Citation: ZHANG Shuang, ZHANG Long. Dehydration of Fructose into 5-Hydroxymethylfurfural Catalyzed by Ethylene Tar Char Sulfonic Acid[J]. Chinese Journal of Applied Chemistry, ;2020, 37(3): 314-321. doi: 10.11944/j.issn.1000-0518.2020.03.190278 shu

Dehydration of Fructose into 5-Hydroxymethylfurfural Catalyzed by Ethylene Tar Char Sulfonic Acid

ZHANG Shuang ^a ,
ZHANG Long ^b,,

a.
Institute of Petrochemical Technology Jilin Institute of Chemical Technology, Jilin, Jilin 132022, China
b.
School of Chemical Engineering, Changchun University of Technology, Changchun 130012, China

Corresponding author: ZHANG Long, zhanglongzhl@163.com
Received Date: 18 October 2019
Revised Date: 3 December 2019
Accepted Date: 25 December 2019

Fund Project: the "Thirteen Five Years" Science and Technology Project of the Education Department of Jilin Province JJKH20190835KJSupported by the "Thirteen Five Years" Science and Technology Project of the Education Department of Jilin Province(No.JJKH20190835KJ)

Figures(10)

Ethylene tar char sulfonic acid was prepared by crosslinking and sulfonating method with the heavy components of ethylene tar after distillation as the raw material. The structure and properties of the catalyst were characterized by Flourier transformation infrared spectroscopy (FT-IR), X-ray diffraction (XRD), Raman spectroscopy, thermogravimetric analysis (TGA-DTG), and scanning electron microscopy (SEM). The results showed that the catalyst presented an amorphous graphite carbon structure and high acid content (4.20 mmol/g). The sulfonic acid functional group on the surface was the key active center. The catalyst was used for the dehydration of fructose into 5-hydroxymethylfurfural (5-HMF). At the reaction time of 140 min, temperatureat of 130℃, the catalyst dosage of 0.3 g, the solvent dosage of 8 mL and the additive dosage of 0.3 g, the conversion of fructose and the yield of 5-HMF were 96.2% and 52.1%, respectively. The purity of 5-HMF obtained by separation was 97.0%. The conversion of fructose and the yield of 5-HMF remained above 85.1% and 40.8% after the catalyst was recycled five times.
- fructose,
- 5-hydroxymethylfurfural,
- ethylene tar,
- char sulfonic acid
1. [1]
  Hara M, Yoshida T, Takagaki A. A Carbon Material as a Strong Protonic Acid[J]. Angew Chem Int Ed, 2004,116(22):3015-3018.
2. [2]
  Toda M, Takagaki A, Okamura M. Green Chemistry-Biodiesel Made with Sugar Catalyst[J]. Nature, 2005,438(7065):178-178.
3. [3]
  Gao S, Liang X, Yang J. High Efficient Acetalizaton of Carbonyl Compounds with Diols Catalyzed by Novel Carbon-Based Solid Strong Acid Catalyst[J]. Chinese Sci Bull, 2007,52(21):2892-2895.
4. [4]
  Gao S, Liang X, Yang J. An Efficient Heterogeneous Procedure for the Catalytic Acetalization and Ketalization at Room Temperature under Solvent-Free Condition[J]. Chinese Sci Bull, 2008,53(10):1484-1488.
5. [5]
  Boonoun P, Laosiripojana N, Shotipruk A. Application of Sulfonated Carbon-Based Catalyst for Reactive Extraction of 1, 3-Propanediol from Model Fermentation Mixture[J]. Ind Eng Chem Res, 2010,49:12352-12357.
6. [6]
  Daengprasert W, Boonnoun P, Shotipruk A. Application of Sulfonated Carbon-Based Catalyst for Solvothermal Conversion of Cassava Waste to Hydroxymethylfurfural and Furfural[J]. Ind Eng Chem Res, 2011,50:7903-7910.
7. [7]
  Tanemura K, Suzuki T, Nishida Y. Synthesis of the Sulfonated Condensed Polynuclear Aromatic(S-COPNA) Resins as Strong Protonic Acids[J]. Tetrahedron, 2011,67(6):1314-1319.
8. [8]
  Tanemura K, Suzuki T, Horaguchi T. Synthesis of Sulfonated Polynaphthalene, Polyanthracene, and Polypyrene as Strong Solid Acids via Oxidative Coupling Polymerization[J]. J Appl Polym Sci, 2013,127(6):4524-4536. doi: 10.1002/app.38045
9. [9]
  ZHAN Yingying, YANG Wenxia, LIU Yingxin. Progress in Preparation and Application of Carbon-Based Solid Acid Catalysts[J]. Zhejiang Chem Ind, 2016,47(1):21-25.
10. [10]
  Wu M, Zheng J, Qiu J. Synthesis and Characterization of Condensed Poly-Nuclear Aromatic Resin using Heavy Distillate from Ethylene Tar[J]. New Carbon Mater, 2012,27(6):469-475.
11. [11]
  Ge C, Long D, Ling L. Preparation and Characterization of High Softening Point and Homogeneous Isotropic Pitches Produced from Distilled Ethylene Tar by a Novel Bromination Method[J]. New Carbon Mater, 2018,33(1):71-81.
12. [12]
  GUAN Shengnan, LI Huipeng, ZHAO Hua. Preparation of Biodiesel Catalyzed by Potato Powder Carbon-Based Solid Acid[J]. China Oils Fats, 2019,44(6):75-88.
13. [13]
  JIANG Wenjing, CHEN Hong, SONG Huaihe. Preparation and Performance of COPNA Resin from Bamboo Tar[J]. Carbon Technol, 2016,4(35):41-44.
14. [14]
  Yu J T, Dehkhoda A M, Ellis N. Development of Biochar-Based Catalyst for Transesterification of Canola Oil[J]. Energy Fuels, 2011,25:337-344.
15. [15]
  XU Qiong. Study on Preparation and Catalytic Performances of Biomass Char Sulfonic Acids[D]. Hunan Normal University, 2008(in Chinese).
16. [16]
  YANG Shasha, ZHANG Jianghua, LI Hongyan. Chitosan-derived Solid Acid as a Catalyst for Fructose Dehydration into 5-Hydroxymethylfurural[J]. Fine Chem, 2019,36(8):1591-1597.
17. [17]
  NIE Guangxia. Research on the Dehydration of Fructose to 5-Hydroxymethyl Furfural Catalyzed by Graphite Derivates as the Catalysts[D]. Tianjing: Tianjin University of Technology, 2015(in Chinese).
18. [18]
  Carniti P, Gervasini A, Marzo M. Absence of Expected Side-Reactions in the Dehydration Reaction of Fructose to 5-HMF in Water over Niobic Acid Catalyst[J]. Catal Commun, 2011,12:1122-1126.
19. [19]
  Dou Y, Zhou S, Oldani C. 5-Hydroxymethylfurfural Production from Dehydration of Fructose Catalyzed by Aquivion@Silica Solid Acid[J]. Fuel, 2018,214:45-54.
20. [20]
  LI Zhenzhen. Catalytic Conversion of Fructose into 5-Hydroxymethylfurfural in Isopropanol[D]. South China University of Technology, 2014(in Chinese).
21. [21]
  WU Lili. Studies on the Preparation of Hickory Hull Char Sulfonic Acid Catalyst and its Applications[D]. East China Jiaotong University, 2015(in Chinese).
22. [22]
  Zhang M, Jiang H, Li G. High Activity Ordered Mesoporous Carbon-Based Solid Acid Catalyst for the Esterification of Free Fatty Acids[J]. Micropor Mesopor Mater, 2015,204:210-217.
1. [1]
  Meiran Li , Yingjie Song , Xin Wan , Yang Li , Yiqi Luo , Yeheng He , Bowen Xia , Hua Zhou , Mingfei Shao . Nickel-Vanadium Layered Double Hydroxides for Efficient and Scalable Electrooxidation of 5-Hydroxymethylfurfural Coupled with Hydrogen Generation. Acta Physico-Chimica Sinica, 2024, 40(9): 2306007-0. doi: 10.3866/PKU.WHXB202306007
2. [2]
  Xiaoyang Li , Xiaowei Huang , Yimeng Zhang , Huan Liu , Shao Jin , Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035
3. [3]
  Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
4. [4]
  Bolin Sun , Jie Chen , Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032
5. [5]
  Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
6. [6]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
7. [7]
  Zhenghua ZHAO , Qin ZHANG , Yufeng LIU , Zifa SHI , Jinzhong GU . Syntheses, crystal structures, catalytic and anti-wear properties of nickel(Ⅱ) and zinc(Ⅱ) coordination polymers based on 5-(2-carboxyphenyl)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 621-628. doi: 10.11862/CJIC.20230342
8. [8]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
9. [9]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
10. [10]
  Xiaosong PU , Hangkai WU , Taohong LI , Huijuan LI , Shouqing LIU , Yuanbo HUANG , Xuemei LI . Adsorption performance and removal mechanism of Cd(Ⅱ) in water by magnesium modified carbon foam. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1537-1548. doi: 10.11862/CJIC.20240030
11. [11]
  Qianqian ZHU , Lihui XU , Hong PAN , Chengjian YAO , Hong ZHAO , Nan MA , Xiaolin SHI , Zihan SHEN , Weijun ZHANG , Zhongjian WANG . Waste cotton fabric-ased porous carbon materials: Preparation and wave-absorbing properties. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1555-1564. doi: 10.11862/CJIC.20250040
12. [12]
  Yang ZHOU , Lili YAN , Wenjuan ZHANG , Pinhua RAO . Thermal regeneration of biogas residue biochar and the ammonia nitrogen adsorption properties. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1574-1588. doi: 10.11862/CJIC.20250032
13. [13]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
14. [14]
  Zhaoxuan ZHU , Lixin WANG , Xiaoning TANG , Long LI , Yan SHI , Jiaojing SHAO . Application of poly(vinyl alcohol) conductive hydrogel electrolytes in zinc ion batteries. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 893-902. doi: 10.11862/CJIC.20240368
15. [15]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
16. [16]
  Jing Zhang , Su Zhang , Qiqi Li , Linken Ji , Yutong Li , Yukang Ren , Xiaobei Zang , Ning Cao , Han Hu , Peng Liang , Zhuangjun Fan . Integrating high surface area and electric conductivity in activated carbon by in situ formation of the less-defective carbon network during selective chemical etching. Acta Physico-Chimica Sinica, 2025, 41(10): 100114-0. doi: 10.1016/j.actphy.2025.100114
17. [17]
  Guanghui SUI , Yanyan CHENG . Application of rice husk-based activated carbon-loaded MgO composite for symmetric supercapacitors. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 521-530. doi: 10.11862/CJIC.20240221
18. [18]
  Qiqi Li , Su Zhang , Yuting Jiang , Linna Zhu , Nannan Guo , Jing Zhang , Yutong Li , Tong Wei , Zhuangjun Fan . Preparation of High Density Activated Carbon by Mechanical Compression of Precursors for Compact Capacitive Energy Storage. Acta Physico-Chimica Sinica, 2025, 41(3): 100028-0. doi: 10.3866/PKU.WHXB202406009
19. [19]
  Ling WANG , Weipeng YAN , Zhuoyi ZHENG , Sihan ZHU , Mingxian GONG , Xiangyu MA . Fabrication of biochar-supported nano zero-valent iron and its high-efficiency performance for Cr(Ⅵ) removal from wastewater. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2441-2454. doi: 10.11862/CJIC.20250264
20. [20]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(2687)
HTML views(610)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142