Ring Opening Metathesis Polymerization of 7-Oxabicyclo[2.2.1]Hept-5-Ene-2,3- Dicarboxylic Acid, Dimethyl Ester

Beata Kwasek,Dariusz Bogdał

doi:10.3390/ecsoc-18-d009

Abstract

All the monomers used in ring opening metathesis polymerization ( ROMP) were synthesized by two step reactions. The first step of the synthesis was the Diels-Alder reaction between furan and maleic anhydride to produce exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride. The second step was to prepared 7-oxabicyclo[2.2.1]hept-5-ene-2,3- dicarboxylic acid, dimethyl ester by Fischer estrification of exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride in refluxing methanol.7-Oxabicyclo[2.2.1]hept-5-ene-2,3- dicarboxylic acid, dimethyl ester was polymerized by ROMP catalyzed by commercially available ruthenium catalyst Ru(PPh3)2(Cl)2(CHPh) at defined concentrations relative to the monomer. Depending on the molar ratio of the monomer to the catalyst polymers with different large molecular weight were obtained. Molecular weights and polydispersities were confirmed by gel permeation chromatography. Monomers and polymers were also analyzed by FT-IR.Polyanions of poly (7-oxanorbornene-2,3-dicarboxylate) were prepared by hydrolysis of poly (dimethyl-7-oxabicyclo (2.2.1) hept-5-ene-2,3-dicarboxylic acid).It is worth noting that the polyanions in aqueous solution form a gel, were lubricious.The properities of the prepared polymers will be discussed in full paper.

Highlights

Ring-opening metathesis polymerization (ROMP) is a type of cycloolefin polymerization that produces industrially important products
(dimethyl-7-oxabicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid) was synthesized by polymerization of 7-oxabicyclo[2.2.1]hept-5-ene-2,3- dicarboxylic acid, dimethyl ester, which was prepared by Fischer esterification of exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride
During each step of the synthesis in order confirm the structure of the monomer, the compound 2 and polymers 3 were characterized by FT-IR and gel permeation chromatograph (GPC)

Summary

Introduction

Ring-opening metathesis polymerization (ROMP) is a type of cycloolefin polymerization that produces industrially important products. ROMP of 7-oxanorbornene derivatives is a method to synthesize high molecular weight polymers using commercially available ruthenium catalyst (e.g. Grubbs catalyst generation II). (dimethyl-7-oxabicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid) was synthesized by polymerization of 7-oxabicyclo[2.2.1]hept-5-ene-2,3- dicarboxylic acid, dimethyl ester, which was prepared by Fischer esterification of exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride. Diels Alder reaction of furan and maleic anhydride was carried out [5-9].

Results

Conclusion