Oxidation of 2,5-bis(hydroxymethyl)furan to 2,5-furandicarboxylic acid catalyzed by carbon nanotube-supported Pd catalysts

doi:10.1016/S1872-2067(21)63878-0

Abstract

Abstract:

The selective oxidation of 2,5-bis(hydroxymethyl)furan (BHMF) in this work was proven as a promising route to produce 2,5-furandicarboxylic acid (FDCA), an emerging bio-based building-block with wide application. Under ambient pressure, the modified carbon nanotube-supported Pd-based catalysts demonstrate the maximum FDCA yield of 93.0% with a full conversion of BHMF after 60 min at 60 °C, much superior to that of the traditional route using 5-hydroxymethylfurfural (HMF) as substrates (only a yield of 35.7%). The participation of PdH_x active species with metallic Pd can be responsible for the encouraging performance. Meanwhile, a possible reaction pathway proceeding through 2,5-diformylfuran (DFF) and 5-formyl-2-furancarboxylic acid (FFCA) as process intermediates is suggested for BHMF route. The present work may provide new opportunities to synthesize other high value-added oxygenates by using BHMF as an alternative feedstock.

Key words: 2,5-Bis(hydroxymethyl)furan, 2,5-Furandicarboxylic acid, Palladium hydride, 5-Hydroxymethylfurfural, Catalytic oxidation

Zhenyu Li, Liyuan Huai, Panpan Hao, Xi Zhao, Yongzhao Wang, Bingsen Zhang, Chunlin Chen, Jian Zhang. Oxidation of 2,5-bis(hydroxymethyl)furan to 2,5-furandicarboxylic acid catalyzed by carbon nanotube-supported Pd catalysts[J]. Chinese Journal of Catalysis, 2022, 43(3): 793-801.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63878-0

https://www.cjcatal.com/EN/Y2022/V43/I3/793

Figures/Tables 8

Fig. 1. The time courses of normalized substrate concentrations. Reaction condition: No catalysts, substrate 20 mM, H2O 30 mL, NaOH/substrate (molar ratio) 10/1, 60 °C, 60 min.

Fig. 2. Effects of the pretreatment of CNTs on catalytic behaviors of the Pd/CNT catalysts for BHMF oxidation. Notably, the Pd/CNT sample with CNTs pretreated by 30 wt% HNO3 is specified as Pd/o-CNT in the main text. Reaction conditions: BHMF 20 mM, BHMF/Pd (molar ratio) 50/1, H2O 30 mL, NaOH/BHMF (molar ratio) 10/1, 60 °C, 100 ml/min O2, 60 min.

Table 1 Physicochemical properties and catalytic performances of carbon nanotube-supported Pd catalysts for BHMF oxidation. a

Entry	Catalyst	Pd loading ^b (wt %)	Mean particle size ^c (nm)	S(PdH_x)/S(Pd⁰) ^d	I_D/I_G ratio ^e	BHMF conv. (%)	Yield (%)
Entry	Catalyst	Pd loading ^b (wt %)	Mean particle size ^c (nm)	S(PdH_x)/S(Pd⁰) ^d	I_D/I_G ratio ^e	BHMF conv. (%)	FDCA	HMFCA	FFCA	HMF
1	Pd/CNT	4.7	4.0	2.0	1.22	>99	71.0	13.2	12.0	0.2
2	Pd/o-CNT	4.8	4.2	4.4	1.22	>99	93.0	4.8	0	0
3	Pd/o-CNT-10runs	4.1	6.7	3.2	—	>99	75.1	24.4	0	0

Fig. 3. TEM images and the corresponding particle size distributions of Pd/CNT (a,b) and Pd/o-CNT (c,d).

Fig. 4. Raman spectra (a), XRD pattern (b), TPDMS profile (c) and XPS Pd 3d spectra (d) for Pd/CNT and Pd/o-CNT.

Fig. 5. (a) Stability of the Pd/o-CNT catalyst during the recycling uses for BHMF oxidation. Reaction conditions: BHMF 20 mM, BHMF/Pd (molar ratio) 50/1, H2O 30 mL, NaOH/BHMF (molar ratio) 10/1, 60 °C, 100 ml/min O2, 60 min. TEM image (b), XRD pattern (c) and XPS Pd 3d spectra (d) for the spent Pd/o-CNT-10runs catalyst.

Fig. 6. The time courses for the oxidation of BHMF (a) and HMF (b) over Pd/o-CNT under a NaOH/substrate molar ratio of 10:1. Effect of the base concentration on catalytic behavior of the Pd/o-CNT catalyst for the oxidation of BHMF (c) and HMF (d). Reaction conditions: substrate 20 mM, substrate/Pd (molar ratio) 50/1, H2O 30 mL, 60 °C, 100 ml/min O2, 60 min.

Fig. 7. (a) The proposed reaction pathway for BHMF oxidation over the Pd/o-CNT catalyst. The time courses for the oxidation of DFF (b) and FFCA (c) over Pd/o-CNT. Reaction conditions: substrate 20 mM, substrate/Pd (molar ratio) 50/1, H2O 30 mL, 60 °C, 100 ml/min O2, 60 min.

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