Solubility of Cellulose in Binary Mixtures of 1-Alkyl-3-methylimidazolium Acetate and Dimethyl Sulfoxide: Influence of Alkyl Chain Length in the Cation
Yuta Tomimatsu A , Yukihiro Yoshimura B and Akio Shimizu A CA Graduate School of Environmental Engineering for Symbiosis, Soka University, 1-236 Tangi, Hachioji, Tokyo 192-8577, Japan.
B Department of Applied Chemistry, National Defence Academy, 1-10-20 Hashirimizu, Yokosuka, Kanagawa 239-8686, Japan.
C Corresponding author. Email: shimizu@soka.ac.jp
Australian Journal of Chemistry 72(9) 669-673 https://doi.org/10.1071/CH19047
Submitted: 30 January 2019 Accepted: 15 May 2019 Published: 4 June 2019
Abstract
The influence of alkyl chain length of cations on cellulose solubility in a neat imidazolium (MIM)-based ionic liquid (IL) [CnMIM][OAc] and [CnMIM][OAc]–DMSO binary system (n = 0–6) was investigated. The correlation between cellulose solubility and Kamlet–Taft hydrogen bond basicity (β) was also examined. Cellulose solubility (g per mol IL) in neat [CnMIM][OAc] increased as the cation alkyl chain length decreased from 6 to 2. However, alkyl chain lengths of 1 and 0 resulted in extremely poor cellulose solubility, indicating that a chain length of 2 was optimal for dissolution of cellulose in the system. Cellulose solubility in the [CnMIM][OAc]–DMSO binary system (n = 1–6) was greater than that in neat IL, with maximum solubility occurring at an IL mole fraction of ~0.2. Maximum cellulose solubility in the [CnMIM][OAc]–DMSO binary system was slightly better at even alkyl chain lengths (n = 2, 4, or 6) than at odd chain lengths (n = 1, 3, or 5), with the best solubility at n = 4. More interestingly, maximum cellulose solubility and specific IL mole fraction in the IL-DMSO binary system were related with the β values of neat ILs, even with ILs containing different anionic species or cation alkyl chain lengths. This indicates that solubility information in IL-DMSO binary systems is influenced by the characteristics of neat ILs.
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