Aniline: Difference between revisions
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(Created page with "{{Compound|name=Aniline|struct=Aniline.png|chemf=C6H5NH2|mm=93.13|density=1.0217|mp=-6.3|bp=184.13|idlh=5ppm (inh)|nfpa_h=3|nfpa_f=2|stp_p=liquid|stp_q=clear or yellowish}} ==Uses== {{Justify}} ===Other=== * Feedstock for synthetic indigo dye (indigotin) * Precursor for many organic compounds, including sulfa drugs via N-acetylsulfanilyl chloride ==Natural occurrence== ==Hazards== * Toxic and flammable ** Inhalation, ingestion, or skin exposure can all result in...") |
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{{Compound|name=Aniline | {{Compound|name=Aniline|chemf=C6H5NH2|mm=93.13|density=1.0217|mp=-6.3|bp=184.13|idlh=5ppm (inh)|nfpa_h=3|nfpa_f=2|stp_p=liquid|stp_q=clear or yellowish}} | ||
==Uses== | ==Uses== | ||
{{Justify}} | {{Justify}} | ||
Latest revision as of 00:36, 18 December 2024
| Chemical formula | C6H5NH2 |
|---|---|
| OTP appearance | clear or yellowish liquid |
| Molar Mass(g/mol) | 93.13 |
| Density(g/cc) | 1.0217 |
| Melting Point(°C) | -6.3 |
| Boiling Point(°C) | 184.13 |
| Immediate Danger to Life and Health | 5ppm (inh) |
| NFPA 704 |  2
3
0
|
Uses
Justification Questioned
Other
- Feedstock for synthetic indigo dye (indigotin)
- Precursor for many organic compounds, including sulfa drugs via N-acetylsulfanilyl chloride
Natural occurrence
Hazards
- Toxic and flammable
- Inhalation, ingestion, or skin exposure can all result in aniline toxicity, which can produce cyanosis and cardiopulmonary difficulties leading to hypoxia. Treatments include supplementary oxygen, breathing support, and methylene blue. The standard dose of methylene blue is 1 to 2 mg/kg body weight (0.1 to 0.2 mL/kg of a 1% solution) intravenously over 5 to 10 minutes, repeated in one hour if needed. The total 24 hour dose should not exceed 7 mg/kg
Production
Extraction
from indigotin
Aniline, [...] an oily liquid which distils over when finely pulverized indigo is decomposed by a highly concentrated solution of caustic potash or soda in a retort Its quantity amounts to about 15 or 20 per cent of the indigo employed.[1]
The quote above indicates that dry distillation converts about two molecules of indigotin to one of aniline: 93 / (2 × 262) = 17.7. Either that or the indigotin contained a significant percent by weight of impurities.
- Combine indigotin and one of sodium, potassium, or calcium hydroxide.
- Mix thoroughly
- Grind finely
- Distill
- Discard residue
- Distillate is aniline (yield: 3g per kg of plant?)
Synthesis
- From nitrobenzene via reduction with hydrogen and a catalyst (Zinin)
See Also
References
- ↑ Graham, Thomas (1843) "Elements of Chemistry: Including the Applications of the Science in the Arts"; pp623.