion after 75 min) and psicose (35% conversion after 75 min) were clearly more reactive than fructose and sorbose (around 20% conversion after 75 min). The selectivity to HMF was found to be higher for fructose and psicose than for tagatose and sorbose. 2-Hydroxyacetylfuran (HAF) was shown to be a by-product for mainly sorbose and tagatose (as high as 2% yield). The results indicate that the relative orientation of the hydroxyl groups on C3 and C4 has a major effect on the reactivity and selectivity. This suggests that the dehydration towards HMF takes place via a mechanism with cyclic intermediates in which the C3-C4 bond is fixed in a ring structure. A reaction mechanism involving a bicyclic structure is proposed to explain the formation of HAF. The reactivity of the sugars was significantly lower in water than previously observed in methanol. The conversion of the four possible ketohexoses (fructose, tagatose, sorbose and psicose) into 5-hydroxymethylfurfural (HMF) was explored in water using sulphuric acid as the catalyst (33 mM H SO , 120 °C). Significant differences in reactivity were observed and tagatose (48% conversion after 75 min) and psicose (35% conversion after 75 min) were clearly more reactive than fructose and sorbose (around 20% conversion after 75 min). The selectivity to HMF was found to be higher for fructose and psicose than for tagatose and sorbose. 2-Hydroxyacetylfuran (HAF) was shown to be a by-product for mainly sorbose and tagatose (as high as 2% yield). The results indicate that the relative orientation of the hydroxyl groups on C3 and C4 has a major effect on the reactivity and selectivity. This suggests that the dehydration towards HMF takes place via a mechanism with cyclic intermediates in which the C3C4 bond is fixed in a ring structure. A reaction mechanism involving a bicyclic structure is proposed to explain the formation of HAF. The reactivity of the sugars was significantly lower in water than previously observed in methanol.
Author	de Jong, Ed Heeres, Hero J. van der Waal, Jan C. van Putten, Robert-Jan
Author_xml	– sequence: 1 givenname: Robert-Jan orcidid: 0000-0003-1021-577X surname: van Putten fullname: van Putten, Robert-Jan email: robert-jan.vanputten@avantium.com organization: Avantium Chemicals B.V., Zekeringstraat 29, 1014 BV Amsterdam, The Netherlands – sequence: 2 givenname: Jan C. orcidid: 0000-0002-9830-6109 surname: van der Waal fullname: van der Waal, Jan C. organization: Avantium Chemicals B.V., Zekeringstraat 29, 1014 BV Amsterdam, The Netherlands – sequence: 3 givenname: Ed orcidid: 0000-0001-5300-4230 surname: de Jong fullname: de Jong, Ed organization: Avantium Chemicals B.V., Zekeringstraat 29, 1014 BV Amsterdam, The Netherlands – sequence: 4 givenname: Hero J. surname: Heeres fullname: Heeres, Hero J. email: h.j.heeres@rug.nl organization: Department of Chemical Engineering, ENTEG, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
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Cites_doi	10.1002/bbb.1360 10.1039/c2ee02480b 10.1205/cherd05038 10.1021/ja00403a051 10.1002/macp.201400316 10.1002/mame.201400376 10.1021/cr300182k 10.1002/cssc.201600252 10.1016/j.cej.2016.04.039 10.1016/S0040-4039(01)94436-3 10.1021/ja01140a528 10.1016/0009-8981(73)90315-X 10.1039/b518176c 10.1039/b923961h 10.1002/cssc.201300345 10.1021/ma5000199 10.1021/bk-2012-1105.ch001 10.1016/j.catcom.2015.05.024 10.1039/b922014c 10.1002/cssc.201300332 10.1021/ie061186z 10.1002/jlac.19707330117
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Snippet	The conversion of the four possible ketohexoses (fructose, tagatose, sorbose and psicose) into 5-hydroxymethylfurfural (HMF) was explored in water using...
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SubjectTerms	5-Hydroxymethylfurfural Catalysis catalysts fructose Fructose - chemistry Furaldehyde - analogs & derivatives Furaldehyde - chemistry Hydrogen-Ion Concentration hydroxymethylfurfural Ketose methanol Methanol - chemistry Psicose sorbose Sugar dehydration sulfuric acid tagatose Water - chemistry
Title	Reactivity studies in water on the acid-catalysed dehydration of psicose compared to other ketohexoses into 5-hydroxymethylfurfural
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