Epichlorohydrin is an organochlorine compound An organochloride, organochlorine, chlorocarbon, chlorinated hydrocarbon, or chlorinated solvent is an organic compound containing at least one covalently bonded chlorine atom. Their wide structural variety and divergent chemical properties lead to a broad range of applications. Many derivatives are controversial because of the effects of these and an 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 chloromethyloxirane. As a functional group epoxides. This is a colorless liquid with a pungent, garlic-like odor, insoluble in water, but miscible In chemistry, 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. Water and ethanol, for example, are miscible since they mix in all proportions with most polar In chemistry, polarity refers to a separation of electric charge leading to a molecule having an electric dipole. Polar molecules can bond together due to dipole–dipole intermolecular forces between one molecule with asymmetrical charge distribution and another molecule also with asymmetrical charge distribution. Molecular polarity is dependent organic An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered inorganic. The distinction between "organic" and " solvents 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. Common uses for organic solvents are in dry cleaning (e.g. tetrachloroethylene), as a paint thinner (e.g. toluene, turpentine), as nail polish removers and.[2] Epichlorohydrin is a highly reactive compound and is used in the production of glycerol Glycerol is an organic compound, also called glycerin or glycerine. It is a colourless, odourless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydrophilic hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol substructure is a central component of many, plastics, epoxy glues Epoxy or polyepoxide is a thermosetting polymer formed from reaction of an epoxide "resin" with polyamine "hardener". Epoxy has a wide range of applications, including fiber-reinforced plastic materials and general purpose adhesives and resins Epoxy or polyepoxide is a thermosetting polymer formed from reaction of an epoxide "resin" with polyamine "hardener". Epoxy has a wide range of applications, including fiber-reinforced plastic materials and general purpose adhesives, and elastomers 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 when referring to vulcanisates. Each of the monomers. In contact with water, epichlorohydrin hydrolyzes to 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, a 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. Several radioactive substances are considered carcinogens, but their carcinogenic activity is attributed to the radiation, for found in food.
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Production
Epichlorohydrin is manufactured from allyl chloride Allyl chloride is the organic compound with the formula C in two steps, beginning with the hydrochlorination using hypochlorous acid Hypochlorous acid is a weak acid with the chemical formula HClO. In the swimming pool industry, hypochlorous acid is referred to as HOCl. It forms when chlorine dissolves in water. It cannot be isolated in pure form due to rapid equilibration with its precursor . HClO is used as a bleach, an oxidizer, a deodorant, and a disinfectant, 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 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 chloromethyloxirane. As a functional group epoxides:
- 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 Bisphenol A diglycidyl ether is a chemical compound used as constituent of epoxy resins. It can be considered as a derivative of bisphenol A, and is used in epoxy resins for its cross-linking properties, a building block in the manufacture of epoxy resins Epoxy or polyepoxide is a thermosetting polymer formed from reaction of an epoxide "resin" with polyamine "hardener". Epoxy has a wide range of applications, including fiber-reinforced plastic materials and general purpose adhesives. It is also a precursor to monomers for other resins and polymers.
Another usage is the conversion to synthetic glycerol Glycerol is an organic compound, also called glycerin or glycerine. It is a colourless, odourless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydrophilic hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol substructure is a central component of many:
- 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 Cellulose is an organic compound with the formula n, a polysaccharide consisting of a linear chain of several hundred to over ten thousand β(1→4) linked D-glucose units, 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 Tea is the agricultural product of the leaves, leaf buds, and internodes of the Camellia sinensis plant, prepared and cured by various methods. "Tea" also refers to the aromatic beverage prepared from the cured leaves by combination with hot or boiling water, and is the common name for the Camellia sinensis plant itself bags, coffee Coffee is a brewed drink prepared from roasted seeds, commonly called coffee beans, of the coffee plant. They are seeds of coffee cherries that grow on trees in over 70 countries. Green unroasted coffee is one of the most traded agricultural commodities in the world. Due to its caffeine content, coffee can have a stimulating effect in humans filters, and sausage/salami casings) and water purification Water purification is the process of removing undesirable chemicals, materials, and biological contaminants from raw water. The goal is to produce water fit for a specific purpose. Most water is purified for human consumption but water purification may also be designed for a variety of other purposes, including meeting the requirements of medical,.[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 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. Several radioactive substances are considered carcinogens, but their carcinogenic activity is attributed to the radiation, for.[2]
See also
References
- ^ Merck Index, 12th Edition, 3648.
- ^ a b 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
Categories: Organochlorides | Solvents | IARC Group 2A carcinogens | Oxiranes
Mon, 14 Jun 2010 19:09:30 GMT+00:00
PR-inside.com (press release) The product range includes Epoxy, Caustic Soda, Epichlorohydrin - Calcium Chloride, Hydrochloric Acid and Sodium Hypochlorite. ...
