Effective conversion of fructose to 5-ethoxymethylfurfural with brønsted acid site (S/Cl)-functional carbon catalysts
Brønsted acid site (S/Cl)-functional carbon materials were prepared by ball-milling (bm) L-cysteine and ammonium chloride to form chemical complex solids, by post-heat treatment (Q) of the solids at 500 °C under a nitrogen gas atmosphere to stabilize and fortify amino and functional group solid stru...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co., Ltd.
2022-02-01
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| Series: | Journal of Bioresources and Bioproducts |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2369969821000815 |
| _version_ | 1827980722392006656 |
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| author | Haixin Guo Ryota Higashiguchi Yuya Abe Richard Lee Smith |
| author_facet | Haixin Guo Ryota Higashiguchi Yuya Abe Richard Lee Smith |
| author_sort | Haixin Guo |
| collection | DOAJ |
| description | Brønsted acid site (S/Cl)-functional carbon materials were prepared by ball-milling (bm) L-cysteine and ammonium chloride to form chemical complex solids, by post-heat treatment (Q) of the solids at 500 °C under a nitrogen gas atmosphere to stabilize and fortify amino and functional group solid structures and by post-oxidative treatment with H2O2 to add Brønsted acidity. The as-prepared carbon materials (S/Cl@bmxQy; x, y in hours) contained Brønsted acid sites (sulfonates, chlorides), oxygen-containing groups (-COOH, -OH) and amino functional groups. The S/Cl@bmxQy materials were applied as catalysts to promote conversion of fructose in ethanol solvent to 5-hydroxymethylfurfural (5-HMF) and 5-ethoxymethylfurfural (5-EMF). Among the carbon materials, S/Cl@bm3Q1 gave 5-EMF and 5-HMF yields of 67.0% and 22.8%, respectively, in pure ethanol at 140 °C for 24 h reaction time, while a reaction time of 18 h gave total 5-EMF and 5-HMF yields of 96.4%. Dimethyl sulfoxide (DMSO) was applied as additive to the ethanol-fructose- S/Cl@bm3Q1 reaction system which showed that 5-HMF product selectivity could be controlled with DMSO concentration. The protocol developed allows simple preparation of functional carbon materials that have high catalytic activity and are effective for conversion of fructose to 5-HMF and 5-EMF in ethanol. |
| first_indexed | 2024-04-09T21:57:48Z |
| format | Article |
| id | doaj.art-b9ac45af6aec4c088907c220a6d60d5b |
| institution | Directory Open Access Journal |
| issn | 2369-9698 |
| language | English |
| last_indexed | 2024-04-09T21:57:48Z |
| publishDate | 2022-02-01 |
| publisher | KeAi Communications Co., Ltd. |
| record_format | Article |
| series | Journal of Bioresources and Bioproducts |
| spelling | doaj.art-b9ac45af6aec4c088907c220a6d60d5b2023-03-24T04:22:42ZengKeAi Communications Co., Ltd.Journal of Bioresources and Bioproducts2369-96982022-02-01713342Effective conversion of fructose to 5-ethoxymethylfurfural with brønsted acid site (S/Cl)-functional carbon catalystsHaixin Guo0Ryota Higashiguchi1Yuya Abe2Richard Lee Smith3Graduate School of Environmental Studies, Tohoku University, Aramaki Aza Aoba 6-6-11, Aoba, Sendai 980-8579, Japan; Corresponding authors. Graduate School of Environmental Studies, Tohoku University, Aramaki Aza Aoba 6-6-11, Aoba, Sendai 980-8579, Japan; Research Center of Supercritical Fluid Technology, Tohoku University, Aramaki Aza Aoba 6-6-11, Aoba-ku, Sendai 980-8579, JapanGraduate School of Environmental Studies, Tohoku University, Aramaki Aza Aoba 6-6-11, Aoba, Sendai 980-8579, JapanGraduate School of Environmental Studies, Tohoku University, Aramaki Aza Aoba 6-6-11, Aoba, Sendai 980-8579, JapanGraduate School of Environmental Studies, Tohoku University, Aramaki Aza Aoba 6-6-11, Aoba, Sendai 980-8579, Japan; Research Center of Supercritical Fluid Technology, Tohoku University, Aramaki Aza Aoba 6-6-11, Aoba-ku, Sendai 980-8579, Japan; Corresponding authors. Graduate School of Environmental Studies, Tohoku University, Aramaki Aza Aoba 6-6-11, Aoba, Sendai 980-8579, Japan; Research Center of Supercritical Fluid Technology, Tohoku University, Aramaki Aza Aoba 6-6-11, Aoba-ku, Sendai 980-8579, JapanBrønsted acid site (S/Cl)-functional carbon materials were prepared by ball-milling (bm) L-cysteine and ammonium chloride to form chemical complex solids, by post-heat treatment (Q) of the solids at 500 °C under a nitrogen gas atmosphere to stabilize and fortify amino and functional group solid structures and by post-oxidative treatment with H2O2 to add Brønsted acidity. The as-prepared carbon materials (S/Cl@bmxQy; x, y in hours) contained Brønsted acid sites (sulfonates, chlorides), oxygen-containing groups (-COOH, -OH) and amino functional groups. The S/Cl@bmxQy materials were applied as catalysts to promote conversion of fructose in ethanol solvent to 5-hydroxymethylfurfural (5-HMF) and 5-ethoxymethylfurfural (5-EMF). Among the carbon materials, S/Cl@bm3Q1 gave 5-EMF and 5-HMF yields of 67.0% and 22.8%, respectively, in pure ethanol at 140 °C for 24 h reaction time, while a reaction time of 18 h gave total 5-EMF and 5-HMF yields of 96.4%. Dimethyl sulfoxide (DMSO) was applied as additive to the ethanol-fructose- S/Cl@bm3Q1 reaction system which showed that 5-HMF product selectivity could be controlled with DMSO concentration. The protocol developed allows simple preparation of functional carbon materials that have high catalytic activity and are effective for conversion of fructose to 5-HMF and 5-EMF in ethanol.http://www.sciencedirect.com/science/article/pii/S2369969821000815Ball-millingEtherificationFuel additiveEthanolBrønsted acid |
| spellingShingle | Haixin Guo Ryota Higashiguchi Yuya Abe Richard Lee Smith Effective conversion of fructose to 5-ethoxymethylfurfural with brønsted acid site (S/Cl)-functional carbon catalysts Journal of Bioresources and Bioproducts Ball-milling Etherification Fuel additive Ethanol Brønsted acid |
| title | Effective conversion of fructose to 5-ethoxymethylfurfural with brønsted acid site (S/Cl)-functional carbon catalysts |
| title_full | Effective conversion of fructose to 5-ethoxymethylfurfural with brønsted acid site (S/Cl)-functional carbon catalysts |
| title_fullStr | Effective conversion of fructose to 5-ethoxymethylfurfural with brønsted acid site (S/Cl)-functional carbon catalysts |
| title_full_unstemmed | Effective conversion of fructose to 5-ethoxymethylfurfural with brønsted acid site (S/Cl)-functional carbon catalysts |
| title_short | Effective conversion of fructose to 5-ethoxymethylfurfural with brønsted acid site (S/Cl)-functional carbon catalysts |
| title_sort | effective conversion of fructose to 5 ethoxymethylfurfural with bronsted acid site s cl functional carbon catalysts |
| topic | Ball-milling Etherification Fuel additive Ethanol Brønsted acid |
| url | http://www.sciencedirect.com/science/article/pii/S2369969821000815 |
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