2-Propenal Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
GELBE BIS FARBLOSE FLüSSIGKEIT MIT STECHENDEM GERUCH.
PHYSIKALISCHE GEFAHREN
Die Dämpfe sind schwerer als Luft und können sich am Boden ausbreiten. Fernzündung möglich.
CHEMISCHE GEFAHREN
Bildung explosionsfähiger Peroxide. Kann polymerisieren unter Feuer- und Explosionsgefahr. Beim Erhitzen bilden sich giftige Rauche. Reagiert mit starken Säuren, starken Basen und starken Oxidationsmitteln. Feuer- und Explosionsgefahr.
ARBEITSPLATZGRENZWERTE
TLV: (als STEL, ceiling) 0,1 ppm Hautresorption; Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK: Krebserzeugend Kategorie 3B; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation der Dämpfe, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20 °C kann sehr schnell eine gesundheitsschädliche Kontamination der Luft eintreten.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Tränenreizend. Die Substanz reizt stark die Augen, die Haut und die Atmungsorgane. Inhalation dieser Substanz in hohen Konzentrationen kann zu Lungenödem führen (s. Anm.). Die Auswirkungen treten u.U. verzögert ein. ärztliche Beobachtung notwendig.
LECKAGE
Gefahrenbereich verlassen! Zündquellen entfernen. Fachmann zu Rate ziehen! Ausgelaufene Flüssigkeit in abgedeckten Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Umwelt gelangen lassen. Chemikalienschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät.
R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R24/25:Giftig bei Berührung mit der Haut und beim Verschlucken.
R26:Sehr giftig beim Einatmen.
R34:Verursacht Verätzungen.
R50:Sehr giftig für Wasserorganismen.
S-Sätze Betriebsanweisung:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und 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.
Aussehen Eigenschaften
C3H4O; Acrolein, stabilisiert mit Hydrochinon (2g/l). Propen-2-al, Acrylaldehyd, Allylaldehyd. Farblose Flüssigkeit mit stechendem Geruch.
Gefahren für Mensch und Umwelt
Leichtentzündlich. Giftig beim Verschlucken. Sehr giftig beim Einatmen. Verursacht Verätzungen. Starke Reizwirkung auf Haut, Augen, Schleimhäute.
Sehr giftig beim Einatmen. Verursacht Verätzungen.
Nicht ins Abwasser gelangen lassen.
Schutzmaßnahmen und Verhaltensregeln
Keine Kunststofflaschen verwenden. Elektrostatische Aufladung vermeiden.
Schutzhandschuhe (nur kurzzeitiger Spritzschutz)
Substanzkontakt vermeiden.
Verhalten im Gefahrfall
Reinigungsverfahren: mit Kieselgur, Rench Rapid oder Sand aufnehmen, in geschlossenen Behältern der Entsorgung zuführen
Kohlendioxid, Wasser in Sprühstrahl, Pulver
Erste Hilfe
Nach Hautkontakt: Sofort mit viel Wasser und Seife abwaschen.
Nach Augenkontakt: Mindestens 15 Minuten bei geöffnetem Lidspalt mit viel Wasser spülen. Sofort zum Augenarzt.
Nach Einatmen: An die frische Luft und ruhig lagern, Wasserdampf einatmen lassen.
Nach Verschlucken: Viel Wasser mit Aktivkohle trinken lassen, Erbrechen auslösen, sofort zum Arzt.
Nach Kleidungskontakt: Sofort Kleidung ablegen, Haut mit viel Wasser und Seife waschen.
Nach Einatmen verdünnte Ammoniak-Dämpfe einatmen lassen.
Nach Verschlucken Magenspülung mit Harnstoff und Kohle über Nasensonde
Sauerstoffzufuhr, Beatmung, Schocktherapie.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Halogenfreie organische Lösemittelabfälle.
Beschreibung
The first time that acrolein was produced as a commercial
product was in the 1930s through the vapor-phase condensation
of acetaldehyde and formaldehyde. Another method was
developed in the 1940s, which involved the vapor-phase
oxidation of propylene. In the 1960s, some advances were
found in propylene oxidation process by the introduction of
bismuth molybdate-based catalysis, and that became the
primary method used for the commercial production of acrolein.
Some bioproducts formed for this reaction are acrylic acid,
carbon oxides, acetaldehyde, acetic acid, formaldehyde, and
polyacrolein. In World War I, it was used as a chemical weapon
(pulmonary irritant and lachrymatory agent). Commercial
acrolein contains 95.5% or more of the compound, the main
impurities being water (<3.0% by weight) and other carbonyl
compounds (<1.5% by weight), mainly propanol and acetone.
Hydroquinone is added as an inhibitor of polymerization
(0.1–0.25% by weight).
Chemische Eigenschaften
Acrolein is a highly flammable, clear to yellowish liquid. It has a piercing, disagreeable odor and causes tears.
Physikalische Eigenschaften
Colorless to yellow, clear, watery liquid imparting a very sharp, acrid, pungent, or irritating odor.
Odor threshold concentrations reported were 0.11 mg/kg by Guadagni et al. (1963), 0.21 ppm
v by
Leonardos et al. (1969), and 36 ppb
v by Nagata and Takeuchi (1990). In addition, Katz and Talbert
(1930) reported an experimental detection odor threshold concentration of 4.1 mg/m
3 (1.8 ppm
v).
Verwenden
Acrolein is used in the synthesis of acrylic acid. manufacture of colloidal forms of metals; making plastics, perfumes; warning agent in methyl chloride refrigerant. Has been used in military poison gas mixtures. Used in organic syntheses. Aquatic herbicide.
Definition
A colorless liquid unsaturated aldehyde with a pungent odor. It can
be polymerized to make acrylate resins.
Air & Water Reaktionen
Highly flammable. A dangerous fire risk [Hawley]. Water soluble. Reacts slowly and exothermically with water to give 3-hydroxypropionaldehyde. A hazard can develop from this reaction if acrolein is stored over a layer of water.
Reaktivität anzeigen
ACROLEIN, [INHIBITED] can react violently with oxidizing agents. Polymerizes exothermically on contact with small amounts of acids (including sulfur dioxide), alkalis, volatile amines and pyridines, salts, thiourea, oxidizing agents (air) and on exposure to light and heat. Polymerization initiated by amines and pyridines occurs after a deceptive induction period. Water solutions of mineral acids and metal ions can initiate polymerization. The inhibitor (usually hydroquinone) greatly reduces tendency to polymerize. Undergoes Diels-Alder reaction with itself to give acrolein dimer. This can become a runaway reaction at 90°C [Kirk-Othmer, 4th Ed, Vol. 1]. Mixing in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: 2-aminoethanol, ammonium hydroxide, chlorosulfonic acid, ethylenediamine, ethyleneimine [NFPA 1991].
Brandgefahr
Under fire conditions, polymerization may occur. If inside a container, violent rupture of the container may take place. When heated to decomposition, Acrolein emits highly toxic fumes. Alkalis or strong acids act as catalysts, causing a condensation reaction and liberating energy. Reaction may be very rapid and violent. Readily converted by oxygen to hazardous peroxides and acids. Unstable, avoid exposure to alkalis, strong acids, oxygen, elevated temperatures, such as fire conditions. (Polymerization inside container could cause violent rupture of container under fire conditions.)
Flammability and Explosibility
Acrolein is a highly flammable liquid (NFPA rating = 3) and its vapor can travel a
considerable distance and "flash back." Acrolein vapor forms explosive mixtures
with air at concentrations of 2.8 to 31% (by volume). Carbon dioxide or dry
chemical extinguishers should be used for acrolein fires.
Sicherheitsprofil
Human poison by inhalation and intradermal routes. Poison experimentally by most routes. Human systemic irritant and pulmonary system effects by inhalation include: lachrymation, delayed hypersensitivity with multiple organ involvement, and respiratory system damage. Severe eye and skin irritant. Experimental reproductive effects. Human mutation data reported. Questionable carcinogen. Dangerous fire hazard when exposed to heat, flame, or oxidizers. An explosion hazard. Incompatible with amines, SO2, metal salts, oxidants, (light + heat). Violent polymerization reaction on contact with strong acid, strong base, weak acid conditions (e.g., nitrous fumes, sulfur dioxide, carbon dioxide), thiourea, or dimethylamine. When heated to decomposition it emits highly toxic fumes; can react vigorously with oxidizing materials. To fight fire, use CO2, dry chemical, or alcohol foam,
mögliche Exposition
Used as pharmaceutical; slimicide; and in production of cosmetics and food supplements; as an intermediate in the production of glycerine and in the production of methionine analogs (poultry feed protein supplements). It is also used in chemical synthesis (1,3,6-hexametriol and glutaraldehyde); as a liquid fuel; antimicrobial agent, in algae and aquatic weed control; and as a slimicide in paper manufacture; making plastics, drugs, and tear gas. Also, most allyl compounds may be metabolized to allyl alcohol which is metabolized to acrolein.
Carcinogenicity
Acrolein is a reactive intermediate
of the commonly used chemotherapeutic drugs cyclophosphamide
and ifosphamide. Acrolein-modified
DNA was found in human peripheral blood lymphocytes
from cancer patients previously treated with cyclophosphamide
(a chemotherapeutic), but no association was
found for cyclophosphamine. Acrolein has a classification
of C, possible human carcinogen, based on limited
animal carcinogenicity data and paucity of human evidence
for this effect.
Stoffwechselwegen
When fish are exposed to 14C-acrolein, the
metabolites are identified from the edible tissues and
there is very little similarity in the metabolism of
acrolein among the test species. The most notable
observation is that acrolein is never detected in any
tissues sampled, and glycidol, glycerol, 1,3-
propanediol, and glyceric acid are the major
metabolites found in catfish, crayfish, bluegill, and
clams, respectively.
Lager
Work with acrolein
should be conducted in a fume hood to prevent exposure by inhalation, and splash
goggles and butyl rubber gloves should be worn at all times to prevent eye and skin
contact. Acrolein should be used only in areas free of ignition sources. Containers of
acrolein should be stored in secondary containers in areas separate from amines,
oxidizers, acids, and bases.
Versand/Shipping
Acrolein, stabilized, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquids. Inhalation Hazard Zone A.
läuterung methode
Purify acrolein by fractional distillation, under nitrogen, drying with anhydrous CaSO4 and then distilling under vacuum. Blacet, Young and Roof [J Am Chem Soc 59 608 1937] distilled it under nitrogen through a 90cm column packed with glass rings. To avoid formation of diacryl, the vapour is passed through an ice-cooled condenser into a receiver cooled in an ice-salt mixture and containing 0.5g catechol. The acrolein is then distilled twice from anhydrous CuSO4 at low pressure, catechol being placed in the distilling flask and the receiver to avoid polymerization. [Alternatively, hydroquinone (1% of the final solution) can be used.] [Beilstein 1 IV 3435.]
Inkompatibilitäten
May form explosive mixture with air. Elevated temperatures or sunlight may cause explosive polymerization. A strong reducing agent; reacts violently 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. Polymerizes exothermically on contact with small amounts of acids (including sulfur dioxide), alkalis, volatile amines and pyridines, salts, thiourea, oxidizing agents (air) and on exposure to light, and heat. Polymerization initiated by amines and pyridines occurs after a deceptive induction period. Water solutions of mineral acids and metal ions can initiate polymerization. The inhibitor (usually hydroquinone) greatly reduces tendency to polymerize. Reacts with acids, alkalis, ammonia, amines, oxygenperoxides. Shock-sensitive peroxides or acids may be formed over time. Attacks zinc and cadmium
Waste disposal
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration. Conditions are 816 C, 0.5 second minimum for primary combustion; 1093 C, 1.0 second for secondary combustion.
2-Propenal Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
2,5-Dimethylpyrazin
Fluvastatin sodium salt
3-(5-Nitro-2-furyl)acrylsure
2-(2-Bromethyl)-1,3-dioxolan
6-Bromchinolin
7-Bromoquinoline
6-Nitrochinolin
2-Methylundecanal
2-Methylpyridin
3,3'-Oxydi(propylenglykol)
Glutardialdehyd
3-Chlorpropionsure
Propionaldehyd
1-Octen-3-ol
3-(Methylthio)propionaldehyd
Glycerol
5-[2-(Methylthio)ethyl]imidazolidin-2,4-dion
DL-Tryptophan
Hexan-1,2,6-triol
Terbinafine
DL-Methionin
3-Chlor-1,1-diethoxypropan
2,3-Dibrompropionaldehyd
Benz[de]anthracen-7-on
2-(Methoxymethyl)-2-propenal
Pent-2-enal
2-Propensäure
Pyridin-2,3-dicarbonsure
2,2-Dibrom-2-cyanacetamid
Chinolin-7-ol
Ethylacrylat
3-(2-Furyl)acrylsure
Methylacrylat
Poly(acrylic acid)
Allylalkoholl
L-Methionin
2,4-Dimethylcyclohex-3-en-1-carbaldehyd
1-(3-PYRROLIDINOPROPYL)PIPERAZINE
Propan-1-ol
