Abstract
New ester functionalized branched anionic surfactant—sodium citronellyl sulfoacetate (SCSA) is developed from naturally occurring acyclic monoterpene citronellol. This new surfactant is investigated for its self-aggregation, detergent, and biodegradation properties. Surface properties of the SCSA are determined by surface tension and conductivity method. Hydrodynamic radius of the micelles formed by the new surfactant is determined by dynamic light scattering technique. Detergency and foaming properties of the new surfactant are determined by Tergotometer and Ross-Miles method respectively. Further, the biodegradation property of the SCSA was determined by the BOD method. The experimental evaluation result establishes SCSA to be a good sustainable alternative to petrochemical derived surfactants. The new surfactant demonstrated good surface activity along with excellent detergent and biodegradation properties.
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Höfer R, Bigorra J (2007) Green chemistry—a sustainable solution for industrial specialties applications. Green Chem 9:203–212
Bhadani A, Kafle A, Ogura T, Akamatsu M, Sakai K, Sakai H, Abe M (2019) Phase behavior of ester based anionic surfactants: sodium alkyl sulfoacetates. Ind Eng Chem Res 58:6235–6242
Hargreaves AE, Hargreaves T (2003) Chemical formulation: an overview of surfactant-based preparations used in everyday life; Royal Society of Chemistry: Vol. 32
Mudge SM, Deleo PC (2014) Estimating fatty alcohol contributions to the environment from laundry and personal care products using a market forensics approach. Environ Sci Process Impacts 16:74–80
Gallezot P (2012) Conversion of biomass to selected chemical products. Chem Soc Rev 41:1538–1558
Bhadani A, Iwabata K, Sakai K, Koura S, Sakai H, Abe M (2015) Sustainable oleic and stearic acid based biodegradable surfactants. RSC Adv 7:10433–10442
Coleman D, Gathergood N (2010) Biodegradation studies of ionic liquids. Chem Soc Rev 39:600–637
Lebeuf R, Liu C-Y, Pierlot C, Nardello-Rataj V (2018) Synthesis and surfactant properties of nonionic biosourced alkylglucuronamides. ACS Sustain Chem Eng 6:2758–2766
De S, Malik S, Ghosh A, Saha R, Saha B (2015) A review on natural surfactants. RSC Adv 5:65757–65767
Bhadani A, Rane J, Veresmortean C, Banerjee S, John G (2015) Bio-inspired surfactants capable of generating plant volatiles. Soft Matter 11:3076–3082
Bhadani A, Kafle A, Ogura T, Akamatsu M, Sakai K, Sakai H, Abe M (2020) Current perspective of sustainable surfactants based on renewable building blocks. Curr Opin Colloid Interface Sci 45:124–135
Bhadani A, Endo T, Sakai K, Sakai H, Abe M (2014) Synthesis and dilute aqueous solution properties of ester functionalized cationic gemini surfactants having different ethylene oxide units as spacer. Colloid Polym Sci 292:1685–1692
Bhadani A, Okano T, Ogura T, Misono T, Sakai K, Abe M, Sakai H (2016) Structural features and surfactant properties of core–shell type micellar aggregates formed by gemini piperidinium surfactants. Colloids Surf A Physicochem Eng Asp 494:147–155
Bhadani A, Kafle A, Koura S, Sakai K, Sakai H, Abe M (2017) Physicochemical evaluation of micellar solution and lyotropic phases formed by self-assembled aggregates of morpholinium geminis. ACS Omega 2:5324–5334
Kafle A, Akamatsu M, Bhadani A, Sakai K, Kaise C, Kaneko T, Sakai H (2018) Effects of β-sitosteryl sulfate on the properties of DPPC liposomes. J Oleo Sci 67:1511–1519
Hama I, Sakaki M, Sasamoto H (1997) Effects of ethoxylate structure on surfactant properties of ethoxylated fatty methyl esters. J Am Oil Chem Soc 74:823–827
Tamura T, Iihara T, Nishida S, Ohta S (1999) Cleaning performance and foaming properties of lauroylamidopropylbetaine/nonionics mixed systems. J Surfactant Deterg 2:207–211
Wang R, Li Y, Li Q (2013) Synthesis and properties of dodecyldiethoxylamine oxide. J Surfactant Deterg 16:509–514
Karasawa M, Hasegawa T, Komaki M, Narumi T (2006) Washing method by introducing air into an alternating flow system. J Oleo Sci 55:521–527
Ushida A, Hasegawa T, Takahashi N, Nakajima T, Murao S, Narumi T, Uchiyama H (2012) Effect of mixed nanobubble and microbubble liquids on the washing rate of cloth in an alternating flow. J Surfactant Deterg 15:695–702
Goon P, Bhirud RG, Kumar VV (1999) Detergency and foam studies on linear alkylbenzene sulfonate and secondary alkyl sulfonate. J Surfactant Deterg 2:489–493
Yoshimura T, Ishihara K, Esumi K (2005) Sugar-based gemini surfactants with peptide bonds-synthesis, adsorption, micellization, and biodegradability. Langmuir 21:10409–10415
Ashraf U, Chat OA, Maswal M, Jabeen S, Dar AA (2015) An investigation of Pluronic P123–sodium cholate mixed system: micellization, gelation and encapsulation behavior. RSC Adv 5:83608–83618
Zhang Z, Xu G, Wang F, Du G (2005) Aggregation behaviors and interfacial properties of oxyethylated nonionic surfactants. J Dispers Sci Technol 26:297–302
Bera A, Mandal A, Belhaj H, Kumar T (2017) Enhanced oil recovery by nonionic surfactants considering micellization, surface, and foaming properties. Pet Sci 14:362–371
Gad EAM, El-Sukkary MMA, Azzam EMS (1997) Surface and thermodynamic properties of octyl, dodecyl, and cetyl sulfoacetates. Monatsh Chem - Chem Mon 128:1085–1092
Venkatesan P, Cheng Y, Kahne D (1994) Hydrogen bonding in micelle formation. J Am Chem Soc 116:6955–6956
Carpena P, Aguiar J, Bernaola-Galván P, Ruiz CC (2002) Problems associated with the treatment of conductivity−concentration data in surfactant solutions: simulations and experiments. Langmuir 18:6054–6058
Ray GB, Chakraborty I, Ghosh S, Moulik SP (2006) A critical and comprehensive assessment of interfacial and bulk properties of aqueous binary mixtures of anionic surfactants, sodium dodecylsulfate, and sodium dodecylbenzenesulfonate. Colloid Polym Sci 285:457–469
Tamura T, Kaneko Y, Ohyama M (1995) Dynamic surface tension and foaming properties of aqueous polyoxyethylene n-dodecyl ether solutions. J Colloid Interface Sci 173:493–499
El-Ghaffar MAA, Sherif MH, El-Habab AT (2016) Synthesis, characterization, and evaluation of ethoxylated lauryl-myrisityl alcohol nonionic surfactants as wetting agents, anti-foamers, and minimum film forming temperature reducers in emulsion polymer lattices. J Surfactant Deterg 20:117–128
Azira H, Tazerouti A, Canselier JP (2008) Study of foaming properties and effect of the isomeric distribution of some anionic surfactants. J Surfactant Deterg 11:279–286
Varadaraj R, Bock J, Valint P, Zushma S, Brons N (1990) Relationship between fundamental interfacial properties and foaming in linear and branched sulfate, ethoxysulfate, and ethoxylate surfactants. J Colloid Interface Sci 140:31–34
Beneventi D, Carre B, Gandini A (2001) Role of surfactant structure on surface and foaming properties. Colloids Surf A Physicochem Eng Asp 189:65–73
Tadros TF (2005) Applied surfactants: principles and applications, Weinheim, Wiley-VCH Verlag GmbH & Co. KGaA
Tehrani-Bagha AR, Holmberg K (2010) Cationic ester-containing gemini surfactants: physical−chemical properties. Langmuir 26:9276–9282
Guimarães AC, Meireles LM, Lemos MF, Guimarães MCC, Endringer DC, Fronza M, Scherer R (2019) Antibacterial activity of terpenes and terpenoids present in essential oils. Molecules 24:2471
Gochev V, Wlcek K, Buchbauer G, Stoyanova A, Dobreva A, Schmidt E, Jirovetz L (2008) Comparative evaluation of antimicrobial activity and composition of rose oils from various geographic origins, in particular bulgarian rose oil. Nat Prod Commun 3:1063–1068
Acknowledgments
We are thankful to Nikkol Group, Cosmos Technical Center, Japan, for the scale up production of SCSA surfactant in the batch process in their research center.
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There is no source of financial funding for this research. However, authors are thankful to Tokyo University of Science and Acteiive Research & Development Company, Japan, for research support.
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Bhadani, A., Hokyun, J., Kafle, A. et al. Synthesis and properties of renewable citronellol based biodegradable anionic surfactant. Colloid Polym Sci 298, 1543–1550 (2020). https://doi.org/10.1007/s00396-020-04735-z
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DOI: https://doi.org/10.1007/s00396-020-04735-z