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Progress in Chemistry 2022, Vol. 34 Issue (6): 1263-1274 DOI: 10.7536/PC211231 Previous Articles   Next Articles

• Review •

Preparation of Furoic Acid by Oxidation of Furfural

Xinglong Li, Yao Fu()   

  1. School of Chemistry and Materials Science, University of Science and Technology of China,Hefei 230026, China
  • Received: Revised: Online: Published:
  • Contact: Yao Fu
  • Supported by:
    Major Science and Technology Projects of Anhui Province(18030701157); Anhui Natural Science Foundation Project(2008085QB63)
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As an important downstream product of furfural, furoic acid has important applications in food manufacturing, material preparation, optical technology and drug synthesis. It can be used to synthesize preservatives, plasticizers, thermosetting resins, spices and a variety of drugs. At present, there are many reviews on the preparation of furfural and the preparation of downstream compounds by hydrogenation. However, there is no systematic review on the oxidation of furfural to furoic acid. This paper reviews the progress in preparation of furoic acid from furfural in recent years. The effects of different catalytic systems and different oxygen sources on the selectivity of furoic acid are discussed. The application prospect of heterogeneous catalysts in the preparation of furoic acid is highlighted, and the future development direction of furoic acid preparation is prospected.

Contents

1 Introduction

2 Catalytic oxidation system

2.1 Homogeneous oxidation system

2.2 Heterogeneous oxidation system

2.3 Biological oxidation system

3 Conclusion and outlook

Key words: biomass resources, furfural, furoic acid, oxidation, heterogeneous catalysis
Fig. 1 Number of publications on furfural (left) and furoic acid (right) annually in recent years. Source:Web of Science (keyword: furfural)
Fig. 2 Several important downstream compounds prepared by furfural
Fig. 3 Conversion of furoic acid to downstream products
Table 1 Summary of catalytic conversion of furfural to furoic acid by homogeneous catalytic system
Entry Catalyst Reaction conditions Furoic Acid Yield/% ref
1 [Cu(acac)2]/SIMes H2O, 50 ℃, 1 atm O2, 1 eq NaOH, 12 h 99 13
2 triazolium-NHC DABCO(50 mol%), O2, THF, r.t., 16 h 96 15
3 NaOH (1 eq), H2O, air, 80 ℃, 12 h 90 17
4 MeCN, TBD(1.2 eq), air, r.t. 86 17
5 CuCl 2 equiv of 70% t-BuOOH (in water) in MeCN, r.t., 3 h 91 18
6 CuBr2 2 equiv. t-BuOOH (water), MeCN, 1.5 h 92 19
7 Bi2O3 5 equiv. 70% t-BuOOH (water), EtOAc, 10 h 91 20
8 Mohr’s salt DMSO, 5 eq. 70% t-BuOOH, 80 ℃, 3.5 h 92 21
9 I2 NaOH (20 mol%), 4 equiv. t-BuOOH (water), H2O, 70 ℃, 10~16 h 77 22
10 PCC Solvent-free, r.t. 82 23
11 Sodium chlorite MeCN, 10 ℃-r.t., 3 h 90 24
12 H2O2; 60 ℃; CH3CN 76 25
13 CO2, DBU (20 mol%), THF, r.t., 10 min 65 26
14 H2O∶1,4-dioxane=50∶50, 95 ℃, 20 h 13.3 27
Fig. 4 Oxidation of aldehyde to acid by [Cu(acac)2]/SIMes catalysts[13]
Fig. 5 Oxidation of aldehyde to acid by Triazolium NHC catalyst[15]
Fig. 6 Oxidation of aldehyde to acid by iridium complex catalysts[16]
Fig. 7 Oxidation of aldehyde to acid by NHC catalysts[17]
Fig. 8 Oxidation of aldehyde to acid by CuCl and t-BuOOH oxidation system[18]
Fig. 9 Oxidation of aldehydes to carboxylic acids by CuBr2 and t-BuOOH catalytic system[19]
Fig. 10 Oxidation of aldehydes to carboxylic acids by Mohr’s salt and t-BuOOH catalytic system[21]
Fig. 11 Oxidation of alcohols or aldehydes to carboxylic acids by I2 and t-BuOOH catalytic system[22]
Fig. 12 Oxidation of aldehydes to carboxylic acids by PCC under solvent-free conditions[23]
Fig. 13 Oxidation of aldehyde to acid and ester using Ni catalysts[25]
Fig. 14 Catalytic conversion of aldehyde to acid using carbon dioxide mediated NHC catalyst and its reaction mechanism[26]
Fig. 15 Catalytic conversion of aldehyde to acid using Hexamethyl-benzene-supported ruthenium complexes[27]
Table 2 Summary of catalytic conversion of furfural to furoic acid by heterogeneous catalytic system
Entry Catalyst Reaction conditions Furoic Acid Yield/% ref
1 Au/ZTC methanol, 6 bar O2, 120 ℃, 6 h 90 28
2 AuNPs/TiO2 H2O, Na2CO3, 30 ℃, 8 h, UV/Uis 92/96 29
3 SiO2@Au@TiO2 FF : Au ratio=100, 2 h, 24 bar air 99 30
4 Co4HP2Mo15V3O62 [TEBSA][BF4], H2O2, r.t., 4 h 94 31
5 Co-N-C H2O, 120 ℃, 1 MPa O2,1h 96.7 32
6 SiO2-Co(acac)2
SiO2-Co(acac)2		 50 ℃, solvent-free, air, 5 h
70 ℃, H2O, air, 7.5 h		 85
180		 33
7 (NH4)4[CuMo6O18(OH)6] H2O, 50 ℃, O2 balloon, 0.1 eq Na2CO3, 8 h 99 34
8 Ag2O/CuO H2O, 70 ℃, 2 MPa O2, 1 h 99 35
9 CuO NaOH, H2O, 65 ℃, air, 25 min 91 36
10 FeIIIMo6 H2O, 50 ℃, 1 atm O2, 0.1 eq Na2CO3, 8 h 97 37
11 DBU (50 mol%), anhydrous Me-THF, air, r.t. 90 38
12 MnO2 H2O, NaHCO3, 1 MPa O2, 100 ℃, 24 h 95 39
13 Pd/C Methanol-H2O, NaBH4, KOH, air, r.t. 84 40
14 [Ce(NH4)2(NO3)6] (CAN) 1 eq. t-BuOOH (water), MeCN, r.t., 15 min 93 41
15 β- Cyclodextrin 50 ℃, H2O2, 1 h 97(conversion) 42
16 VO(acac)2-TiO2 (TSV) H2O2, MeCN, r.t., 4 h 86 43
17 MOF-TEMPO 1) 5 mol% catalyst, 20 mol% TBN, CH3CN, O2, 25 ℃, 2 h;2) the filtration of catalyst and additional stirring under O2 balloon at 80 ℃ for 10 h 80 44
Fig. 16 Conversion of furfural to furoic acid by using Co4HP2Mo15V3O62/H2O2 catalytic system[31]
Fig. 17 Conversion of aldehydes to acids catalyzed by iron (Ⅱ) phthalocyanine and heterogeneous triazolium catalytic system[38]
Fig. 18 Conversion of furfuryl alcohol or furfural to furoic acid by using MnO2 as catalysts[39]
Fig. 19 Conversion of furfuryl alcohol to furoic acid by using MOF-TEMPO as catalysts[44]
Fig. 20 Oxidation of aldehydes by ALDHs using NOX for coenzyme recycling[48]
Fig. 21 A dual-enzyme cascade system of GOase and ADHs for catalytic oxidation of aldehydes to carboxylic acids[50]
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