Chemical Properties of Butanedioic acid, dimethyl ester (CAS 106-65-0)

InChI

InChI=1S/C6H10O4/c1-9-5(7)3-4-6(8)10-2/h3-4H2,1-2H3

InChI Key

MUXOBHXGJLMRAB-UHFFFAOYSA-N

Formula

C6H10O4

SMILES

COC(=O)CCC(=O)OC

Molecular Weight¹

146.14

CAS

106-65-0

Other Names

• 1,4-butanedioic acid, dimethyl ester
• CH3OC(O)CH2CH2C(O)OCH3
• DBE-4
• Dimethyl ester of succinic acid
• Dimethylsuccinate
• Methyl succinate
• dimethyl 1,4-butanedioate
• dimethyl butanedioate
• dimethyl succinate
• succinic acid, dimethyl ester

• ω : Acentric Factor.
• Δ_cH°_solid : Standard solid enthalpy of combustion (kJ/mol).
• C_p,gas : Ideal gas heat capacity (J/mol×K).
• η : Dynamic viscosity (Pa×s).
• Δ_fH°_gas : 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.
• 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	0.5386		PSRK revision IV (2005), critical constants and acentric factors of 1000 components Compiled value
ΔcH°solid	-2959.00	kJ/mol	NIST
ΔfH°gas	-778.15	kJ/mol	Relay (1.0) Calculated Property
ΔfusH°	20.03	kJ/mol	Joback Calculated Property
ΔvapH°	[60.90; 62.40]	kJ/mol
ΔvapH°	61.00 ± 0.30	kJ/mol	NIST
ΔvapH°	61.70 ± 0.40	kJ/mol	NIST
ΔvapH°	60.90 ± 0.40	kJ/mol	NIST
ΔvapH°	62.40	kJ/mol	NIST
IE	10.09	eV	Relay (1.0) Calculated Property
log10WS	-0.87		Relay (1.0) Calculated Property
logPoct/wat	0.113		Crippen Calculated Property
McVol	110.280	ml/mol	McGowan Calculated Property
Pc	[3060.00; 3092.78]	kPa
Pc	3060.00	kPa	Vapor Pressures, Enthalpies of Vaporization, and Critical Parameters of a Series of Linear Aliphatic Dimethyl Esters of Dicarboxylic Acids
Pc	3092.78	kPa	PSRK revision IV (2005), critical constants and acentric factors of 1000 components Compiled value
Inp	[169.29; 1035.50]
Inp	1029.00		NIST
Inp	1027.00		NIST
Inp	1026.00		NIST
Inp	997.00		NIST
Inp	995.00		NIST
Inp	994.00		NIST
Inp	999.00		NIST
Inp	1004.00		NIST
Inp	1034.00		NIST
Inp	1000.00		NIST
Inp	1035.50		NIST
Inp	1012.00		NIST
Inp	1014.00		NIST
Inp	1015.00		NIST
Inp	1017.00		NIST
Inp	1034.00		NIST
Inp	1004.00		NIST
Inp	1000.00		NIST
Inp	996.00		NIST
Inp	996.00		NIST
Inp	1030.00		NIST
Inp	1032.00		NIST
Inp	1034.00		NIST
Inp	1035.00		NIST
Inp	1002.00		NIST
Inp	1009.00		NIST
Inp	Outlier 169.29		NIST
Inp	1004.00		NIST
Inp	Outlier 169.29		NIST
Inp	1012.00		NIST
Inp	1034.00		NIST
Inp	1035.50		NIST
Ip	[1526.00; 1595.00]
Ip	1566.00		NIST
Ip	1580.00		NIST
Ip	1595.00		NIST
Ip	1576.00		NIST
Ip	1526.00		NIST
Ip	1568.00		NIST
Ip	1558.00		NIST
Ip	1558.00		NIST
Ip	1595.00		NIST
Ip	1526.00		NIST
Tboil	[468.40; 473.20]	K
Tboil	469.80	K	Liquid liquid equilibria of the ternary system water + acetic acid + dimethyl succinate
Tboil	469.20	K	Liquid-Liquid Equilibria for Ternary Systems of Water + Formic Acid + Dibasic Esters
Tboil	Outlier 473.20	K	NIST
Tboil	469.60	K	NIST
Tboil	469.40 ± 0.80	K	NIST
Tboil	469.60 ± 0.50	K	NIST
Tboil	469.60 ± 0.50	K	NIST
Tboil	469.10 ± 1.00	K	NIST
Tboil	468.50 ± 2.00	K	NIST
Tboil	468.40 ± 2.00	K	NIST
Tc	665.73	K	PSRK revision IV (2005), critical constants and acentric factors of 1000 components Compiled value
Tfus	[290.00; 293.00]	K
Tfus	292.15	K	Jean-Claude Bradley Open Melting Point Dataset (2014, CC0) Compiled value
Tfus	291.70 ± 2.00	K	NIST
Tfus	291.50 ± 0.60	K	NIST
Tfus	291.40 ± 1.00	K	NIST
Tfus	293.00 ± 1.50	K	NIST
Tfus	291.90 ± 0.60	K	NIST
Tfus	291.40 ± 1.50	K	NIST
Tfus	Outlier 290.00 ± 1.00	K	NIST
Tfus	291.40 ± 1.00	K	NIST
Tfus	292.65 ± 0.50	K	NIST
Tfus	291.20 ± 2.00	K	NIST
Tfus	291.70 ± 2.00	K	NIST
Vc	0.420	m3/kmol	PSRK revision IV (2005), critical constants and acentric factors of 1000 components Compiled value

Cheméo can also estimate Standard Gibbs free energy of formation for this compound, but it falls outside the models' validated range, so it is not shown here. Open the prediction tool to compute it on demand.

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
ΔvapH	49.30	kJ/mol	405.00	NIST
Pvap	[2.00; 8.30]	kPa	[363.39; 393.49]
Pvap	2.00	kPa	363.39	Isobaric vapor-liquid equilibrium of three binary systems containing dimethyl succinate, dimethyl glutarate and dimethyl adipate at 2, 5.2 and 8.3 kPa
Pvap	5.20	kPa	382.13	Isobaric vapor-liquid equilibrium of three binary systems containing dimethyl succinate, dimethyl glutarate and dimethyl adipate at 2, 5.2 and 8.3 kPa
Pvap	8.30	kPa	393.49	Isobaric vapor-liquid equilibrium of three binary systems containing dimethyl succinate, dimethyl glutarate and dimethyl adipate at 2, 5.2 and 8.3 kPa
n0	[1.41969; 1.41969]		[293.15; 293.15]
n0	1.41969		293.15	Phase equilibria of (water + levulinic acid + dibasic esters) ternary systems
n0	1.41969		293.15	(Liquid + liquid) equilibria of (water + butyric acid + dibasic esters) ternary systems
n0	1.41969		293.15	(Liquid + liquid) equilibria of (water + propionic acid + dibasic esters) ternary systems

Pressure Dependent Properties

Correlations

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[165.44; 345.09]	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			4.82520e+01
Coefficient B			4.64240e-01
Coefficient C			-1.13400e-04
Coefficient D			-5.40000e-08
Coefficient E			0.00000e+00
Temperature range, min.			273.00
Temperature range, max.			1000.00
Cp,gas	165.44	J/mol×K	273.00	Calculated Property
Cp,gas	195.91	J/mol×K	353.78	Calculated Property
Cp,gas	224.14	J/mol×K	434.56	Calculated Property
Cp,gas	249.98	J/mol×K	515.33	Calculated Property
Cp,gas	273.26	J/mol×K	596.11	Calculated Property
Cp,gas	293.79	J/mol×K	676.89	Calculated Property
Cp,gas	311.41	J/mol×K	757.67	Calculated Property
Cp,gas	325.94	J/mol×K	838.44	Calculated Property
Cp,gas	337.23	J/mol×K	919.22	Calculated Property
Cp,gas	345.09	J/mol×K	1000.00	Calculated Property

Property	Value	Unit	Temperature (K)	Source
η	[0.0018096; 0.0002173]	Pa×s	[291.82; 466.01]	Joback Predicted correlation
Equation			Y = exp(A + B/T + C·ln(T) + D·T^E) Y is η in Pa×s, T in K
Coefficient A			-1.19854e+01
Coefficient B			1.65484e+03
Coefficient C			0.00000e+00
Coefficient D			0.00000e+00
Coefficient E			0.00000e+00
Comment			Liquid phase. Joback/Reid (1987), valid from Tf to 0.7·Tc.
Temperature range, min.			291.82
Temperature range, max.			466.01
η	0.0018096	Pa×s	291.82	Calculated Property
η	0.0012718	Pa×s	311.17	Calculated Property
η	0.0009315	Pa×s	330.53	Calculated Property
η	0.0007061	Pa×s	349.88	Calculated Property
η	0.0005511	Pa×s	369.24	Calculated Property
η	0.0004408	Pa×s	388.59	Calculated Property
η	0.0003602	Pa×s	407.95	Calculated Property
η	0.0002997	Pa×s	427.30	Calculated Property
η	0.0002534	Pa×s	446.66	Calculated Property
η	0.0002173	Pa×s	466.01	Calculated Property

Property	Value	Unit	Temperature (K)	Source
Pvap	[1.33; 202.65]	kPa	[348.75; 497.31]	The Yaws Handbook of Vapor Pressure
Equation			ln(Y) = A + B/(T + C) Y is Pvap in kPa, T in K
Coefficient A			1.65135e+01
Coefficient B			-5.37480e+03
Coefficient C			-1.75020e+01
Temperature range, min.			348.75
Temperature range, max.			497.31
Pvap	1.33	kPa	348.75	Calculated Property
Pvap	2.88	kPa	365.26	Calculated Property
Pvap	5.80	kPa	381.76	Calculated Property
Pvap	11.00	kPa	398.27	Calculated Property
Pvap	19.77	kPa	414.78	Calculated Property
Pvap	33.92	kPa	431.28	Calculated Property
Pvap	55.83	kPa	447.79	Calculated Property
Pvap	88.57	kPa	464.30	Calculated Property
Pvap	135.96	kPa	480.80	Calculated Property
Pvap	202.65	kPa	497.31	Calculated Property

Property	Value	Unit	Temperature (K)	Source
γ	[0.04; 0.02]	N/m	[292.15; 469.55]	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			7.15322e-02
Coefficient B			-1.19100e-04
Coefficient C			0.00000e+00
Coefficient D			0.00000e+00
Coefficient E			0.00000e+00
Temperature range, min.			292.15
Temperature range, max.			469.55
γ	0.04	N/m	292.15	Calculated Property
γ	0.03	N/m	311.86	Calculated Property
γ	0.03	N/m	331.57	Calculated Property
γ	0.03	N/m	351.28	Calculated Property
γ	0.03	N/m	370.99	Calculated Property
γ	0.02	N/m	390.71	Calculated Property
γ	0.02	N/m	410.42	Calculated Property
γ	0.02	N/m	430.13	Calculated Property
γ	0.02	N/m	449.84	Calculated Property
γ	0.02	N/m	469.55	Calculated Property

Similar Compounds

Find more compounds similar to Butanedioic acid, dimethyl ester.

Mixtures

• Pentanoic acid, 4-oxo- + Butanedioic acid, dimethyl ester + Water
• Pentanedioic acid, dimethyl ester + Butanedioic acid, dimethyl ester
• Hexanedioic acid, dimethyl ester + Butanedioic acid, dimethyl ester
• Acetic acid + Butanedioic acid, dimethyl ester + Water
• Butanedioic acid, dimethyl ester + Propanoic acid + Water
• Butanedioic acid, dimethyl ester + Water
• Butanoic acid + Butanedioic acid, dimethyl ester + Water
• Formic acid + Butanedioic acid, dimethyl ester + Water

Sources

• 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).
• PSRK revision IV (2005), critical constants and acentric factors of 1000 components ChEDL chemicals 1.5.2, from Horstmann, S.; Jabłoniec, A.; Krafczyk, J.; Fischer, K.; Gmehling, J. PSRK Group Contribution Equation of State: Comprehensive Revision and Extension IV, Including Critical Constants and α-Function Parameters for 1000 Components. Fluid Phase Equilib. 2005, 227, 157-164.
• Cheméo Relay (1.0)
• Crippen Method
• Crippen Method
• Liquid liquid equilibria of the ternary system water + acetic acid + dimethyl succinate
• Phase equilibria of (water + levulinic acid + dibasic esters) ternary systems
• (Liquid + liquid) equilibria of (water + butyric acid + dibasic esters) ternary systems
• (Liquid + liquid) equilibria of (water + propionic acid + dibasic esters) ternary systems
• Isobaric vapor-liquid equilibrium of three binary systems containing dimethyl succinate, dimethyl glutarate and dimethyl adipate at 2, 5.2 and 8.3 kPa
• Vapor Pressures, Enthalpies of Vaporization, and Critical Parameters of a Series of Linear Aliphatic Dimethyl Esters of Dicarboxylic Acids
• Liquid-Liquid Equilibria for Ternary Systems of Water + Formic Acid + Dibasic Esters
• Joback Method
• McGowan Method
• NIST Webbook
• The Yaws Handbook of Vapor Pressure

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