Ethyl acetoacetate
- Product Name
- Ethyl acetoacetate
- CAS No.
- 141-97-9
- Chemical Name
- Ethyl acetoacetate
- Synonyms
- ETHYL 3-OXOBUTANOATE;ACE;EAA;Ethyl acetoacetate, 99%, pure;ACETOACETIC ESTER;Ethyl acetyl acetate;Acetoacetic acid ethyl;Ethyl acetoacetate(EAA);Ethyl acetoacetate, extra pure;3-OXOBUTANOIC ACID ETHYL ESTER
- CBNumber
- CB0301721
- Molecular Formula
- C6H10O3
- Formula Weight
- 130.14
- MOL File
- 141-97-9.mol
Ethyl acetoacetate Property
- 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
- color
- APHA: ≤15
- Specific Gravity
- 1.027～1.035 (20/4℃)
- Odor
- Agreeable, fruity.
- PH
- 4.0 (110g/l, H2O, 20℃)
- Relative polarity
- 0.577
- explosive limit
- 1.0-54%(V)
- Odor Type
- fruity
- Water Solubility
- 116 g/L (20 ºC)
- JECFA Number
- 595
- Merck
- 14,3758
- BRN
- 385838
- Dielectric constant
- 15.0（Ambient）
- Stability:
- Stable. Incompatible with acids, bases, oxidizing agents, reducing agents, alkali metals. Combustible.
- InChIKey
- XYIBRDXRRQCHLP-UHFFFAOYSA-N
- LogP
- 0.8 at 20℃
- CAS DataBase Reference
- 141-97-9(CAS DataBase Reference)
- NIST Chemistry Reference
- Butanoic acid, 3-oxo-, ethyl ester(141-97-9)
- EPA Substance Registry System
- Ethyl acetoacetate (141-97-9)
Safety
- 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
- Hazardous Substances Data
- 141-97-9(Hazardous Substances Data)
- Toxicity
- LD50 orally in rats: 3.98 g/kg (Smyth)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H227Combustible liquid
H303May be harmfulif swallowed
H319Causes serious eye irritation
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313IF eye irritation persists: Get medical advice/attention.
P370+P378In case of fire: Use … for extinction.
P403+P235Store in a well-ventilated place. Keep cool.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- W241512
- Product name
- Ethyl acetoacetate
- Purity
- natural, ≥97%, FG
- Packaging
- 100g
- Price
- $65.7
- Updated
- 2024/03/01
- Product number
- W241512
- Product name
- Ethyl acetoacetate
- Purity
- natural, ≥97%, FG
- Packaging
- 1kg
- Price
- $207
- Updated
- 2024/03/01
- Product number
- W241512
- Product name
- Ethyl acetoacetate
- Purity
- natural, ≥97%, FG
- Packaging
- 5kg
- Price
- $875
- Updated
- 2024/03/01
- Product number
- W241504
- Product name
- Ethyl acetoacetate
- Purity
- ≥99%, FCC, FG
- Packaging
- 1kg
- Price
- $71.7
- Updated
- 2024/03/01
- Product number
- W241504
- Product name
- Ethyl acetoacetate
- Purity
- ≥99%, FCC, FG
- Packaging
- 5kg
- Price
- $182
- Updated
- 2024/03/01
Ethyl acetoacetate Chemical Properties,Usage,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 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.
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.
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
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.
Flammability and Explosibility
Non flammable
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.
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.]
References
[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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View Lastest Price from Ethyl acetoacetate manufacturers
- Product
- Ethyl Acetoacetate 141-97-9
- Price
- US $180.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-06-03
- Product
- Ethyl acetoacetate 141-97-9
- Price
- US $0.00/G
- Min. Order
- 1G
- Purity
- 99%
- Supply Ability
- 20
- Release date
- 2024-03-27
- Product
- Ethyl acetoacetate 141-97-9
- Price
- US $20.00/kg
- Min. Order
- 1kg
- Purity
- 99.9%
- Supply Ability
- 10000
- Release date
- 2023-04-13