Green synthesis of renewable dimethyl terephthalate-like monomer from eugenol

Dimethyl terephthalate, a diester monomer derived from petroleum-based resources, plays important role in the production of polyester such as polyethylene terephthalate (PET), resins for polyester, fibres, and films as well as engineering polymers. High demand on PET together with environmental co...

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Main Authors: Firdaus, Maulidan, Triana Kusumaningsih, Wibowo, Atmanto Heru, Carissa Hertiningtyas
Format: Article
Language:English
Published: Penerbit Universiti Kebangsaan Malaysia 2020
Online Access:http://journalarticle.ukm.my/16001/1/10.pdf
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author Firdaus, Maulidan
Triana Kusumaningsih,
Wibowo, Atmanto Heru
Carissa Hertiningtyas,
author_facet Firdaus, Maulidan
Triana Kusumaningsih,
Wibowo, Atmanto Heru
Carissa Hertiningtyas,
author_sort Firdaus, Maulidan
collection UKM
description Dimethyl terephthalate, a diester monomer derived from petroleum-based resources, plays important role in the production of polyester such as polyethylene terephthalate (PET), resins for polyester, fibres, and films as well as engineering polymers. High demand on PET together with environmental concerns require to find alternative for renewable monomers urgently whenever or wherever to substitute the exhausting crude oil-based monomers. A simple and highly efficient method to prepare PET analogue monomer, methyl 2-[2-methoxy-4-[3-(2-methoxy-2-oxoethyl)] thiopropyl]phenoxy acetate (4), from renewable eugenol is described. The key step involves successive Williamson etherification, esterification, to be followed by thiol-ene reaction. Remarkably, it turned out that the thiol-ene reaction has proven to be effective in the introduction of the ester group to the olefinic substrate without the use of solvent and initiator leading to diester 4. The technique offered here comprises advantages i.e. excellent yields, mild reaction condition, and easy to perform, thus, provide a sustainable alternative to synthesize diester from eugenol.
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spelling ukm.eprints-160012020-12-17T04:56:12Z http://journalarticle.ukm.my/16001/ Green synthesis of renewable dimethyl terephthalate-like monomer from eugenol Firdaus, Maulidan Triana Kusumaningsih, Wibowo, Atmanto Heru Carissa Hertiningtyas, Dimethyl terephthalate, a diester monomer derived from petroleum-based resources, plays important role in the production of polyester such as polyethylene terephthalate (PET), resins for polyester, fibres, and films as well as engineering polymers. High demand on PET together with environmental concerns require to find alternative for renewable monomers urgently whenever or wherever to substitute the exhausting crude oil-based monomers. A simple and highly efficient method to prepare PET analogue monomer, methyl 2-[2-methoxy-4-[3-(2-methoxy-2-oxoethyl)] thiopropyl]phenoxy acetate (4), from renewable eugenol is described. The key step involves successive Williamson etherification, esterification, to be followed by thiol-ene reaction. Remarkably, it turned out that the thiol-ene reaction has proven to be effective in the introduction of the ester group to the olefinic substrate without the use of solvent and initiator leading to diester 4. The technique offered here comprises advantages i.e. excellent yields, mild reaction condition, and easy to perform, thus, provide a sustainable alternative to synthesize diester from eugenol. Penerbit Universiti Kebangsaan Malaysia 2020-11 Article PeerReviewed application/pdf en http://journalarticle.ukm.my/16001/1/10.pdf Firdaus, Maulidan and Triana Kusumaningsih, and Wibowo, Atmanto Heru and Carissa Hertiningtyas, (2020) Green synthesis of renewable dimethyl terephthalate-like monomer from eugenol. Sains Malaysiana, 49 (11). pp. 2715-2720. ISSN 0126-6039 https://www.ukm.my/jsm/malay_journals/jilid49bil11_2020/KandunganJilid49Bil11_2020.html
spellingShingle Firdaus, Maulidan
Triana Kusumaningsih,
Wibowo, Atmanto Heru
Carissa Hertiningtyas,
Green synthesis of renewable dimethyl terephthalate-like monomer from eugenol
title Green synthesis of renewable dimethyl terephthalate-like monomer from eugenol
title_full Green synthesis of renewable dimethyl terephthalate-like monomer from eugenol
title_fullStr Green synthesis of renewable dimethyl terephthalate-like monomer from eugenol
title_full_unstemmed Green synthesis of renewable dimethyl terephthalate-like monomer from eugenol
title_short Green synthesis of renewable dimethyl terephthalate-like monomer from eugenol
title_sort green synthesis of renewable dimethyl terephthalate like monomer from eugenol
url http://journalarticle.ukm.my/16001/1/10.pdf
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