Journal
CARBOHYDRATE POLYMERS
Volume 132, Issue -, Pages 565-573Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carbpol.2015.06.052
Keywords
Olefin metathesis; Amides; Solvents; Acetic acid; Cellulose esters; Click reactions
Categories
Funding
- National Science Foundation [DMR-1308276]
- Institute for Critical Technologies and Applied Science at Virginia Tech
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1308276] Funding Source: National Science Foundation
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [1309218] Funding Source: National Science Foundation
Ask authors/readers for more resources
Cellulose esters with amide functionalities were synthesized by cross-metathesis (CM) reaction of terminally olefinic esters with different acrylamides, catalyzed by Hoveyda-Grubbs 2nd generation catalyst. Chelation by amides of the catalyst ruthenium center caused low conversions using conventional solvents. The effects of both solvent and structure of acrylamide on reaction conversion were investigated. While the inherent tendency of acrylamides to chelate Ru is governed by the acrylamide N-substituents, employing acetic acid as a solvent significantly improved the conversion of certain acrylamides, from 50% to up to 99%. Homogeneous hydrogenation using p-toluenesulfonyl hydrazide successfully eliminated the alpha,beta-unsaturation of the CM products to give stable amide-functionalized cellulose esters. The amide-functionalized product showed higher T-g than its starting terminally olefinic counterpart, which may have resulted from strong hydrogen bonding interactions of the amide functional groups. (C) 2015 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available