Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is a colorless waxy solid which melts at 58 °C.
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| Names | |||
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| Preferred IUPAC name
Butanedinitrile[1] | |||
Other names
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| Identifiers | |||
3D model (JSmol)
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| 1098380 | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.441 | ||
| EC Number |
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| MeSH | succinonitrile | ||
PubChem CID
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| RTECS number |
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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)
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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)
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450 mg kg−1 (oral, rat) | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[2] | ||
REL (Recommended)
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TWA 6 ppm (20 mg/m3)[2] | ||
IDLH (Immediate danger)
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N.D.[2] | ||
| Related compounds | |||
Related alkanenitriles
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Related compounds
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DBNPA | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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).
See also
edit- 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
edit- ^ 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
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