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
Tetroxane
Pentoxane
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.

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]

Synthesis

Dioxane is produced by the acid-catalysed dehydration of diethylene glycol, which in turn is obtained from the hydrolysis of ethylene oxide.

In 1985, the global production capacity for dioxane was between 11,000 and 14,000 tons. [4] In 1990, the total U.S. production volume of dioxane was between 5,250 and 9,150 tons. [5]

Structure

The dioxane molecule is centrosymmetric, meaning that it adopts a chair conformation, typical of relatives of cyclohexane. However, the molecule is conformationally flexible, and the boat conformation is easily adopted, e.g. in the chelation of metal cations. Dioxane resembles a smaller crown ether with only two ethyleneoxyl units.

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. [4]

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, 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). [6]

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. [7]

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 coordination polymers by linking metal centers. [8] In this way, it is used to drive the Schlenk equilibrium, allowing the synthesis of dialkyl magnesium compounds. [4] Dimethylmagnesium is prepared in this manner: [9] [10]

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

Spectroscopy

Dioxane is used as an internal standard for nuclear magnetic resonance spectroscopy in deuterium oxide. [11]

Toxicology

Safety

Dioxane has an LD50 of 5170 mg/kg in rats. [4] It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys. [12] 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. [13] Dioxane is classified by the National Toxicology Program as "reasonably anticipated to be a human carcinogen". [14] 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. [15] 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. [16] Animal studies in rats suggest that the greatest health risk is associated with inhalation of vapors in the pure form. [17] [18] [19] 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. [20]

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

Dioxane tends to concentrate in the water and has little affinity for soil. It is resistant to abiotic degradation in the environment, and was formerly thought to also resist biodegradation. However, more recent studies since the 2000s have found that it can be biodegraded through a number of pathways, suggesting that bioremediation can be used to treat 1,4-dioxane contaminated water. [21] [22]

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. [5] 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. [23]

Cosmetics

As a byproduct of the ethoxylation process, a route to some ingredients found in cleansing and moisturizing products, dioxane can contaminate cosmetics and personal care products such as deodorants, perfumes, shampoos, toothpastes and mouthwashes. [24] [25] 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. [26] 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. [27]

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. [28] 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. [28] 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. [28] While the FDA encourages manufacturers to remove 1,4-dioxane, it is not required by federal law. [29]

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. [30]

See also

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

Related Research Articles

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<span class="mw-page-title-main">Formaldehyde</span> Organic compound (H–CHO); simplest aldehyde

Formaldehyde ( for-MAL-di-hide, fər-) (systematic name methanal) is an organic compound with the chemical formula CH2O and structure H−CHO, more precisely H2C=O. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH2(OH)2. It is the simplest of the aldehydes (R−CHO). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Small amounts also occur naturally.

<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">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, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a mild sweet, sharp odor, detectable by most people at a concentration of 50 ppm.

Chlordane, or chlordan, is an organochlorine compound that was used as a pesticide. It is a white solid. In the United States, chlordane was used for termite-treatment of approximately 30 million homes until it was banned in 1988. Chlordane was banned 10 years earlier for food crops like corn and citrus, and on lawns and domestic gardens.

<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">Vinyl chloride</span> Chemical compound

Vinyl chloride is an organochloride with the formula H2C=CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC). Vinyl chloride monomer is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production. The United States remains the largest vinyl chloride manufacturing region because of its low-production-cost position in chlorine and ethylene raw materials. China is also a large manufacturer and one of the largest consumers of vinyl chloride. Vinyl chloride is a flammable gas that has a sweet odor and is carcinogenic. It can be formed in the environment when soil organisms break down chlorinated solvents. Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies. Vinyl chloride is a common contaminant found near landfills. Before the 1970s, vinyl chloride was used as an aerosol propellant and refrigerant.

<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 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 is commonly known as chlorothene.

<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.

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

Chloroprene (IUPAC name 2-chlorobuta-1,3-diene) is a chemical compound with the molecular formula CH2=CCl−CH=CH2. Chloroprene is a colorless volatile liquid, almost exclusively used as a monomer for the production of the polymer polychloroprene, better known as neoprene, a type of synthetic rubber.

<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.

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

Aldrin is an organochlorine insecticide that was widely used until the 1990s, when it was banned in most countries. Aldrin is a member of the so-called "classic organochlorines" (COC) group of pesticides. COCs enjoyed a very sharp rise in popularity during and after World War II. Other noteworthy examples of COCs include dieldrin and DDT. After research showed that organochlorines can be highly toxic to the ecosystem through bioaccumulation, most were banned from use. Before the ban, it was heavily used as a pesticide to treat seed and soil. Aldrin and related "cyclodiene" pesticides became notorious as persistent organic pollutants.

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">Sodium bisulfite</span> Chemical compound

Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of sodium and bisulfite ions. It appears in form of white or yellowish-white crystals with an odor of sulfur dioxide. Regardless of its ill-defined nature, sodium bisulfite is used in many different industries such as a food additive with E number E222 in the food industry, a reducing agent in the cosmetic industry, and a decomposer of residual hypochlorite used in the bleaching industry.

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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  2. 1 2 "Dioxane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  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.
  4. 1 2 3 4 Surprenant, Kenneth S. (2000). "Dioxane". Dioxane in Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_545. ISBN   978-3527306732.
  5. 1 2 "1, 4-Dioxane Fact Sheet: Support Document" (PDF). OPPT Chemical Fact Sheets. United States Environmental Protection Agency. February 1995. Retrieved 14 May 2010.
  6. ↑ Klaus Weissermel, Hans-Jürgen Arpe (2003) "Industrial Organic Chemistry". John Wiley & Sons, page 158. ISBN   3527305785, 9783527305780.
  7. ↑ Schneider, Charles H.; Lynch, Cecil C. (1943). "The Ternary System: Dioxane—Ethanol—Water". Journal of the American Chemical Society. 65 (6): 1063–1066. doi:10.1021/ja01246a015.
  8. ↑ Fischer, Reinald; Görls, Helmar; Meisinger, Philippe R.; Suxdorf, Regina; Westerhausen, Matthias (2019). "Structure–Solubility Relationship of 1,4-Dioxane Complexes of Di(hydrocarbyl)magnesium". Chemistry – A European Journal. 25 (55): 12830–12841. doi:10.1002/chem.201903120. PMC   7027550 . PMID   31328293.
  9. ↑ Cope, Arthur C. (1935). "The Preparation of Dialkylmagnesium Compounds from Grignard Reagents". Journal of the American Chemical Society. 57 (11): 2238. doi:10.1021/ja01314a059.
  10. ↑ Anteunis, M. (1962). "Studies of the Grignard Reaction. II. Kinetics of the Reaction of Dimethylmagnesium with Benzophenone and of Methylmagnesium Bromide-Magnesium Bromide with Pinacolone". The Journal of Organic Chemistry. 27 (2): 596. doi:10.1021/jo01049a060.
  11. ↑ Shimizu, A.; Ikeguchi, M.; Sugai, S. (1994). "Appropriateness of DSS and TSP as internal references for 1H NMR studies of molten globule proteins in aqueous media". Journal of Biomolecular NMR . 4 (6): 859–62. doi:10.1007/BF00398414. PMID   22911388. S2CID   34800494.
  12. ↑ "International Chemical Safety Card". National Institute for Occupational Safety and Health. Archived from the original on 29 April 2005. Retrieved 6 February 2006.
  13. ↑ Buffler, Patricia A.; Wood, Susan M.; Suarez, Lucina; Kilian, Duane J. (April 1978). "Mortality Follow-up of Workers Exposed to 1,4-Dioxane". Journal of Occupational and Environmental Medicine. 20 (4): 255–259. PMID   641607 . Retrieved 26 March 2016.
  14. ↑ "12th Report on Carcinogens". United States Department of Health and Human Services' National Toxicology Program. Archived from the original on 14 July 2014. Retrieved 11 July 2014.
  15. ↑ IARC Monographs Volume 71 (PDF). International Agency for Research on Cancer. Retrieved 11 July 2014.
  16. ↑ 1,4-Dioxane (1,4-Diethyleneoxide). Hazard Summary. U.S. Environmental Protection Agency. Created in April 1992; Revised in January 2000. Fact Sheet.
  17. ↑ Kano, Hirokazu; Umeda, Yumi; Saito, Misae; Senoh, Hideki; Ohbayashi, Hisao; Aiso, Shigetoshi; Yamazaki, Kazunori; Nagano, Kasuke; Fukushima, Shoji (2008). "Thirteen-week oral toxicity of 1,4-dioxane in rats and mice". The Journal of Toxicological Sciences. 33 (2): 141–53. doi: 10.2131/jts.33.141 . PMID   18544906.
  18. ↑ Kasai, T; Saito, M; Senoh, H; Umeda, Y; Aiso, S; Ohbayashi, H; Nishizawa, T; Nagano, K; Fukushima, S (2008). "Thirteen-week inhalation toxicity of 1,4-dioxane in rats". Inhalation Toxicology. 20 (10): 961–71. Bibcode:2008InhTx..20..961K. doi:10.1080/08958370802105397. PMID   18668411. S2CID   86811931.
  19. ↑ Kasai, T.; Kano, H.; Umeda, Y.; Sasaki, T.; Ikawa, N.; Nishizawa, T.; Nagano, K.; Arito, H.; Nagashima, H.; Fukushima, S. (2009). "Two-year inhalation study of carcinogenicity and chronic toxicity of 1,4-dioxane in male rats". Inhalation Toxicology. 21 (11): 889–97. Bibcode:2009InhTx..21..889K. doi:10.1080/08958370802629610. PMID   19681729. S2CID   45963495.
  20. ↑ "Governor Cuomo Announces First in the Nation Drinking Water Standard for Emerging Contaminant 1,4-Dioxane | Governor Andrew M. Cuomo". Archived from the original on 29 October 2020. Retrieved 30 October 2020.
  21. ↑ Zenker, Matthew J.; Borden, Robert C.; Barlaz, Morton A. (September 2003). "Occurrence and Treatment of 1,4-Dioxane in Aqueous Environments". Environmental Engineering Science. 20 (5): 423–432. doi:10.1089/109287503768335913.
  22. ↑ Zhang, Shu; Gedalanga, Phillip B.; Mahendra, Shaily (December 2017). "Advances in bioremediation of 1,4-dioxane-contaminated waters". Journal of Environmental Management. 204 (Pt 2): 765–774. doi: 10.1016/j.jenvman.2017.05.033 . PMID   28625566.
  23. ↑ "1,4-dioxane in Greensboro | Haw River Assembly". 18 November 2020. Retrieved 13 May 2022.
  24. ↑ 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.
  25. ↑ "Chemical Encyclopedia: 1,4-dioxane". Healthy Child Healthy World. Archived from the original on 29 November 2009. Retrieved 14 December 2009.
  26. ↑ "Watchdog issues inspection results on Johnson & Johnson". China Daily. Xinhua. 21 March 2009. Retrieved 14 May 2010.
  27. ↑ "The Dangers of 1,4-Dioxane and How to Avoid It". Aspen Clean. Aspen Clean. 11 February 2020. Retrieved 17 December 2020.
  28. 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.
  29. ↑ 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
  30. ↑ "New York restricts 1,4-dioxane in cleaning and personal care products". Cen.acs.org. Retrieved 13 November 2021.
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