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Highly selective synthesis of mono-ethylene glycol phenyl ethers via hydroxyalkoxylation of phenols by cyclic carbonates using large pore zeolites

Paper ID Volume ID Publish Year Pages File Format Full-Text
51919 46858 2008 7 PDF Available
Title
Highly selective synthesis of mono-ethylene glycol phenyl ethers via hydroxyalkoxylation of phenols by cyclic carbonates using large pore zeolites
Abstract

Hydroxyalkoxylation of phenols by cyclic carbonates catalyzed by alkali loaded large pore zeolites has been reported. The study shows that KL type zeolite was recyclable and selective in producing mono-ethylene glycol phenyl ethers in ∼98.5% yield. Various substituted simple phenols were converted into mono-ethylene glycol ether of phenols with over 90% yields, except 3-bromo and 2-methyl phenols. Mono hydroxyl phenols such as hydroquinone, biphenol and BPA (2,2-bis(4-hydroxyphenyl)propane) also produce corresponding mono- and di-ethylene glycol ethers. The ratio of ethylene carbonate to phenol was found to be critical for selective formation of mono-ethylene glycol phenyl ether of phenols. A ratio of two results in formation of appreciable amount of diether derivative viz., 2-(2-phenoxyethoxy) ethanol. Compared to ethylene carbonate, a lower reactivity of 1,2-propane carbonate was found for hydroxyalkoxylation of phenol. It was found that ring opening at less hindered methylene carbon of 1,2-propylene carbonate prevailed giving rise to selective formation of β-hydroxy phenyl ethers. The reactivity of ethylene carbonate towards O-alkylation versus transesterification of phenol has been explained on the basis of HSAB concept. Finally, it has been shown that yield of mono-ethylene glycol phenyl ether is controlled both by basicity and channel architecture of zeolite structure. KL zeolite was found to be the most effective zeolite because of it’s intermediate basicity and one dimensional channel architect.

Keywords
Hydroxyalkoxylation; Phenol; Cyclic carbonate; Ethylene glycol phenyl ether
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Highly selective synthesis of mono-ethylene glycol phenyl ethers via hydroxyalkoxylation of phenols by cyclic carbonates using large pore zeolites
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 9, Issue 7, 1 April 2008, Pages 1649–1655
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us