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Preparation of Biopolymer Aerogels Using Green Solvents
Published on: July 4, 2016
Bypassing Osmotic Shock Dilemma in a Polystyrene Resin Using the Green Solvent Cyclopentyl methyl Ether (CPME): A
Othman Al Musaimi1,2, Ayman El-Faham3,4, Zainab Almarhoon5
1Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa. musamiau@gmail.com.
Abstract:
The "osmotic shock" phenomenon is the main thing that is responsible for morphological structure alteration, which can jeopardize the use of a polymer in a chemical process. This is extremely important in solid-phase peptide synthesis (SPPS), which is the method of choice for the preparation of these important biologically active compounds. Herein, we have used Hildebrand solubility parameters (δ) to investigate the influence of different ethers that are used in the precipitation step of the SPPS using a polystyrene resin. The green cyclopentyl methyl ether (CPME) has shown to be slightly superior to 2-methyltetrahydrofurane, which is also a green ether and clearly better than the hazardous diethyl ether and tert-butyl methyl ether. These results have been corroborated by scanning electron microscope (SEM) analysis and computational studies. All together, these confirm the adequacy of CPME for being the ether of choice to be used in SPPS.
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Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
Structure and Nomenclature of Ethers
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent...

