Characterization of Aromatic Compound Sorptive Interactions with Black Carbon (Charcoal) Assisted by Graphite as a Model
Abstract
Molecular interactions controlling the sorption of pollutants to environmental black carbons (soot, charcoal) are not well-resolved. Sorption of a series of aromatic compounds was studied to wood charcoal and nonporous graphite powder as a model adsorbent. Issues of concern were the possible involvement of pi-pi electron donor-acceptor (EDA) interactions of electron-poor and electron-rich solutes with the graphene (polycyclic aromatic) surface and size exclusion effects. Sorption of pi-acceptors, benzonitrile (BNTL), 4-nitrotoluene (MNT), 2,4-dinitrotoluene (DNT), and 2,4,6-trinitrotoluene (TNT), and to a lesser extent pi-donor solutes, naphthalene (NAPH) and phenanthrene (PHEN), was greater than predicted by hydrophobic driving forces in accord with their acceptor or donor strength. Hydrophobic effects were estimated using a concentration-dependent free energy relationship between adsorption and partitioning into an inert solvent (n-hexadecane or benzene) for a non-donor/non-acceptor calibration set (benzene and chlorinated and methylated benzenes). Molecular complexation between acceptors and model graphene donors, NAPH, PHEN, and pyrene (PYR), in chloroform and benzene was tracked by ring-current induced upfield shifts in the 1H NMR spectrum and by charge-transfer bands in the UV/visible spectrum. The EDA component of graphite-water adsorption for the acceptors correlated with the NMR-determined complexation constant with the model donors in chloroform, which, in turn, correlated with pi-acceptor strength (TNT > DNT > MNT > BNTL) and pi-donor strength (PYR > PHEN > NAPH). Charcoal-graphite isotherms calculated from charcoal-water and graphite-water isotherms indicated molecular sieving effects on charcoal for tetrasubstituted benzenes (tetramethylbenzenes and TNT) and some trisubstituted benzenes (1,3,5-trichlorobenzene, possibly DNT). When steric effects are taken into account, the order in adsorption among acceptors was qualitatively similar for graphite and charcoal. The results suggest pi-pi EDA interactions of the acceptors-and possibly donors, although the calibration set may underestimate the hydrophobic effect for fused ring systems-with both graphite and charcoal surfaces. For graphite, it is postulated that pi-acceptors interact with electron-rich regions of the basal plane near edges and defects and that pi-donors interact with electron-depleted regions further away. A similar mechanism may operate on the charcoal but would be modified by the (mostly) electron-withdrawing effects of 0 functionality on the edges of graphene sheets.
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Increasing aromaticity of TBC by phosphoric acid treatment can enhance hydrophobic interactions and π-π interactions, contributing to increased adsorption coefficient.
“The increasing aromaticity of TBC by phosphoric acid treatment can enhance hydrophobic interactions and π -π interactions, which contributed to increase adsorption coefficient (Zhu and Pignatello 2005).”
From Review of organic and inorganic pollutants removal by biochar and biochar-based composites (2021) · cites this paper as Zhu and Pignatello 2005
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- Authors
- Zhu, D., & Pignatello, J. J.
- Affiliations
- Connecticut Agricultural Experiment Station (US)
- Corresponding author
- Pignatello, Joseph J.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-02-18
- Volume
- 39
- Issue
- 7
- Pages
- 2033-2041
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W1984527326
- Cited by
- 425
- References
- 27
- Citations by year
- 2026: 8 · 2025: 12 · 2024: 14 · 2023: 21 · 2022: 24 · 2021: 21 · 2020: 29 · 2019: 21 · 2018: 18 · 2017: 27 · 2016: 42 · 2015: 35 · 2014: 29 · 2013: 20 · 2012: 23
- FWCI
- 10.42
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Environmental Science & Technology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Environmental Science › Water Science and Technology › Adsorption and biosorption for pollutant removal
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Toxic Organic Pollutants Impact
- Physical Sciences › Chemistry › Spectroscopy › Adsorption, diffusion, and thermodynamic properties of materials
- Keywords
- black carbon, wood charcoal, graphite, π-π electron donor-acceptor interactions, graphene surface, nitroaromatic compounds, TNT, 2,4-dinitrotoluene, 4-nitrotoluene, benzonitrile, naphthalene, phenanthrene, pyrene, molecular complexation, charge transfer, hydrophobic effect, size exclusion, molecular sieving, adsorption isotherms, solute size effects
- MeSH terms
- Adsorption, Charcoal, Graphite, Hydrocarbons, Aromatic, Models, Chemical, Magnetic Resonance Spectroscopy
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