Biginelli reaction on cellulose acetoacetate: a new approach for versatile cellulose derivatives

Liduo Rong; Min Zeng; Hongchen Liu; Bijia Wang; Zhiping Mao; Hong Xu; Linping Zhang; Yi Zhong; Jinying Yuan; Xiaofeng Sui

doi:10.1016/j.carbpol.2019.01.036

Biginelli reaction on cellulose acetoacetate: a new approach for versatile cellulose derivatives

Carbohydr Polym. 2019 Apr 1:209:223-229. doi: 10.1016/j.carbpol.2019.01.036. Epub 2019 Jan 11.

Authors

Liduo Rong¹, Min Zeng², Hongchen Liu¹, Bijia Wang³, Zhiping Mao⁴, Hong Xu⁴, Linping Zhang⁴, Yi Zhong⁴, Jinying Yuan⁵, Xiaofeng Sui⁶

Affiliations

¹ Key Lab of Science and Technology of Eco-textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, People's Republic of China.
² Key Lab of Organic Optoelectronics and Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, 100084, People's Republic of China.
³ Key Lab of Science and Technology of Eco-textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, People's Republic of China; Key Lab of High Performance Fibers & Products, Ministry of Education, Donghua University, Shanghai, 201620, People's Republic of China; Innovation Center for Textile Science and Technology of DHU, Donghua University, Shanghai, 201620, People's Republic of China.
⁴ Key Lab of Science and Technology of Eco-textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, People's Republic of China; Innovation Center for Textile Science and Technology of DHU, Donghua University, Shanghai, 201620, People's Republic of China.
⁵ Key Lab of Organic Optoelectronics and Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing, 100084, People's Republic of China. Electronic address: yuanjy@mail.tsinghua.edu.cn.
⁶ Key Lab of Science and Technology of Eco-textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, People's Republic of China; Key Lab of High Performance Fibers & Products, Ministry of Education, Donghua University, Shanghai, 201620, People's Republic of China; Innovation Center for Textile Science and Technology of DHU, Donghua University, Shanghai, 201620, People's Republic of China. Electronic address: suixf@dhu.edu.cn.

PMID: 30732803
DOI: 10.1016/j.carbpol.2019.01.036

Abstract

The Biginelli multicomponent reaction has been used as an effective and model method to efficiently prepare a library of cellulose derivatives based on cellulose acetoacetate (CAA). Various cellulose derivatives containing 3, 4-dihydropyrimidin-2(1 H)-ones (DHPMs) with different functional groups (carboxyl, methoxyl, and nitro) are synthesized. The entire reaction process is followed using FT-IR, ¹H NMR. The results demonstrate that more than 80% of the acetoacetyl groups are converted within four hours. Additionally, all the cellulose derivatives are confirmed to have favorable thermostability and good solubility in selected solvents. Furthermore, polymers (in this case, poly (ethylene glycol) monomethyl ether (mPEG)) can also be anchored to the cellulose backbone via this facile modular approach. Therefore, the Biginelli multicomponent reaction offers a straightforward method for diverse and large-scale cellulose derivatization. These results are expected to prompt broader study of this multicomponent reaction in interdisciplinary fields.

Keywords: Aldehyde; Biginelli reaction; Cellulose acetoacetate; Multicomponent functionalization; Urea.