Synthesis and Ring‐Opening Polymerization of Cyclic Butylene 2, 5‐Furandicarboxylate. Issue 21 (13th October 2015)

• Record Type: Journal Article
• Authors: Pfister, David; Storti, Giuseppe; Tancini, Francesca; Costa, Liborio I.; Morbidelli, Massimo
• Is Part Of: Macromolecular chemistry and physics. Volume 216:Issue 21(2015:Nov.)
• Page Start: 2141
• Page End: 2146
• Publication Date: 2015-10-13
• Subjects: biopolymers -- copolymerization -- cyclopolymerization -- polyesters -- ring‐opening polymerization; Polymers -- Periodicals; Polymerization -- Periodicals; Synthetic products -- Periodicals; Macromolecules -- Periodicals; 547.7
• DOI: 10.1002/macp.201500297
• Languages: English
• ISSNs: 1022-1352

Abstract

Abstract : A new synthetic pathway for the polymerization of furan based polyesters is reported in this work. First, poly(butylene 2, 5‐furandicarboxylate) cyclic oligoesters (COEs) are chemically synthesized by semi‐batch esterification. The structure of the COEs is confirmed by infrared spectroscopy, 1 H, and 13 C‐NMR, while the molecular weight distribution of the COEs is determined by matrix‐assisted laser desorption/ionization time of flight mass spectroscopy. The cyclic oligoesters are then successfully polymerized via ring‐opening polymerization using tetrakis(2‐ethylhexyl)‐titanate as catalyst. Differential scanning calorimetry and 1 H‐NMR analysis unambiguously proves the formation of polymeric species. Both end‐group analysis from 1 H‐NMR spectrum and calculation through Flory–Fox equation give comparable estimates of the number average molecular weight: 5.8 × 10 3 g mol −1 and 7.8 × 10 3 g mol −1, respectively. Abstract : Furanic polyesters, derived from renewable 2, 5‐furandicarboxylic acid, are highly attractive polymers and sustainable substitutes of some performance‐related fossil‐based commodities like polyethylene terephthalate. In this work a new synthetic pathway for the production of furan‐based polyesters is reported. Cyclic oligoesters of 2, 5‐furandicarboxylic acid and butane diol are chemically synthesized by semi‐batch esterification. The cycles are then successfully polymerized via ring‐opening polymerization.