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14-September-2008 18:38:37 - Acetonitrile Acetonitrile IUPAC name Ethanenitrile Other names Methyl cyanide; cyanomethane Identifiers CAS number 75-05-8 RTECS number AL7700000 SMILES CC#N InChI 1/C2H3N/c1-2-3/h1H3 Properties Molecular formula C2H3N Isomers 41.052038 g/mol Appearance colorless liquid Density 0.786 g/mL liquid Melting point -45 °C Boiling point 82 °C Solubility in water miscible Solubility organic solvents Acidity pKa 25 Hazards MSDS External MSDS EU classification Flammable, harmful NFPA 704 3 2 0 R-phrases R11, R20/21/22, R36 S-phrases S1/2, S16, S36/37 Flash point 2 °C Related compounds Related nitriles propionitrile, butyronitrile Related compounds acetic acid, acetamide, ethylamine Supplementary data page Structure and properties n, εr, etc. Thermodynamic data Phase behaviour Solid, liquid, gas Spectral data UV, IR, NMR, MS Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Acetonitrile ACN is the chemical compound with formula CH3CN. This colourless liquid is the simplest organic nitrile and is widely used as a solvent. Contents 1 Production 2 Applications 2.1 Solvent 2.2 Laboratory uses 2.2.1 Organic synthesis 2.2.2 Ligand in inorganic chemistry 3 Safety 3.1 Toxicity 3.1.1 Metabolism and excretion 4 References 5 External links Production Acetonitrile is a by-product from the manufacture of acrylonitrile.1 Production trends for acetonitrile thus generally follow those of acrylonitrile. Acetonitrile can also be produced by many other methods, but these are of no commercial importance as of 2002. Illustrative routes are by dehydration of acetamide or by hydrogenation of mixtures of carbon monoxide and ammonia.2 The four main producers of acetonitrile in the United States are: INEOS, DuPont, J.T. Baker Chemical, and Sterling Chemicals. In 1992update, 32.3 million pounds 14,700 t of acetonitrile were produced in the US. Applications Solvent Acetonitrile is a polar solvent, with a dipole moment of 3.84 D, miscible with water and with a convenient liquid range. It has been used in formulations for nail polish remover, despite its low but significant toxicity.3 Acetone and ethyl acetate are often preferred as safer for domestic use, and acetonitrile has been banned in cosmetic products in the European Economic Area since March 2000.4 Acetonitrile dissolves a wide range of compounds without complications, due to its low acidity. Its low viscosity and low chemical reactivity make it a popular choice for liquid chromatography. Similarly, it is a popular solvent in cyclic voltammetry because of its relatively high dielectric constant. Industrially, it is used a solvent in the purification of butadiene and in the manufacture of pharmaceuticals and photographic film.5 Laboratory uses Organic synthesis Acetonitrile is a two-carbon building block in organic synthesis6 as in the production of pesticides to perfumes. Its reaction with cyanogen chloride affords malononitrile. Ligand in inorganic chemistry In inorganic chemistry, acetonitrile is employed as a displaceable ligand. For example, PdCl2MeCN2 is prepared by heating a suspension of polymeric palladium chloride in acetonitrile: PdCl2 + 2 MeCN → PdCl2MeCN2 Safety Toxicity Acetonitrile itself has only a modest toxicity,7 but it can be metabolised to produce hydrogen cyanide see below, which is the source of the observed toxic effects.589 Cases of acetonitrile poisoning in humans or, more strictly, of cyanide poisoning after exposure to acetonitrile are rare but not unknown, by inhalation, ingestion and possibly by skin absorption.8 The symptoms, which do do not usually appear for several hours after the exposure, include breathing difficulties, slow pulse rate, nausea and vomiting: convulsions and coma can occur in serious cases, followed by death from respiratory failure. The treatment is as for cyanide poisoning, with oxygen, sodium nitrite and sodium thiosulfate among the most commonly used remedies.8 Metabolism and excretion Compound Brain cyanide concentration µg/kg Oral LD50 mg/kg Acetonitrile 28±5 2460 Propionitrile 508±84 40 Butyronitrile 437±106 50 Malononitrile 649±209 60 Acrylonitrile 395±106 90 Potassium cyanide 748±200 10 Ionic cyanide concentrations measured in the brains of Sprague-Dawley rats one hour after oral administration of an LD50 of various nitriles.10 In common with other nitriles, acetonitrile can be metabolised in microsomes, especially in the liver, to produce hydrogen cyanide, as was first shown by Pozzani et al. in 1959.11 The first step in this pathway is the oxidation of acetonitrile to glyconitrile by an NADPH-dependent cytochrome P450 monooxygenase. The glyconitrile then undergoes a spontaneous decondensation to give hydrogen cyanide and formaldehyde.78 The metabolism of acetonitrile is much slower than that of other nitriles, which accounts for its relatively low toxicity. Hence, one hour after receiving a potentially lethal dose, the concentration of cyanide in the brain is 20-times lower for acetonitrile poisoning than for propionitrile poisoning, despite the fact that the administered dose was 60-times higher see table.10 The relatively slow metabolism of acetonitrile to hydrogen cyanide allows more of the cyanide produced to be detoxified within the body to thiocyanate the rhodanese pathway. It also allows more of the acetonitrile to be excreted unchanged before it is metabolised. The main pathways of excretion are by exhalation and in the urine.789 References ^ Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke Nitriles in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002: Weinheim. DOI: 10.1002/14356007.a17_363 ^ US patent 4179462, Process for preparing acetonitrile, granted , assigned to Monsanto ^ At least two cases have been reported of accidental poisoning of young children by acetonitrile-based nail polish remover, one of which was fatal: Caravati, EM; Litovitz, T 1988. Pediatric cyanide intoxication and death from an acetonitrile-containing cosmetic. J. Am. Med. Assoc. 260 23: 3470-73. PMID 3062198. ^ Twenty-Fifth Commission Directive 2000/11/EC of 10 March 2000 adapting to technical progress Annex II to Council Directive 76/768/EEC on the approximation of laws of the Member States relating to cosmetic products. OJEC L65 of 2000-03-14, pp. 22-25. ^ a b Spanish Ministry of Health 2002, Acetonitrile. Summary Risk Assessment Report, Ispra VA, Italy: European Chemicals Bureau, Special Publication I.01.65, http://ecb.jrc.it/DOCUMENTS/Existing-Chemicals/RISK_ASSESSMENT/SUMMARY/acetonitrilesum006.pdf ^ DiBiase, S. A.; Beadle, J. R.; Gokel, G. W.. Synthesis of α,β-Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile. Org. Synth.; Coll. Vol. 7: 108. ^ a b c Institut National de Recherche et de Sécurité INRS 2004, Fiche toxicologique nº 104 : Acétonitrile, Paris: INRS, ISBN 2-7389-1278-8, http://www.inrs.fr/inrs-pub/inrs01.nsf/IntranetObject-accesParReference/FT%20104/$File/ft104.pdf ^ a b c d e International Programme on Chemical Safety 1993, Environmental Health Criteria 154. Acetonitrile, Geneva: World Health Organization, http://www.inchem.org/documents/ehc/ehc/ehc154.htm ^ a b Greenberg, Mark 1999, Toxicological Review of Acetonitrile, Washington, D.C.: U.S. Environmental Protection Agency, http://www.epa.gov/NCEA/iris/toxreviews/0205-tr.pdf ^ a b Ahmed, AE; Farooqui, MYH 1982. Comparative toxicities of aliphatic nitriles. Toxicol. Lett. 12: 157-64. doi:doi:10.1016/0378-42748290179-5. ^ Pozzani, UC; Carpenter, CP; Palm, PE; Weil, CS; Nair, JH 1959. An investigation of the mammalian toxicity of acetonitrile. J. Occup. Med. 1: 634-642. External links WebBook page for C2H3N International Chemical Safety Card 0088 National Pollutant Inventory - Acetonitrile fact sheet NIOSH Pocket Guide to Chemical Hazards Retrieved from http://en..org/wiki/Acetonitrile Categories: Hazardous air pollutants | Nitriles | SolventsHidden categories: Articles containing potentially dated statements from 1992 | All articles containing potentially dated statements Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français Italiano Nederlands 日本語 Polski РуÑ?Ñ?кий Suomi Svenska ä¸æ–‡ Türkçe This page was last modified on 4 September 2008, at 18
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