View source for Epichlorohydrin

{{chembox
| verifiedrevid = 301210858
|  Reference=<ref>''Merck Index'', 12th Edition, '''3648'''.</ref>
|   Name = (±)-Epichlorohydrin
|   ImageFile = Epichlorohydrin.png
<!-- | ImageSize = 200px -->
|   ImageName = Epichlorohydrin
|   ImageFile1 = Epichlorohydrin-3D-balls.png
<!-- | ImageSize1 = 200px  -->
|   ImageName1 = Ball-and-stick model of the epichlorohydrin molecule
|   IUPACName = chloromethyloxirane
|   OtherNames = epichlorohydrin<br />1-chloro-2,3-epoxypropane<br />γ-chloropropylene oxide<br />glycidyl chloride
| Section1 = {{Chembox Identifiers
|   CASNo_Ref = {{cascite}}
| CASNo = 106-89-8
|   PubChem = 7835
|   ChemSpiderID = 7547
|   SMILES = C1C2(O1)C2Cl
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>3</sub>H<sub>5</sub>ClO
|   MolarMass = 92.52 g/mol
|   Density = 1.1812 g/cm<sup>3</sup>
|   MeltingPt = -25.6 °C
|   BoilingPt = 117.9 °C
  }}
| Section7 = {{Chembox Hazards
|   ExternalMSDS =[http://physchem.ox.ac.uk/MSDS/EP/epichlorohydrin.html External MSDS]
|   EUClass = {{Hazchem T}}
|   NFPA-H = 3
|   NFPA-R = 2
|   NFPA-F = 3
  }}
}}

'''Epichlorohydrin''' is an [[organochlorine compound]] and an [[epoxide]]. This is a colorless liquid with a pungent, garlic-like odor, insoluble in water, but [[miscibility|miscible]] with most [[polar molecule|polar]] [[Organic compound|organic]] [[solvent]]s.<ref name="EPA">[http://www.epa.gov/safewater/contaminants/dw_contamfs/epichlor.html EPA consumer factsheet]</ref>  Epichlorohydrin is a highly reactive compound and is used in the production of [[glycerol]], plastics, [[epoxy glue]]s and [[Epoxy resin|resins]], and [[elastomer]]s. In contact with water, epichlorohydrin hydrolyzes to [[3-MCPD]], a [[carcinogen]] found in food.

==Production==
Epichlorohydrin is manufactured from [[allyl chloride]] in two steps, beginning with the hydrochlorination using [[hypochlorous acid]], which affords a mixture of two alcohols:<ref name=Ullmann>Guenter Sienel, Robert Rieth, Kenneth T. Rowbottom "Epoxides" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.</ref>

:CH<sub>2</sub>=CHCH<sub>2</sub>Cl  +  HOCl   →  HOCH<sub>2</sub>CHClCH<sub>2</sub>Cl  and, or   ClCH<sub>2</sub>CH(OH)CH<sub>2</sub>Cl

:[[File:Epichlorohydrin-manufacture-step1-2D-skeletal.png|300px]]

In the second step, this mixture is treated with base to give the [[epoxide]]:

:HOCH<sub>2</sub>CHClCH<sub>2</sub>Cl and, or ClCH<sub>2</sub>CH(OH)CH<sub>2</sub>Cl  +  NaOH   →  CH<sub>2</sub>CHOCH<sub>2</sub>Cl  +  NaCl  +  H<sub>2</sub>O

:[[File:Epichlorohydrin-manufacture-step2-2D-skeletal.png|443px]]

In this way, more than 700,000&nbsp;tons of epichlorohydrin are produced annually.<ref>Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl compounds” in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. Published online: 15 June 2000.</ref>

==Applications==
===Glycerol and epoxy resins synthesis===
Epichlorohydrin is mainly converted to [[Bisphenol A diglycidyl ether]], a building block in the manufacture of [[epoxy resin]]s. 
It is also a precursor to monomers for other resins and polymers.

Another usage is the conversion to synthetic [[glycerol]]:
:CH<sub>2</sub>CHOCH<sub>2</sub>Cl  +  2 H<sub>2</sub>O  →  HOCH<sub>2</sub>CH(OH)CH<sub>2</sub>(OH)  +  HCl

However, the rapid increase in biodiesel production has led to a glut of glycerol on the market, rendering this process uneconomic. In fact, ways to perform the reverse process are now being researched, to produce epichlorohydrin from the now less valuable glycerol, a process now commercialised by Solvay SA with a commercial demo site producing 10 000 tons annually.

===Minor and niche applications===
Epichlorohydrin is a versatile precursor in the synthesis of many organic compounds.  For example, it is converted to [[glycidyl nitrate]], an energetic binder used in explosive and propellant compositions.<ref>Gould, R.F. '' Advanced Propellant Chemistry'', ACS Chemistry Series 54, 1966</ref> The epichlorohydrin is reacted with an alkali nitrate, such as sodium nitrate, producing glycidyl nitrate and alkali chloride.  It used as a solvent for [[cellulose]], resins and paints and it has found use as an insect fumigant.{{Citation needed|date=February 2009}}

Epichlorohydrin is used in paper reinforcement (used for instance in the food industry to manufacture [[tea]] bags, [[coffee]] filters, and sausage/salami casings) and [[water purification]].<ref>http://www.chemicalsubstanceschimiques.gc.ca/challenge-defi/batch-lot-2/106-89-8_e.html</ref>

An important biochemical application of epichlorohydrin is its use as crosslinking agent for the production of Sephadex size-exclusion chromatographic resins from dextrans <ref>http://www5.gelifesciences.com/aptrix/upp00919.nsf/content/EE755AF81C96972FC1256EB40048417B?OpenDocument&Path=Catalog&Hometitle=Catalog&entry=1&newrel&LinkParent=C1256FC4003AED40-342B143523C3C764C12570F600421582_RelatedLinksNew-C821BEC677D8448BC1256EAE002E3030&newrel&hidesearchbox=yes&moduleid=166703</ref>

==Safety==
Epichlorohydrin is irritating and moderately toxic as well as [[carcinogenic]].<ref name="EPA"/>

==See also==
* [[Epoxy resins]]

==References==
<references/>

[[Category:Organochlorides]]
[[Category:Solvents]]
[[Category:IARC Group 2A carcinogens]]
[[Category:Oxiranes]]

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