Propanedinitrile
- Formula: C3H2N2
- Molecular weight: 66.0614
- IUPAC Standard InChIKey: CUONGYYJJVDODC-UHFFFAOYSA-N
- CAS Registry Number: 109-77-3
- 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: Malononitrile; Cyanoacetonitrile; Dicyanomethane; Malonic acid dinitrile; Malonodinitrile; Methane, dicyano-; Methylene cyanide; Methylenedinitrile; CH2(CN)2; Malonitrile; Malonic dinitrile; Nitril kyseliny malonove; USAF A-4600; Dwumetylosulfotlenku; Rcra waste number U149; UN 2647; USAF KF-19; NSC 3769
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Phase change data
Go To: Top, Gas Chromatography, 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
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 493.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 491.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 305. | K | N/A | Stephenson, 1994 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 304. | K | N/A | Trunel, 1939 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 307.6 | K | N/A | Van de Vloed, 1939 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 304.65 | K | N/A | Bruhl, 1895 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 304.910 | K | N/A | Girdhar, Westrum, et al., 1968 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.06 K; TRC |
Ttriple | 304.980 | K | N/A | Girdhar, Westrum, et al., 1968 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 304.99 | K | N/A | Westrum and Wulff, 1968 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 18.73 ± 0.23 | kcal/mol | C | Beckhaus, Dogan, et al., 1990 | ALS |
ΔsubH° | 18.7 | kcal/mol | N/A | Beckhaus, Dogan, et al., 1990 | DRB |
ΔsubH° | 18.7 ± 0.24 | kcal/mol | N/A | Beckhaus, Dogan, et al., 1990 | Based on data from 278. to 299. K.; AC |
ΔsubH° | 18.9 ± 0.2 | kcal/mol | V | Boyd, Guha, et al., 1967 | ALS |
ΔsubH° | 19.1 | kcal/mol | N/A | Boyd, Guha, et al., 1967 | DRB |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
382.2 | 0.026 | Weast and Grasselli, 1989 | BS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.56 | 305. | DSC | Badea, Blanco, et al., 2007 | AC |
2.58 | 305. | N/A | Domalski and Hearing, 1996 | AC |
Temperature of phase transition
Ttrs (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|
140. | crystaline, IV, Re | crystaline, II, entrant phase transition; second order | Wasiutynski, Olejarczyk, et al., 1987 | DH |
303. | crystaline, I | crystaline, I' | Wasiutynski, Olejarczyk, et al., 1987 | First order transition.; DH |
260. | crystaline, III | crystaline, II | Wasiutynski, Olejarczyk, et al., 1987 | Phase III is stable below 260 K.; DH |
295. | crystaline, II | crystaline, I | Wasiutynski, Olejarczyk, et al., 1987 | Second order transition.; DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.5801 | 304.99 | crystaline, I | liquid | Girdhar, Westrum, et al., 1968, 2 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
8.458 | 304.99 | crystaline, I | liquid | Girdhar, Westrum, et al., 1968, 2 | DH |
Gas Chromatography
Go To: Top, 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 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 |
---|---|---|---|---|---|
Capillary | SE-33 | 120. | 801. | Juvancz, Cserháti, et al., 1994 | 10. m/0.20 mm/0.15 μm, H2 |
References
Go To: Top, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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, 1994
Stephenson, R.M.,
Mutual Solubility of Water and Nitriles,
J. Chem. Eng. Data, 1994, 39, 225-7. [all data]
Trunel, 1939
Trunel, P.,
Electric Moments in Several Homologous Series of Organic Compounds,
Ann. Chim. (Paris), 1939, 12, 110. [all data]
Van de Vloed, 1939
Van de Vloed, A.,
Bull. Soc. Chim. Belg., 1939, 48, 229. [all data]
Bruhl, 1895
Bruhl, J.W.,
Spectrochemistry of Nitrogen-Containing Compounds. I.,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1895, 16, 193. [all data]
Girdhar, Westrum, et al., 1968
Girdhar, H.L.; Westrum, E.F.; Wulff, C.A.,
Thermodynamic properties and third-law cycle for malononitrile.,
J. Chem. Eng. Data, 1968, 13, 239-42. [all data]
Westrum and Wulff, 1968
Westrum, E.F.; Wulff, C.A.,
Thermodynamic properties and third-law cycle for malononitrile,
J. Chem. Eng. Data, 1968, 13, 239. [all data]
Beckhaus, Dogan, et al., 1990
Beckhaus, H.D.; Dogan, B.; Pakusch, J.; Verevkin, S.; Ruechardt, C.,
Geminal substituent effects. 4. The dependence of the inverse anomeric effect of geminal cyano groups on the structure,
Chem. Ber., 1990, 123, 2153-2159. [all data]
Boyd, Guha, et al., 1967
Boyd, R.H.; Guha, K.R.; Wuthrich, R.,
Thermochemistry of cyanocarbons. II. The heats of combustion of pyridinium dicyanomethylide, malononitrile, and fumaronitrile,
J. Phys. Chem., 1967, 71, 2187-2191. [all data]
Badea, Blanco, et al., 2007
Badea, Elena; Blanco, Ignazio; Della Gatta, Giuseppe,
Fusion and solid-to-solid transitions of a homologous series of alkane-α,ω-dinitriles,
The Journal of Chemical Thermodynamics, 2007, 39, 10, 1392-1398, https://doi.org/10.1016/j.jct.2007.03.005
. [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]
Wasiutynski, Olejarczyk, et al., 1987
Wasiutynski, T.; Olejarczyk, W.; Sciesinski, J.; Witko, W.,
Phase transition studies of malononitrile,
J. Phys. C: Solid State Phys., 1987, 20, L65-L69. [all data]
Girdhar, Westrum, et al., 1968, 2
Girdhar, H.L.; Westrum, E.F., Jr.; Wulff, C.A.,
Thermodynamic properties and third-law cycle for malononitrile,
J. Chem. Eng. Data, 1968, 13, 239-242. [all data]
Juvancz, Cserháti, et al., 1994
Juvancz, Z.; Cserháti, T.; Markides, K.E.; Bradshaw, J.S.; Lee, M.L.,
Characterization of some new polysiloxane stationary phases by principal component analysis,
Chromatographia, 1994, 38, 3/4, 227-231, https://doi.org/10.1007/BF02290341
. [all data]
Notes
Go To: Top, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature Ttrs Temperature of phase transition ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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