Citation: | ZHANG Ruonan, LI Gang, MA Zhongmin, LÜ Qiang. Dehydration of Sugar Mixtures to 5-Hydroxymethylfurfural Catalyzed by Modified Tin-Mordenite[J]. Journal of Fuel Chemistry and Technology. doi: 10.19906/j.cnki.JFCT.2024018 |
[1] |
LI X L, ZHANG K, CHEN S Y, et al. A cobalt catalyst for reductive etherification of 5-hydroxymethyl-furfural to 2, 5-bis(methoxymethyl)furan under mild conditions[J]. Green Chemistry,2018,20(5):1095−1105. doi: 10.1039/C7GC03072J
|
[2] |
YAN K, JARVIS C, GU J , et al. Production and catalytic transformation of levulinic acid: A platform for speciality chemicals and fuels[J]. Renewable & Sustainable Energy Reviews, 2015, 51: 986-997.
|
[3] |
张军, 李丹妮, 袁浩然等. 生物质基糠醛和5-羟甲基糠醛加氢转化研究进展[J]. 燃料化学学报,2021,49(12):1752−1767. doi: 10.1016/S1872-5813(21)60135-4
ZHANG Jun, LI Danni, YUAN Haoran, et al. Progress in the hydroconversion of biomass-based furfural and 5-hydroxymethylfurfura[J]. J Fuel Chem Technol,2021,49(12):1752−1767. doi: 10.1016/S1872-5813(21)60135-4
|
[4] |
张云雷. 基于糖类生物质资源转化制备5-羟甲基糠醛的多孔催化剂设计及其催化性能与机理研究[D]. 镇江: 江苏大学, 2018.
ZHANG Yunlei. Design of porous catalysts for the preparation of 5-hydroxymethylfurfural based on the conversion of sugar biomass resources and study of its catalytic performance and mechanism[D]. Zhenjiang: Jiangsu University, 2018.)
|
[5] |
LIN C , WU H , WANG J , et al. Preparation of HMF from High Fructose Corn Syrup Using Organic weak Acid in situ as Catalyst[J]. Industrial & Engineering Chemistry Research, 2020, 59(10) : 4358-4366.
|
[6] |
GODAN T K, DEVENDRA L P, ALPHY M P, et al. Catalytic synthesis of 5-hydroxymethyl furfural from sorghum syrup derived fructose[J]. Sustainable Energy Technologies and Assessments,2022,54:102884. doi: 10.1016/j.seta.2022.102884
|
[7] |
DE SOUZA R L, YU H, RATABOUL F, et al. 5-Hydroxymethylfurfural (5-HMF) Production from Hexoses: Limits of Heterogeneous Catalysis in Hydrothermal Conditions and Potential of Concentrated Aqueous Organic Acids as Reactive Solvent System[J]. Challenges,2012,3(2):212−232. doi: 10.3390/challe3020212
|
[8] |
MATSUMIYA, H. & HARA, T. Conversion of glucose into 5-hydroxymethylfurfural with boric acid in molten mixtures of choline salts and carboxylic acids[J]. Biomass and Bioenergy,2015,72:227−232. doi: 10.1016/j.biombioe.2014.11.001
|
[9] |
NGUYEN L H T, VO H T, PHAN H B, et al. Synthesis of 5-hydroxymethylfurfural from monosaccharides catalyzed by superacid VNU-11-SO4 in 1-ethyl-3-methylimidazolium chloride ionic liquid[J]. RSC Advances,2020,10(65):39687−39692. doi: 10.1039/D0RA08261A
|
[10] |
RASRENDRA C B , SOETEDJO J N M , MAKERTIHARTHA I G B N , et al. The Catalytic Conversion of d-Glucose to 5-Hydroxymethylfurfural in DMSO Using Metal Salts[J]. Topics in Catalysis, 2012, 55(7-10): 543-549.
|
[11] |
Y. H. WANG, X. L. TONG, Y. T. YAN, et al. Efficient and selective conversion of hexose to 5-hydroxymethylfurfural with tin-zirconium-containing heterogeneous catalysts[J]. Catalysis Communications, 2014, 50: 38-43.
|
[12] |
王建刚, 张云云, 王勇等. 分级有序多孔磺化碳催化果糖转化制5-羟甲基糠醛[J]. 燃料化学学报,2016,44(11):1341−1348. doi: 10.1016/S1872-5813(16)30058-5
WANG Jiangang, ZHANG Yueyue, WANG Yong, et al. Catalytic conversion of fructose to 5-hydroxymethylfurfural by hierarchically ordered porous sulfonated carbon[J]. J Fuel Chem Technol,2016,44(11):1341−1348. doi: 10.1016/S1872-5813(16)30058-5
|
[13] |
ZHANG Y , JIN P , MENG M , et al. Acid-Base Bifunctional Metal-Organic Frameworks: Green Synthesis and Application in One-Pot Glucose to 5-HMF Conversion[J]. Nano brief reports and reviews, 2018, 13(11): 1850132.
|
[14] |
TEMPELMAN C, JACOBS U, HUT T, et al. Sn exchanged acidic ion exchange resin for the stable and continuous production of 5-HMF from glucose at low temperature[J]. Applied Catalysis A-General,2019,588:117267. doi: 10.1016/j.apcata.2019.117267
|
[15] |
YANG H, GUO Q, YANG P, et al. Synthesis of hierarchical Sn-Beta zeolite and its catalytic performance in glucose conversion[J]. Catalysis Today,2021,367:117−123. doi: 10.1016/j.cattod.2020.06.079
|
[16] |
ZHAO H B, HOLLADA J E, BROWN H, et al. Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural[J]. Science,2007,316(5831):1597−1600. doi: 10.1126/science.1141199
|
[17] |
MOLINER M, ROMÁN-LESHKOV Y, DAVIS ME. Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water[J]. Proceedings of the National Academy of Sciences of the United States of America,2010,107(14):6164−6168.
|
[18] |
GUO Q, REN L, ALHASSAN S, et al. Glucose isomerization in dioxane/water with Sn-β catalyst: improved catalyst stability and use for HMF production[J]. Chemical Communications,2019,55(99):14942−14945. doi: 10.1039/C9CC07842H
|
[19] |
NIKOLLA E, ROMAN-LESHKOY Y, MOLINER M, et al. “One-Pot” Synthesis of 5-(Hydroxymethyl)furfural from Carbohydrates using Tin-Beta Zeolite[J]. ACS Catalysis,2011,1(4):408−410. doi: 10.1021/cs2000544
|
[20] |
麻忠敏. 改性分子筛催化果糖脱水制备5-羟甲基糠醛[D]. 大连: 大连理工大学, 2023.
MA Zhongmin. Dehydration of fructose to 5-hydroxymethylfurfural catalyzed by modified molecular sieves[D]. Dalian: Dalian University of Technology, 2023.)
|
[21] |
LI Y P , HEAD-GORDON M , BELL A T. Analysis of the Reaction Mechanism and Catalytic Activity of Metal-Substituted Beta Zeolite for the Isomerization of Glucose to Fructose[J]. ACS Catalysis, 2014, 4(5): 1537-1545.
|
[22] |
张法智. 钛硅分子筛的气固相法制备、表征及其丙烯环氧化性能的研究[D]. 大连: 大连理工大学, 2000.
ZHANG Fazhi. Preparation and characterization of titanium-silicon molecular sieves by gas-solid phase method and their propylene epoxidation properties[D]. Dalian: Dalian University of Technology, 2000.)
|
[23] |
BAYU A , KARNJANAKOM S , KUSAKABE K , et al. Preparation of Sn-β-zeolite via immobilization of Sn/choline chloride complex for glucose-fructose isomerization reaction[J]. Chinese Journal of Catalysis, 2017, 38(3): 426-433.
|
[24] |
王焕英. 介孔丝光沸石的制备与表征[D]. 金华: 浙江师范大学, 2011.
WANG Huanying. Preparation and characterization of mesoporous mordenite zeolites[D]. Jinhua: Zhejiang Normal University, 2011.)
|
[25] |
DWYER J , KARIM K. The incorporation of heteroatoms into faujastic framework by secondary synthesis using aqueous fluoride complexes[J]. Journal of the Chemical Society Chemical Communications, 1991, 14(14): 905-906.
|
[26] |
GRIEKEN R V , MARTOS C , Manuel S. , et al. Synthesis of Sn-silicalite from hydrothermal conversion of SiO2-SnO2 xerogels[J]. Microporous and Mesoporous Materials, 2009, 119(1): 176-185.
|
[27] |
DIJKMANS J , GABRIELS D , DUSSELIER M , et al. Productive sugar isomerization with highly active Sn in dealuminated β zeolites[J]. Green Chemistry, 2013, 15(10): 2777-2785.
|
[28] |
BAI G, MA Z, SHI L J, et al. An effective lactic acid-modified Hβ zeolite for synthesis of bis(indolyl)methanes[J]. Research on Chemical Intermediates,2012,38(9):2501−2510. doi: 10.1007/s11164-012-0567-0
|
[29] |
ROMAN -LESHKOY Y, MOLINER M, LABINGER J A, et al. Mechanism of Glucose Isomerization Using a Solid Lewis Acid Catalyst in water[J]. Angew. Chem. Int. Ed.,2010,49(47):8954−8957. doi: 10.1002/anie.201004689
|
[30] |
TAARNING E , SARAVANAMURUGAN S , HOLM M S , et al. Zeolite-Catalyzed Isomerization of Triose Sugars[J]. Chemsuschem, 2010, 2(7): 625-627.
|
[31] |
吴宁馨. Hf基ZSM-5催化剂催化生物质衍生糖转化制备5-羟甲基糠醛的研究[D]. 南京: 东南大学, 2021.
WU Ningxin. Preparation of 5-hydroxymethylfurfural from biomass-derived sugar conversion catalysed by Hf-based ZSM-5 catalysts [D]. Nanjing: Southeast University, 2021.)
|
[32] |
PANDE, ASHWINI, NIPHADKAR, et al. Acid Modified H-USY Zeolite for Efficient Catalytic Transformation of Fructose to 5-Hydroxymethyl Furfural (Biofuel Precursor) in Methyl lsobutyl Ketone-Water Biphasic System[J]. Energy & Fuels,2018,32(3):3783−3791.
|
[33] |
李宏伟. Sn-Beta沸石的气固相法合成、表征及催化性能研究[D]. 大连: 大连理工大学, 2013.
LI Hongwei. Gas-solid phase synthesis, characterization and catalytic properties of Sn-Beta zeolite[D]. Dalian: Dalian University of Technology, 2000.)
|
[34] |
WOLF P, VALLA M , NUNEZ-ZARUR F , et al. Correlating synthetic methods, morphology, atomic-level structure, and catalytic activity of Sn-beta catalysts[J]. ACS Catalysis, 2016, 6(7): 4047-4063.
|
[35] |
邱果. 碳水化合物制备5-羟甲基糠醛的固体酸催化剂制备及催化机制[D]. 北京: 北京化工大学, 2020.
QIU Guo. Preparation and catalytic mechanism of solid acid catalysts for the preparation of 5-hydroxymethylfurfural from carbohydrates[D]. Beijin: Beijing University of Chemical Technology, 2020.)
|
[36] |
HU Y X, LI H, HU P, et al. Probing the effects of fructose concentration on the evolution of humins during fructose dehydration[J]. Reaction Chemistry & Engineering,2023,8(1):175−183.
|