Sains Malaysiana 47(7)(2018): 1473–1482

http://dx.doi.org/10.17576/jsm-2018-4707-15

 

Interaction Study of Binary Solvent Systems Ionic Liquid and Deep Eutectic Solvent with Rotenone

(Kajian Interaksi Sistem Pelarut Binari Cecair Ionik dan Pelarut Eutektik Dalam dengan Rotenon)

 

ZETTY SHAFIQA OTHMAN¹, MAMORU KOKETSU², NURUL HUDA ABD KARIM¹,

SAIFUL IRWAN ZUBAIRI¹ & NUR HASYAREEDA HASSAN^1*

 

¹School of Chemical Science and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

 

²Department of Chemistry and Bimolecular Science, Faculty of Engineering, Gifu University, Gifu, Japan

 

Received: 28 November 2017/Accepted: 4 March 2018

 

ABSTRACT

[BMIM]OTf and alcohol-based DES combination with a selected organic solvent (acetone and acetonitrile) have been proven to efficiently extracting rotenone (isoflavonoid biopesticide) compound compared to individual organic solvents. Their efficiency builds up interest to study the solvent-solute interaction that occurs between both selected solvent systems with rotenone. The interaction study was analyzed using FTIR, 1D-NMR and 2D- NMR (NOESY, HMBC). Correlation portrayed by NOESY and HMBC of [BMIM]OTf - standard rotenone mixture predicted probable hydrogen bonding between the oxygen of rotenone with acidic proton C2-H of [BMIM]OTf. While for the alcohol-based DES-rotenone mixture, the correlation shows probable interaction to occur between methyl and methoxy group rotenone with the hydroxyl group of 1,4-butanediol. In conclusion, potential hydrogen bonding that occurs between solvent and solute aid towards the solvent efficiency in extracting rotenone compound while emphasizing on the low cost and green mediated solvent systems.

 

Keywords: Biopesticide; deep eutectic solvent; extraction; ionic liquid; solvent-solute interaction

 

ABSTRAK

Gabungan [BMIM]OTf dan DES berasaskan alkohol dengan pelarut organik terpilih (aseton dan asetonitril) terbukti cekap dalam mengekstrak sebatian rotenon (biopestisid isoflavonoid) berbanding pelarut organik. Kecekapan tersebut menarik minat untuk mengkaji interaksi pelarut -bahan larut yang berlaku antara kedua-dua sistem pelarut terpilih dengan rotenon. Kajian interaksi dikaji menggunakan FTIR, 1D-NMR dan 2D- NMR (NOESY, HMBC). Korelasi yang digambarkan oleh NOESY dan HMBC bagi campuran [BMIM]OTf - rotenon piawai menunjukkan potensi ikatan hidrogen antara oksigen rotenon dengan proton berasid C2-H [BMIM]OTf. Bagi campuran DES berasaskan alkohol-rotenon, korelasi menunjukkan interaksi berpotensi berlaku antara metil dan kumpulan metoksi rotenon dengan kumpulan hidroksil 1,4-butanediol. Kesimpulannya, potensi ikatan hidrogen yang wujud antara pelarut dan bahan larut membantu ke arah kecekapan pelarut dalam pengekstrakan sebatian rotenon selain faktor kos yang rendah dan sistem pelarut pengantara yang hijau.

 

Kata kunci: Biopestisid; cecair ionik; interaksi pelarut-bahan larut; pelarut eutektik dalam; pengekstrakan

REFERENCES

Abbott, A.P., Capper, G., Davies, D.L., Rasheed, R.K. & Tambyrajah, V. 2003. Novel solvent properties of choline chloride/urea mixtures. Chemical Communications (1): 70-71.

Abbott, A.P., Boothby, D., Capper, G., Davies, D.L. & Rasheed, R.K. 2004. Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids. Journal of the American Chemical Society 126(29): 9142-9147.

Bi, W., Tian, M. & Row, K.H. 2013. Evaluation of alcohol-based deep eutectic solvent in extraction and determination of flavonoids with response surface methodology optimization. Journal of Chromatography A 1285: 22-30.

Bogdanov, M.G., Petkova, D., Hristeva, S., Svinyarov, I. & Kantlehner, W. 2010. New guanidinium-based room temperature ILs substituent and anion effect on density and solubility in water. Zeitschrift f¨ur Naturforschung B 65(1): 37-48.

Carson, P.A. 2002. Hazardous Chemicals Handbook. 2nd ed. Boston: Butterworth- Heinemann.

Dai, Y., Van, S.J., Witkamp, G.J., Verpoorte, R. & Choi, Y.H. 2013. Natural deep eutectic solvents as new potential media for green technology. Analytica Chimica Acta 766: 61-68.

Freemantle, M. 2010. An Introduction to Ionic Liquid. Cambridge: Royal Society of Chemistr.

Li, Y.Z., Li, G.H., Wei, X.Y., Liu, Z.H. & Xu, H.H. 2011. Isolation and identification of insecticidal compounds from Tephrosia purpurea (Fabaceae) bark and their insecticidal activity. Acta Entomologica Sinica 54(12): 1368-1376.

Othman, Z.S., Hassan, N.H. & Zubairi, S.I. 2017. Response surface optimization of rotenone using natural alcohol-based deep eutectic solvent as additive in the extraction medium cocktail. Journal of Chemistry 2017: 1-10.

Othman, Z.S., Hassan, N.H. & Zubairi, S.I. 2015. Alcohol based-deep eutectic solvent (DES) as an alternative green additive to increase rotenone yield. In AIP Conference Proceedings 1678(1): 050004.

Park, J.H., Oh, K.W. & Choi, H.M. 2013. Preparation and characterization of cotton fabrics with antibacterial properties treated by crosslinkable benzophenone derivative in choline chloride-based deep eutectic solvents. Cellulose 20(4): 2101-2114.

Sasidharan, S., Chen, Y., Saravanan, D., Sundram, K.M. & Yoga, L. 2011. Extraction, isolation and characterization of bioactive compounds from plants extracts. African Journal of Traditional, Complementary and Alternative Medicines 8(1): 1-10.

Shamsuri, A.A. & Daik, R. 2012. Plasticizing effect of choline chloride/urea eutectic-based ionic liquid on physicochemical properties of agarose films. BioResources 7(4): 4760-4775.

 

 

*Corresponding author; email: syareeda@ukm.edu.my