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Encyclopedia > Dioxane
1,4-Dioxane
Chemical structure of dioxane
Chemical name 1,4-Dioxane
Other names [1,4]Dioxane
p-dioxane
Chemical formula C4H8O2
Molecular mass 88.11 g/mol
Melting point 11.8°C
Boiling point 101.1°C
Density 1.033 g/cm3
CAS number [123-91-1]
EINECS number 204-661-8
SMILES C1OCCOC1
Thermodynamic data
Standard enthalpy
of formation ΔfH°liquid		 -354 kJ/mol
Standard enthalpy
of combustion ΔcH°liquid		 -2363 kJ/mol
Standard molar entropy
S°liquid		 196.6 J.K–1.mol–1
Safety data
EU classification Flammable
Carc. Cat. 3
Irritant
R-phrases R11, R19, R36/37,
R40, R66
S-phrases S2, S9, S16,
S36/37, S46
Disclaimer and references

1,4-Dioxane, often just called dioxane, is a clear, colorless organic compound which is a liquid at room temperature and pressure. Its chemical formula and structure are given in the table at right. It is commonly used as an aprotic solvent. 1,4-Dioxane has a weak smell similar to that of diethyl ether. There are also two other similar compounds called 1,2-dioxane and 1,3-dioxane. See the picture below for comparison of the three dioxane structures. Of the three dioxanes, 1,4-dioxane is the one most commonly used as a solvent. Chemical structure of Dioxane selfmade by cacycle File links The following pages link to this file: Ether Dioxane Categories: GFDL images ... IUPAC nomenclature is a systematic way of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change state from a liquid to a gas throughout the bulk of the liquid. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII alpha-numeric strings. ... The standard enthalpy of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of that substance from its component elements, at their standard states (the most stable form of the element at 25 degrees Celsius and 100 kilopascals). ... The enthalpy change that takes place when one mole of a substance is completely burned in oxygen while it is in the standard state. ... In chemistry, the standard molar entropy is the entropy content of one mole of substance, under conditions of standard temperature and pressure. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ... For other uses see fire (disambiguation). ... In pathology, a carcinogen is any substance or agent that promotes cancer. ... The word irritant may refer to: Something that causes irritation, often a chemical substance. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with exception of carbides, carbonates and carbon oxides. ... A liquid will assume the shape of its container. ... Temperature is the physical property of a system which underlies the common notions of hot and cold; the material with the higher temperature is said to be hotter. ... Pressure is the application of force to a surface, and the concentration of that force in a given area. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Chemical structure is the arrangement of atoms within a molecule, usually linked by covalent bonds. ... In chemistry any solvent that carries hydrogen attached to oxygen as in a hydroxyl group or nitrogen as in a amine group is called a protic solvent. ... The term smell may refer to one of the following articles: Olfaction - The sense of smell, that is, the ability to perceive odors Odor - the object being perceived by the sense of olfaction See also Wiktionary:Smell This is a disambiguation page — a navigational aid which lists other pages that... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a typical smell. ...


1,4-dioxane is classified as an ether with two ether functional groups in its molecule, namely its two oxygen atoms. It is more polar than diethyl ether, which also has four carbons, but only one ether functional group. Diethyl ether is rather insoluble in water, but 1,4-dioxane is miscible with water and is hygroscopic. Its higher polarity and slightly higher molecular mass also gives it a substantially higher boiling point than diethyl ether. Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... In ecology functional groups are collections of organisms based on morphological, physiological, behavioral, biochemical, or environmental responses or on trophic criteria. ... A molecule is the smallest particle of a pure chemical substance that still retains its chemical composition and properties. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... Properties For alternative meanings see atom (disambiguation). ... ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a typical smell. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... The chemistry term miscible refers to the property of various liquids that allows them to be mixed together. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... A hygroscopic or hydroscopic substance is a substance that absorbs water readily from its surroundings. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The boiling point of a substance is the temperature at which it can change state from a liquid to a gas throughout the bulk of the liquid. ...


The name dioxane should not be confused with dioxin, which is a different compound but is also a diether (two ether functional groups). Dioxins form a family of toxic chlorinated organic compounds that bioaccumulate in humans and wildlife due to their fat solubility. ...


Caution

  • All of the dioxanes are flammable liquids, similar to many other organic solvents.
  • Upon standing over time, dioxanes combine with oxygen from the air to form explosive peroxides, similar to many other ethers. Distillation of dioxanes concentrates these peroxides increasing the danger. Appropriate precautions should be taken.
Isomers of Dioxane Small blue numbers show numbering of atoms in rings.
Isomers of Dioxane

Small blue numbers show numbering of atoms in rings.

For other uses see fire (disambiguation). ... This article is concerned solely with chemical explosives. ... Strathisla whisky distillery in Keith, Scotland Distillation is a means of separating liquids through differences in their boiling points. ... IARC could mean: International Agency for Research on Cancer is part of the World Health Organization. ... Substances, mixtures and exposure circumstances in this list have been classified by the IARC as Group 2B: The agent (mixture) is possibly carcinogenic to humans. ... Image File history File links Chemical Structures of Dioxane Isomers H Padleckas created this image file on May 28-29, 2005 especially for use in the article Dioxane in Wikipedia. ...

See also

Ether is the general name for a class of chemical compounds which contain an ether group — an oxygen atom connected to two (substituted) alkyl groups. ... Crown ethers are heterocyclic chemical compounds that, in their simplest form, are cyclic oligomers of dioxane. ...

External links

  • Safety (MSDS) data for 1,4-dioxane
  • Hazard Database
  • IARC Monograph on the carcinogenicity of 1,4-dioxane
  • Safety (MSDS) data for 1,3-dioxane
  • Index by Molecular Formula including 1,2- , 1,3- , and 1,4-dioxanes

  Results from FactBites:
 
Dioxane (4143 words)
Dioxane is a clear, colorless, flammable liquid with a mild, pleasant, ether-like odor.
Dioxane is carcinogenic in rats and guinea pigs by oral administration, producing malignant tumors of the nasal cavity and liver in rats of both sexes, and tumors of the liver and gall bladder in male guinea pigs [Hathaway et al.
Prolonged exposure to dioxane is toxic to the liver and kidney.
Dioxane - Wikipedia, the free encyclopedia (293 words)
Of the three dioxanes, 1,4-dioxane is the one most commonly used as a solvent.
The name dioxane should not be confused with dioxin, which is a different compound but is also a diether (two ether functional groups).
Dioxane is classified by the IARC as a Group 2B carcinogen : possibly carcinogenic to humans.
  More results at FactBites »


 

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