Abstract
Biphasic esterification of model aqueous solutions of crystalline succinic acid or culture liquid obtained as a result of the growth of a succinic acid producer Yarowia lypolitica was studied. The main part of the study was performed with isooctyl (2-ethylhexyl) alcohol. Laurylsulfonic acid (another name dodecylsulfonic acid) was introduced as a catalyst. It was shown that the diester yield increases with an increase in the ratio alcohol/succinic acid solution, and it was higher than 90% when the ratio was 2 : 1. At a constant ratio of the phases described above, the product yield increased with a decrease in the concentration of succinic acid in the aqueous solution. More than 10% of the DSA catalyst passes into the alcohol phase; the compound can be extracted by Na2CO3 solution. The application of real culture liquid resulted in a significant decrease in the product yield as compared to the model succinic acid solutions. The process may become industrially promising with the selection of other efficient catalysts and improved microbial fermentation in order to decrease the content of related organic acid in the culture liquid.
Similar content being viewed by others
REFERENCES
Debabov, V.G., Bio-succinic acid production prospects, Biotekhnologiya, 2015, vol. 2, pp. 27–32.
Saxena, R.K., Sarans, S., Isar, J., and Koushi, K.R., Production and application of succinic acid, in Current Development in Biotechnology and Bioengineering, Pandey, A., Negi, S., and Soccol, C.R., Eds., 2017, pp. 601–630.
Cheng, K.-K., Zhao, X.-B., Zeng, J., et al., Down stream processing of biotechnological produced succinic acid, Appl. Microbiol. Biotechnol., 2012, vol. 95, pp. 841–850. doi 10.1007/s00253-012-4214-x
Demina, N.G., Rumyantseva, N.F., Antonova, S.V., et al., Isolation of succinic acid from fermentation solutions by direct crystallization, Biotekhnologiya, 2015, vol. 6, pp. 52–57.
Orjnela, A., Orjnela, A., Lira, C.T., and Miller, D.Y., A novel process for recovery of fermentation-derived succinic acid: process design and economic analysis, Biores. Technol., 2013, vol. 139, pp. 235–241. doi 10.1016/j.biortech.2013.03.174
Delhome, C., Goh, S.L., Kuhn, F.E., and Wenster-Botz, D., Esterification of bio-based succinic acid in biphase system: comparison of chemical and biological catalyses, Mol. Catalysis B: Enzymatic, 2012, vol. 80, pp. 39–47. doi 10.1016/j.molcatb.2012.03.010
Stuart, A., McCallum, M.M., Fan, D., et al., Poly(vinilchloride) plasticized with succinate esters: synthesis and characterization, Polymer. Bull., 2010, vol. 65, pp. 589–598. doi 10.1016/j.eurpolymj.2013.06.023
Stuart, A., Le Captain D.J., Lee C.Y., and Mohanty D.K. Poly(vinylchloride) plasticized with mixtures of succinate di-esters - synthesis and characterization, Eur. Polymer J., 2013, vol. 49, pp. 2785–2791. doi 10.1016/j.eurpolymj.2013.06.023
Facklam, T., Succinic acid alkyl ester mixtures used as plasticizers (Laxnees Deutschland GmbH BioAmber Instructional S.A.R.L), US Patent no. 9 676 923, 2017.
Sokoloff, R.L. and Frigon, R.P., Rapid spectrophotometric assay of dodecyl sulfate using acridine orange, Anal. Biochem., 1981, vol. 118, pp. 138–141. doi 10.1016/0003-2697(81)90169-X
ACKNOWLEDGEMENTS
We are grateful to Yu.V. Skvorniakov (LLC Globalkhimfarm), S.B. Gomboeva (LLC Globalkhimfarm), and P.Yu. Bondarenko (NRC Kurchatov Institute, GOSNIIGENETIKA) for the analytical support of the work.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by V. Mittova
List of abbreviations: GC—gas chromatography, CL—culture liquid; OP—optical density; AO—acridine orange, DBSA—dodecylbenzenesulfonic acid; DSA—dodecylsulfonic acid, SDS—sodium dodecyl sulfate.
Rights and permissions
About this article
Cite this article
Lukianov, D.A., Debabov, V.G. Obtainment of Succinic Acid and Higher Alcohols (C8–С10) Diesters by Biphasic Esterification. Appl Biochem Microbiol 54, 863–868 (2018). https://doi.org/10.1134/S0003683818090053
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0003683818090053