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Crystals 2017, 7(10), 284; doi:10.3390/cryst7100284

Effect of Ionic Liquids on the Separation of Sucrose Crystals from a Natural Product Using Crystallization Techniques

1
College of Pharmacy, CHA University, Sungnam 13844, Korea
2
Department of Chemistry and Energy Systems Research, Ajou University, Suwon 16499, Korea
3
College of Pharmacy, Kyungpook National University, Daegu 41566, Korea
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Helmut Cölfen
Received: 26 August 2017 / Revised: 18 September 2017 / Accepted: 20 September 2017 / Published: 23 September 2017
(This article belongs to the Special Issue Ionic Liquids in Drug Delivery)
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Abstract

The present work aims to investigate the applicability of ionic liquids (ILs) for natural ingredient crystallization. First, the medicinal plant, namely Angelica gigas Nakai, was extracted using methanol (MeOH) as a solvent. Afterwards, ILs 1-butyl-3-methylimidazolium tetrafluoroborate (BMImBF4), 1-butyl-3-methylimidazolium hexafluorophosphate (BMImPF6), 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (BMImTFSI), 1-allyl-3-ethylim idazolium tetrafluoroborate (AEImBF4), and 1,3-diallyl imidazolium tetrafluoroborate (AAImBF4), in three ratios of 1:1, 1:2, and 1:3 (extraction solution/ILs (v/v)) were used as an anti-solvent to induce crystallization. Crystals were obtained within 8 h and were then identified to be pure crystals of sucrose through nuclear magnetic resonance (1H-NMR) analysis. Moreover, the single-crystal X-ray diffraction (SXD) analysis revealed all recovered crystals have an identical crystal structure and the morphology was monitored using a video microscope. With the application of BMImBF4 and BMImPF6, transformation of sucrose crystal morphology from an elongated hexagon shape to an elongated rectangular shape was observed with respect to the respective concentration increase. Here, all crystals precipitated from BMImBF4 and BMImPF6 were found to possess identical PXRD patterns. However, when BMImTFSI was employed, small rectangular crystals attached to the larger rectangular-shaped crystals due to secondary nucleation and shapeless amorphous forms were observed according to the alteration in the solution to ILs ratio. Accordingly, the ability of ILs as a relevant anti-solvent for the selective crystallization of a single compound from a natural product was assessed through the study. Furthermore, the applicability of ILs as crystal engineering solvents are expected to modify both the solid state and the crystal morphology of natural compounds, which can influence drug manufacturability, dissolution rate, and bioavailability. View Full-Text
Keywords: ionic liquid; natural product; crystallization; sucrose; crystal morphology ionic liquid; natural product; crystallization; sucrose; crystal morphology
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MDPI and ACS Style

An, J.-H.; Kiyonga, A.N.; Yoon, W.; Park, M.; Lim, C.; Yun, Y.; Park, G.-H.; Jung, K. Effect of Ionic Liquids on the Separation of Sucrose Crystals from a Natural Product Using Crystallization Techniques. Crystals 2017, 7, 284.

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