Efficient isomerization of glucose to fructose co-catalyzed with basic ionic liquid and sodium borate

XIANG Xiaoyan; WEI Yi; PEI Baoyou; QIU Rongxing; CHEN Xiaoyan; ZHAO Zhaoyang; LUO Xiaoyan; LIN Jinqing

doi:10.11949/0438-1157.20191201

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Efficient isomerization of glucose to fructose co-catalyzed with basic ionic liquid and sodium borate

Catalysis\, kinetics and reactors | 更新时间：2026-07-24

- Efficient isomerization of glucose to fructose co-catalyzed with basic ionic liquid and sodium borate
- CIESC Journal Vol. 71, Issue 1, Pages: 290-296(2020)
- 作者机构：
  
  1.华侨大学材料科学与工程学院，福建厦门361021
  2.龙岩学院化学与材料学院，福建龙岩 364000
- 作者简介：
- 基金信息：
- DOI：10.11949/0438-1157.20191201
  CLC： O 643
- Received：15 October 2019，
  
  Revised：2019-10-21，
  
  Online First：12 August 2020，
  
  Published：05 January 2020
- 稿件说明：
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项小燕, 危依, 裴宝有, 丘荣星, 陈晓燕, 赵朝阳, 罗小燕, 林金清. 碱性离子液体协同配合剂催化葡萄糖异构化制备果糖[J]. 化工学报, 2020, 71(1): 290-296

XIANG Xiaoyan, WEI Yi, PEI Baoyou, QIU Rongxing, CHEN Xiaoyan, ZHAO Zhaoyang, LUO Xiaoyan, LIN Jinqing. Efficient isomerization of glucose to fructose co-catalyzed with basic ionic liquid and sodium borate[J]. CIESC Journal, 2020, 71(1): 290-296
项小燕, 危依, 裴宝有, 丘荣星, 陈晓燕, 赵朝阳, 罗小燕, 林金清. 碱性离子液体协同配合剂催化葡萄糖异构化制备果糖[J]. 化工学报, 2020, 71(1): 290-296 DOI： 10.11949/0438-1157.20191201.

XIANG Xiaoyan, WEI Yi, PEI Baoyou, QIU Rongxing, CHEN Xiaoyan, ZHAO Zhaoyang, LUO Xiaoyan, LIN Jinqing. Efficient isomerization of glucose to fructose co-catalyzed with basic ionic liquid and sodium borate[J]. CIESC Journal, 2020, 71(1): 290-296 DOI： 10.11949/0438-1157.20191201.

摘要

糖类是生物质的重要组成部分，可经催化转化制得一系列高附加值化学品，具有经济价值高、对环境友好和可持续性强等优点。葡萄糖异构为果糖是该过程的关键步骤。本文合成了四种碱功能性离子液体，用红外光谱、核磁共振谱仪和热重分析进行了表征，并用于催化葡萄糖异构化制备果糖，结果表明碱性离子液体具有较好的催化活性，但易使果糖进一步催化降解，同时加入硼酸钠可提高葡萄糖的转化率和果糖的产率，说明硼酸钠既起配合保护剂的作用，也有一定的协同催化作用。考察了离子液体用量、硼酸钠用量、时间、温度等因素对果糖选择性和产率的影响，结果表明，在离子液体和硼酸钠与葡萄糖的摩尔比分别为3∶1和0.08∶1、反应温度为70℃、反应时间为7 min的最佳反应条件下果糖的产率可高达64.7%，选择性为73.1%。

Abstract

Carbohydrates are an important part of biomass and can be converted into a series of high value-added chemicals through catalytic conversion

which has the advantages of high economic value

environmental friendliness and sustainability. Isomerization of glucose into fructose is a key step in the process. Herein

four basic functional ionic liquids: [HOEtMim

]

Phen

[EMim

]

Phen

[HOEtMim

]

[Ch

]

Phen were synthesized and their catalytic performances on glucose isomerization were investigated. A comparison of direct transformation and catalysts combined with sodium borate complex was discussed. It showed that four basic ionic liquids exhibit good catalytic activities

but fructose is easily to be further degraded. While ionic liquids added with sodium borate obtain much higher fructose yields. It indicates that sodium borate plays an important role in both protective agent and synergistic catalysis. [Ch

]

Phen added with sodium borate is the most efficient. The basic structure parameters of [Ch

]

Phen were further characterized by

H NMR

FT-IR and TG-DTG techniques. The effects of reaction temperature

reaction time

the dosage of catalyst and sodium borate on the isomerization and the optimal reaction conditions were investigated by single factor method. The yield of fructose is up to 64.7% with a high selectivity of 73.1% under the optimum condition at 70℃ within 7 min.

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references

Sudarsanam P , Peeters E , Makshina E V , et al . Advances in porous and nanoscale catalysts for viable biomass conversion [J ] . Chem. Soc. Rev. , 2019 , 48 ( 8 ): 2366 - 2421 .

Steinbach D , Kruse A , Sauer J . Pretreatment technologies of lignocellulosic biomass in water in view of furfural and 5-hydroxymethylfurfural production—a review [J ] . Biomass Convers. Bior ., 2017 , 7 ( 2 ): 1 - 28 .

Lei H , Lu L , Zhen W , et al . Recent advances in catalytic transformation of biomass-derived 5-hydroxymethylfurfural into the innovative fuels and chemicals [J ] . Renew Sust. Energ. Rev. , 2017 , 74 : 230 - 257 .

Bosilj M , Schmidt J , Fischer A , et al . One pot conversion of glucose to ethyl levulinate over a porous hydrothermal acid catalyst in green solvents [J ] . RSC Adv ., 2019 , 9 ( 35 ): 20341 - 20344 .

Villanueva N I , Marzialetti T G . Mechanism and kinetic parameters of glucose and fructose dehydration to 5-hydroxymethylfurfural over solid phosphate catalysts in water [J ] . Catal. Today , 2018 , 302 : 100 - 107 .

Wang X , Liang F , Huang C , et al . Siliceous tin phosphates as effective bifunctional catalysts for selective conversion of dihydroxyacetone to lactic acid [J ] . Catal. Sci. Technol. , 2016 , ( 6 ): 6551 - 6560 .

Luo Q , Zhang Y , Qi L , et al . Glucose isomerization and epimerization over metal- organic frameworks with single-site active centers [J ] . ChemCatChem , 2019 , 11 ( 7 ): 1903 - 1909 .

Olson N , Deshpande N , Gunduz S , et al . Utilizing imogolite nanotubes as a tunable catalytic material for the selective isomerization of glucose to fructose [J ] . Catal. Today , 2019 , 323 : 69 - 75 .

Pienkoß F , Ochoa-Hernández C , Theyssen N , et al . Kaolin: a natural low-cost material as catalyst for isomerization of glucose to fructose [J ] . ACS Sust. Chem. Eng. , 2018 , 6 ( 7 ): 8782 - 8789 .

Qi T , He M , Zhu L , et al . Cooperative catalytic performance of Lewis and Brønsted acids from AlCl 3 salt in aqueous solution toward glucose-to-fructose isomerization [J ] . J. Phys. Chem. C , 2019 , 123 ( 8 ): 4879 - 4891 .

Yabushita M , Shibayama N , Nakajima K , et al . Selective glucose-to-fructose isomerization in ethanol catalyzed by hydrotalcites [J ] . ACS Catal ., 2019 , ( 9 ): 2101 - 2109 .

Liu C , Carraher J M , Swedberg J L , et al . Selective base-catalyzed isomerization of glucose to fructose [J ] . ACS Catal ., 2014 , 4 ( 12 ): 4295 - 4298 .

Bruyn C A L D , Ekenstein W A V . Action des alcalis sur les sucres: Ⅱ [J ] . Recueil des Travaux Chimiques des Pays-Bas , 1895 , 14 : 203 - 216 .

Knill C J , Kennedy J F . Degradation of cellulose under alkaline conditions [J ] . Carbohyd. Polym ., 2003 , 51 ( 3 ): 281 - 300 .

Yang B Y , Montgomery R . Alkaline degradation of glucose: effect of initial concentration of reactants [J ] . Carbohyd. Res. , 1996 , 280 ( 1 ): 27 - 45 .

Rendleman J A , Hodge J E . Complexes of carbohydrates with aluminate ion aldose-ketose interconversion on anion-exchange resin (aluminate and hydroxide forms) [J ] . Carbohyd. Res. , 1979 , 75 : 83 - 99 .

Berg R V D , Peters J A , Bekkum H V . The structure and (local) stability constants of borate esters of mono- and di-saccharides as studied by 11 B and 13 C NMR spectroscopy [J ] . Carbohyd. Res. , 1994 , 253 : 1 - 12 .

Sayago C M , González E A , Ivanova S , et al . Epimerization of glucose over ionic liquid/phosphomolybdate hybrids: structure-activity relationship [J ] . Green Chem. , 2018 , 20 ( 5 ): 1042 - 1049 .

Singh S , Simmons B A , Vogel K P . Visualization of biomass solubilization and cellulose regeneration during ionic liquid pretreatment of switchgrass [J ] . Biotechnol. Bioeng ., 2010 , 104 ( 1 ): 68 - 75 .

Hou Q , Ju M , Li W , et al . Pretreatment of lignocellulosic biomass with ionic liquids and ionic liquid-based solvent systems [J ] . Molecules , 2017 , 22 ( 3 ): 490 .

Yang Y , Zhang C , Zhang Z C . Advances in catalytic transformations of carbohydrates and lignin in ionic liquids and mechanistic studies [J ] . WIREs: Energy Environ ., 2018 , 7 ( 3 ): e284 .

Saravanamurugan S , Paniagua M , Melero J A , et al . Efficient isomerization of glucose to fructose over zeolites inconsecutive reactions in alcohol and aqueous media [J ] . J. Am. Chem. Soc. , 2013 , 135 ( 14 ): 5246 - 5249 .

Zhang X , Li H , Li X , et al . Glucose aqueous isomerization catalyzed by basic ionic liquids [J ] . ACS Sust. Chem. Eng. , 2019 , 7 : 13247 - 13256 .

张雄 . 碱性离子液体催化葡萄糖化学异构制备果糖的研究 [D ] . 广州 : 华南理工大学 , 2017 .

Zhang X . The isomerization of glucose into fructose over alkaline ionic liquids [D ] . Guangzhou : South China University of Technology , 2017 .

Ståhlberg T , Rodriguez-Rodriguez S , Fristrup P , et al . Metal-free dehydration of glucose to 5-(hydroxymethyl)furfural in ionic liquids with boric acid as a promoter [J ] . Chem. Eur. J ., 2011 , 17 : 1456 - 1464 .

李文侠 . 葡萄糖化学催化法异构为果糖及其分离研究 [D ] . 厦门 : 厦门大学 , 2015 .

Li W X . Study on the glucose isomerization and separation of glucose and fructose [D ] . Xiamen : Xiamen University , 2015 .

Liu Q P , Hou X D , Li N , et al . Ionic liquids from renewable biomaterials: synthesis, characterization and application in the pretreatment of biomass [J ] . Green Chemistry , 2012 , 14 ( 2 ): 304 - 307 .

Guan Q , Lei T , Wang Z , et al . Preparation of ethyl levulinate from wheat straw catalysed by sulfonate ionic liquid [J ] . Ind. Crop. Prod ., 2018 , 113 : 150 - 156 .

Ma H , Wang F , Yu Y , et al . Autocatalytic production of 5-hydroxymethylfurfural from fructose-based carbohydrates in a biphasic system and its purification [J ] . Ind. Eng. Chem. Res. , 2015 . 54 ( 10 ): 2657 - 2666 .

Zhang N , Meng X , Wu Y , et al . Highly selective isomerization of glucose into fructose catalyzed by a mimic glucose isomerase [J ] . ChemCatChem , 2019 , 11 ( 9 ): 2355 - 2361 .

Yang Q , Zhou S , Runge T . Magnetically separable base catalysts for isomerization of glucose to fructose [J ] . J. Catal ., 2015 , 330 : 474 - 484 .

Tsapatsis M , Guo Q , Ren L , et al . A chromium hydroxide/MIL-101(Cr) composite catalyst and its use for selective glucose isomerization to fructose [J ] . Angew. Chem. Int. Edit ., 2018 , 57 : 4926 - 4930 .

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