N-doped carbon layer-coated Au nanocatalyst for H2-free conversion of 5-hydroxymethylfurfural to 5-methylfurfural

doi:10.1016/S1872-2067(21)64049-4

Abstract

Abstract:

Deoxygenative upgrading of 5-hydromethylfurfural (HMF) into valuable chemicals has attracted intensive research interest in recent years, with product selectivity control remaining an important topic. Herein, TiO₂ supported gold catalysts coated with a thin N-doped porous carbon (NPC) layer were developed via a polydopamine-coating-carbonization strategy and utilized for pathway-specific conversion of HMF into 5-methylfurfural (5-MF) with the use of renewable formic acid (FA) as the deoxygenation reagent. The as-fabricated Au/TiO₂@NPC exhibited excellent catalytic performance with a high yield of 5-MF (>95%). The catalytic behavior of Au@NPC-based catalysts was shown to be correlated with the suitable combination of highly dispersed Au nanoparticles and favorable interfacial interactions in the Au@NPC core-shell hetero-nanoarchitectures, thereby facilitating the preferential esterification of HMF with FA and suppressing unproductive FA dehydrogenation, which promoted the selective formylation/decarboxylation of hydroxy-methyl group in HMF in a pathway-specific manner. The present NPC/metal interfacial engineering strategy may provide a potential guide for the rational design of advanced catalysts for a wide variety of heterogeneous catalysis processes in terms of the conversion of biomass source.

Key words: 5-Hydroxymethylfurfural, 5-Methylfurfural, Gold catalysis, N-doped porous carbon, Biomass upgrading

Jiang Zhang, Zijian Wang, Mugeng Chen, Yifeng Zhu, Yongmei Liu, Heyong He, Yong Cao, Xinhe Bao. N-doped carbon layer-coated Au nanocatalyst for H₂-free conversion of 5-hydroxymethylfurfural to 5-methylfurfural[J]. Chinese Journal of Catalysis, 2022, 43(8): 2212-2222.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)64049-4

https://www.cjcatal.com/EN/Y2022/V43/I8/2212

Figures/Tables 11

Scheme 1. Production of bio-based chemicals or fuels by 5-MF or HMF [14].

Scheme 2. Routes for 5-MF synthesis.

Scheme 3. Schematic illustration of the synthesis procedure of Au-n/TiO2@NPC-T.

Fig. 1. (a) TEM image and particle size distribution; HRTEM images (b,c), HAADF-STEM images and corresponding EDX elemental mapping (d) of Au-4/TiO2@NPC.

Fig. 2. CO-DRIFT spectra (a) as well as XPS in the Au 4f (b) and N 1s (c) region of Au-4/TiO2@NPC-T. (1) Au-4/TiO2@NPC-500; (2) Au-4/TiO2@NPC; (3) Au-4/TiO2@NPC-700; (4) Au-4/TiO2@NPC-800.

Table 1 FA-mediated catalytic conversion of HMF into 5-MF using various catalysts.

Entry	Catalysts	Carbon balance (%)	Conversion (%)	Yield (%)
Entry	Catalysts	Carbon balance (%)	Conversion (%)	1	2	3	4	5	others
1	Au/TiO₂-4	>99	>99	—	31	34	—	35	—
2	Au-4/TiO₂@NPC	>99	>99	—	95	—	—	5	—
3 ^a	Au-4/TiO₂@NPC	>99	>99	—	90	—	—	9	1
4 ^b	Au-4/TiO₂@NPC	>99	>99	2	92	—	—	6	—
5	Au_em/TiO₂@NPC	>99	>99	—	81	—	—	19	—
6	Au-4/TiO₂@NPC(5%)	>99	>99	—	90	—	—	10	—
7	Au-4/TiO₂@NPC(15%)	>99	94	6	85	—	2	1	—
8	Au-4/TiO₂@NPC-500	>99	>99	9	89	—	—	2	—
9	Au-4/TiO₂@NPC-700	>99	>99	4	90	—	—	6	—
10	Au-4/TiO₂@NPC-800	>99	>99	—	87	—	—	13	—
11	Au-2/TiO₂@NPC-600	>99	>99	—	89	—	—	11	—
12	Au-3/TiO₂@NPC-600	>99	>99	—	91	—	—	9	—
13	Au-5/TiO₂@NPC-600	>99	99	4	93	—	—	2	—

Fig. 3. (a) Reuse of Au-4/TiO2@NPC in the HMF-to-5-MF transformation (reaction time 10 min). (b) TEM image and particle size distribution of Au-4/TiO2@NPC after reused six times; XPS characterization of Au 4f (c) and CO-DRIFT spectra (d) of Au-4/TiO2@NPC before and after reaction.

Fig. 4. TEM images of Auem/TiO2@NPC.

Fig. 5. Reaction progress of FA-mediated HMF conversion to 5-MF. (a) Time course plot. (b) Reaction network for FA-mediated HMF conversion to 5-MF. Reaction conditions: 1 mmol HMF, 4 mmol FA, Au-4/TiO2@NPC 0.4 mol%, 0.1 MPa N2, 10 mL 1,4-dioxane, 180 °C. Note: HFF: 2-hydroxy-5-fururfylformate, 5-MFF: 5-methylfururfylformate.

Fig. 6. FMF decomposition and FA decomposition over various catalysts. Reaction conditions: 1 mmol substrate, catalyst 0.04 mol%, 0.1 MPa N2, 10 mL 1,4-dioxane, 180 °C, TOF values based on 15% conversion of substrate.

Table 2 FA-mediated hydrodeoxygenation of different substrates over the Au-4/TiO2@NPC catalyst.

Entry	Time (h)	FA (mmol)
1	1.5	4	>99	94
2	1.5	4	>99	92
3	1.5	4	>99	96
4	3	8	>99	93
5	1.5	4	>99	99
6	2.5	4	>99	97
7	1.5	4	trace	trace
8	1.5	4	trace	trace

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N-doped carbon layer-coated Au nanocatalyst for H₂-free conversion of 5-hydroxymethylfurfural to 5-methylfurfural

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