Succinonitrile
Chemical compound
From Wikipedia, the free encyclopedia
Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is an odorless, colorless to light brown crystal or colourless waxy solid which melts at 58 °C.[4][5]
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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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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| C4H4N2 | |||
| Molar mass | 80.090 g·molâ1 | ||
| Appearance | Colorless, waxy crystals | ||
| Odor | odorless[2] | ||
| Density | 985 mg mLâ1 | ||
| Melting point | 58 °C (136 °F; 331 K)[3] | ||
| Boiling point | 266.1 °C; 510.9 °F; 539.2 K | ||
| 130 g Lâ1 | |||
| Vapor pressure | 300 Pa (at 100 °C) | ||
| Thermochemistry | |||
Heat capacity (C) |
145.60 J Kâ1 molâ1 | ||
Std molar entropy (S⦵298) |
191.59 J Kâ1 molâ1 | ||
Std enthalpy of formation (ÎfH⦵298) |
139.3â140.4 kJ molâ1 | ||
Std enthalpy of combustion (ÎcH⦵298) |
â2.2848ââ2.2860 MJ molâ1 | ||
| 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 kgâ1 (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 |
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Related compounds |
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):[6]
- CH2=CHCN + HCN â 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.[citation needed]
Safety
Like most nitriles, succinonitrile is toxic and can release cyanide ions in the body. NIOSH recommends a TWA exposure limit of 6 ppm (20 mg/m³).[4]
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
