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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -425. ± 1. | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | ALS |
| ΔfH°gas | -424.31 ± 0.98 | kJ/mol | Cm | Wiberg and Squires, 1979 | Hydrolysis; ALS |
| ΔfH°gas | -421.9 | kJ/mol | N/A | Stern and Dorer, 1962 | Value computed using ΔfHliquid° value of -457.1±1.0 kj/mol from Stern and Dorer, 1962 and ΔvapH° value of 35.2 kj/mol from Wiberg and Squires, 1979.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -460.7 ± 0.8 | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | ALS |
| ΔfH°liquid | -459.48 ± 0.64 | kJ/mol | Cm | Wiberg and Squires, 1979 | Hydrolysis; ALS |
| ΔfH°liquid | -457.06 ± 0.96 | kJ/mol | Cm | Stern and Dorer, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -460. ± 2. kJ/mol; Heat of hydrolysis; ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 217.7 | 298.15 | Baglay, Gurariy, et al., 1988 | T = 270 to 340 K. Unsmoothed experimental datum.; DH |
| 218.0 | 298.15 | Baglai, Baev, et al., 1984 | T = 273 to 334 K. Cp(liq) = 2.75970 - 0.007898T + 1.9x10-5T2 kJ/kg*K (273 to 334 K).; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, 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:
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 |
References
Go To: Top, Gas phase thermochemistry data, 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.
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
Baglai, Baev, et al., 1984
Baglai, A.K.; Baev, A.A.; Belousov, V.P.; Beregovykh, V.V.; Grushenko, M.M.; Gurarii, L.L.; Konstantinov, S.G.; Kostyushko, Yu.L.; Kuleshov, G.G.; Pasechnik, N.I.; Petrashkevich, R.I.; Podkovyrov, A.I.; Sitnov, A.A.; Shishko, M.A.; Shulgin, I.L.,
Investigation of the physico-chemical characteristics of substances utilized in the synthesis of vitamins A and E,
Khim. Farm. Zhur., 1984, 18, 1013-1019. [all data]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation 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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