TECHNOLOGICAL AND ECOLOGICAL ASPECTS OF SURFACTANTS PRODUCTION

Keywords: surfactants, enzymatic esterification, lipase, non-aqueous medium, sugar fatty acid esters

Abstract

Surfactants are used in various industries: in foods, pharmaceuticals, textiles, personal care products, detergents, polymers, paints and coatings, etc. Scientific researches of technological and ecological aspects of surfactants (sugars fatty acids esters) production are carried out. Traditionally, sugars fatty acids esters are synthesized by chemical methods (using high temperature and pressure, in the presence of basic or acid catalysts and organic solvents). Replacing chemical catalysts with enzymes is an example of “green” production. Various approaches to the use of a non-aqueous medium for biocatalytic esterification are reviews. The most ecological approach is determined – esterification in a solvent-free environment, which ensures improved enzyme activity retention, the absence of costs associated with solvent usage and recovery, facilitates further product purification, reduces the impact on the environment, increases safety in the workplace.

References

Infante, M.R., Perez L., Pinazo A. (2004), “Amino acid-based surfactants”, Comptes Rendus Chimie. 7, 583–592.

Clapés, P., Infante, M. R. (2002), “Amino Acid-based Surfactants: Enzymatic Synthesis, Properties and Potential Applications”, Biocatalysis and Biotransformation, 20 (4), 215-233.

Hayes D. G. (2012), “Using enzymes to prepare biobased surfactants”. Retrieved from https://www.aocs.org/stay-informed/inform-magazine/featured-articles/using-enzymes-to-prepare-biobased-surfactants-july/august-2012

Feuge, R.O., Zerinque, H.J., Weiss, T.J., Brown, M. (1970), “Preparation of Sucrose Esters by Interesterification”, Journal of the American Oil Chemists Society, 47 (2), 56-60.

Cauglia, F., Canepa, P. (2008), “The enzymatic synthesis of glucosylmyristate as a reaction model for general considerations on ‘sugar esters’ production”, Bioresource Technology, 99 (10), 4065-4072.

Hill, K., Rhode O. (1999), “Sugar-based surfactants for consumer products and technical applications”, Fett-Lipid, 101 (1), 25-33.

Polat, T. and Linhardt R.J. (2001), “Synthesis and applications of sucrose-based esters”, Journal of Surfactants and Detergents, 4, 415-421.

Lee, M.Y. and. Dordick, J.S. (2002), “Enzyme activation for nonaqueous media”, Current Opinion in Biotechnology, 13 (4), 376-384.

Walsh, M.K., et al. (2009), “Synthesis of lactose monolaurate as influenced by various lipases and solvents”, Journal of Molecular Catalysis B-Enzymatic, 60 (3- 4), 171-177.

Arcos, J.A., Bernabe, M., Otero, C. (1998), “Quantitative enzymatic production of 6- O-acylglucose esters”, Biotechnology and Bioengineering, 57 (5), 505- 509.

Cao, L.Q., et al. (1997), “Lipase-catalyzed solid phase synthesis of sugar fatty acid esters”, Biocatalysis and Biotransformation, 14 (4), 269-283.

Khaled, N., et al. (1991), “Fructose Oleate Synthesis in a Fixed Catalyst Bed Reactor”, Biotechnology Letters, 13(3), 167-172

Ward, O.P., Fang, J.W., Li, Z.Y. (1997), “Lipase-catalyzed synthesis of a sugar ester containing arachidonic acid”, Enzyme and Microbial Technology, 20 (1), 52-56.

Oguntimein, G.B., Erdmann, H., Schmid, R.D. (1993), “Lipase Catalyzed Synthesis of Sugar Ester in Organic-Solvents”, Biotechnology Letters, 15 (2), 175- 180.

Yadav, G.D. and Lathi, P.S. (2005), “Lipase catalyzed transesterification of methyl acetoacetate with n-butanol”, Journal of Molecular Catalysis B-Enzymatic, 32 (3), 107-113.

Xiaoming, Z., et al. (2002), “Lipase-catalyzed synthesis of 6-O-vinylacetyl glucose in acetonitrile”, Biotechnology Letters, 24 (13), 1097- 1100.

Ren, K., Lamsal, B. P. (2017), “Synthesis of some glucose-fatty acid esters by lipase from Candida Antarctica and their emulsion functions”, Food Chemistry, 214(1), 556-563.

Marathe, S.J., Shah, N.N., Singhal, R.S. (2020), “Enzymatic synthesis of fatty acid esters of trehalose: Process optimization, characterization of the esters and evaluation of their bioactivities”, Bioorganic Chemistry, 94, 103460.

Akoh, C.C. (1994), “Enzymatic synthesis of acetylated glucose fatty acid esters in organic solvent”, Journal of the American Oil Chemists’ Society, 71, 319–323.

Sabeder, S., Habulin, M., Knez, Z. (2006), “Lipase-catalyzed synthesis of fatty acid fructose esters”, Journal of Food Engineering, 77(4), 880-886.

Yijing, M., Gong, Y., Goddard, J.M., Abbaspourrad, F. (2018), “Synthesis and characterization of lactose fatty acid ester biosurfactants using free and immobilized lipases in organic solvents”, Food Chemistry, 266 (15), 508-513.

Carrea, G., Ottolina, G., Riva, S. (1995), “Role of Solvents in the Control of Enzyme Selectivity in Organic Media”, Trends in Biotechnology, 13 (2), 63-70.

Hayes, D.G. (2004), “Enzyme-catalyzed modification of oilseed materials to produce eco-friendly products”, Journal of the American Oil Chemists Society, 81 (12), 1077-1103.

Ganske, F., Bornscheuer, U.T. (2005), “Optimization of lipase-catalyzed glucose fatty acid ester synthesis in a two-phase system containing ionic liquids and t-BuOH”, Journal of Molecular Catalysis B-Enzymatic, 36 (1-6), 40-42.

Villeneuve, P. (2007), “Lipases in lipophilization reactions”, Biotechnology Advances, 25 (6), 515-536.

Chang, S.W., Shaw, J.F. (2009), “Biocatalysis for the production of carbohydrate esters”, New Biotechnology, 26 (3-4), 109-116.

Degn, P. and Zimmermann, W. (2001), “Optimization of carbohydrate fatty acid ester synthesis in organic media by a lipase from Candida Antarctica”, Biotechnology and Bioengineering, 74 (6), 483-491.

Ferrer, M., et al. (2005), “Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties”, Enzyme and Microbial Technology, 36 (4), 391-398.

Gill, I., Vulfson, E. (1994), “Enzymatic Catalysis in Heterogeneous Eutectic Mixtures of Substrates”, Trends in Biotechnology, 12 (4), 118-122.

Gill, I., Vulfson, E.N. (1993), “Enzymatic-Synthesis of Short Peptides in Heterogeneous Mixtures of Substrates”, Journal of the American Chemical Society, 115 (8), 3348-3349.

Cao, L.Q., Bornscheuer, U.T., Schmid, R.D. (1996), “Lipase-catalyzed solid phase synthesis of sugar esters”, Fett-Lipid, 98 (10), 332-335.

Cao, L.Q., Bornscheuer, U.T., Schmid, R.D. (1999), “Lipase-catalyzed solid-phase synthesis of sugar esters. Influence of immobilization on productivity and stability of the enzyme”, Journal of Molecular Catalysis B-Enzymatic, 6 (3), 279-285.

Sabeder, S., Habulin, M., Knez, Z. (2005), “Comparison of the esterification of fructose and palmitic acid in organic solvent and in supercritical carbon dioxide”, Industrial & Engineering Chemistry Research, 44 (25), 9631- 9635.

Tai, H.P., Brunner, G. (2009), “Sugar fatty acid ester synthesis in high-pressure acetone-CO2 system”, Journal of Supercritical Fluids, 48 (1), 36-40.

Tsitsimpikou, C., et al. (1998), “Acylation of glucose catalysed by lipases in supercritical carbon dioxide”, Journal of Chemical Technology and Biotechnology, 71 (4), 309-314.

Kragl, U., Eckstein, M., Kaftzik, N. (2002), “Enzyme catalysis in ionic liquids”, Current Opinion in Biotechnology, 13 (6), 565-571.

van Rantwijk, F., Lau, R.M., Sheldon, R.A. (2003), “Biocatalytic transformations in ionic liquids”, Trends in Biotechnology, 21 (3), 131-138.

Park, S., Kazlauskas, R.J. (2003), “Biocatalysis in ionic liquids - advantages beyond green technology”, Current Opinion in Biotechnology, 14 (4), 432-437.

Sureshkumar, M., Lee, C.K. (2009), “Biocatalytic reactions in hydrophobic ionic liquids”, Journal of Molecular Catalysis B-Enzymatic, 60 (1-2), 1-12.

Gangu, S.A., Weatherley, L.R., Scurto, A.M. (2009), “Whole-Cell Biocatalysis with Ionic Liquids”, Current Organic Chemistry, 13 (13), 1242-1258.

Kaar., J.L. (2003), “Impact of Ionic Liquid Physical Properties on Lipase Activity and Stability”. Journal of the American Chemical Society, 125 (14), 4125- 4131.

Ganske, F. Bornscheuer, U.T. (2005), “Lipase-catalyzed glucose fatty acid ester synthesis in ionic liquids”, Organic Letters, 7 (14), 3097-3098.

Ye, Ran (2011), "Bioreactor system design for lipase-catalized synthesis of saccharide-fatty acid esters in solvent-free media”.

Foresti, M.L., et al. (2007), “Multiple effects of water on solvent-free enzymatic esterifications”, Enzyme and Microbial Technology. 41 (1-2). 62-70.

Ogawa, S., Endo, A., Kitahara, N., et al. (2019), “Factors determining the reaction temperature of the solvent-free enzymatic synthesis of trehalose esters”, Carbohydrate Research, 482 (8), 107-139.

Fregapane, G., Sarney, D.B., Vulfson, E.N. (1991), “Enzymatic Solvent-Free Synthesis of Sugar Acetal Fatty-Acid Esters”, Enzyme and Microbial Technology, 13 (10). 796-800.

Ye, Ran, Hayes, D.G., Burton, R., Liu, A. (2016), “Solvent-Free Lipase-Catalyzed Synthesis of Technical-Grade Sugar Esters and Evaluation of Their Physicochemical and Bioactive Properties”, Catalysts, 6 (6), 78-82.

Pyo, S.H., Hayes, D.G. (2008), “Desorption of Fructose from a Packed Column to an Oleic Acid/Fructose Oleate Mixture for Employment in a Bioreactor System”, Journal of the American Oil Chemists Society, 85 (11), 1033-1040.

Pyo, S.H., Hayes, D.G. (2009), “Designs of Bioreactor Systems for Solvent-Free Lipase-Catalyzed Synthesis of Fructose-Oleic Acid Esters”, Journal of the American Oil Chemists Society, 86 (6), 521-529.

Views:

187

Downloads:

164

Published
2020-12-01
Citations
How to Cite
Osmanova Olha. (2020). TECHNOLOGICAL AND ECOLOGICAL ASPECTS OF SURFACTANTS PRODUCTION. Science Review, (8(35). https://doi.org/10.31435/rsglobal_sr/30122020/7298
Section
Chemistry