Synthesis and Properties of Lauryl Phosphate Monoester
-
Yaning Shi
Abstract
Lauryl phosphate monoester was synthesized from the starting materials lauryl alcohol and phosphoric acid without catalysts. Subsequently, the crude product was purified by recrystallization and characterized by Fourier transform infrared (FT-IR) and nuclear magnetic resonance (31P-NMR). From the results, it was apparent that the synthesized material was the desired target product. Lauryl monoester potassium phosphate reduced the surface tension of water to 25.08 mN/m at a critical micelle concentration (CMC) of 0.569 mmol/L. It showed a low contact angle and had a low surface tension, indicating a good hydrophilicity. Lauryl monoester potassium phosphate also showed excellent antistatic properties, however its emulsifying ability was not good. The size of the aggregates of lauryl monoester calcium phosphate in aqueous solution was 220 nm and their morphology was spherical.
Kurzfassung
Laurylphosphatmonoester wurde aus den Ausgangsmaterialien Laurylalkohol und Phosphorsäure ohne Katalysatoren synthetisiert. Anschließend wurde das Rohprodukt im Rekristallisationsverfahren gereinigt und mittels Fourier-Transformations-Infrarot (FT-IR) und Kernresonanz (31P-NMR) charakterisiert. Aus den Ergebnissen war ersichtlich, dass das synthetisierte Material das gewünschte Zielprodukt war. Laurylmonoester-Kaliumphosphat senkte die Oberflächenspannung von Wasser auf 25,08 mN/m bei einer kritischen Mizellenbildungskonzentration (CMC) von 0,569 mmol/l. Es zeigte einen geringen Kontaktwinkel und hatte eine niedrige Oberflächenspannung, was auf eine gute Hydrophilie hinweist. Laurylmonoester-Kaliumphosphat zeigte auch ausgezeichnete antistatische Eigenschaften, jedoch war seine Emulgierfähigkeit nicht gut. Die Größe der Aggregate von Laurylmonoesterkaliumphosphat in wässriger Lösung betrug 220 nm bei sphärischer Morphologie.
References
1. Ren, L. F., Wang, X. C. and Qiang, T. T.: Synthesis of amphoteric phosphate ester surfactant by polyphosphoric acid and its application in free-chrome collagen fiber, C. Advanced Materials Research.129 (2010) 271–275. 10.4028/.129-131.271Search in Google Scholar
2. Sahoo, Y., Pizem, H., Fried, T., Golodnitsky, D., Burstein, L., Sukenik, C. N., and Markovich, G.: Alkyl phosphonate/phosphate coating on magnetite nanoparticles: a comparison with fatty acids, Langmuir, 17.25 (2001) 7907–7911. 10.1021/la010703+Search in Google Scholar
3. Abuelyaman, A. S., Hudig, D., Woodard, S. L., and Powers, J. C.: Fluorescent derivatives of diphenyl [1-(N-peptidylamino) alkyl] phosphonate esters: synthesis and use in the inhibition and cellular localization of serine proteases, J. Bioconjugate chemistry, 5.5 (1994) 400–405. PMid:7849068; 10.1021/bc00029a004Search in Google Scholar PubMed
4. McKenna, Charles, E. and Schmidhuser, John: Functional selectivity in phosphonate ester dealkylation with bromotrimethylsilane, J. Journal of the Chemical Society, Chemical Communications, 17 (1979) 739–739. 10.1039/C39790000739Search in Google Scholar
5. Ward, P. A. and Elmer, L.: Mechanisms of the inhibition of chemotaxis by phosphonate esters, J. Journal of Experimental Medicine, 125.6 (1967) 1001–1020. 10.1084/jem.125.6.1001Search in Google Scholar PubMed PubMed Central
6. Bruice, T. C., Tsubouchi, A., Dempcy, R. O. and Olson, L. P.: One-and Two-Metal Ion Catalysis of the Hydrolysis of Adenosine 3‘-Alkyl Phosphate Esters. Models for One-and Two-Metal Ion Catalysis of RNA Hydrolysis, Journal of the American Chemical Society, 118.41 (1996) 9867–9875. 10.1021/ja9607300Search in Google Scholar
7. Cesteros, L. C.: A simple and green procedure to prepare poly (ethylene glycol) networks: Synthesis and properties, J. Green Chemistry, 13.1 (2011) 197–206. 10.1039/C0GC00514BSearch in Google Scholar
8. Sakai, T. and Tajima, J.: Complex of phosphate monoester with their salts, their preparation and surfactant or detergent composition containing them, JP 28133 (2006).Search in Google Scholar
9. Fukegawa, D., Hayakawa, S., Yoshida, Y., Suzuki, K., Osaka, A. and Van Meerbeek, B.: Chemical interaction of phosphoric acid ester with hydroxyapatite, J. Journal of Dental Research, 85.10 (2006) 941–944. PMid:16998137; 10.1177/154405910608501014Search in Google Scholar PubMed
10. Nelson, A. K. and Toy, A. D. F.: The preparation of long-chain monoalkyl phosphates from pyrophosphoric acid and alcohols, J. Inorganic Chemistry, 2.4 (1963) 775–777. 10.1021/ic50008a026Search in Google Scholar
11. Baumn, Robert, A.: The preparation of mixed dialkyl phosphates, J. Synthesis, 12 (1974) 870–872. 10.1055/s-1974-23458Search in Google Scholar
12. Sakakura, A., Mikimoto, K. and Kazuaki, I.: The Oxorhenium (VII)-Catalyzed Direct Condensation of Phosphoric Acid with an Alcohol, J. Angewandte Chemie International Edition, 46.9 (2007) 1423–1426. PMid:17226888; 10.1002/anie.200604333Search in Google Scholar
13. Friedli, F. E., Koehle, H. J., Fender, M., Watts, M., Keys, R., Frank, P., Toney, C.J. and Doerr, M.: Upgrading triethanolamine esterquat performance to new levels, J. Journal of surfactants and detergents, 5 (2002) 211–216. 10.1007/s11743-002-0220-2Search in Google Scholar
14. Hameed, B. H., Mahmoud, D. K. and Ahmad, A. L.: Equilibrium modeling and kinetic studies on the adsorption of basic dye by a low-cost adsorbent: Coconut (Cocos nucifera) bunch waste, J. Journal of Hazardous Materials, 158 (2008) 65–72. PMid:18308467; 10.1016/j.jhazmat.2008.01.034Search in Google Scholar
15. Kurosaki, T. and Manba, A.: Method for producing a phosphoric Monoester, P US 4350645 (1982).Search in Google Scholar
16. Sahoo, Y., Pizem, H., Fried, T., Golodnitsky, D., Burstein, L., Sukenik, C. N. and Markovich, G.: Alkyl phosphonate/phosphate coating on magnetite nanoparticles: a comparison with fatty acids, Langmuir, 17.25 (2001) 7907–7911. 10.1021/la010703+Search in Google Scholar
17. Rosen, M. J. and Joy, T.: Micelle formation by surfactants, J. Surfactants and Interfacial Phenomena, 4 (1989) 123–201. 10.1002/9781118228920.ch3Search in Google Scholar
18. Tsubone, K. and Rosen, M. J.: Structural effect on surface activities of anionic surfactants having N-acyl-N-methylamide and carboxylate groups, J. Journal of colloid and interface science, 244 (2001) 394–398. 10.1006/jcis.2001.7995Search in Google Scholar
19. Kuiper, J. M., Hulst, R. and Engberts, J. B. F. N.: A selective and mild synthetic route to dialkyl phosphates, J. Synthesis, 05 (2003) 0695–0698. 10.1002/chin.200328196Search in Google Scholar
20. Sakakura, A., Mikimoto, K. and Kazuaki, I.: Selective synthesis of phosphate monoesters by dehydrative condensation of phosphoric acid and alcohols promoted by nucleophilic bases, J. Organic letters, 7.10 (2005) 1999–2002. PMid:15876039; 10.1021/ol0504796Search in Google Scholar
21. Ward, A. F. H. and Tordai, L.: Time dependence of boundary tensions of solutions 1. The role of diffusion in time effects, J. Chem Phys, 14 (1946) 453–461. 10.1063/1.1724167Search in Google Scholar
22. Fainerman, V. B., Makievski, A. V. and Miller, R.: The analysis of dynamic surface tension of sodium alkyl sulphate solutions, based on asymptotic equations of adsorption kinetic theory, J. Colloid Surf. A, 87 (1994) 61–75. 10.1016/0927-7757(94)02747-1Search in Google Scholar
23. Eastoe, J. and Dalton, J. S.: Dynamic surface tension and adsorption mechanisms of surfactants at the air/water interface, J. Colloid Interface Sci, 85 (2000) 103–144. 10.1016/S0001-8686(99)00017-2Search in Google Scholar
24. Yajie, Jiang., Tao, Geng. and Qiuxiao, Li.: Equilibrium and dynamic surface tension properties of salt-free catanionic surfactants with different hydrocarbon chain lengths, J. Mol Liq, 204 (2015) 126–131. 10.1016/j.molliq.2015.01.026Search in Google Scholar
25. Yuyang, Gao. and Xiuquan, Yang.: Equilibrium and dynamic surface properties of sulfosuccinate surfactants, J. Journal of Surfactants and Detergents, 7/6 (2014) 1117–1123. 10.1007/s11743-014-1612-3Search in Google Scholar
26. Tracy, D. J. and Reierson, R. L.: Commercial synthesis of monoalkyl phosphates, J. Journal of surfactants and detergents, 5.2 (2002) 169–172. 10.1007/s11743-009-1153-3Search in Google Scholar
27. Lifei, Zhi., Qiuxiao, Li., Yunling, Li. and Yongbo, Song.: Adsorption and aggregation properties of novel star-shaped gluconamide-type cationic surfactants in aqueous solution, J. Colloid and Polymer Science, 292.5 (2014) 1041–1050. 10.1007/s00396-013-3147-ySearch in Google Scholar
28. Shah, V., Bharatiya, B., Shah, D. O. and Mukherjee, T.: Correlation of dynamic surface tension with sedimentation of PTFE particles and water penetration in powders, Langmuir, 31 (2015) 13725–13733. PMid:26625137; 10.1021/acs.langmuir.5b03725Search in Google Scholar PubMed
29. Ritacco, H., Langevin, D., Diamant, H. and Andelman, D.: Dynamic surface tension of aqueous solutions of ionic surfactants: role of electrostatics, Langmuir, 3 (2011) 1009–1014. PMid:21204545; 10.1021/la103039vSearch in Google Scholar PubMed
© 2019, Carl Hanser Publisher, Munich
Articles in the same Issue
- Contents/Inhalt
- Contents
- Review Article
- Characteristic and Application of Anionic Dimeric Surfactants: A Review
- Body Care
- Reduction of Irritation Potential Caused by Anionic Surfactants in the Use of Various Forms of Collagen Derived from Marine Sources in Cosmetics for Children
- Environmental Chemistry
- Optimization of Biosorption Conditions for Surfactant Induced Decolorization by Anaerobic Sludge Granules
- Evaluation of Polyether Copolymer as Green Scale and Corrosion Inhibitor in Seawater
- Physical Chemistry
- Schiff' Bases as Corrosion Inhibitor for Aluminum Alloy in Hydrochloric Acid Medium
- Study on the Synergism of Binary Surfactant Mixtures containing N-lauroyl-N-methyl Taurine Sodium
- Effect of Spacer on Surface Activity and Foam Properties of Betaine Gemini Surfactants
- Study on the Complex System of Sodium Lauryl Diphenyl Ether Disulfonate and Dodecyl Dimethyl Hydroxyethyl Ammonium Chloride
- Synthesis
- Synthesis and Properties of 9,10-Dihydroxystearic Acid Ethoxylate
- Synthesis and Properties of Lauryl Phosphate Monoester
- Novel Surfactants
- Dehydroabietyl Glycidyl Ether Grafted Hydroxyethyl Chitosan: Synthesis, Characterization and Physicochemical Properties
Articles in the same Issue
- Contents/Inhalt
- Contents
- Review Article
- Characteristic and Application of Anionic Dimeric Surfactants: A Review
- Body Care
- Reduction of Irritation Potential Caused by Anionic Surfactants in the Use of Various Forms of Collagen Derived from Marine Sources in Cosmetics for Children
- Environmental Chemistry
- Optimization of Biosorption Conditions for Surfactant Induced Decolorization by Anaerobic Sludge Granules
- Evaluation of Polyether Copolymer as Green Scale and Corrosion Inhibitor in Seawater
- Physical Chemistry
- Schiff' Bases as Corrosion Inhibitor for Aluminum Alloy in Hydrochloric Acid Medium
- Study on the Synergism of Binary Surfactant Mixtures containing N-lauroyl-N-methyl Taurine Sodium
- Effect of Spacer on Surface Activity and Foam Properties of Betaine Gemini Surfactants
- Study on the Complex System of Sodium Lauryl Diphenyl Ether Disulfonate and Dodecyl Dimethyl Hydroxyethyl Ammonium Chloride
- Synthesis
- Synthesis and Properties of 9,10-Dihydroxystearic Acid Ethoxylate
- Synthesis and Properties of Lauryl Phosphate Monoester
- Novel Surfactants
- Dehydroabietyl Glycidyl Ether Grafted Hydroxyethyl Chitosan: Synthesis, Characterization and Physicochemical Properties
