Biochar Catalysis for the Enhanced Abiotic Humification of Polyphenols: An Important Mechanism Helping Sequester Carbon
Abstract
:1. Introduction
2. Materials and Methods
2.1. Reagents
2.2. Biochar Preparation and Characterization
2.3. Abiotic Humification Experiment
2.4. Analytical Methods
2.5. Statistical Analysis
3. Results and Discussion
3.1. Humification Process and HQ Transformation under BC600 Catalysis
3.2. Impact of Light and Oxygen
3.3. HO• Quenching Experiment under Light and O2 Conditions
3.4. Effect of Pyrolysis Temperature on Biochar Performance
3.5. Transformation Products and Proposed Reaction Pathway for the Abiotic Humification Reaction of HQ over BC600
- (I).
- HQ is rapidly oxidized to semiquinones or p-benzoquinone radicals by BC600 and ROS like HO•. On the one hand, the configurational transition of p-benzoquinone radicals generates p-benzoquinone (RT = 6.65 min, 24 h) [13,47]. Subsequently, some p-benzoquinone is oxidized by HO• to break the C–C single bond between the C=O and C=C double bond [48], leading to ring cleavage of p-benzoquinone and formation of carboxylic acid fragments and alkenes. Some small carboxylic acid molecules are degraded into inorganic molecules such as CO2 and H2O [36]. On the other hand, p-benzoquinone radicals undergo a series of oxidation coupling reactions to form oligomers, such as 5,6,12,13-tetrahydro- Dibenz[a,h]anthracene (RT = 34.90 min, 128 h) [7,20].
- (II).
- The polymerization of benzoquinone, carboxylic acid fragments, and alkenes via Diels–Alder reaction, esterification, and cyclization reaction produces HSs, including 2-(1,3-cyclohexadienyl)-5,5-dimethyl-1,3-Cyclohexanedione (RT = 16.7 min, 24 h), 1,2,4-Benzenetricarboxylic acid 4-dodecyl 1,2-dimethyl ester (RT = 34.91 min, 24 h), 1,3-Benzenedicarboxylic acid, bis(2-ethylhexyl) ester (RT = 30.72 min, 128 h), 7,9-Di-tert-butyl-1-oxaspiro(4,5)deca-6,9-diene-2,8-dione (RT = 20.97 min, 360 h), and 1,1′,1′′,1′′′-(1,5-hexadiene-1,3,4,6-tetrayl) tetrakis- Benzene (RT = 28.59 min, 360 h).
- (III).
- HSs are produced by the polymerization of BC600-derived DOM, carboxylic acid fragments, and alkenes. Dibutyl phthalate (RT = 21.51 min, control), generated by BC600 and alkenes, undergoes addition reactions to form diisooctyl phthalate (RT = 28.66 min, 24 h) and 2-ethylbutyl methyl phthalate (RT = 14.00 min, 128 h). Heptadecyl acetate (RT = 27.02 min, 128 h) and tricosyl acetate (RT = 24.62, 360 h) may originate from hexadecane (RT = 16.07 min, control) and 1-Octadecene (RT = 24.63 min, control) from BC600.
- (IV).
- HSs such as phthalic acid and isobutyl 2-methylpent-3-yl ester originate from BC600, as these compounds were detected in both the control system and the BC600–HQ systems.
4. Conclusions and Implications
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
- Deng, X.; Teng, F.; Chen, M.P.; Du, Z.L.; Wang, B.; Li, R.Q.; Wang, P. Exploring negative emission potential of biochar to achieve carbon neutrality goal in China. Nat. Commun. 2024, 15, 1085. [Google Scholar] [CrossRef] [PubMed]
- Lehmann, J.; Cowie, A.; Masiello, C.A.; Kammann, C.; Woolf, D.; Amonette, J.E.; Cayuela, M.L.; Camps-Arbestain, M.; Whitman, T. Biochar in climate change mitigation. Nat. Geosci. 2021, 12, 883–892. [Google Scholar] [CrossRef]
- Cybulak, M.; Sokołowska, Z.; Boguta, P. The influence of biochar on the content of carbon and the chemical transformations of fallow and grassland humic acids. Sci. Rep. 2021, 11, 5698. [Google Scholar] [CrossRef]
- Wang, L.W.; Deng, J.Y.; Yang, X.D.; Hou, R.J.; Hou, D.Y. Role of biochar toward carbon neutrality. Carbon Res. 2023, 2, 2. [Google Scholar] [CrossRef]
- Moore, O.W.; Curti, L.; Woulds, C.; Bradley, J.A.; Babakhani, P.; Mills, B.J.W.; Homoky, W.B.; Xiao, K.Q.; Bray, A.W.; Fisher, B.J.; et al. Long-term organic carbon preservation enhanced by iron and manganese. Nature 2023, 621, 312–317. [Google Scholar] [CrossRef] [PubMed]
- Dou, S.; Shan, J.; Song, X.Y.; Cao, R.; Wu, M.; Li, C.L.; Guan, S. Are humic substances soil microbial residues or unique synthesized compounds? A perspective on their distinctiveness. Pedosphere 2020, 2, 159–167. [Google Scholar] [CrossRef]
- Zhang, X.M.; Zong, Y.; Xu, L.Q.; Mao, Y.F.; Wu, D.L. Enhanced abiotic integrated polyphenol-Maillard humification by Mg/Fe layered double hydroxide (LDH): Role of Fe(III)-polyphenol complexation. Chem. Eng. J. 2021, 425, 130521. [Google Scholar] [CrossRef]
- Zavarzina, A.G.; Danchenko, N.N.; Demin, V.V.; Artemyevas, Z.S.; Kogut, B.M. Humic Substances: Hypotheses and Reality (a Review). Eurasian Soil Sci. 2021, 54, 1826–1854. [Google Scholar] [CrossRef]
- Zhang, Y.C.; Xu, Y.; Yu, X.L.; Li, J.K.; Chen, G.; Wang, S.J.; Xu, Y.P.; Xu, R.; Zhang, B.H.; Zhang, H.Q. Microbial metabolism and humic acid formation in response to enhanced copper and zinc passivation during composting of wine grape pomace and pig manure. Bioresour. Technol. 2023, 384, 129226. [Google Scholar] [CrossRef]
- Meng, W.S.; Zhu, F.N.; Wang, X.R.; Guan, S.; Dou, S.; Ndzelu, B.S. Contrasting effects of straw and straw-derived biochar application on soil organic matter and corn yield in a Chinese Mollisol. J. Soil. Sediment. 2023, 23, 3843–3856. [Google Scholar] [CrossRef]
- Zhang, Y.C.; Bi, Z.T.; Tian, W.X.; Ge, Z.Y.; Xu, Y.; Xu, R.; Zhang, H.Q.; Tang, S.F. Synergistic effect triggered by Fe2O3 and oxygen-induced hydroxyl radical enhances formation of amino-phenolic humic-like substance. J. Environ. Manag. 2023, 348, 119312. [Google Scholar] [CrossRef] [PubMed]
- Zou, J.; Huang, J.Z.; Yue, D.B.; Zhang, H.C. Roles of oxygen and Mn (IV) oxide in abiotic formation of humic substances by oxidative polymerization of polyphenol and amino acid. Chem. Eng. J. 2020, 393, 124734. [Google Scholar] [CrossRef]
- Liu, M.M.; Cao, X.H.; Tan, W.F.; Feng, X.H.; Qiu, G.H.; Chen, X.H.; Liu, F. Structural controls on the catalytic polymerization of hydroquinone by birnessites. Clays Clay Miner. 2011, 5, 525–537. [Google Scholar] [CrossRef]
- Jokic, A.; Frenkel, A.; Vairavamurthy, M.; Huang, P. Birnessite catalysis of the Maillard reaction: Its significance in natural humification. Geophys. Res. Lett. 2001, 28, 3899–3902. [Google Scholar] [CrossRef]
- Wang, M.C.; Huang, P.M. Cleavage of 14C-labeled glycine and its polycondensation with pyrogallol as catalyzed by birnessite. Geoderma 2005, 124, 415–426. [Google Scholar] [CrossRef]
- Hardie, A.G.; Dynes, J.J.; Kozak, L.M.; Huang, P.M. Influence of polyphenols on the integrated polyphenol-maillard reaction humification pathway as catalyzed by birnessite. Ann. Environ. Sci. 2007, 1, 91–110. [Google Scholar]
- Miura, A.; Okabe, R.; Izumo, K.; Fukushima, M. Influence of the physicochemical properties of clay minerals on the degree of darkening via polycondensation reactions between catechol and glycine. Appl. Clay Sci. 2009, 46, 277–282. [Google Scholar] [CrossRef]
- Bui, V.K.H.; Nguyen, X.C.; Bang, T.H.; Jin, H. Using CuMgFe layered double oxide to replace laccase as a catalyst for abiotic humification. Chemosphere 2024, 353, 141647. [Google Scholar] [CrossRef]
- Zhang, Y.C.; Yue, D.B.; Fang, D.; Dong, X.W.; Li, W.L. Enhanced darkening effect from the interaction of MnO2 and oxygen on the component evolution of amino-phenolic humic-like substances. Chemosphere 2021, 263, 127956. [Google Scholar] [CrossRef]
- Dou, J.B.; Tang, Y.; Lu, Z.J.; He, G.Z.; Xu, J.M.; He, Y. Neglected but efficient electron utilization driven by biochar-coactivated phenols and peroxydisulfate: Polyphenol accumulation rather than mineralization. Environ. Sci. Technol. 2023, 14, 5703–5713. [Google Scholar] [CrossRef]
- Lyu, H.H.; Zhang, Q.R.; Shen, B.X. Application of biochar and its composites in catalysis. Chemosphere 2020, 240, 124842. [Google Scholar] [CrossRef] [PubMed]
- Fang, G.D.; Zhu, C.Y.; Dionysiou, D.D.; Gao, J.; Zhou, D.M. Mechanism of hydroxyl radical generation from biochar suspensions: Implications to diethyl phthalate degradation. Bioresour. Technol. 2015, 176, 210–217. [Google Scholar] [CrossRef] [PubMed]
- Fang, G.D.; Liu, C.; Wang, Y.J.; Dionysiou, D.D.; Zhou, D.M. Photogeneration of reactive oxygen species from biochar suspension for diethyl phthalate degradation. Appl. Catal. B Environ. 2017, 214, 34–45. [Google Scholar] [CrossRef]
- Gao, Y.; Sun, Y.R.; Song, W.S.; Jia, Y.F.; Li, A.M.; Wang, S.F. Intrinsic properties of biochar for electron transfer. Chem. Eng. J. 2023, 475, 146356. [Google Scholar] [CrossRef]
- Baye, F.A.; Bandal, H.A.; Kim, H. FeCx-coated biochar nanosheets as efficient bifunctional catalyst for electrochemical detection and reduction of 4-nitrophenol. Environ. Res. 2024, 246, 118071. [Google Scholar] [CrossRef]
- Zhang, P.; Zhang, P.J.; Feng, S.H.; Li, H.; Li, J.; Du, W.; Duan, W.Y.; Li, X.H.; Zhang, C.; Li, H.X.; et al. The mechanism of p-nitrophenol degradation by dissolved organic matter derived from biochar. Sci. Total Environ. 2023, 868, 8. [Google Scholar] [CrossRef]
- Zhang, R.R.; Zhang, R.L.; Zimmerman, A.R.; Wang, H.L.; Gao, B. Applications, impacts, and management of biochar persistent free radicals: A review. Environ. Pollut. 2023, 15, 121543. [Google Scholar] [CrossRef]
- Sun, Z.Y.; Chu, L.G.; Wang, X.H.; Fang, G.D.; Liu, C.; Chen, H.; Gu, C.; Gao, J. Roles of natural phenolic compounds in polycyclic aromatic hydrocarbons abiotic attenuation at soil-air interfaces through oxidative coupling reactions. Environ. Sci. Technol. 2023, 32, 11967–11976. [Google Scholar] [CrossRef]
- Qin, W.X.; Wang, Y.J.; Fang, G.D.; Liu, C.; Sui, Y.X.; Zhou, D.M. Oxidation mechanism of As(III) in the presence of polyphenols: New insights into the reactive oxygen species. Chem. Eng. J. 2016, 285, 69–76. [Google Scholar] [CrossRef]
- Zhou, J.M.; Chen, H.L.; Tao, Y.L.; Thring, R.W.; Mao, J.L. Biochar amendment of chromium-polluted paddy soil suppresses greenhouse gas emissions and decreases chromium uptake by rice grain. J. Soil Sediment. 2019, 19, 1756–1766. [Google Scholar] [CrossRef]
- Duan, Y.M.; Awasthia, S.K.; Liu, T.; Zhang, Z.Q.; Awasthi, M.K. Response of bamboo biochar amendment on volatile fatty acids accumulation reduction and humification during chicken manure composting. Bioresour. Technol. 2019, 291, 121845. [Google Scholar] [CrossRef] [PubMed]
- Zhang, Y.C.; Yue, D.B.; Ma, H. Darkening mechanism and kinetics of humification process in catechol-Maillard system. Chemosphere 2015, 130, 40–45. [Google Scholar] [CrossRef]
- Reddy, S.; Nagaraja, M.S.; Raj, T.P.; Patil, A.P.; Dhumgond, P. Elemental analysis, E4/E6 ratio and total acidity of soil humic and fulvic acids from different land use systems. Ann. Plant Soil Res. 2014, 2, 89–92. [Google Scholar]
- Sun, Z.Y.; Wang, X.H.; Liu, C.; Fang, G.D.; Chu, L.G.; Gu, C.; Gao, J. Persistent free radicals from low-molecular-weight organic compounds enhance cross-coupling reactions and toxicity of anthracene on amorphous silica surfaces under light. Environ. Sci. Technol. 2021, 55, 3716–3726. [Google Scholar] [CrossRef] [PubMed]
- Zhang, H.W.; Zhang, X.M.; Ding, L.; Gong, M.; Su, Y.; Wang, S.W. Polymerization and oxidation of phenols in supercritical water. Water Sci. Technol. 2019, 80, 4. [Google Scholar] [CrossRef]
- Zhang, Z.T.; Yi, G.Y.; Li, P.; Wan, X.K.; Wang, X.D.; Zhang, C.X.; Zhang, Y.L.; Sun, Q. Electrochemical oxidation of hydroquinone using Eu-doped PbO2 electrodes: Electrode characterization, influencing factors and degradation pathways. J. Electroanal. Chem. 2021, 895, 115493. [Google Scholar] [CrossRef]
- Link, N.; Removski, N.; Yun, J.; Fleming, L.T.; Nizkorodov, S.A.; Bertram, A.K.; Al-Abadleh, H.A. Dust-catalyzed oxidative polymerization of catechol and its impacts on ice nucleation efficiency and optical properties. ACS Earth Space Chem. 2020, 4, 1127–1139. [Google Scholar] [CrossRef]
- Gokturk, E.; Ocsoy, I.; Turac, E.; Sahmetlioglu, E. Horseradish peroxidase-based hybrid nanoflowers with enhanced catalytical activities for polymerization reactions of phenol derivatives. Polym. Advan. Technol. 2020, 31, 2371–2377. [Google Scholar] [CrossRef]
- Velasco, L.F.; Fonseca, I.M.; Parra, J.B.; Lima, J.C.; Ania, C.O. Photochemical behaviour of activated carbons under UV irradiation. Carbon 2012, 50, 249–258. [Google Scholar] [CrossRef]
- McNeill, K.; Canonica, S. Triplet state dissolved organic matter in aquatic photochemistry: Reaction mechanisms, substrate scope, and photophysical properties. Environ. Sci. Process. Impacts 2016, 18, 1381–1399. [Google Scholar] [CrossRef]
- Khachatryan, L.; Vejerano, E.; Lomnicki, S.; Dellinger, B. Environmentally persistent free radicals (EPFRs). 1. Generation of reactive oxygen species in aqueous solutions. Environ. Sci. Technol. 2011, 45, 8559–8566. [Google Scholar] [CrossRef]
- Yang, F.; Zhu, Q.; Gao, Y.; Jian, H.X.; Wang, C.P.; Sun, H.W. Effects of biochar-dissolved organic matter on the photodegradation of sulfamethoxazole and chloramphenicol in biochar solutions as revealed by oxygen reduction performances and free radicals. Sci. Total Environ. 2021, 781, 146807. [Google Scholar] [CrossRef]
- Liu, F.H.; Zhu, K.C.; Wang, Z.Q.; Liu, J.B.; Ni, Z.; Ding, Y.Y.; Zhang, C.; Jia, H.Z. Production of reactive oxygen species and its role in mediating the abiotic transformation of organic carbon in sandy soil under vegetation restoration. Carbon Res. 2023, 2, 35. [Google Scholar] [CrossRef]
- Zhang, Y. Theoretical Investigations of Reactions between Methanol and Several Free Radicals. Master’s Thesis, Chongqing University, Chongqing, China, 2019. [Google Scholar]
- Goutham, R.; Ramin, F. Role of persistent free radicals and lewis acid sites in visible-light-driven wet peroxide activation by solid acid biochar catalysts—A mechanistic study. J. Hazard. Mater. 2022, 438, 129514. [Google Scholar]
- Jiang, H.Y.; Zhao, M.Z.; Hong, W.J.; Song, W.H.; Yan, S.W. Mechanistic and Kinetic consideration of the photochemically generated oxidative organic radicals in dissolved black carbon solutions under simulated solar Irradiation. Environ. Sci. Technol. 2024, 58, 760–770. [Google Scholar] [CrossRef] [PubMed]
- Kim, S.H.; Matsubara, R.; Hayashi, M. Activated carbon-promoted dehydrogenation of hydroquinones to benzoquinones, naphthoquinones, and anthraquinones under molecular oxygen atmosphere. J. Org. Chem. 2019, 5, 2997–3003. [Google Scholar] [CrossRef]
- Szabóa, V.; Mészáros, R.; Kónya, Z.; Kukovecz, Á.; Pálinkóa, I.; Sipos, P.; Szabados, M. Preparation and characterization of MnIn-layered double hydroxides (LDHs), extension of the synthesis to fabricate Mn M(III)-LDHs (M = Al, Sc, Cr, Fe, Ga), and the comparison of their photocatalytic and catalytic activities in the oxidation of hydroquinone. J. Mol. Struct. 2022, 1, 132966. [Google Scholar] [CrossRef]
- Polyakov, V.; Evgeny, A.; Evgeny, L.; Roman, V. Molecular weight distribution of humic acids isolated from buried soils and Yedoma sediments. Agronomy 2023, 13, 1483. [Google Scholar] [CrossRef]
Biochar | Yield a (%) | pH | DOC (mg g−1) | SBET b (m2 g−1) | Smicro c (m2 g−1) | Vtotal d (cm3 g−1) | Vmicro e (cm3 g−1) |
---|---|---|---|---|---|---|---|
BC300 | 40.89 | 7.38 | 0.74 | 6.77 | 4.69 | 0.005 | 0.002 |
BC600 | 24.56 | 11.47 | 0.28 | 329.51 | 303.04 | 0.14 | 0.11 |
BC900 | 23.21 | 12.02 | 0.05 | 26.69 | 27.52 | 0.02 | 0.01 |
Sample | Mn a (Da) | Mw b (Da) | Mp c (Da) | Mz d (Da) | Polydispersity |
---|---|---|---|---|---|
only HQ | 420 | 463 | 407 | 516 | 1.103 |
HQ + glucose + glycine | 13,935 | 14,449 | 12,668 | 15,193 | 1.037 |
8033 | 8143 | 8487 | 8234 | 1.014 |
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Zhou, J.; Zhou, Z.; Yao, C.; Zhang, Y.; Ren, H.; Lu, G.; Chen, H. Biochar Catalysis for the Enhanced Abiotic Humification of Polyphenols: An Important Mechanism Helping Sequester Carbon. Agronomy 2024, 14, 1951. https://doi.org/10.3390/agronomy14091951
Zhou J, Zhou Z, Yao C, Zhang Y, Ren H, Lu G, Chen H. Biochar Catalysis for the Enhanced Abiotic Humification of Polyphenols: An Important Mechanism Helping Sequester Carbon. Agronomy. 2024; 14(9):1951. https://doi.org/10.3390/agronomy14091951
Chicago/Turabian StyleZhou, Jiangmin, Ziru Zhou, Chuanqing Yao, Yujie Zhang, Han Ren, Guining Lu, and Hualin Chen. 2024. "Biochar Catalysis for the Enhanced Abiotic Humification of Polyphenols: An Important Mechanism Helping Sequester Carbon" Agronomy 14, no. 9: 1951. https://doi.org/10.3390/agronomy14091951