Propane, 2,2-dimethoxy-
- Formula: C5H12O2
- Molecular weight: 104.1476
- IUPAC Standard InChI: InChI=1S/C5H12O2/c1-5(2,6-3)7-4/h1-4H3
- IUPAC Standard InChIKey: HEWZVZIVELJPQZ-UHFFFAOYSA-N
- CAS Registry Number: 77-76-9
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Acetone, dimethyl acetal; Acetone dimethyl ketal; 2,2-Dimethoxypropane
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Phase change data
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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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 356.2 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 353. | K | N/A | American Tokyo Kasei, 1988 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 37.6 ± 0.4 | kJ/mol | GS | Verevkin, 2002 | Based on data from 272. to 301. K.; AC |
| ΔvapH° | 35.7 | kJ/mol | N/A | Wiberg, Morgan, et al., 1994 | DRB |
| ΔvapH° | 35.27 | kJ/mol | E | Wiberg and Squires, 1979 | Hydrolysis; ALS |
| ΔvapH° | 35.2 | kJ/mol | N/A | Wiberg and Squires, 1979 | DRB |
| ΔvapH° | 29.4 | kJ/mol | V | Stern and Dorer, 1962 | Heat of hydrolysis; ALS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 38.2 ± 0.4 | 272. to 301. | GS | Verevkin, Peng, et al., 1998 | AC |
| 35.3 | 324. | EB | Wiberg, Morgan, et al., 1994 | Based on data from 299. to 348. K.; AC |
| 33.4 ± 0.2 | 325. | N/A | Baglay, Gurariy, et al., 1988 | Based on data from 292. to 357. K.; AC |
Reaction thermochemistry data
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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
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
+
= 2
+
By formula: H2O + C5H12O2 = 2CH4O + C3H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 20.3 ± 0.04 | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase |
| ΔrH° | 20.43 ± 0.04 | kJ/mol | Cm | Wiberg and Squires, 1979, 2 | liquid phase; Heat of hydrolysis |
| ΔrH° | 20.433 ± 0.028 | kJ/mol | Cm | Wiberg and Squires, 1979 | liquid phase; solvent: Water; Hydrolysis |
| ΔrH° | -16.5 ± 0.2 | kJ/mol | Cm | Stern and Dorer, 1962 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 15.4 ± 0.2 kJ/mol; Heat of hydrolysis |
2 +
=
+
By formula: 2CH4O + C3H6O = H2O + C5H12O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -46. ± 1. | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | gas phase |
Gas phase ion energetics data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C4H9O+ | 10.28 ± 0.05 | CH3O | EI | Martin, Lampe, et al., 1966 |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
American Tokyo Kasei, 1988
American Tokyo Kasei,
TCI American Organic Chemical 88/89 Catalog, American Tokyo Kasei, Portland, OR, 1988, 1610. [all data]
Verevkin, 2002
Verevkin, Sergey P.,
Improved Benson Increments for the Estimation of Standard Enthalpies of Formation and Enthalpies of Vaporization of Alkyl Ethers, Acetals, Ketals, and Ortho Esters,
J. Chem. Eng. Data, 2002, 47, 5, 1071-1097, https://doi.org/10.1021/je020023o
. [all data]
Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H.,
Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria,
J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]
Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R.,
A microprocessor-controlled system for precise measurement of temperature changes. Determination of the enthalpies of hydrolysis of some polyoxygenated hydrocarbons,
J. Chem. Thermodyn., 1979, 11, 773-786. [all data]
Stern and Dorer, 1962
Stern, J.H.; Dorer, F.H.,
Standard heats of formation of 2,2-Dimethoxypropane (1), and 2,2 -Diethoxypropane (1). Group additivity theory and calculated heats of formation and five ketals,
J. Phys. Chem., 1962, 66, 97-99. [all data]
Verevkin, Peng, et al., 1998
Verevkin, S.P.; Peng, W.-H.; Beckhaus, H.D.; Rücuardt, C.,
Geminal substituent effects. 16. Does the anomeric effect in ketals depend on the hybridization of the central carbon atom?,
Eur. J. Org. Chem., 1998, 11, 2323. [all data]
Baglay, Gurariy, et al., 1988
Baglay, A.K.; Gurariy, L.L.; Kuleshov, G.G.,
Physical properties of compounds used in vitamin synthesis,
J. Chem. Eng. Data, 1988, 33, 512-518. [all data]
Wiberg and Squires, 1979, 2
Wiberg, K.B.; Squires, R.R.,
Thermodynamics of hydrolysis aliphatic ketals. An entropy component of steric effects,
J. Am. Chem. Soc., 1979, 101, 5512-5515. [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]
Martin, Lampe, et al., 1966
Martin, R.H.; Lampe, F.W.; Taft, R.W.,
An electron-impact study of ionization and dissociation in methoxy- and halogen- substituted methanes,
J. Am. Chem. Soc., 1966, 88, 1353. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point ΔrH° Enthalpy of reaction 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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