Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1,4-Dioxane: Difference between pages

{{Distinguish|1,4-Dioxin}}

{{Redirect|Dioxane|other uses|Dioxane (compounds)}}

{{Use dmy dates|date=May 2020}}

{{Chembox

| Watchedfields = changed

|verifiedrevid = 477206315

|ImageFileL1 = 1-4-Dioxane.svg

|ImageNameL1 = Chemical structure of dioxane

|ImageSizeL1 = 90px

|ImageFileR1 = 1,4-Dioxane-3D-balls.png

|ImageSizeR1 = 130px

|ImageNameR1 = 1,4-dioxane

|ImageFile2 = 1,4-dioxane.png

|ImageSize2 = 150px

|PIN = 1,4-Dioxane

|SystematicName= 1,4-Dioxacyclohexane

|OtherNames = [1,4]Dioxane<br />''p''-Dioxane<br />[6]-crown-2<br />Diethylene dioxide<br />Diethylene ether<br />Dioxane solvent

|Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChEBI = 47032

|ChemSpiderID = 29015

|KEGG = C14440

|InChI = 1/C4H8O2/c1-2-6-4-3-5-1/h1-4H2

|InChIKey = RYHBNJHYFVUHQT-UHFFFAOYAN

|ChEMBL = 453716

|StdInChI = 1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2

|StdInChIKey = RYHBNJHYFVUHQT-UHFFFAOYSA-N

|CASNo = 123-91-1

|EINECS = 204-661-8

| UNII_Ref = {{fdacite|correct|FDA}}

|UNII = J8A3S10O7S

|DrugBank = DB03316

| PubChem = 31275

| RTECS = JG8225000

| UNNumber = 1165

| Beilstein = 102551

|SMILES = O1CCOCC1

|Section2 = {{Chembox Properties

|C = 4 |H = 8 |O = 2

|MeltingPtC = 11.8

|BoilingPtC = 101.1

|Density = 1.033&nbsp;g/mL

|Solubility = Miscible

|Appearance = Colorless liquid<ref name=PGCH />

|Odor = Mild, [[diethyl ether]]-like<ref name=PGCH />

|VaporPressure = 29&nbsp;mmHg (20&nbsp;°C)<ref name=PGCH />

| MagSus = −52.16·10{{sup|−6}}&nbsp;cm{{sup|3}}/mol

|Section4 = {{Chembox Thermochemistry

|DeltaHf = −354&nbsp;kJ/mol

|DeltaHc = −2363&nbsp;kJ/mol

|Entropy = 196.6&nbsp;J/K·mol

}}

|Section7 = {{Chembox Hazards

|NFPA-H = 2

|NFPA-F = 3

|NFPA-R = 1

| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|225|302|305|315|319|332|336|351|370|372|373}}

| PPhrases = {{P-phrases|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}}

|FlashPtC = 12

| AutoignitionPtC = 180

|PEL = TWA 100&nbsp;ppm (360&nbsp;mg/m{{sup|3}}) [skin]<ref name=PGCH>{{PGCH|0237}}</ref>

|ExploLimits = 2.0–22%<ref name=PGCH />

|IDLH = Ca [500&nbsp;ppm]<ref name=PGCH />

|REL = Ca C 1&nbsp;ppm (3.6&nbsp;mg/m{{sup|3}}) [30-minute]<ref name=PGCH />

|MainHazards = Suspected human carcinogen<ref name=PGCH />

|LC50 = {{Unbulleted list

| 10,109&nbsp;ppm (mouse, 2&nbsp;hr)

| 12,568 ppm (rat, 2 hr)<ref name=IDLH>{{IDLH|123911|Dioxane}}</ref>

}}

|LCLo = 1000–3000&nbsp;ppm (guinea pig, 3&nbsp;hr)<br />

12,022&nbsp;ppm (cat, 7&nbsp;hr)<br />

2085&nbsp;ppm (mouse, 8&nbsp;hr)<ref name=IDLH />

|LD50 = {{Unbulleted list

| 5&nbsp;g/kg (mouse, oral)

| 4&nbsp;g/kg (rat, oral)

| 3&nbsp;g/kg (guinea pig, oral)

| 7.6&nbsp;g/kg (rabbit, dermal)

}}

}}

|Section8 = {{Chembox Related

|Related_ref =

|OtherAnions =

|OtherCations =

|OtherFunction =

|OtherFunction_label =

|OtherCompounds = [[Oxane]]<br />[[Trioxane]]<br />[[Tetroxane]]<br />[[Pentoxane]]

}}

}}

'''1,4-Dioxane''' ({{IPAc-en|d|aɪ|ˈ|ɒ|k|s|eɪ|n}}) is a [[Heterocyclic compound|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 [[isomer]]s ([[1,2-Dioxane|1,2-]] and [[1,3-Dioxane|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.<ref name=wisc>Wisconsin Department of Health Services (2013) [https://www.dhs.wisconsin.gov/publications/p0/p00514.pdf 1,4-Dioxane Fact Sheet] {{Webarchive|url=https://web.archive.org/web/20201016235134/https://www.dhs.wisconsin.gov/publications/p0/p00514.pdf |date=16 October 2020 }}. Publication 00514. Accessed 2016-11-12.</ref>

== Synthesis ==

Dioxane is produced by the acid-catalysed [[Dehydration reaction|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.<ref name=Ullmann /> In 1990, the total U.S. production volume of dioxane was between 5,250 and 9,150 tons.<ref name=OPPT>{{cite web |url= http://www.epa.gov/chemfact/dioxa-sd.pdf |publisher= [[United States Environmental Protection Agency]] |work= OPPT Chemical Fact Sheets |date= February 1995 |title= 1, 4-Dioxane Fact Sheet: Support Document |access-date=14 May 2010 <!--Added by DASHBot-->}}</ref>

== 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|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.<ref name=Ullmann>{{cite book |last1=Surprenant |first1=Kenneth S. |title=Dioxane in Ullmann's Encyclopedia of Industrial Chemistry |year=2000 |doi=10.1002/14356007.a08_545|chapter=Dioxane |isbn=978-3527306732 }}</ref>

=== As a solvent ===

[[File:Binary phase diagram dioxane-water.svg|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]], 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&nbsp;°C, versus 66&nbsp;°C for THF).<ref name=weiss>Klaus Weissermel, Hans-Jürgen Arpe (2003) "Industrial Organic Chemistry". John Wiley & Sons, page 158. {{ISBN|3527305785}}, 9783527305780.</ref>

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.<ref>{{cite journal | doi = 10.1021/ja01246a015 | title = The Ternary System: Dioxane—Ethanol—Water | date = 1943 | last1 = Schneider | first1 = Charles H. | last2 = Lynch | first2 = Cecil C. | journal = Journal of the American Chemical Society | volume = 65 | issue = 6 | pages = 1063–1066 }}</ref>

The oxygen atoms are weakly [[Lewis base|Lewis-basic]]. It forms adducts with a variety of Lewis acids. It is classified as a [[HSAB theory|hard base]] and its base parameters in the [[ECW model]] are E_B&nbsp;=&nbsp;1.86 and C_B&nbsp;=&nbsp;1.29.

Dioxane produces [[coordination polymer]]s by linking metal centers.<ref>{{cite journal |doi=10.1002/chem.201903120|title=Structure–Solubility Relationship of 1,4-Dioxane Complexes of Di(hydrocarbyl)magnesium |year=2019 |last1=Fischer |first1=Reinald |last2=Görls |first2=Helmar |last3=Meisinger |first3=Philippe R. |last4=Suxdorf |first4=Regina |last5=Westerhausen |first5=Matthias |journal=Chemistry – A European Journal |volume=25 |issue=55 |pages=12830–12841 |pmid=31328293 |pmc=7027550 }}</ref> In this way, it is used to drive the [[Schlenk equilibrium]], allowing the synthesis of dialkyl magnesium compounds.<ref name=Ullmann /> [[Dimethylmagnesium]] is prepared in this manner:<ref>{{cite journal |title=The Preparation of Dialkylmagnesium Compounds from Grignard Reagents|last1=Cope |first1=Arthur C. |journal=Journal of the American Chemical Society |volume=57 |page=2238 |year=1935 |doi=10.1021/ja01314a059 |issue=11}}</ref><ref>{{cite journal |last1=Anteunis |first1=M. |title=Studies of the Grignard Reaction. II. Kinetics of the Reaction of Dimethylmagnesium with Benzophenone and of Methylmagnesium Bromide-Magnesium Bromide with Pinacolone |journal=The Journal of Organic Chemistry |volume=27 |page=596 |year=1962 |doi=10.1021/jo01049a060 |issue=2}}</ref>

:2 CH{{sub|3}}MgBr + (C{{sub|2}}H{{sub|4}}O){{sub|2}} → MgBr{{sub|2}}(C{{sub|2}}H{{sub|4}}O){{sub|2}} + (CH{{sub|3}}){{sub|2}}Mg

=== Spectroscopy ===

Dioxane is used as an internal standard for [[nuclear magnetic resonance spectroscopy]] in [[deuterium oxide]].<ref>{{cite journal |last1=Shimizu |first1=A. |last2=Ikeguchi |first2=M. |last3=Sugai |first3=S. |title=Appropriateness of DSS and TSP as internal references for 1H NMR studies of molten globule proteins in aqueous media |journal=[[Journal of Biomolecular NMR]] |volume=4 |year=1994 |doi=10.1007/BF00398414 |pmid=22911388 |issue=6|pages=859–62 |s2cid=34800494 }}</ref>

== Toxicology ==

=== Safety ===

Dioxane has an {{LD50}} of 5170&nbsp;mg/kg in rats.<ref name=Ullmann /> It is irritating to the eyes and respiratory tract. Exposure may cause damage to the central nervous system, liver and kidneys.<ref>{{cite web

|title = International Chemical Safety Card

|publisher = National Institute for Occupational Safety and Health

|url = https://www.cdc.gov/niosh/ipcsneng/neng0041.html

|access-date = 6 February 2006

|archive-url = https://web.archive.org/web/20050429004946/http://www.cdc.gov/niosh/ipcsneng/neng0041.html

|archive-date = 29 April 2005

|url-status = dead}}</ref> 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.<ref>{{cite journal

|title= Mortality Follow-up of Workers Exposed to 1,4-Dioxane.

|journal= Journal of Occupational and Environmental Medicine

|volume= 20

|issue= 4

|pages= 255–259

|url= http://journals.lww.com/joem/Abstract/1978/04000/Mortality_Follow_up_of_Workers_Exposed_to.6.aspx

|access-date =26 March 2016|date= April 1978

|last1= Buffler

|first1= Patricia A.

|last2= Wood

|first2= Susan M.

|last3= Suarez

|first3= Lucina

|last4= Kilian

|first4= Duane J.

|pmid= 641607

}}</ref> Dioxane is classified by the National Toxicology Program as "reasonably anticipated to be a human carcinogen".<ref>{{cite web

|title = 12th Report on Carcinogens

|publisher = United States Department of Health and Human Services' National Toxicology Program

|url = https://ntp.niehs.nih.gov/go/roc12

|access-date = 11 July 2014

|archive-url = https://web.archive.org/web/20140714132609/http://ntp.niehs.nih.gov/pubhealth/roc/roc12/index.html

|archive-date = 14 July 2014

|url-status = dead}}</ref> It is also classified by the [[International Agency for Research on Cancer|IARC]] as a [[List of IARC Group 2B carcinogens|Group 2B carcinogen]]: ''possibly carcinogenic to humans'' because it is a known carcinogen in other animals.<ref>{{cite book |title= IARC Monographs Volume 71 |publisher= International Agency for Research on Cancer |url= http://monographs.iarc.fr/ENG/Monographs/vol71/mono71-25.pdf|access-date =11 July 2014}}</ref> 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.<ref name="U.S.EPA_Dioxane">1,4-Dioxane (1,4-Diethyleneoxide). Hazard Summary. ''U.S. Environmental Protection Agency''. Created in April 1992; Revised in January 2000. [http://www.epa.gov/ttn/atw/hlthef/dioxane.html Fact Sheet].</ref> Animal studies in rats suggest that the greatest health risk is associated with inhalation of vapors in the pure form.<ref>{{cite journal |doi=10.2131/jts.33.141 |last1=Kano |first1=Hirokazu |last2=Umeda |first2=Yumi |last3=Saito |first3=Misae |last4=Senoh |first4=Hideki |last5=Ohbayashi |first5=Hisao |last6=Aiso |first6=Shigetoshi |last7=Yamazaki |first7=Kazunori |last8=Nagano |first8=Kasuke |last9=Fukushima |first9=Shoji |title=Thirteen-week oral toxicity of 1,4-dioxane in rats and mice |journal=The Journal of Toxicological Sciences |volume=33 |issue=2 |pages=141–53 |year=2008 |pmid=18544906|doi-access=free }}</ref><ref>{{cite journal |last1=Kasai |first1=T |last2=Saito |first2=M |last3=Senoh |first3=H |last4=Umeda |first4=Y |last5=Aiso |first5=S |last6=Ohbayashi |first6=H |last7=Nishizawa |first7=T |last8=Nagano |first8=K |last9=Fukushima |first9=S |title=Thirteen-week inhalation toxicity of 1,4-dioxane in rats |journal=Inhalation Toxicology |volume=20 |issue=10 |pages=961–71 |year=2008 |pmid=18668411 |doi=10.1080/08958370802105397|bibcode=2008InhTx..20..961K |s2cid=86811931 }}</ref><ref>{{cite journal |last1=Kasai |first1=T. |last2=Kano |first2=H. |last3=Umeda |first3=Y. |last4=Sasaki |first4=T. |last5=Ikawa |first5=N. |last6=Nishizawa |first6=T. |last7=Nagano |first7=K. |last8=Arito |first8=H. |last9=Nagashima |first9=H. |last10=Fukushima |first10=S.|title=Two-year inhalation study of carcinogenicity and chronic toxicity of 1,4-dioxane in male rats |journal=Inhalation Toxicology |volume=21 |issue=11 |pages=889–97 |year=2009 |doi=10.1080/08958370802629610 |pmid=19681729 |bibcode=2009InhTx..21..889K |s2cid=45963495 }}</ref> 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.<ref>{{Cite web |url=https://www.governor.ny.gov/news/governor-cuomo-announces-first-nation-drinking-water-standard-emerging-contaminant-14-dioxane |title = Governor Cuomo Announces First in the Nation Drinking Water Standard for Emerging Contaminant 1,4-Dioxane {{!}} Governor Andrew M. Cuomo |access-date=30 October 2020 |archive-date=29 October 2020 |archive-url=https://web.archive.org/web/20201029142313/https://www.governor.ny.gov/news/governor-cuomo-announces-first-nation-drinking-water-standard-emerging-contaminant-14-dioxane |url-status=dead }}</ref>

=== Explosion hazard ===

Like some other ethers, dioxane combines with atmospheric oxygen upon prolonged exposure to air to form potentially explosive [[peroxide]]s. [[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.<ref>{{cite journal |last1=Zenker |first1=Matthew J. |last2=Borden |first2=Robert C. |last3=Barlaz |first3=Morton A. |title=Occurrence and Treatment of 1,4-Dioxane in Aqueous Environments |journal=Environmental Engineering Science |date=September 2003 |volume=20 |issue=5 |pages=423–432 |doi=10.1089/109287503768335913}}</ref><ref>{{cite journal |last1=Zhang |first1=Shu |last2=Gedalanga |first2=Phillip B. |last3=Mahendra |first3=Shaily |title=Advances in bioremediation of 1,4-dioxane-contaminated waters |journal=Journal of Environmental Management |date=December 2017 |volume=204 |issue=Pt 2 |pages=765–774 |doi=10.1016/j.jenvman.2017.05.033|pmid=28625566 |doi-access=free }}</ref>

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.<ref name="OPPT" /> 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.<ref>{{Cite web |date=2020-11-18 |title=1,4-dioxane in Greensboro {{!}} Haw River Assembly |url=https://hawriver.org/14-dioxane-in-greensboro/ |access-date=2022-05-13 |language=en-US}}</ref>

=== 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.<ref>[http://ehp.niehs.nih.gov/roc/tenth/profiles/s080diox.pdf Tenth Report on Carcinogens] {{Webarchive|url=https://web.archive.org/web/20041101071935/http://ehp.niehs.nih.gov/roc/tenth/profiles/s080diox.pdf |date=1 November 2004 }}. U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program, December 2002.</ref><ref>{{cite web |title= Chemical Encyclopedia: 1,4-dioxane |publisher= Healthy Child Healthy World |url= http://healthychild.org/issues/chemical-pop/1,4-dioxane/ |access-date =14 December 2009 |archive-url= https://web.archive.org/web/20091129073643/http://healthychild.org/issues/chemical-pop/1,4-dioxane/ |archive-date= 29 November 2009 <!--Added by DASHBot-->}}</ref> 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.<ref>{{cite news |publisher=Xinhua |title=Watchdog issues inspection results on Johnson & Johnson |url=http://www.chinadaily.com.cn/china/2009-03/21/content_7603271.htm |work=China Daily |date=21 March 2009 |access-date=14 May 2010 <!--Added by DASHBot-->}}</ref> 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.<ref>{{cite news |publisher=Aspen Clean |title=The Dangers of 1,4-Dioxane and How to Avoid It |url=https://www.aspenclean.com/blog/what-is-dioxane#What-is-1.4-Dioxane |work=Aspen Clean |date=11 February 2020 |access-date=17 December 2020 <!--Added by DASHBot-->}}</ref>

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.<ref name="Occurrence_Dioxane" /> 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.<ref name="Occurrence_Dioxane" /> 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.<ref name="Occurrence_Dioxane">{{cite journal |last1=Black |first1=RE |last2=Hurley |first2=FJ |last3=Havery |first3=DC |title=Occurrence of 1,4-dioxane in cosmetic raw materials and finished cosmetic products |journal=Journal of AOAC International |volume=84 |issue=3 |pages=666–70 |year=2001 |doi=10.1093/jaoac/84.3.666 |pmid=11417628|doi-access=free }}</ref> While the FDA encourages manufacturers to remove 1,4-dioxane, it is not required by federal law.<ref name="FDA_Dioxane">FDA/CFSAN--Cosmetics Handbook Part 3: Cosmetic Product-Related Regulatory Requirements and Health Hazard Issues. [https://web.archive.org/web/20080115201046/http://www.cfsan.fda.gov/~dms/cos-hdb3.html Prohibited Ingredients and other Hazardous Substances: 9. Dioxane] Web.archive.org</ref>

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.<ref>{{cite web|url=https://cen.acs.org/environment/persistent-pollutants/New-York-restricts-14-dioxane/97/web/2019/12|title=New York restricts 1,4-dioxane in cleaning and personal care products|website=Cen.acs.org|access-date=13 November 2021}}</ref>

== See also ==

[[File:Dioxane isomers named.PNG|thumb|upright=1.2|The three isomers of dioxane]]

* [[Dioxolane]]

* [[9-crown-3]]

* [[Dioxane tetraketone]]

* [[Oxalic anhydride]]

* [[Dioxanone]]

{{clear|right}}

== References ==

{{Reflist}}

{{Authority control}}

{{DEFAULTSORT:Dioxane, 1, 4-}}

[[Category:Dioxanes]]

[[Category:Ether solvents]]

[[Category:IARC Group 2B carcinogens]]

[[Category:Crown ethers]]

[[Category:Sweet-smelling chemicals]]