Soil water solutes reduce the critical micelle concentration of quaternary ammonium compounds.
Critical micelle concentration
Dissolved organic matter
Fluorescence
Quaternary alkyl ammonium compound
Journal
Environmental science and pollution research international
ISSN: 1614-7499
Titre abrégé: Environ Sci Pollut Res Int
Pays: Germany
ID NLM: 9441769
Informations de publication
Date de publication:
Dec 2020
Dec 2020
Historique:
received:
17
04
2020
accepted:
17
07
2020
pubmed:
14
8
2020
medline:
27
11
2020
entrez:
14
8
2020
Statut:
ppublish
Résumé
Quaternary alkyl ammonium compounds (QAACs) are produced in large quantities for use as surfactants and disinfectants and also found in soils, sediments, and surface waters, where they are potentially involved in the selection of antibiotic resistance genes. Micelle formation influences fate and effects of QAACs. The critical micelle concentration (CMC) of six homologs of benzylalkylammonium chlorides (BAC) was determined in deionized water, 0.01 M CaCl
Identifiants
pubmed: 32789630
doi: 10.1007/s11356-020-10188-2
pii: 10.1007/s11356-020-10188-2
pmc: PMC7686171
doi:
Substances chimiques
Micelles
0
Quaternary Ammonium Compounds
0
Soil
0
Solutions
0
Surface-Active Agents
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
45311-45323Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : MU3988/1-1
Organisme : Deutsche Forschungsgemeinschaft
ID : MU3988/2-1
Références
Aguiar J, Carpena P, Molina-Bolívar JA, Carnero Ruiz C (2003) On the determination of the critical micelle concentration by the pyrene 1:3 ratio method. J Colloid Interface Sci 258:116–122. https://doi.org/10.1016/S0021-9797(02)00082-6
doi: 10.1016/S0021-9797(02)00082-6
Akbaş H, Taner T (2009) Spectroscopic studies of interactions between C.I. Reactive Orange 16 with alkyltrimethylammonium bromide surfactants. Spectrochim Acta A Mol Biomol Spectrosc 73:150–153. https://doi.org/10.1016/j.saa.2009.02.018
doi: 10.1016/j.saa.2009.02.018
Asakawa T, Kitano H, Ohta A, Miyagishi S (2001) Convenient estimation for counterion dissociation of cationic micelles using chloride-sensitive fluorescence probe. J Colloid Interface Sci 242:284–287. https://doi.org/10.1006/jcis.2001.7875
doi: 10.1006/jcis.2001.7875
Ashraf U, Lone MS, Masrat R et al (2020) Co-solubilization of polycyclic aromatic hydrocarbon mixtures in aqueous micellar systems and its correlation with FRET for enhanced remediation processes. Chemosphere 242:UNSP 125160. https://doi.org/10.1016/j.chemosphere.2019.125160
doi: 10.1016/j.chemosphere.2019.125160
Avranas A, Gernátová M (2007) Effect of deaeration on the adsorption of a mixture of cetyltrimethylammonium bromide and cetyldimethylbenzylammonium chloride at the mercury/electrolyte solution interface. J Colloid Interface Sci 310:509–518. https://doi.org/10.1016/j.jcis.2007.01.053
doi: 10.1016/j.jcis.2007.01.053
Brito RMM, Vaz WLC (1986) Determination of the critical micelle concentration of surfactants using the fluorescent probe N-phenyl-1-naphthylamine. Anal Biochem 152:250–255. https://doi.org/10.1016/0003-2697(86)90406-9
doi: 10.1016/0003-2697(86)90406-9
del Castillo JL, Czapkiewicz J, González Pérez A, Rodríguez JR (2000) Micellization of decyldimethylbenzylammonium chloride at various temperatures studied by densitometry and conductivity. Colloids Surf A Physicochem Eng Asp 166:161–169. https://doi.org/10.1016/S0927-7757(99)00515-4
doi: 10.1016/S0927-7757(99)00515-4
Cepeda M, Daviña R, García-Río L, Parajó M, Rodríguez-Dafonte P, Pessêgo M (2013) Competition between surfactant micellization and complexation by cyclodextrin. Org Biomol Chem 11:1093–1102. https://doi.org/10.1039/C2OB26318A
doi: 10.1039/C2OB26318A
Conte P, Agretto A, Spaccini R, Piccolo A (2005) Soil remediation: humic acids as natural surfactants in the washings of highly contaminated soils. Environ Pollut 135:515–522. https://doi.org/10.1016/j.envpol.2004.10.006
doi: 10.1016/j.envpol.2004.10.006
Cui X, Jiang Y, Yang C, Lu X, Chen H, Mao S, Liu M, Yuan H, Luo P, du Y (2010) Mechanism of the mixed surfactant micelle formation. J Phys Chem B 114:7808–7816. https://doi.org/10.1021/jp101032z
doi: 10.1021/jp101032z
Deshpande S, Shiau BJ, Wade D et al (1999) Surfactant selection for enhancing ex situ soil washing. Water Res 33:351–360. https://doi.org/10.1016/S0043-1354(98)00234-6
doi: 10.1016/S0043-1354(98)00234-6
Dominguez A, Fernandez A, Gonzalez N et al (1997) Determination of critical micelle concentration of some surfactants by three techniques. J Chem Educ 74:1227. https://doi.org/10.1021/ed074p1227
doi: 10.1021/ed074p1227
Dultz S, Steinke H, Mikutta R et al (2018) Impact of organic matter types on surface charge and aggregation of goethite. Colloids Surf A Physicochem Eng Asp 554:156–168. https://doi.org/10.1016/j.colsurfa.2018.06.040
doi: 10.1016/j.colsurfa.2018.06.040
Ghasemi A, Bagheri A (2020) Effects of alkyl chain length on synergetic interaction and micelle formation between a homologous series of n-alkyltrimethylammonium bromides and amphiphilic drug propranolol hydrochloride. J Mol Liq 298:111948. https://doi.org/10.1016/j.molliq.2019.111948
doi: 10.1016/j.molliq.2019.111948
Gitipour S, Mohebban A, Ghasemi S, Abdollahinejad M, Abdollahinejad B (2020) Evaluation of effective parameters in washing of PAH-contaminated soils using response surface methodology approach. Int J Environ Sci Technol 17:683–694. https://doi.org/10.1007/s13762-019-02368-6
doi: 10.1007/s13762-019-02368-6
González-Pérez A, Czapkiewicz J, Del Castillo JL, Rodríguez JR (2001) Micellar properties of long-chain alkyldimethylbenzylammonium chlorides in aqueous solutions. Colloids Surf A Physicochem Eng Asp 193:129–137. https://doi.org/10.1016/S0927-7757(01)00754-3
doi: 10.1016/S0927-7757(01)00754-3
Griffin BA, Jurinak JJ (1973) Estimation of activity coefficients from the electrical conductivity of natural aquatic systems and soil extracts. Soil Sci 116:26–30
doi: 10.1097/00010694-197307000-00005
Ishiguro M, Koopal LK (2016) Surfactant adsorption to soil components and soils. Adv Colloid Interf Sci 231:59–102. https://doi.org/10.1016/j.cis.2016.01.006
doi: 10.1016/j.cis.2016.01.006
Ishiguro M, Tan W, Koopal LK (2007) Binding of cationic surfactants to humic substances. Colloid Surf A-Physicochem Eng Asp 306:29–39. https://doi.org/10.1016/j.colsurfa.2006.12.024
doi: 10.1016/j.colsurfa.2006.12.024
Ismail ZZ, Tezel U, Pavlostathis SG (2010) Sorption of quaternary ammonium compounds to municipal sludge. Water Res 44:2303–2313. https://doi.org/10.1016/j.watres.2009.12.029
doi: 10.1016/j.watres.2009.12.029
Itoh Y, Horiuchi S, Yamamoto K (2005) Photodegradative surfactants: photolyses of p-alkylbenzyltrimethylammonium and alkylbenzyldimethylammonium halides in aqueous solution. Photochem Photobiol Sci 4:835–839. https://doi.org/10.1039/B507811C
doi: 10.1039/B507811C
Jechalke S, Schreiter S, Wolters B et al (2014) Widespread dissemination of class 1 integron components in soils and related ecosystems as revealed by cultivation-independent analysis. Front Microbiol 4. https://doi.org/10.3389/fmicb.2013.00420
Jennings MC, Minbiole KPC, Wuest WM (2015) Quaternary ammonium compounds: an antimicrobial mainstay and platform for innovation to address bacterial resistance. ACS Infect Dis 1:288–303. https://doi.org/10.1021/acsinfecdis.5b00047
doi: 10.1021/acsinfecdis.5b00047
Johnson WP, Amy GL (1995) Facilitated transport and enhanced desorption of polycyclic aromatic hydrocarbons by natural organic matter in aquifer sediments. Environ Sci Technol 29:807–817. https://doi.org/10.1021/es00003a032
doi: 10.1021/es00003a032
Kaiser K, Kalbitz K (2012) Cycling downwards–dissolved organic matter in soils. Soil Biol Biochem 52:29–32. https://doi.org/10.1016/j.soilbio.2012.04.002
doi: 10.1016/j.soilbio.2012.04.002
Kalyanasundaram K, Thomas JK (1977) Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J Am Chem Soc 99:2039–2044. https://doi.org/10.1021/ja00449a004
doi: 10.1021/ja00449a004
Kralchevsky PA, Danov KD, Denkov ND (2002) Chapter 5. Chemical physics of colloid systems and interfaces. In: handbook of surface and colloid chemistry. CRC Press, New York, p 118
Kronberg B, Holmberg K, Lindman B (2014) Types of Surfactants, their Synthesis, and Applications. In: Surface Chemistry of Surfactants and Polymers.John Wiley & Sons, Ltd, pp 1–47. https://doi.org/10.1002/9781118695968.ch1
Lara-Martín PA, Li X, Bopp RF, Brownawell BJ (2010) Occurrence of alkyltrimethylammonium compounds in urban estuarine sediments: behentrimonium as a new emerging contaminant. Environ Sci Technol 44:7569–7575. https://doi.org/10.1021/es101169a
doi: 10.1021/es101169a
Lemić J, Tomašević-Čanović M, Djuričić M, Stanić T (2005) Surface modification of sepiolite with quaternary amines. Journal of Colloid and Interface Science 292:11–19. https://doi.org/10.1016/j.jcis.2005.05.080
Li X, Brownawell BJ (2010) Quaternary ammonium compounds in urban estuarine sediment environments-a class of contaminants in need of increased attention? Environ Sci Technol 44:7561–7568. https://doi.org/10.1021/es1011669
doi: 10.1021/es1011669
Mao X, Jiang R, Xiao W, Yu J (2015) Use of surfactants for the remediation of contaminated soils: a review. J Hazard Mater 285:419–435. https://doi.org/10.1016/j.jhazmat.2014.12.009
doi: 10.1016/j.jhazmat.2014.12.009
Marcotte L, Barbeau J, Lafleur M (2005) Permeability and thermodynamics study of quaternary ammonium surfactants—phosphocholine vesicle system. J Colloid Interface Sci 292:219–227. https://doi.org/10.1016/j.jcis.2005.05.060
doi: 10.1016/j.jcis.2005.05.060
Martínez-Carballo E, González-Barreiro C, Sitka A, Kreuzinger N, Scharf S, Gans O (2007) Determination of selected quaternary ammonium compounds by liquid chromatography with mass spectrometry. Part II. Application to sediment and sludge samples in Austria. Environ Pollut 146:543–547. https://doi.org/10.1016/j.envpol.2006.07.016
doi: 10.1016/j.envpol.2006.07.016
Moroi Y (1992) Mixed micelle formation. In: Moroi Y (ed) Micelles: theoretical and applied aspects. Springer US, Boston, MA, pp 183–194
doi: 10.1007/978-1-4899-0700-4_10
Mulder I, Siemens J, Sentek V, Amelung W, Smalla K, Jechalke S (2018) Quaternary ammonium compounds in soil: implications for antibiotic resistance development. Rev Environ Sci Biotechnol 17:159–185. https://doi.org/10.1007/s11157-017-9457-7
doi: 10.1007/s11157-017-9457-7
Nazrul Isalam M, Sharker KK, Sarker KC (2015) Salt-induced modulation of the Krafft temperature and critical micelle concentration of benzyldimethylhexadecylammonium chloride. J Surfactant Deterg 18:651–659. https://doi.org/10.1007/s11743-015-1696-4
doi: 10.1007/s11743-015-1696-4
Noüy D, Lecomte P (1925) An interfacial tensiometer for universal use. J Gen Physiol 7:625–631. https://doi.org/10.1085/jgp.7.5.625
doi: 10.1085/jgp.7.5.625
Ogunmokun FA, Liu Z, Wallach R (2020) The influence of surfactant-application method on the effectiveness of water-repellent soil remediation. Geoderma 362:114081. https://doi.org/10.1016/j.geoderma.2019.114081
doi: 10.1016/j.geoderma.2019.114081
Organisation for Economic Co-operation and Development (2009) OECD 2007 list of high production volume chemicals, OECD Environment, Health and Safety Publications Series on Testing and Assessment, vol 112, p 104
Östman M, Lindberg RH, Fick J, Björn E, Tysklind M (2017) Screening of biocides, metals and antibiotics in Swedish sewage sludge and wastewater. Water Res 115:318–328. https://doi.org/10.1016/j.watres.2017.03.011
doi: 10.1016/j.watres.2017.03.011
Ponnamperuma FN, Tianco EM, Loy TA (1966) Ionic strengths of the solutions of flooded soils and other natural aqueous solutions from specific conductance. Soil Sci 102:408
doi: 10.1097/00010694-196612000-00009
Ranjan R, Qian Y, Krishnapillai M, (2006) Effects of electrokinetics and cationic surfactant cetyltrimethylammonium bromide [CTAB] on the hydrocarbon removal and retention from contaminated soils.Environ Technol 27 (7) 767-776
Rauwel G, Leclercq L, Criquelion J, Aubry JM, Nardello-Rataj V (2012) Aqueous mixtures of di-n-decyldimethylammonium chloride/polyoxyethylene alkyl ether: dramatic influence of tail/tail and head/head interactions on co-micellization and biocidal activity. J Colloid Interface Sci 374:176–186. https://doi.org/10.1016/j.jcis.2012.02.006
doi: 10.1016/j.jcis.2012.02.006
Rosen, MJ (2004) Micelle Formation by Surfactants. In: Surfactants and Interfacial Phenomena. John Wiley & Sons, Ltd, pp 105–177. https://doi.org/10.1002/0471670561.ch3
Seifert A-G, Roth V-N, Dittmar T, Gleixner G, Breuer L, Houska T, Marxsen J (2016) Comparing molecular composition of dissolved organic matter in soil and stream water: influence of land use and chemical characteristics. Sci Total Environ 571:142–152. https://doi.org/10.1016/j.scitotenv.2016.07.033
doi: 10.1016/j.scitotenv.2016.07.033
Tadros T (2005) Physical Chemistry of Surfactant Solutions. In: Applied Surfactants. John Wiley & Sons, Ltd, pp 19–51. https://doi.org/10.1002/3527604812.ch2
Taylor DJF, Thomas RK, Li PX, Penfold J (2003) Adsorption of oppositely charged polyelectrolyte/surfactant mixtures. Neutron reflection from alkyl trimethylammonium bromides and sodium poly(styrenesulfonate) at the air/water interface: the effect of surfactant chain length. Langmuir 19:3712–3719. https://doi.org/10.1021/la020709e
doi: 10.1021/la020709e
Thieme L, Graeber D, Kaupenjohann M, Siemens J (2016) Fast-freezing with liquid nitrogen preserves bulk dissolved organic matter concentrations, but not its composition. Biogeosciences 13:4697–4705. https://doi.org/10.5194/bg-13-4697-2016
doi: 10.5194/bg-13-4697-2016
Thomas GW (1996) Methods of soil analysis. In: Soil pH and soil acidity. Soil Science Society of America, Madison, Wisconsin, USA, pp 475–490
Tokiwa F, Moriyama N (1969) Mixed micelle formation of anionic and nonionic surfactants. J Colloid Interface Sci 30:338–344. https://doi.org/10.1016/0021-9797(69)90400-7
doi: 10.1016/0021-9797(69)90400-7
Velegol SB, Fleming BD, Biggs S et al (2000) Counterion effects on hexadecyltrimethylammonium surfactant adsorption and self-assembly on silica. Langmuir 16:2548–2556. https://doi.org/10.1021/la9910935
doi: 10.1021/la9910935
Wu W, Sun H, Wang L, Li K, Wang L (2010) Comparative study on the micelle properties of synthetic and dissolved organic matters. J Hazard Mater 174:635–640. https://doi.org/10.1016/j.jhazmat.2009.09.098
doi: 10.1016/j.jhazmat.2009.09.098
WRB (2015) World reference base for soil resources 2014: international soil classification system for naming soils and creating legends for soilmaps. Update 2015. Food and Agricultural Organization of the United Nations (2015) Rome
Zdziennicka A, Szymczyk K, Krawczyk J, Jańczuk B (2012) Critical micelle concentration of some surfactants and thermodynamic parameters of their micellization. Fluid Phase Equilib 322–323:126–134. https://doi.org/10.1016/j.fluid.2012.03.018
doi: 10.1016/j.fluid.2012.03.018
Zhang C, Cui F, Zeng G, Jiang M, Yang ZZ, Yu ZG, Zhu MY, Shen LQ (2015) Quaternary ammonium compounds (QACs): a review on occurrence, fate and toxicity in the environment. Sci Total Environ 518:352–362. https://doi.org/10.1016/j.scitotenv.2015.03.007
doi: 10.1016/j.scitotenv.2015.03.007