Cyclohexanon

Bezeichnung:Cyclohexanon

CAS-Nr108-94-1

Englisch Name:Cyclohexanone

CBNumberCB8347660

SummenformelC6H10O

Molgewicht98.14

MOL-Datei108-94-1.mol

Synonyma

Cyclohexanon

Ketohexamethylen

Pimelinketon

Cyclohexanon physikalisch-chemischer Eigenschaften

Schmelzpunkt	-47 °C (lit.)
Siedepunkt	155 °C (lit.)
Dichte	0.947 g/mL at 25 °C (lit.)
Dampfdichte	3.4 (vs air)
Dampfdruck	3.4 mm Hg ( 20 °C)
Brechungsindex	n20/D 1.450(lit.)
FEMA	3909 \| CYCLOHEXANONE
Flammpunkt	116 °F
storage temp.	Store at +5°C to +30°C.
Löslichkeit	90g/l
pka	17(at 25℃)
Aggregatzustand	Liquid
Farbe	APHA: ≤10
Relative polarity	0.281
PH	7 (70g/l, H2O, 20℃)
Geruch (Odor)	Like peppermint and acetone.
Explosionsgrenze	1.1%, 100°F
Geruchsart	minty
Wasserlöslichkeit	150 g/L (10 ºC)
Merck	14,2726
JECFA Number	1100
BRN	385735
Henry's Law Constant	1.2 x 10^-5 atm?m³/mol at 25 °C (Hawthorne et al., 1985) 6.92 x 10^-5 atm?m³/mol at 60.00 °C, 10.7 at 70.00 °C, 16.4 at 80.00 °C (headspace-GC, Hovorka et al., 2002)
Expositionsgrenzwerte	TLV-TWA 100 mg/m³ (25 ppm) (ACGIH); IDLH 5000 ppm (NIOSH).
Dielectric constant	18.2（20℃）
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents.
LogP	0.86 at 25℃
CAS Datenbank	108-94-1(CAS DataBase Reference)
IARC	3 (Vol. 47, 71) 1999
NIST chemische Informationen	Cyclohexanone(108-94-1)
EPA chemische Informationen	Cyclohexanone (108-94-1)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	10-20-41-38-20/21/22
S-Sätze:	25-36/37/39-26
RIDADR	UN 1915 3/PG 3
WGK Germany	1
RTECS-Nr.	GW1050000
Selbstentzündungstemperatur	788 °F
TSCA	Yes
HS Code	2914 22 00
HazardClass	3
PackingGroup	III
Giftige Stoffe Daten	108-94-1(Hazardous Substances Data)
Toxizität	LD50 orally in rats: 1.62 ml/kg (Smyth)
IDLA	700 ppm

Gefahreninformationscode (GHS)

Cyclohexanone Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSE öLIGE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.
PHYSIKALISCHE GEFAHREN
Die Dämpfe sind schwerer als Luft. Fließen, Schütten o.ä. kann zu elektrostatischer Aufladung führen.
CHEMISCHE GEFAHREN
Reagiert mit starken Oxidationsmitteln wie Salpetersäure unter Feuer- und Explosionsgefahr.
ARBEITSPLATZGRENZWERTE
TLV: 20 ppm (als TWA); 50 ppm (als STEL); Hautresorption; Krebskategorie: A3; (ACGIH 2005).
EG Arbeitsplatz-Richtgrenzwerte: 10 ppm 40.8 mg/m?(als TWA); 20 ppm 81.6 mg/m?(als STEL); Hautresorption; (EU 2004).
MAK: Hautresorption; Krebserzeugend Kategorie 3B; (DFG 2008).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation der Dämpfe, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C tritt langsam eine gesundheitsschädliche Kontamination der Luft ein.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Flüsssigkeit und der Dampf reizen die Augen, die Haut und die Atemwege. Exposition weit oberhalb der Arbeitsplatzgrenzwerte kann Bewusstseinstrübung verursachen.
LECKAGE
Persönliche Schutzausrüstung: Atemschutzgerät mit Filter für organische Gase und Partikel entsprechend der Arbeitsplatzkonzentration des Stoffes. Chemikalienschutzanzug. Zündquellen entfernen. Belüftung. Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen.
R-Sätze Betriebsanweisung:
R10:Entzündlich.
R20:Gesundheitsschädlich beim Einatmen.
S-Sätze Betriebsanweisung:
S25:Berührung mit den Augen vermeiden.
Aussehen Eigenschaften
C6H10O; Pimelinketon, Cyclohexylketon. Farblose bis gelbliche Flüssigkeit mit entfernt pfefferminzartigem, Aceton-ähnlichem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich beim Einatmen. Kann zu Kopfschmerz, Schwindel bis zum Koma führen. Reizt die Augen und die Haut.
Nicht mit Salpetersäure in Berührung bringen. Entzündlich.
LD₅₀ (oral, Ratte): 1650 mg/kg.
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Dämpfe nicht einatmen.
Mit flüssigkeitsbindendem Material, z.B. Rench Rapid aufnehmen. Der Entsorgung zuführen. Nachreinigen
Pulver, Schaum.
Brennbar. Dämpfe schwerer als Luft. Mit Luft Bildung explosionsfähiger Gemische möglich.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 15 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft. Arzt hinzuziehen.
Nach Verschlucken: Reichlich Wasser trinken. Erbrechen wegen Aspirationsgefahr vermeiden. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleridung entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als halogenfreie, organische Lösemittelabfälle.
Beschreibung
Cyclohexanone, a colorless liquid is a cyclic ketone. It is an important building block for the synthesis of a variety of organic compounds. Majority of the cyclohexanone synthesized is utilized as an intermediate in the synthesis of nylon.
Used as a polyvinyl chloride (PVC) solvent, cyclohexanone caused contact dermatitis in a woman manufacturing PVC fluidotherapy bags. Cyclohexanone probably does not cross react with cyclohexanone resin. A cyclohexanone-derived resin used in paints and varnishes caused contact dermatitis in painters.
Chemische Eigenschaften
Cyclohexanone is a water-white to slightly yellow liquid with a peppermint-like or acetone-like odor. The Odor Threshold is 0.12 0.24 ppm in air.
Physikalische Eigenschaften
Clear, colorless to pale yellow, oily liquid with a peppermint-like odor. Experimentally determined detection and recognition odor threshold concentrations were identical: 480 μg/m³ (120 ppm_v) (Hellman and Small, 1974).
Occurrence
Reported present in Cistus labdaniferus.
Verwenden
Cyclohexanone is used in the productionof adipic acid for making nylon; in thepreparation of cyclohexanone resins; and asa solvent for nitrocellulose, cellulose acetate,resins, fats, waxes, shellac, rubber, and DDT..
Verwenden
Industrial solvent for cellulose acetate resins, vinyl resins, rubber, and waxes; solventsealer for polyvinyl chloride; in printing industry; coating solvent in audio and videotape production
Verwenden
Cyclohexanone is used as an industrial solvent and paint remover. It acts as a precursor to nylon 6,6 and nylon 6 and cyclohexanone oxime, which gives caprolactam on rearrangement. Further, it is used as a chemical reaction medium, adhesives, sealants and agricultural products.
Definition
ChEBI: A cyclic ketone that consists of cyclohexane bearing a single oxo substituent.
Synthesis Reference(s)
Canadian Journal of Chemistry, 62, p. 1031, 1984 DOI: 10.1139/v84-171
Tetrahedron Letters, 25, p. 3309, 1984 DOI: 10.1016/S0040-4039(01)81371-X
Allgemeine Beschreibung
A colorless to pale yellow liquid with a pleasant odor. Less dense than water . Flash point 111°F. Vapors heavier than air. Used to make nylon, as a chemical reaction medium, and as a solvent.
Air & Water Reaktionen
Flammable. Soluble in water.
Reaktivität anzeigen
Cyclohexanone forms an explosive peroxide with H2O2, and reacts vigorously with oxidizing materials (nitric acid).
Health Hazard
The toxicity of cyclohexanone in test specieswas found to be low to moderate. Exposureto its vapors can produce irritation in the eyesand throat. Splashing into the eyes can damagethe cornea. Throat irritation in humansmay occur from 3–5 minute exposure to a50-ppm concentration in air. The symptomsof chronic toxicity in animals from its inhalationwere liver and kidney damage, as wellas weight loss. However, its acute toxicitywas low below 3000 ppm. The symptomsin guinea pigs were lacrimation, salivation,lowering of heart rate, and narcosis. Exposureto 4000 ppm for 4–6 hours was lethalto rats and guinea pigs.
The oral toxicity of this compound waslow. Ingestion may cause narcosis and depressionof the central nervous system. It canbe absorbed through the skin.
LD50 value, dermal (rabbits): 1000 mg/kg
LD50 value, intraperitoneal (rats): 1130 mg/kg.
Health Hazard
Inhalation of vapors from hot material can cause narcosis. The liquid may cause dermatitis.
Brandgefahr
HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
Flammability and Explosibility
Flammable
Chemische Reaktivität
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Kontakt-Allergie
Used as a polyvinyl chloride solvent, cyclohexanone caused contact dermatitis in a woman manufacturing PVC fluidotherapy bags. Cyclohexanone probably does not cross-react with cyclohexanone resin. A cyclohexanone-derived resin used in paints and varnishes caused contact dermatitis in painters
Sicherheitsprofil
Suspected carcinogen. Moderately toxic by ingestion, inhalation, subcutaneous, intravenous, and intraperitoneal routes. A skin and severe eye irritant. Human systemic effects by inhalation: changes in the sense of smell, conjunctiva irritation, and unspecified respiratory system changes. Human irritant by inhalation. Mdd narcotic properties have also been ascribed to it. Human mutation data reported. Experimental reproductive effects. Flammable liquid when exposed to heat or flame; can react vigorously with oxidizing materials. Slight explosion hazard in its vapor form, when exposed to flame.Reaction with hydrogen peroxide + nitric acid forms an explosive peroxide. To fight fire, use alcohol foam, dry chemical, or COa. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES and CYCLOHEXANE.
Synthese
It may be synthesized on a laboratory scale by the oxidation of cyclohexanol.
mögliche Exposition
May form explosive mixture with air. Contact with oxidizing agents or nitric acid may cause a violent reaction. Do not use brass, copper, bronze, or lead fittings. Attacks many coatings and plastic materials.
Erste Hilfe
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
Carcinogenicity
IARC considers the animal data for cyclohexanone as inadequate evidence of carcinogenicity and listed cyclohexanone as not classifiable for carcinogenicity (IARC Category 3).
Environmental Fate
Biological. In activated sludge inoculum, 96.0% COD removal was achieved. The average rate of biodegradation was 30.0 mg COD/g?h (Pitter, 1976).
Photolytic. Atkinson (1985) reported an estimated photooxidation rate constant of 1.56 x 10^-11 cm³/molecule?sec for the reaction of cyclohexanone and OH radicals in the atmosphere at 298 K. Chemical/Physical. Cyclohexanone will not hydrolyze because it has no hydrolyzable functional group.
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in effluent concentration of 332 mg/L. The adsorbability of the carbon used was 134 mg/g carbon (Guisti et al., 1974). Similarly, at influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities were 36, 6.2, 1.1, and 0.19 mg/g, respectively (Dobbs and Cohen, 1980).
Lager
Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with Cyclohexanone you should be trainedon its proper handling and storage. Before entering confinedspace where this chemical may be present, check to make sure that an explosive concentration does not exist.Cyclohexanone must be stored to avoid contact with oxidizers (such as perchlorates, peroxides, chlorates, nitrates, andpermanganates), since violent reactions occur. Store intightly closed containers in a cool well-ventilated area awayfrom heat, sparks, and flames. Metal containers involvingthe transfer of this chemical should be grounded andbonded. Where possible, automatically pump liquid fromdrums or other storage containers to process containers.Drums must be equipped with self-closing valves, pressurevacuum bungs, and flame arresters. Use only nonsparkingtools and equipment, especially when opening and closingcontainers of this chemical. Sources of ignition, such assmoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could createa potential fire or explosion hazard. Wherever this chemicalis used, handled, manufactured, or stored, use explosionproof electrical equipment and fittings.Cyclohexanone requires a “FLAMMABLELIQUID” label. It falls in Hazard Class 3 and PackingGroup II
Versand/Shipping
UN1915 Cyclohexanone, Hazard Class: 3; Labels: 3-Flammable liquid.
läuterung methode
Dry cyclohexanone with MgSO4,CaSO4, Na2SO4 or Linde type 13X molecular sieves, then distil it. Cyclohexanol and other oxidisable impurities can be removed by treatment with chromic acid or dilute KMnO4. More thorough purification is possible by conversion to the bisulfite addition compound, or the semicarbazone, followed by decomposition with Na2CO3 and steam distillation. [For example, equal weights of the bisulfite adduct (crystallised from water) and Na2CO3 are dissolved in hot water and, after steam distillation, the distillate is saturated with NaCl and extracted with Et2O which is then dried (anhydrous MgSO4 or Na2SO4), filtered and the solvent evaporated prior to further distillation.] FLAMMABLE [Beilstein 7 III 14, 7 IV 15.]
Inkompatibilitäten
May form explosive mixture with air. Contact with oxidizing agents or nitric acid may cause a violent reaction. Do not use brass, copper, bronze, or lead fittings. Attacks many coatings and plastic materials.
Waste disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinera- tor equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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Cyclohexanon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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