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
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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -101.5 ± 0.3 | kcal/mol | Cm | Wiberg, Morgan, et al., 1994 | ALS |
| ΔfH°gas | -101.41 ± 0.23 | kcal/mol | Cm | Wiberg and Squires, 1979 | Hydrolysis; ALS |
| ΔfH°gas | -100.8 | kcal/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
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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:
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 | -110.1 ± 0.2 | kcal/mol | Cm | Wiberg, Morgan, et al., 1994 | ALS |
| ΔfH°liquid | -109.82 ± 0.15 | kcal/mol | Cm | Wiberg and Squires, 1979 | Hydrolysis; ALS |
| ΔfH°liquid | -109.24 ± 0.23 | kcal/mol | Cm | Stern and Dorer, 1962 | Reanalyzed by Cox and Pilcher, 1970, Original value = -109.9 ± 0.5 kcal/mol; Heat of hydrolysis; ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 52.03 | 298.15 | Baglay, Gurariy, et al., 1988 | T = 270 to 340 K. Unsmoothed experimental datum.; DH |
| 52.10 | 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
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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° | 8.99 ± 0.1 | kcal/mol | GS | Verevkin, 2002 | Based on data from 272. to 301. K.; AC |
| ΔvapH° | 8.53 | kcal/mol | N/A | Wiberg, Morgan, et al., 1994 | DRB |
| ΔvapH° | 8.430 | kcal/mol | E | Wiberg and Squires, 1979 | Hydrolysis; ALS |
| ΔvapH° | 8.41 | kcal/mol | N/A | Wiberg and Squires, 1979 | DRB |
| ΔvapH° | 7.03 | kcal/mol | V | Stern and Dorer, 1962 | Heat of hydrolysis; ALS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 9.13 ± 0.1 | 272. to 301. | GS | Verevkin, Peng, et al., 1998 | AC |
| 8.44 | 324. | EB | Wiberg, Morgan, et al., 1994 | Based on data from 299. to 348. K.; AC |
| 7.98 ± 0.05 | 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° | 4.86 ± 0.01 | kcal/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase |
| ΔrH° | 4.88 ± 0.01 | kcal/mol | Cm | Wiberg and Squires, 1979, 2 | liquid phase; Heat of hydrolysis |
| ΔrH° | 4.8836 ± 0.0067 | kcal/mol | Cm | Wiberg and Squires, 1979 | liquid phase; solvent: Water; Hydrolysis |
| ΔrH° | -3.95 ± 0.05 | kcal/mol | Cm | Stern and Dorer, 1962 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 3.69 ± 0.05 kcal/mol; Heat of hydrolysis |
2 +
=
+
By formula: 2CH4O + C3H6O = H2O + C5H12O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -11.1 ± 0.3 | kcal/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 |
IR Spectrum
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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: Coblentz Society, Inc.
Condensed Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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| Owner | COBLENTZ SOC. Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | DOW CHEMICAL COMPANY |
| Source reference | COBLENTZ NO. 05788 |
| Date | 1964/03/04 |
| Name(s) | 2,2-dimethoxypropane |
| State | SOLUTION (10% CCl4 FOR 3800-1340, 10% CS2 FOR 1340-450 CM-1) |
| Instrument | DOW KBr FOREPRISM-GRATING |
| Instrument parameters | BLAZED AT 3.5, 12.0, 20.0 MICRON AND CHANGED AT 5.0, 7.5, 14.9 MICRON |
| Path length | 0.011 CM, 0.011 CM SPECTRAL CONTAMINATION DUE TO CCl4 AROUND 1555 CM-1 |
| Resolution | 2 |
| Sampling procedure | TRANSMISSION |
| Data processing | DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| NIST MS number | 20002 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Squalane | 50. | 615. | Becerra, Sánchez, et al., 1982 | N2, Chromosorb W-AM; Column length: 6. m |
| Packed | Squalane | 50. | 616. | Becerra, Sánchez, et al., 1982 | N2, Chromosorb W-AM; Column length: 6. m |
| Packed | Apiezon L | 120. | 620. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
| Packed | Apiezon L | 160. | 627. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 638. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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]
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]
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]
Becerra, Sánchez, et al., 1982
Becerra, M.R.; Sánchez, E.F.; Domínguez, J.A.G.; Muñoz, J.G.; Molera, M.J.,
The use of gaseous and liquid n-paraffins in GC identification of oxidation products of acetondimethyl acetal,
J. Chromatogr. Sci., 1982, 20, 8, 363-366, https://doi.org/10.1093/chromsci/20.8.363
. [all data]
Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S.,
Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Notes
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- Symbols used in this document:
AE Appearance energy 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 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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