Chemical Properties of Diethyl malonate (CAS 105-53-3)

InChI

InChI=1S/C7H12O4/c1-3-10-6(8)5-7(9)11-4-2/h3-5H2,1-2H3

InChI Key

IYXGSMUGOJNHAZ-UHFFFAOYSA-N

Formula

C7H12O4

SMILES

CCOC(=O)CC(=O)OCC

Molecular Weight¹

160.17

CAS

105-53-3

Other Names

• 1,3-propanedioic acid, diethyl ester
• Carbethoxyacetic ester
• Dicarbethoxymethane
• Ethyl malonate
• Malonic acid diethylester
• Malonic ester
• Methanedicarboxylic acid, diethyl ester
• NSC 8864
• Propanedioic acid, 1,3-diethyl ester
• Propanedioic acid, diethyl ester
• diethyl 1,3-propanedioate
• diethyl propanedioate
• malonic acid, diethyl ester

• 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 : Polar retention indices.
• T_boil : Normal Boiling Point Temperature (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	0.5546		Relay (1.0) Calculated Property
ΔcH°liquid	-3483.00 ± 4.10	kJ/mol	NIST
ΔfG°	-612.68	kJ/mol	Joback Calculated Property
ΔfH°gas	-921.70 ± 4.20	kJ/mol	NIST
ΔfH°liquid	-986.60 ± 4.20	kJ/mol	NIST
ΔfusH°	22.62	kJ/mol	Joback Calculated Property
ΔvapH°	[64.70; 64.90]	kJ/mol
ΔvapH°	64.70 ± 0.20	kJ/mol	NIST
ΔvapH°	64.90	kJ/mol	NIST
IE	10.00	eV	Relay (1.0) Calculated Property
log10WS	[-0.82; -0.82]
log10WS	-0.82		Aq. Solubility Prediction
log10WS	-0.82		Estimated Solubility
logPoct/wat	0.503		Crippen Calculated Property
McVol	124.370	ml/mol	McGowan Calculated Property
Pc	2829.33	kPa	Joback Calculated Property
Inp	[1029.00; 1083.00]
Inp	1069.00		NIST
Inp	1040.00		NIST
Inp	1033.00		NIST
Inp	1078.00		NIST
Inp	1033.00		NIST
Inp	1033.30		NIST
Inp	1078.00		NIST
Inp	1083.00		NIST
Inp	1038.00		NIST
Inp	1068.80		NIST
Inp	1069.20		NIST
Inp	1035.00		NIST
Inp	1066.90		NIST
Inp	1069.00		NIST
Inp	1034.00		NIST
Inp	1032.00		NIST
Inp	1029.00		NIST
Inp	1033.00		NIST
Inp	1069.00		NIST
Inp	1032.00		NIST
Inp	1069.00		NIST
Inp	1072.00		NIST
Inp	1043.00		NIST
Inp	1043.00		NIST
Inp	1064.00		NIST
Inp	1040.00		NIST
Inp	1035.00		NIST
Inp	1038.00		NIST
Inp	1066.90		NIST
Inp	1034.00		NIST
I	[1542.00; 1595.00]
I	1595.00		NIST
I	1580.00		NIST
I	1572.00		NIST
I	1574.00		NIST
I	1574.00		NIST
I	1571.00		NIST
I	1572.00		NIST
I	1572.00		NIST
I	1582.00		NIST
I	Outlier 1542.00		NIST
I	1595.00		NIST
I	1574.00		NIST
I	1571.00		NIST
I	1580.00		NIST
I	1572.00		NIST
Tboil	[373.35; 473.05]	K
Tboil	473.05	K	Ternary phase diagrams for aqueous mixtures of butyric acid with several solvents: experimental and correlated data
Tboil	472.50	K	NIST
Tboil	373.35 ± 0.40	K	NIST
Tboil	472.05 ± 0.30	K	NIST
Tc	651.00	K	Critical temperatures and pressures of some dicarboxylic acid diethyl esters
Tfus	[221.70; 224.30]	K
Tfus	221.70 ± 0.50	K	NIST
Tfus	224.30 ± 1.00	K	NIST
Tfus	223.25 ± 0.30	K	NIST
Vc	0.485	m3/kmol	Relay (1.0) Calculated Property

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[271.06; 330.10]	J/mol×K	[476.20; 655.96]
Cp,gas	271.06	J/mol×K	476.20	Joback Calculated Property
Cp,gas	281.96	J/mol×K	506.16	Joback Calculated Property
Cp,gas	292.44	J/mol×K	536.12	Joback Calculated Property
Cp,gas	302.51	J/mol×K	566.08	Joback Calculated Property
Cp,gas	312.14	J/mol×K	596.04	Joback Calculated Property
Cp,gas	321.34	J/mol×K	626.00	Joback Calculated Property
Cp,gas	330.10	J/mol×K	655.96	Joback Calculated Property
Cp,liquid	[284.90; 300.20]	J/mol×K	[294.60; 298.15]
Cp,liquid	284.90	J/mol×K	294.60	NIST
Cp,liquid	284.90	J/mol×K	294.60	NIST
Cp,liquid	300.20	J/mol×K	298.15	NIST
η	[0.0002204; 0.0055821]	Pa×s	[253.31; 476.20]
η	0.0055821	Pa×s	253.31	Joback Calculated Property
η	0.0023083	Pa×s	290.46	Joback Calculated Property
η	0.0011661	Pa×s	327.61	Joback Calculated Property
η	0.0006770	Pa×s	364.75	Joback Calculated Property
η	0.0004346	Pa×s	401.90	Joback Calculated Property
η	0.0003008	Pa×s	439.05	Joback Calculated Property
η	0.0002204	Pa×s	476.20	Joback Calculated Property
ΔvapH	[51.20; 64.70]	kJ/mol	[303.00; 426.00]
ΔvapH	64.70 ± 0.20	kJ/mol	303.00	NIST
ΔvapH	64.70 ± 0.20	kJ/mol	303.00	NIST
ΔvapH	63.30	kJ/mol	305.50	NIST
ΔvapH	51.20	kJ/mol	392.50	NIST
ΔvapH	59.90	kJ/mol	426.00	NIST
Pvap	[1.44e-03; 0.10]	kPa	[265.15; 316.30]
Pvap	1.44e-03	kPa	265.15	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	1.89e-03	kPa	267.65	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	1.94e-03	kPa	269.05	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	2.41e-03	kPa	270.55	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	2.55e-03	kPa	271.65	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	3.38e-03	kPa	272.85	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	3.28e-03	kPa	274.15	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	4.36e-03	kPa	275.65	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	4.46e-03	kPa	276.75	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	5.46e-03	kPa	277.85	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	6.37e-03	kPa	279.85	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	7.97e-03	kPa	282.85	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	6.89e-03	kPa	283.80	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	9.15e-03	kPa	284.55	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	8.58e-03	kPa	286.20	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.01	kPa	287.95	Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
Pvap	0.01	kPa	289.20	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.01	kPa	292.30	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.02	kPa	295.20	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.03	kPa	298.20	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.03	kPa	301.30	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.04	kPa	304.20	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.04	kPa	304.70	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.05	kPa	307.30	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.06	kPa	310.20	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.08	kPa	313.30	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
Pvap	0.10	kPa	316.30	Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
n0	[1.40850; 1.41400]		[293.15; 308.15]
n0	1.41400		293.15	Bubble points measurement for (triethyl orthoformate + diethyl malonate)
n0	1.41320		298.15	Density, Viscosity, Refractive Index, and Speed of Sound for Binary Mixtures of 1,4-Dioxane with Different Organic Liquids at (298.15, 303.15, and 308.15) K
n0	1.41080		303.15	Density, Viscosity, Refractive Index, and Speed of Sound for Binary Mixtures of 1,4-Dioxane with Different Organic Liquids at (298.15, 303.15, and 308.15) K
n0	1.40850		308.15	Density, Viscosity, Refractive Index, and Speed of Sound for Binary Mixtures of 1,4-Dioxane with Different Organic Liquids at (298.15, 303.15, and 308.15) K
ρl	[984.70; 1071.04]	kg/m3	[278.15; 358.15]
ρl	1071.04	kg/m3	278.15	Excess Molar Enthalpies of Diethyl Malonate + (Methanol, + Ethanol, + 1-Propanol, and + 2-Propanol) at T = (288.2, 298.2, 313.2, and 328.2) K and p = 101.3 kPa
ρl	1060.33	kg/m3	288.14	Excess Molar Enthalpies of Diethyl Malonate + (Methanol, + Ethanol, + 1-Propanol, and + 2-Propanol) at T = (288.2, 298.2, 313.2, and 328.2) K and p = 101.3 kPa
ρl	1060.33	kg/m3	288.15	Excess molar enthalpies of diethyl malonate+ (1-butanol, 2-methyl-1-propanol, 1-pentanol, n-heptane, and ethyl acetate) at T= (288.2, 298.2, 313.2, 328.2, 338.2, and 348.2 K) and p = 101.3 kPa
ρl	1060.33	kg/m3	288.15	Excess Molar Volumes of 1,3-Diethyl Propanedioate with Methanol, Ethanol, Propan-1-ol, Propan-2-ol, Butan-2-ol, 2-Methyl-propan-1-ol, and Pentan-1-ol at T = (288.15, 298.15, 313.15, and 328.15) K
ρl	1055.25	kg/m3	293.20	Modeling extraction equilibria of butyric acid distributed between water and tri-n-butyl amine/diluent or tri-n-butyl phosphate/diluent system: Extension of the LSER approach
ρl	1049.60	kg/m3	298.15	Excess Molar Volumes of 1,3-Diethyl Propanedioate with Methanol, Ethanol, Propan-1-ol, Propan-2-ol, Butan-2-ol, 2-Methyl-propan-1-ol, and Pentan-1-ol at T = (288.15, 298.15, 313.15, and 328.15) K
ρl	1049.60	kg/m3	298.15	Excess molar enthalpies of diethyl malonate+ (1-butanol, 2-methyl-1-propanol, 1-pentanol, n-heptane, and ethyl acetate) at T= (288.2, 298.2, 313.2, 328.2, 338.2, and 348.2 K) and p = 101.3 kPa
ρl	1049.60	kg/m3	298.15	Excess Molar Enthalpies of Diethyl Malonate + (Methanol, + Ethanol, + 1-Propanol, and + 2-Propanol) at T = (288.2, 298.2, 313.2, and 328.2) K and p = 101.3 kPa
ρl	1033.50	kg/m3	313.15	Excess Molar Volumes of 1,3-Diethyl Propanedioate with Methanol, Ethanol, Propan-1-ol, Propan-2-ol, Butan-2-ol, 2-Methyl-propan-1-ol, and Pentan-1-ol at T = (288.15, 298.15, 313.15, and 328.15) K
ρl	1033.50	kg/m3	313.15	Excess molar enthalpies of diethyl malonate+ (1-butanol, 2-methyl-1-propanol, 1-pentanol, n-heptane, and ethyl acetate) at T= (288.2, 298.2, 313.2, 328.2, 338.2, and 348.2 K) and p = 101.3 kPa
ρl	1033.50	kg/m3	313.15	Excess Molar Enthalpies of Diethyl Malonate + (Methanol, + Ethanol, + 1-Propanol, and + 2-Propanol) at T = (288.2, 298.2, 313.2, and 328.2) K and p = 101.3 kPa
ρl	1017.34	kg/m3	328.15	Excess Molar Volumes of 1,3-Diethyl Propanedioate with Methanol, Ethanol, Propan-1-ol, Propan-2-ol, Butan-2-ol, 2-Methyl-propan-1-ol, and Pentan-1-ol at T = (288.15, 298.15, 313.15, and 328.15) K
ρl	1017.34	kg/m3	328.15	Excess molar enthalpies of diethyl malonate+ (1-butanol, 2-methyl-1-propanol, 1-pentanol, n-heptane, and ethyl acetate) at T= (288.2, 298.2, 313.2, 328.2, 338.2, and 348.2 K) and p = 101.3 kPa
ρl	1017.34	kg/m3	328.15	Excess Molar Enthalpies of Diethyl Malonate + (Methanol, + Ethanol, + 1-Propanol, and + 2-Propanol) at T = (288.2, 298.2, 313.2, and 328.2) K and p = 101.3 kPa
ρl	1006.50	kg/m3	338.15	Excess molar enthalpies of diethyl malonate+ (1-butanol, 2-methyl-1-propanol, 1-pentanol, n-heptane, and ethyl acetate) at T= (288.2, 298.2, 313.2, 328.2, 338.2, and 348.2 K) and p = 101.3 kPa
ρl	1006.50	kg/m3	338.15	Excess Molar Enthalpies of Diethyl Malonate + (Methanol, + Ethanol, + 1-Propanol, and + 2-Propanol) at T = (288.2, 298.2, 313.2, and 328.2) K and p = 101.3 kPa
ρl	995.63	kg/m3	348.15	Excess molar enthalpies of diethyl malonate+ (1-butanol, 2-methyl-1-propanol, 1-pentanol, n-heptane, and ethyl acetate) at T= (288.2, 298.2, 313.2, 328.2, 338.2, and 348.2 K) and p = 101.3 kPa
ρl	995.63	kg/m3	348.15	Excess Molar Enthalpies of Diethyl Malonate + (Methanol, + Ethanol, + 1-Propanol, and + 2-Propanol) at T = (288.2, 298.2, 313.2, and 328.2) K and p = 101.3 kPa
ρl	984.70	kg/m3	358.15	Excess Molar Enthalpies of Diethyl Malonate + (Methanol, + Ethanol, + 1-Propanol, and + 2-Propanol) at T = (288.2, 298.2, 313.2, and 328.2) K and p = 101.3 kPa

Datasets

Viscosity, Pa*s

Fixed		Measured
Temperature, K - Liquid	Pressure, kPa - Liquid	Viscosity, Pa*s - Liquid
303.15	101.30	0.0017
Reference

Correlations

Property	Value	Unit	Temperature (K)	Source
Pvap	[0.13; 101.94]	kPa	[313.15; 472.15]	KDB Vapor Pressure Data
Equation			ln(Pvp) = A + B/T + C*ln(T) + D*T^2
Coefficient A			7.36189e+00
Coefficient B			-5.71086e+03
Coefficient C			1.55030e+00
Coefficient D			-8.41809e-07
Temperature range, min.			313.15
Temperature range, max.			472.15
Pvap	0.13	kPa	313.15	Calculated Property
Pvap	0.37	kPa	330.82	Calculated Property
Pvap	0.95	kPa	348.48	Calculated Property
Pvap	2.23	kPa	366.15	Calculated Property
Pvap	4.87	kPa	383.82	Calculated Property
Pvap	9.94	kPa	401.48	Calculated Property
Pvap	19.11	kPa	419.15	Calculated Property
Pvap	34.90	kPa	436.82	Calculated Property
Pvap	60.88	kPa	454.48	Calculated Property
Pvap	101.94	kPa	472.15	Calculated Property

Similar Compounds

Find more compounds similar to Diethyl malonate.

Mixtures

• Diethyl malonate + 1-Butanol
• Diethyl malonate + 1-Propanol, 2-methyl-
• Diethyl malonate + 1-Pentanol
• Diethyl malonate + Heptane
• Diethyl malonate + Ethyl Acetate
• Diethyl malonate + Propanoic acid + Water
• Diethyl malonate + Formic acid + Water
• Diethyl malonate + Butanoic acid + Water
• Diethyl malonate + Carbon Tetrachloride
• Trichloromethane + Diethyl malonate
• Diethyl malonate + Methyl Alcohol
• Diethyl malonate + Ethanol
• 1-Propanol + Diethyl malonate
• 2-Propanol + Diethyl malonate
• Diethyl malonate + 1,4-Dioxane

Sources

• KDB Vapor Pressure Data
• Cheméo Relay (1.0)
• Crippen Method
• Excess molar enthalpies of diethyl malonate+ (1-butanol, 2-methyl-1-propanol, 1-pentanol, n-heptane, and ethyl acetate) at T= (288.2, 298.2, 313.2, 328.2, 338.2, and 348.2 K) and p = 101.3 kPa
• Separation of propionic acid by diethyl carbonate or diethyl malonate or diethyl fumarate and the synergistic effect of phosphorus compounds and amines
• Liquid phase equilibria of (water + formic acid + diethyl carbonate or diethyl malonate or diethyl fumarate) ternary systems at 298.15K and atmospheric pressure
• Ternary phase diagrams for aqueous mixtures of butyric acid with several solvents: experimental and correlated data
• Modeling extraction equilibria of butyric acid distributed between water and tri-n-butyl amine/diluent or tri-n-butyl phosphate/diluent system: Extension of the LSER approach
• Critical temperatures and pressures of some dicarboxylic acid diethyl esters
• Bubble points measurement for (triethyl orthoformate + diethyl malonate)
• Speeds of sound, isentropic compressibilities, viscosities, and excess molar volumes of binary mixtures of alkanoates with tetra- and trichloromethanes at 303.15 K
• Density, Viscosity, Refractive Index, and Speed of Sound for Binary Mixtures of 1,4-Dioxane with Different Organic Liquids at (298.15, 303.15, and 308.15) K
• Excess Molar Volumes of 1,3-Diethyl Propanedioate with Methanol, Ethanol, Propan-1-ol, Propan-2-ol, Butan-2-ol, 2-Methyl-propan-1-ol, and Pentan-1-ol at T = (288.15, 298.15, 313.15, and 328.15) K
• Vapor Pressures and Enthalpies of Vaporization of a Series of the Symmetric Linear n-Alkyl Esters of Dicarboxylic Acids
• Biomass-Derived Platform Chemicals: Thermodynamic Studies on the Extraction of 5-Hydroxymethylfurfural from Ionic Liquids
• Vapor Pressure of Triethyl and Tri-n-Propyl Phosphates and Diethyl Malonate
• Excess Molar Enthalpies of Diethyl Malonate + (Methanol, + Ethanol, + 1-Propanol, and + 2-Propanol) at T = (288.2, 298.2, 313.2, and 328.2) K and p = 101.3 kPa
• Joback Method
• Aqueous Solubility Prediction Method
• Estimated Solubility Method
• McGowan Method
• NIST Webbook

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