2,4-Pentandion 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.
Verwenden
Acetylacetone was used in preparing Y
20
3, La
20
3 and La
2CuO
4 thin films and the titanate/anatase dual-phase photocatalyst.
Definition
ChEBI: A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.
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.
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.
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.
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.
2,4-Pentandion Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Tetrahydrocurcumin
5-CYANO-6-HYDROXY-4-METHOXYMETHYL-2-METHYLPYRIDINE
Aluminiumtris(2,4-pentandionato-O,O')
17-Ethinyl-3,17-dihydroxy-18-methylestra-2,5(10)-diene3-methylether
Indan-1,2,3-trion
3-(3,5-DIMETHYL-PYRAZOL-1-YL)-PROPYLAMINE
1,2-DIHYDRO-4-(METHOXYMETHYL)-6-METHYL-5-NITRO-2-OXONICOTINONITRILE
4-methoxymethylpyridoxine
2-AMINO-4,6-DIMETHYL-3-PYRIDINECARBOXAMIDE
5-BROMO-2-CHLORO-4,6-DIMETHYLNICOTINONITRILE
4,6-Dimethyl-2-methylmercapyrimidine
4,6-DIMETHYL-PYRIMIDINE-2-SULFONYL FLUORIDE
1,4,6-Trimethyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine ,97%
2-(2-CARBOXYETHYL)THIO-4,6-DIMETHYLPYRIMIDINE
4,6-DIMETHYL-2-THIOPYRIMIDINE
[(4,6-Dimethylpyrimidin-2-yl)thio]essigsure
13-Ethyl-17-hydroxy-18,19-dinorpregn-5(10)-en-20-yn-3-one
1-(2,4-Dimethylthiazol-5-yl)ethan-1-on
Palladium(II)di(4-oxopent-2-en-2-oat)
4,6-Dimethyl-1H-pyrimidin-2-onhydrochlorid
2-Hydroxy-4,6-dimethylnicotinonitril
2-Ethyl-3-methylpyrazin
MEQUINDOX
6-CHLORO-5-CYANO-4-METHOXYMETHYL-3-NITRO-2-PICOLINE
17-Ethinyl-17-hydroxy-18-methylestra-5(10),9(11)-dien-3-one-3-ethylene ketal
4,6-Dimethylpyrimidin-2-ylamin
1-(4-METHYL-2-(METHYLTHIO)PYRIMIDIN-5-YL)ETHANONE
3-(PYRIMIDIN-2-YLTHIO)PENTANE-2,4-DIONE
1-(2,4-DIMETHYLQUINOLIN-3-YL)ETHANONE HYDROCHLORIDE
2-Chloro-3-cyano-4,6-dimethylpyridine
3,5-Dimethyl-1H-pyrazol-1-carboxamidinmononitrat
5-AMINO-4-(METHOXYMETHYL)-6-METHYL-3-PYRIDINEMETHANAMINE
3,5-DIMETHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID
Sulfadimidin
3-ACETYL-2-METHYL-QUINOLINE-4-CARBOXYLIC ACID
5-BROMO-4,6-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-AMINE
4,6-Dimethyl-2-hydroxypyridine
17-Ethynyl-18-methylestra-5(10),9(11)-dien-17-ol-3-one
4,6-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-AMINE
2-CHLORO-3-(3,5-DIMETHYL-PYRAZOL-1-YL)-QUINOXALINE
