Which of the following structural formulas contains an ether functional group?

Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R')

For the substance whose common name is ether, see Diethyl ether. For the digital asset, see Ether (cryptocurrency). For other uses, see Ether (disambiguation).

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R−O−R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl or aryl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers.[1] A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (CH3−CH2−O−CH2−CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.[2]

Structure and bonding

Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm.[3] The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.

Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however.

Ethers can be symmetrical of the type ROR or unsymmetrical of the type ROR'. Examples of the former are diethyl ether, dimethyl ether, dipropyl ether etc. Illustrative unsymmetrical ethers are anisole (methoxybenzene) and dimethoxyethane.

Vinyl- and acetylenic ethers

Vinyl- and acetylenic ethers are far less common than alkyl or aryl ethers. Vinylethers, often called enol ethers, are important intermediates in organic synthesis. Acetylenic ethers are especially rare. Di-tert-butoxyacetylene is the most common example of this rare class of compounds.

Nomenclature

In the IUPAC Nomenclature system, ethers are named using the general formula "alkoxyalkane", for example CH3–CH2–O–CH3 is methoxyethane. If the ether is part of a more-complex molecule, it is described as an alkoxy substituent, so –OCH3 would be considered a "methoxy-" group. The simpler alkyl radical is written in front, so CH3–O–CH2CH3 would be given as methoxy(CH3O)ethane(CH2CH3).

Trivial name

IUPAC rules are often not followed for simple ethers. The trivial names for simple ethers (i.e., those with none or few other functional groups) are a composite of the two substituents followed by "ether". For example, ethyl methyl ether (CH3OC2H5), diphenylether (C6H5OC6H5). As for other organic compounds, very common ethers acquired names before rules for nomenclature were formalized. Diethyl ether is simply called ether, but was once called sweet oil of vitriol. Methyl phenyl ether is anisole, because it was originally found in aniseed. The aromatic ethers include furans. Acetals (α-alkoxy ethers R–CH(–OR)–O–R) are another class of ethers with characteristic properties.

Polyethers

Polyethers are generally polymers containing ether linkages in their main chain. The term polyol generally refers to polyether polyols with one or more functional end-groups such as a hydroxyl group. The term "oxide" or other terms are used for high molar mass polymer when end-groups no longer affect polymer properties.

Crown ethers are cyclic polyethers. Some toxins produced by dinoflagellates such as brevetoxin and ciguatoxin are extremely large and are known as cyclic or ladder polyethers.

The phenyl ether polymers are a class of aromatic polyethers containing aromatic cycles in their main chain: polyphenyl ether (PPE) and poly(p-phenylene oxide) (PPO).

Related compounds

Many classes of compounds with C–O–C linkages are not considered ethers: Esters (R–C(=O)–O–R′), hemiacetals (R–CH(–OH)–O–R′), carboxylic acid anhydrides (RC(=O)–O–C(=O)R′).

Physical properties

Ethers have boiling points similar to those of the analogous alkanes. Simple ethers are generally colorless.

Reactions

Structure of the polymeric diethyl ether peroxide

The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical reactivity, they are more reactive than alkanes.

Specialized ethers such as epoxides, ketals, and acetals are unrepresentative classes of ethers and are discussed in separate articles. Important reactions are listed below.[4]

Cleavage

See also: Ether cleavage

Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly. Methyl ethers typically afford methyl halides:

These reactions proceed via onium intermediates, i.e. [RO(H)CH3]+Br−.

Some ethers undergo rapid cleavage with boron tribromide (even aluminium chloride is used in some cases) to give the alkyl bromide.[5] Depending on the substituents, some ethers can be cleaved with a variety of reagents, e.g. strong base.

Peroxide formation

When stored in the presence of air or oxygen, ethers tend to form explosive peroxides, such as diethyl ether hydroperoxide. The reaction is accelerated by light, metal catalysts, and aldehydes. In addition to avoiding storage conditions likely to form peroxides, it is recommended, when an ether is used as a solvent, not to distill it to dryness, as any peroxides that may have formed, being less volatile than the original ether, will become concentrated in the last few drops of liquid. The presence of peroxide in old samples of ethers may be detected by shaking them with freshly prepared solution of a ferrous sulfate followed by addition of KSCN. Appearance of blood red color indicates presence of peroxides. The dangerous properties of ether peroxides are the reason that diethyl ether and other peroxide forming ethers like tetrahydrofuran (THF) or ethylene glycol dimethyl ether (1,2-dimethoxyethane) are avoided in industrial processes.

Lewis bases

Ethers serve as Lewis bases. For instance, diethyl ether forms a complex with boron trifluoride, i.e. diethyl etherate (BF3·OEt2). Ethers also coordinate to the Mg center in Grignard reagents. Tetrahydrofuran is more basic than acyclic ethers. It forms complexes with many metal halides.

Alpha-halogenation

This reactivity is similar to the tendency of ethers with alpha hydrogen atoms to form peroxides. Reaction with chlorine produces alpha-chloroethers.

Synthesis

Ethers can be prepared by numerous routes. In general alkyl ethers form more readily than aryl ethers, with the later species often requiring metal catalysts.[7]

The synthesis of diethyl ether by a reaction between ethanol and sulfuric acid has been known since the 13th century.[8]

Dehydration of alcohols

The dehydration of alcohols affords ethers:[9]

This direct nucleophilic substitution reaction requires elevated temperatures (about 125 °C). The reaction is catalyzed by acids, usually sulfuric acid. The method is effective for generating symmetrical ethers, but not unsymmetrical ethers, since either OH can be protonated, which would give a mixture of products. Diethyl ether is produced from ethanol by this method. Cyclic ethers are readily generated by this approach. Elimination reactions compete with dehydration of the alcohol:

The dehydration route often requires conditions incompatible with delicate molecules. Several milder methods exist to produce ethers.

Williamson ether synthesis

Nucleophilic displacement of alkyl halides by alkoxides

This reaction is called the Williamson ether synthesis. It involves treatment of a parent alcohol with a strong base to form the alkoxide, followed by addition of an appropriate aliphatic compound bearing a suitable leaving group (R–X). Suitable leaving groups (X) include iodide, bromide, or sulfonates. This method usually does not work well for aryl halides (e.g. bromobenzene, see Ullmann condensation below). Likewise, this method only gives the best yields for primary halides. Secondary and tertiary halides are prone to undergo E2 elimination on exposure to the basic alkoxide anion used in the reaction due to steric hindrance from the large alkyl groups.

In a related reaction, alkyl halides undergo nucleophilic displacement by phenoxides. The R–X cannot be used to react with the alcohol. However phenols can be used to replace the alcohol while maintaining the alkyl halide. Since phenols are acidic, they readily react with a strong base like sodium hydroxide to form phenoxide ions. The phenoxide ion will then substitute the –X group in the alkyl halide, forming an ether with an aryl group attached to it in a reaction with an SN2 mechanism.

Ullmann condensation

The Ullmann condensation is similar to the Williamson method except that the substrate is an aryl halide. Such reactions generally require a catalyst, such as copper.

Electrophilic addition of alcohols to alkenes

Alcohols add to electrophilically activated alkenes.

Acid catalysis is required for this reaction. Often, mercury trifluoroacetate (Hg(OCOCF3)2) is used as a catalyst for the reaction generating an ether with Markovnikov regiochemistry. Using similar reactions, tetrahydropyranyl ethers are used as protective groups for alcohols.

Preparation of epoxides

Main article: epoxide

Epoxides are typically prepared by oxidation of alkenes. The most important epoxide in terms of industrial scale is ethylene oxide, which is produced by oxidation of ethylene with oxygen. Other epoxides are produced by one of two routes:

• By the oxidation of alkenes with a peroxyacid such as m-CPBA.
• By the base intramolecular nucleophilic substitution of a halohydrin.

Important ethers

	Ethylene oxide	A cyclic ether. Also the simplest epoxide.
	Dimethyl ether	A colourless gas that is used as an aerosol spray propellant. A potential renewable alternative fuel for diesel engines with a cetane rating as high as 56–57.
	Diethyl ether	A colourless liquid with sweet odour. A common low boiling solvent (b.p. 34.6 °C) and an early anaesthetic. Used as starting fluid for diesel engines. Also used as a refrigerant and in the manufacture of smokeless gunpowder, along with use in perfumery.
	Dimethoxyethane (DME)	A water miscible solvent often found in lithium batteries (b.p. 85 °C):
	Dioxane	A cyclic ether and high-boiling solvent (b.p. 101.1 °C).
	Tetrahydrofuran (THF)	A cyclic ether, one of the most polar simple ethers that is used as a solvent.
	Anisole (methoxybenzene)	An aryl ether and a major constituent of the essential oil of anise seed.
	Crown ethers	Cyclic polyethers that are used as phase transfer catalysts.
	Polyethylene glycol (PEG)	A linear polyether, e.g. used in cosmetics and pharmaceuticals.
	Polypropylene glycol	A linear polyether, e.g. used in polyurethanes.
	Platelet-activating factor	An ether lipid, an example with an ether on sn-1, an ester on sn-2, and an inorganic ether on sn-3 of the glyceryl scaffold.

See also

• Ester
• Ether lipid
• Ether addiction
• Ether (song)
• History of general anesthesia
• Inhalant

References

1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "ethers". doi:10.1351/goldbook.E02221
2. ^ Saul Patai, ed. (1967). The Ether Linkage. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470771075. ISBN 9780470771075.
3. ^ Vojinović, Krunoslav; Losehand, Udo; Mitzel, Norbert W. (2004). "Dichlorosilane–Dimethyl Ether Aggregation: A New Motif in Halosilane Adduct Formation". Dalton Trans. (16): 2578–2581. doi:10.1039/b405684a. PMID 15303175.
4. ^ Wilhelm Heitmann, Günther Strehlke, Dieter Mayer "Ethers, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a10_023
5. ^ J. F. W. McOmie and D. E. West (1973). "3,3′-Dihydroxylbiphenyl". Organic Syntheses.; Collective Volume, vol. 5, p. 412
6. ^ F.A.Cotton, S.A.Duraj, G.L.Powell, W.J.Roth (1986). "Comparative Structural Studies of the First Row Early Transition Metal(III) Chloride Tetrahydrofuran Solvates". Inorg. Chim. Acta. 113: 81. doi:10.1016/S0020-1693(00)86863-2.{{cite journal}}: CS1 maint: uses authors parameter (link)
7. ^ Frlan, Rok; Kikelj, Danijel (29 June 2006). "Recent Progress in Diaryl Ether Synthesis". Synthesis. 2006 (14): 2271–2285. doi:10.1055/s-2006-942440.
8. ^ Chisholm, Hugh, ed. (1911). "Ether" . Encyclopædia Britannica. Vol. 9 (11th ed.). Cambridge University Press. p. 806.
9. ^ Clayden; Greeves; Warren (2001). Organic chemistry. Oxford University Press. p. 129. ISBN 978-0-19-850346-0.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Ether&oldid=1122481274"

Page 2

Not to be confused with 1,4-Dioxin.

"Dioxane" redirects here. For other uses, see Dioxane (compounds).

1,4-Dioxane

1,4-Dioxacyclohexane

[1,4]Dioxane
p-Dioxane
[6]-crown-2
Diethylene dioxide
Diethylene ether
Dioxane solvent

CAS Number

• 123-91-1 
  
  Y

3D model (JSmol)

• Interactive image

Beilstein Reference

• CHEBI:47032 
  
  Y

• ChEMBL453716 
  
  Y

• 29015 
  
  Y

• DB03316 
  
  Y

• 204-661-8

• C14440 
  
  Y

PubChem CID

• 31275

• JG8225000

• J8A3S10O7S 
  
  Y

CompTox Dashboard (EPA)

• DTXSID4020533
  

InChI

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

  
  Y

  Key: RYHBNJHYFVUHQT-UHFFFAOYSA-N 

  
  Y

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

  Key: RYHBNJHYFVUHQT-UHFFFAOYAN

SMILES

• O1CCOCC1

Chemical formula

Solubility in water

Magnetic susceptibility (χ)

Std molar
entropy (S⦵298)

Std enthalpy of
formation (ΔfH⦵298)

Std enthalpy of
combustion (ΔcH⦵298)

Main hazards

Pictograms

Signal word

Hazard statements

Precautionary statements

2

3

1

Autoignition
temperature

LD50 (median dose)

• 5 g/kg (mouse, oral)
• 4 g/kg (rat, oral)
• 3 g/kg (guinea pig, oral)
• 7.6 g/kg (rabbit, dermal)

LC50 (median concentration)

• 10,109 ppm (mouse, 2 hr)
• 12,568 ppm (rat, 2 hr)[2]

LCLo (lowest published)

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

PEL (Permissible)

REL (Recommended)

IDLH (Immediate danger)

Related compounds

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

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 aluminum 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 aluminum trichloride.[4]

As a solvent

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 Lewis-basic, and so dioxane is able to solvate many inorganic compounds and serves as a chelating diether ligand. It forms 1:1 adducts with a variety of Lewis acids such as I2, phenols, alcohols, and bis(hexafloroacetylacetonato)copper(II). It is classified as a hard base and its base parameters in the ECW model are EB =1.86 and CB = 1.29. It reacts with Grignard reagents to precipitate the magnesium dihalide. In this way, dioxane is used to drive the Schlenk equilibrium.[4] Dimethylmagnesium is prepared in this manner:[8][9]

Spectroscopy

Dioxane is used as an internal standard for nuclear magnetic resonance spectroscopy in deuterium oxide.[10]

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.[11] In a 1978 mortality study conducted on workers exposed to 1,4-dioxane, the observed number deaths from cancer was not significantly different from the expected number.[12] Dioxane is classified by the National Toxicology Program as "reasonably anticipated to be a human carcinogen".[13] 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.[14] 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.[15] Under California Proposition 65, dioxane is classified in the U.S. State of California to cause cancer.[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]

It 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]

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 under metallic sodium could limit the risk of explosion.

Environment

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

• 1,2-Dioxane
• 1,3-Dioxane
• Dioxolane
• 9-crown-3
• Crown ether
• Dioxane tetraketone
• Oxalic anhydride
• Sodium laureth sulfate
• Dioxanone

References

1. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0237". National Institute for Occupational Safety and Health (NIOSH).
2. ^ a b "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. Publication 00514. Accessed 2016-11-12.
4. ^ a b c d Surprenant, Kenneth S. (2000). "Dioxane". Dioxane in Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_545. ISBN 978-3527306732.
5. ^ a b "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, C. H.; Lynch, C. C.: The Ternary System: Dioxane-Ethanol-Water in J. Am. Chem. Soc., 1943, vol. 65, pp 1063–1066. doi:10.1021/ja01246a015.
8. ^ 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.
9. ^ 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.
10. ^ 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.
11. ^ "International Chemical Safety Card". National Institute for Occupational Safety and Health. Archived from the original on 29 April 2005. Retrieved 6 February 2006.
12. ^ 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.
13. ^ "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.
14. ^ IARC Monographs Volume 71 (PDF). International Agency for Research on Cancer. Retrieved 11 July 2014.
15. ^ 1,4-Dioxane (1,4-Diethyleneoxide). Hazard Summary. U.S. Environmental Protection Agency. Created in April 1992; Revised in January 2000. Fact Sheet.
16. ^ "Chemicals Known to the State to Cause Cancer or Reproductive Toxicity" (PDF). Office of Environmental Health Hazard Assessment. 2 April 2010. Archived from the original (PDF) on 24 May 2010. Retrieved 14 December 2013. 1,4-Dioxane CAS#123-91-1 (Listed 1 January 1988)
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. 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. 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. ^ a b c 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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