Skip to main content
SpringerLink
Log in

4(5)-Methylbenzotriazole: a review of the life-cycle of an emerging contaminant

  • Review paper
  • Published:
Reviews in Environmental Science and Bio/Technology Aims and scope Submit manuscript

Abstract

4(5)-Methylbenzotriazole (MeBT), also known as tolyltriazole is a widely used compound that effectively prevents the corrosion of many metals in acidic and saline aqueous solutions. This review summarizes the current body of knowledge related to MeBT including its uses, corrosion inhibition capabilities, chemical and toxicological properties, occurrence in the environment, and treatment and removal from water supplies. Key conclusions include: poor biodegradability of the 5-MeBT isomer and the recalcitrance of the 4-MeBT isomer leading to persistence in the environment, poor removal efficiencies in conventional water treatment facilities, and the generally unknown chronic effects of MeBT. The aim of this paper is to bring to light the relevant facts about MeBT in a concise manner so that we may make more informed decisions regarding its use and of the potential long-term environmental effects that it may cause.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Abu-Dalo M (2003) Electrochemical characterization of benzotriazole derivatives and their behavior in industrial waste treatment. Dissertation, Department of Civil, Environmental and Architectural Engineering, University of Colorado

  • Ashour EA, Hegazy HS (2003) Inhibitive effect of benzotriazole on the stress corrosion cracking of type 316 stainless steel in chloride and thiosulfate containing solutions. Anti Corros Methods Mater 50:291–295. doi:10.1108/00035590310482532

    Article  CAS  Google Scholar 

  • Bereket G, Pinarbasi A (2004) Electrochemical thermodynamic and kinetic studies of the behavior of aluminum in hydrochloric acid containing various benzotriazole derivatives. Corros Eng Sci Technol 39(4):308. doi:10.1179/174327804X13136

    Article  CAS  Google Scholar 

  • Breedveld GD, Roseth R, Sparrevik M, Harnik T, Hem L (2003) Persistence of the de-icing additive benzotriazole at an abandoned airport. Water Air Soil Pollut Focus 3:91–101. doi:10.1023/A:1023961213839

    Article  CAS  Google Scholar 

  • Cancilla D, Martinez J, VanAggelen GC (1998) Detection of aircraft deicing/antiicing fluid additives in a perched water monitoring well at an international airport. Environ Sci Technol 32:3834–3835

    Article  CAS  Google Scholar 

  • Cancilla D, Baird JC, Geis SW, Corsi SR (2003) Studies of the environmental fate and effect of aircraft deicing fluids: detection of 5-methyl-1h-benzotriazole in the fatthead minnow (Pimephales promelas). Environ Toxicol Chem 22:134–140. doi:10.1002/etc.5620220117

    Article  CAS  Google Scholar 

  • Castro S, Davis LC, Erickson LE (2001) Phytodegradation kinetics of methyl benzotriazole. In: Conference on environmental research proceedings, Manhattan, Kansas

  • Chadwick D, Hashemi T (1978) Adsorbed corrosion inhibitors studied by electron spectroscopy: benzotriazoles on copper and copper alloys. Corros Sci 18:39–51. doi:10.1016/S0010-938X(78)80074-2

    Article  CAS  Google Scholar 

  • Cornell J (2001) The environmental impact of 4(5)-methylbenzotriazole from aircraft deicing operations. Dissertation, Department of Civil, Environmental and Architectural Engineering, University of Colorado

  • Cornell J, Pillard D, Hernandez M (1998) Chemical components of aircraft deicer fluid; how they affect propylene glycol degradation rates and deicing waste stream toxicity. In: WEFTEC proceedings, Orlando, Florida

  • Cornell J, Pillard D, Hernandez M (2000) Comparative measures of the toxicity of component chemicals in aircraft deicing fluids. Environ Toxicol Chem 19(4):1465–1472. doi:10.1002/etc.5620190601

    Article  CAS  Google Scholar 

  • Davis L, Santodanato J, Howard P, Saxena J (1977) Investigation of selected potential environmental contaminants: benzotriazoles. USEPA report, Washington, DC

  • DeMonbrun JR, Schmitt CR, Schreyer JM (1980) Patent no. 4,237,090. United States of America

  • Downs WR (1968) Chemically induced ignition in aircraft and spacecraft electrical circuitry by glycol/water solutions. NASA technical note TN D-4327

  • Environment Protection and Heritage Council, National Heather and Medical Research Council, Natural Resource Management Ministerial Council (2008) Australian guidelines for water recycling: augmentation of drinking water supplies. Australian Environment Protection and Heritage Council

  • Focazio MJ, Kolpin DW, Barnes KK, Furlong ET, Meyer MET, Zaugg SD, Barber LB, Thurman ME (2008) A national reconnaissance for pharmaceuticals and other organic wastewater contaminants in the United States—II) Untreated drinking water sources. Sci Total Environ 402:201–216. doi:10.1016/j.scitotenv.2008.02.021

    Article  CAS  Google Scholar 

  • Frignani A, Tommesani L, Brunoro G, Monticelli C, Fogagnolo M (1999) Influence of the alkyl chain on the protective effects of 1, 2, 3-benzotriazole towards copper corrosion. Part I: inhibition of the anodic and cathodic reactions. Corros Sci 41:1205–1215. doi:10.1016/S0010-938X(98)00191-7

    Article  CAS  Google Scholar 

  • Gerengi H, Kazimeirz D, Pawel S, Gozen B, Ryl J (2010) Investigation effect of benzotriazole on the corrosion of brass-MM55 alloy in artificial seawater by dynamic EIS. J Solid State Electrochem 14:897–902. doi:10.1007/s10008-009-0923-1

    Article  CAS  Google Scholar 

  • Giger W, Schaffner C, Kohler HE (2006) Benzotriazole and tolyltriazole as aquatic contaminants. 1. Input and occurrence in rivers and lakes. Environ Sci Technol 40:7186–7192. doi:10.1021/es061565j

    Article  CAS  Google Scholar 

  • Gomma (1998) Influence of copper cation on inhibition of corrosion for steel in presence of benzotriazole in sulfuric acid. Mater Chem Phys 55:131–138. doi:10.1016/S0254-0584(98)00084-4

    Article  CAS  Google Scholar 

  • Gruden C, Hernandez M (2002) Anaerobic digestion of aircraft deicing fluid wastes: interactions and toxicity of corrosion inhibitors and surfactants. Water Environ Res 74:149–158

    Article  CAS  Google Scholar 

  • Gruden C, Dow S, Hernandez M (2001) Fate and toxicity of aircraft deicing fluid additives through anaerobic digestion. Water Environ Res 73:72–79. doi:10.2175/106143001X138714

    Article  CAS  Google Scholar 

  • Harris CA, Routledge EJ, Schaffner C, Brian JV, Giger W, Sumpter JP (2007) Benzotriazole is antiestrogenic in vitro but not in vivo. Environ Toxicol Chem 26:2367–2372. doi:10.1897/06-587R.1

    Article  CAS  Google Scholar 

  • Health Council of the Netherlands: Dutch Expert Committee on Occupational Standards (2000) 1, 2, 3-Benzotriazole. Health Council of the Netherlands, The Hague

    Google Scholar 

  • Hem LJ, Hartnik T, Roseth R, Gijs DB (2003) Photochemical degradation of benzotriazole. J Environ Sci Health 38:471–481. doi:10.1081/ESE-120016907

    Article  Google Scholar 

  • Huber MM, Gobel A, Joss A, Hermann N, Loffler D, Mcardell CS, Reid A, Siegrist H, Ternes TA, von Gunten U (2005) Oxidation of pharmaceuticals during ozonation of municipal wastewater effluents: a pilot study. Environ Sci Technol 39:4290–4299. doi:10.1021/es048396s

    Article  CAS  Google Scholar 

  • Janna H, Scrimshaw MD, Williams RJ, Churchley J, Sumpter JP (2011) From dishwasher to tap? Xenobiotic substances benzotriazole and tolyltriazole in the environment. Environ Sci Technol 45:3858–3864. doi:10.1021/es103267g

    Article  CAS  Google Scholar 

  • Kiss A, Fries E (2009) Occurrence of benzotriazoles in the rivers of Main, Hengstbach and Hegbach (Germany). Environ Sci Pollut Res 16:702–710. doi:10.1007/s11356-009-0179-4

    Article  CAS  Google Scholar 

  • Kiss A, Fries E (2012) Seasonal source influence on river mass flows of benzotriazoles. J Environ Monit 14:697–703. doi:10.1039/c2em10826g

    Article  CAS  Google Scholar 

  • Kolpin DW, Furlong ET, Meyer MET, Thuman ME, Zaugg SD, Barber LB, Buxton HT (2002) Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999–2000: a national reconnaissance. Environ Sci Technol 36:1202–1211

    Article  CAS  Google Scholar 

  • Korpics C (1974) Patent no. 3,791,855 & 3,803,049. United States of America

  • Liddel R (1959) Patent no. 2,877,188. United States of America

  • Liu Y, Ying G, Shareer A, Kookana RS (2011) Biodegradation of three selected benzotriazoles under aerobic and anaerobic conditions. Water Res 45:5005–5014. doi:10.1016/j.watres.2011.07.001

    Article  CAS  Google Scholar 

  • Lu F, Rao NM, Yang B, Hoots JE, Budrys RS (1994) Effect of halogenation on yellow metal corrosion—inhibition by triazoles. Corrosion 50:422–431. doi:10.5006/1.3293520

    Article  CAS  Google Scholar 

  • Matamoros V, Jover E, Bayona JM (2010) Occurrence and fate of benzothiazoles and benzotriazoles in constructed wetlands. Water Sci Technol 61:191–198. doi:10.2166/wst.2010.797

    Article  CAS  Google Scholar 

  • McNeill KS, Cancilla DA (2009) Detection of triazole deicing additives in soil samples from airports with low, mid, and large volume aircraft deicing activities. Bull Environ Contam Toxicol 82:265–269. doi:10.1007/s00128-008-9626-z

    Article  CAS  Google Scholar 

  • O’Brien IZ (2002) Biotransformation potential and uncoupling behavior of common benzotriazole-based corrosion inhibitors. Dissertation, Department of Civil, Environmental and Architectural Engineering, University of Colorado

  • O’Neal C (1976) Patent no. 3,985,503. United States of America

  • Pearson R (2000) Properties of methylbenzotriazole. PMC Specialties Group, Inc, Cincinnati, OH

    Google Scholar 

  • Pillard DA, Cornell JS, Dufresne DL, Hernandez MT (2001) Toxicity of benzotriazole and benzotriazole derivatives to three aquatic species. Water Res 35:557–560

    Article  CAS  Google Scholar 

  • Rao NL (1996) Patent no. 5503775. United States of America

  • Ravichandran R, Nanjundan S, Rajendran N (2004) Effect of benzotriazole derivatives on the corrosion of brrass in NaCl solutions. Appl Surf Sci 236:241–250. doi:10.1016/j.apsusc.2004.04.025

    Article  CAS  Google Scholar 

  • Reemtsma T, Weis S, Mueller J, Petrovic M, Gonzales S, Barcelo D, Ventura F, Knepper TP (2006) Polar pollutant entry into the water cycle by municipal wastewater: a European perspective. Environ Sci Technol 40:5451–5458

    Article  CAS  Google Scholar 

  • Reemtsma T, Miehe U, Duennbier U, Jekel M (2010) Polar pollutants in municipal wastewater and the water cycle: occurrence and removal of benzotriazoles. Water Res 44:596–604. doi:10.1016/j.watres.2009.07.016

    Article  CAS  Google Scholar 

  • Thomas S, Venkateswaran S, Kapoor S, Cunha RD, Mukherjee T (2004) Surface enhanced Raman scattering of benzotriazole: a molecular orientational study. Spectrochim Acta A 60:25–29

    Article  CAS  Google Scholar 

  • USEPA (1999) EPA Guidance Manual: Alternative Disinfectants and Oxidants

  • USEPA (2000) Preliminary data summary: airport deicing operations. EPA Office of Water, Washington, DC

    Google Scholar 

  • USEPA (2009) Final contaminant candidate list 3 chemicals: screening to PCCL. USEPA Office of Water

  • USEPA (2012, March 22). High production volume information system (HPVIS). http://www.epa.gov/hpvis/. Accessed 15 Dec 2012

  • van Leerdam JA, Hogeboom AC, van der Koi MME, de Voogt P (2009) Determination of polar 1H-benzotriazoles and benzothiazoles in water by solid-phase extraction and liquid chromatography. Int J Mass Spectrom 282:99–107. doi:10.1016/j.ijms.2009.02.018

    Article  Google Scholar 

  • Verheyen V, Cruickshank A, Wild K, Heaven MW, McGee R, Watkins M, Nash D (2009) Soluble, semivolatile phenol and nitrogen compounds in milk-processing wastewaters. J Dairy Sci 92:3483–3493. doi:10.3168/jds.2009-2217

    Article  Google Scholar 

  • Voutsa D, Harmann P, Schaffner C, Giger W (2006) Benzotriazoles, alkylphenols and bisphenol A in municipal wastewaters and in the Glatt River, Switzerland. Environ Sci Pollut Res 13:333–341

    Article  CAS  Google Scholar 

  • Weiss S, Jutta J, Reemtsma T (2006) Discharge of three benzotriazole corrosion inhibitors with municipal wastewater and improvements by membrane bioreactor treatment and ozonation. Environ Sci Technol 40:7193–7199

    Article  CAS  Google Scholar 

  • Wells MJM, Fono LJ, Pellegrin M (2007) Emerging pollutants. Water Environ Res 79:2192–2209. doi:10.2175/106143007X218719

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. 1155 Marine St. #104, Boulder, CO, 80302, USA

    Nicholas M. Dummer

Authors
  1. Nicholas M. Dummer
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nicholas M. Dummer.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dummer, N.M. 4(5)-Methylbenzotriazole: a review of the life-cycle of an emerging contaminant. Rev Environ Sci Biotechnol 13, 53–61 (2014). https://doi.org/10.1007/s11157-013-9318-y

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11157-013-9318-y

Keywords

Search

Navigation