Reactions of d-fructose in water at temperatures up to 400 °C and pressures up to 100 MPa

Taku Michael Aida; Kiyohiko Tajima; Masaru Watanabe; Yuki Saito; Kiyoshi Kuroda; Toshiyuki Nonaka; Hideo Hattori; Richard Lee Smith; Kunio Arai

doi:10.1016/j.supflu.2006.12.017

Reactions of d-fructose in water at temperatures up to 400 °C and pressures up to 100 MPa

Taku Michael Aida, Kiyohiko Tajima, Masaru Watanabe, Yuki Saito, Kiyoshi Kuroda, Toshiyuki Nonaka, Hideo Hattori, Richard Lee Smith, Kunio Arai

ENG - Research Center of Supercritical Fluid Terchnolody

Research output: Contribution to journal › Article › peer-review

149 Citations (Scopus)

Abstract

Reactions of d-fructose in water at high temperatures (350 and 400 °C) and pressures (up to 100 MPa) were studied using a flow reactor. High temperature (400 °C) and moderate pressure (40 MPa) conditions enhanced the yields of retro-aldol related products such as glyceraldehyde, dihydroxyacetone and pyruvaldehyde. High temperature, high pressure conditions enhanced retro-aldol reactions and water related reactions such as hydrolysis and dehydration. Comparison between d-fructose and d-glucose experiments showed that higher yields for 5-HMF were obtained starting from d-fructose than d-glucose. Surprisingly, higher yields of furfural were obtained starting from d-glucose than from d-fructose which is contrary to reaction pathways in the hydrothermal literature. Based on the experimental results, a possible reaction scheme is proposed for water catalyzed (i) benzilic acid rearrangement reactions from pyruvaldehyde to lactic acid and (ii) retro-aldol reaction from d-glucose to furfural.

Original language	English
Pages (from-to)	110-119
Number of pages	10
Journal	Journal of Supercritical Fluids
Volume	42
Issue number	1
DOIs	https://doi.org/10.1016/j.supflu.2006.12.017
Publication status	Published - 2007 Aug

Keywords

5-HMF
Biomass
d-Fructose
Furfural
High temperature water
Lactic acid

Access to Document

10.1016/j.supflu.2006.12.017

Cite this

@article{449639a83f774e5d8cc170d40c81e056,

title = "Reactions of d-fructose in water at temperatures up to 400 °C and pressures up to 100 MPa",

abstract = "Reactions of d-fructose in water at high temperatures (350 and 400 °C) and pressures (up to 100 MPa) were studied using a flow reactor. High temperature (400 °C) and moderate pressure (40 MPa) conditions enhanced the yields of retro-aldol related products such as glyceraldehyde, dihydroxyacetone and pyruvaldehyde. High temperature, high pressure conditions enhanced retro-aldol reactions and water related reactions such as hydrolysis and dehydration. Comparison between d-fructose and d-glucose experiments showed that higher yields for 5-HMF were obtained starting from d-fructose than d-glucose. Surprisingly, higher yields of furfural were obtained starting from d-glucose than from d-fructose which is contrary to reaction pathways in the hydrothermal literature. Based on the experimental results, a possible reaction scheme is proposed for water catalyzed (i) benzilic acid rearrangement reactions from pyruvaldehyde to lactic acid and (ii) retro-aldol reaction from d-glucose to furfural.",

keywords = "5-HMF, Biomass, d-Fructose, Furfural, High temperature water, Lactic acid",

author = "Aida, {Taku Michael} and Kiyohiko Tajima and Masaru Watanabe and Yuki Saito and Kiyoshi Kuroda and Toshiyuki Nonaka and Hideo Hattori and Smith, {Richard Lee} and Kunio Arai",

year = "2007",

month = aug,

doi = "10.1016/j.supflu.2006.12.017",

language = "English",

volume = "42",

pages = "110--119",

journal = "Journal of Supercritical Fluids",

issn = "0896-8446",

publisher = "Elsevier",

number = "1",

}

TY - JOUR

T1 - Reactions of d-fructose in water at temperatures up to 400 °C and pressures up to 100 MPa

AU - Aida, Taku Michael

AU - Tajima, Kiyohiko

AU - Watanabe, Masaru

AU - Saito, Yuki

AU - Kuroda, Kiyoshi

AU - Nonaka, Toshiyuki

AU - Hattori, Hideo

AU - Smith, Richard Lee

AU - Arai, Kunio

PY - 2007/8

Y1 - 2007/8

N2 - Reactions of d-fructose in water at high temperatures (350 and 400 °C) and pressures (up to 100 MPa) were studied using a flow reactor. High temperature (400 °C) and moderate pressure (40 MPa) conditions enhanced the yields of retro-aldol related products such as glyceraldehyde, dihydroxyacetone and pyruvaldehyde. High temperature, high pressure conditions enhanced retro-aldol reactions and water related reactions such as hydrolysis and dehydration. Comparison between d-fructose and d-glucose experiments showed that higher yields for 5-HMF were obtained starting from d-fructose than d-glucose. Surprisingly, higher yields of furfural were obtained starting from d-glucose than from d-fructose which is contrary to reaction pathways in the hydrothermal literature. Based on the experimental results, a possible reaction scheme is proposed for water catalyzed (i) benzilic acid rearrangement reactions from pyruvaldehyde to lactic acid and (ii) retro-aldol reaction from d-glucose to furfural.

AB - Reactions of d-fructose in water at high temperatures (350 and 400 °C) and pressures (up to 100 MPa) were studied using a flow reactor. High temperature (400 °C) and moderate pressure (40 MPa) conditions enhanced the yields of retro-aldol related products such as glyceraldehyde, dihydroxyacetone and pyruvaldehyde. High temperature, high pressure conditions enhanced retro-aldol reactions and water related reactions such as hydrolysis and dehydration. Comparison between d-fructose and d-glucose experiments showed that higher yields for 5-HMF were obtained starting from d-fructose than d-glucose. Surprisingly, higher yields of furfural were obtained starting from d-glucose than from d-fructose which is contrary to reaction pathways in the hydrothermal literature. Based on the experimental results, a possible reaction scheme is proposed for water catalyzed (i) benzilic acid rearrangement reactions from pyruvaldehyde to lactic acid and (ii) retro-aldol reaction from d-glucose to furfural.

KW - 5-HMF

KW - Biomass

KW - d-Fructose

KW - Furfural

KW - High temperature water

KW - Lactic acid

UR - http://www.scopus.com/inward/record.url?scp=34248637000&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34248637000&partnerID=8YFLogxK

U2 - 10.1016/j.supflu.2006.12.017

DO - 10.1016/j.supflu.2006.12.017

M3 - Article

AN - SCOPUS:34248637000

SN - 0896-8446

VL - 42

SP - 110

EP - 119

JO - Journal of Supercritical Fluids

JF - Journal of Supercritical Fluids

IS - 1

ER -

Reactions of d-fructose in water at temperatures up to 400 °C and pressures up to 100 MPa

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this