Epichlorohydrin is an organochlorine compound An organochloride, organochlorine, chlorocarbon, 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 compounds on the 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 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 division between "organic" and " solvents The most common solvent in everyday life is water. Most other commonly-used solvents are organic chemicals. These are called organic solvents. Solvents usually have a low boiling point and evaporate easily or can be removed by distillation, leaving the dissolved substance behind. To distinguish between solutes and solvents, solvents are usually.[2] Epichlorohydrin is a highly reactive compound and is used in the production of glycerol Glycerol is an organic compound, also commonly called glycerin or glycerine. It is a colorless, odorless, 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, plastics, epoxy glues 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 elasticity. 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 which link to form the polymer is usually made of carbon, hydrogen, oxygen and/or silicon. Elastomers. In contact with water, epichlorohydrin hydrolyzes to 3-MCPD 3-MCPD or 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 the exacerbation of cancer or in the increase of its propagation. 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 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 . HOCl 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 glycerol Glycerol is an organic compound, also commonly called glycerin or glycerine. It is a colorless, odorless, 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:
- CH2CHOCH2Cl + 2 H2O → HOCH2CH(OH)CH2(OH) + HCl
It is also 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, for example by alkylation of bisphenol-A Bisphenol A, commonly abbreviated as BPA, is an organic compound with two phenol functional groups. It is a difunctional building block of several important plastics and plastic additives. With an annual production of 2–3 million tonnes, it is an important monomer in the production of polycarbonate. It is a precursor to monomers for other resins and polymers.
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 coffee, for example, 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]
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 the exacerbation of cancer or in the increase of its propagation. 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.[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
Categories: Epoxides | Organochlorides | Solvents | IARC Group 2A carcinogens
Market Research Agency
Mcgroup Global demand for epichlorohydrin and its derivatives exceeds offer. According to UK-based market research firm Merchant Research & Consulting Ltd., ...
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