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1,4-Dioxane AI simulator
(@1,4-Dioxane_simulator)
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1,4-Dioxane AI simulator
(@1,4-Dioxane_simulator)
1,4-Dioxane
1,4-Dioxane (/daɪˈɒkseɪn/) is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers (1,2- and 1,3-) are rarely encountered.
1,4-Dioxane is miscible in water, essentially nonvolatile when dissolved in water, not well adsorbed by activated carbon, and not readily oxidized by common oxidants.
Dioxane is used as a solvent in manufacturing applications, and as a stabilizer for the transport of chlorinated hydrocarbons in aluminium containers. It is a highly flammable substance that produces toxic vapors when heated.
Although it is a trace material in commonly used products, such as cosmetics, dioxane is considered a hazardous contaminant and potential carcinogen in many countries, requiring government monitoring of amounts used in manufacturing and its presence in air, drinking water, and ecosystems.
The compound was discovered by Portuguese professor Agostinho Vicente Lourenço in 1860 by a reaction of diethylene glycol with 1,2-dibromoethane. He initially designated it ether of glycol and correctly identified its empirical formula, but measured its boiling point at about 95°C. Three years later C. A. Wurtz obtained it by another method, called it dioxyethylene and studied some of its chemical properties.
Dioxane is industrially produced since the 1920s by the acid-catalysed dehydration of diethylene glycol, which in turn is obtained from the hydrolysis of ethylene oxide. This method was developed by Alexey Favorsky in 1906, who also determined the structure of the compound.
In 1985, the global production capacity for dioxane was between 11,000 and 14,000 tons. In 1990, the total U.S. production volume of dioxane was between 5,250 and 9,150 tons.
Three isomers of dioxane exist, but only the 1,3- and 1,4- isomers are significant. The 1,4-dioxane molecule is conformationally flexible: the centrosymmetric chair and the boat conformations easily interconvert such that the H NMR spectrum shows only one signal. For this reason, it is sometimes used as an internal standard for nuclear magnetic resonance spectroscopy in deuterium oxide. With only two ethyleneoxyl units, dioxane is one of the smallest crown ethers.
1,4-Dioxane
1,4-Dioxane (/daɪˈɒkseɪn/) is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers (1,2- and 1,3-) are rarely encountered.
1,4-Dioxane is miscible in water, essentially nonvolatile when dissolved in water, not well adsorbed by activated carbon, and not readily oxidized by common oxidants.
Dioxane is used as a solvent in manufacturing applications, and as a stabilizer for the transport of chlorinated hydrocarbons in aluminium containers. It is a highly flammable substance that produces toxic vapors when heated.
Although it is a trace material in commonly used products, such as cosmetics, dioxane is considered a hazardous contaminant and potential carcinogen in many countries, requiring government monitoring of amounts used in manufacturing and its presence in air, drinking water, and ecosystems.
The compound was discovered by Portuguese professor Agostinho Vicente Lourenço in 1860 by a reaction of diethylene glycol with 1,2-dibromoethane. He initially designated it ether of glycol and correctly identified its empirical formula, but measured its boiling point at about 95°C. Three years later C. A. Wurtz obtained it by another method, called it dioxyethylene and studied some of its chemical properties.
Dioxane is industrially produced since the 1920s by the acid-catalysed dehydration of diethylene glycol, which in turn is obtained from the hydrolysis of ethylene oxide. This method was developed by Alexey Favorsky in 1906, who also determined the structure of the compound.
In 1985, the global production capacity for dioxane was between 11,000 and 14,000 tons. In 1990, the total U.S. production volume of dioxane was between 5,250 and 9,150 tons.
Three isomers of dioxane exist, but only the 1,3- and 1,4- isomers are significant. The 1,4-dioxane molecule is conformationally flexible: the centrosymmetric chair and the boat conformations easily interconvert such that the H NMR spectrum shows only one signal. For this reason, it is sometimes used as an internal standard for nuclear magnetic resonance spectroscopy in deuterium oxide. With only two ethyleneoxyl units, dioxane is one of the smallest crown ethers.
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