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Characterization and Surface Active Properties of Aliphatic Glycerol Acetal Disodium Sulfosuccinates

  • Lan Wu , Xu Li and Jinxiang Dong
Published/Copyright: March 3, 2017
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Abstract

A new group of cleavable di-anionic surfactants aliphatic glycerol acetal di-sodium sulfosuccinates has been successfully synthesized starting from esterification reaction of aliphatic glycerol acetals with maleic anhydride, followed by sulfonation with sodium sulfite. The prepared surfactants were characterized by Fourier transform infrared spectroscopy (FT-IR), mass spectroscopy (MS) and elemental analysis. The surface active properties of the new surfactants, such as surface tension, critical micelle concentration (CMC), foaming property, and emulsifying power were determined.

Kurzfassung

Es wurde eine neue Gruppe von spaltbaren, di-anionischen Tensiden (aliphatische Glycerolacetal-di-Natriumsulfosuccinate) durch Veresterung von aliphatischen Glycerolacetalen mit Maleinsäureanhydrid und nachfolgender Sulfonierung mit Natriumsulfit, erfolgreich synthetisiert. Die hergestellten Tenside wurden mit der Fourier-Transformations IR-Spektroskopie (FT-IR), der Massenspektroskopie (MS) und der Elementaranalyse charakterisiert. Die oberflächenaktiven Eigenschaften der neuen Tenside wie die Oberflächenspannung, die kritische Mizellenbildungskonzentration (CMC), das Schaum- und Emulgiervermögen wurden bestimmt.


* Correspondence address, Dr. Jinxiang Dong, Research Institute of Special Chemicals, College of Chemistry and Chemical Engineering, Taiyuan University of Technology, 79# West Yingze Avenue, Wanbailin Distrct., Taiyuan, Shanxi 030024, China, Tel.: +86-1 37 00 51 24 66, Fax: +86-03 51-6 11-11 78, E-Mail:
** Co-Author: Dr. Xu Li, Research Institute of Special Chemicals, College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan, Shanxi, P. R. China, E-Mail:

Lan Wu, Xu Li, Jinxiang Dong: Research Institute of Special Chemicals, College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan, Shanxi, P. R. China


References

1. Myers D. : An overview of surfactant science and technology, in: Surfactant science and technology, 3rd ed., John Wiley & Sons, Hoboken, New Jersey (2005). 10.1002/047174607XSearch in Google Scholar

2. Foley P. , BeachE. S. and ZimmermanJ. B.: Derivation and synthesis of renewable surfactants, Chem. Soc. Rev.41 (2012) 14991518. 10.1039/c1cs15217cSearch in Google Scholar

3. Hauthal H. G. : Fourth european detergents conference report: Sustainable detergents and cleaners, progress on ingredients, nanoparticles, analysis, environment, Tenside Surf. Det.46 (2009) 5362. 10.3139/113.110008Search in Google Scholar

4. Cintas P. , TagliapietraS., GaudinoE. C., PalmisanoG. and CravottoG.: Glycerol: A solvent and a building block of choice for microwave and ultrasound irradiation procedures, Green Chem.16 (2014) 10561065. 10.1039/c3 gc41955jSearch in Google Scholar

5. Gu Y. and JérômeF.: Glycerol as a sustainable solvent for green chemistry, Green Chem.12 (2010) 11271138. 10.1039/c001628dSearch in Google Scholar

6. Pagliaro M. and RossiM.: in: Clark,J. H. and Kraus,G. A. (Ed.), The future of glycerol, 2nd ed., Royal Society of Chemistry (2010). 10.1002/cssc.201100024Search in Google Scholar

7. Canakci M. and SanliH.: Biodiesel production from various feedstocks and their effects on the fuel properties, J. Ind. Microbiol. Biot.35 (2008) 431441. 10.1007/s10295–008–0337–6Search in Google Scholar

8. Shahid E. M. and JamalY.: Production of biodiesel: A technical review, Renew. Sust. Energ. Rew.15 (2011) 47324745. 10.1016/j.rser.2011.07.079Search in Google Scholar

9. Sharma Y. , SinghB. and UpadhyayS.: Advancements in development and characterization of biodiesel: A review, Fuel.87 (2008) 23552373. 10.1016/j.fuel.2008.01.014Search in Google Scholar

10. Quispe C. A. , CoronadoC. J. and Carvalho JrJ. A.: Glycerol: Production, consumption, prices, characterization and new trends in combustion, Renew. Sust. Energ. Rew.27 (2013) 475493. 10.1016/j.rser.2013.06.017Search in Google Scholar

11. Behr A. , EiltingJ., IrawadiK., LeschinskiJ. and LindnerF.: Improved utilisation of renewable resources: New important derivatives of glycerol, Green Chem.10 (2008) 1330. 10.1039/b710561dSearch in Google Scholar

12. Pagliaro M. , CiriminnaR., KimuraH., RossiM. and Della PinaC.: From glycerol to value-added products, Angew. Chem. Int. Ed.46 (2007) 44344440. 10.1002/anie.200604694Search in Google Scholar

13. Xu J. , YuW., MaH., WangF., LuF., GhavreM. and GathergoodN.: Catalytic conversion of glycerol, in: XieH. and GathergoodN. (Ed.), The Role of Green Chemistry in Biomass Processing and Conversion, 1st ed., John Wiley & Sons, Hoboken, New Jersey (2013). 10.1002/9781118449400.ch12Search in Google Scholar

14. Bhangale A. P. , WadekarS. D., KaleS. B. and PratapA. P.: Sophorolipids synthesized using non-traditional oils with glycerol and studies on their surfactant properties with synthetic surfactant, Tenside Surf. Det.51 (2014) 387396. 10.3139/113.110320Search in Google Scholar

15. Ghosh S. K. , SahaR., GhoshA., MukherjeeK. and SahaB.: Micellar catalysis on 1, 10-phenanthroline promoted chromic acid oxidation of glycerol in aqueous media, Tenside Surf. Det.49 (2012) 370375. 10.3139/113.110204Search in Google Scholar

16. Katryniok B. , KimuraH., SkrzyńskaE., GirardonJ.-S., FongarlandP., CapronM., DucoulombierR., MimuraN., PaulS. and DumeignilF.: Selective catalytic oxidation of glycerol: Perspectives for high value chemicals, Green Chem.13 (2011) 19601979. 10.1039/c1gc15320jSearch in Google Scholar

17. Mulligan C. N. : Environmental applications for biosurfactants, Environ. Pollut.133 (2005) 183198. 10.1016/j.envpol.2004.06.009Search in Google Scholar

18. Cameotra S. S. and MakkarR. S.: Recent applications of biosurfactants as biological and immunological molecules, Current opinion in microbiology. 7 (2004) 262266. 10.1016/j.mib.2004.04.006Search in Google Scholar

19. Alam Z. , DevreeseB. and BeukerJ.: Biosurfactants, in: KosaricN., (Ed.), Surfactant Science Series, Taylor & Francis Group, Boca Raton, (2015).Search in Google Scholar

20. Gaudin P. , JacquotR., MarionP., PouillouxY. and JérômeF.: Acid-catalyzed etherification of glycerol with long-alkyl-chain alcohols, ChemSusChem. 4 (2011) 719722. 10.1002/cssc.201100129Search in Google Scholar

21. Liu F. , VigierK. D. O., Pera-TitusM., PouillouxY., ClacensJ.-M., DecampoF. and JérômeF.: Catalytic etherification of glycerol with short chain alkyl alcohols in the presence of lewis acids, Green Chem.15 (2013) 901909. 10.1039/C3GC36944GSearch in Google Scholar

22. Shi Y. , DayoubW., Favre-RéguillonA., ChenG.-R. and LemaireM.: Straightforward selective synthesis of linear 1-O-alkyl glycerol and di-glycerol monoethers, Tetrahedron Lett.50 (2009) 68916893. 10.1016/j.tetlet.2009.09.134Search in Google Scholar

23. Sutter M. , SilvaE. D., DuguetN., RaoulY., MétayE. and LemaireM.: Glycerol ether synthesis: A bench test for green chemistry concepts and technologies, Chem. Rev.115 (2015) 86098651. 10.1021/cr5004002Search in Google Scholar

24. Isahak W. N. , RamliZ. A., IsmailM. and YarmoM. A.: Highly selective glycerol esterification over silicotungstic acid nanoparticles on ionic liquid catalyst, Ind. Eng. Chem. Res.53 (2014) 1028510293. 10.1021/ie501110mSearch in Google Scholar

25. Bossaert W. D. , De VosD. E., Van RhijnW. M., BullenJ., GrobetP. J. and JacobsP. A.: Mesoporous sulfonic acids as selective heterogeneous catalysts for the synthesis of monoglycerides, J. Catal.182 (1999) 156164. 10.1006/jcat.1998.2353Search in Google Scholar

26. Kharchafi G. , JérômeF., DouliezJ. P. and BarraultJ.: Facile and regioselective mono- or diesterification of glycerol derivatives over recyclable phosphazene organocatalyst, Green Chem.8 (2006) 710716. 10.1039/b603091bSearch in Google Scholar

27. Piasecki A. : Alkoxyalkyl-substituted glycerol acetals: New hydrophobic intermediates for surfactant synthesis, J. Am. Oil Chem. Soc.69 (1992) 639642. 10.1007/BF02635802Search in Google Scholar

28. Sokolowski A. , BurczykB. and OlesJ.: Acetals and ethers. 11. Solubility of alkyl-substituted 1, 3-dioxolanes and 1, 3-dioxanes in water, J. Phys. Chem.88 (1984) 807809. 10.1021/j150648a038Search in Google Scholar

29. Ono D. , MasuyamaA., NakatsujiY., OkaharaM., YamamuraS. and TakedaT.: Preparation, surface-active properties and acid decomposition profiles of a new “soap” bearing a 1, 3-dioxolane ring, J. Am. Oil Chem. Soc.70 (1993) 2936. 10.1007/BF02545363Search in Google Scholar

30. Ono D. , YamamuraS., NakamuraM. and TakedaT.: Synthesis and properties of bis (sodium sulfonated ester) types of cleavable surfactants derived from 1-O-alkylglycerols, J. Surfact. Deterg.1 (1998) 201206. 10.1007/s11743-998-0020-8Search in Google Scholar

31. Piasecki A. , SokolowskiA., BurczykB., GancarzR. and KotlewskaU.: Synthesis, surface properties, and hydrolysis of chemodegradable anionic surfactants: Diastereomerically pure sodium cis-and trans-(2-n-alkyl-1, 3-dioxan-5-yl) sulfates, Langmuir.13 (1997) 14341439. 10.1021/la960207zSearch in Google Scholar

32. Piasecki A. , SokołowskiA., BurczykB. and KotlewskaU.: Synthesis and surface properties of chemodegradable anionic surfactants: Sodium (2-n-alkyl-1, 3-dioxan-5-yl) sulfates, J. Am. Oil Chem. Soc.74 (1997) 3337. 10.1007/s11746-997-0115-zSearch in Google Scholar

33. Burczyk B. , BanaszczykM., SokolowskiA. and PiaseckiA.: Synthesis and surface properties of oxyethylenated 2-alkyl-5-hydroxymethyl-5-ethyl-1,3-dioxanes, J. Am. Oil Chem. Soc.65 (1988) 12041210. 10.1007/BF02660585Search in Google Scholar

34. Lunkenheimer K. , PiaseckiA., BurczykB. and HirteR.: Adsorption properties of diastereomeric 2-n-alkyl-5-methoxy-1, 3-dioxanes at the air/water interface, Langmuir.16 (2000) 69826986. 10.1021/la991160vSearch in Google Scholar

35. Hellberg P.-E. , BergströmK. and HolmbergK.: Cleavable surfactants, J. Surfact. Deterg.3 (2000) 8191. 10.1007/s11743-000-0118-zSearch in Google Scholar

36. Zhang T. , LiX. and DongJ. X.: Methanesulfonic acid as a more efficient catalyst for the synthesis of lauraldehyde glycerol acetal, Tenside Surf. Det.51 (2014) 516520. 10.3139/113.110337Search in Google Scholar

37. Zhang Y. , XuY., QiuS. and YangL.: Synthesis and properties of mono or double long-chain alkanolamine surfactants, J. Surfact. Deterg.16 (2013) 841848. 10.1007/s11743-013-1488-7Search in Google Scholar

38. Chen H. and TangS.-b.: Microwave-assisted synthesis and properties of sodium glycol bis-(isocetyl) sulfosuccinate, J. Surfact. Deterg.15 (2012) 245249. 10.1007/s11743-011-1299-7Search in Google Scholar

39. Zhu H. L. , HuZ. Y., WangJ. L. and CaoD. L.: Synthesis and properties of alkyl dibenzyl ether quaternary ammonium gemini surfactant, Tenside Surf. Det.52 (2015) 163169. 10.3139/113.110362Search in Google Scholar

40. Rosen M. J. : in: Surfactants and interfacial phenomenaed., 3rd ed., John Wiley & Sons, Hoboken, New Jersey, (2004). 10.1002/0471670561Search in Google Scholar

41. Zhu H.-l. , HuZ.-Y., WangJ.-l. and CaoD.-l.: Synthesis and properties of alkyl dibenzyl ether quaternary ammonium gemini surfactant, Tenside Surf. Det.52 (2015) 163169. 10.3139/113.110335Search in Google Scholar

42. Myers D. : Surfactants in solution: Monolayers and micelles, in: Surfactant science and technology, 3rd ed., John Wiley & Sons, Hoboken, New Jersey, (2005). 10.1002/047174607XSearch in Google Scholar

43. Myers D. : Foams and liquid aerosols, in: Surfactant science and technology, 3rd ed., John Wiley & Sons, Hoboken, New Jersey, (2005). 10.1002/047174607XSearch in Google Scholar

44. Myers D. : Emulsions, in: Surfactant science and technology, 3rd ed., John Wiley & Sons, Hoboken, New Jersey, (2005). 10.1002/047174607XSearch in Google Scholar

Received: 2016-04-01
Accepted: 2016-05-30
Published Online: 2017-03-03
Published in Print: 2017-03-15

© 2017, Carl Hanser Publisher, Munich

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