Mechanochemical destruction of 4-bromochlorobenzene with CaO. Efficiency, kinetics, and mechanism

• Autorzy: Hu Jun , Feng Zhuohuan , Huang Zhiyong , Yu Jianming , Liu Jiansheng

Identyfikatory

DOI

10.37190/epe200205

• Języki publikacji: EN

Abstrakty

EN

The degradation of 4-bromochlorobenzene (4-BCB) containing both chlorine and bromine by mechanochemical destruction (MCD) using CaO powder was investigated. The degradation efficiency of 4-BCB almost achieved 100% after 2 h milling. The debromination rate (0.41 h^–1) was higher than the dechlorination rate (0.31 h⁻¹) which can be ascribed to the lower dissociation energy of C–Br bond than that of C–Cl bond in 4-BCB. The kinetic analysis demonstrates that nucleation growth was the control step of dehalogenation reactions. Additionally, the dehalogenation efficiency increased with increasing rotate speed and milling ball weight. The XRD and FT-IR spectra analysis manifests that the CaO powder was transformed to CaCl₂, CaBr₂, Ca(OH)₂, and CaCO₃. The identification of intermediates and analysis of Raman spectra indicates that the 4-BCB degradation by MCD treatment using CaO powder may occur through three pathways: (a) breakup of the benzene ring to form small molecular halogenated hydrocarbons and mineralization to form CO₂ and H₂O in sequence, (b) dehalogenation reaction to form benzene and monohalogenobenzene and addition reaction of halogen radicals to form dihalogenobenzenes in sequence; (c) polymerization reaction to form biphenyl, halogenated biphenyl, and graphite.

Słowa kluczowe

EN

calcium oxide; 4-bromochlorobenzene; mechanochemical destruction; kinetics

PL

tlenek wapnia; 4-bromochlorobenzen; niszczenie monochemiczne; kinetyka

• Wydawca: Oficyna Wydawnicza Politechniki Wrocławskiej
• Czasopismo: Environment Protection Engineering
• Rocznik: 2020
• Tom: Vol. 46, nr 2
• Strony: 63--77
• Opis fizyczny: Bibliogr. 28 poz., tab., rys.

Twórcy

autor

Hu Jun

• College of Environment, Zhejiang University of Technology, 18 Chao-wang Road, Hangzhou 310 014, China

autor

Feng Zhuohuan

• College of Environment, Zhejiang University of Technology, 18 Chao-wang Road, Hangzhou 310 014, China

autor

Huang Zhiyong

• College of Environment, Zhejiang University of Technology, 18 Chao-wang Road, Hangzhou 310 014, China

autor

Yu Jianming

• College of Environment, Zhejiang University of Technology, 18 Chao-wang Road, Hangzhou 310 014, China
• Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, 18 Chao-wang Road, Hangzhou 310014, China

autor

Liu Jiansheng

• College of Environment, Zhejiang University of Technology, 18 Chao-wang Road, Hangzhou 310 014, China

Bibliografia

• [1] IKOMA Y., ANDO K., NAOI Y., AKIYAMA T., SUGIMORI A., Halogen selectivity in nickel salt-catalyzed cross-coupling of aryl grignard reagents with bromochlorobenzenes a novel synthetic method of un-symmetrical terphenyl, Synth. Commun., 1991, 21, 481−487.
• [2] ALI N., ALI L., MEHDI T., DIRTU A.C., AL-SHAMMARI F., NEELS H., COVACI A., Levels and profiles of organochlorines and flame retardants in car and house dust from Kuwait and Pakistan. Implication for human exposure via dust ingestion, Environ. Int., 2013, 55, 62−70.
• [3] CHANG F.C., CHIU T.C., YEN J.H., WANG Y.S., Dechlorination pathways of ortho-substituted PCBs by UV irradiation in n-hexane and their correlation to the charge distribution on carbon atom, Chemo-sphere, 2003, 51, 775–784.
• [4] TANGE L., DROHMANN D., Waste electrical and electronic equipment plastics with brominated flame retardants – from legislation to separate treatment – thermal processes, Polym. Degrad. Stab., 2005, 88, 35–40.
• [5] JUHASZ A.L., ALEER S., ADETUTU E.M., Predicting PAH bioremediation efficacy using bioaccessibility assessment tools: Validation of PAH biodegradation–bioaccessibility correlations, Int. Biodet. Biodegrad., 2014, 95, 320–329.
• [6] YU J.M., CAI W.J., CHEN J.M., FENG L., JIANG Y.F., Conversion characteristics and mechanism analysis of gaseous dichloromethane degraded by a VUV light in different reaction media, J. Environ. Sci., 2012, 24, 1777–1784.
• [7] YU J.M., CAI W.J., CHENG Z.W., CHEN J.M., Degradation of dichloromethane by an isolated strain Pandoraea pnomenusa and its performance in a biotrickling filter, J. Environ. Sci., 2014, 26, 1108–1117.
• [8] YU J.M., LIU Q., LIU L., CHEN J.M., Cloning and characterization of dichloromethane dehalogenase from Methylobacterium rhodesianum for dichloromethane degradation, Biorem. J., 2017, 21, 71–80.
• [9] ZHANG W., WANG H.Z., HUANG J., YU M., WANG F., ZHOU L.B., YU G., Acceleration and mechanistic studies of the mechano chemical dechlorination of HCB with iron powder and quartz sand, Chem. Eng. J., 2014, 239, 185–191.
• [10] ROWLANDS S.A., HALL A.K., MCCORMICK P.G., STREET R., HART G.F., EBELL G.F., DONECKER P., Destruction of toxic materials, Nature, 1994, 367, 223.
• [11] NOMURA Y., NAKAI S., HOSOMI M., Elucidation of degradation mechanism of dioxins during mechanochemical treatment, Environ. Sci. Technol., 2005, 39, 3799–3804.
• [12] DUSHKIN A.V., KARNATOVSKAIA L.M., CHABUEVA E.N., PAVLOV S.V., KOBRIN V.S., BOLDYREV V.V., KOBRINA V.N., GRASDHANNIKOV A.E., KNJAZEV V.V., STARICHENKO V.F., Solid-phase mechano-chemical synthesis of fluoroaromatic compounds, Synth. Commun., 2001, 31, 1041−1045.
• [13] NOMURA Y., AONO S., ARINO T., YAMAMOTO T., TERADA A., NOMA Y., HOSOMI M., Degradation of polychlorinated naphthalene by mechanochemical treatment, Chemosphere, 2013, 93, 2657–2661.
• [14] NAH I.W., HWANG K.Y., SHUL Y.G., Effect of metal and glycol on mechanochemical dechlorination of polychlorinated biphenyls (PCBs), Chemosphere, 2008, 73, 138–141.
• [15] XIAO X., ZENG Z., XIAO S., Behavior and products of mechano-chemical dechlorination of polyvinyl chloride and poly (vinylidene chloride), J. Hazard. Mater., 2008, 151, 118–124.
• [16] WANG Y., XU M., JIN J., HE S.J., LI M.Y., SUN Y.M., Concentrations and relationships between classes of persistent halogenated organic compounds in pooled human serum samples and air from Laizhou Bay, China, Sci. Total Environ., 2014, 482−483, 276−282.
• [17] ZHANG Q.W., MATSUMOTO H., SAITO F., BARON M., Debromination of hexabromobenzene by its cogrinding with CaO, Chemosphere, 2002, 48, 787–793.
• [18] MULAS G., LOISELLE S., SCHIFFINI L., COCCO G., The mechanochemical self-propagating reaction be-tween hexachlorobenzene and calcium hydride, J. Solid State Chem., 1997, 129, 263–270.
• [19] WATANABE H., ISHIDA Y., HAYAZAWA N., INOUYE Y., KAWATA S., Tip-enhanced near-field Raman analysis of tip-pressurized adenine molecule, Phys. Rev. B, 2004, 69, 155418.
• [20] RACZYŃSKA E.D., KRYGOWSKI T.M., ZACHARA J.E., OŚMIAŁOWSKI B., GAWINECKI R., Tautomeric equilibria, H-bonding and π-electron delocalization in o-nitrosophenol. A B3LYP/6–311+ G (2df, 2p) study, J. Phys. Org. Chem., 2005, 18, 892−897.
• [21] TANAKA Y., ZHANG Q.W., SAITO F., Mechanochemical dechlorination of trichlorobenzene on oxide surfaces, J. Phys. Chem. B, 2003, 107, 11091–11097.
• [22] LJACHOV N., Mechanical activation from the viewpoint of kinetic reaction mechanism, Proc. 1st Int. Conf. Mechanochem., Cambridge 1993, 93, 59−65.
• [23] CAGNETTA G., HUANG J., WANG B., DENG S.B., YU G., A comprehensive kinetic model for mechano-chemical destruction of persistent organic pollutants, Chem. Eng. J., 2016, 291, 30−38.
• [24] LU S.Y., HUANG J.X., PENG Z.,LI X.D., YAN J.H., Ball milling 2,4,6-trichlorophenol with calcium oxide: Dechlorination experiment and mechanism considerations, Chem. Eng. J., 2012, 195, 62−68.
• [25] WEI Y.L., YAN J.H., LU S.Y., LI X.D., Mechanochemical decomposition of pentachlorophenol by ball milling, J. Environ. Sci., 2009, 21, 1761−1768.
• [26] HALL A.K., HARROWFIELD J.M., HART R.J., MCCORMICK P.G., Mechanochemical reaction of DDT with calcium oxide, Environ. Sci. Technol., 1996, 30, 3401−3407.
• [27] KUZUYA M., NIWA J., YAMAUCHI Y., KONDO S.I., Mechanochemical reactions of plasma-induced sur-face radicals on polyethylene, J. Photopolym. Sci. Technol., 1994, 7, 315–318.
• [28] UGLOV V.V., KULESHOV A.K., SAMTSOV M.P., ASTASHINSAKAYA M.V., Raman light scattering in hydrogenated metal–carbon composite films, J. Appl. Spectry, 2006, 73, 388−393.