Dibutoxymethane

Formula: C₉H₂₀O₂
Molecular weight: 160.2539
IUPAC Standard InChI: InChI=1S/C9H20O2/c1-3-5-7-10-9-11-8-6-4-2/h3-9H2,1-2H3
IUPAC Standard InChIKey: QLCJOAMJPCOIDI-UHFFFAOYSA-N
CAS Registry Number: 2568-90-3
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.
Other names: Di-n-butoxymethane; Methane, dibutoxy-; Butane, 1,1'-[methylenebis(oxy)]bis-; Butylal; Dibutyl formal; Formaldehyde dibutyl acetal; Di-n-butyl formal; NSC 241; 1,1'-[methylenebis(oxy)]dibutane
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-501. ± 3.	kJ/mol	Ccb	Skuratov, Strepikheev, et al., 1957	Heat of formation derived by Cox and Pilcher, 1970

Condensed phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-549. ± 2.	kJ/mol	Ccb	Skuratov, Strepikheev, et al., 1957	Heat of formation derived by Cox and Pilcher, 1970
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-5850.5 ± 1.7	kJ/mol	Ccb	Skuratov, Strepikheev, et al., 1957	Reanalyzed by Cox and Pilcher, 1970, Original value = -5852.2 kJ/mol; Combustion for liq at 293 K; Corresponding Δ_fHº_liquid = -549.40 kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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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
DRB - Donald R. Burgess, Jr.

Quantity	Value	Units	Method	Reference	Comment
T_boil	455.0	K	N/A	Timmermans, 1927	Uncertainty assigned by TRC = 0.6 K; source of data not clear; TRC
T_boil	452.6	K	N/A	Timmermans, 1922	Uncertainty assigned by TRC = 0.4 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	214.	K	N/A	Timmermans, 1927	Uncertainty assigned by TRC = 0.3 K; TRC
T_fus	215.05	K	N/A	Timmermans, 1922	Uncertainty assigned by TRC = 0.4 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	48.1	kJ/mol	EB	Palczewska-Tulinska and Szafranski, 2000	Based on data from 363. to 452. K.; AC
Δ_vapH°	48. ± 3.	kJ/mol	E	Skuratov, Strepikheev, et al., 1957	Heat of formation derived by Cox and Pilcher, 1970; ALS
Δ_vapH°	48.0	kJ/mol	N/A	Skuratov, Strepikheev, et al., 1957	DRB

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
47.9	381.	EB	Palczewska-Tulinska and Szafranski, 2000	Based on data from 366. to 452. K.; AC
57.3	293.	V	Skuratov, Strepikheev, et al., 1957	Combustion for liq at 293 K; ALS

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes

Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Shtekhter, S.M.; Volokhina, A.V., About the enthalpies of polymerization of cyclic formales, Dokl. Akad. Nauk SSSR, 1957, 117, 263-265. [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]

Timmermans, 1927
Timmermans, J., The Melting Point of Organic Substances, Bull. Soc. Chim. Belg., 1927, 36, 502. [all data]

Timmermans, 1922
Timmermans, J., Investigation of the Freezing Point of Organic Substances VII, Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]

Palczewska-Tulinska and Szafranski, 2000
Palczewska-Tulinska, Marcela; Szafranski, Andrzej M., Selected Physicochemical Properties of Dibutoxymethane, J. Chem. Eng. Data, 2000, 45, 6, 988-990, https://doi.org/10.1021/je000070l . [all data]

Notes

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Symbols used in this document:

T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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