Jump to main content
Jump to site search


Preorganized dual H-bond donor promotes benzoic acid active in polymerization of δ-valerolactone

Abstract

Ring-opening polymerization (ROP) of lactones catalyzed by (super)strong Brønsted acid offers valuable approach to important biodegradable aliphatic polyesters. However, the need of mild acidic catalyst in the ROPs is long sought but unmet. Here we describe a truly weak Brønsted acid, benzoic acid, in combination with a dual H-bond donor (dHBD), catalyzes ROP of δ-valerolactone (VL) in solution at room temperature. A unique preorganized sulfonyl guanidine type dHBD, 3-amino-1,2,4-benzothiadiazine-1,1-dioxide (ABTD), shows to be optimal to work with benzoic acid as cocatalyst, promotes benzoic acid active in ROPs of VL. Poly-δ-valerolactones of predictable molecular weights (from 2.13 to 9.33 kg mol−1) and narrow dispersities (Đ ≤ 1.16) are synthesized. The controlled characters of the ROPs are verified by NMR, SEC, and MALDI-ToF MS measurements. NMR titration experiments imply ABTD preferentially binding with benzoic acid, and benzoic acid/ABTD pair protonates VL monomer. Weak benzoic acid is not weak for the first time in efficient cationic ROP of VL by protonation mechanism.

Back to tab navigation

Supplementary files

Publication details

The article was accepted on 03 Aug 2017 and first published on 07 Aug 2017


Article type: Paper
DOI: 10.1039/C7PY01192J
Citation: Polym. Chem., 2017, Accepted Manuscript
  •   Request permissions

    Preorganized dual H-bond donor promotes benzoic acid active in polymerization of δ-valerolactone

    H. Sun, S. Xu, Z. Li, J. Xu, J. Liu, X. Wang, H. Wang, H. Dong, Y. Liu and K. Guo, Polym. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7PY01192J

Search articles by author

Spotlight

Advertisements