Review of glycol ether and glycol ether ester solvents used in the coating industry
Abstract:
Ethylene oxide-based glycol ether and glycol ether ester solvents have been used in the coatings industry for the past fifty years. Because of their excellent performance properties (evaporation rate, blush resistance, flow-out and leveling properties, solubility for coating resins, solvent activity, mild odor, good coupling ability, good solvent release) a complete line of ethylene oxide-based solvents of various molecular weights has been developed. These glycol ether and glycol ether ester solvents have better solvent activity for coating resin than ester or ketone solvents in their evaporation rate range. The gloss, flow and leveling, and general performance properties of many coating systems are dependent on the use of these products in the coating formula. Because of the concern about the toxicity of certain ethylene oxide-based solvents, other products are being evaluated as replacements in coating formulas.
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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 groups, ethers can be classified into two...
Physical Properties of Ethers
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...
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.
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis


