Sulfamic Acid as A Cost-Effective Catalyst for Synthesis of α-Acyloxyacrylate Esters as Candidate Monomers for Biobased Polymers by Acylation of Pyruvate Esters

Abstract

Sulfamic acid was used as an efficient catalyst and green alternative for metal-containing acidic material to promote the acylation of pyruvate esters to produce α-acyloxyacrylate esters, which were candidate monomers for biobased polymers. Polymers from these monomers were useful materials for bio-based plastics, which showed high heat resistance and transparency. A series of α-acyloxyacrylate esters were converted from pyruvate esters by using sulfamic acid as a catalyst and good yields were obtained. The reaction in the presence of the sulfamic acid catalyst was carried out in the liquid phase and showed greater productivity than synthesis with a conventional liquid inorganic acid.

GRAPHICAL ABSTRACT

Keywords:

• α-Acyloxyacrylate esters
• homogeneous catalysis
• pyruvate esters
• sulfamic acid

ACKNOWLEDGMENT

This work was financially supported by the National Natural Science Foundation of China (Grant No. 20803032).

Notes

^a Reaction conditions: 0.2 mmol of catalyst, 1 mmol of 1b, 10 mmol of 2a, 10 mmol of acetic acid; reaction temperature: 363 K; reaction time: 2 h.

^a Reaction conditions: 0.2 mmol of H₂NSO₃H, 1 mmol of 1b, 10 mmol of 2a, 10 mmol of solvent; reaction temperature: 363 K; reaction time: 2 h.

^a Reaction conditions: 0.2 mmol of H₂NSO₃H, 1 mmol of 1, 10 mmol of 2, 10 mmol of carboxylic acid; reaction temperature: 363 K; reaction time: 2 h.