Yuan Xiao , Yuhong Ma , Kaizhuo Lv , Qiuli Yao , Jingtao Liu , Shuguang Xu
{"title":"不同种类SnCl4(aq)对浒苔鼠李糖转化为5-甲基糠醛的协同催化作用","authors":"Yuan Xiao , Yuhong Ma , Kaizhuo Lv , Qiuli Yao , Jingtao Liu , Shuguang Xu","doi":"10.1016/j.indcrop.2025.120661","DOIUrl":null,"url":null,"abstract":"<div><div>The growing demand for 5-methylfurfural (5-MF) across various applications has driven the pursuit of environmentally friendly production methods. Herein, we proposed a facile and highly efficient method for converting <em>Enteromorpha prolifera</em>-derived rhamnose into 5-methylfurfural (5-MF) in H<sub>2</sub>O/MIBK media using metal chloride salts as catalysts. SnCl<sub>4</sub> was capable of achieving a high 5-MF yield of 68.8 % under optimized conditions. The ionization level of metal cations in an aqueous solution might be impacted by the presence of counter anions or charge density, which in turn could affect the yield of 5-MF. The experimental and DFT study results revealed that Sn(IV)-OH species, specifically [Sn(OH)<sub>2</sub>(H<sub>2</sub>O)<sub>4</sub>]<sup>2 +</sup> species as a Lewis acid, predominantly facilitated the tautomerization of chain rhamnose to ketose (rhamnulose), a key step in 5-MF formation, rather than Sn(IV)-Cl species. The Brønsted acid (H<sub>3</sub>O<sup>+</sup>), formed from the SnCl<sub>4</sub> hydrolysis, facilitated the conversion of cyclic rhamnose to chain rhamnose and the final dehydration to yield 5-MF. The chloride ion (Cl<sup>-</sup>) might interact with ether groups in cyclic rhamnose or aldehyde group in chain rhamnose to promote the formation of 5-MF. This work might provide some valuable insights for converting <em>Enteromorpha prolifera</em>-derived rhamnose to 5-MF and improving the utilization of algal biomass.</div></div>","PeriodicalId":13581,"journal":{"name":"Industrial Crops and Products","volume":"226 ","pages":"Article 120661"},"PeriodicalIF":6.2000,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synergistic catalytic effect of various species in SnCl4(aq) for conversion of Enteromorpha prolifera derived rhamnose to 5-methylfurfural\",\"authors\":\"Yuan Xiao , Yuhong Ma , Kaizhuo Lv , Qiuli Yao , Jingtao Liu , Shuguang Xu\",\"doi\":\"10.1016/j.indcrop.2025.120661\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The growing demand for 5-methylfurfural (5-MF) across various applications has driven the pursuit of environmentally friendly production methods. Herein, we proposed a facile and highly efficient method for converting <em>Enteromorpha prolifera</em>-derived rhamnose into 5-methylfurfural (5-MF) in H<sub>2</sub>O/MIBK media using metal chloride salts as catalysts. SnCl<sub>4</sub> was capable of achieving a high 5-MF yield of 68.8 % under optimized conditions. The ionization level of metal cations in an aqueous solution might be impacted by the presence of counter anions or charge density, which in turn could affect the yield of 5-MF. The experimental and DFT study results revealed that Sn(IV)-OH species, specifically [Sn(OH)<sub>2</sub>(H<sub>2</sub>O)<sub>4</sub>]<sup>2 +</sup> species as a Lewis acid, predominantly facilitated the tautomerization of chain rhamnose to ketose (rhamnulose), a key step in 5-MF formation, rather than Sn(IV)-Cl species. The Brønsted acid (H<sub>3</sub>O<sup>+</sup>), formed from the SnCl<sub>4</sub> hydrolysis, facilitated the conversion of cyclic rhamnose to chain rhamnose and the final dehydration to yield 5-MF. The chloride ion (Cl<sup>-</sup>) might interact with ether groups in cyclic rhamnose or aldehyde group in chain rhamnose to promote the formation of 5-MF. This work might provide some valuable insights for converting <em>Enteromorpha prolifera</em>-derived rhamnose to 5-MF and improving the utilization of algal biomass.</div></div>\",\"PeriodicalId\":13581,\"journal\":{\"name\":\"Industrial Crops and Products\",\"volume\":\"226 \",\"pages\":\"Article 120661\"},\"PeriodicalIF\":6.2000,\"publicationDate\":\"2025-02-11\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Industrial Crops and Products\",\"FirstCategoryId\":\"97\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0926669025002079\",\"RegionNum\":1,\"RegionCategory\":\"农林科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"AGRICULTURAL ENGINEERING\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Industrial Crops and Products","FirstCategoryId":"97","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0926669025002079","RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"AGRICULTURAL ENGINEERING","Score":null,"Total":0}
Synergistic catalytic effect of various species in SnCl4(aq) for conversion of Enteromorpha prolifera derived rhamnose to 5-methylfurfural
The growing demand for 5-methylfurfural (5-MF) across various applications has driven the pursuit of environmentally friendly production methods. Herein, we proposed a facile and highly efficient method for converting Enteromorpha prolifera-derived rhamnose into 5-methylfurfural (5-MF) in H2O/MIBK media using metal chloride salts as catalysts. SnCl4 was capable of achieving a high 5-MF yield of 68.8 % under optimized conditions. The ionization level of metal cations in an aqueous solution might be impacted by the presence of counter anions or charge density, which in turn could affect the yield of 5-MF. The experimental and DFT study results revealed that Sn(IV)-OH species, specifically [Sn(OH)2(H2O)4]2 + species as a Lewis acid, predominantly facilitated the tautomerization of chain rhamnose to ketose (rhamnulose), a key step in 5-MF formation, rather than Sn(IV)-Cl species. The Brønsted acid (H3O+), formed from the SnCl4 hydrolysis, facilitated the conversion of cyclic rhamnose to chain rhamnose and the final dehydration to yield 5-MF. The chloride ion (Cl-) might interact with ether groups in cyclic rhamnose or aldehyde group in chain rhamnose to promote the formation of 5-MF. This work might provide some valuable insights for converting Enteromorpha prolifera-derived rhamnose to 5-MF and improving the utilization of algal biomass.
期刊介绍:
Industrial Crops and Products is an International Journal publishing academic and industrial research on industrial (defined as non-food/non-feed) crops and products. Papers concern both crop-oriented and bio-based materials from crops-oriented research, and should be of interest to an international audience, hypothesis driven, and where comparisons are made statistics performed.