1,4-Dioxane

Revision as of 18:48, 8 August 2012 by WikiBot (talk | contribs) (Bot: Automated text replacement (-{{SIB}} + & -{{EH}} + & -{{EJ}} + & -{{Editor Help}} + & -{{Editor Join}} +))
(diff) ← Older revision | Latest revision (diff) | Newer revision → (diff)
Jump to navigation Jump to search

Template:Chembox new

WikiDoc Resources for 1,4-Dioxane

Articles

Most recent articles on 1,4-Dioxane

Most cited articles on 1,4-Dioxane

Review articles on 1,4-Dioxane

Articles on 1,4-Dioxane in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on 1,4-Dioxane

Images of 1,4-Dioxane

Photos of 1,4-Dioxane

Podcasts & MP3s on 1,4-Dioxane

Videos on 1,4-Dioxane

Evidence Based Medicine

Cochrane Collaboration on 1,4-Dioxane

Bandolier on 1,4-Dioxane

TRIP on 1,4-Dioxane

Clinical Trials

Ongoing Trials on 1,4-Dioxane at Clinical Trials.gov

Trial results on 1,4-Dioxane

Clinical Trials on 1,4-Dioxane at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on 1,4-Dioxane

NICE Guidance on 1,4-Dioxane

NHS PRODIGY Guidance

FDA on 1,4-Dioxane

CDC on 1,4-Dioxane

Books

Books on 1,4-Dioxane

News

1,4-Dioxane in the news

Be alerted to news on 1,4-Dioxane

News trends on 1,4-Dioxane

Commentary

Blogs on 1,4-Dioxane

Definitions

Definitions of 1,4-Dioxane

Patient Resources / Community

Patient resources on 1,4-Dioxane

Discussion groups on 1,4-Dioxane

Patient Handouts on 1,4-Dioxane

Directions to Hospitals Treating 1,4-Dioxane

Risk calculators and risk factors for 1,4-Dioxane

Healthcare Provider Resources

Symptoms of 1,4-Dioxane

Causes & Risk Factors for 1,4-Dioxane

Diagnostic studies for 1,4-Dioxane

Treatment of 1,4-Dioxane

Continuing Medical Education (CME)

CME Programs on 1,4-Dioxane

International

1,4-Dioxane en Espanol

1,4-Dioxane en Francais

Business

1,4-Dioxane in the Marketplace

Patents on 1,4-Dioxane

Experimental / Informatics

List of terms related to 1,4-Dioxane


Overview

1,4-Dioxane, often just called dioxane, is a clear, colorless heterocyclic organic compound which is a liquid at room temperature and pressure. It has the molecular formula C4H8O2 and a boiling point of 101°C. It is commonly used as an aprotic solvent. 1,4-Dioxane has a weak smell similar to that of diethyl ether. There are also two other less common isomeric compounds, 1,2-dioxane and 1,3-dioxane. 1,2-Dioxane is a peroxide which forms naturally in old bottles of tetrahydrofuran.

1,4-Dioxane is classified as an ether, with each of its two oxygen atoms forming an ether functional group. It is more polar than diethyl ether, which also has four carbons, but only one ether functional group. Diethyl ether is rather insoluble in water, but 1,4-dioxane is miscible with water and is hygroscopic. Its higher polarity and slightly higher molecular mass also gives it a substantially higher boiling point than diethyl ether. When used as a solvent for a grignard reaction, Dioxane favorably affects the formation of magnesium halide salts in the Schlenk equilibrium.

The name dioxane should not be confused with dioxin, which is a different compound but is also a diether (two ether functional groups).

File:Dioxane isomers.PNG
Isomers of Dioxane

Small blue numbers show numbering of atoms in rings.


Uses

1,4-Dioxane is primarily used in solvent applications for the manufacturing sector; however, it is also found in fumigants and automotive coolant. Additionally, the chemical is also used as a foaming agent and appears as an accidental byproduct of the ethoxylation[1] process in cosmetics manufacturing. It may contaminate cosmetics and personal care products such as deodorants, shampoos, toothpastes and mouthwashes.[2]

It is also commonly used as an internal standard for calibrating chemical shifts in NMR, as tetramethylsilane (the compound to which all chemical shifts are ultimately referenced) is not soluble in D2O.

Safety & environmental concerns

Dioxanes combine with atmospheric oxygen on standing to form explosive peroxides, similar to many other ethers. Distillation of dioxanes concentrates these peroxides increasing the danger. Appropriate precautions should be taken.

1,4-dioxane is a known eye and respiratory tract irritant. It is suspected of causing damage to the central nervous system, liver and kidneys.[3] Accidental worker exposure to 1,4-dioxane has resulted in several deaths.[4] Dioxane is classified by the IARC as a Group 2B carcinogen: possibly carcinogenic to humans due to the fact that it is a known carcinogen in animals.[5]

Like many solvents, 1,4-dioxane forms contamination plumes in groundwater when released to the environment. Groundwater supplies have been adversely impacted in several areas.

1,4-dioxane is highly soluble in groundwater, does not readily bind to soils, and readily leaches to groundwater. It is also resistant to naturally occurring biodegradation processes. Due to these properties, a 1,4-dioxane plume is often much larger (and further downgradient) than the associated solvent plume.[6]

See also

References

  1. Roderick E. Black. "Occurrence of 1,4-Dioxane in Cosmetic Raw Materials and Finished Cosmetic Products". Journal of IAOC International. Retrieved 2006-02-02. Text " volume: 84 " ignored (help); Text " Issue: 3 " ignored (help); Text " page(s): 666-670 " ignored (help); Text " Cover date: May 2001 " ignored (help)
  2. "CHEC Chemical Summary: 1,4-dioxane". Children's Health Environmental Coalition. Retrieved 2006-02-02.
  3. "International Chemical Safety Card". National Institute for Occupational Safety and Health. Retrieved 2006-02-02.
  4. "OPPT Chemical Fact Sheets 1,4-Dioxane (CAS No. 123-91-1)". United States Environmental Protection Agency. Retrieved 2006-02-02.
  5. "Eleventh Report on Carcinogens" (PDF). United States Department of Health and Human Services’ National Toxicology Program. Retrieved 2006-02-02.
  6. "Crawford, Scott. "Down N' Dirty With 1,4-Dioxane."" (PDF). XDD, LLC's Xpert Solutions Newsletter (Fall 2007/Winter 2008). Retrieved 2008-01-16.

External links

cs:1,4-dioxan de:1,4-Dioxan et:Dioksaan it:Diossano lv:Dioksāns nl:1,4-Dioxaan sv:1,4-Dioxan Template:WH Template:WS