Ethylacetoacetat

Bezeichnung:Ethylacetoacetat

CAS-Nr141-97-9

Englisch Name:Ethyl acetoacetate

CBNumberCB0301721

SummenformelC6H10O3

Molgewicht130.14

MOL-Datei141-97-9.mol

Synonyma

Ethylacetoacetat

Acetessigs?ureethylester

Ethyl(acetylacetat)

Ethylacetoacetat physikalisch-chemischer Eigenschaften

Schmelzpunkt	−43 °C(lit.)
Siedepunkt	181 °C(lit.)
Dichte	1.029 g/mL at 20 °C(lit.)
Dampfdichte	4.48 (vs air)
Dampfdruck	1 mm Hg ( 28.5 °C)
FEMA	2415 \| ETHYL ACETOACETATE
Brechungsindex	n20/D 1.419
Flammpunkt	185 °F
storage temp.	Store below +30°C.
Löslichkeit	116 g/L (20°C)
pka	11(at 25℃)
Aggregatzustand	Liquid
Wichte	1.027～1.035 (20/4℃)
Farbe	APHA: ≤15
Relative polarity	0.577
PH	4.0 (110g/l, H2O, 20℃)
Geruch (Odor)	Agreeable, fruity.
Explosionsgrenze	1.0-54%(V)
Geruchsart	fruity
Wasserlöslichkeit	116 g/L (20 ºC)
Merck	14,3758
JECFA Number	595
BRN	385838
Dielectric constant	15.0（Ambient）
Stabilität	Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible.
InChIKey	XYIBRDXRRQCHLP-UHFFFAOYSA-N
LogP	0.8 at 20℃
CAS Datenbank	141-97-9(CAS DataBase Reference)
NIST chemische Informationen	Butanoic acid, 3-oxo-, ethyl ester(141-97-9)
EPA chemische Informationen	Ethyl acetoacetate (141-97-9)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36
S-Sätze:	26-24/25
RIDADR	UN 1993
WGK Germany	1
RTECS-Nr.	AK5250000
Selbstentzündungstemperatur	580 °F
TSCA	Yes
HazardClass	3.2
PackingGroup	III
HS Code	29183000
Giftige Stoffe Daten	141-97-9(Hazardous Substances Data)
Toxizität	LD50 orally in rats: 3.98 g/kg (Smyth)

Gefahreninformationscode (GHS)

Ethyl acetoacetate Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.
PHYSIKALISCHE GEFAHREN
Die Dämpfe sind schwerer als Luft.
CHEMISCHE GEFAHREN
Reagiert mit starken Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt.
MAK: IIb (MAK nicht festgelegt, aber Informationen vorhanden). (DFG 2008).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C tritt eine gesundheitsschädliche Kontamination der Luft nicht oder nur sehr langsam ein , viel schneller jedoch beim Versprühen oder Dispergieren..
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt die Augen, die Haut und die Atemwege.
LECKAGE
Ausgelaufene Flüssigkeit möglichst in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. Reste mit viel Wasser wegspülen.
R-Sätze Betriebsanweisung:
R36:Reizt die Augen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and amino pyrine, and vitamin B₁; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.
Chemische Eigenschaften
Ethyl 3-Oxobutanoate is a colorless liquid with a fruity, ethereal, sweet odor reminiscent of green apples. It is used to create fresh, fruity top notes in feminine fine fragrances. Ethyl acetoacetate occurs in flavors of natural materials such as coffee, strawberries, and yellow passion fruits.
Chemische Eigenschaften
Ethyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor.
Occurrence
Naturally occurring in strawberry, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona Heilborn) and bread.
Verwenden
Ethyl acetoacetate is used as an intermediate in organic synthesis and as a co-promoter for unsaturated polyester resins. It is widely used in the production of dyes, inks, perfumes, plastics and flavoring agents. It is an important starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds like pyrazole, pyrimidine and coumarin derivatives. It acts as an intermediate in the synthesis of vitamins and pharmaceuticals. It finds application as a formaldehyde scavenger.
synthetische
Ethyl acetoacetate is produced industrially by treatment of diketene with ethanol.
The preparation of ethyl acetoacetate is a classic laboratory procedure . It is prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.
Definition
ChEBI: Ethyl acetoacetate is an ethyl ester resulting from the formal condensation of the carboxy group of acetoacetic acid with ethanol. It has a role as a flavouring agent, an antibacterial agent and a plant metabolite. It is functionally related to an acetoacetic acid.
Application
Ethyl acetoacetate can be used as a potential bio-based diluent for improving the cold flow properties of biodiesel from waste cooking oil^[1]. Ethyl acetoacetate reacts with glycosylamines to form ethyl 3-(glycosylamino)crotonate, which is further transformed into ethyl 2-methyl-4-(polyhydroxyalkyl)pyrrole-3-carboxylates under conditions that promote the Amadori rearrangement of glycosylamines. It also reacts with ketohexylamines (D-fructosylamine, L-sorbosylamine) to form ethyl 2-methyl-5-(tetrahydroxybutyl)pyrrole-3-carboxylates^[2].
Aroma threshold values
Detection: 520 ppb. Aroma characteristics at 10%: sweet fruity apple, fermented, slightly fusel-like and rummy, fruity banana with tropical nuances.
Taste threshold values
Taste characteristics at 100 ppm: fruity banana, apple and white grape with slightly green estry and tropical nuances.Taste characteristics at 300 ppm: estery, fatty, fruity and tutti-frutti
Synthesis Reference(s)
The Journal of Organic Chemistry, 58, p. 793, 1993 DOI: 10.1021/jo00055a046
Allgemeine Beschreibung
A colorless liquid with a fruity odor. Flash point 185°F. Boiling point 365°F. May cause adverse health effects if ingested or inhaled. May irritate to skin, eyes and mucous membranes. Used in organic synthesis and in lacquers and paints.
Air & Water Reaktionen
Flammable.
Reaktivität anzeigen
Ethyl acetoacetate, a beta-keto ester, is more reactive than many esters. Undergoes an exothermic cleavage reaction in the presence of concentrated base. Reacts with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Mixing with 2,2,2-tris(bromomethyl)ethanol and zinc led to an explosion [US Patent 3 578 619, Crotonaldehyde may rapidly polymerize with Ethyl acetoacetate (Soriano, D.S. et al. 1988. Journal of Chemical Education 65:637.).1971].
Hazard
Toxic by ingestion and inhalation; irritant to skin and eyes.
Health Hazard
Liquid may cause mild irritation of eyes.
Flammability and Explosibility
Non flammable
Chemische Reaktivität
Ethyl acetoacetate is subject to Keto - enol tautomerism. Ethyl acetoacetate is often used in the acetoacetic ester synthesis similar to diethyl malonate in the malonic ester synthesis or the Knoevenagel condensation. The protons alpha to carbonyl groups are acidic, and the resulting carbanion can undergo nucleophilic substitution. A subsequent thermal decarboxylation is also possible.Similar to the behavior of acetylacetone, the enolate of ethyl acetoacetate can also serve as a bidentate ligand. For example, it forms purple coordination complexes with iron (III) salts :
Ethyl acetoacetate can also be reduced to ethyl 3-hydroxy butyrate.
Sicherheitsprofil
eye irritant. Combustible liquid when exposed to heat or flame; can react with oxidzing materials. Explosive reaction when heated with Zn + tribromoneopentyl alcohol or 2,2,2 tris(bromomethy1)ethanol. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
Synthese
Ethyl acetoacetate is a mixture of two tautomer forms: the enolic and the ketonic; the liquid ester at equilibrium contains approximately 70% of the enolic form. It is prepared by Claisen condensation of ethyl acetate in the presence of sodium ethylate; also by reacting diketene with ethanol in the presence of sulfuric acid or triethylamine and sodium acetate, with or without solvent.
läuterung methode
Shake the ester with small amounts of saturated aqueous NaHCO3 (until no further effervescence), then with water. Dry it with MgSO4 or CaCl2 and distil it under reduced pressure. [Beilstein 3 IV 1528.]
Einzelnachweise
[1] LEICHANG CAO. Ethyl acetoacetate: A potential bio-based diluent for improving the cold flow properties of biodiesel from waste cooking oil[J]. Applied Energy, 2014, 114: Pages 18-21. DOI:10.1016/j.apenergy.2013.09.050.
[2] A.GóMEZ SáNCHEZ; J. V del P. Reaction of glycosylamines with ethyl acetoacetate[J]. Carbohydrate Research, 1966, 1 6: Pages 421-434. DOI:10.1016/S0008-6215(00)81220-3.

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