Advances in the synthesis of bio-based aromatic polyesters: novel copolymers derived from vanillic acid and ε-caprolactone

Author(s): C. Gioia ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , M. B. Banella ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , P. Marchese ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , M. Vannini ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , M. Colonna ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , A. Celli ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵

Publication date (Electronic): 2016

Journal: Polymer Chemistry

Publisher: Royal Society of Chemistry (RSC)

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Abstract

A new and sustainable pathway for the synthesis of polyesters and copolyesters derived from vanillic acid is reported. The one-pot procedure does not require either solvents or purification steps. New bio-based crystalline copolymers with tunable thermal properties are obtained.

Abstract

A new and sustainable pathway for the synthesis of polyesters and copolyesters derived from vanillic acid is suggested. The poor reactivity of the fenolic –OH group of vanillic acid has been overcome by etherification reactions with biobased ethylene carbonate: the full procedure towards poly(ethylene vanillate) (PEV) avoids solvents and purification steps and uses only bio-based reagents. The PEV thus obtained is an example of bio-based PET mimics, characterized by high thermal transitions and a notable level of crystallinity. However, probably due to its low molecular weight, the material is brittle. In order to solve such problems and to exploit the aromatic structure of PEV to enhance the properties of aliphatic polyesters, new copolymers based on PEV and poly-ε-caprolactone were prepared. The new materials are characterized by an EV crystalline phase and tunable thermal properties according to the composition.

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Conversion of biomass to selected chemical products.

Pierre Gallezot (2012)

This critical review provides a survey illustrated by recent references of different strategies to achieve a sustainable conversion of biomass to bioproducts. Because of the huge number of chemical products that can be potentially manufactured, a selection of starting materials and targeted chemicals has been done. Also, thermochemical conversion processes such as biomass pyrolysis or gasification as well as the synthesis of biofuels were not considered. The synthesis of chemicals by conversion of platform molecules obtained by depolymerisation and fermentation of biopolymers is presently the most widely envisioned approach. Successful catalytic conversion of these building blocks into intermediates, specialties and fine chemicals will be examined. However, the platform molecule value chain is in competition with well-optimised, cost-effective synthesis routes from fossil resources to produce chemicals that have already a market. The literature covering alternative value chains whereby biopolymers are converted in one or few steps to functional materials will be analysed. This approach which does not require the use of isolated, pure chemicals is well adapted to produce high tonnage products, such as paper additives, paints, resins, foams, surfactants, lubricants, and plasticisers. Another objective of the review was to examine critically the green character of conversion processes because using renewables as raw materials does not exempt from abiding by green chemistry principles (368 references).