journal article·2009-04

Acetylation of β-cyclodextrin in ionic liquid green solvent

Zhao-Tie Liu, Li-Hong Shen, Zhong-Wen Liu, Jian Lu

Journal of Materials Science· Volume 44· Issue 7
Publisher page

Abstract

The ionic liquid (IL), 1-butyl-3-methylimidzolium bromide ([C4mim]Br), synthesized under supercritical CO2, was developed as a green solvent for the dissolution, regeneration and acetylation of β-cyclodextrin (β-CD). The dissolution of β-CD in [C4mim]Br of 25 wt% could be reached at 25 °C. The acetylation of β-CD was carried out under acetic anhydride in [C4mim]Br in the absence of catalyst. β-CD acetates with different degrees of substitution of 0.07–1.14 were obtained directly under the homogeneous reaction conditions. The reaction medium of IL applied can be easily recycled and reused after the synthesis of β-CD acetate. The effects of reaction time, temperature, and acetic anhydride/AGU on the acetylation of β-CD were investigated. The acetylated β-CD samples were characterized by NMR, FT-IR, and X-ray diffraction (XRD) spectroscopy. It is the first time that we have demonstrated that ILs can be used as an environmentally friendly solvent for the acetylation of β-CD, which will open a new route to acetylation of β-CD under green solvent without catalyst.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Ionic liquids properties and applications · Innovative Microfluidic and Catalytic Techniques Innovation · Chemical Synthesis and Reactions

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (27)

Show source-provided references
1. Furuta T, Kusuya Y, Neoh T, Rehmann L, Beak S, Yoshii H (2006) J Incl Phenom Macrocycl Chem 56:10710.1007/s10847-006-9070-9 ↗
2. Sutyagin AA, Glazyrin AE, Kurochkina GI, Grachev MK, Nifant’ev EE (2002) Russ J Gen Chem (Engl Transl) 72:14710.1023/A:1015378203469 ↗
3. Szejtli J (1998) Chem Rev 98:174310.1021/cr970022c ↗
4. Saenger W (1980) Angew Chem 92:34310.1002/ange.19800920505 ↗
5. Kaifer AE (1999) Acc Chem Res 32:6210.1021/ar970335u ↗
6. Schurig V, Nowotny HP (1990) Angew Chem Int Edit 29:93910.1002/anie.199009393 ↗
7. Abbott AP, Bell TJ, Handa S, Stoddart B (2005) Green Chem 7:70510.1039/b511691k ↗
8. Anastas PT, Kirchhoff MM (2002) Acc Chem Res 35:68610.1021/ar010065m ↗
9. Kazarian SG, Briscoe BJ, Welton T (2000) Chem Commun 20:204710.1039/b005514j ↗
10. Tran CD, De Paoli Lacerda SH (2002) Anal Chem 74:533710.1021/ac020320w ↗
11. Forsyth SA, MacFarlane DR, Thomsonb RJ, Itzsteinb MV (2002) Chem Commun 7:71410.1039/b200306f ↗
12. Welton T (1999) Chem Rev 99:207110.1021/cr980032t ↗
13. Wasserscheid P, Keim W (2000) Angew Chem Int Edit 39:377210.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5 ↗
14. Dupont J, de Souza RF, Suarez PAZ (2002) Chem Rev 102:366710.1021/cr010338r ↗
15. Xu W, Cooper EI, Angell CA (2003) J Phys Chem B 107:617010.1021/jp0275894 ↗
16. Biswas A, Shogren RL, Stevenson DG, Willett JL, Bhowmik PK (2006) Carbohydr Polym 66:54610.1016/j.carbpol.2006.04.005 ↗
17. Heinze T, Schwikal K, Barthel S (2005) Macromol Biosci 5:52010.1002/mabi.200500039 ↗
18. Barthel S, Heinze T (2006) Green Chem 8:30110.1039/B513157J ↗
19. Kimizuka N, Nakashima T (2001) Langmuir 17:675910.1021/la015523e ↗
20. Wu WZ, Li WJ, Han BX, Zhang ZF, Jiang T, Liu ZM (2005) Green Chem 7:70110.1039/b507845h ↗
21. Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) J Am Chem Soc 124:497410.1021/ja025790m ↗
22. Phillips DM, Drummy LF, Naik RR, Long HC, Fox DM (2005) J Mater Chem 15:4206. doi: https://doi.org/10.1039/b510069k10.1039/b510069k ↗
23. Wu J, Zhang J, Zhang H, He JS, Ren Q, Guo ML (2004) Biomacromolecules 5:26610.1021/bm034398d ↗
24. Liu CF, Sun RC, Zhang AP, Ren JL (2007) Carbohydr Polym 68:1710.1016/j.carbpol.2006.07.002 ↗
25. Adebajo MO, Frost RL (2004) Spectrochim Acta A 60:44910.1016/S1386-1425(03)00249-X ↗
26. Fang JM, Sun RC, Fowler P, Tomkinson J, Hill CAS (1999) J Appl Polym Sci 74:230110.1002/(SICI)1097-4628(19991128)74:9<2301::AID-APP20>3.0.CO;2-7 ↗
27. Cao Y, Wu J, Meng T et al (2007) Carbohydr Polym 69:66510.1016/j.carbpol.2007.02.001 ↗