1,4-Dioxane

1,4-Dioxin Dioxane other uses Dioxane (compounds) May 2020 changed 477206315 1-4-Dioxane.svg skin-invert Chemical structure of dioxane 90px 1,4-Dioxane-3D-balls.png bg-transparent 130px 1,4-dioxane 1,4-dioxane.png 150px 1,4-Dioxane 1,4-Dioxacyclohexane [1,4]Dioxanep-Dioxane[6]-crown-2Diethylene dioxideDiethylene etherDioxane solvent correct chemspider correct EBI 47032 29015 correct kegg C14440 1/C4H8O2/c1-2-6-4-3-5-1/h1-4H2 RYHBNJHYFVUHQT-UHFFFAOYAN correct EBI 453716 correct chemspider 1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2 correct chemspider RYHBNJHYFVUHQT-UHFFFAOYSA-N correct CAS 123-91-1 204-661-8 correct FDA J8A3S10O7S correct drugbank DB03316 31275 JG8225000 1165 102551 O1CCOCC1 4 8 2 11.8 101.1 1.033 g/mL Miscible Colorless liquid Mild, diethyl ether-like 29 mmHg (20 °C) −52.16·10−6 cm3/mol −354 kJ/mol −2363 kJ/mol 196.6 J/K·mol 2 3 1 02 07 08 Danger 225 302 305 315 319 332 336 351 370 372 373 201 202 210 233 240 241 242 243 260 261 264 270 271 280 281 302+352 303+361+353 304+312 304+340 305+351+338 307+311 308+313 312 314 321 332+313 337+313 362 370+378 403+233 403+235 405 501 12 180 TWA 100 ppm (360 mg/m3) [skin]0237 2.0–22% Ca [500 ppm] Ca C 1 ppm (3.6 mg/m3) [30-minute] Suspected human carcinogen 10,109 ppm (mouse, 2 hr) 12,568 ppm (rat, 2 hr)123911 Dioxane 1000–3000 ppm (guinea pig, 3 hr) 12,022 ppm (cat, 7 hr) 2085 ppm (mouse, 8 hr) 5 g/kg (mouse, oral) 4 g/kg (rat, oral) 3 g/kg (guinea pig, oral) 7.6 g/kg (rabbit, dermal) OxaneTrioxane 1,4-Dioxane (d aɪ ˈ ɒ k s eɪ n) 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.Wisconsin Department of Health Services (2013) 1,4-Dioxane Fact Sheet https://web.archive.org/web/20201016235134/https://www.dhs.wisconsin.gov/publications/p0/p00514.pdf 16 October 2020 . Publication 00514. Accessed 2016-11-12. 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.1,4-Dioxane https://pubchem.ncbi.nlm.nih.gov/compound/31275 PubChem, US National Library of Medicine 16 July 2025 13 July 20251,4-Dioxane in Cosmetics: A Manufacturing Byproduct https://www.fda.gov/cosmetics/potential-contaminants-cosmetics/14-dioxane-cosmetics-manufacturing-byproduct US Food and Drug Administration 16 July 2025 3 March 2022Guidelines for Canadian Drinking Water Quality: Guideline Technical Document - 1,4-Dioxane https://www.canada.ca/en/health-canada/services/publications/healthy-living/guidelines-canadian-drinking-water-quality-guideline-1-4-dioxane.html Government of Canada 16 July 2025 26 March 2021 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. https://books.google.com/books?id=5oI5AAAAcAAJ&pg=PA207 Bulletin de la Société Chimique de Paris 1860 Hachette Paris 207 fr He initially designated it ether of glycol and correctly identified its empirical formula, but measured its boiling point at about 95 °C.Lourenco Agostinho Vicente https://books.google.com/books?id=pKdcAAAAcAAJ&pg=PA37 Thèses présentées à la Faculté des Sciences de Paris pour le Doctorat ès Sciences physiques 1862 Paris Paris Academy 37–40 fr Three years later C. A. Wurtz obtained it by another method, called it dioxyethylene and studied some of its chemical properties.https://books.google.com/books?id=g69JAQAAMAAJ&pg=PA323 Annales de chimie et de physique Haller Albin 1863 Masson. 323–326 fr Dioxane is industrially produced since the 1920sSub-committee Great Britain British Intelligence Objectives https://books.google.com/books?id=N7JQAAAAYAAJ&q=Ludwigshafen+dioxan+1920 B.I.O.S. Final Report H.M. Stationery Office enMohr Thomas K. G. https://books.google.com/books?id=wUnLBQAAQBAJ&pg=PA52 Environmental Investigation and Remediation: 1,4-Dioxane and other Solvent Stabilizers 2016-04-19 CRC Press 978-0-203-48937-6 en 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.Быков Георгий Владимирович https://books.google.com/books?id=76RbAAAAIAAJ&q=%D0%B4%D0%B8%D0%BE%D0%BA%D1%81%D0%B0%D0%BD История органической химии: Открытие важнейших органических соединений 1978 Наука ru 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. http://www.epa.gov/chemfact/dioxa-sd.pdf https://web.archive.org/web/20040716155301/http://www.epa.gov/chemfact/dioxa-sd.pdf dead 16 July 2004 United States Environmental Protection Agency OPPT Chemical Fact Sheets February 1995 1, 4-Dioxane Fact Sheet: Support Document 14 May 2010 Structure thumb|upright=1.2|The three isomers of dioxane|left 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.Shimizu A. Ikeguchi M. Sugai S. Appropriateness of DSS and TSP as internal references for 1H NMR studies of molten globule proteins in aqueous media Journal of Biomolecular NMR 4 1994 10.1007/BF00398414 22911388 6 859–62 34800494 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.Surprenant Kenneth S. Dioxane in Ullmann's Encyclopedia of Industrial Chemistry 2000 10.1002/14356007.a08_545 Dioxane 978-3527306732 As a solvent left|thumb|200px|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,2014-05-28 Polar Protic and Aprotic Solvents https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Fundamentals/Intermolecular_Forces/Polar_Protic_and_Aprotic_Solvents 2025-02-03 Chemistry LibreTexts en although some sources state otherwiseCrespo J. G. https://books.google.com/books?id=KwnoCAAAQBAJ&pg=PA94 Membrane Processes in Separation and Purification Böddeker Karl W. 2013-11-11 Springer Science & Business Media 978-94-015-8340-4 en), 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).Klaus Weissermel, Hans-Jürgen Arpe (2003) "Industrial Organic Chemistry". John Wiley & Sons, page 158. 3527305785, 9783527305780. 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. 10.1021/ja01246a015 The Ternary System: Dioxane—Ethanol—Water 1943 Schneider Charles H. Lynch Cecil C. Journal of the American Chemical Society 65 6 1063–1066 1943JAChS..65.1063S 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.10.1002/chem.201903120 Structure–Solubility Relationship of 1,4-Dioxane Complexes of Di(hydrocarbyl)magnesium 2019 Fischer Reinald Görls Helmar Meisinger Philippe R. Suxdorf Regina Westerhausen Matthias Chemistry – A European Journal 25 55 12830–12841 31328293 7027550 2019ChEuJ..2512830F In this way, it is used to drive the Schlenk equilibrium, allowing the synthesis of dialkyl magnesium compounds. Dimethylmagnesium is prepared in this manner:The Preparation of Dialkylmagnesium Compounds from Grignard Reagents Cope Arthur C. Journal of the American Chemical Society 57 2238 1935 10.1021/ja01314a059 11 1935JAChS..57.2238C Anteunis M. 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 27 596 1962 10.1021/jo01049a060 2 2 CH3MgBr + (C2H4O)2 → MgBr2(C2H4O)2 + (CH3)2Mg Toxicology Safety Dioxane vapor is irritating to the eyes and respiratory tract; its contamination of air, food, drinking water, or cosmetics are examples of typical exposure. High levels of 1,4-dioxane in the air can result in injury to the nasal cavity, liver, or kidneys.ToxFAQs for 1,4-Dioxane https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsDetails.aspx?faqid=954&toxid=199 Agency for Toxic Substances and Disease Registry, US Centers for Disease Control and Prevention 16 July 2025 18 June 2015 As a flammable compound, dioxane under high heat or fire may produce irritating, corrosive and toxic vapors causing dizziness or asphyxiation in confined work spaces. Environmental contamination, especially in drinking water, may occur from manufacturing runoff or uncontrolled waste disposal.Final Risk Evaluation for 1,4-Dioxane https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/final-risk-evaluation-14-dioxane US Environmental Protection Agency 16 July 2025 13 November 2024 EPA identified health risks, risks of liver toxicity, adverse effects in the olfactory epithelium, and cancer from inhalation or dermal exposures to 1,4-dioxane, as well as from ingestion of drinking water. Risk from several conditions of use (including manufacturing, import, processing, industrial and commercial uses, and disposal) of 1,4-dioxane, including as a byproduct, significantly contribute to the whole chemical determination of unreasonable risk of injury to health Dioxane is classified by several government agencies as a potential cancer-causing chemical. 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. IARC Monographs Volume 71 International Agency for Research on Cancer https://monographs.iarc.fr/ENG/Monographs/vol71/mono71-25.pdf 11 July 2014 In 2024, the United States Environmental Protection Agency classified dioxane as a probable human carcinogen and an unreasonable risk to human health, which establishes a legal basis for federal regulation under the Toxic Substances Control Act.Bettenhausen Craig Cleaning out a carcinogenic contaminant Chemical & Engineering News 28 January 2025 https://cen.acs.org/business/consumer-products/Cleaning-carcinogenic-contaminant/103/i2 20 October 2025 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.https://www.governor.ny.gov/news/governor-cuomo-announces-first-nation-drinking-water-standard-emerging-contaminant-14-dioxane Governor Cuomo Announces First in the Nation Drinking Water Standard for Emerging Contaminant 1,4-Dioxane Governor Andrew M. Cuomo 30 October 2020 29 October 2020 https://web.archive.org/web/20201029142313/https://www.governor.ny.gov/news/governor-cuomo-announces-first-nation-drinking-water-standard-emerging-contaminant-14-dioxane dead 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.European Chemicals Agency ANNEX 1 in support of the Committee for Risk Assessment (RAC) for evaluation of limit values for 1,4-dioxane at the workplace https://echa.europa.eu/documents/10162/073d44ca-5ad2-8128-fd15-8c74a4bdb126 European Chemicals Agency 13 March 2025 ECHA/RAC/OEL-O-0000007101-89-01/F 9 English 18 March 2022 Environment Dioxane biodegrades through a number of pathways.Zenker Matthew J. Borden Robert C. Barlaz Morton A. Occurrence and Treatment of 1,4-Dioxane in Aqueous Environments Environmental Engineering Science September 2003 20 5 423–432 10.1089/109287503768335913Zhang Shu Gedalanga Phillip B. Mahendra Shaily Advances in bioremediation of 1,4-dioxane-contaminated waters Journal of Environmental Management December 2017 204 Pt 2 765–774 10.1016/j.jenvman.2017.05.033 28625566 free 2017JEnvM.204..765Z 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. In the U.S. state of New Hampshire, it was 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.2020-11-18 1,4-dioxane in Greensboro Haw River Assembly Haw River Assembly Defending the river since 1982 https://hawriver.org/14-dioxane-in-greensboro/ 2022-05-13 en-US Municipalities, industrial water users and superfund sites are successfully removing dioxane from water streams with advanced oxidation process systems.Mandal Suyash Reaction Rate Constants of Hydroxyl Radicals with Micropollutants and Their Significance in Advanced Oxidation Processes Journal of Advanced Oxidation Technologies 2018 21 1 178–195 10.26802/jaots.2017.0075 https://www.researchgate.net/publication/322195659 5 June 2026William DiGuiseppi Claudia Walecka-Hutchinson Jim Hatton 1,4-Dioxane Treatment Technologies Remediation 2016 27 1 71–92 10.1002/rem.21498 2016RemJ...27a..71D https://www.researchgate.net/publication/311659999 5 June 2026 Consumer products 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. Chemical Encyclopedia: 1,4-dioxane Healthy Child Healthy World http://healthychild.org/issues/chemical-pop/1,4-dioxane/ 14 December 2009 https://web.archive.org/web/20091129073643/http://healthychild.org/issues/chemical-pop/1,4-dioxane/ 29 November 2009 The ethoxylation process makes the cleansing agents, such as sodium laureth sulfate and ammonium laureth sulfate, less abrasive and offers enhanced foaming characteristics. Dioxane is found in small amounts in some cosmetics. Since 1979, the U.S. Food and Drug Administration conducted tests on cosmetic raw materials and finished products for the levels of 1,4-dioxane.Mohr Thomas K.G. Environmental Investigation and Remediation 1,4-Dioxane Chemistry, Uses, and Occurrence CRC Press 2020 978-0-429-40142-8 10.1201/9780429401428-2 https://www.taylorfrancis.com/books/9780429685781/chapters/10.1201/9780429401428-2 18 October 2025 94–95, 101 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. 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.Black RE Hurley FJ Havery DC Occurrence of 1,4-dioxane in cosmetic raw materials and finished cosmetic products Journal of AOAC International 84 3 666–70 2001 10.1093/jaoac/84.3.666 11417628 free Since the presence of 1,4-dioxane was recognized, many manufacturers have implemented purification processes, such as vacuum and steam stripping, to reduce its concentration in finished products.Bettenhausen Craig A. How companies are getting 1,4-dioxane out of home and personal care products Chemical & Engineering News 22 March 2020 https://cen.acs.org/business/consumer-products/companies-getting-14-dioxane-home/98/i11 19 October 2025 While the FDA encourages manufacturers to remove 1,4-dioxane, it is not required by federal law.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 On 9 December 2019, the State of New York amended Environmental Conservation Law (ECL) to regulate 1,4-dioxane in consumer products. The law restricts 1,4-dioxane concentrations in household cleansing and personal care products to a maximum of 2 ppm starting 31 December 2022, and a stricter limit of 1 ppm beginning 31 December 2023. Cosmetic products face a maximum allowable concentration of 10 ppm of 1,4-dioxane as of 31 December 2022.https://cen.acs.org/environment/persistent-pollutants/New-York-restricts-14-dioxane/97/web/2019/12 New York restricts 1,4-dioxane in cleaning and personal care products Cen.acs.org 13 November 20211,4-Dioxane Limits for Household Cleansing, Personal Care, and Cosmetic Products Department of Environmental Conservation https://dec.ny.gov/environmental-protection/help-for-businesses/household-personal-cosmetic-dioxane-limits 19 October 2025 See also Dioxolane 9-Crown-3 References Category:Dioxanes Category:Ether solvents Category:IARC Group 2B carcinogens Category:Crown ethers Category:Sweet-smelling chemicals