Wei Qi, Yuqi Chen, Liangzhi Li, Xin Ju, Hongwei Chen and Lishi Yan
{"title":"温和条件下三元深共晶溶剂双相体系中果糖转化为5-羟甲基糠醛的研究","authors":"Wei Qi, Yuqi Chen, Liangzhi Li, Xin Ju, Hongwei Chen and Lishi Yan","doi":"10.1039/D5RE00057B","DOIUrl":null,"url":null,"abstract":"<p >The catalytic conversion of fructose to 5-hydroxymethylfurfural (5-HMF) in a ternary deep eutectic solvent (DES)/methyl isobutyl ketone (MIBK) biphasic system at mild temperatures (50–70 °C) was investigated in this work. The ternary DES consisting of choline chloride (ChCl), benzene sulfonic acid (BSA) and ethylene glycol (EG) was physicochemically characterized by FT-IR and <small><sup>1</sup></small>H NMR. The ternary DES(ChCl–BSA–EG)/MIBK biphasic system (ChCl/BSA/EG = 2 : 1 : 1) resulted in an 82.0% 5-HMF yield and 96.2% corresponding selectivity at 60 °C for 2 h. The kinetic analysis further revealed that the rate constant of fructose dehydration (<em>k</em><small><sub>1</sub></small>) was much higher than the rate constant of 5-HMF conversion (<em>k</em><small><sub>2</sub></small>). The calculated ratio of <em>k</em><small><sub>1</sub></small>/<em>k</em><small><sub>2</sub></small> was 16.1. The proposed reaction mechanism suggested that the synergetic effect of the three components of the ternary DES facilitates the elimination of water molecules from fructose and the formation of 5-HMF, while the MIBK extraction phase suppresses the by-products of 5-HMF as well. The present work provides a green and sustainable pathway for 5-HMF production with a high yield and high selectivity at mild temperatures.</p>","PeriodicalId":101,"journal":{"name":"Reaction Chemistry & Engineering","volume":" 7","pages":" 1587-1595"},"PeriodicalIF":3.1000,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Conversion of fructose to 5-hydroxymethylfurfural in a ternary deep eutectic solvent-based biphasic system at mild temperature\",\"authors\":\"Wei Qi, Yuqi Chen, Liangzhi Li, Xin Ju, Hongwei Chen and Lishi Yan\",\"doi\":\"10.1039/D5RE00057B\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >The catalytic conversion of fructose to 5-hydroxymethylfurfural (5-HMF) in a ternary deep eutectic solvent (DES)/methyl isobutyl ketone (MIBK) biphasic system at mild temperatures (50–70 °C) was investigated in this work. The ternary DES consisting of choline chloride (ChCl), benzene sulfonic acid (BSA) and ethylene glycol (EG) was physicochemically characterized by FT-IR and <small><sup>1</sup></small>H NMR. The ternary DES(ChCl–BSA–EG)/MIBK biphasic system (ChCl/BSA/EG = 2 : 1 : 1) resulted in an 82.0% 5-HMF yield and 96.2% corresponding selectivity at 60 °C for 2 h. The kinetic analysis further revealed that the rate constant of fructose dehydration (<em>k</em><small><sub>1</sub></small>) was much higher than the rate constant of 5-HMF conversion (<em>k</em><small><sub>2</sub></small>). The calculated ratio of <em>k</em><small><sub>1</sub></small>/<em>k</em><small><sub>2</sub></small> was 16.1. The proposed reaction mechanism suggested that the synergetic effect of the three components of the ternary DES facilitates the elimination of water molecules from fructose and the formation of 5-HMF, while the MIBK extraction phase suppresses the by-products of 5-HMF as well. The present work provides a green and sustainable pathway for 5-HMF production with a high yield and high selectivity at mild temperatures.</p>\",\"PeriodicalId\":101,\"journal\":{\"name\":\"Reaction Chemistry & Engineering\",\"volume\":\" 7\",\"pages\":\" 1587-1595\"},\"PeriodicalIF\":3.1000,\"publicationDate\":\"2025-04-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Reaction Chemistry & Engineering\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2025/re/d5re00057b\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Reaction Chemistry & Engineering","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/re/d5re00057b","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Conversion of fructose to 5-hydroxymethylfurfural in a ternary deep eutectic solvent-based biphasic system at mild temperature
The catalytic conversion of fructose to 5-hydroxymethylfurfural (5-HMF) in a ternary deep eutectic solvent (DES)/methyl isobutyl ketone (MIBK) biphasic system at mild temperatures (50–70 °C) was investigated in this work. The ternary DES consisting of choline chloride (ChCl), benzene sulfonic acid (BSA) and ethylene glycol (EG) was physicochemically characterized by FT-IR and 1H NMR. The ternary DES(ChCl–BSA–EG)/MIBK biphasic system (ChCl/BSA/EG = 2 : 1 : 1) resulted in an 82.0% 5-HMF yield and 96.2% corresponding selectivity at 60 °C for 2 h. The kinetic analysis further revealed that the rate constant of fructose dehydration (k1) was much higher than the rate constant of 5-HMF conversion (k2). The calculated ratio of k1/k2 was 16.1. The proposed reaction mechanism suggested that the synergetic effect of the three components of the ternary DES facilitates the elimination of water molecules from fructose and the formation of 5-HMF, while the MIBK extraction phase suppresses the by-products of 5-HMF as well. The present work provides a green and sustainable pathway for 5-HMF production with a high yield and high selectivity at mild temperatures.
期刊介绍:
Reaction Chemistry & Engineering is a new journal reporting cutting edge research into all aspects of making molecules for the benefit of fundamental research, applied processes and wider society.
From fundamental, molecular-level chemistry to large scale chemical production, Reaction Chemistry & Engineering brings together communities of chemists and chemical engineers working to ensure the crucial role of reaction chemistry in today’s world.