α-Pinene
- Formula: C10H16
- Molecular weight: 136.2340
- IUPAC Standard InChIKey: GRWFGVWFFZKLTI-UHFFFAOYSA-N
- CAS Registry Number: 80-56-8
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Species with the same structure:
- Stereoisomers:
- Other names: Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-; 2-Pinene; 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene; Pinene, α; 2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-ene; 2,6,6-Trimethylbicyclo[3.1.1]-2-heptene; Acintene A; 4,6,6-Trimethylbicyklo(3,1,1)hept-3-en; UN 2368; alpha-Pinene; PC 500; Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (.+/-.)-; Sylvapine A; (.+/-.)-α-Pinene; NSC 7727; Pinene; (+)-α-pinene; 2,6,6-trimethylbicyclo[3,1,1]-heptene (α-pinene); α-Pinene [1R-(+), 1S-(-) ]; 2,6,6-trimethylbicyclo-[3,1,1]-2-heptene (α-pinene); pin-2(3)-ene
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Condensed phase thermochemistry data
Go To: Top, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -1483.10 ± 0.70 | kcal/mol | Ccb | Hawkins and Eriksen, 1954 | Reanalyzed by Cox and Pilcher, 1970, Original value = -1483.0 ± 0.25 kcal/mol; Corresponding ΔfHºliquid = -3.93 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Condensed phase thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 430. ± 4. | K | AVG | N/A | Average of 14 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 197.64 | K | N/A | Hawkins and Eriksen. W.T., 1954 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 210.35 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 202.25 | K | N/A | Anonymous, 1942 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 200.75 | K | N/A | Anonymous, 1942 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.9 | kcal/mol | N/A | Clara, Marigliano, et al., 2009 | Based on data from 308. to 427. K.; AC |
ΔvapH° | 10.7 ± 0.02 | kcal/mol | C | An, Hu, et al., 1987 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.2 | 335. | N/A | Rodrigues and Bernardo-Gil, 1996 | Based on data from 320. to 429. K.; AC |
9.61 | 380. | N/A | Reich and Sanhueza, 1993 | Based on data from 365. to 430. K.; AC |
10.8 | 307. | A | Stephenson and Malanowski, 1987 | Based on data from 292. to 433. K.; AC |
10.4 | 308. | N/A | Bukala, Majewski, et al., 1954 | Based on data from 293. to 363. K.; AC |
11.14 | 288. | V | Hawkins and Armstrong, 1954 | ALS |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
292.59 to 428.91 | 3.91590 | 1411.869 | -68.817 | Hawkinds and Armstrong, 1954 | Coefficents calculated by NIST from author's data. |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hawkins and Eriksen, 1954
Hawkins, J.E.; Eriksen, W.T.,
Physical and thermodynamic properties of terpenes. II. The heats of combustion of some terpene hydrocarbons,
J. Am. Chem. Soc., 1954, 76, 2669-26. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Hawkins and Eriksen. W.T., 1954
Hawkins, J.E.; Eriksen. W.T.,
J. Am. Chem. Soc., 1954, 76, 2669. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Anonymous, 1942
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1942. [all data]
Clara, Marigliano, et al., 2009
Clara, Rene A.; Marigliano, Ana C. Gomez; Solimo, Horacio N.,
Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of α-Pinene, d -Limonene, (±)-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure,
J. Chem. Eng. Data, 2009, 54, 3, 1087-1090, https://doi.org/10.1021/je8007414
. [all data]
An, Hu, et al., 1987
An, Xuwu; Hu, Riheng; Wang, Hu; Wu, Mali; Zou, Yongkuang,
Enthalpies of Vaporization of α- and β-Pinene,
Acta Phys. Chim. Sin., 1987, 3, 6, 668-671, https://doi.org/10.3866/PKU.WHXB19870621
. [all data]
Rodrigues and Bernardo-Gil, 1996
Rodrigues, M. Fátima; Bernardo-Gil, M. Gabriela,
Vapor-Liquid Equilibrium Data of α-Pinene + β-Pinene + Limonene at 80 kPa and 101 kPa,
J. Chem. Eng. Data, 1996, 41, 3, 581-585, https://doi.org/10.1021/je950324g
. [all data]
Reich and Sanhueza, 1993
Reich, Ricardo; Sanhueza, Vilma,
Vapor-liquid equilibria for .alpha.-pinene or .beta.-pinene with anisole,
J. Chem. Eng. Data, 1993, 38, 3, 341-343, https://doi.org/10.1021/je00011a001
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Bukala, Majewski, et al., 1954
Bukala, M.; Majewski, J.; Rodzinski, W.,
Przem. Chem., 1954, 10, 6. [all data]
Hawkins and Armstrong, 1954
Hawkins, J.E.; Armstrong, G.T.,
Physical and thermodynamic properties of terpenes. III. The vapor pressures of α-pinene and β-pinene,
J. Am. Chem. Soc., 1954, 76, 3756-37. [all data]
Hawkinds and Armstrong, 1954
Hawkinds, J.E.; Armstrong, G.T.,
Physical and Thermodynamic Properties of Terpenes. III. The Vapor Pressures of α-Pinene and β-Pinene,
J. Am. Chem. Soc., 1954, 76, 14, 3756-3759, https://doi.org/10.1021/ja01643a051
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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