Furfural
- Formula: C5H4O2
- Molecular weight: 96.0841
- IUPAC Standard InChIKey: HYBBIBNJHNGZAN-UHFFFAOYSA-N
- CAS Registry Number: 98-01-1
- 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:
- Other names: 2-Furancarboxaldehyde; 2-Furaldehyde; α-Furole; Artificial ant oil; Fural; Furaldehyde; Furale; Furancarbonal; Furfuraldehyde; Furfurole; Furfurylaldehyde; Furole; Pyromucic aldehyde; 2-Formylfuran; 2-Furanaldehyde; 2-Furancarbonal; 2-Furfural; 2-Furfuraldehyde; 2-Furylaldehyde; Furol; 2-Furylmethanal; Artificial oil of ants; Furfurale; Furfurol; NCI-C56177; 2-Furil-metanale; 2-Furankarbaldehyd; Rcra waste number U125; 2-Furylcarboxaldehyde; Qo furfural; Furan-2-aldehyde; Furan-2-carbaldehyde; NSC 8841; 2-furancarboxyaldehyde; furfural (2-furancarboxaldehyde); 2-Furancarboxaldehyde (furfural); furancarboxaldehyde (furfural)
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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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -35.76 | kcal/mol | N/A | Avramescu and Isagescu, 1978 | Value computed using ΔfHliquid° value of -200.2 kj/mol from Avramescu and Isagescu, 1978 and ΔvapH° value of 50.63±0.42 kj/mol from missing citation.; DRB |
ΔfH°gas | -36.100 | kcal/mol | Cm | Kudchadker and Kudchadker, 1975 | ALS |
ΔfH°gas | -34.49 | kcal/mol | N/A | Miller, 1936 | Value computed using ΔfHliquid° value of -194.9 kj/mol from Miller, 1936 and ΔvapH° value of 50.63±0.42 kj/mol from missing citation.; DRB |
ΔfH°gas | -36.19 | kcal/mol | N/A | Landrieu, Baylocq, et al., 1929 | Value computed using ΔfHliquid° value of -202 kj/mol from Landrieu, Baylocq, et al., 1929 and ΔvapH° value of 50.63±0.42 kj/mol from missing citation.; DRB |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.22 | 100. | Kudchadker S.A., 1975 | GT |
13.60 | 150. | ||
16.58 | 200. | ||
21.67 | 273.15 | ||
23.44 | 298.15 | ||
23.57 | 300. | ||
30.100 | 400. | ||
35.399 | 500. | ||
39.555 | 600. | ||
42.818 | 700. | ||
45.416 | 800. | ||
47.512 | 900. | ||
49.228 | 1000. | ||
50.648 | 1100. | ||
51.833 | 1200. | ||
52.830 | 1300. | ||
53.676 | 1400. | ||
54.398 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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 | -47.85 | kcal/mol | Ccb | Avramescu and Isagescu, 1978 | ALS |
ΔfH°liquid | -46.58 | kcal/mol | Ccb | Miller, 1936 | %hf calculated possible error by author; ALS |
ΔfH°liquid | -48.2 | kcal/mol | Ccb | Landrieu, Baylocq, et al., 1929 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -559.04 ± 0.02 | kcal/mol | Ccb | Avramescu and Isagescu, 1978 | Corresponding ΔfHºliquid = -47.85 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -560.3 | kcal/mol | Ccb | Miller, 1936 | %hf calculated possible error by author; Corresponding ΔfHºliquid = -46.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -558.7 | kcal/mol | Ccb | Landrieu, Baylocq, et al., 1929 | Corresponding ΔfHºliquid = -48.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 52.10 | cal/mol*K | N/A | Miller, 1935 | Extrapolation below 90 K, 52.38 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.12 | 293. | Rastorguev and Ganiev, 1967 | T = 293 to 373 K.; DH |
38.91 | 298.15 | Omel'chenko, 1962 | T = 288 to 412 K.; DH |
37.81 | 298. | von Reis, 1881 | T = 290 to 347 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
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 434.7 ± 0.4 | K | AVG | N/A | Average of 11 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 234.5 | K | N/A | Timmermans, 1922 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 235.1 | K | N/A | Miller, 1936, 2 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 670. | K | N/A | N/A | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 54.38 | atm | N/A | N/A | Uncertainty assigned by TRC = 0.9678 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12.1 ± 0.05 | kcal/mol | GS | Emel'yanenko, Dabrowska, et al., 2007 | Based on data from 277. to 323. K.; AC |
ΔvapH° | 12.1 ± 0.05 | kcal/mol | EB | Hauschild, Wu, et al., 1987 | Based on data from 366. to 394. K. See also Emel'yanenko, Dabrowska, et al., 2007.; AC |
ΔvapH° | 12.10 ± 0.10 | kcal/mol | V | Mathews, 1926 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 10.33 ± 0.21 kcal/mol; ALS |
ΔvapH° | 12.1 ± 0.1 | kcal/mol | EB | Mathews, 1926 | Based on data from 329. to 434. K. See also Emel'yanenko, Dabrowska, et al., 2007.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
363.2 | 0.086 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.7 | 372. | A | Stephenson and Malanowski, 1987 | Based on data from 357. to 435. K.; AC |
11.5 | 344. | N/A | Matthews, Sumner, et al., 1950 | Based on data from 329. to 433. K. See also Boublik, Fried, et al., 1984.; AC |
11.4 | 380. | N/A | Evans and Aylesworth, 1926 | Based on data from 365. to 443. K. See also Boublik, Fried, et al., 1984.; AC |
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 |
---|---|---|---|---|---|
329.02 to 433.90 | 4.08784 | 1430.133 | -84.449 | Matthews, Sumner, et al., 1950, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.435 | 235.1 | Domalski and Hearing, 1996 | AC |
3.4340 | 235.1 | Miller, 1935 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
14.6 | 235.1 | Miller, 1935 | DH |
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
By formula: C11H10N2O + H2O = C6H8N2 + C5H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -14.8 | kcal/mol | Cm | Landrieu, 1905 | solid phase |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
- LIQUID (NEAT); PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 4000-1330 CM-1, 10% IN CS2 FOR 1330-600 CM-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- VAPOR (5 MICROLITER AT 150 C); PERKIN-ELMER 180; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2-3 CM-1 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118785 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Avramescu and Isagescu, 1978
Avramescu, F.; Isagescu, D.A.,
Heats of combustion of mono- and difurfurylidene acetone,
Rev. Roum. Chim., 1978, 23, 655-659. [all data]
Kudchadker and Kudchadker, 1975
Kudchadker, S.A.; Kudchadker, A.P.,
Thermodynamic properties of oxygen compounds. III. Benzaldehyde and furfural (2-furaldehyde),
Ber. Bunsenges. Phys. Chem., 1975, 12, 432-437. [all data]
Miller, 1936
Miller, P.,
The free energy of furfural and some of its derivatives,
Iowa State Coll. J. Sci., 1936, 10, 91-93. [all data]
Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R.,
Etude thermochimique dans la serie furanique,
Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]
Kudchadker S.A., 1975
Kudchadker S.A.,
Thermodynamic properties of oxygen compounds. III. Benzaldehyde and furfural (2-furaldehyde),
Thermochim. Acta, 1975, 12, 432-437. [all data]
Miller, 1935
Miller, P.,
The free energy of furfural and some of its derivatives,
Iowa State Coll. J. Sci., 1935, 10, 91-93. [all data]
Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A.,
Study of the heat capacity of selected solvents,
Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]
Omel'chenko, 1962
Omel'chenko, F.S.,
Specific heat of furfural,
Izv. Vyssh. Ucheb. Zaved. Pishch. Tekhnol., 1962, No. 2, 151-152. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [all data]
Timmermans, 1922
Timmermans, J.,
Investigation of the Freezing Point of Organic Substances VII,
Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]
Miller, 1936, 2
Miller, P.,
The Free Energy of Furfural and Some of Its Derivatives,
Iowa State Coll. J. Sci., 1936, 10, 91-3. [all data]
Emel'yanenko, Dabrowska, et al., 2007
Emel'yanenko, Vladimir N.; Dabrowska, Aldona; Hertel, Marcus O.; Scheuren, Hans; Sommer, Karl,
Vapor Pressures, Enthalpies of Vaporization, and Limiting Activity Coefficients in Water at 100 °C of 2-Furanaldehyde, Benzaldehyde, Phenylethanal, and 2-Phenylethanol,
J. Chem. Eng. Data, 2007, 52, 2, 468-471, https://doi.org/10.1021/je060406c
. [all data]
Hauschild, Wu, et al., 1987
Hauschild, Torsten; Wu, Huey S.; Sandler, Stanley I.,
Vapor-liquid equilibrium of the mixtures 2-furaldehyde/1-butanol and 2-furaldehyde/4-methyl-2-pentanone,
J. Chem. Eng. Data, 1987, 32, 2, 226-229, https://doi.org/10.1021/je00048a028
. [all data]
Mathews, 1926
Mathews, J.H.,
The accurate measurement of heats of vaporization of liquids,
J. Am. Chem. Soc., 1926, 48, 562-576. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [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]
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]
Matthews, Sumner, et al., 1950
Matthews, J.B.; Sumner, J.F.; Moelwyn-Hughes, E.A.,
The vapour pressures of certain liquids,
Trans. Faraday Soc., 1950, 46, 797, https://doi.org/10.1039/tf9504600797
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Evans and Aylesworth, 1926
Evans, W.V.; Aylesworth, M.B.,
Some critical constants of furfural,
Ind. Eng. Chem., 1926, 18, 1, 24-27, https://doi.org/10.1021/ie50193a013
. [all data]
Matthews, Sumner, et al., 1950, 2
Matthews, J.B.; Sumner, J.F.; Moelwyn-Hughes, E.A.,
The Vapour Pressures of Certain Liquids,
Trans. Faraday Soc., 1950, 46, 797-803, https://doi.org/10.1039/tf9504600797
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Landrieu, 1905
Landrieu, M.Ph.,
Thermochimie. - Thermochimie des hydrazones,
Compt. Rend., 1905, 141, 358-361. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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