Support Screening Studies on the Hydrogenation of Levulinic Acid to γ-Valerolactone in Water Using Ru Catalysts
Abstract
:1. Introduction
2. Results and Discussion
2.1. Catalyst Characterization
2.2. Catalytic LA Hydrogenation Experiments
2.3. LA Hydrogenation with a Bimetallic Catalyst
2.4. Comparison of Activity of the Catalyst with Literature Data
2.5. Catalyst Structure-Activity Relations
2.6. Catalyst Structure-Selectivity Relations
3. Experimental Section
3.1. Materials
3.2. Catalysts Preparation
3.3. Analysis
3.4. Catalytic Hydrogenation Experiments of LA
3.5. Definitions
3.6. Determination of the Concentrations of LA, GVL and 4-HPA
3.7. Determination of the Initial Rates
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Catalyst | Additives | Solvent | T (°C) | H2 (Bar) | Time (h) | LA Conversion (%) | GVL Selectivity(%) | Reference |
---|---|---|---|---|---|---|---|---|
Ru/C (5 wt. % Ru) | - | dioxane | 150 | 55 | 2 | 80 | 92 | [5] |
Ru/C (5 wt. % Ru) | - | H2O | 130 | 12 | 2.7 | 99.5 | 86.6 | [6] |
methanol | 99 | 85 | ||||||
ethanol | 76 | 81 | ||||||
1-butanol | 49 | 82 | ||||||
dioxane | 99 | 98 | ||||||
methanol + H2O | 96 | 88 | ||||||
ethanol + H2O | 99 | 90 | ||||||
butanol + H2O | 99 | 76 | ||||||
Ru/C (3 wt. % Ru) | - | H2O | 90 | 45 | 1 | 100 | 98 | [8] |
Ru0.9Ni0.1/OMC (0.56 wt. % Ru 0.08 wt. % Ni) | - | H2O | 150 | 45 | 2 | 99 | 97 | [9] |
Ru/C (5 wt. % Ru) | - | H2O | 180 | 30 | 12 | 100 | 57 | [10] |
Ru/C (5 wt. % Ru) | - | H2O (0.08 wt. %) | 130 | 20.6 | 49.5 | 51 | >99 | [11] |
Ru/C (5 wt. % Ru) | - | H2O | 70 | 30 | 3 | 48 | 98 | [12] |
A 70 a | 100 | 99 | ||||||
Ru/C (5 wt. % Ru) | - | methanol | 130 | 12 | 2.7 | 92 | 99 | [13] |
Ru/C (5 wt. % Ru) | - | methanol | 130 | 12 | 2.7 | 93 | 99 | [14] |
1-butanol | 0 | 0 | ||||||
benzaldehyde | 0 | 0 | ||||||
DMSO | 0 | 0 | ||||||
dioxane | 4 | 0 | ||||||
Ru/Starbon (5 wt. % Ru) | - | ethanol + H2O | 100 | 10 | 2.2 | >99 | <5 | [15] |
Ru/C, (5 wt. % Ru) | [BMIm-SH] [HSO4] | methanol | 130 | 34.5 | 2 | 99 | 68 | [16] |
A 15 | 99 | 14 | ||||||
SO4-ZrO2 | 99 | 18 |
Catalyst | Additives | Solvent | T (°C) | H2 (Bar) | Time (h) | LA Conversion (%) | GVL Selectivity (%) | Reference |
---|---|---|---|---|---|---|---|---|
Ru/SiO2 (5 wt. % Ru) | - | ethanol | 130 | 12 | 2.7 | 83 | 93 | [6] |
ethanol + H2O | 98 | 77 | ||||||
Ru/Al2O3 (5 wt. % Ru) | - | ethanol | 130 | 12 | 2.7 | 38 | 86 | [6] |
ethanol + H2O | 95 | 80 | ||||||
Ru/TiO2 (Rutile) (5 wt. % Ru) | ethanol | 130 | 12 | 2.7 | 0 | - | [6] | |
ethanol + H2O | 0 | - | ||||||
Ru/TiO2 (P25) (5 wt. % Ru) | ethanol | 130 | 12 | 2.7 | 68 | 92 | [6] | |
ethanol + H2O | 81 | 88 | ||||||
Ru/TiO2 (1 wt. % Ru) | - | H2O | 70 | 50 | 1 | 99 | 95 | [7] |
THF | 0 | 0 | ||||||
Ru/Nb2O5 (1 wt. % Ru) | - | dioxane | 200 | 40 | 4 | 72 | 86 | [26] |
Ru/TiO2 (1 wt. % Ru) | - | dioxane | 200 | 40 | 4 | 100 | 92 | [26] |
Ru/Beta-12.5 (1 wt. % Ru) | - | dioxane | 200 | 40 | 4 | 100 | 60 | [26] |
Ru/H-ZSM-5-11.5 (1 wt. % Ru) | - | dioxane | 200 | 40 | 10 | 100 | 70 | [27] |
Ru/Al2O3 (5 wt. % Ru) | - | H2O | 70 | 30 | 3 | 24 | 96 | [12] |
A 70 | 57 | 98 | ||||||
Ru/SiO2 (5 wt. % Ru) | scCO2 | H2O | 200 | 100 | n.a. a | 98 | > 99 | [28] |
Ru/Al2O3 (5 wt. % Ru) | scCO2 | - | 150 | 145 | n.a. a | 99 | 99 | [29] |
RuPd/TiO2 (1 wt. % Ru) | - | dioxane | 200 | 40 | 0.5 | 99 | 99 | [30] |
Ru/hydroxyapatite (5 wt. % Ru) | - | H2O | 70 | 5 | 4 | 99 | 99 | [31] |
ethanol | 92 | 76 | ||||||
ethanol + H2O | 92 | 82 | ||||||
toluene | 30 | 92 | ||||||
Ru/SPES (polyethersulfone) (2 wt. % Ru) | - | H2O | 70 | 30 | 2 | 88 | 99 | [32] |
Catalyst | Actual Ru Content (wt.%) b | Total Acidity (μmol/gcat) | Type of Acid Sites | Average Ru Particle Size (TEM), (nm) | Specific Surface Area (m2/g) | Micropore Surface Area (m2/g) |
---|---|---|---|---|---|---|
Ru/Beta-12.5 | 0.97 | 1070 | weak and medium | 3.5 | 515 | 329 |
Ru/CNT | n.d. c | 46 | strong | 1.1 | 272 | 14 |
Ru/C | 1 d | 99 | medium | 0.9 | 911 | 487 |
Ru/TiO2 | 0.85 | 2.5 | weak | 1.4 | 13 | 0.8 |
Ru/SiO2 | 0.71 | 57 | weak, medium and strong | n.d. | 230 | 9 |
Ru/Al2O3 | 1.2 | 38 | weak, medium and strong | 1.2 | 247 | 4.8 |
Ru/ZrO2 | 0.71 | 22 | weak and medium | n.d. | 83 | 2.1 |
Ru/Nb2O5 a | n.d. | 140 | weak | n.d. | 98 | 0 |
Catalyst | XLA (%) | SGVL (%) | YGVL (%) | S4-HPA (%) | Y4-HPA (%) | [4-HPA]/[GVL] | R0 (molLA/s·gRu b) |
---|---|---|---|---|---|---|---|
Ru/C | 61 | 77 | 47 | 23 | 14 | 0.33 | 5.2 × 10−3 |
Ru/CNT | 74 | 83 | 61 | 17 | 13 | 0.21 | n.d. c |
Ru/SiO2 | 47 | 97 | 46 | 3 | 1 | 0.11 | 4.0 × 10−3 |
Ru/Al2O3 | 33 | 56 | 18 | 44 | 14 | 0.79 | 2.4 × 10−3 |
Ru/ZrO2 | 1 | >99 | 1 | 0 | 0 | 0 | 6.4 × 10−5 |
Ru/Nb2O5 | 2 | >99 | 2 | 0 | 0 | 0 | n.d. c |
Ru/TiO2 | 44 | 85 | 37 | 15 | 7 | 0.18 | 3.8 × 10−3 |
Ru/Beta-12.5 | 94 | 70 | 66 | 30 | 28 | 0.41 | 8.9 × 10−3 |
RuPd/TiO2 | 9 | 51 | 5 | 49 | 4 | 0.96 | n.d. c |
Catalyst | wt. % Ru | T (°C) | LA Conversion after 2 h, (%) | GVL Selectivity after 2 h, (%) | 4-HPA Selectivity after 2 h, (%) | R0 (molLA/gRu·s b) | Reference |
---|---|---|---|---|---|---|---|
Ru/C | 1 | 90 | 61 | 75 | 24 | 5.2 × 10−3 | This study a |
Ru/CNT | 1 | 74 | 83 | 17 | n.d. | ||
Ru/SiO2 | 1 | 47 | 97 | 3 | 4.0 × 10−3 | ||
Ru/Al2O3 | 1 | 33 | 56 | 44 | 2.4 × 10−3 | ||
Ru/ZrO2 | 1 | 1 | 99 | 1 | 6.4 × 10−5 | ||
Ru/Nb2O5 | 1 | 2 | 98 | 1 | n.d. | ||
Ru/TiO2 | 1 | 44 | 79 | 15 | 3.7 × 10−3 | ||
Ru/Beta-12.5 | 1 | 95 | 70 | 30 | 8.9 × 10−3 | ||
RuPd/TiO2 | 1 | 9 | 51 | 49 | n.d. | ||
Ru/C | 5 | 130 | 160 min—99.5 | 160 min—86.6 | - | 3.5 × 10−4 | [6] |
Ru/SiO2 | 5 c | 160 min—98 | 160 min—76.5 | - | 3.5 × 10−4 | ||
Ru/Al2O3 | 5 c | 160 min—94.7 | 160 min—80.4 | - | 3.4 × 10−4 | ||
Ru/TiO2 | 5 c | 160 min—81.2 | 160 min—87.8 | - | 2.9 × 10−4 | ||
Ru/TiO2 | 1 | 70 | 1 h—99% | 1 h—95 | - | 7.9 × 10−4 | [7] |
Ru/C | 3 | 90 | 50 min—100% | 50 min—83% | 50 min—17% | 4.5 × 10−2 | [8] |
Ru/C | 5 | 70 | 3 h—48 | 3 h—97.5 | - | 7.5 × 10−4 | [12] |
Ru/Al2O3 | 5 | 70 | 3 h—24 | 3 h—96 | - | 3.7 × 10−4 |
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Piskun, A.; Winkelman, J.G.M.; Tang, Z.; Heeres, H.J. Support Screening Studies on the Hydrogenation of Levulinic Acid to γ-Valerolactone in Water Using Ru Catalysts. Catalysts 2016, 6, 131. https://doi.org/10.3390/catal6090131
Piskun A, Winkelman JGM, Tang Z, Heeres HJ. Support Screening Studies on the Hydrogenation of Levulinic Acid to γ-Valerolactone in Water Using Ru Catalysts. Catalysts. 2016; 6(9):131. https://doi.org/10.3390/catal6090131
Chicago/Turabian StylePiskun, Anna, Jozef G. M. Winkelman, Zhenchen Tang, and Hero Jan Heeres. 2016. "Support Screening Studies on the Hydrogenation of Levulinic Acid to γ-Valerolactone in Water Using Ru Catalysts" Catalysts 6, no. 9: 131. https://doi.org/10.3390/catal6090131