High-Efficiency Preparation of 2,5-Diformylfuran with a Keto-ABNO Catalyst Under Mild Conditions
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摘要
In this paper, we report a new catalytic system for realizing the rapid and efficient oxidation of 5-hydroxymethylfurfural(HMF). First, we used 9-azabicyclo [3.3.1]nonan-3-one-N-oxyl(keto-ABNO) as a catalyst for the aerobic oxidation of 5-hydroxymethylfurfural(HMF) to 2,5-diformylfuran(DFF) in acetic acid. Then, we systematically studied the important reaction parameters, including the solvent, co-catalyst, and temperature. The results demonstrate that the acidic solvent used is crucial for the efficient oxidation of HMF to DFF. Under optimal conditions, we achieved a 93.4% yield of DFF within half an hour at room temperature. We also proposed the possible mechanism for this system.
In this paper, we report a new catalytic system for realizing the rapid and efficient oxidation of 5-hydroxymethylfurfural(HMF). First, we used 9-azabicyclo [3.3.1]nonan-3-one-N-oxyl(keto-ABNO) as a catalyst for the aerobic oxidation of 5-hydroxymethylfurfural(HMF) to 2,5-diformylfuran(DFF) in acetic acid. Then, we systematically studied the important reaction parameters, including the solvent, co-catalyst, and temperature. The results demonstrate that the acidic solvent used is crucial for the efficient oxidation of HMF to DFF. Under optimal conditions, we achieved a 93.4% yield of DFF within half an hour at room temperature. We also proposed the possible mechanism for this system.
In this paper, we report a new catalytic system for realizing the rapid and efficient oxidation of 5-hydroxymethylfurfural(HMF). First, we used 9-azabicyclo [3.3.1]nonan-3-one-N-oxyl(keto-ABNO) as a catalyst for the aerobic oxidation of 5-hydroxymethylfurfural(HMF) to 2,5-diformylfuran(DFF) in acetic acid. Then, we systematically studied the important reaction parameters, including the solvent, co-catalyst, and temperature. The results demonstrate that the acidic solvent used is crucial for the efficient oxidation of HMF to DFF. Under optimal conditions, we achieved a 93.4% yield of DFF within half an hour at room temperature. We also proposed the possible mechanism for this system.
引文
1.Chheda JN,Huber GW,Dumesic JA(2007)Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals.Angew Chem Int Edit 46(38):7164-7183
2.Antonyraj CA,Jeong J,Kim B et al(2013)Selective oxidation of HMF to DFF using Ru/γ-alumina catalyst in moderate boiling solvents toward industrial production.J Ind Eng Chem19(3):1056-1059
3.Ventura M,Aresta M,Dibenedetto A(2016)Selective aerobic oxidation of 5-(hydroxymethyl)furfural to 5-formyl-2-furancarboxylic acid in water.ChemSusChem 9(10):1096-1100
4.Casanova O,Iborra S,Corma A(2009)Biomass into chemicals:aerobic oxidation of 5-hydroxymethyl-2-furfural into2,5-furandicarboxylic acid with gold nanoparticle catalysts.ChemSusChem2(12):1138-1144
5.Deng J,Song HJ,Cui MS et al(2014)Aerobic oxidation of hydroxymethylfurfural and furfural by using heterogeneous CoxOy-N@C catalysts.ChemSusChem 7(12):3334-3340
6.Sun Y,Ma H,Jia X et al(2016)A high-performance base-metal approach for the oxidative esterification of 5-hydroxymethylfurfural.ChemCatChem 8(18):2907-2911
7.Thananatthanachon T,Rauchfuss TB(2010)Efficient production of the liquid fuel2,5-dimethylfuran from fructose using formic acid as a reagent.Angew Chem Int Edit 49(37):6616-6618
8.Zu Y,Yang P,Wang J et al(2014)Efficient production of the liquid fuel2,5-dimethylfuran from 5-hydroxymethylfurfural over Ru/Co3O4 catalyst.Appl Catal B-Environ 146(3):244-248
9.Poeta MD,Schell WA,Dykstra CC et al(1998)Structure-In vitro activity relationships of pentamidine analogues and dication-substituted bis-benzimidazoles as new antifungal agents.Antimicrob Agents Chemother 42(10):2495-2502
10.Hopkins KT,Wilson WD,Bender BC et al(1999)Extended aromatic furan amidino derivatives as anti-pneumocystis carinii agents.J Med Chem 30(11):3872-3878
11.Moreau C,Belgacem MN,Gandini A(2004)Recent catalytic advances in the chemistry of substituted furans from carbohydrates and in the ensuing polymers.Top Catal 35(31):11-30
12.Richter DT,Lash TD(1999)Oxidation with dilute aqueous ferric chloride solutions greatly improves yields in the‘4+1’synthesis of sapphyrins.Tetrahedron Lett 40(37):6735-6738
13.Amarasekara AS,Green D,Williams LTD(2009)Renewable resources based polymers:synthesis and characterization of2,5-diformylfuran-urea resin.Eur Polym J 45(2):595-598
14.Ma J,Du Z,Xu J et al(2011)Efficient aerobic oxidation of5-hydroxymethylfurfural to2,5-diformylfuran,and synthesis of a fluorescent material.ChemSusChem 4(1):51-54
15.Xu F,Zhang Z(2015)Polyaniline-grafted VO(acac)2:an effective catalyst for the synthesis of2,5-difor mylfuran from 5-hydroxymethylfurfural and fructose.ChemCatChem7(9):1470-1477
16.Yang Z,Qi W,Su R et al(2017)3D flower-like micro/nano CeMo composite oxides as effective bifunctional catalysts for onepot conversion of fructose to2,5-diformylfuran.ACS Sustain Chem Eng 5(5):4179-4187
17.Le NT,Lakshmanan P,Cho K et al(2013)Selective oxidation of5-hydroxymethyl-2-furfural into2,5-diformylfuran over VO2+and Cu2+ions immobilized on sulfonated carbon catalysts.Appl Catal A-Gen 464-465(16):305-312
18.Liao L,Liu Y,Li Z et al(2016)Catalytic aerobic oxidation of5-hydroxymethylfurfural into2,5-diformylfuran over VO2+and Cu2+immobilized on amino-functionalized core-shell magnetic Fe 3 O 4@SiO2.RSC Adv 6(97):94976-94988
19.Fang R,Luque R,Li Y(2016)Selective aerobic oxidation of biomass-derived HMF to2,5-diformylfuran using a MOF-derived magnetic hollow Fe-Co nanocatalyst.Green Chem18(10):3152-3157
20.Wang Y,Liu B,Huang K et al(2016)Aerobic oxidation of biomass-derived 5-(hydroxymethyl)furfural into2,5-diformylfuran catalyzed by the trimetallic mixed oxide(Co-Ce-Ru).Ind Eng Chem Res 53(4):1313-1319
21.Liu B,Zhang Z,Lv K et al(2014)Efficient aerobic oxidation of biomass-derived 5-hydroxymethylfurfural to2,5-diformylfuran catalyzed by magnetic nanoparticle supported manganese oxide.Appl Catal A-Gen 472(3):64-71
22.Nie J,Xie J,Liu H(2013)Activated carbon-supported ruthenium as an efficient catalyst for selective aerobic oxidation of 5-hydroxymethylfurfural to2,5-diformylfuran.Chin J Catal 34(5):871-875
23.Wang F,Jiang L,Wang J et al(2016)Catalytic conversion of fructose and 5-hydroxymethylfurfural into2,5-diformylfuran over SBA-15 supported ruthenium catalyst.Energy Fuel30(7):5885-5892
24.Fang C,Dai JJ,Xu HJ et al(2015)Iron-catalyzed selective oxidation of 5-hydroxylmethylfurfural in air:a facile synthesis of2,5-diformylfuran at room temperature.Chin Chem Lett26(10):1265-1268
25.Mittal N,Nisola GM,Malihan LB et al(2014)Metal-free mild oxidation of 5-hydroxymethylfurfural to2,5-diformylfuran.Korean J Chem Eng 31(8):1362-1367
26.Lauber MB,Stahl SS(2013)Efficient aerobic oxidation of secondary alcohols at ambient temperature with an ABNO/NO x catalyst system.ACS Catal 3(11):2612-2616
27.Sever RR,Root TW(2003)DFT study of solvent coordination effects on titanium-based epoxidation catalysts.Part two:reactivity of titanium hydroperoxo complexes in ethylene epoxidation.JPhys Chem B 107(17):4090-4099
28.Ma S,Liu J,Li S et al(2011)Development of a general and practical iron nitrate/TEMPO-catalyzed aerobic oxidation of alcohols to aldehydes/ketones:catalysis with table salt.Adv Synth Catal353(6):1005-1017
29.Dijksman A,Arends IW,Sheldon RA(2003)Cu(Ⅱ)-nitroxyl radicals as catalytic galactose oxidase mimics.Org Biomol Chem1(18):3232-3237
30.Liu R,Liang X,Dong C et al(2004)Transition-metal-free:a highly efficient catalytic aerobic alcohol oxidation process.J Am Chem Soc 35(32):4112-4113
2.Antonyraj CA,Jeong J,Kim B et al(2013)Selective oxidation of HMF to DFF using Ru/γ-alumina catalyst in moderate boiling solvents toward industrial production.J Ind Eng Chem19(3):1056-1059
3.Ventura M,Aresta M,Dibenedetto A(2016)Selective aerobic oxidation of 5-(hydroxymethyl)furfural to 5-formyl-2-furancarboxylic acid in water.ChemSusChem 9(10):1096-1100
4.Casanova O,Iborra S,Corma A(2009)Biomass into chemicals:aerobic oxidation of 5-hydroxymethyl-2-furfural into2,5-furandicarboxylic acid with gold nanoparticle catalysts.ChemSusChem2(12):1138-1144
5.Deng J,Song HJ,Cui MS et al(2014)Aerobic oxidation of hydroxymethylfurfural and furfural by using heterogeneous CoxOy-N@C catalysts.ChemSusChem 7(12):3334-3340
6.Sun Y,Ma H,Jia X et al(2016)A high-performance base-metal approach for the oxidative esterification of 5-hydroxymethylfurfural.ChemCatChem 8(18):2907-2911
7.Thananatthanachon T,Rauchfuss TB(2010)Efficient production of the liquid fuel2,5-dimethylfuran from fructose using formic acid as a reagent.Angew Chem Int Edit 49(37):6616-6618
8.Zu Y,Yang P,Wang J et al(2014)Efficient production of the liquid fuel2,5-dimethylfuran from 5-hydroxymethylfurfural over Ru/Co3O4 catalyst.Appl Catal B-Environ 146(3):244-248
9.Poeta MD,Schell WA,Dykstra CC et al(1998)Structure-In vitro activity relationships of pentamidine analogues and dication-substituted bis-benzimidazoles as new antifungal agents.Antimicrob Agents Chemother 42(10):2495-2502
10.Hopkins KT,Wilson WD,Bender BC et al(1999)Extended aromatic furan amidino derivatives as anti-pneumocystis carinii agents.J Med Chem 30(11):3872-3878
11.Moreau C,Belgacem MN,Gandini A(2004)Recent catalytic advances in the chemistry of substituted furans from carbohydrates and in the ensuing polymers.Top Catal 35(31):11-30
12.Richter DT,Lash TD(1999)Oxidation with dilute aqueous ferric chloride solutions greatly improves yields in the‘4+1’synthesis of sapphyrins.Tetrahedron Lett 40(37):6735-6738
13.Amarasekara AS,Green D,Williams LTD(2009)Renewable resources based polymers:synthesis and characterization of2,5-diformylfuran-urea resin.Eur Polym J 45(2):595-598
14.Ma J,Du Z,Xu J et al(2011)Efficient aerobic oxidation of5-hydroxymethylfurfural to2,5-diformylfuran,and synthesis of a fluorescent material.ChemSusChem 4(1):51-54
15.Xu F,Zhang Z(2015)Polyaniline-grafted VO(acac)2:an effective catalyst for the synthesis of2,5-difor mylfuran from 5-hydroxymethylfurfural and fructose.ChemCatChem7(9):1470-1477
16.Yang Z,Qi W,Su R et al(2017)3D flower-like micro/nano CeMo composite oxides as effective bifunctional catalysts for onepot conversion of fructose to2,5-diformylfuran.ACS Sustain Chem Eng 5(5):4179-4187
17.Le NT,Lakshmanan P,Cho K et al(2013)Selective oxidation of5-hydroxymethyl-2-furfural into2,5-diformylfuran over VO2+and Cu2+ions immobilized on sulfonated carbon catalysts.Appl Catal A-Gen 464-465(16):305-312
18.Liao L,Liu Y,Li Z et al(2016)Catalytic aerobic oxidation of5-hydroxymethylfurfural into2,5-diformylfuran over VO2+and Cu2+immobilized on amino-functionalized core-shell magnetic Fe 3 O 4@SiO2.RSC Adv 6(97):94976-94988
19.Fang R,Luque R,Li Y(2016)Selective aerobic oxidation of biomass-derived HMF to2,5-diformylfuran using a MOF-derived magnetic hollow Fe-Co nanocatalyst.Green Chem18(10):3152-3157
20.Wang Y,Liu B,Huang K et al(2016)Aerobic oxidation of biomass-derived 5-(hydroxymethyl)furfural into2,5-diformylfuran catalyzed by the trimetallic mixed oxide(Co-Ce-Ru).Ind Eng Chem Res 53(4):1313-1319
21.Liu B,Zhang Z,Lv K et al(2014)Efficient aerobic oxidation of biomass-derived 5-hydroxymethylfurfural to2,5-diformylfuran catalyzed by magnetic nanoparticle supported manganese oxide.Appl Catal A-Gen 472(3):64-71
22.Nie J,Xie J,Liu H(2013)Activated carbon-supported ruthenium as an efficient catalyst for selective aerobic oxidation of 5-hydroxymethylfurfural to2,5-diformylfuran.Chin J Catal 34(5):871-875
23.Wang F,Jiang L,Wang J et al(2016)Catalytic conversion of fructose and 5-hydroxymethylfurfural into2,5-diformylfuran over SBA-15 supported ruthenium catalyst.Energy Fuel30(7):5885-5892
24.Fang C,Dai JJ,Xu HJ et al(2015)Iron-catalyzed selective oxidation of 5-hydroxylmethylfurfural in air:a facile synthesis of2,5-diformylfuran at room temperature.Chin Chem Lett26(10):1265-1268
25.Mittal N,Nisola GM,Malihan LB et al(2014)Metal-free mild oxidation of 5-hydroxymethylfurfural to2,5-diformylfuran.Korean J Chem Eng 31(8):1362-1367
26.Lauber MB,Stahl SS(2013)Efficient aerobic oxidation of secondary alcohols at ambient temperature with an ABNO/NO x catalyst system.ACS Catal 3(11):2612-2616
27.Sever RR,Root TW(2003)DFT study of solvent coordination effects on titanium-based epoxidation catalysts.Part two:reactivity of titanium hydroperoxo complexes in ethylene epoxidation.JPhys Chem B 107(17):4090-4099
28.Ma S,Liu J,Li S et al(2011)Development of a general and practical iron nitrate/TEMPO-catalyzed aerobic oxidation of alcohols to aldehydes/ketones:catalysis with table salt.Adv Synth Catal353(6):1005-1017
29.Dijksman A,Arends IW,Sheldon RA(2003)Cu(Ⅱ)-nitroxyl radicals as catalytic galactose oxidase mimics.Org Biomol Chem1(18):3232-3237
30.Liu R,Liang X,Dong C et al(2004)Transition-metal-free:a highly efficient catalytic aerobic alcohol oxidation process.J Am Chem Soc 35(32):4112-4113