Synthesis of potential bisphenol A substitutes by isomerising metathesis of renewable raw materials

Isomerising metathesis is introduced as a sustainable method to produce dihydroxystilbene derivatives from eugenol, a clove oil ingredient, and cardanol from cashew nut shell liquid. Hydrogenation of the dihydroxystilbenes provided their di(hydroxyphenyl)ethane analogues. Initial studies to convert...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2017, Vol.19 (13), p.3051-3060
Main Authors: Trita, A S, Over, L C, Pollini, J, Baader, S, Riegsinger, S, Meier, MAR, Goosen, L J
Format: Article
Language:English
Subjects:
Anacardium
Bisphenol A
Decomposition reactions
Derivatives
Eugenia
Liquids
Metathesis
Monomers
Raw materials
Sustainability
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Summary:Isomerising metathesis is introduced as a sustainable method to produce dihydroxystilbene derivatives from eugenol, a clove oil ingredient, and cardanol from cashew nut shell liquid. Hydrogenation of the dihydroxystilbenes provided their di(hydroxyphenyl)ethane analogues. Initial studies to convert these monomers into polycarbonates and thiol-ene polymers support their potential to replace the petrol-derived bisphenol A (BPA). The estrogenic activity of the monomers derived from cardanol was found to be in the same range as that of BPA, a known endocrine disruptor. In contrast, eugenol-derived materials were found to be non-estrogenic, opening up new perspectives for bio-based food packaging materials.
ISSN:1463-9262
1463-9270
DOI:10.1039/c7gc00553a