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Merck

Time and energy-efficient homogeneous transesterification of cellulose under mild reaction conditions.

Carbohydrate polymers (2016-12-19)
Jiajia Ding, Chengguo Li, Jian Liu, Yuqing Lu, Guanghui Qin, Lihui Gan, Minnan Long
ABSTRACT

In this research, cellulose aliphatic esters (CEs) were synthesized efficiently in an N, N-dimethylacetamide/lithium chloride system (DMAc/LiCl) with vinyl esters (VEs, number of carbon atoms ranging from 4 to 12) as acylation reagent and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) as catalyst. The structures and properties of the products have been characterized by various analytical techniques. The key concept in this cellulose modification was the achievement the degree of substitution (DS) >2.75 at much milder temperature and shorter reaction time (under 30°C within 15min-30min), other than previous research. Generally, the DS of obtained CEs showed a reverse trend with the length of the aliphatic chain increasing. The priority of reactions in three positions of the CEs followed the same order of C6>C2>C3 for a homogeneous conversion. There was no decrease of molecule weight under this mild reaction. This research provides a novel homogeneous technology to synthesize various CEs efficiently.

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Sigma-Aldrich
Vinyl butyrate, contains 20 ppm 4-methoxyphenol as stabilizer, ≥99.0% (GC)
Sigma-Aldrich
Vinyl propionate, contains <100 ppm monomethyl ether hydroquinone as inhibitor, 98%