1,4-Dioxane

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Contents

1,4-Dioxane
Chemical structure of dioxane 1-4-Dioxane.svg
Chemical structure of dioxane
1,4-dioxane 1,4-Dioxane-3D-balls.png
1,4-dioxane
1,4-dioxane.png
Names
Preferred IUPAC name
1,4-Dioxane
Systematic IUPAC name
1,4-Dioxacyclohexane
Other names
[1,4]Dioxane
p-Dioxane
[6]-crown-2
Diethylene dioxide
Diethylene ether
Dioxane solvent
Identifiers
3D model (JSmol)
102551
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.239 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-661-8
KEGG
PubChem CID
RTECS number
  • JG8225000
UNII
UN number 1165
  • InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2 Yes check.svgY
    Key: RYHBNJHYFVUHQT-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
    Key: RYHBNJHYFVUHQT-UHFFFAOYAN
  • O1CCOCC1
Properties
C4H8O2
Molar mass 88.106 g·mol−1
AppearanceColorless liquid [1]
Odor Mild, diethyl ether-like [1]
Density 1.033 g/mL
Melting point 11.8 °C (53.2 °F; 284.9 K)
Boiling point 101.1 °C (214.0 °F; 374.2 K)
Miscible
Vapor pressure 29 mmHg (20 °C) [1]
−52.16·10−6 cm3/mol
Thermochemistry
Std molar
entropy (S⦵298)
196.6 J/K·mol
−354 kJ/mol
−2363 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Suspected human carcinogen [1]
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H225, H302, H305, H315, H319, H332, H336, H351, H370, H372, H373
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
3
1
Flash point 12 °C (54 °F; 285 K)
180 °C (356 °F; 453 K)
Explosive limits 2.0–22% [1]
Lethal dose or concentration (LD, LC):
  • 5 g/kg (mouse, oral)
  • 4 g/kg (rat, oral)
  • 3 g/kg (guinea pig, oral)
  • 7.6 g/kg (rabbit, dermal)
  • 10,109 ppm (mouse, 2 hr)
  • 12,568 ppm (rat, 2 hr) [2]
1000–3000 ppm (guinea pig, 3 hr)

12,022 ppm (cat, 7 hr)
2085 ppm (mouse, 8 hr) [2]

NIOSH (US health exposure limits):
PEL (Permissible)
TWA 100 ppm (360 mg/m3) [skin] [1]
REL (Recommended)
Ca C 1 ppm (3.6 mg/m3) [30-minute] [1]
IDLH (Immediate danger)
Ca [500 ppm] [1]
Related compounds
Related compounds
 Oxane
Trioxane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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, not readily oxidized by common oxidants.

Dioxane is used as a solvent for a variety of practical applications as well as in the laboratory, and also as a stabilizer for the transport of chlorinated hydrocarbons in aluminium containers. [3]

History and synthesis

The compound was discovered by Portuguese professor Agostinho Vicente Lourenço in 1860 by a reaction of diethylene glycol with 1,2-dibromoethane. [4] He initially designated it ether of glycol and correctly identified its empirical formula, but measured its boiling point at about 95°C. [5] Three year later C. A. Wurtz obtained it by another method, called it dioxyethylene and studied some of its chemical properties. [6]

Dioxane is industrially produced since the 1920s [7] [8] 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. [9]

In 1985, the global production capacity for dioxane was between 11,000 and 14,000 tons. [10] In 1990, the total U.S. production volume of dioxane was between 5,250 and 9,150 tons. [11]

Structure

The three isomers of dioxane Dioxane isomers named.PNG
The three isomers of dioxane

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. [12] With only two ethyleneoxyl units, dioxane is one of the smallest crown ethers.

Uses

Trichloroethane transport

In the 1980s, most of the dioxane produced was used as a stabilizer for 1,1,1-trichloroethane for storage and transport in aluminium containers. Normally aluminium is protected by a passivating oxide layer, but when these layers are disturbed, the metallic aluminium reacts with trichloroethane to give aluminium trichloride, which in turn catalyses the dehydrohalogenation of the remaining trichloroethane to vinylidene chloride and hydrogen chloride. Dioxane "poisons" this catalysis reaction by forming an adduct with aluminium trichloride. [10]

As a solvent

Binary phase diagram for the system 1,4-dioxane/water Binary phase diagram dioxane-water.svg
Binary phase diagram for the system 1,4-dioxane/water

Dioxane is used in a variety of applications as a versatile aprotic solvent (usually considered non-polar [13] , although some sources state otherwise [14] ), e.g. for inks, adhesives, and cellulose esters. It is substituted for tetrahydrofuran (THF) in some processes, because of its lower toxicity and higher boiling point (101 °C, versus 66 °C for THF). [15]

While diethyl ether is rather insoluble in water, dioxane is miscible and in fact is hygroscopic. At standard pressure, the mixture of water and dioxane in the ratio 17.9:82.1 by mass is a positive azeotrope that boils at 87.6 °C. [16]

The oxygen atoms are weakly Lewis-basic. It forms adducts with a variety of Lewis acids. It is classified as a hard base and its base parameters in the ECW model are EB = 1.86 and CB = 1.29.

Dioxane produces insoluble coordination polymers by linking metal centers. [17] In this way, it is used to drive the Schlenk equilibrium, allowing the synthesis of dialkyl magnesium compounds. [10] Dimethylmagnesium is prepared in this manner: [18] [19]

2 CH3MgBr + (C2H4O)2 → MgBr2(C2H4O)2 + (CH3)2Mg

Toxicology

Safety

Dioxane has an LD50 of 5170 mg/kg in rats. [10] It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. [20] In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number of deaths from cancer was not significantly different from the expected number. [21] Dioxane is classified by the National Toxicology Program as "reasonably anticipated to be a human carcinogen". [22] It is also classified by the IARC as a Group 2B carcinogen: possibly carcinogenic to humans because it is a known carcinogen in other animals. [23] The United States Environmental Protection Agency classifies dioxane as a probable human carcinogen (having observed an increased incidence of cancer in controlled animal studies, but not in epidemiological studies of workers using the compound), and a known irritant (with a no-observed-adverse-effects level of 400 milligrams per cubic meter) at concentrations significantly higher than those found in commercial products. [24] Studies with rats suggest that the greatest health risk may be associated with inhalation. [25] [26] [27] The State of New York has adopted a first-in-the-nation drinking water standard for 1,4-Dioxane and set the maximum contaminant level of 1 part per billion. [28]

Explosion hazard

Like some other ethers, dioxane combines with atmospheric oxygen upon prolonged exposure to air to form potentially explosive peroxides. Distillation of these mixtures is dangerous. Storage over metallic sodium could limit the risk of peroxide accumulation.

Environment

It biodegrades through a number of pathways. [29] [30]

Dioxane has affected groundwater supplies in several areas. Dioxane at the level of 1 μg/L (~1 ppb) has been detected in many locations in the US. [11] In the U.S. state of New Hampshire, it had been found at 67 sites in 2010, ranging in concentration from 2 ppb to over 11,000 ppb. Thirty of these sites are solid waste landfills, most of which have been closed for years. In 2019, the Southern Environmental Law Center successfully sued Greensboro, North Carolina's Wastewater treatment after 1,4-Dioxane was found at 20 times above EPA safe levels in the Haw River. [31]

Cosmetics

As a byproduct of the ethoxylation process, a route to some ingredients found in cleansing and moisturizing products, traces of dioxane can be found in cosmetics and personal care products such as deodorants, perfumes, shampoos, toothpastes,, and mouthwashes. [32] [33] The ethoxylation process makes the cleansing agents, such as sodium laureth sulfate and ammonium laureth sulfate, less abrasive and offers enhanced foaming characteristics. 1,4-Dioxane is found in small amounts in some cosmetics, a yet unregulated substance used in cosmetics in both China and the U.S. [34] Research has found the chemical in ethoxylated raw ingredients and in off-the-shelf cosmetic products. The Environmental Working Group (EWG) found that 97% of hair relaxers, 57% of baby soaps and 22 percent of all products in Skin Deep, their database for cosmetic products, are contaminated with 1,4-dioxane. [35]

Since 1979 the U.S. Food and Drug Administration (FDA) have conducted tests on cosmetic raw materials and finished products for the levels of 1,4-dioxane. [36] 1,4-Dioxane was present in ethoxylated raw ingredients at levels up to 1410 ppm (~0.14%wt), and at levels up to 279 ppm (~0.03%wt) in off the shelf cosmetic products. [36] Levels of 1,4-dioxane exceeding 85 ppm (~0.01%wt) in children's shampoos indicate that close monitoring of raw materials and finished products is warranted. [36] While the FDA encourages manufacturers to remove 1,4-dioxane, it is not required by federal law. [37]

On 9 December 2019, New York passed a bill to ban the sale of cosmetics with more than 10 ppm of 1,4-dioxane as of the end of 2022. The law will also prevent the sale of household cleaning and personal care products containing more than 2 ppm of 1,4-dioxane at the end of 2022. [38]

See also

Related Research Articles

Sodium laureth sulfate (SLES), an accepted contraction of sodium lauryl ether sulfate, also called sodium alkylethersulfate, is an anionic detergent and surfactant found in many personal care products and for industrial uses. SLES is an inexpensive and very effective foaming agent. SLES, sodium lauryl sulfate (SLS), ammonium lauryl sulfate (ALS), and sodium pareth sulfate are surfactants that are used in many cosmetic products for their cleaning and emulsifying properties. It is derived from palm kernel oil or coconut oil. In herbicides, it is used as a surfactant to improve absorption of the herbicidal chemicals and reduces time the product takes to be rainfast, when enough of the herbicidal agent will be absorbed.

<span class="mw-page-title-main">Hexane</span> Chemical compound

Hexane or n-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C6H14.

<span class="mw-page-title-main">Propylene glycol</span> Chemical compound

Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classified as a diol. An aliphatic diol may also be called a glycol. It is miscible with a broad range of solvents, including water, acetone, and chloroform. In general, glycols are non-irritating and have very low volatility.

<span class="mw-page-title-main">Tetrachloroethylene</span> Chemical compound in very wide use

Tetrachloroethylene, also known as perchloroethylene or under the systematic name tetrachloroethene, and abbreviations such as perc, and PCE, is a chlorocarbon with the formula Cl2C=CCl2. It is a non-flammable, stable, colorless and heavy liquid widely used for dry cleaning of fabrics. It also has its uses as an effective automotive brake cleaner. It has a mildly sweet, sharp odor, detectable by most people at a concentration of 50 ppm.

Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It is a recognized ozone-depleting chemical. According to the IPCC Fifth Assessment Report, it has a global warming potential of 2. The compound was used extensively as a pesticide until being phased out by most countries in the early 2000s. From a chemistry perspective, it is one of the halomethanes.

<span class="mw-page-title-main">Dichloromethane</span> Chemical compound

Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.

<span class="mw-page-title-main">1,1,1-Trichloroethane</span> Solvent, now banned for ozone depletion

The organic compound 1,1,1-trichloroethane, also known as methyl chloroform and chlorothene, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. A colourless and sweet-smelling liquid, it was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and as such use has declined since 1996. Trichloroethane should not be confused with the similar-sounding trichloroethene which is also commonly used as a solvent.

<span class="mw-page-title-main">Trichloroethylene</span> C2HCl3, widely used industrial solvent

Trichloroethylene (TCE) is a halocarbon with the formula C2HCl3, commonly used as an industrial metal degreasing solvent. It is a clear, colourless, non-flammable, volatile liquid with a chloroform-like pleasant mild smell and sweet taste. Its IUPAC name is trichloroethene. Trichloroethylene has been sold under a variety of trade names. Industrial abbreviations include TCE, trichlor, Trike, Tricky and tri. Under the trade names Trimar and Trilene, it was used as a volatile anesthetic and as an inhaled obstetrical analgesic. It should not be confused with the similar 1,1,1-trichloroethane, which was commonly known as chlorothene.

<span class="mw-page-title-main">Ethylene oxide</span> Cyclic compound (C2H4O)

Ethylene oxide is an organic compound with the formula C2H4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of a silver catalyst.

<span class="mw-page-title-main">Bromoform</span> Chemical compound

Bromoform is an organic compound with the chemical formula CHBr3. It is a colorless liquid at room temperature, with a high refractive index and a very high density. Its sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, chloroform, and iodoform. It is a brominated organic solvent. Currently its main use is as a laboratory reagent. It is very slightly soluble in water and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone and oils.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<span class="mw-page-title-main">2-Butoxyethanol</span> Chemical compound

2-Butoxyethanol is an organic compound with the chemical formula BuOC2H4OH. This colorless liquid has a sweet, ether-like odor, as it derives from the family of glycol ethers, and is a butyl ether of ethylene glycol. As a relatively nonvolatile, inexpensive solvent, it is used in many domestic and industrial products because of its properties as a surfactant. It is a known respiratory irritant and can be acutely toxic, but animal studies did not find it to be mutagenic, and no studies suggest it is a human carcinogen. A study of 13 classroom air contaminants conducted in Portugal reported a statistically significant association with increased rates of nasal obstruction and a positive association below the level of statistical significance with a higher risk of obese asthma and increased body mass index.

1,1,2-Trichloroethane, vinyl trichloride or 1,1,2-TCA, is an organochloride solvent with the molecular formula C2H3Cl3 and the structural formula CH2Cl—CHCl2. It is a colourless, sweet-smelling liquid that does not dissolve in water, but is soluble in most organic solvents. It is an isomer of 1,1,1-trichloroethane, and a byproduct of its manufacture.

<span class="mw-page-title-main">Glycidol</span> Chemical compound

Glycidol is an organic compound with the formula HOCH2CHOCH2. The molecule contains both epoxide and alcohol functional groups. Being simple to make and bifunctional, it has a variety of industrial uses. The compound is a colorless, slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<span class="mw-page-title-main">1,1,2,2-Tetrachloroethane</span> Chemical compound

1,1,2,2-tetrachloroethane (TeCA), also known by the brand names Bonoform, Cellon and Westron, is an organic compound. It is colorless liquid and has a sweet odor. It is used as an industrial solvent and as a separation agent. TeCA is toxic and it can be inhaled, consumed or absorbed through the skin. After exposure, nausea, dizziness or even liver damage may occur.

<span class="mw-page-title-main">1-Bromopropane</span> Chemical compound

1-Bromopropane (n-propylbromide or nPB) is a bromoalkane with the chemical formula CH3CH2CH2Br. It is a colorless liquid that is used as a solvent. It has a characteristic hydrocarbon odor. Its industrial applications increased dramatically in the 21st century due to the phasing out of chloro­fluoro­carbons and chloro­alkanes such as 1,1,1-trichloroethane under the Montreal Protocol.

Methacrylonitrile, MeAN in short, is a chemical compound that is an unsaturated aliphatic nitrile, widely used in the preparation of homopolymers, copolymers, elastomers, and plastics and as a chemical intermediate in the preparation of acids, amides, amines, esters, and other nitriles. MeAN is also used as a replacement for acrylonitrile in the manufacture of an acrylonitrile/butadiene/styrene-like polymer. It is a clear and colorless liquid, that has a bitter almond smell.

<span class="mw-page-title-main">Dichloroacetylene</span> Chemical compound

Dichloroacetylene (DCA) is an organochlorine compound with the formula C2Cl2. It is a colorless, explosive liquid that has a sweet and "disagreeable" odor.

References

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  3. ↑ Wisconsin Department of Health Services (2013) 1,4-Dioxane Fact Sheet Archived 16 October 2020 at the Wayback Machine . Publication 00514. Accessed 2016-11-12.
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  32. ↑ Tenth Report on Carcinogens Archived 1 November 2004 at the Wayback Machine . U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program, December 2002.
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  34. ↑ "Watchdog issues inspection results on Johnson & Johnson". China Daily. Xinhua. 21 March 2009. Retrieved 14 May 2010.
  35. ↑ "The Dangers of 1,4-Dioxane and How to Avoid It". Aspen Clean. Aspen Clean. 11 February 2020. Retrieved 17 December 2020.
  36. 1 2 3 Black, RE; Hurley, FJ; Havery, DC (2001). "Occurrence of 1,4-dioxane in cosmetic raw materials and finished cosmetic products". Journal of AOAC International. 84 (3): 666–70. doi: 10.1093/jaoac/84.3.666 . PMID   11417628.
  37. ↑ FDA/CFSAN--Cosmetics Handbook Part 3: Cosmetic Product-Related Regulatory Requirements and Health Hazard Issues. Prohibited Ingredients and other Hazardous Substances: 9. Dioxane Web.archive.org
  38. ↑ "New York restricts 1,4-dioxane in cleaning and personal care products". Cen.acs.org. Retrieved 13 November 2021.
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