Lignin-Derived Syringol and Acetosyringone from Palm Bunch Using Heterogeneous Oxidative Depolymerization over Mixed Metal Oxide Catalysts under Microwave Heating
Abstract
:1. Introduction
2. Materials and Methods
2.1. Biomass and Chemicals
2.2. Co-Impregnation of SiO2, Al2O3 Supported Cu-Fe Catalysts for EFB-Extracted Lignin Depolymerization
2.3. Heterogeneously Mixed Metal Oxides Complex Catalysts Characterization
2.4. Lignin Extraction and Depolymerization of Lignin
2.4.1. Alkali Hydrothermal Extraction of Lignin from Palm Empty Fruit Bunch
2.4.2. Microwave-Assisted Phenolic Compound Production over Heterogeneously Mixed Metal Oxides Complex Catalyst
2.5. Analysis of Lignin Functional Groups and Lignin Depolymerization Products
3. Results and Discussion
3.1. Extracted Lignin from EFB
3.2. Characterization and Reactivity of the Heterogeneously Mixed Metal Oxides Catalysts on Phenolic Compounds Production
3.2.1. X-ray Diffraction (XRD) and X-ray Fluorescence Spectrometry (XRF) of Heterogeneously Mixed Metal Oxide Catalysts
3.2.2. X-ray Photoelectron Spectroscopy (XPS) of Heterogeneously Mixed Metal Oxides Catalysts
3.2.3. NH3-TPD Analysis of Synthesized Catalysts
3.2.4. Field Emission Scanning Electron Microscopy with Energy-Dispersive X-ray Spectroscopy (FESEM-EDX) Map** of Heterogeneously Mixed Metal Oxides Catalysts
3.3. Phenolic Compounds Production from K2CO3-Lignin and NaOH-Lignin with Heterogeneously Mixed Metal Oxides Catalysts
3.4. The Proposed Mechanism of Oxidative Depolymerization of EFB Derived Lignin with Mixed Metal Oxides Cu-Fe Catalyst
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Acknowledgments
Conflicts of Interest
References
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Element (wt%) | Catalyst | |||
---|---|---|---|---|
Cu-Fe/Al2O3 | Cu-Fe/SiO2 | Al2O3 | SiO2 | |
CuO | 12.80 | 12.27 | nd | nd |
Fe2O3 | 8.15 | 10.38 | 0.02 | 0.05 |
Al2O3 | 78.67 | 0.12 | 99.57 | 0.15 |
SiO2 | 0.07 | 76.36 | 0.12 | 98.54 |
Others | 0.31 | 0.87 | 0.29 | 1.26 |
Type of Reaction | Alkaline EFB Extracted Lignin | Catalyst | Main Products (wt%) | Total Phenolic Compounds (wt%) | %Selectivity | Ref. | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Syringol | Vanillin | Aceto-Vanillone | 2,4-Di-tert Butylphenol | Syringal-Dehyde | Aceto Syringone | Syringol | 2,4-Di-tert Butylphenol | Acetosyringone | |||||
Heterogeneous reaction a | 15 min | ||||||||||||
K2CO3-lignin | Cu-Fe/Al2O3 | 7.71 | - | 0.63 | 23.19 | - | 0.64 | 32.17 | 23.97 | 72.09 | 1.99 | This study | |
Cu-Fe/SiO2 | 6.94 | - | 1.08 | 24.39 | - | 0.95 | 33.36 | 20.80 | 73.11 | 2.85 | This study | ||
No Catalyst | 4.89 | 0.97 | 2.40 | 20.71 | - | 2.80 | 31.77 | 15.39 | 65.19 | 8.81 | This study | ||
NaOH-lignin | Cu-Fe/Al2O3 | 13.78 | 0.45 | 2.13 | 20.98 | 0.68 | 4.71 | 42.73 | 32.25 | 49.10 | 11.02 | This study | |
Cu-Fe/SiO2 | 10.07 | 0.41 | 1.60 | 20.02 | 0.87 | 4.33 | 37.30 | 27.00 | 53.67 | 11.61 | This study | ||
No Catalyst | 5.14 | 1.19 | 2.76 | 2.76 | 0.65 | 7.12 | 19.62 | 26.20 | 14.07 | 36.29 | This study | ||
30 min | |||||||||||||
K2CO3-lignin | Cu-Fe/Al2O3 | 13.39 | 1.39 | 2.33 | 20.17 | 0.98 | 4.72 | 42.98 | 31.15 | 46.93 | 10.98 | This study | |
Cu-Fe/SiO2 | 19.21 | 2.16 | 3.69 | 27.29 | 2.16 | 9.36 | 63.87 | 30.08 | 42.73 | 14.65 | This study | ||
No Catalyst | 5.86 | 1.00 | 2.84 | 13.09 | 0.77 | 6.39 | 29.95 | 19.57 | 66.89 | 21.34 | This study | ||
NaOH-lignin | Cu-Fe/Al2O3 | 27.06 | 1.61 | 4.39 | 2.78 | 1.97 | 11.71 | 49.52 | 54.64 | 5.61 | 23.65 | This study | |
Cu-Fe/SiO2 | 13.52 | 1.25 | 2.74 | 2.29 | 1.48 | 7.56 | 28.84 | 46.88 | 7.94 | 26.21 | This study | ||
No Catalyst | 10.34 | 1.35 | 4.7 | 1.27 | 0.79 | 10.28 | 28.73 | 35.99 | 4.42 | 35.78 | This study | ||
Homogeneous reaction b | 15 min | ||||||||||||
K2CO3-lignin | Cu(OH)2 + Fe2O3 | 50.33 | 3.24 | 10.72 | - | 4.96 | 20.48 | 89.73 | 56.09 | - | 22.82 | [26] | |
NaOH-lignin | Cu(OH)2 + Fe2O3 | 28.11 | 1.39 | 4.22 | - | 3.36 | 7.55 | 44.63 | 62.98 | - | 16.92 | [26] | |
30 min | |||||||||||||
K2CO3-lignin | Cu(OH)2 + Fe2O3 | 44.77 | 4.00 | 10.15 | - | 6.66 | 22.52 | 88.1 | 50.82 | - | 25.56 | [26] | |
NaOH-lignin | Cu(OH)2 + Fe2O3 | 52.51 | 3.89 | 8.23 | - | 4.84 | 19.58 | 89.05 | 58.97 | - | 21.99 | [26] |
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Panyadee, R.; Saengsrichan, A.; Posoknistakul, P.; Laosiripojana, N.; Ratchahat, S.; Matsagar, B.M.; Wu, K.C.-W.; Sakdaronnarong, C. Lignin-Derived Syringol and Acetosyringone from Palm Bunch Using Heterogeneous Oxidative Depolymerization over Mixed Metal Oxide Catalysts under Microwave Heating. Molecules 2021, 26, 7444. https://doi.org/10.3390/molecules26247444
Panyadee R, Saengsrichan A, Posoknistakul P, Laosiripojana N, Ratchahat S, Matsagar BM, Wu KC-W, Sakdaronnarong C. Lignin-Derived Syringol and Acetosyringone from Palm Bunch Using Heterogeneous Oxidative Depolymerization over Mixed Metal Oxide Catalysts under Microwave Heating. Molecules. 2021; 26(24):7444. https://doi.org/10.3390/molecules26247444
Chicago/Turabian StylePanyadee, Rangsalid, Aphinan Saengsrichan, Pattaraporn Posoknistakul, Navadol Laosiripojana, Sakhon Ratchahat, Babasaheb M. Matsagar, Kevin C.-W. Wu, and Chularat Sakdaronnarong. 2021. "Lignin-Derived Syringol and Acetosyringone from Palm Bunch Using Heterogeneous Oxidative Depolymerization over Mixed Metal Oxide Catalysts under Microwave Heating" Molecules 26, no. 24: 7444. https://doi.org/10.3390/molecules26247444