Epichlorohydrin
| (±)-Epichlorohydrin[1] | |
|---|---|
| Epichlorohydrin | |
| Ball-and-stick model of the epichlorohydrin molecule | |
| chloromethyloxirane | |
| Other names epichlorohydrin 1-chloro-2,3-epoxypropane γ-chloropropylene oxide glycidyl chloride | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 106-89-8 
|
| PubChem | 7835 |
| ChemSpider | 7547 |
| SMILES | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C3H5ClO |
| Molar mass | 92.52 g/mol |
| Density | 1.1812 g/cm3 |
| Melting point |
-25.6 °C |
| Boiling point |
117.9 °C |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| MSDS | External MSDS |
| EU classification | Toxic T |
| NFPA 704 | |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Epichlorohydrin is an organochlorine compound and an epoxide. This is a colorless liquid with a pungent, garlic-like odor, insoluble in water, but miscible with most polar organic solvents.[2] Epichlorohydrin is a highly reactive compound and is used in the production of glycerol, plastics, epoxy glues and resins, and elastomers. In contact with water, epichlorohydrin hydrolyzes to 3-MCPD, a carcinogen found in food.
Contents
Production
Epichlorohydrin is manufactured from allyl chloride in two steps, beginning with the hydrochlorination using hypochlorous acid, which affords a mixture of two alcohols:[3]
- CH2=CHCH2Cl + HOCl → HOCH2CHClCH2Cl and, or ClCH2CH(OH)CH2Cl
In the second step, this mixture is treated with base to give the epoxide:
- HOCH2CHClCH2Cl and, or ClCH2CH(OH)CH2Cl + NaOH → CH2CHOCH2Cl + NaCl + H2O
In this way, more than 700,000 tons of epichlorohydrin are produced annually.[4]
Applications
Glycerol and epoxy resins synthesis
Epichlorohydrin is mainly converted to Bisphenol A diglycidyl ether, a building block in the manufacture of epoxy resins. It is also a precursor to monomers for other resins and polymers.
Another usage is the conversion to synthetic glycerol:
- CH2CHOCH2Cl + 2 H2O → HOCH2CH(OH)CH2(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.[5] 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]
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.[6]
An important biochemical application of epichlorohydrin is its use as crosslinking agent for the production of Sephadex size-exclusion chromatographic resins from dextrans [7]
Safety
Epichlorohydrin is irritating and moderately toxic as well as carcinogenic.[2]
See also
References
- ↑ Merck Index, 12th Edition, 3648.
- ↑ 2.0 2.1 EPA consumer factsheet
- ↑ Guenter Sienel, Robert Rieth, Kenneth T. Rowbottom "Epoxides" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
- ↑ 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.
- ↑ Gould, R.F. Advanced Propellant Chemistry, ACS Chemistry Series 54, 1966
- ↑ http://www.chemicalsubstanceschimiques.gc.ca/challenge-defi/batch-lot-2/106-89-8_e.html
- ↑ 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
cs:Epichlorohydrin de:Epichlorhydrin nl:Epichloorhydrine ja:エピクロロヒドリン pl:Epichlorohydryna sv:Epiklorhydrin zh:环氧氯丙烷
