Skip to main content
Log in

Effects of the biochar aromaticity and molecular structures of the chlorinated organic compounds on the adsorption characteristics

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

Adsorption behaviors of the chlorinated organic compounds (COCs) (i.e., trichloroethylene (TCE), 1,2,4-trichlorobenzene (1,2,4-TCB); 1,2-dichlorobenzene (1,2-DCB); and monochlorobenzene (MCB)) by the commercial rice husk-based biochar (RH500) and the laboratory-prepared biochars from corn stalks under different pyrolytic temperatures (i.e., CS300, CS500, CS700) were examined and interpreted by the pseudo-first-order kinetic model, the double layer model with two energies, and the Freundlich model. It is identified that the first-order adsorption rate constants (k 1 = 0.06∼0.51 h−1) were proportional to the high aromaticity and/or low polarity of biochars and the strong hydrophobicity of the COCs. The saturated adsorption capacity for the COCs was followed by the order of RH500 > CS500 > CS700 > CS300. RH500 showed the highest adsorption capacity for the COCs due to its high surface area (SA) and total pore volume (TPV). However, CS500 with low SA and TPV development highlighted the important roles of the aromaticity and/or low polarity on the COCs adsorption. In addition, 1,2,4-TCB showed the highest saturated adsorption capacity on all biochars, followed by TCE, 1,2-DCB, and MCB. The results further revealed the positive effects of the physical properties (α, N M, ε 1, and ε 2), the hydrophobicity and electrostatic forces (i.e., π-π interaction and electron donor-acceptor interaction) between the adsorbates and the aromatic moieties of biochar surfaces on the adsorption of COCs.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  • Ahmad M, Lee SS, Oh SE, Mohan D, Moon DH, Lee YH, Ok YS (2013) Modeling adsorption kinetics of trichloroethylene onto biochars derived from soybean stover and peanut shell wastes. Environ Sci Pollut Res 20(12):8364–8373

    Article  CAS  Google Scholar 

  • Ahmad M, Rajapaksha AU, Lim JE, Zhang M, Bolan N, Mohan D, Vithanage M, Lee SS, Ok YS (2014) Biochar as a sorbent for contaminant management in soil and water: a review. Chemosphere 99:19–33

    Article  CAS  Google Scholar 

  • Baldock JA, Smernik RJ (2002) Chemical composition and bioavailability of thermally, altered Pinus resinosa (Red pine) wood. Org Geochem 33(9):1093–1109

    Article  CAS  Google Scholar 

  • Beesley L, Moreno-Jimenez E, Gomez-Eyles JL (2010) Effects of biochar and greenwaste compost amendments on mobility, bioavailability and toxicity of inorganic and organic contaminants in a multi-element polluted soil. Environ Pollut 158(6):2282–2287

    Article  CAS  Google Scholar 

  • Ben Yahia M, Knani S, Dhaou H, Hachicha MA, Jemni A, Ben Lamine A (2013) Modeling and interpretations by the statistical physics formalism of hydrogen adsorption isotherm on LaNi4.75 Fe0.25. Int J Hydrog Energy 38:536–542

    Article  Google Scholar 

  • Bopp C, Christl I, Schulin R, Evangelou MWH (2016) Biochar as possible long-term soil amendment for phytostabilisation of TCE-contaminated soils. Environ Sci Pollut Res 23(17):17449–17458

    Article  CAS  Google Scholar 

  • Cabal B, Ania CO, Parra JB, Pis JJ (2009) Kinetics of naphthalene adsorption on an activated carbon: comparison between aqueous and organic media. Chemosphere 76:433–438

    Article  CAS  Google Scholar 

  • Cao X, Ma L, Gao B, Harris W (2009) Dairy-manure derived biochar effectively sorbs lead and atrazine. Environ Sci Technol 43(9):3285–3291

    Article  CAS  Google Scholar 

  • Cao XY, Pignatello JJ, Li Y, Lattao C, Chappell MA, Chen N, Miller LF, Mao JD (2012) Characterization of wood chars produced at different temperatures using advanced solid-state C-13 NMR spectroscopic techniques. Energy Fuel 26(9):5983–5991

    Article  CAS  Google Scholar 

  • Chefetz B (2003) Sorption of phenanthrene and atrazine by plant cuticular fractions. Environ Toxicol Chem 22:2492–2498

    Article  CAS  Google Scholar 

  • Chefetz B, Xing B (2009) Relative role of aliphatic and aromatic moieties as sorption domains for organic compounds: a review. Environ Sci Technol 43(6):1680–1688

    Article  CAS  Google Scholar 

  • Chefetz B, Deshmukh A, Hatcher PG, Guthrie EA (2000) Pyrene sorption by natural organic matter. Environ Sci Technol 34:2925–2930

    Article  CAS  Google Scholar 

  • Chen BL, Xing BS (2005) Sorption and conformational characteristics of reconstituted plant cuticular waxes on montmorillonite. Environ Sci Technol 39(21):8315–8323

    Article  CAS  Google Scholar 

  • Chen BL, Yuan MX (2011) Enhanced sorption of polycyclic aromatic hydrocarbons by soil amended with biochar. J Soils Sed 11(1):62–71

    Article  Google Scholar 

  • Chen W, Duan L, Zhu D (2007) Adsorption of polar and nonpolar organic chemicals to carbon nanotubes. Environ Sci Technol 41(24):8295–8300

    Article  CAS  Google Scholar 

  • Chen BL, Zhou D, Zhu L (2008) Transitional adsorption and partition of nonpolar and polar aromatic contaminants by biochars of pine needles with different pyrolytic temperatures. Environ Sci Technol 42(14):5137–5143

    Article  CAS  Google Scholar 

  • Chen ZM, Chen BL, Chiou CT (2012) Fast and slow rates of naphthalene sorption to biochars produced at different temperatures. Environ Sci Technol 46(20):11104–11111

    Article  CAS  Google Scholar 

  • Chen CP, Cheng CH, Huang YH, Chen CT, Lai CM, Menyailo OV, Fan LJ, Yang YW (2014) Converting leguminous green manure into biochar: changes in chemical composition and C and N mineralization. Geoderma 232:581–588

    Article  Google Scholar 

  • Chio H, Al-Abed SR (2009) PCB congener sorption to carbonaceous sediment components: macroscopic comparison and characterization of sorption kinetics and mechanism. J Hazard Mater 165:860–866

    Article  Google Scholar 

  • Chun Y, Sheng GY, Chiou CT, Xing BS (2004) Compositions and sorptive properties of crop residue-derived chars. Environ Sci Technol 38(17):4649–4655

    Article  CAS  Google Scholar 

  • Cotoruelo LM, Marques MD, Rodriguez-Mirasol J, Rodriguez JJ, Cordero T (2009) Lignin-based activated carbons for adsorption of sodium dodecylbenzene sulfonate: equilibrium and kinetic studies. J Colloid Interface Sci 332(1):39–45

    Article  CAS  Google Scholar 

  • Fagan SB, Souza AG, Lima JOG, Mendes J, Ferreira OP, Mazali IO, Alves OL, Dresselhaus MS (2004) 1,2-dichlorobenzene interacting with carbon nanotubes. Nano Lett 4(7):1285–1288

    Article  CAS  Google Scholar 

  • Fu P, Hu S, Sun LS, Xiang J, Yang T, Zhang AC, Zhang JY (2009) Structural evolution of maize stalk/char particles during pyrolysis. Bioresour Technol 100(20):4877–4883

    Article  CAS  Google Scholar 

  • Hale SE, Hanley K, Lehmann J, Zimmerman AR, Cornelissen G (2011) Effects of chemical, biological, and physical aging as well as soil addition on the sorption of pyrene to activated carbon and biochar. Environ Sci Technol 45(24):10445–10453

    Article  CAS  Google Scholar 

  • Han L, Qian LB, Yan JC, Chen MF (2016) Contributions of different biomass components to the sorption of 1,2,4-trichlorobenzene under a series of pyrolytic temperatures. Chemosphere 156:262–271

    Article  CAS  Google Scholar 

  • Kang S, Xing BS (2005) Phenanthrene sorption to sequentially extracted soil humic acids and humins. Environ Sci Technol 39:134–140

    Article  CAS  Google Scholar 

  • Keiluweit M, Nico PS, Johnson MG, Kleber M (2010) Dynamic molecular structure of plant biomass-derived black carbon (biochar). Environ Sci Technol 44(4):1247–1253

    Article  CAS  Google Scholar 

  • Khalfaoui M, Knani S, Hachicha MA, Ben Lamine A (2003) New theoretical expressions for the five adsorption type isotherms classified by BET based on statistical physics treatment. J Colloid Interface Sci 263:350–356

    Article  CAS  Google Scholar 

  • Khalfaoui M, Baouab MHV, Gauthier R, Ben Lamine A (2006) Acid dye adsorption onto cationized polyamide fibres. Modeling and consequent interpretations of model parameter behaviours. J Colloid Interface Sci 296(2): 419–427

  • Knani S, Mathlouthi M, Ben Lamine A (2007) Modeling of the psychophysical response curves using the grand canonical ensemble in statistical physics. Food Biophys 2:183–192

    Article  Google Scholar 

  • Koltowski M, Hilber I, Bucheli TD, Oleszczuk P (2016) Effect of activated carbon and biochars on the bioavailability of polycyclic aromatic hydrocarbons in different industrially contaminated soils. Environ Sci Pollut Res 23(11):11058–11068

    Article  CAS  Google Scholar 

  • Lattao C, Cao X, Mao J, Schmidt-Rohr K, Pignatello JJ (2014) Influence of molecular structure and adsorbent properties on sorption of organic compounds to a temperature series of wood chars. Environ Sci Technol 48(9):4790–4798

    Article  CAS  Google Scholar 

  • Lee JW, Kidder M, Evans BR, Paik S, Buchanan AC III, Garten CT, Brown RC (2010) Characterization of biochars produced from cornstovers for soil amendment. Environ Sci Technol 44(20):7970–7974

    Article  CAS  Google Scholar 

  • Lehmann J (2007) A handful of carbon. Nature 447(7141):143–144

    Article  CAS  Google Scholar 

  • Li L, Quinlivan PA, Knappe DRU (2002) Effects of activated carbon surface chemistry and pore structure on the adsorption of organic contaminants from aqueous solution. Carbon 40:2085–2100

    Article  CAS  Google Scholar 

  • Li JF, Li YM, Wu YL, Zheng MY (2014) A comparison of biochars from lignin, cellulose and wood as the sorbent to an aromatic pollutant. J Hazard Mater 280:450–457

    Article  CAS  Google Scholar 

  • Liao Y, Ma T, Cui Y, Qi Z (2014) Spatial distribution characteristics of volatile halogenated hydrocarbons in unsaturated zone of Xiaodian sewage irrigation area, Taiyuan, China. Ecotoxicology 23(10):1951–1957

    Article  CAS  Google Scholar 

  • Liu Z, Zhang FS, Wu J (2010) Characterization and application of chars produced from pinewood pyrolysis and hydrothermal treatment. Fuel 89(2):510–514

    Article  CAS  Google Scholar 

  • Liu WJ, Jiang H, Yu HQ (2015) Development of biochar-based functional materials: toward a sustainable platform carbon material. Chem Rev 115(22):12251–12285

    Article  CAS  Google Scholar 

  • Luo F, Song J, Xia WX, Dong MG, Chen MF, Soudek P (2014) Characterization of contaminants and evaluation of the suitability for land application of maize and sludge biochars. Environ Sci Pollut Res 21(14):8707–8717

    Article  CAS  Google Scholar 

  • Ma XM, Anand D, Zhang XF, Talapatra S (2011) Adsorption and desorption of chlorinated compounds from pristine and thermally treated multiwalled carbon nanotubes. J Phys Chem C 115(11):4552–4557

    Article  CAS  Google Scholar 

  • Nguyen TH, Cho HH, Poster DL, Ball WP (2007) Evidence for a pore-filling mechanism in the adsorption of aromatic hydrocarbons to a natural wood char. Environ Sci Technol 41(4):1212–1217

    Article  CAS  Google Scholar 

  • Pastor-Villegas J, Rodriguez JMM, Pastor-Valle JF, Garcia MG (2007) Changes in commercial wood charcoals by thermal treatments. J Anal Appl Pyrolysis 80(2):507–514

    Article  CAS  Google Scholar 

  • Pelekani C, Snoeyink VL (2000) Competitive adsorption between atrazine and methylene blue on activated carbon: the importance of pore size distribution. Carbon 38(10):1423–1436

    Article  CAS  Google Scholar 

  • Qian LB, Chen BL (2013) Dual role of biochars as adsorbents for aluminum: the effects of oxygen-containing organic components and the scattering of silicate particles. Environ Sci Technol 47(15):8759–8768

    CAS  Google Scholar 

  • Qian LB, Zhang W, Yan J, Han L, Gao W, Liu R, Chen M (2016) Effective removal of heavy metal by biochar colloids under different pyrolysis temperatures. Bioresour Technol 206:217–224

    Article  CAS  Google Scholar 

  • Ran Y, Yang Y, Xing B, Pignatello JJ, Kwon S, Su W, Zhou L (2013) Evidence of micropore filling for sorption of nonpolar organic contaminants by condensed organic matter. J Environ Qual 42(3):806–814

    Article  CAS  Google Scholar 

  • Roberts KG, Gloy BA, Joseph S, Scott NR, Lehmann J (2010) Life cycle assessment of biochar systems: estimating the energetic, economic, and climate change potential. Environ Sci Technol 44(2):827–833

    Article  CAS  Google Scholar 

  • Schmidt MWI, Noack AG (2000) Black carbon in soils and sediments: analysis, distribution, implications, and current challenges. Glob Biogeochem Cycles 14(3):777–793

    Article  CAS  Google Scholar 

  • Sellaoui L, Guedidi H, Knani S, Reinert L, Duclaux L, Ben Lamine A (2015) Application of statistical physics formalism to the modeling of adsorption isotherms of ibuprofen on activated carbon. Fluid Phase Equilib 387:103–110

    Article  CAS  Google Scholar 

  • Sellaoui L, Knani S, Erto A, Hachicha MA, Ben Lamine A (2016) Equilibrium isotherm simulation of tetrachlorethylene on activated carbon using the double layer model with two energies: steric and energetic interpretations. Fluid Phase Equilib 387:259–264

    Article  Google Scholar 

  • Sharma RK, Wooten JB, Baliga VL, Martoglio-Smith PA, Hajaligol MR (2002) Characterization of char from the pyrolysis of tobacco. J Agric Food Chem 50(4):771–783

    Article  CAS  Google Scholar 

  • Song Y, Wang F, Bian YR, Zhang YP, Jiang X (2012) Chlorobenzenes and organochlorinated pesticides in vegetable soils from an industrial site, China. J Environ Sci (China) 24(3):362–368

    Article  CAS  Google Scholar 

  • Song Y, Wang F, Kengara FO, Yang X, Gu C, Jiang X (2013) Immobilization of chlorobenzenes in soil using wheat straw biochar. J Agric Food Chem 61(18):4210–4217

  • Sun K, Jin J, Keiluweit M, Kleber M, Wang Z, Pan Z, Xing B (2012) Polar and aliphatic domains regulate sorption of phthalic acid esters (PAEs) to biochars. Bioresour Technol 118:120–127

  • Tan X, Liu Y, Zeng G, Wang X, Hu X, Gu Y, Yang Z (2015) Application of biochar for the removal of pollutants from aqueous solutions. Chemosphere 125:70–85

    Article  CAS  Google Scholar 

  • Wang XL, Xing BS (2007a) Importance of structural makeup of biopolymers for organic contaminant sorption. Environ Sci Technol 41(10):3559–3565

    Article  CAS  Google Scholar 

  • Wang XL, Xing BS (2007b) Sorption of organic contaminants by biopolymer-derived chars. Environ Sci Technol 41(24):8342–8348

    Article  CAS  Google Scholar 

  • Wang XL, Cook R, Tao S, Xing BS (2007) Sorption of organic contaminants by biopolymers: role of polarity, structure and domain spatial arrangement. Chemosphere 66(8):1476–1484

    Article  CAS  Google Scholar 

  • Wang Y, Hu YT, Zhao X, Wang SQ, Xing GX (2013) Comparisons of biochar properties from wood material and crop residues at different temperatures and residence times. Energy Fuel 27(10):5890–5899

    Article  CAS  Google Scholar 

  • Wang B, Chen W, Fu H, Qu X, Zheng S, Xu Z, Zhu D (2014) Comparison of adsorption isotherms of single-ringed compounds between carbon nanomaterials and porous carbonaceous materials over six-order-of-magnitude concentration range. Carbon 79:203–212

    Article  CAS  Google Scholar 

  • Xiao F, Pignatello JJ (2015) Pi(+)-pi interactions between (hetero) aromatic amine cations and the graphitic surfaces of pyrogenic carbonaceous materials. Environ Sci Technol 49(2):906–914

    Article  CAS  Google Scholar 

  • Xiao L, Bi E, Du B, Zhao X, Xing C (2013) Surface characterization of maize-straw-derived biochars and their sorption performance for MTBE and benzene. Environ Earth Sci 71(12):5195–5205

    Article  Google Scholar 

  • Xing BS (2001) Sorption of naphthalene and phenanthrene by soil humic acids. Environ Pollut 111:303–309

    Article  CAS  Google Scholar 

  • Yang GP, Yang B, Lu XL, Ding HB, He Z (2014) Spatio-temporal variations of sea surface halocarbon concentrations and fluxes from southern Yellow Sea. Biogeochemistry 121(2):369–388

    Article  CAS  Google Scholar 

  • Zhang GX, Zhang Q, Sun K, Liu XT, Zheng WJ, Zhao Y (2011) Sorption of simazine to corn straw biochars prepared at different pyrolytic temperatures. Environ Pollut 159(10):2594–2601

    Article  CAS  Google Scholar 

  • Zhu DQ, Pignatello JJ (2005) Characterization of aromatic compound sorptive interactions with black carbon (charcoal) assisted by graphite as a model. Environ Sci Technol 39(7):2033–2041

    Article  CAS  Google Scholar 

  • Zhu DQ, Hyun SH, Pignatello JJ, Lee LS (2004) Evidence for pi-pi electron donor-acceptor interactions between pi-donor aromatic compounds and pi-acceptor sites in soil organic matter through pH effects on sorption. Environ Sci Technol 38(16):4361–4368

    Article  CAS  Google Scholar 

  • Zhu DQ, Kwon S, Pignatello JJ (2005) Adsorption of single-ring organic compounds to wood charcoals prepared under different thermochemical conditions. Environ Sci Technol 39(11):3990–3998

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The National High Technology Research and Development Program of the Ministry of Sciences and Technology of China (863 Program, 2013AA06A208), the Science and Technology Service Network Initiative of Chinese Academy of Sciences (STS, KFJ-EW-STS-091), and the National Science Foundation of China (41471404 and 51309214) were greatly acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mengfang Chen.

Additional information

Responsible editor: Guilherme L. Dotto

Electronic supplementary material

ESM 1

(DOCX 216 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Han, L., Qian, L., Yan, J. et al. Effects of the biochar aromaticity and molecular structures of the chlorinated organic compounds on the adsorption characteristics. Environ Sci Pollut Res 24, 5554–5565 (2017). https://doi.org/10.1007/s11356-016-8303-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-016-8303-8

Keywords

Navigation