Cu catalyzed oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran and 2,5-furandicarboxylic acid under benign reaction conditions

Hansen, Thomas; Sádaba, Irantzu; García-Suárez, Eduardo J.; Riisager, Anders

doi:10.1016/j.apcata.2013.01.042

Cited by 127 publications

(87 citation statements)

References 31 publications

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“…As listed in Table 5, phenol, anhydride, and anthraquinone exhibited negligible HMF conversions in the selective oxidation of HMF ( (Table 5, entry [5][6][7][8][9]. This result demonstrated that the carboxylic acid -TEMPO system own the intrinsic activity in aerobic oxidation of alcohols.…”

Section: Probing the Origin Of Catalytic Activity In Gomentioning

confidence: 94%

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Graphene Oxide: A Convenient Metal-Free Carbocatalyst for Facilitating Aerobic Oxidation of 5-Hydroxymethylfurfural into 2, 5-Diformylfuran

Wang²,

Yang³

et al. 2015

ACS Catal.

155

107

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By thermal treatment in vacuum, graphite oxide prepared from Hummers' method was exfoliated and partially reduced. This procedure imparts the graphene oxide (GO) the high reactivity with 2,2,6,6-tetramethyl-piperidin-1-oxyl (TEMPO) as co-catalyst for selective oxidation of 5-hydroxymethylfrufural (HMF) to 2, 5-diformylfuran (DFF) under certain conditions (100% HMF conversion with HMF selectivity 99.6% at 80 wt.% GO loading, 1 atm air pressure). This study found that GO could function as an oxidant for anaerobic oxidation of HMF during which carboxyl groups in GO were reduced. Importantly, the partially reduced GO material could continue activate molecular oxygen during aerobic oxidation. Further study showed that oxygen functionalities in GO material had a crucial effect on the catalytic oxidation of HMF.By control experiments and molecular analogues tests, a plausible mechanism was proposed in which the high reactivity was attributed to the synergistic effect of the carboxylic acid groups and unpaired electrons at GO edge defects, with TEMPO as the co-catalyst and oxygen as the terminal oxidant.

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Section: Probing the Origin Of Catalytic Activity In Gomentioning

confidence: 94%

“…TEMPO) has always been used as the co-catalyst for the generation of aldehydes or ketones from alcohols. CuCl/TEMPO/NCPs catalytic system was successfully applied in the oxidation of HMF into DFF 9. When TEMPO, which is not active as a catalystTable 1Oxidation of HMF into DFF over GO under different conditions a…”

mentioning

confidence: 99%

Graphene Oxide: A Convenient Metal-Free Carbocatalyst for Facilitating Aerobic Oxidation of 5-Hydroxymethylfurfural into 2, 5-Diformylfuran

Wang²,

Yang³

et al. 2015

ACS Catal.

155

107

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“…However, the presence of the base can lead to a gradual degradation of HMF [32,[42][43][44]. Other reports claim a high selectivity to FDCA without the addition of any base, [45,46] when TBHP is used as oxidizing agent and CuCl 2 as catalyst (selectivity of 48% after 48 h [46]). …”

Section: Introductionmentioning

confidence: 95%

Selective oxidation of 5-hydroxymethyl furfural over non-precious metal heterogeneous catalysts

Neaţu

Marin

Florea

et al. 2016

Applied Catalysis B: Environmental

115

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“…Recently, there has been growing attention on the synthesis of DFF from HMF oxidation using molecular oxygen as the terminal oxidant, as catalyzed by heterogeneous or homogeneous metal catalysts, such as Ru, Cu, Mn, Mo/V, and V . These catalysts often produce relatively low yields of DFF and the transition‐metal‐based catalysts are often expensive, toxic, and frequently obtained from limited natural resources .…”

Section: Introductionmentioning

confidence: 99%

Benzoic Acid/TEMPO as a Highly Efficient Metal‐Free Catalyst System for Selective Oxidation of 5‐hydroxymethylfurfural into 2, 5‐diformylfuran

et al. 2017

Energy Tech

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The combination of benzoic acid and 2,2,6,6‐teramethylpiperidin‐1‐oxyl (TEMPO) afforded an efficient catalytic system for the aerobic oxidation of 5‐hydroxymethylfurfural (HMF) into 2,5‐diformylfuran (DFF) under certain conditions. The maximum conversion of 86.7 % for HMF was obtained with a nearly 77.8 % DFF yield at 1 mmol benzoic acid and 0.4 MPa oxygen pressure in acetonitrile. The aerobic oxidation ability of HMF into DFF depended on the electron density of the organic acid skeletal structure with the carboxyl group. Meanwhile, the catalyst system of benzoic acid/TEMPO also exhibited good performance for aerobic oxidation of other alcohols. Based on experimental results, we propose that the benzoic acid acted as the primary catalyst and TEMPO was the key co‐catalyst, oxidized into oxoammonium cation through electron transport and then regenerated by a superoxide radical during the reaction.

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Cu catalyzed oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran and 2,5-furandicarboxylic acid under benign reaction conditions

Cited by 127 publications

References 31 publications

Graphene Oxide: A Convenient Metal-Free Carbocatalyst for Facilitating Aerobic Oxidation of 5-Hydroxymethylfurfural into 2, 5-Diformylfuran

Graphene Oxide: A Convenient Metal-Free Carbocatalyst for Facilitating Aerobic Oxidation of 5-Hydroxymethylfurfural into 2, 5-Diformylfuran

Selective oxidation of 5-hydroxymethyl furfural over non-precious metal heterogeneous catalysts

Benzoic Acid/TEMPO as a Highly Efficient Metal‐Free Catalyst System for Selective Oxidation of 5‐hydroxymethylfurfural into 2, 5‐diformylfuran

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