Epichlorohydrin is an organochlorine compound and an epoxide

Epoxide

An epoxide is a cyclic ether with three ring atoms. This ring approximately defines an equilateral triangle, which makes it highly strained. The strained ring makes epoxides more reactive than other ethers. Simple epoxides are named from the parent compound ethylene oxide or oxirane, such as in...

. This is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible

Miscibility

Miscibility is the property of liquids to mix in all proportions, forming a homogeneous solution. In principle, the term applies also to other phases , but the main focus is usually on the solubility of one liquid in another...

 with most polar organic

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 solvent

Solvent

A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

s. Epichlorohydrin is a highly reactive compound and is used in the production of glycerol

Glycerol

Glycerol is a simple polyol compound. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol backbone is central to all lipids...

, plastics, epoxy glues and resins, and elastomer

Elastomer

An elastomer is a polymer with the property of viscoelasticity , generally having notably low Young's modulus and high yield strain compared with other materials. The term, which is derived from elastic polymer, is often used interchangeably with the term rubber, although the latter is preferred...

s. In contact with water, epichlorohydrin hydrolyzes to 3-MCPD

3-MCPD

3-MCPD or is an organic chemical compound which is carcinogenic and highly suspected to be genotoxic in humans, has male anti-fertility effects, and is a chemical byproduct which may be formed in foods, the most commonly found member of chemical contaminants known as chloropropanols.It is...

, a carcinogen

Carcinogen

A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...

 found in food.
Epichlorohydrin is manufactured from allyl chloride

Allyl chloride

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene.-Production:Allyl...

 in two steps, beginning with the hydrochlorination using hypochlorous acid

Hypochlorous acid

Hypochlorous acid is a weak acid with the chemical formula HClO. It forms when chlorine dissolves in water. It cannot be isolated in pure form due to rapid equilibration with its precursor...

, which affords a mixture of two alcohols:

CH₂=CHCH₂Cl + HOCl → HOCH₂CHClCH₂Cl and, or ClCH₂CH(OH)CH₂Cl

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

Epoxide

An epoxide is a cyclic ether with three ring atoms. This ring approximately defines an equilateral triangle, which makes it highly strained. The strained ring makes epoxides more reactive than other ethers. Simple epoxides are named from the parent compound ethylene oxide or oxirane, such as in...

:

HOCH₂CHClCH₂Cl and, or ClCH₂CH(OH)CH₂Cl + NaOH → CH₂CHOCH₂Cl + NaCl + H₂O

In this way, more than 700,000 tons of epichlorohydrin are produced annually.
Epichlorohydrin is mainly converted to Bisphenol A diglycidyl ether

Bisphenol A diglycidyl ether

Bisphenol A diglycidyl ether is a chemical compound used as constituent of epoxy resins. It is a derivative of bisphenol A that is used in epoxy resins for its cross-linking properties....

, a building block in the manufacture of epoxy resins.