Hexachlorcyclopentadien

Bezeichnung:Hexachlorcyclopentadien

CAS-Nr77-47-4

Englisch Name:Hexachlorocyclopentadiene

CBNumberCB3432075

SummenformelC5Cl6

Molgewicht272.77

MOL-Datei77-47-4.mol

Synonyma

Hexachlorcyclopentadien

1,2,3,4,5,5-Hexachlor-1,3-cyclopentadien

Perchlorcyclopentadien

Hexachlorcyclopentadien physikalisch-chemischer Eigenschaften

Schmelzpunkt	−10 °C(lit.)
Siedepunkt	239 °C753 mm Hg(lit.)
Dichte	1.702 g/mL at 25 °C(lit.)
Dampfdruck	0.13 psi ( 20 °C)
Brechungsindex	n20/D 1.5644(lit.)
Flammpunkt	109 °C
storage temp.	2-8°C
Löslichkeit	Chloroform (Sparingly), Ethyl Acetate (Slightly)
Aggregatzustand	Yellow to amber-colored liquid
Farbe	Colourless to Pale Yellow
Wasserlöslichkeit	805ug/L(22.5 ºC)
Henry's Law Constant	1.64(x 10^-2 atm?m³/mol) at 25 °C (gas stripping-GC, Warner et al., 1987) 1.6(x 10^-2 atm?m³/mol) (Pankow and Rosen, 1988)
Expositionsgrenzwerte	NIOSH REL: 10 ppb (100 mg/m³); ACGIH TLV: TWA 0.01 ppm (adopted), 0.002 mg/m³ ppm (skin).
Dielectric constant	2.9100000000000001
Stabilität	Stability Stable, but light-sensitive. Non-flammable. Very reactive with alkenes and polynuclear hydrocarbons. Explosive with sodium. Incompatible with strong oxidizing agents, most common metals.
CAS Datenbank	77-47-4(CAS DataBase Reference)
NIST chemische Informationen	1,3-Cyclopentadiene, 1,2,3,4,5,5-hexachloro-(77-47-4)
EPA chemische Informationen	Hexachlorocyclopentadiene (77-47-4)

Sicherheit

Kennzeichnung gefährlicher	T+,N,T,F
R-Sätze:	22-24-26-34-50/53-39/23/24/25-23/24/25-52/53-11
S-Sätze:	23-39-45-61-60-53-25-36/37-16
RIDADR	UN 2646 6.1/PG 1
OEB	D
OEL	TWA: 0.01 ppm (0.1 mg/m3)
WGK Germany	3
RTECS-Nr.	GY1225000
F	10-23
HazardClass	6.1(a)
PackingGroup	I
Giftige Stoffe Daten	77-47-4(Hazardous Substances Data)
Toxizität	Drinking water standard (final): MCLG: 50 μg/L:MCL: 50 μg/L. In addition, a DWEL of 200 μg/L was recommended (U.S. EPA, 2000).

Gefahreninformationscode (GHS)

Hexachlorocyclopentadiene Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
öLIGE, GELBE BIS GRüNE FLüSSIGKEIT MIT STECHENDEM GERUCH.
PHYSIKALISCHE GEFAHREN
Die Dämpfe sind schwerer als Luft.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen unter Bildung giftiger und ätzender Rauche mit Chlorwasserstoff und Phosgen. Reagiert mit feuchter Luft unter Bildung von Chlorwasserstoff (s. ICSC-Nr. 0163). Greift viele Metalle in Gegenwart von Wasser unter Bildung brennbarer/explosionsfähiger Gase an (z.B. Wasserstoff, ICSC-Nr. 0001).
ARBEITSPLATZGRENZWERTE
TLV: 0.01 ppm (als TWA); Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK: IIb (nicht festgelegt, aber Informationen vorhanden); Hautresorption; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C kann schnell eine gesundheitsschädliche Kontamination der Luft eintreten.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz verätzt die Augen, die Haut und die Atemwege. ätzend beim Verschlucken. Inhalation der Substanz kann zu Lungenödem führen (s. Anm.). Möglich sind Auswirkungen auf Nieren und Leber mit nachfolgenden Gewebeschäden. Die Auswirkungen treten u.U. verzögert ein. ärztliche Beobachtung notwendig.
LECKAGE
Persönliche Schutzausrüstung: Chemikalienschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät. NICHT in die Umwelt gelangen lassen. Ausgelaufene Flüssigkeit in abdichtbaren Kunststoffbehältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen.
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R24:Giftig bei Berührung mit der Haut.
R26:Sehr giftig beim Einatmen.
R34:Verursacht Verätzungen.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R11:Leichtentzündlich.
S-Sätze Betriebsanweisung:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S39:Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S60:Dieses Produkt und sein Behälter sind als gefährlicher Abfall zu entsorgen.
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S25:Berührung mit den Augen vermeiden.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
Beschreibung
Hexachlorocyclopentadiene is a pale-yellow/lemon-yellow liquid with a characteristic musty or pungent odour (odour threshold – 0.03 ppm). Hexachlorocyclopentadiene does not occur naturally but is a manufactured chemical. It easily evaporates into the air. Hexachlorocyclopentadiene is the key intermediate in the manufacture of some pesticides, including heptachlor, chlordane, aldrin, dieldrin, and endrin. Hexachlorocyclopentadiene is also used in the manufacture of flame retardants and some resins, shock-proof plastics, fluorocarbons, and dyes. Hexachlorocyclopentadiene quickly breaks down by sunlight and reacts with other chemicals in the air.
Chemische Eigenschaften
Hexachlorocyclopentadiene is a pale-yellow to amber-colored, oily liquid. Pungent, unpleasant odor. The odor threshold is 0.15 0.33 ppm. Insoluble in water, soluble in ether, carbon tetrachloride and other organic solvents.
Verwenden
Hexachlorocyclopentadiene is an organochlorine compound that is used to manufacturing organochlorine insecticides and acaricides, such as mirex, aldrin, dieldrin, chlordane, endosulfan, etc. It is also used to make flame retardants, resins that won't burn, shock-proof plastics, esters, ketones, fluorocarbons, and dyes.
synthetische
Hexachlorocyclopentadiene is obtained by chlorination of cyclopentadiene in two steps. In addition, using petroleum pentane as raw material, hexachlorocyclopentadiene is synthesized by photochlorination and high temperature chlorination, and the yield is about 70%.
Application
Hexachlorocyclopentadiene(Hex) is an Intermediate in the manufacture of chlorinated pesticides and flame retardants. The principal end use for Hex is as a key intermediate in the production of chlorinated cyclodiene pesticides, including aldrin, dieldrin, endrin, chlordane, heptachlor, kepone, endosulfan, pentac, isodrin, and mirex. It is also used as an intermediate in the manufacture of flame retardants such as Dechlorane Plus and chlorendic anhydride and, to a lesser extent, in the manufacture of nonflammable resins, polyester resins, pharmaceuticals, unbreakable plastics, acids, esters, ketones, fluorocarbons, and dyes.
Allgemeine Beschreibung
A pale yellow liquid with a pungent odor. Density 14.3 lb /gal. Solidifies at 50°F. Insoluble in water. Noncombustible. Very toxic by skin absorption and inhalation. Corrosive to tissue.
Air & Water Reaktionen
Insoluble in water. Reacts slowly with water to form hydrochloric acid.
Reaktivität anzeigen
Hexachlorocyclopentadiene is incompatible with strong oxidizing and reducing agents. Also incompatible with many amines, nitrides, azo/diazo compounds, alkali metals (sodium), and epoxides.
Health Hazard
Hexachlorocyclopentadiene is very toxic and may be fatal if inhaled, swallowed, or absorbed through the skin. The probable human lethal dose is 50-500 mg/kg, or between 1 teaspoon and 1 ounce for a 150 lb. (70 kg) person. Severe exposure induces pulmonary hyperemia and edema, degenerative and necrotic changes in brain, heart and adrenal glands and necrosis of liver and kidney tubules. Questionable carcinogen.
Brandgefahr
Toxic hydrogen chloride, chlorine, and phosgene gases may form in fires. In presence of moisture, will corrode iron and other materials; flammable and explosive hydrogen gas may collect in enclosed space. Will corrode iron and other metals in the presence of moisture. Reacts slowly with water to form hydrochloric acid; however, the reaction is not hazardous. Hazardous polymerization may not occur.
Sicherheit(Safety)
Hexachlorocyclopentadiene is a manufactured chemical that does not occur naturally. Hex has no end uses of its own, and is very toxic following acute (short-term) oral and inhalation exposures. It easily evaporates into the air; the vapor looks like a blue haze. Most of the Hexachlorocyclopentadiene in the environment results from its release during production and disposal. Animal tests suggest that very high levels can cause death. Human data are limited, but it can cause headaches and irritate the nose, throat, eye, and skin.
mögliche Exposition
Hexachlorocyclopentadiene is used to produce the flame retardant chlorendic anhydride, which has applications in polyesters; and to produce chlorendic anhydride and chlorendic acid; which is used as a flame retardant in resins. Hexachlorocyclopentadiene is also used as an intermediate in the production of pesticides, such as aldrin, dieldrin, and endosulfan.
Erste Hilfe
If this chemical gets into the eyes, remove any con-tact lenses at once and irrigate immediately for at least 15 min,occasionally lifting upper and lower lids. Seek medical atten-tion immediately. If this chemical contacts the skin, removecontaminated clothing and wash immediately with soap andwater. Speed in removing material from the skin is of extremeimportance. Seek medical attention immediately. If this chem-ical has been inhaled, remove from exposure, begin rescuebreathing (using universal precautions, including resuscitationmask) if breathing has stopped and CPR if heart action hasstopped. Transfer promptly to a medical facility. When thischemical has been swallowed, get medical attention. Givelarge quantities of water and induce vomiting. Do not make anunconscious person vomit. Keep victim quiet and maintainnormalbody temperature. Medical observation is recom-mended for 24- 48 h after breathing overexposure, as pulmo-nary edema may be delayed. As first aid for pulmonaryedema, a doctor or authorized paramedic may consider admin-istering a corticosteroid spray.
Environmental Fate
Biological. When hexachlorocyclopentadiene (5 and 10 mg/L) was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum for 7 d, 100% biodegradation with rapid adaptation was observed (Tabak et al., 1981). In a model ecosystem containing plankton, Daphnia magna, mosquito larva (Culex pipiens quinquefasciatus), fish (Cambusia affinis), alga (Oedogonium cardiacum), and snail (Physa sp.), hexachlorocyclopentadiene degraded slightly, but no products were identified (Lu et al., 1975).
Photolytic. The major photolysis and hydrolysis products identified in distilled water were pentachlorocyclopentenone and hexachlorocyclopentenone. In mineralized water, the products identified include cis- and trans-pentachlorobutadiene, tetrachlorobutenyne, and pentachloropentadienoic acid (Chou and Griffin, 1983). In a similar experiment, irradiation of hexachlorocyclopentadiene in water by mercury-vapor lamps resulted in the formation of 2,3,4,4,5- pentachloro-2-cyclopentenone. This compound hydrolyzed partially to hexachloroindenone (Butz et al., 1982). Other photodegradation products identified include hexachloro-2-cyclopentenone and hexachloro-3-cyclopentenone as major products. Secondary photodegradation products reported include pentachloro-cis-2,4-pentadienoic acid, Z- and E-pentachlorobutadiene, and tetrachlorobutyne (Chou et al., 1987). In natural surface waters, direct photolysis of hexachlorobutadiene via sunlight results in a half-life of 10.7 min (Wolfe et al., 1982).
Chemical/Physical. Slowly reacts with water forming HCl and 1,1-dihydroxytetrachlorocyclopentadiene (Kollig, 1993; NIOSH, 1997). The diene is unstable forming polymers (Kollig, 1993).
Solubility in organics
Based on structurally similar compounds, hexachlorocyclopentadiene is expected to be soluble in benzene, ethanol, chloroform, methylene chloride, trichloroethylene, and other liquid halogenated solvents.
Lager
Color Code- -Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, well-venti latedarea away from water. Protect containers fromphysical damage. In the presence of moisture, hexachloro-cyclopentadiene will corrode iron and other metals.
Versand/Shipping
UN2646 Hexachlorocyclopentadiene, Hazard Class: 6.1; Labels: 6.1-Poison Inhalation Hazard, Inhalation Hazard Zone B.
läuterung methode
Dry the diene with MgSO4, filter, and distil it under vacuum in a nitrogen atmosphere. Irritates skin and eyes, HIGHLY TOXIC. [McBee et al. J Am Chem Soc 77 4378 1955, UV spectra: Idol et al. J Org Chem 20 1746 1955, Beilstein 5 III 308, 5 IV 381.]
Toxicity evaluation
Hex’s mechanism of toxicity is incompletely understood. Because of its characteristics as a chlorinated hydrocarbon, it would be expected to induce drug-metabolizing enzymes in the liver.
Inkompatibilitäten
Reacts slowly with water to form hydro chloric acid; will corrode iron and most metals in presence of moisture. Explosive hydrogen gas may collect in enclosed spaces in the presence of moisture. Contact with sodium may be explosive.
Waste disposal
Incineration after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids pro duced. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must con form to EPA regulations governing storage, transportation, treatment, and waste disposal.

Hexachlorocyclopentadiene Upstream-Materialien And Downstream Produkte

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