Cyclohexanon 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.
LD
50 (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/m
3
(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..
Definition
ChEBI: A cyclic ketone that consists of cyclohexane bearing a single oxo substituent.
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.
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.
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.
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.
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
cm
3/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).
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.
Cyclohexanon Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Venlafaxine hydrochloride
ethyl-2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-carboxylat
Pramipexole
Hexan-6-olid
(1S,2S)-(-)-1,2-Diphenyl-1,2-ethanediamine
N,N-Dimethylcyclohexanamin
1-Ethinylcyclohexanol
Carbosulfan
Porcelain-like coating
2-ETHYLCYCLOHEXANONE
2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-carbonitril
(R)-1,5-Dimethylhexylamin
3-AMINO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
2-(1-Cyclohexen-1-yl)cyclohexan-1-on
Tramadol hydrochloride
Clethodim
1-NITROMETHYLCYCLOHEXANOL
3-AMINO-5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]PYRIMIDIN-4-ONE
1-Aminomethylcyclohexan-1-olhydrochlorid
Methoxydienone
5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]-PYRIMIDIN-4-ONE
Polyurethane varnish
Cyclohexanon, Peroxid
Cyclohexyl(methyl)amin
Ondansetron
Ethyl-2-oxocyclohexancarboxylat
Venlafaxine
1-(1-PIPERIDINO)CYCLOHEXENE
adhesive No.1 for shrink packaging
2-Chlorcyclohexanon
Tacrin
(1-HYDROXY-CYCLOHEXYL)-ACETONITRILE
Cyclohexan-1,2-dion
Sulfadimidin
Deflazacort
1-Hydroperoxycyclohexyl-1-hydroxycyclohexylperoxid
2-(HYDROXYMETHYL)CYCLOHEXANONE
Cycloheptanon
Dinatrium-7-hydroxy-8-[[4-[1-[4-[(4-hydroxyphenyl)azo]phenyl]cyclohexyl]phenyl]azo]naphthalin-1,3-disulfonat
1-(Aminomethyl)cyclohexan-1-ol
