Chemical Properties of Ethyl acetoacetate (CAS 141-97-9)

InChI

InChI=1S/C6H10O3/c1-3-9-6(8)4-5(2)7/h3-4H2,1-2H3

InChI Key

XYIBRDXRRQCHLP-UHFFFAOYSA-N

Formula

C6H10O3

SMILES

CCOC(=O)CC(C)=O

Molecular Weight¹

130.14

CAS

141-97-9

Other Names

• 1-ethoxybutane-1,3-dione
• 3-oxobutanoic acid ethyl ester
• 3-oxobutanoic acid, ethyl ester
• Acetoctan ethylnaty
• Active acetylacetate
• Diacetic ether
• EAA
• Ethylacetacetat
• Ethylester kyseliny acetoctove
• NSC 8657
• acetoacetic acid ethyl ester
• acetoacetic acid, ethyl ester
• butanoic acid, 3-oxo-, ethyl ester
• ethyl 3-ketobutyrate
• ethyl 3-oxobutanoate
• ethyl 3-oxobutyrate
• ethyl acetonecarboxylate
• ethyl acetylacetate

• ω : Acentric Factor.
• Δ_cH°_liquid : Standard liquid enthalpy of combustion (kJ/mol).
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• C_p,liquid : Liquid phase heat capacity (J/mol×K).
• η : Dynamic viscosity (Pa×s).
• Δ_fG° : Standard Gibbs free energy of formation (kJ/mol).
• Δ_fH°_gas : Enthalpy of formation at standard conditions (kJ/mol).
• Δ_fH°_liquid : Liquid phase enthalpy of formation at standard conditions (kJ/mol).
• Δ_fusH° : Enthalpy of fusion at standard conditions (kJ/mol).
• Δ_vapH° : Enthalpy of vaporization at standard conditions (kJ/mol).
• Δ_vapH : Enthalpy of vaporization at a given temperature (kJ/mol).
• IE : Ionization energy (eV).
• log₁₀WS : Log10 of Water solubility in mol/l.
• logP_oct/wat : Octanol/Water partition coefficient.
• McVol : McGowan's characteristic volume (ml/mol).
• P_c : Critical Pressure (kPa).
• P_vap : Vapor pressure (kPa).
• n₀ : Refractive Index.
• ρ_l : Liquid Density (kg/m³).
• I_np : Non-polar retention indices.
• I_p : Polar retention indices.
• γ : Surface Tension (N/m).
• T_boil : Normal Boiling Point Temperature (K).
• T_boilr : Boiling point at reduced pressure (K).
• T_c : Critical Temperature (K).
• T_fus : Normal melting (fusion) point (K).
• V_c : Critical Volume (m³/kmol).
• ¹: Molecular weight from the IUPAC atomic weights tables.

Physical Properties

Property	Value	Unit	Source
ω	0.4722		Relay (1.0) Calculated Property
ΔcH°liquid	[-3178.10; -3149.76]	kJ/mol
ΔcH°liquid	-3149.76 ± 0.76	kJ/mol	NIST
ΔcH°liquid	-3178.10 ± 7.70	kJ/mol	NIST
ΔcH°liquid	-3153.00	kJ/mol	NIST
ΔfG°	-439.65	kJ/mol	Joback Calculated Property
ΔfH°gas	[-586.20; -507.50]	kJ/mol
ΔfH°gas	-586.20 ± 1.50	kJ/mol	NIST
ΔfH°gas	-558.00	kJ/mol	NIST
ΔfH°gas	-507.50	kJ/mol	NIST
ΔfH°liquid	[-640.40; -561.70]	kJ/mol
ΔfH°liquid	-640.40 ± 1.10	kJ/mol	NIST
ΔfH°liquid	-612.20 ± 5.40	kJ/mol	NIST
ΔfH°liquid	-561.70	kJ/mol	NIST
ΔfusH°	17.26	kJ/mol	Joback Calculated Property
ΔvapH°	[50.54; 54.20]	kJ/mol
ΔvapH°	54.18 ± 0.96	kJ/mol	NIST
ΔvapH°	54.20	kJ/mol	NIST
ΔvapH°	54.20 ± 1.00	kJ/mol	NIST
ΔvapH°	50.54	kJ/mol	NIST
IE	9.53	eV	Relay (1.0) Calculated Property
log10WS	-0.22		Relay (1.0) Calculated Property
logPoct/wat	0.529		Crippen Calculated Property
McVol	104.410	ml/mol	McGowan Calculated Property
Pc	3356.75	kPa	Joback Calculated Property
Inp	[903.00; 954.00]
Inp	903.00		NIST
Inp	910.00		NIST
Inp	954.00		NIST
Inp	944.00		NIST
Inp	907.00		NIST
Inp	910.00		NIST
Inp	907.00		NIST
Inp	944.40		NIST
Inp	943.00		NIST
Inp	930.00		NIST
Inp	954.00		NIST
Ip	[1427.00; 1496.00]
Ip	1496.00		NIST
Ip	1466.00		NIST
Ip	1427.00		NIST
Ip	1496.00		NIST
Ip	1427.00		NIST
Tboil	[453.55; 457.00]	K
Tboil	453.60	K	NIST
Tboil	Outlier 457.00	K	NIST
Tboil	454.00 ± 3.00	K	NIST
Tboil	454.05	K	NIST
Tboil	453.60 ± 1.00	K	NIST
Tboil	453.55 ± 0.50	K	NIST
Tboil	453.60 ± 0.50	K	NIST
Tboil	453.60 ± 0.50	K	NIST
Tboil	453.60 ± 0.50	K	NIST
Tboil	454.15 ± 1.50	K	NIST
Tboil	454.05 ± 2.00	K	NIST
Tc	636.78	K	Relay (1.0) Calculated Property
Tfus	[230.15; 230.15]	K
Tfus	230.15	K	Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) Compiled value
Tfus	230.15	K	NIST
Vc	0.394	m3/kmol	Relay (1.0) Calculated Property

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
Cp,liquid	[241.80; 250.20]	J/mol×K	[297.50; 298.00]
Cp,liquid	250.20	J/mol×K	297.50	NIST
Cp,liquid	246.90	J/mol×K	297.50	NIST
Cp,liquid	241.80	J/mol×K	298.00	NIST
η	[0.0011440; 0.0019020]	Pa×s	[288.15; 318.15]
η	0.0019020	Pa×s	288.15	Densities and Viscosities of Binary Mixtures of Ethyl Acetoacetate, Ethyl Isovalerate, Methyl Benzoate, Benzyl Acetate, Ethyl Salicylate, and Benzyl Propionate with Ethanol at T ) (288.15, 298.15, 308.15, and 318.15) K
η	0.0015810	Pa×s	298.15	Densities and Viscosities of Binary Mixtures of Ethyl Acetoacetate, Ethyl Isovalerate, Methyl Benzoate, Benzyl Acetate, Ethyl Salicylate, and Benzyl Propionate with Ethanol at T ) (288.15, 298.15, 308.15, and 318.15) K
η	0.0013440	Pa×s	308.15	Densities and Viscosities of Binary Mixtures of Ethyl Acetoacetate, Ethyl Isovalerate, Methyl Benzoate, Benzyl Acetate, Ethyl Salicylate, and Benzyl Propionate with Ethanol at T ) (288.15, 298.15, 308.15, and 318.15) K
η	0.0011440	Pa×s	318.15	Densities and Viscosities of Binary Mixtures of Ethyl Acetoacetate, Ethyl Isovalerate, Methyl Benzoate, Benzyl Acetate, Ethyl Salicylate, and Benzyl Propionate with Ethanol at T ) (288.15, 298.15, 308.15, and 318.15) K
ΔvapH	[52.50; 61.60]	kJ/mol	[298.15; 377.50]
ΔvapH	61.60	kJ/mol	298.15	Thermochemistry of Ethyl 3-Oxobutanoate Revisited: Observance of a Non-Zero Enthalpy of Mixing between Tautomers and Its Effects on Enthalpies of Formation
ΔvapH	52.50	kJ/mol	377.50	NIST
n0	[1.41200; 1.41660]		[298.15; 308.15]
n0	1.41660		298.15	Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of 1,4-Dioxane + Ethyl Acetoacetate, + Diethyl Oxalate, + Diethyl Phthalate, or + Dioctyl Phthalate at 298.15, 303.15, and 308.15 K
n0	1.41450		303.15	Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of 1,4-Dioxane + Ethyl Acetoacetate, + Diethyl Oxalate, + Diethyl Phthalate, or + Dioctyl Phthalate at 298.15, 303.15, and 308.15 K
n0	1.41200		308.15	Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of 1,4-Dioxane + Ethyl Acetoacetate, + Diethyl Oxalate, + Diethyl Phthalate, or + Dioctyl Phthalate at 298.15, 303.15, and 308.15 K
ρl	[971.40; 1043.10]	kg/m3	[278.15; 348.15]
ρl	1043.10	kg/m3	278.15	Excess molar enthalpies of ethyl acetoacetate + (methanol, +ethanol, +1-propanol, and +2-propanol) at T = (298.15, 313.15 and 328.15)K and p = (0.1 and 10.0)MPa
ρl	1034.50	kg/m3	288.15	Excess molar enthalpies of ethyl acetoacetate + (methanol, +ethanol, +1-propanol, and +2-propanol) at T = (298.15, 313.15 and 328.15)K and p = (0.1 and 10.0)MPa
ρl	1023.50	kg/m3	298.15	Excess molar enthalpies of ethyl acetoacetate + (methanol, +ethanol, +1-propanol, and +2-propanol) at T = (298.15, 313.15 and 328.15)K and p = (0.1 and 10.0)MPa
ρl	1023.45	kg/m3	298.15	Refractive Indices and Surface Tensions of Binary Mixtures of Ethyl Acetoacetate, Ethyl Isovalerate, Methyl Benzoate, Benzyl Acetate, Ethyl Salicylate, and Benzyl Propionate with Ethanol at (288.15, 298.15, 308.15, and 318.15) K
ρl	1008.00	kg/m3	313.15	Excess molar enthalpies of ethyl acetoacetate + (methanol, +ethanol, +1-propanol, and +2-propanol) at T = (298.15, 313.15 and 328.15)K and p = (0.1 and 10.0)MPa
ρl	992.10	kg/m3	328.15	Excess molar enthalpies of ethyl acetoacetate + (methanol, +ethanol, +1-propanol, and +2-propanol) at T = (298.15, 313.15 and 328.15)K and p = (0.1 and 10.0)MPa
ρl	981.90	kg/m3	338.15	Excess molar enthalpies of ethyl acetoacetate + (methanol, +ethanol, +1-propanol, and +2-propanol) at T = (298.15, 313.15 and 328.15)K and p = (0.1 and 10.0)MPa
ρl	971.40	kg/m3	348.15	Excess molar enthalpies of ethyl acetoacetate + (methanol, +ethanol, +1-propanol, and +2-propanol) at T = (298.15, 313.15 and 328.15)K and p = (0.1 and 10.0)MPa
γ	[0.03; 0.03]	N/m	[288.15; 358.15]
γ	0.03	N/m	288.15	Densities, Viscosities, Refractive Indices, and Surface Tensions for 12 Flavor Esters from T ) 288.15 K to T ) 358.15 K
γ	0.03	N/m	298.15	Densities, Viscosities, Refractive Indices, and Surface Tensions for 12 Flavor Esters from T ) 288.15 K to T ) 358.15 K
γ	0.03	N/m	308.15	Densities, Viscosities, Refractive Indices, and Surface Tensions for 12 Flavor Esters from T ) 288.15 K to T ) 358.15 K
γ	0.03	N/m	318.15	Densities, Viscosities, Refractive Indices, and Surface Tensions for 12 Flavor Esters from T ) 288.15 K to T ) 358.15 K
γ	0.03	N/m	328.15	Densities, Viscosities, Refractive Indices, and Surface Tensions for 12 Flavor Esters from T ) 288.15 K to T ) 358.15 K
γ	0.03	N/m	338.15	Densities, Viscosities, Refractive Indices, and Surface Tensions for 12 Flavor Esters from T ) 288.15 K to T ) 358.15 K
γ	0.03	N/m	348.15	Densities, Viscosities, Refractive Indices, and Surface Tensions for 12 Flavor Esters from T ) 288.15 K to T ) 358.15 K
γ	0.03	N/m	358.15	Densities, Viscosities, Refractive Indices, and Surface Tensions for 12 Flavor Esters from T ) 288.15 K to T ) 358.15 K

Pressure Dependent Properties

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[150.03; 326.00]	J/mol×K	[273.00; 1000.00]	Joback Predicted correlation
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is Cp,gas in J/mol×K, T in K
Coefficient A			3.02020e+01
Coefficient B			4.91040e-01
Coefficient C			-1.89300e-04
Coefficient D			-5.94000e-09
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	150.03	J/mol×K	273.00	Calculated Property
Cp,gas	179.97	J/mol×K	353.78	Calculated Property
Cp,gas	207.35	J/mol×K	434.56	Calculated Property
Cp,gas	232.17	J/mol×K	515.33	Calculated Property
Cp,gas	254.39	J/mol×K	596.11	Calculated Property
Cp,gas	274.01	J/mol×K	676.89	Calculated Property
Cp,gas	290.99	J/mol×K	757.67	Calculated Property
Cp,gas	305.33	J/mol×K	838.44	Calculated Property
Cp,gas	317.01	J/mol×K	919.22	Calculated Property
Cp,gas	326.00	J/mol×K	1000.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
Pvap	[2.98e-04; 3223.24]	kPa	[234.15; 643.00]	KDB Vapor Pressure Data
Equation			ln(Y) = A + B/T + C·ln(T) + D·T² + E/T² Y is Pvap in kPa, T in K
Coefficient A			5.07456e+01
Coefficient B			-7.62332e+03
Coefficient C			-4.83240e+00
Coefficient D			1.05324e-06
Coefficient E			0.00000e+00
Temperature range, min.			234.15
Temperature range, max.			643.00
Pvap	2.98e-04	kPa	234.15	Calculated Property
Pvap	0.03	kPa	279.58	Calculated Property
Pvap	0.58	kPa	325.01	Calculated Property
Pvap	5.63	kPa	370.43	Calculated Property
Pvap	31.66	kPa	415.86	Calculated Property
Pvap	121.69	kPa	461.29	Calculated Property
Pvap	356.19	kPa	506.72	Calculated Property
Pvap	853.23	kPa	552.14	Calculated Property
Pvap	1757.35	kPa	597.57	Calculated Property
Pvap	3223.24	kPa	643.00	Calculated Property
Pvap	[0.13; 102.13]	kPa	[301.70; 454.00]	NIST
Equation			ln(Y) = A + B/(T + C) Y is Pvap in kPa, T in K
Coefficient A			1.64940e+01
Coefficient B			-5.04162e+03
Coefficient C			-2.91840e+01
Reference			Stull, 1947
Comment			Coefficents calculated by NIST from author's data.
Temperature range, min.			301.70
Temperature range, max.			454.00
Pvap	0.13	kPa	301.70	Calculated Property
Pvap	0.40	kPa	318.62	Calculated Property
Pvap	1.04	kPa	335.54	Calculated Property
Pvap	2.46	kPa	352.47	Calculated Property
Pvap	5.34	kPa	369.39	Calculated Property
Pvap	10.77	kPa	386.31	Calculated Property
Pvap	20.40	kPa	403.23	Calculated Property
Pvap	36.56	kPa	420.16	Calculated Property
Pvap	62.42	kPa	437.08	Calculated Property
Pvap	102.13	kPa	454.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
γ	[0.04; 0.02]	N/m	[228.15; 454.15]	Jasper (1972), surface tension of pure liquid compounds Compiled value
Equation			Y = A + B·T + C·T² + D·T³ + E·T⁴ Y is γ in N/m, T in K
Coefficient A			6.21447e-02
Coefficient B			-1.01500e-04
Coefficient C			0.00000e+00
Coefficient D			0.00000e+00
Coefficient E			0.00000e+00
Temperature range, min.			228.15
Temperature range, max.			454.15
γ	0.04	N/m	228.15	Calculated Property
γ	0.04	N/m	253.26	Calculated Property
γ	0.03	N/m	278.37	Calculated Property
γ	0.03	N/m	303.48	Calculated Property
γ	0.03	N/m	328.59	Calculated Property
γ	0.03	N/m	353.71	Calculated Property
γ	0.02	N/m	378.82	Calculated Property
γ	0.02	N/m	403.93	Calculated Property
γ	0.02	N/m	429.04	Calculated Property
γ	0.02	N/m	454.15	Calculated Property

Similar Compounds

Find more compounds similar to Ethyl acetoacetate.

Mixtures

• Ethyl acetoacetate + Methyl Alcohol
• Ethanol + Ethyl acetoacetate
• 1-Propanol + Ethyl acetoacetate
• 2-Propanol + Ethyl acetoacetate
• Ethyl acetoacetate + Water
• Ethyl acetoacetate + 1,4-Dioxane
• 1-Butanol + Ethyl acetoacetate
• Ethyl acetoacetate + 1-Pentanol
• Ethyl acetoacetate + Ethyl Acetate

Sources

• KDB Vapor Pressure Data
• Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) ChEDL chemicals 1.5.2, from Bradley, J.-C.; Williams, A.; Lang, A. Jean-Claude Bradley Open Melting Point Dataset. Figshare, 2014 (CC0).
• Jasper (1972), surface tension of pure liquid compounds ChEDL chemicals 1.5.2, from Jasper, J. J. The Surface Tension of Pure Liquid Compounds. J. Phys. Chem. Ref. Data 1972, 1, 841-1010 (as transcribed in Lange's Handbook).
• Cheméo Relay (1.0)
• Crippen Method
• Crippen Method
• Excess molar enthalpies of ethyl acetoacetate + (methanol, +ethanol, +1-propanol, and +2-propanol) at T = (298.15, 313.15 and 328.15)K and p = (0.1 and 10.0)MPa
• Solute-Solvent Interactions of Alkyl Acetoacetates in Aqueous {1-Butyl-3-Methylimidazolium Bromide [bmim][Br]}Ionic Liquid Solutions in the Temperature Interval (288.15 - 308.15 ) K
• Density, Viscosity, Refractive Index, and Speed of Sound in the Binary Mixtures of 1,4-Dioxane + Ethyl Acetoacetate, + Diethyl Oxalate, + Diethyl Phthalate, or + Dioctyl Phthalate at 298.15, 303.15, and 308.15 K
• Densities, Viscosities, Refractive Indices, and Surface Tensions for 12 Flavor Esters from T ) 288.15 K to T ) 358.15 K
• Thermochemistry of Ethyl 3-Oxobutanoate Revisited: Observance of a Non-Zero Enthalpy of Mixing between Tautomers and Its Effects on Enthalpies of Formation
• Densities and Viscosities of Binary Mixtures of Ethyl Acetoacetate, Ethyl Isovalerate, Methyl Benzoate, Benzyl Acetate, Ethyl Salicylate, and Benzyl Propionate with Ethanol at T ) (288.15, 298.15, 308.15, and 318.15) K
• Refractive Indices and Surface Tensions of Binary Mixtures of Ethyl Acetoacetate, Ethyl Isovalerate, Methyl Benzoate, Benzyl Acetate, Ethyl Salicylate, and Benzyl Propionate with Ethanol at (288.15, 298.15, 308.15, and 318.15) K
• Solute Solvent Interactions of Alkyl Acetoacetates in Aqueous {1-Butyl-3-methylimidazolium Chloride [bmim][Cl]} Ionic Liquid Solutions in the Temperature Interval (288.15 308.15) K
• Excess Molar Enthalpies of Five Binary Systems Containing Ethyl Acetoacetate at Different Temperatures
• Joback Method
• KDB
• McGowan Method
• NIST Webbook

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