A novel, efficient procedure for acylation of cellulose under homogeneous solution conditions

✍ Scribed by Guilherme A. Marson; Omar A. El Seoud

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 127 KB
• Volume: 74
• Category: Article
• ISSN: 0021-8995
• DOI: 10.1002/(sici)1097-4628(19991107)74:6<1355::aid-app5>3.0.co;2-m

✦ Synopsis

Commercially available cellulose (Avicel PH101) was successfully acylated under homogeneous solution conditions by the following novel procedure: 2.0 g of cellulose and 5.0 g of LiCl were introduced into a glass reactor, magnetic stirring was started, the pressure was reduced to 2 mmHg, the temperature was raised to 110°C in 30 min, and the reactor was kept under these conditions for another 30 min. N,N-Dimethylacetamide, 60 mL, was introduced, atmospheric pressure was restored, and the temperature was raised to 150°C in 30 min. The system was kept under these conditions for 1 h, then the temperature was decreased to 40°C; in 2 h a clear cellulose solution was obtained. Acid anhydride was added, and the solution was stirred at 60°C for additional 18 h. Acetates, propionates, butyrates, and acetate/butyrate mixed ester were prepared with excellent reproducibility of the degree of substitution, from 1 to 3. The degree of polymerization of cellulose is negligibly affected by these reaction conditions. The distribution of the acetyl moiety among the three OH groups of the anhydroglucose unit follows the order C 6 Ͼ C 2 Ͼ C 3 . Features relevant to the industrial application of this novel procedure are discussed.