Chemical Properties of Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- (CAS 5989-54-8)

InChI

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1

InChI Key

XMGQYMWWDOXHJM-JTQLQIEISA-N

Formula

C10H16

SMILES

C=C(C)C1CC=C(C)CC1

Molecular Weight¹

136.23

CAS

5989-54-8

Other Names

• (+)-(4R)-limonene
• (+)-.alpha.-limonene
• (+)-4-isopropenyl-1-methylcyclohexene
• (+)-dipentene
• (+)-limonene
• (+)-p-mentha-1,8-diene
• (-)-Limonene
• (4R)-(+)-limonene
• (R)-(+)-limonene
• (R)-(+)-p-mentha-1,8-diene
• (R)-1-methyl-4-(1-methylethenyl)cyclohexene
• (R)-4-isopropenyl-1-methyl-1-cyclohexene
• (R)-limonene
• (R)-p-mentha-1,8-diene
• (S)-p-mentha-1,8-diene
• D-(+)-limonene
• D-limonene
• L-Limonene
• Limonene
• carvene
• cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-,
• limonene, (+)-
• p-Mentha-1,8-diene, (S)-(-)-
• p-mentha-1,8-diene, (R)-(+)-

• ω : Acentric Factor.
• C_p,gas : Ideal gas 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_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.

Contents

1. Physical Properties
2. Temperature Dependent Properties
3. Datasets
4. Correlations
5. Similar Compounds
6. Mixtures
7. Sources

Physical Properties

Property	Value	Unit	Source
ω	0.2512		Relay (1.0) Calculated Property
ΔfG°	157.39	kJ/mol	Joback Calculated Property
ΔfH°gas	39.83	kJ/mol	Relay (1.0) Calculated Property
ΔfusH°	11.73	kJ/mol	Joback Calculated Property
ΔvapH°	49.00 ± 0.10	kJ/mol	NIST
IE	8.54	eV	Relay (1.0) Calculated Property
log10WS	-4.06		Relay (1.0) Calculated Property
logPoct/wat	3.309		Crippen Calculated Property
McVol	132.300	ml/mol	McGowan Calculated Property
Pc	2755.56	kPa	Joback Calculated Property
Inp	[1014.00; 1055.00]
Inp	1027.00		NIST
Inp	Outlier 1055.00		NIST
Inp	1031.00		NIST
Inp	1031.00		NIST
Inp	1014.00		NIST
Inp	1020.00		NIST
Inp	1014.00		NIST
Inp	1031.00		NIST
I	[1183.00; 1208.00]
I	1208.00		NIST
I	1193.00		NIST
I	1183.00		NIST
I	1199.00		NIST
I	1199.00		NIST
I	1204.00		NIST
I	1208.00		NIST
Tboil	[449.00; 450.00]	K
Tboil	449.20	K	NIST
Tboil	449.40 ± 2.00	K	NIST
Tboil	449.40 ± 3.00	K	NIST
Tboil	450.00 ± 6.00	K	NIST
Tboil	449.00 ± 4.00	K	NIST
Tc	630.74	K	Relay (1.0) Calculated Property
Tfus	203.55	K	Relay (1.0) Calculated Property
Vc	0.457	m3/kmol	Relay (1.0) Calculated Property

Temperature Dependent Properties

Property	Value	Unit	Temperature (K)	Source
Cp,gas	[269.80; 362.36]	J/mol×K	[448.45; 657.16]
Cp,gas	269.80	J/mol×K	448.45	Joback Calculated Property
Cp,gas	287.42	J/mol×K	483.23	Joback Calculated Property
Cp,gas	304.13	J/mol×K	518.02	Joback Calculated Property
Cp,gas	319.94	J/mol×K	552.80	Joback Calculated Property
Cp,gas	334.90	J/mol×K	587.59	Joback Calculated Property
Cp,gas	349.03	J/mol×K	622.37	Joback Calculated Property
Cp,gas	362.36	J/mol×K	657.16	Joback Calculated Property
η	[0.0003820; 0.0010780]	Pa×s	[283.15; 373.15]
η	0.0010780	Pa×s	283.15	Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
η	0.0009020	Pa×s	293.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
η	0.0009320	Pa×s	293.15	Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
η	0.0008900	Pa×s	298.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
η	0.0008970	Pa×s	298.15	Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
η	0.0007930	Pa×s	303.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
η	0.0008160	Pa×s	303.15	Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
η	0.0007020	Pa×s	313.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
η	0.0007220	Pa×s	313.15	Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
η	0.0006280	Pa×s	323.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
η	0.0006450	Pa×s	323.15	Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
η	0.0005660	Pa×s	333.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
η	0.0005800	Pa×s	333.15	Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
η	0.0005000	Pa×s	343.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
η	0.0005240	Pa×s	343.15	Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
η	0.0004520	Pa×s	353.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
η	0.0004760	Pa×s	353.15	Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
η	0.0004130	Pa×s	363.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
η	0.0003820	Pa×s	373.15	Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
ΔvapH	[45.50; 47.00]	kJ/mol	[333.00; 387.50]
ΔvapH	45.50	kJ/mol	333.00	NIST
ΔvapH	47.00	kJ/mol	387.50	NIST
n0	[1.47081; 1.47300]		[293.20; 298.15]
n0	1.47300		293.20	Vapor Liquid Equilibrium Data for Binary Systems of 1-Methyl-4-(1-methylethenyl)-cyclohexene + {Ethanol, Propan-1-ol, Propan-2-ol, Butan-1-ol, Pentan-1-ol, or Hexan-1-ol} at 40 kPa
n0	1.47081		298.15	Deterpenation of Citrus Essential Oil by Liquid-Liquid Extraction with 1-Alkyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)amide Ionic Liquids
ρl	[837.31; 841.35]	kg/m3	[298.15; 298.20]
ρl	838.68	kg/m3	298.15	Improved concentration of citrus essential oil by solvent extraction with acetate ionic liquids
ρl	837.31	kg/m3	298.15	Ternary and quaternary (liquid + liquid) equilibria for (water + ethanol + a-pinene, +b-pinene, or +limonene) and (water + ethanol + a-pinene + limonene) at the temperature 298.15 K
ρl	837.31	kg/m3	298.15	Temperature dependence on mutual solubility of binary (methanol + limonene) mixture and (liquid + liquid) equilibria of ternary (methanol + ethanol + limonene) mixture
ρl	837.31	kg/m3	298.15	Mutual Solubilities of Terpene in Methanol and Water and Their Multicomponent Liquid-Liquid Equilibria
ρl	841.35	kg/m3	298.20	Fractionation of orange essential oil using liquid-liquid extraction: Equilibrium data for model and real systems at 298.2 K.
ρl	840.73	kg/m3	298.20	Deterpenation of Citrus Essential Oils Using Glycerol-Based Deep Eutectic Solvents
ρl	841.35	kg/m3	298.20	Physical Behavior of the Phases from the Liquid-Liquid Equilibrium of Citrus Essential Oils Systems at 298.2 K

Datasets

Mass density, kg/m3

Fixed		Measured
Temperature, K - Liquid	Pressure, kPa - Liquid	Mass density, kg/m3 - Liquid
283.15	20000.00	862.0
283.15	25000.00	864.9
283.15	30000.00	867.7
283.15	35000.00	870.4
283.15	40000.00	873.3
298.15	20000.00	851.5
298.15	25000.00	854.5
298.15	30000.00	857.6
298.15	35000.00	860.9
298.15	40000.00	863.4
313.15	20000.00	841.0
313.15	25000.00	844.2
313.15	30000.00	847.2
313.15	35000.00	850.3
313.15	40000.00	853.3
328.15	20000.00	830.5
328.15	25000.00	833.8
328.15	30000.00	837.2
328.15	35000.00	840.4
328.15	40000.00	843.8
343.15	20000.00	820.1
343.15	25000.00	823.7
343.15	30000.00	827.3
343.15	35000.00	831.1
343.15	40000.00	834.6
358.15	20000.00	810.2
358.15	25000.00	813.9
358.15	30000.00	817.6
358.15	35000.00	821.3
358.15	40000.00	824.8
Reference

Fixed		Measured
Pressure, kPa - Liquid	Temperature, K - Liquid	Mass density, kg/m3 - Liquid
100.00	298.20	838.59
Reference

Fixed		Measured
Pressure, kPa - Liquid	Temperature, K - Liquid	Mass density, kg/m3 - Liquid
101.80	298.15	838.59
Reference

Fixed		Measured
Temperature, K - Liquid	Pressure, kPa - Liquid	Mass density, kg/m3 - Liquid
298.15	100.00	839.1
Reference

Fixed		Measured
Temperature, K - Liquid	Pressure, kPa - Liquid	Mass density, kg/m3 - Liquid
283.15	20000.00	862.0
283.15	25000.00	864.9
283.15	30000.00	867.7
283.15	35000.00	870.4
283.15	40000.00	873.3
298.15	20000.00	851.5
298.15	25000.00	854.5
298.15	30000.00	857.6
298.15	35000.00	860.9
298.15	40000.00	863.4
313.15	20000.00	841.0
313.15	25000.00	844.2
313.15	30000.00	847.2
313.15	35000.00	850.3
313.15	40000.00	853.3
328.15	20000.00	830.5
328.15	25000.00	833.8
328.15	30000.00	837.2
328.15	35000.00	840.4
328.15	40000.00	843.8
343.15	20000.00	820.1
343.15	25000.00	823.7
343.15	30000.00	827.3
343.15	35000.00	831.1
343.15	40000.00	834.6
358.15	20000.00	810.2
358.15	25000.00	813.9
358.15	30000.00	817.6
358.15	35000.00	821.3
358.15	40000.00	824.8
Reference

Correlations

Property	Value	Unit	Temperature (K)	Source
Pvap	[1.33; 202.67]	kPa	[325.62; 483.49]	The Yaws Handbook of Vapor Pressure
Equation			ln(Pvp) = A + B/(T + C)
Coefficient A			1.35555e+01
Coefficient B			-3.43704e+03
Coefficient C			-6.65700e+01
Temperature range, min.			325.62
Temperature range, max.			483.49
Pvap	1.33	kPa	325.62	Calculated Property
Pvap	3.09	kPa	343.16	Calculated Property
Pvap	6.49	kPa	360.70	Calculated Property
Pvap	12.53	kPa	378.24	Calculated Property
Pvap	22.54	kPa	395.78	Calculated Property
Pvap	38.22	kPa	413.33	Calculated Property
Pvap	61.60	kPa	430.87	Calculated Property
Pvap	95.03	kPa	448.41	Calculated Property
Pvap	141.10	kPa	465.95	Calculated Property
Pvap	202.67	kPa	483.49	Calculated Property

Similar Compounds

Find more compounds similar to Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-.

Mixtures

• 1-Pentanol + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
• Ethanol + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + Water
• Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + Methyl Alcohol
• Ethanol + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + Methyl Alcohol
• Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + «beta»-Pinene
• Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + Water
• Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + Methyl Alcohol + Water
• Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + «alpha»-Pinene
• Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + 1-Hexanol
• Ethanol + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
• 1-Propanol + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
• Isopropyl Alcohol + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
• 1-Butanol + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
• Acetonitrile + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
• Carbon dioxide + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
• Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + Water + Linalool
• Acetone + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + Water
• Acetonitrile + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)- + Water
• Carbon dioxide + Ethanol + Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-

Sources

• Cheméo Relay (1.0)
• Crippen Method
• Crippen Method
• Measurement of activity coefficients at infinite dilution for acetonitrile, water, limonene, limonene epoxide and their binary pairs
• Density, viscosity, vapour liquid equilibrium, excess molar enthalpy, and their correlations of the binary system [1-pentanol + R-(+)-limonene] over the complete concentration range, at different temperatures
• Improved concentration of citrus essential oil by solvent extraction with acetate ionic liquids
• Fractionation of orange essential oil using liquid-liquid extraction: Equilibrium data for model and real systems at 298.2 K.
• Solubility of three natural compounds with insecticidal activity in supercritical carbon dioxide: Experimental measurements and predictive modeling with the GC-EoS
• Ternary and quaternary (liquid + liquid) equilibria for (water + ethanol + a-pinene, +b-pinene, or +limonene) and (water + ethanol + a-pinene + limonene) at the temperature 298.15 K
• (Liquid + liquid) equilibria of (water + linalool + limonene) ternary system at T = (298.15, 308.15, and 318.15) K
• Temperature dependence on mutual solubility of binary (methanol + limonene) mixture and (liquid + liquid) equilibria of ternary (methanol + ethanol + limonene) mixture
• (Ternary liquid + liquid) equilibria for (water + acetone + alpha-pinene, or beta-pinene, or limonene) mixtures
• P, rho, and T measurements of the (limonene + beta-pinene) mixtures
• Deterpenation of eucalyptus essential oil by liquid + liquid extraction: Phase equilibrium and physical properties for model systems at T = 298.2 K
• Viscosities and densities of systems involved in the deterpenation of essential oils by liquid-liquid extraction: New UNIFAC-VISCO parameters
• Deterpenation of Citrus Essential Oils Using Glycerol-Based Deep Eutectic Solvents
• Physical Behavior of the Phases from the Liquid-Liquid Equilibrium of Citrus Essential Oils Systems at 298.2 K
• Physical Properties of Model and Real Systems Composed of Essential Oils and Hydroalcoholic Solvents at 298.2 K and Atmospheric Pressure
• Liquid-Liquid Equilibrium for the Water + Acetonitrile + Limonene System at different temperatures
• Entrainer Effect of Ethanol on High-Pressure Vapor-Liquid Equilibria for Supercritical Carbon Dioxide + Limonene + Linalool System
• Mutual Solubilities of Terpene in Methanol and Water and Their Multicomponent Liquid-Liquid Equilibria
• P, rho, and T Measurements of the Limonene + alpha-Pinene Mixtures
• Deterpenation of Citrus Essential Oil by Liquid-Liquid Extraction with 1-Alkyl-3-methylimidazolium Bis(trifluoromethylsulfonyl)amide Ionic Liquids
• Vapor Liquid Equilibrium Data for Binary Systems of 1-Methyl-4-(1-methylethenyl)-cyclohexene + {Ethanol, Propan-1-ol, Propan-2-ol, Butan-1-ol, Pentan-1-ol, or Hexan-1-ol} at 40 kPa
• Vapor Liquid Equilibria Measurements of Bitter Orange Aroma Compounds Highly Diluted in Boiling Hydro-Alcoholic Solutions at 101.3 kPa
• Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of r-Pinene, d-Limonene, (()-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure
• Joback Method
• McGowan Method
• NIST Webbook
• The Yaws Handbook of Vapor Pressure

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Outlier This icon means that the value is more than 2 standard deviations away from the property mean.