Succinonitrile
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Butanedinitrile[1] | |||
Other names
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| Identifiers | |||
3D model (JSmol) | |||
| 1098380 | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.441 | ||
| EC Number |
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| MeSH | succinonitrile | ||
PubChem CID | |||
| RTECS number |
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| UNII | |||
CompTox Dashboard (EPA) | |||
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| Properties | |||
| C4H4N2 | |||
| Molar mass | 80.090 g·mol−1 | ||
| Appearance | Colorless, waxy crystals | ||
| Odor | odorless[2] | ||
| Density | 985 mg mL−1 | ||
| Melting point | 58 °C (136 °F; 331 K)[3] | ||
| Boiling point | 266.1 °C; 510.9 °F; 539.2 K | ||
| 130 g L−1 | |||
| Vapor pressure | 300 Pa (at 100 °C) | ||
| Thermochemistry | |||
Heat capacity (C) | 145.60 J K−1 mol−1 | ||
Std molar entropy (S⦵298) | 191.59 J K−1 mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) | 139.3–140.4 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) | −2.2848–−2.2860 MJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
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| Warning | |||
| H302, H315, H319, H335 | |||
| P261, P305+P351+P338 | |||
| Flash point | 113 °C (235 °F; 386 K) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 450 mg kg−1 (oral, rat) | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | none[2] | ||
REL (Recommended) | TWA 6 ppm (20 mg/m3)[2] | ||
IDLH (Immediate danger) | N.D.[2] | ||
| Related compounds | |||
Related alkanenitriles | |||
Related compounds | DBNPA | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references | |||
Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is a colorless waxy solid which melts at 58 °C.
Succinonitrile is produced by the addition of hydrogen cyanide to acrylonitrile (hydrocyanation):[4]
- CH2=CHCN + HCN → NCCH2CH2CN
Hydrogenation of succinonitrile yields putrescine (1,4-diaminobutane).
Applications
Succinonitrile may find applications as the "solvent" (while still in its waxy state) in lithium batteries.
See also
- Malononitrile - A di-nitrile with 3 carbon atoms
- Glutaronitrile - A di-nitrile with 5 carbon atoms
- Adiponitrile - A di-nitrile with 6 carbon atoms
References
- ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 902. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0573". National Institute for Occupational Safety and Health (NIOSH).
- ^ Rubinstein, E. R.; Tirmizi, S. H.; Glicksman, M. E. (1990-11-01). "Long-term purity assessment in succinonitrile". Journal of Crystal Growth. 106 (1): 89–96. Bibcode:1990JCrGr.106...89R. doi:10.1016/0022-0248(90)90290-2. ISSN 0022-0248.
- ^ "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (7th ed.). Retrieved 2007-09-10.
External links