2,4-Pentandion

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H226：Flüssigkeit und Dampf entzündbar.

  H302：Gesundheitsschädlich bei Verschlucken.

• Sicherheit

  P210：Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

Acetylacetone Chemische Eigenschaften,Einsatz,Produktion Methoden

• ERSCHEINUNGSBILD

  FARBLOSE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.

• PHYSIKALISCHE GEFAHREN

  Die Dämpfe sind schwerer als Luft.

• CHEMISCHE GEFAHREN

  Kann polymerisieren unter Einfluss von Licht. Reagiert mit starken Oxidationsmitteln, Basen und reduzierenden Stoffen.

• ARBEITSPLATZGRENZWERTE

  TLV nicht festgelegt (ACGIH 2005).
  MAK: 20 ppm, 83 mg/m?Spitzenbegrenzung: überschreitungsfaktor II(2); Hautresorption; Schwangerschaft: Gruppe C (DFG 2006).
  

• AUFNAHMEWEGE

  Aufnahme in den Körper durch Inhalation der Dämpfe, über die Haut und durch Verschlucken.

• INHALATIONSGEFAHREN

  Nur ungenügende Angaben vorhanden über die Geschwindigkeit, mit der eine gesundheitsschädliche Konzentration in der Luft beim Verdampfen bei 20°C erreicht wird.

• WIRKUNGEN BEI KURZZEITEXPOSITION

  WIRKUNGEN BEI KURZZEITEXPOSITION:
  Die Substanz reizt die Augen, die Haut und die Atemwege. Möglich sind Auswirkungen auf das Nervensystem mit nachfolgenden Gewebeschäden.

• WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION

  Wiederholter oder andauernder Kontakt kann zu Hautsensibilisierung führen. Möglich sind Auswirkungen auf Thymus, Lunge, Zentralnervensystem und Nasenpassage.

• LECKAGE

  Belüftung. Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit viel Wasser wegspülen. NICHT in die Umwelt gelangen lassen. Persönliche Schutzausrüstung: Atemschutzfilter für organische Gase und Dämpfe.

• R-Sätze Betriebsanweisung:

  R11:Leichtentzündlich.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
  R22:Gesundheitsschädlich beim Verschlucken.
  R10:Entzündlich.

• S-Sätze Betriebsanweisung:

  S21:Bei der Arbeit nicht rauchen.
  S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
  S24/25:Berührung mit den Augen und der Haut vermeiden.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

• Aussehen Eigenschaften

  C5H8O2; 2,4-Pentandion. Farblose Flüssigkeit mit scharf stechendem Geruch.

• Gefahren für Mensch und Umwelt

  Gesundheitsschädlich beim Verschlucken.
  Reizt die Augen, Atmungsorgane und die Haut. Schädigt das Nervensystem.
  Inhalation führt zu Schwindel, Bewegungsstörungen, schwerem Atem und Erbrechen.
  Sensibilisierung möglich
  Nicht mit Alkalien, Isocyanaten, starken Oxidationsmitteln, Fluorwasserstoff, Säuren oder Aminen in Berührung bringen.
  Entzündlich.

• Schutzmaßnahmen und Verhaltensregeln

  Schutzhandschuhe als kurzzeitiger Spritzschutz.

• Verhalten im Gefahrfall

  Mit flüssigkeitsbindendem Material aufnehmen. Der Entsorgung zuführen. Nachreinigen mit Wasser.
  Kohlendioxid, Wasser.
  Brennbar. Dämpfe schwerer als Luft. Mit Luft Bildung explosionsfähiger Gemische.

• 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.
  Nach Verschlucken: Erbrechen wegen Aspirationsgefahr vermeiden. Paraffinöl als Laxans geben (3 ml/kg). Sofort Arzt hinzuziehen.
  Nach Kleidungskontakt: Kontaminierte Kleidung sofort entfernen.
  Ersthelfer: siehe gesonderten Anschlag

• Sachgerechte Entsorgung

  Als halogenfreie, organische Lösemittelabfälle.

• Beschreibung

  Acetylacetone (2,4-pentanedione) is a clear or slightly yellowish liquid with a putrid odour. It is readily soluble in water and in organic solvents and incompatible with light, ignition sources, excess heat, oxidising agents, strong reducing agents, and strong bases. On decomposition, acetylacetone releases hazardous products such as carbon monoxide, irritating and toxic fumes and gases, and carbon dioxide. Acetylacetone is used in the production of anti-corrosion agents and its peroxide compounds for the radical initiator application for polymerisation. It is used as a chemical intermediate for drugs (such as sulphamethazine, nicarbazine, vitamin B6, and vitamin K) and pesticides sulfonylurea herbicides and pesticides. It is used as an indicator for the complexometric titration of Fe (III), for the modification of guanidino groups and amino groups in proteins, and for the preparation of metal acetylacetonates for catalyst application.

• Chemische Eigenschaften

  Acetylacetone (2,4-pentanedione) is a clear or slightly yellowish liquid with a putrid odor. It is readily soluble in water. It is with other incompatible materials, light, ignition sources, excess heat, oxidizing agents, strong reducing agents, and strong bases. On decomposition, acetylacetone releases hazardous products, such as carbon monoxide, irritating and toxic fumes and gases, and carbon dioxide. Acetylacetone is used in the production of anticorrosion agents and its peroxide compounds for the radical initiator application for polymerization. It is used as a chemical intermediate for drugs (such as sulfamethazine, nicarbazine, vitamin B6, and vitamin K), sulfonylurea herbicides, and pesticides. It is used as a solvent for cellulose acetate, as an additive in gasoline and lubricant, as a dryer of paint and varnish. It is used as an indicator for the complexometric titration of Fe(III), for the modifi cation of guanidino groups and amino groups in proteins, and in the preparation of metal acetylacetonates for catalyst application.

• Chemische Eigenschaften

  clear liquid

• Chemische Eigenschaften

  Acetylacetone is a beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups. It is a conjugate acid of an acetylacetonate. Pentane-2,4-dione appears as a colorless or yellow colored liquid. Less dense than water. Vapors are heavier than air. Used as a solvent in paints and varnishes.

• Chemische Eigenschaften

  2,4-Pentanedione is a colorless to yellowish liquid with a sour, rancid odor. The Odor Threshold is 0.01 ppm. Or Ethereal-minty odor, somewhat metallic or "chemical". In high dilution, the flavor in aqueous medium is sweet, remotely reminiscent of Peppermint sweetness. Not very stable. The enol form readily passes into equilibrium mixture. Prod. from Acetone plus Ethyl acetate, or Acetone plus Acetic anhydride (with Boron trifluoride).

• Verwenden

  Acetylacetone was used in preparing Y₂0₃, La₂0₃ and La₂CuO₄ thin films and the titanate/anatase dual-phase photocatalyst.

• Verwenden

  Acetyl acetone is used as a reagent fororganic synthesis and as a transition metalchelating agent. Its organometallic complexes are used as additives for gasoline andlubricants, and in varnishes, color, ink, andfungicides.

• Verwenden

  Chemical intermediate, metal chelator, and lubricant additive. 2,4-Pentanedione is used as an intermediate, in particular for the synthesis of heterocyclic substances for biologically active compounds and dyes, and for the production of metal acetylacetonates. Furthermore, 2,4-pentanedione is used as a solvent, and as an absorption and extraction agent, particularly for the separation and purification of metal ions. Another application is for the purification of metalcontaining wastewater and for corrosion protection. 2,4-Pentanedione is also used as a component of catalyst systems for polymerization, copolymerization, oligo- and dimerization.

• Verwenden

  Forms organometallic complexes which are used as gasoline additives, lubricant additives, driers for varnishes and printer's inks, fungicides, insecticides, colors.

• Vorbereitung Methode

  2,4-Pentanedione is produced by thermal or metal-catalyzed rearrangement of isopropenyl acetate(obtained from acetone and ketene):
  
  Isopropenyl acetate vapor is fed at atmospheric pressure through a V2A steel tube with an inner temperature of 520℃. The hot reaction gases are quenched, condensed, and cooled to 20℃, whereby the gaseous byproducts carbon monoxide, carbon dioxide, methane, and ketene are separated. The product is purified by fractional distillation. Other industrially less important processes for the production of 2,4-pentanedione, include the Claisen ester condensation of ethyl acetate with acetone using sodium ethoxide as condensation agent and the acetylation of acetoacetic acid esters with acetic anhydride in the presence of magnesium salts.
  

• Application

  Acetylacetone, also known as 2,4-pentanedione, is an important commodity chemical and widely used as a fuel additive, as dyeing intermediate, in the fields of metal extraction, metal plating, and resin modification. Hantzsch reaction was used as a derivatizing agent for the assay of compounds having a primary amino group. The reagent was reacted with the primary amino group of the drugs to form a product having color and/or emit fluorescence. This condensation reaction was distinguished by its precision, reproducibility, and analytical cost reduction. FLX contains an aliphatic amino group, in the presence of formaldehyde solution, this amino group can condense with two equivalents of acetylacetone to form dihydropyridine derivative that emits yellow fluorescent product. (Figure1). Under optimized conditions of the reaction, FLX gave highly fluorescent product measured at λem 479 nm using 419 nm as excitation.

• Definition

  ChEBI: A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.

• Synthesis Reference(s)

  Journal of the American Chemical Society, 102, p. 2095, 1980 DOI: 10.1021/ja00526a059
  Organic Syntheses, Coll. Vol. 3, p. 17, 1955

• Allgemeine Beschreibung

  A colorless or yellow colored liquid. Less dense than water. Flash point 105°F. Vapors are heavier than air. Used as a solvent in paints and varnishes.

• Air & Water Reaktionen

  Flammable. Soluble in water.

• Reaktivität anzeigen

  Ketones, such as 2,4-Pentanedione, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. May dissolve plastics [USCG, 1999].

• Health Hazard

  Inhalation causes dizziness, headache, nausea, vomiting and loss of consciousness. Contact with liquid irritates eyes.

• Health Hazard

  Exposures to acetyl acetone cause eye irritation, chemical conjunctivitis, corneal damage, and skin irritation (harmful if absorbed through the skin). At low concentrations for long periods, inhalation/dermal absorption of acetyl acetone causes irritation and dermatitis, cyanosis of the extremities, pulmonary edema, and a burning sensation in the chest. Ingestion/accidental ingestion in the workplace can result in gastrointestinal irritation, nausea, vomiting, diarrhea, and CNS depression. Inhalation of high concentrations may cause CNS effects characterized by nausea, headache, dizziness or suffocation, unconsciousness, and coma. The target organ of acetyl acetone poisoning has been identifi ed as the CNS.

• Health Hazard

  Exposure to the vapors of acetyl acetone cancause irritation of the eyes, mucous membrane, and skin. In rabbits 4.76 mg producedsevere eye irritation; the effect on skin wasmild. Other than these, the health hazardsfrom this compound have not been reported.However, based on its structure and the factthat it has two reactive carbonyl groups inthe molecule, this compound should exhibitlow to moderate toxicity at high concentrations, which should be greater than that ofthe C5-monoketones.
  LD50 value, intraperitoneal (mice): 750mg/kg
  LD50 value, oral (rats): 1000 mg/kg
  There is no report on its carcinogenicity inanimals or humans.

• Brandgefahr

  Behavior in Fire: Vapor is heavier than air and may travel to a source of ignition and flash back.

• Sicherheitsprofil

  Poison by ingestion and intraperitoneal routes. Moderately toxic by inhalation. A skin and severe eye irritant. Experimental reproductive effects. Mutation data reported. Flammable liquid when exposed to heat or flame. Incompatible with oxidning materials. To fight fire, use alcohol foam, CO2, dry chemical.

• mögliche Exposition

  Acetoacetic acid derivative. 2,4-Pentanedione is used in gasoline and lubricant additives, fungicides, insecticides, and colors manufacture; as a chemical intermediate and in the manufacture of metal chelates

• Lager

  Acetylacetone should be stored away from heat, sparks, flame, and from sources of ignition. It should be stored in a tightly sealed container, in a cool, dry, well-ventilated area, away from incompatible substances.

• Versand/Shipping

  UN2310 Pentane-2,4-dione, Hazard Class: 3; Labels: 3-Flammable liquid

• läuterung methode

  Small amounts of acetic acid are removed by shaking with small portions of 2M NaOH until the aqueous phase remains faintly alkaline. The sample, after washing with water, is dried with anhydrous Na2SO4, and distilled through a modified Vigreux column (p 11) Cartledge J Am Chem Soc 73 4416 1951]. An additional purification step is fractional crystallisation from the liquid. Alternatively, there is less loss of acetylacetone if it is dissolved in four volumes of *benzene and the solution is shaken three times with an equal volume of distilled water (to extract acetic acid): the *benzene is then removed by distillation at 43-53o and 20-30mm through a helices-packed column. It is then refluxed over P2O5 (10g/L) and fractionally distilled under reduced pressure. The distillate (sp conductivity 4 x 10-8 ohm-1cm-1) is suitable for polarography [Fujinaga & Lee Talanta 24 395 1977]. To recover used acetylacetone, metal ions are stripped from the solution at pH 1 (using 100mL 0.1M H2SO4/L of acetylacetone). The acetylacetone is then washed with (1:10) ammonia solution (100mL/L) and with distilled water (100mL/L, twice), then treated as above. It complexes with Al, Be, Ca, Cd, Ce , Cu, Fe2+, Fe3+ , Mn, Mg, Ni, Pb and Zn. [Beilstein 1 H 777, 1 I 401, 1 II 831, 1 III 3113, 1 IV 3662.]

• Inkompatibilitäten

  Vapors may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. reducing agents; halogens, aliphatic amines; alkanolamines, organic acids; isocyanates. Strong light may cause polymerization.

• Waste disposal

  Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

• Vorsichtsmaßnahmen

  Occupational workers should only use/handle acetyl acetone in a well-ventilated area, with spark-proof tools and explosion-proof equipment. Workers should not cut, weld, braze, solder, drill, grind, pressurize, or expose empty containers to heat, sparks, or flames.

Acetylacetone Upstream-Materialien And Downstream Produkte

2,4-Pentandion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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