Quaternary ammonium compounds (QACs): A review on occurrence, fate and toxicity in the environment

Science of the Total Environment

Volumn 518-519, Issue , 2015, Pages 352-362

  Zhang, Chang ^a   Cui, Fang ^a   Zeng, Guang ming ^a   Jiang, Min ^a   Yang, Zhong zhu ^a   Yu, Zhi gang ^a   Zhu, Meng ying ^a   Shen, Liu qing ^a  

^a HUNAN UNIVERSITY   (China)

Author keywords

Biodegradation; Determination; Quaternary ammonium compounds (QACs); Sorption; Toxicity

Indexed keywords

AMMONIUM COMPOUNDS; ANIONIC SURFACTANTS; AQUATIC ORGANISMS; BIODEGRADATION; DISSOLVED OXYGEN; EFFLUENT TREATMENT; LEAD REMOVAL (WATER TREATMENT); MICROBIOLOGY; MICROORGANISMS; SEWAGE SLUDGE; SEWAGE TREATMENT PLANTS; SORPTION; SURFACE WATERS; TOXICITY; WASTEWATER TREATMENT;

ANTHROPOGENIC ACTIVITY; ANTIBIOTIC RESISTANCE; DETERMINATION; DISSOLVED OXYGEN CONCENTRATIONS; ENVIRONMENTAL COMPARTMENT; QUATERNARY AMMONIUM COMPOUND; WASTEWATER TREATMENT PLANTS; WASTEWATER TREATMENT SYSTEM;

EFFLUENTS;

ANIONIC SURFACTANT; DISSOLVED OXYGEN; QUATERNARY AMMONIUM DERIVATIVE; SURFACE WATER; WASTE WATER; WATER POLLUTANT;

AMMONIUM COMPOUND; ANTHROPOGENIC SOURCE; BIODEGRADATION; ENVIRONMENTAL FATE; HUMAN ACTIVITY; TOXICITY; WASTE FACILITY; WASTEWATER; WATER TREATMENT;

ALGA; ANALYTIC METHOD; ANTIBIOTIC RESISTANCE; AQUATIC SPECIES; BIODEGRADABILITY; BIODEGRADATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); CORRELATION ANALYSIS; ECOTOXICITY; ELECTROSPRAY MASS SPECTROMETRY; ENVIRONMENTAL IMPACT ASSESSMENT; FISH; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; MICROORGANISM; NONHUMAN; PRIORITY JOURNAL; REVIEW; RISK ASSESSMENT; ROTIFERA; SEDIMENT; SEWAGE EFFLUENT; SLUDGE; SOLID PHASE EXTRACTION; TANDEM MASS SPECTROMETRY; WASTE WATER; WASTE WATER TREATMENT PLANT; WATER ANALYSIS; ANALYSIS; ANIMAL; BIOREMEDIATION; ENVIRONMENTAL MONITORING; TOXICITY; WATER POLLUTANT;

ALGAE; DAPHNIIDAE;

ANIMALS; AQUATIC ORGANISMS; BIODEGRADATION, ENVIRONMENTAL; ENVIRONMENTAL MONITORING; QUATERNARY AMMONIUM COMPOUNDS; WASTE WATER; WATER POLLUTANTS, CHEMICAL;

EID: 84924533662     PISSN: 00489697     EISSN: 18791026     Source Type: Journal    
DOI: 10.1016/j.scitotenv.2015.03.007     Document Type: Review

References (104)

1. Bassarab P., Williams D., Dean J.R., Ludkin E., Perry J.J. Determination of quaternary ammonium compounds in seawater samples by solid-phase extraction and liquid chromatography-mass spectrometry. J. Chromatogr. A 2011, 1218:673-677. 10.1016/j.chroma.2010.11.088.
2. Boethling R.S. Environmental fate and toxicity in wastewater treatment of quaternary ammonium surfactants. Water Res. 1984, 18:1061-1076. 10.1016/0043-1354(84)90220-3.
3. Breen D., Horner J.M., Bartle K.D., Clifford A.A., Waters J., Lawrence J.G. Supercritical fluid extraction and off-line HPLC analysis of cationic surfactants from dried sewage sludge. Water Res. 1996, 30:476-480. 10.1016/0043-1354(95)00185-9.
4. Brycki B., Waligorska M., Szulc A. The biodegradation of monomeric and dimeric alkylammonium surfactants. J. Hazard. Mater. 2014, 280:797-815. 10.1016/j.jhazmat.2014.08.021.
5. Buffet-Bataillon S., Tattevin P., Bonnaure-Mallet M., Jolivet-Gougeon A. Emergence of resistance to antibacterial agents: the role of quaternary ammonium compounds-a critical review. Int. J. Antimicrob. Agents 2012, 39:381-389. 10.1016/j.ijantimicag.2012.01.011.
6. Chen Y., Geurts M., Sjollema S.B., Kramer N.I., Hermens J.L., Droge S.T. Acute toxicity of the cationic surfactant C12-benzalkonium in different bioassays: how test design affects bioavailability and effect concentrations. Environ. Toxicol. Chem. 2014, 33:606-615. 10.1002/etc.2465.
7. Chiaia-Hernandez A.C., Krauss M., Hollender J. Screening of lake sediments for emerging contaminants by liquid chromatography atmospheric pressure photoionization and electrospray ionization coupled to high resolution mass spectrometry. Environ. Sci. Technol. 2013, 47:976-986. 10.1021/es303888v.
8. Clara M., Scharf S., Scheffknecht C., Gans O. Occurrence of selected surfactants in untreated and treated sewage. Water Res. 2007, 41:4339-4348. 10.1016/j.watres.2007.06.027.
9. Clarke B.O., Smith S.R. Review of 'emerging' organic contaminants in biosolids and assessment of international research priorities for the agricultural use of biosolids. Environ. Int. 2011, 37:226-247. 10.1016/j.envint.2010.06.004.
10. Comber S.D., Rule K.L., Conrad A.U., Hoss S., Webb S.F., Marshall S. Bioaccumulation and toxicity of a cationic surfactant (DODMAC) in sediment dwelling freshwater invertebrates. Environ. Pollut. 2008, 153:184-191. 10.1016/j.envpol.2007.07.032.
11. Deutschle T., Porkert U., Reiter R., Keck T., Riechelmann H. In vitro genotoxicity and cytotoxicity of benzalkonium chloride. Toxicol. In Vitro 2006, 20:1472-1477. 10.1016/j.tiv.2006.07.006.
12. Ding W.H., Liao Y.H. Determination of alkylbenzyldimethylammonium chlorides in river water and sewage effluent by solid-phase extraction and gas chromatography/mass spectrometry. Anal. Chem. 2001, 73:36-40. 10.1021/ac000655i.
13. Ding W.H., Tsai P.C. Determination of alkyltrimethylammonium chlorides in river water by gas chromatography/ion trap mass spectrometry with electron impact and chemical ionization. Anal. Chem. 2003, 75:1792-1797. 10.1021/ac020536y.
14. European Commission European Union Risk Assessment Report: Dimethyldioctadecylammonium Chloride (DODMAC) 2002, vol. 14. (EUR 20397 EN. http://echa.europa.eu/documents/10162/6434698/orats_summary_dimethyldioctadecylammoniumchl_en.pdf).
15. Ferk F., Misik M., Hoelzl C., Uhl M., Fuerhacker M., Grillitsch B., et al. Benzalkonium chloride (BAC) and dimethyldioctadecyl-ammonium bromide (DDAB), two common quaternary ammonium compounds, cause genotoxic effects in mammalian and plant cells at environmentally relevant concentrations. Mutagenesis 2007, 22:363-370. 10.1093/mutage/gem027.
16. Fernández Cirelli A., Ojeda C., Castro M.J.L., Salgot M. Surfactants in sludge-amended agricultural soils: a review. Environ. Chem. Lett. 2008, 6:135-148. 10.1007/s10311-008-0146-1.
17. Fernández P., Alder A.C., Suter M., Giger W. Determination of the quaternary ammonium surfactant ditallowdimethylammonium in digested sludges and marine sediments by supercritical fluid extraction and liquid chromatography with postcolumn ion-pair formation. Anal. Chem. 1996, 68:921-929. 10.1021/ac9505482.
18. Ferrer I., Furlong E.T. Identification of alkyl dimethylbenzylammonium surfactants in water samples by solid phase extraction followed by ion trap LC/MS and LC/MS/MS. Environ. Sci. Technol. 2001, 35:2583-2588. 10.1021/es001742v.
19. Ferrer I., Furlong E.T. Accelerated solvent extraction followed by on-line solid-phase extraction coupled to ion trap LC/MS/MS for analysis of benzalkonium chlorides in sediment samples. Anal. Chem. 2002, 74:1275-1280. 10.1021/ac010969l.
20. Games L.M., King J.E. Fate and distribution of a quaternary ammonium surfactant, octadecyltrimethylammonium chloride (OTAC), in wastewater treatment. Environ. Sci. Technol. 1982, 16:483-488. 10.1021/es00102a011.
21. García M.T., Campos E., Sanchez-Leal J., Ribosa I. Effect of the alkyl chain length on the anaerobic biodegradability and toxicity of quaternary ammonium based surfactants. Chemosphere 1999, 38:3473-3483. 10.1016/S0045-6535(98)00576-1.
22. García M.T., Campos E., Sanchez-Leal J., Ribosa I. Anaerobic degradation and toxicity of commercial cationic surfactants in anaerobic screening tests. Chemosphere 2000, 41:705-710. 10.1016/S0045-6535(99)00455-5.
23. García M.T., Ribosa I., Guindulain T., Sánchez-Leal J., Vives-Rego J. Fate and effect of monoalkyl quaternary ammonium surfactants in the aquatic environment. Environ. Pollut. 2001, 111:169-175. 10.1016/S0269-7491(99)00322-X.
24. Gaze W.H., Abdouslam N., Hawkey P.M., Wellington E.M. Incidence of class 1 integrons in a quaternary ammonium compound-polluted environment. Antimicrob. Agents Chemother. 2005, 49:1802-1807. 10.1128/AAC.49.5.1802-1807.2005.
25. Ge F., Xu Y., Zhu R., Yu F., Zhu M., Wong M. Joint action of binary mixtures of cetyltrimethyl ammonium chloride and aromatic hydrocarbons on Chlorella vulgaris. Ecotoxicol. Environ. Saf. 2010, 73:1689-1695. 10.1016/j.ecoenv.2010.06.003.
26. Gerike P., Klotz H., Kooijman J.G.A., Matthijs E., Waters J. The determination of dihardened tallow dimethyl ammonium compounds (DHTDMAC) in environmental matrices using trace enrichment techniques and high performance liquid chromatography with conductometric detection. Water Res. 1994, 28:147-154. 10.1016/0043-1354(94)90128-7.
27. Giolando S.T., Rapaport R.A., Larson R.J., Federle T.W., Stalmans M., Masscheleyn P. Environmental fate and effects of DEEDMAC: a new rapidly biodegradable cationic surfactant for use in fabric softeners. Chemosphere 1995, 30:1067-1083. 10.1016/0045-6535(95)00005-S.
28. Grabinska-Sota E. Genotoxicity and biodegradation of quaternary ammonium salts in aquatic environments. J. Hazard. Mater. 2011, 195:182-187. 10.1016/j.jhazmat.2011.08.026.
29. Hajaya M.G., Pavlostathis S.G. Fate and effect of benzalkonium chlorides in a continuous-flow biological nitrogen removal system treating poultry processing wastewater. Bioresour. Technol. 2012, 118:73-81. 10.1016/j.biortech.2010.05.050.
30. Hajaya M.G., Pavlostathis S.G. Modeling the fate and effect of benzalkonium chlorides in a continuous-flow biological nitrogen removal system treating poultry processing wastewater. Bioresour. Technol. 2013, 130:278-287. 10.1016/j.biortech.2012.11.103.
31. Hajaya M.G., Tezel U., Pavlostathis S.G. Effect of temperature and benzalkonium chloride on nitrate reduction. Bioresour. Technol. 2011, 102:5039-5047. 10.1016/j.biortech.2011.01.080.
32. Hegstad K., Langsrud S., Lunestad B.T., Scheie A.A., Sunde M., Yazdankhah S.P. Does the wide use of quaternary ammonium compounds enhance the selection and spread of antimicrobial resistance and thus threaten our health?. Microb. Drug Resist. 2010, 16:91-104. 10.1089/mdr.2009.0120.
33. Im S.H., Jeong Y.H., Ryoo J.J. Simultaneous analysis of anionic, amphoteric, nonionic and cationic surfactant mixtures in shampoo and hair conditioner by RP-HPLC/ELSD and LC/MS. Anal. Chim. Acta 2008, 619:129-136. 10.1016/j.aca.2008.03.058.
34. Inacio A.S., Costa G.N., Domingues N.S., Santos M.S., Moreno A.J., Vaz W.L., et al. Mitochondrial dysfunction is the focus of quaternary ammonium surfactant toxicity to mammalian epithelial cells. Antimicrob. Agents Chemother. 2013, 57:2631-2639. 10.1128/AAC.02437-12.
35. Ioannou C.J., Hanlon G.W., Denyer S.P. Action of disinfectant quaternary ammonium compounds against Staphylococcus aureus. Antimicrob. Agents Chemother. 2007, 51:296-306. 10.1128/AAC. 00375-06.
36. Ishikawa S., Matsumura Y., Yoshizako F., Tsuchido T. Characterization of a cationic surfactant-resistant mutant isolated spontaneously from Escherichia coli. J. Appl. Microbiol. 2002, 92:261-268. 10.1046/j.1365-2672.2002.01526.x.
37. Ismail Z.Z., Tezel U., Pavlostathis S.G. Sorption of quaternary ammonium compounds to municipal sludge. Water Res. 2010, 44:2303-2313. 10.1016/j.watres.2009.12.029.
38. Jing G., Zhou Z., Zhuo J. Quantitative structure-activity relationship (QSAR) study of toxicity of quaternary ammonium compounds on Chlorella pyrenoidosa and Scenedesmus quadricauda. Chemosphere 2012, 86:76-82. 10.1016/j.chemosphere.2011.09.021.
39. Kreuzinger N., Fuerhacker M., Scharf S., Uhl M., Gans O., Grillitsch B. Methodological approach towards the environmental significance of uncharacterized substances - quaternary ammonium compounds as an example. Desalination 2007, 215:209-222. 10.1016/j.desal.2006.10.036.
40. Kümmerer K., Eitel A., Braun U., Hubner P., Daschner F., Mascart G., et al. Analysis of benzalkonium chloride in the effluent from European hospitals by solid-phase extraction and high-performance liquid chromatography with post-column ion-pairing and fluorescence detection. J. Chromatogr. A 1997, 774:281-286. 10.1016/S0021-9673(97)00242-2.
41. Lara-Martín P.A., Li X.L., Bopp R.F., Brownawell B.J. Occurrence of alkyltrimethylammonium compounds in urban estuarine sediments: behentrimonium as a new emerging contaminant. Environ. Sci. Technol. 2010, 44:7569-7575. 10.1021/es101169a.
42. Larsen S.T., Verder H., Nielsen G.D. Airway effects of inhaled quaternary ammonium compounds in mice. Basic Clin. Pharmacol. 2012, 110:537-543. 10.1111/j.1742-7843.2011.00851.x.
43. Li X., Brownawell B.J. Analysis of quaternary ammonium compounds in estuarine sediments by LC-ToF-MS: very high positive mass defects of alkylamine ions as powerful diagnostic tools for identification and structural elucidation. Anal. Chem. 2009, 81:7926-7935. 10.1021/ac900900y.
44. Li X., Brownawell B.J. Quaternary ammonium compounds in urban estuarine sediment environments-a class of contaminants in need of increased attention. Environ. Sci. Technol. 2010, 44:7561-7568. 10.1021/es1011669.
45. Li S., Zhao S. Spectrophotometric determination of cationic surfactants with benzothiaxolyldiazoaminoazobenzene. Anal. Chim. Acta 2004, 501:99-102. 10.1016/j.aca.2003.09.014.
46. Li X., Luo X., Mai B., Liu J., Chen L., Lin S. Occurrence of quaternary ammonium compounds (QACs) and their application as a tracer for sewage derived pollution in urban estuarine sediments. Environ. Pollut. 2014, 185:127-133. 10.1016/j.envpol.2013.10.028.
47. Liang Z., Ge F., Zeng H., Xu Y., Peng F., Wong M. Influence of cetyltrimethyl ammonium bromide on nutrient uptake and cell responses of Chlorella vulgaris. Aquat. Toxicol. 2013, 138-139:81-87. 10.1016/j.aquatox.2013.04.010.
48. 3+ ions. J. Appl. Microbiol. 2008, 104:396-402. 10.1111/j.1365-2672.2007.03591.x.
49. Liu H.-Y., Ding W.-H. Determination of homologues of quaternary ammonium surfactants by capillary electrophoresis using indirect UV detection. J. Chromatogr. A 2004, 1025:303-312. 10.1016/j.chroma.2003.10.108.
50. Martinez-Carballo E., Sitka A., Gonzalez-Barreiro C., Kreuzinger N., Furhacker M., Scharf S., et al. Determination of selected quaternary ammonium compounds by liquid chromatography with mass spectrometry. Part I. Application to surface, waste and indirect discharge water samples in Austria. Environ. Pollut. 2007, 145:489-496. 10.1016/j.envpol.2006.04.033.
51. Martinez-Carballo E., Gonzalez-Barreiro C., Sitka A., Kreuzinger N., Scharf S., Gans O. Determination of selected quaternary ammonium compounds by liquid chromatography with mass spectrometry. Part II. Application to sediment and sludge samples in Austria. Environ. Pollut. 2007, 146:543-547. 10.1016/j.envpol.2006.07.016.
52. Mc Cay P.H., Ocampo-Sosa A.A., Fleming G.T. Effect of subinhibitory concentrations of benzalkonium chloride on the competitiveness of Pseudomonas aeruginosa grown in continuous culture. Microbiology 2010, 156:30-38. 10.1099/mic.0.029751-0.
53. McBain A.J., Ledder R.G., Moore L.E., Catrenich C.E., Gilbert P. Effects of quaternary-ammonium-based formulations on bacterial community dynamics and antimicrobial susceptibility. Appl. Environ. Microbiol. 2004, 70:3449-3456. 10.1128/AEM.70.6.3449-3456.2004.
54. Melin V.E., Potineni H., Hunt P., Griswold J., Siems B., Werre S.R., et al. Exposure to common quaternary ammonium disinfectants decreases fertility in mice. Reprod. Toxicol. 2014, 50:163-170. 10.1016/j.reprotox.2014.07.071.
55. Merino F., Rubio S., Pérez-Bendito D. Solid-phase extraction of application to the concentration of benzalkonium surfactants in sewage and river water. Anal. Chem. 2003, 75:6799-6806. 10.1021/ac030224a.
56. Merino F., Rubio S., Pérez-Bendito D. Mixed aggregate-based acid-induced cloud-point extraction and ion-trap liquid chromatography-mass spectrometry for the determination of cationic surfactants in sewage sludge. J. Chromatogr. A 2003, 998.
57. Moore L.E., Ledder R.G., Gilbert P., McBain A.J. In vitro study of the effect of cationic biocides on bacterial population dynamics and susceptibility. Appl. Environ. Microbiol. 2008, 74:4825-4834. 10.1128/AEM.00573-08.
58. Nalecz-Jawecki G., Grabinska-Sota E., Narkiewicz P. The toxicity of cationic surfactants in four bioassays. Ecotoxicol. Environ. Saf. 2003, 54:87-91. 10.1016/S0147-6513(02)00025-8.
59. Nishihara T., Okamoto T., Nishiyama N. Biodegradation of didecyldimethylammonium chloride by Pseudomonas fluorescens TN4 isolated from activated sludge. J. Appl. Microbiol. 2000, 88:641-647. 10.1046/j.1365-2672.2000.01007.x.
60. Nishiyama N., Nishihara T. Biodegradation of dodecyl trimethyl ammonium bromide by Pseudomonas fluorescens F7 and F2 isolated from activated sludge. Microbes Environ. 2002, 17:164-169. 10.1264/jsme2.17.164.
61. Nishiyama N., Toshima Y., Ikeda Y. Biodegradation of alkyltrimethylammonium salts in activated sludge. Chemosphere 1995, 30:593-603. 10.1016/0045-6535(94)00406-K.
62. Norberg J., Thordarson E., Mathiasson L., Jonsson J.A. Microporous membrane liquid-liquid extraction coupled on-line with normal-phase liquid chromatography for the determination of cationic surfactants in river and waste water. J. Chromatogr. A 2000, 869:523-529. 10.1016/S0021-9673(99)01219-4.
63. Núñez O., Moyano E., Galceran M.T. Determination of quaternary ammonium biocides by liquid chromatography-mass spectrometry. J. Chromatogr. A 2004, 1058:89-95. 10.1016/j.chroma.2004.08.085.
64. Núñez O., Moyano E., Galceran M.T. Time-of-flight high resolution versus triple quadrupole tandem mass spectrometry for the analysis of quaternary ammonium herbicides in drinking water. Anal. Chim. Acta 2004, 525:183-190. 10.1016/j.aca.2004.08.006.
65. Oh S., Tandukar M., Pavlostathis S.G., Chain P.S., Konstantinidis K.T. Microbial community adaptation to quaternary ammonium biocides as revealed by metagenomics. Environ. Microbiol. 2013, 15:2850-2864. 10.1111/1462-2920.12154.
66. Olkowska E., Polkowska Z., Namiesnik J. A solid phase extraction-ion chromatography with conductivity detection procedure for determining cationic surfactants in surface water samples. Talanta 2013, 116:210-216. 10.1016/j.talanta.2013.04.083.
67. Patrauchan M.A., Oriel P.J. Degradation of benzyldimethylalkylammonium chloride by Aeromonas hydrophila sp.K. J. Appl. Microbiol. 2003, 94:266-272. 10.1046/j.1365-2672.2003.01829.x.
68. Peng X.T., Shi Z.G., Feng Y.Q. Rapid and high-throughput determination of cationic surfactants in environmental water samples by automated on-line polymer monolith microextraction coupled to high performance liquid chromatography-mass spectrometry. J. Chromatogr. A 2011, 1218:3588-3594. 10.1016/j.chroma.2011.04.009.
69. Pérez P., Fernández E., Beiras R. Toxicity of benzalkonium chloride on monoalgal cultures and natural assemblages of marine phytoplankton. Water Air Soil Pollut. 2009, 201:319-330. 10.1007/s11270-008-9947-x.
70. Pruden A., Pei R.T., Storteboom H., Carlson K.H. Antibiotic resistance genes as emerging contaminants: studies in northern Colorado. Environ. Sci. Technol. 2006, 40:7445-7450. 10.1021/es060413l.
71. Qin Y., Zhang G.Y., Kang B.A., Zhao Y.M. Primary aerobic biodegradation of cationic and amphoteric surfactants. J. Surfactant Deterg. 2005, 8:55-58. 10.1007/s11743-005-0330-x.
72. Qv X.Y., Jiang J.G. Toxicity evaluation of two typical surfactants to Dunaliella bardawil, an environmentally tolerant alga. Environ. Toxicol. Chem. 2013, 32:426-433. 10.1002/etc.2073.
73. Ren R., Li K., Zhang C., Liu D., Sun J. Biosorption of tetradecyl benzyl dimethyl ammonium chloride on activated sludge: kinetic, thermodynamic and reaction mechanisms. Bioresour. Technol. 2011, 102:3799-3804. 10.1016/j.biortech.2010.12.032.
74. Ruan T., Song S., Wang T., Liu R., Lin Y., Jiang G. Identification and composition of emerging quaternary ammonium compounds in municipal sewage sludge in China. Environ. Sci. Technol. 2014, 48:4289-4297. 10.1021/es4050314.
75. Sanchez-Fortun S., Marva F., D'Ors A., Costas E. Inhibition of growth and photosynthesis of selected green microalgae as tools to evaluate toxicity of dodecylethyldimethyl-ammonium bromide. Ecotoxicology 2008, 17:229-234. 10.1007/s10646-007-0189-2.
76. Sandbacka M., Christianson I., Isomaa B. The acute toxicity of surfactants on fish cells, daphnia magna and fish - a comparative study. Toxicol. in Vitro 2000, 14:61-68. 10.1016/S0887-2333(99)00083-1.
77. Sarkar B., Megharaj M., Xi Y., Krishnamurti G.S., Naidu R. Sorption of quaternary ammonium compounds in soils: implications to the soil microbial activities. J. Hazard. Mater. 2010, 184:448-456. 10.1016/j.jhazmat.2010.08.055.
78. Sarkar B., Megharaj M., Shanmuganathan D., Naidu R. Toxicity of organoclays to microbial processes and earthworm survival in soils. J. Hazard. Mater. 2013, 261:793-800. 10.1016/j.jhazmat.2012.11.061.
79. Scott J.M., Jones M.N. The biodegradation of surfactants in the environment. Biochim. Biophys. Acta 2000, 1508:235-251. 10.1016/S0304-4157(00)00013-7.
80. Sutterlin H., Alexy R., Coker A., Kummerer K. Mixtures of quaternary ammonium compounds and anionic organic compounds in the aquatic environment: elimination and biodegradability in the closed bottle test monitored by LC-MS/MS. Chemosphere 2008, 72:479-484. 10.1016/j.chemosphere.2008.03.008.
81. Sutterlin H., Alexy R., Kummerer K. The toxicity of the quaternary ammonium compound benzalkonium chloride alone and in mixtures with other anionic compounds to bacteria in test systems with Vibrio fischeri and Pseudomonas putida. Ecotoxicol. Environ. Saf. 2008, 71:498-505. 10.1016/j.ecoenv.2007.12.015.
82. Takenaka S., Tonoki T., Taira K., Murakami S., Aoki K. Adaptation of Pseudomonas sp. strain 7-6 to quaternary ammonium compounds and their degradation via dual pathways. Appl. Environ. Microbiol. 2007, 73:1797-1802. 10.1128/AEM.02426-06.
83. Tandukar M., Oh S., Tezel U., Konstantinidis K.T., Pavlostathis S.G. Long-term exposure to benzalkonium chloride disinfectants results in change of microbial community structure and increased antimicrobial resistance. Environ. Sci. Technol. 2013, 47:9730-9738. 10.1021/es401507k.
84. Terzic S., Ahel M. Nontarget analysis of polar contaminants in freshwater sediments influenced by pharmaceutical industry using ultra-high-pressure liquid chromatography-quadrupole time-of-flight mass spectrometry. Environ. Pollut. 2011, 159:557-566. 10.1016/j.envpol.2010.10.009.
85. Tezel U. Fate and Effect of Quaternary Ammonium Compounds in Biological Systems 2009, (Ph.D. Dissertation), Georgia Institute of Technology, Atlanta, GA.
86. Tezel U., Pavlostathis S.G. Transformation of benzalkonium chloride under nitrate reducing conditions. Environ. Sci. Technol. 2009, 43:1342-1348. 10.1021/es802177f.
87. Tezel U., Pierson J.A., Pavlostathis S.G. Fate and effect of quaternary ammonium compounds on a mixed methanogenic culture. Water Res. 2006, 40:3660-3668. 10.1016/j.watres.2006.06.019.
88. Tezel U., Pierson J.A., Pavlostathis S.G. Effect of polyelectrolytes and quaternary ammonium compounds on the anaerobic biological treatment of poultry processing wastewater. Water Res. 2007, 41:1334-1342. 10.1016/j.watres.2006.12.005.
89. Tezel U., Pierson J.A., Pavlostathis S.G. Effect of didecyl dimethyl ammonium chloride on nitrate reduction in a mixed methanogenic culture. Water Sci. Technol. 2008, 57:541-546. 10.2166/wst.2008.068.
90. Tezel U., Tandukar M., Martinez R.J., Sobecky P.A., Pavlostathis S.G. Aerobic biotransformation of n-tetradecylbenzyldimethylammonium chloride by an enriched Pseudomonas spp. community. Environ. Sci. Technol. 2012, 46:8714-8722. 10.1021/es300518c.
91. Thomas P.C., Velthoven K., Geurts M., van Wijk D. Bioavailability and detoxification of cationics: II. Relationship between toxicity and CEC of cationic surfactants on Caenorhabditis elegans (Nematoda) in artificial and natural substrates. Chemosphere 2009, 75:310-318. 10.1016/j.chemosphere.2009.02.003.
92. Tsai P.-C., Ding W.-H. Determination of alkyltrimethylammonium surfactants in hair conditioners and fabric softeners by gas chromatography-mass spectrometry with electron-impact and chemical ionization. J. Chromatogr. A 2004, 1027:103-108. 10.1016/j.chroma.2003.10.047.
93. Van de Voorde A., Lorgeoux C., Gromaire M.C., Chebbo G. Analysis of quaternary ammonium compounds in urban stormwater samples. Environ. Pollut. 2012, 164:150-157. 10.1016/j.envpol.2012.01.037.
94. van Wijk D., Gyimesi-van den Bos M., Garttener-Arends I., Geurts M., Kamstra J., Thomas P. Bioavailability and detoxification of cationics: I. Algal toxicity of alkyltrimethyl ammonium salts in the presence of suspended sediment and humic acid. Chemosphere 2009, 75:303-309. 10.1016/j.chemosphere.2008.12.047.
95. Vidal J.L.M., Vega A.B., López F.J.S., Frenich A.G. Application of internal quality control to the analysis of quaternary ammonium compounds in surface and groundwater from Andalusia (Spain) by liquid chromatography with mass spectrometry. J. Chromatogr. A 2004, 1050:179-184. 10.1016/j.chroma.2004.08.023.
96. Watson M.K., Tezel U., Pavlostathis S.G. Biotransformation of alkanoylcholines under methanogenic conditions. Water Res. 2012, 46:2947-2956. 10.1016/j.watres.2012.03.021.
97. Wee V.T., Kennedy J.M. Determination of trace levels of quaternary ammonium compounds in river water by liquid chromatography with conductometric detection. Anal. Chem. 1982, 54:1631-1633. 10.1021/ac00246a037.
98. Wong S.P., Lim W.H., Cheng S.F., Chuah C.H. Biological properties of sodium alkyl methyl ester sulfonate/alkyltrimethylammonium bromide surfactant mixtures. Colloids Surf. B: Biointerfaces 2012, 89:48-52. 10.1016/j.colsurfb.2011.08.021.
99. Yamamoto K., Oka M., Murakami H. Spectrophotometric determination of trace ionic and non-ionic surfactants based on a collection on a membrane filter as the ion associate of the surfactant with Erythrosine B. Anal. Chim. Acta 2002, 455:83-92. 10.1016/S0003-2670(01)01560-4.
100. Yang J. Fate and Effect of Alkyl Benzyl Dimethyl Ammonium Chloride in Mixed Aerobic and Nitrifying Cultures 2007, (MS Thesis), Georgia Institute of Technology, Atlanta, GA.
101. Ying G.G. Fate, behavior and effects of surfactants and their degradation products in the environment. Environ. Int. 2006, 32:417-431. 10.1016/j.envint.2005.07.004.
102. Yu F., Ge F., Zhou W., Tao N., Liang Z., Zhu L. Subcellular distribution of fluoranthene in Chlorella vulgaris with the presence of cetyltrimethylammonium chloride. Chemosphere 2013, 90:929-935. 10.1016/j.chemosphere.2012.06.032.
103. Zhang C., Tezel U., Li K., Liu D., Ren R., Du J., et al. Evaluation and modeling of benzalkonium chloride inhibition and biodegradation in activated sludge. Water Res. 2011, 45:1238-1246. 10.1016/j.watres.2010.09.037.
104. Zhu M., Ge F., Zhu R., Wang X., Zheng X. A DFT-based QSAR study of the toxicity of quaternary ammonium compounds on Chlorella vulgaris. Chemosphere 2010, 80:46-52. 10.1016/j. chemosphere .2010.03.044.