Utente:Grasso Luigi/sanbox1/Esacloroetano
| Esacloroetano | |
|---|---|
 | |
  | |
| Nome IUPAC | |
| Esacloroetano | |
| Caratteristiche generali | |
| Formula bruta o molecolare | C2Cl6 |
| Massa molecolare (u) | 236,74 |
| Aspetto | solido cristallino incolore |
| Numero CAS | |
| SMILES | ClC(Cl)(Cl)C(Cl)(Cl)Cl |
| Proprietà chimico-fisiche | |
| Densità (g/cm3, in c.s.) | 2,091 a 20 °C |
| Solubilità in acqua | 50 mg/L a 20 °C |
| Coefficiente di ripartizione 1-ottanolo/acqua | 4,14 |
| Tensione di vapore (Pa) a 293,15 K | 53,33 |
| Proprietà tossicologiche | |
| DL50 (mg/kg) | 4460 mg/kg, ratto, per os 4970 mg/kg Cavia porcellus per os |
| Indicazioni di sicurezza | |
| Simboli di rischio chimico | |
  
| |
| attenzione | |
| Frasi H | 315 - 319 - 335 - 351 - 410 |
| Consigli P | 261 - 273 - 281 - 305+351+338 - 501 [1] |
L'esacloroetano è un alogenuro alchilico di formula Cl3C-CCl3, strutturalmente considerabile come una molecola di etano H3C-CH3 dove tutti i sei atomi di idrogeno sono stati sostituiti con altrettanti atomi di cloro. In condizioni standard appare come un solido cristallino incolore e dall'odore caratteristico, simile a quello della canfora. Poco solubile in acqua, risulta invece ben miscibile nei comuni solventi polari come etanolo, benzene, cloroformio, dietiletere, tetracloroetilene ed oli in generale[2].
Sintesi
[modifica | modifica wikitesto]Chlorination of tetrachloroethylene at 100–140°C with the presence of ferric chloride is the most commonly used commercial production method, however several other methods exist. A high purity form can be produced in a small scale by reacting chlorine together with barium carbide.[3]101 In September 1997, it was reported as no longer being produced in the United States for commercial distribution, but was produced as a by-product of industrial chlorination process.[3]101
Applicazioni
[modifica | modifica wikitesto]Hexachloroethane has been used in the formulation of extreme pressure lubricants. It has also been used as a chain transfer agent in the emulsion polymerization of propylene tetrafluoroethylene copolymer. Hexachloroethane has been used as an anthelmintic in veterinary medicine, a rubber accelerator, a component of fungicidal and insecticidal formulations as well as a moth repellant and a plasticizer for cellulose esters.[4]
Hexachloroethane has been used in the manufacture of degassing pellets to remove hydrogen gas bubbles from molten aluminum in aluminum foundries. This use, as well as similar uses in magnesium, is being phased out in the European Union.[5]
Use as smoke agent
[modifica | modifica wikitesto]Smoke grenades, called hexachloroethane (HCE) smoke or HC smoke, utilize a mixture containing roughly equal parts of HCE and zinc oxide and approximately 6% granular aluminium. These smokes are toxic, which is attributed to the production of zinc chloride (ZnCl2).[6][7] According to Steinritz et al., "Due to its potential pulmonary toxicity," zinc chloride producing smoke grenades "have been discharged from the armory of most western countries (...)."[8]
Tossicità
[modifica | modifica wikitesto]Hexachlorethane is not particularly toxic when taken orally,[9] but is considered to be quite toxic by skin adsorption. The primary effect is depression of the central nervous system.[4] The IDLH is given as 300 ppm and the OSHA PEL is 1 ppm (skin).[9] It is reasonably anticipated to be a carcinogen.[10]
Cloroetani
[modifica | modifica wikitesto]Riportiamo i 6 cloroetani e i loro 3 isomeri di struttura
| Formula struttura | Nomenclatura | Isomero posizione |
|---|---|---|
| CH3CH2Cl | Cloroetano | |
| CH3CHCl2 | 1,1-dicloroetano (cloruro di etilidene) | |
| CH2ClCH2Cl | 1,2-dicloroetano (dicloruro di etilene) | Si |
| CH3CCl3 | 1,1,1-tricloroetano (cloroformio di metile) | |
| CHCl2CH2Cl | 1,1,2-tricloroetano (tricloruro di vinile) | Si |
| CH2ClCCl3 | 1,1,1,2-tetracloroetano (R-130a) | |
| CHCl2CHCl2 | 1,1,2,2-tetracloroetano (R-130) | Si |
| CHCl2CCl3 | Pentacloroetano | |
| CCl3CCl3 | Esacloroetano |
Note
[modifica | modifica wikitesto]- ^ Esacloroetano - scheda di dati di sicurezza (PDF), su sigma-aldrich.com, Sigma-Aldrich. URL consultato il 17 novembre 2016.
- ^ (EN) Hexachloroethane, su Hazardous Substances Data Bank, National Institutes of Health. URL consultato il 17 novembre 2016.
- ^ a b HEXACHLOROETHANE 101 (PDF), su atsdr.cdc.gov, September 1997.
- ^ a b Errore nelle note: Errore nell'uso del marcatore
<ref>: non è stato indicato alcun testo per il marcatoreKirk-Othmer - ^ ECHA, Annex XVII to REACH – Conditions of restriction, Restrictions on the manufacture, placing on the market and use of certain dangerous substances, mixtures and articles, entry 41: hexachloroethane
- ^ Appendix E: Smoke And Masking Agents (PDF), su dva.gov.au, Australian Department of Veteran Affairs, December 2003.
- ^ National Research Council (1997). Toxicity of Military Smokes and Obscurants, volume 1. Subcommittee on Military Smokes and Obscurants. Washington, DC: National Academy Press. p. 127
- ^ Steinritz, D., Zehfuß, F., Stenger, B., Schmidt, A., Popp, T., Kehe, K., Mückter, H., Thiermann, H., Gudermann, T. (2018). Zinc chloride-induced TRPA1 activation does not contribute to toxicity in vitro. Toxicology Letters, 293, 133–139. doi:10.1016/j.toxlet.2017.09.008
- ^ a b Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) Hexachloroethane, su cdc.gov, NIOSH, May 1994.
- ^ Report on Carcinogens, Twelfth Edition, Hexachloroethane (PDF), su ntp.niehs.nih.gov, NIH, 2011.
Altri progetti
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