Switchable synthesis of 2,5-dimethylfuran and 2,5-dihydroxymethyltetrahydrofuran from 5-hydroxymethylfurfural over Raney Ni catalyst

Kong, Xiao; Zhu, Yulong; Zheng, Hongyan; Dong, Fang; Zhu, Yulei; Li, Yongwang

doi:10.1039/c4ra09550b

Cited by 110 publications

(90 citation statements)

References 35 publications

(43 reference statements)

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“…20 Besides, 2,5-HeD was formed over NiAl-850 and NiAl-750 catalysts. Among the catalysts, NiAl-850 exhibited the highest DMF yield of ~91.5% while NiAl-300 showed the lowest DMF yield of ~44.6%.…”

Section: Synthesis Of Dmf By Hmf Hydrogenationmentioning

confidence: 93%

“…9 After this work, studies Scheme 1 Hydrogenation of HMF to various products. In our previous work 20 , a switchable synthesis of DMF and DHMTHF was achieved with high yield respectively over Raney Ni, demonstrating high feasibility of Ni-based catalyst. However, the availability and high price greatly hindered the commercial applications of noble metals.…”

Section: Introductionmentioning

confidence: 89%

“…DHMF and 5-methylfurfuryl alcohol (MFA) are the key intermediates for this reaction. 20 HMF was totally converted over all the catalysts after 4 h, indicating the high reactivity of non-noble NiAl-CT catalysts. Table 2 presents the catalytic performance of NiAl-CT catalysts for DMF synthesis.…”

Section: Synthesis Of Dmf By Hmf Hydrogenationmentioning

confidence: 94%

“…20 The excessive conversion of DMF would generate some byproducts including DMTHF and 2,5-hexanedione (2,5-HeD). DHMF and 5-methylfurfuryl alcohol (MFA) are the key intermediates for this reaction.…”

Section: Synthesis Of Dmf By Hmf Hydrogenationmentioning

confidence: 99%

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Rational design of Ni-based catalysts derived from hydrotalcite for selective hydrogenation of 5-hydroxymethylfurfural

et al. 2015

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ARTICLE This journal isSelective hydrogenation of 5-hydroxymethylfurfural (HMF) is of great importance for future energy and chemical supply. Herein, we propose for the first time that non-noble Ni-Al 2 O 3 catalysts derived from hydrotalcite-like compounds can efficiently and selectively convert HMF to 2,5-dimethylfuran (DMF), 2,5-dimethyltetrahydrofuran (DMTHF) and 2,5dihydroxymethyltetrahydrofuran (DHMTHF). Homogeneous elemental distributions of hydrotalcite-like precursor facilitate the good dispersion of Ni and Al 2 O 3 species and strong interaction between them over the resulted catalysts. The catalysts therefore exhibited superior reactivity. Through fine modulation of surface metal-acid bifunctional sites and control of reaction conditions, high yields of DMF (91.5%), DMTHF (97.4%) and DHMTHF (96.2%) can be diversely achieved. The results demonstrate the feasibility of Ni catalysts for selective hydrogenation of C=O, C=C and C-O bonds, which have great potential for biomass utilization. ARTICLEThis journal is © The Royal Society of Chemistry 2015Green Chem., 2015, 00, 1-3 | 9 TPD) and CO temperature programmed desorption (CO-TPD) were performed on a Tianjin XQ TP-5080 instrument. Temperature programmed desorption of NH 3 (NH 3 -TPD) experiments were conducted on the AutoChem II. 2920 instrument (Micromeritics, USA) equipped with a mass spectrum detector. (See supporting information for details about the characterizations). Catalyst tests:The tests were performed over a 100 mL tank reactor. For a typical procedure, the reactor was fed with HMF (1.5 g), NiAl-CT and 1,4-dioxane (35 mL), then sealed and purged by H 2 (5 times). After that, the reactor was filled with H 2 in desired pressure and heated to objective temperature. After the test, the reactor was quenched in icewater, and then the liquid and gas products were analysed by a GC instrument with a FID detector. Notes and references

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Section: Synthesis Of Dmf By Hmf Hydrogenationmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 89%

Section: Synthesis Of Dmf By Hmf Hydrogenationmentioning

confidence: 94%

Section: Synthesis Of Dmf By Hmf Hydrogenationmentioning

confidence: 99%

See 2 more Smart Citations

Rational design of Ni-based catalysts derived from hydrotalcite for selective hydrogenation of 5-hydroxymethylfurfural

et al. 2015

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“…11,17,[22][23][24][25][26]28 RANEY®-type metals (Cu, Co and Ni) have been investigated as catalyst for total hydrogenation of HMF using 1,4-dioxane as solvent by Kong et al 25 Among the RANEY®-type metals, RANEY® Ni was revealed to be the most selective with a 96% DHMTHF selectivity at full conversion, at 100 C and 15 bar of H 2 aer 15 h of reaction. 25 RANEY® Ni has also been successfully used to catalyse the hydrogenation of HMF into DHMTHF in other solvents such as methanol or ethanol with yields higher than 95%. 11,26 The best result was reported by Connolly et al using methanol as solvent, achieving 99% selectivity to DHMTHF and over 95% HMF conversion under relatively mild reaction conditions, 60 C under 4.8 bar of H 2 aer 4 h of batch operation.…”

Section: -22mentioning

confidence: 99%

Towards sustainable hydrogenation of 5-(hydroxymethyl)furfural: a two-stage continuous process in aqueous media over RANEY® catalysts

2017

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The hydrogenation of 5-(hydroxymethyl)furfural (HMF) to 2,5-bis(hydroxymethyl)tetrahydrofuran (DHMTHF) in aqueous media under relatively mild reaction conditions has been investigated over heterogeneous RANEY® Cu and Ni catalysts using a continuous-flow hydrogenation reactor. These RANEY® catalysts were selected following a screening of several catalysts including precious metals supported on carbon for the hydrogenation of HMF. A single-stage versus a two-stage process for the hydrogenation of HMF into DHMTHF, i.e. via 2,5-dihydroxymethylfuran (DHMF) has been evaluated. The best result with an average selectivity of 98% for DHMTHF was obtained using a two-stage process; RANEY® Cu was used as a catalyst for the highly selective hydrogenation of HMF to DHMF (92 mol%) in the first stage and this product was used without further purification for in a second-stage selective hydrogenation of DHMF into DHMTHF using RANEY® Ni as a catalyst. The influence of the HMF concentration in the feeding solution (1-3 wt%), flow rate (0.05-0.25 mL min À1) and total pressure (20-90 bar) were investigated for the first-stage hydrogenation of HMF into DHMF over RANEY® Cu. HMF was found to exert an inhibiting effect on the conversion due to strong adsorption. The RANEY® Ni catalyst used in the second stage gradually deactivated. A procedure for in situ regeneration of the partially deactivated RANEY® Ni catalyst using acetic acid washing was investigated with limited success.

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Conversion of Lignocellulosic Biomass to Biofuels

García‐Sancho

Cecilia

Luque

2021

Heterogeneous Catalysts

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Switchable synthesis of 2,5-dimethylfuran and 2,5-dihydroxymethyltetrahydrofuran from 5-hydroxymethylfurfural over Raney Ni catalyst

Abstract: Switchable synthesis of 2,5-dimethylfuran and 2,5-dihydroxymethyltetrahydrofuran was achieved over Raney Ni catalyst, which has high feasibility in industry.

Cited by 110 publications

References 35 publications

Rational design of Ni-based catalysts derived from hydrotalcite for selective hydrogenation of 5-hydroxymethylfurfural

Rational design of Ni-based catalysts derived from hydrotalcite for selective hydrogenation of 5-hydroxymethylfurfural

Towards sustainable hydrogenation of 5-(hydroxymethyl)furfural: a two-stage continuous process in aqueous media over RANEY® catalysts

Conversion of Lignocellulosic Biomass to Biofuels

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