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A potentially general approach to aliphatic ester-derived PVC plasticizers with suppressed migration as sustainable alternatives to DEHP

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Abstract

The safety of flexible polyvinyl chloride (PVC) materials is now being questioned, partially due to allegations that di-(2-ethylhexyl) phthalate (DEHP), the dominant PVC plasticizer, is an endocrine disruptor and a probable carcinogen. As sustainable alternatives, aliphatic ester-derived plasticizers feature low cytotoxicity, biodegradability, and renewability, but they can only partially replace DEHP in PVC formulations because they have a strong tendency to migrate. Here, using epoxidized fatty acid methyl esters and aliphatic diesters as representatives, we demonstrate that covalently attaching one short ester at each α-position of aliphatic esters via Claisen condensation with judiciously selected dialkyl carbonate significantly suppresses their migration from the PVC matrix. In certain scenarios, the engineered plasticizers even migrate at a rate comparable to, or improved beyond that of DEHP. This approach harnesses the α-proton, a structural feature shared by all aliphatic esters, and dialkyl carbonate, an established “green chemical”, thus providing a potentially general and green route towards DEHP alternatives with unprecedented performance that may contribute to sustainability of the old and oft-maligned PVC industry.

Graphical abstract: A potentially general approach to aliphatic ester-derived PVC plasticizers with suppressed migration as sustainable alternatives to DEHP

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Publication details

The article was received on 01 Sep 2019, accepted on 23 Oct 2019 and first published on 23 Oct 2019


Article type: Paper
DOI: 10.1039/C9GC03077H
Green Chem., 2019, Advance Article

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    A potentially general approach to aliphatic ester-derived PVC plasticizers with suppressed migration as sustainable alternatives to DEHP

    S. Pan, D. Hou, J. Chang, Z. Xu, S. Wang, S. Yan, Q. Zeng, Z. Wang and Y. Chen, Green Chem., 2019, Advance Article , DOI: 10.1039/C9GC03077H

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