GSC  Vol.1 No.3 , August 2011
(2-Hydroxyethyl)ammonium Lactates—Highly Biodegradable and Essentially Non-Toxic Ionic Liquids
ABSTRACT
(2-Hydroxyethyl)ammonium lactates have been prepared by reactions of the corresponding (2-hydroxyethyl) amines with lactic acid and characterized by their 1H NMR, IR, and mass spectra. They have been quantita- tively analyzed by HPLC, and their water contents have been determined by the Karl-Fischer method. The title salts are low-melting solids or viscous liquids, and they belong to the class of polar, hydrophilic ionic liquids. The toxicity and chemical and biological degradation of the synthesized ionic liquids have been evaluated by methods described in European Standards. The measurements showed these ionic liquids to be highly biodegradable and only slightly toxic substances. Condensation reactions of benzaldehyde with ethyl cyanoacetate and with acetophenone have been performed in these materials as solvents. The possibility of simultaneously applying these ionic liquids as both solvents and catalysts for the mentioned reactions has been demonstrated, as well as repeated use of the same ionic liquid for a number of condensation reactions without any purification.

Cite this paper
nullS. Pavlovica, A. Zicmanis, E. Gzibovska, M. Klavins and P. Mekss, "(2-Hydroxyethyl)ammonium Lactates—Highly Biodegradable and Essentially Non-Toxic Ionic Liquids," Green and Sustainable Chemistry, Vol. 1 No. 3, 2011, pp. 103-110. doi: 10.4236/gsc.2011.13017.
References
[1]   P. Wasserscheid and T. Welton, “Ionic Liquids in Syn-thesis,” 2nd Edition, Vol. 1, Wiley-VCH, Weinheim, 2008.

[2]   N. Gathergood, M. T. Garcia and P. J. Scammells, “Bio-degradable Ionic Liquids: Part I. Concept, Preliminary Targets and Evaluation,” Green Chemistry, Vol. 6, No. 3, 2004, pp. 166-175. doi:10.1039/b315270g

[3]   M. T. Garcia, N. Gathergood and P. J. Scammells, “Bio-degradable Ionic Liquids. Part II. Effect of the Anion and Toxicology,” Green Chemistry, Vol. 7, No. 1, 2005, pp. 9-14. doi:10.1039/b411922c

[4]   N. Gathergood, P. J. Scammells and M. T. Garcia, “Bio-degradable Ionic Liquids. Part III. The First Biodegradable Ionic Liquid,” Green Chemistry, Vol. 8, No. 2, 2006, pp. 156-160. doi:10.1039/b516206h

[5]   D. Coleman and N. Gathergood, “Biodegradation Studies of Ionic Liquids,” Chemical Society Reviews, Vol. 39, No. 2, 2010, pp. 600-637. doi:10.1039/b817717c

[6]   M. Stasiewicz, E. Mulkiewicz, R. Tomczak-Wandzel, J. Kumirska, E. M. Siedlecka, M. Go?ebiowski, J. Gajdus, M. Czerwicka and P. Stepnowski, “Assessing Toxicity and Biodegradation of Novel, Environmentally Benign Ionic Liquids (1-Alkoxymethyl-3-Hydroxypyridinium Chloride, Saccharinate and Acesulfamates) on Cellular and Molecular Level,” Ecotoxicology and Environmental Safety, Vol. 71, No. 1, 2008, pp. 157-165. doi:10.1016/j.ecoenv.2007.08.011

[7]   A. Romeroa, A. Santos, J. Tojob and A. Rodríguez, “To- xicity and Biodegradability of Imidazolium Ionic Liquids,” Journal of Hazardous Materials, Vol. 151, No. 1, 2008, pp. 268-273. doi:10.1016/j.jhazmat.2007.10.079

[8]   N. Bicak, “A New Ionic Liquid: 2-Hydroxyethylammonium Formate,” Journal of Mole-cular Liquids, Vol. 116, No. 1, 2005, pp. 15-18. doi:10.1016/j.molliq.2004.03.006

[9]   L. Zhai, Q. Zhong, C. He and J. Wang, “Hydroxyl Am-monium Ionic Liquids Synthesized by Water-Bath Mi-crowave: Synthesis and Desulfurization,” Journal of Ha- zardous Materials, Vol. 177, No. 1-3, 2010, pp. 807-813. doi:10.1016/j.jhazmat.2009.12.105

[10]   Rotoxkit FTM, “Freshwater toxicity test with a ciliatepro- tozoan. Standard Operational Procedure,” Creasel, Deinze, Belgium, 1998, p. 18.

[11]   Ch. Belgis and P. Guido, “Cyst-Based Toxicity Tests. XI. Influence of the Type of Food on the Intrinsic Growth Rate of the Rotifer Brachionus calyciflorus in Short- Chronic Toxicity Tests,” Chemosphere, Vol. 50, No. 3, 2003, pp. 365-372. doi:10.1016/S0045-6535(02)00496-4

[12]   J. L. Zurita, G. Repetto, A. Jos, A. del Peso, M. Salguero, M. López-Artkguez, D. Olano and A. Came?n, “Ecoto- xicological Evaluation of Diethanolamine Using a Battery of Microbiotests,” Toxicology in Vitro, Vol. 19, No. 7, 2005, pp. 879-886. doi:10.1016/j.tiv.2005.06.035

[13]   ISO 15705:2000, “Determination of the Chemical Oxygen Demand Index (ST-COD)—Small-Scale Sealed- Tube Method.”

[14]   ISO 5815:1989, “Water Quality—Determination of Bio- Chemical Oxygen Demand after 5 Day (BOD5)—Dilution and Seeding Method.”

[15]   J. Zabicky, “The Kinetics and Mechanism of Carbonyl- Methylene Condensation Reactions. Part XI. Stereochem- istry of the Products,” Journal of the Chemical Society, Vol. 137, No. 0, 1961, pp. 683-687. doi:10.1039/jr9610000683

[16]   M. G. Ahmed, U. K. R. Romman, S. M. Ahmed, K. Akhter and M. E. Halim, “Synthesis and Correlation of Spectral Properties of Some Substituted 1,3-Diphenyl-2- Propen-1-Ones,” Bangladesh Journal of Scientific and Industrial Research, Vol. 42, No. 1, 2007, pp. 45-52. doi:10.3329/bjsir.v42i1.354

[17]   S. Keskin, D. Kayrak-Talay, U. Akman and ?. Horta?su, “A Review of Ionic Liquids towards Supercritical Fluid Applications,” The Journal of Supercritical Fluids, Vol. 43, No. 1, 2007, pp. 150-180. doi:10.1016/j.supflu.2007.05.013

[18]   A. Zicmanis, S. Pavlovica, E. Gzibovska, P. Mekss and M. Klavins, “2-Hydroxyethylammonium Carboxylates— Highly Biodegradable and Slightly Toxic Ionic Liquids,” Latvian Journal of Chemistry, Vol. 3, No. 4, 2010, pp. 269-275.

[19]   A. Zicmanis, S. Pavlovica, E. Gzibovska and P. Mekss, “2- Hydroxyethylammonium Carboxylates—Catalysts and Reaction Media for Condensation Reactions,” Innovations and Technologies News, Vol. 2, No. 7, 2010, pp. 3-10.

[20]   C. Reichardt, “Polarity of Ionic Liquids Determined Em-pirically by Means of Solvatochromic Pyridinium N-Phe- nolate Betaine Dyes,” Green Chemistry, Vol. 7, No. 5, 2005, pp. 339- 351. doi:10.1039/b500106b

[21]   A. I. Vogel, “A Textbook of Practical Organic Chemistry Including Quantitative Organic Analysis,” 3rd Edition, Longmans, London, 1961, p. 718.

[22]   [J. R. Harjani, J. Farrell, M. T. Garcia, R. D. Singer and P. J. Scammells, “Further Investigation of the Biodegrad- ability of Imidazolium Ionic Liquids,” Green Chemistry, Vol. 11, No. 6, 2009, pp. 821-829. doi:10.1039/b900787c

 
 
Top