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Ethyl acetoacetate

Ethyl acetoacetate
Ethyl acetoacetate structure
CAS No.
141-97-9
Chemical Name:
Ethyl acetoacetate
Synonyms
EAA;ACE;EAA en;FEMA 2415;diaceticester;DIACETIC ETHER;Ethylacetacetat;ACETOACETIC ESTER;ACETOACETIC ETHER;AKOS BBS-00004335
CBNumber:
CB0301721
Molecular Formula:
C6H10O3
Formula Weight:
130.14
MOL File:
141-97-9.mol

Ethyl acetoacetate Properties

Melting point:
−43 °C(lit.)
Boiling point:
181 °C(lit.)
Density 
1.029 g/mL at 20 °C(lit.)
vapor density 
4.48 (vs air)
vapor pressure 
1 mm Hg ( 28.5 °C)
refractive index 
n20/D 1.419
FEMA 
2415 | ETHYL ACETOACETATE
Flash point:
185 °F
storage temp. 
Store below +30°C.
solubility 
116 g/L (20°C)
pka
11(at 25℃)
form 
Liquid
Specific Gravity
1.027~1.035 (20/4℃)
color 
APHA: ≤15
Relative polarity
0.577
PH
4.0 (110g/l, H2O, 20℃)
Odor
Agreeable, fruity.
explosive limit
1.0-54%(V)
Water Solubility 
116 g/L (20 ºC)
Merck 
14,3758
JECFA Number
595
BRN 
385838
Stability:
Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible.
InChIKey
XYIBRDXRRQCHLP-UHFFFAOYSA-N
Substances Added to Food (formerly EAFUS)
ETHYL ACETOACETATE
FDA 21 CFR
172.515; 175.300
CAS DataBase Reference
141-97-9(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
IZP61H3TB1
NIST Chemistry Reference
Butanoic acid, 3-oxo-, ethyl ester(141-97-9)
EPA Substance Registry System
Ethyl acetoacetate (141-97-9)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H227-H319-H303
Precautionary statements  P210e-P280a-P305+P351+P338-P337+P313-P501a-P210-P264-P280-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501
Hazard Codes  Xi
Risk Statements  36
Safety Statements  26-24/25
RIDADR  UN 1993
WGK Germany  1
RTECS  AK5250000
Autoignition Temperature 580 °F
TSCA  Yes
HazardClass  3.2
PackingGroup  III
HS Code  29183000
Toxicity LD50 orally in rats: 3.98 g/kg (Smyth)
NFPA 704
2
1 0

Ethyl acetoacetate price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 00410 Ethyl acetoacetate puriss. p.a., ≥99.0% (GC) 141-97-9 100ml $39.2 2021-03-22 Buy
Sigma-Aldrich 8.09622 Ethyl acetoacetate for synthesis 141-97-9 1 L $49.58 2021-03-22 Buy
Sigma-Aldrich 8.09622 Ethyl acetoacetate for synthesis 141-97-9 100 mL $31.36 2021-03-22 Buy
Sigma-Aldrich W241512 Ethyl acetoacetate natural, ≥97%, FG 141-97-9 100 g $70 2021-03-22 Buy
Sigma-Aldrich W241504 Ethyl acetoacetate ≥99%, FCC, FG 141-97-9 1 kg $70 2021-03-22 Buy

Ethyl acetoacetate Chemical Properties,Uses,Production

Description

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.

Chemical Properties

Ethyl acetoacetate has a characteristic ether-like, fruity, pleasant, refreshing odor.

Chemical Properties

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.

Occurrence

Naturally occurring in strawberry, coffee, sherry, passion fruit juice (yellow), babaco fruit (Carica pentagona Heilborn) and bread.

Uses

Ethyl acetoacetate (EAA) is used as starting material for the syntheses of alpha-substituted acetoacetic esters and cyclic compounds, e.g. pyrazole, pyrimidine and coumarin derivatives as well as intermediate for vitamins and pharmaceuticals. Product Data Sheet

Definition

This compound is a tautomer at room temperature consisting of about 93% keto form and 7% enol form.

Production Methods

Ethyl acetoacetate is manufactured through a reaction of high-purity ethyl acetate with sodium, followed by neutralization with sulfuric acid.

Preparation

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.

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

General Description

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 Reactions

Flammable.

Reactivity Profile

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.

Chemical Reactivity

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.

Chemical Reactivity

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.

Safety Profile

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.

Chemical Synthesis

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.

Purification Methods

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.]

Ethyl acetoacetate Preparation Products And Raw materials

Raw materials

Preparation Products


Ethyl acetoacetate Suppliers

Global( 568)Suppliers
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View Lastest Price from Ethyl acetoacetate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-25 Ethyl acetoacetate
141-97-9
US $0.00 / Kg/Drum 1KG 99.9% 100000kg per month Wuhan Mulei New Material Technology Co. Ltd
2021-10-19 Ethyl acetoacetate
141-97-9
US $48.00-40.00 / KG 1公斤 99% 2tons Guangzhou Sunton Biotechnology Co., Ltd.
2021-09-29 Ethyl acetoacetate
141-97-9
US $0.00 / Kg/Drum 1KG 98%min 10 tons WUHAN FORTUNA CHEMICAL CO., LTD

Ethyl acetoacetate Spectrum


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