Citation: Ji-feng BAI, Man-fang CHENG, Hong-zhu LU, Ming-bo HOU, YANG Yu, Jing-yun WANG, Ming-dong ZHOU. In-situ oxidation of 5-hydroxymethylfurfural to 5-formylfuran-2-carboxylic acid catalyzed by iron, manganese, copper and salicylic amantadine Schiff base ligands[J]. Journal of Fuel Chemistry and Technology, ;2022, 50(4): 418-427. doi: 10.1016/S1872-5813(21)60176-7 shu

In-situ oxidation of 5-hydroxymethylfurfural to 5-formylfuran-2-carboxylic acid catalyzed by iron, manganese, copper and salicylic amantadine Schiff base ligands

1.
School of Petrochemical Technology, Liaoning Shihua University, Fushun 113001, China
2.
PetroChina Fushun Petrochemical Company No 2 Petroleum Plant, Fushun 113004, China

Corresponding author: Jing-yun WANG, jingyun.wang@lnpu.edu.cn
Received Date: 28 April 2021
Revised Date: 12 October 2021

Figures(10)

To synthesize simple and efficient catalysts and their application in catalytic conversion of biomass platform compounds to prepare high value-added chemicals has always been the focus of researchers. In this paper, a catalyst composed of iron, manganese, copper and Schiff base ligand derived from amantadine salicylaldehyde was in-situ constructed to catalyze the selective oxidation of 5-hydroxymethylfurfural (HMF) to prepare 5-formyl-2-furancarboxylic acid (FFCA). The ligands and complexes were characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (IR) and single crystal diffraction, and the reaction conditions such as oxidation reaction time, reaction temperature, molar ratio of MnCl₂·4H₂O to ligand, oxidant and catalyst dosage, etc, were optimized. Under the optimized conditions, 100% conversion of HMF and the FFCA with a yield of 52.1% can be obtained. Finally, on the basis of the reaction results, the HMF oxidation reaction process catalyzed by Mn metal complexes was analyzed.
- 5-hydroxymethylfurfural,
- oxidation,
- Schiff base,
- in-situ catalysis,
- 5-formylfuran-2-carboxylic acid
1. [1]
  MURPHY J D, BROWNE J, ALLEN E, GALLAGHER C. The resource of biomethane, produced via biological, thermal and electrical routes, as a transport biofuel[J]. Renewable Energy,2013,55(1):474−479.
2. [2]
  LICHTENTHALER F W, PETER S. Carbohydrates as green raw materials for the chemical industry[J]. Comptes Rendus Chimie,2004,7(2):65−90. doi: 10.1016/j.crci.2004.02.002
3. [3]
  SIANKEVICH S, SAVOGLIDIS G, FEI Z. A novel platinum nanocatalyst for the oxidation of 5-hydroxymethylfurfural into 2, 5-furandicarboxylic acid under mild conditions[J]. J Catal,2014,315(6):67−74.
4. [4]
  CORMA A, IBORRA S, VELTY A. Chemical routes for the transformation of biomass into chemicals[J]. Chem Rev,2007,107(6):2411−2502. doi: 10.1021/cr050989d
5. [5]
  ROMÁN-LESHKOV Y, CHHEDA J N, DUMESIC J A. Phase modifiers promote efficient production of hydroxymethylfural from fructose[J]. Dumesic Sci,2006,312(5782):1933−1937. doi: 10.1126/science.1126337
6. [6]
  ZHAO H, HOLLADAY J E, BROWN H, ZHANG Z C. Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural[J]. Science,2007,316(5831):1597−1600. doi: 10.1126/science.1141199
7. [7]
  SUN Z, CHENG M X, LI Z J, TIAN J, WANG X H. One pot production of 5-hydroxymethylfurfural with high yield from cellulose by a Brønsted-Lewis- surfactant-combined heteropolyacid catalyst[J]. Chem Commun,2011,47(7):2176−2178. doi: 10.1039/c0cc04444j
8. [8]
  STÅHLBERG T, FU W, WOODLEY J M, RIISAGER A. Synthesis of 5-(hydroxymethyl) furfural in ionic liquids: Paving the way to renewable chemicals[J]. ChemSusChem,2011,4(4):451−458. doi: 10.1002/cssc.201000374
9. [9]
  LAN J, LIN J, CHEN Z, YIN G. Transformation of 5-hydroxymethylfurfural (HMF) to maleic anhydride by aerobic oxidation with heteropolyacid catalysts[J]. ACS Catal,2015,5(4):2035−2041. doi: 10.1021/cs501776n
10. [10]
  PAL P, SARAVANAMURUGAN S. Recent advances in the development of 5-hydroxymethylfurfural oxidation with base (nonprecious)-metal-containing catalysts[J]. ChemSusChem,2018,12(1):145−163.
11. [11]
  ZHANG Z, DENG K. Recent advances in the catalytic synthesis of 2, 5-furandicarboxylic acid and its derivatives[J]. ACS Catal,2015,5(11):6529−6544. doi: 10.1021/acscatal.5b01491
12. [12]
  ZHANG C, CHANG X, ZHU L, XING Q, YOU S, QI W, SU R, HE Z. Highly efficient and selective production of FFCA from CotA-TJ102 laccase-catalyzed oxidation of 5-HMF[J]. Int J Biol Macromol,2019,128(1):132−139.
13. [13]
  GANDINI A, SILVESTRE A J D, NETO C P, SOUSA A F, GOMES M, The furan counterpart of poly(ethylene terephthalate): An alternative material based on renewable resources[J] J Polym Sci Pol Chem, 2009, 47 (1) 295−298.
14. [14]
  XU J J, ZHU Z G, YUAN Z L, SUN T, ZHAO Y C, REN W Z, ZHANG Z H, LÜ H Y. Selective oxidation of 5-hydroxymethylfurfural to 5-formyl-2-furancar- boxylic acid over a Fe-Anderson type catalyst[J]. J Taiwan Inst Chem E,2019,104:8−15.
15. [15]
  ZHU Y, ZHANG Y, CHENG L, ISMAEL M, FENG Z, WU Y. Novel application of g-C₃N₄/NaNbO₃ composite for photocatalytic selective oxidation of biomass-derived HMF to FFCA under visible light irradiation[J]. Adv Powder Technol,2020,31(3):1148−1159. doi: 10.1016/j.apt.2019.12.040
16. [16]
  PAL P, KUMAR S, DEVI M M, SARAVANAMURUGAN S. Oxidation of 5-hydroxymethylfurfural to 5-formyl furan-2-carboxylic acid by non-precious transition metal oxide-based catalyst[J]. J Supercrit Fluids,2020,160(1):104−812.
17. [17]
  VENTURA M, ARESTA M, DIBENEDETTO A. Selective aerobic oxidation of 5-(hydroxymethyl) furfural to 5-formyl-2-furancarboxylic acid in water[J]. ChemSusChem,2016,9(10):1096−1100. doi: 10.1002/cssc.201600060
18. [18]
  VENTURA M, LOBEFARO F, GIGLIO E, DISTASO M, NOCITO F, DIBENEDETTO A. Selective aerobic oxidation o 5-hydroxymethylfurfural to 2, 5-diformylfuran or 2-formyl-5-furancarboxylic acid in water by using MgO·CeO₂ mixed oxides as catalysts[J]. ChemSusChem,2018,11(8):1305−1315. doi: 10.1002/cssc.201800334
19. [19]
  WANG H B. Synthesis, characterization and antibacterial activity of Schiff base containing adamantyl and Its Zinc complex[D]. Liaoning: Liaoning University, 2012.
20. [20]
  JIN X D, WANG W C, FENG X X, BU L C, TONG J, ZHANG P, REN J K, ZHAO B X. Synthesis, characterization, crystal structure, and electrochemical property of copper(II) complexes with Schiff bases derived from 5-halogenated salicylaldehyde and amantadine[J]. J Coord Chem,2017,43(11):787−794. doi: 10.1134/S1070328417110033
21. [21]
  SHELDRICK G M. SHELXT-integrated space-group and cry-synthesis determination[J]. Acta Crystallogr A,2015,71(1):3−8.
22. [22]
  JIN X D, KOU L, LIANG H M, TONG J, ZHANG P, HAN G C, REN J K, ZHAO B X. Syntheses and crystal structures of three copper(II) complexes with bulky Schiff bases derived from rimantadine[J]. J Coord Chem,2016,69(22):3309−3320. doi: 10.1080/00958972.2016.1228910
23. [23]
  KIM M, SU Y Q, FUKUOKA A, HENSEN E J M, NAKAJIMA K. Aerobic oxidation of 5-(hydroxymethyl) furfural cyclic acetal enables selective furan-2, 5-dicarboxylic acid formation with CeO₂-supported gold catalyst[J]. Angew Chem Int Ed,2018,57(27):8235−8239. doi: 10.1002/anie.201805457
24. [24]
  RAO V K, PETER S. Oxidation of biomass derived 5-hydroxymethylfurfural using heterogeneous and electrochemical catalysis[J]. Catal Today, 2012, 195(1): 144−154.
25. [25]
  REN Y S, LIU B, ZHANG Z H, LIN J T. Silver-exchanged heteropolyacid catalyst (Ag₁H₂PW): An efficient heterogeneous catalyst for the synthesis of 5-ethoxymethylfurfural from 5-hydroxymethylfurfural and fructose[J]. J Ind Eng Chem,2015,21(25):1127−1131.
26. [26]
  JU E G, DONG K, CHEN Z W, LIU Z, LIU C Q, HUANG Y Y, WANG Z Z, PU F, REN J S, QU X G. Copper(ii) -graphitic carbon nitride triggered synergy: Improved ros generation and reduced glutathione levels for enhanced photodynamic therapy[J]. Angew Chem Int Ed,2016,55(38):11467−11471. doi: 10.1002/anie.201605509
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]
  Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V₂O₅/TiO₂ catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
3. [3]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
4. [4]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
5. [5]
  Peiyu Zhang , Aixin Song , Jingcheng Hao , Jiwei Cui . 高频超声法制备聚多巴胺薄膜综合实验. University Chemistry, 2025, 40(6): 210-214. doi: 10.12461/PKU.DXHX202407081
6. [6]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
7. [7]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . Construction of 4-Amino-1H-imidazole-5-carbonitrile Modified Carbon Nitride-Based Donor-Acceptor Photocatalyst for Efficient Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-0. doi: 10.3866/PKU.WHXB202406026
8. [8]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
9. [9]
  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
10. [10]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
11. [11]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
12. [12]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
13. [13]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
14. [14]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
15. [15]
  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
16. [16]
  Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO₂-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
17. [17]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 2408015-0. doi: 10.3866/PKU.WHXB202408015
18. [18]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(379)
HTML views(52)

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