Difference between revisions of "Aniline"
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| PIN = | | PIN = | ||
| SystematicName = | | SystematicName = | ||
| − | | OtherNames = Aminobenzene<br>Benzenamine<br>Benzamine<br>Phenylamine | + | | OtherNames = Aminobenzene<br>Aminophen<br>Benzenamine<br>Benzamine<br>Phenylamine |
<!-- Images --> | <!-- Images --> | ||
| ImageFile = | | ImageFile = | ||
| Line 55: | Line 55: | ||
| Formula = C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> | | Formula = C<sub>6</sub>H<sub>5</sub>NH<sub>2</sub> | ||
| HenryConstant = | | HenryConstant = | ||
| − | | LogP = | + | | LogP = 0.9 |
| MolarMass = 93.13 g/mol | | MolarMass = 93.13 g/mol | ||
| MeltingPt = | | MeltingPt = | ||
| Line 61: | Line 61: | ||
| MeltingPt_ref = | | MeltingPt_ref = | ||
| MeltingPt_notes = | | MeltingPt_notes = | ||
| − | | pKa = | + | | Odor = Aromatic aminic |
| − | | pKb = 9. | + | | pKa = 4.6 (for the conjugate acid) |
| − | | Solubility = | + | | pKb = 9.4 |
| − | | SolubleOther = | + | | Solubility = 3.6 g/100 ml (20 °C) |
| + | | SolubleOther = Miscible with [[acetone]], [[benzene]], [[chloroform]], [[diethyl ether]], [[ethanol]], oils | ||
| Solvent = | | Solvent = | ||
| VaporPressure = 0.6 mmHg (20 °C) | | VaporPressure = 0.6 mmHg (20 °C) | ||
| Line 75: | Line 76: | ||
| Section4 = {{Chembox Thermochemistry | | Section4 = {{Chembox Thermochemistry | ||
| DeltaGf = | | DeltaGf = | ||
| − | | DeltaHc = | + | | DeltaHc = -3394 kJ/mol |
| DeltaHf = | | DeltaHf = | ||
| Entropy = | | Entropy = | ||
| Line 87: | Line 88: | ||
}} | }} | ||
| Section6 = {{Chembox Hazards | | Section6 = {{Chembox Hazards | ||
| − | | AutoignitionPt = | + | | AutoignitionPt = 770 °C (1,420 °F; 1,040 K) |
| − | | ExploLimits = | + | | ExploLimits = 1.3%-11% |
| − | | ExternalMSDS = | + | | ExternalMSDS = [https://www.docdroid.net/QDZJt78/aniline-sa.pdf.html Sigma-Aldrich] |
| − | | FlashPt = | + | | FlashPt = 70 °C (158 °F; 343 K) |
| LD50 = | | LD50 = | ||
| − | | LC50 = | + | | LC50 = 175 ppm (mouse, 7 hr) |
| − | | MainHazards = | + | | MainHazards = Irritant |
| NFPA-F = | | NFPA-F = | ||
| NFPA-H = | | NFPA-H = | ||
| Line 104: | Line 105: | ||
| OtherFunction = | | OtherFunction = | ||
| OtherFunction_label = | | OtherFunction_label = | ||
| − | | OtherCompounds = | + | | OtherCompounds = [[Nitrobenzene]]<br>[[Benzylamine]] |
}} | }} | ||
}} | }} | ||
| Line 111: | Line 112: | ||
==Properties== | ==Properties== | ||
===Chemical=== | ===Chemical=== | ||
| − | Aniline can be oxidized with potassium permanganate to nitrobenzene. This reaction is the opposite of aniline's synthesis. | + | Aniline can be oxidized with potassium permanganate to [[nitrobenzene]]. This reaction is the opposite of aniline's synthesis. |
===Physical=== | ===Physical=== | ||
| Line 117: | Line 118: | ||
==Availability== | ==Availability== | ||
| − | Aniline is sold by various chemical suppliers. | + | Aniline is sold by various chemical suppliers, though it's not easy to obtain. |
==Preparation== | ==Preparation== | ||
| Line 132: | Line 133: | ||
===Storage=== | ===Storage=== | ||
| − | Aniline should be stored in closed bottles, away from any source of ignition and copper alloys. Due to its foul smell, it's best to keep it in a separate cabinet. | + | Aniline should be stored in closed bottles, best in amber glass bottler with a PTFE lining, away from any source of ignition and copper alloys. Due to its foul smell, it's best to keep it in a separate cabinet. Aniline will darken after a period of time, due to oxidation from air. To limit this, you can either make the bottle air-tight, store it under inert gas or add a compatible reducing agent, to scavenge the dissolved oxygen. |
| + | |||
| + | When using the aniline for reactions, it's best to purify it first, and this can be done by distilling it under vacuum. | ||
===Disposal=== | ===Disposal=== | ||
Due to aniline's high flash point (70 °C), burning it in not a (good) option, as heating it to achieve the flash point will release lots of unpleasant and highly toxic aniline vapors. You can however, dilute it in a more flammable solvent and burn it in this form. Since some aniline will escape, it's mandatory to do this '''outside'''. | Due to aniline's high flash point (70 °C), burning it in not a (good) option, as heating it to achieve the flash point will release lots of unpleasant and highly toxic aniline vapors. You can however, dilute it in a more flammable solvent and burn it in this form. Since some aniline will escape, it's mandatory to do this '''outside'''. | ||
| − | Aniline can be destroyed by adding it dropwise in a fresh solution of Fenton's reagent. Since the oxidation will aerosolize a small amount of aniline, this is best done outside. | + | Aniline can be destroyed by adding it dropwise in a fresh solution of Fenton's reagent. Since the oxidation will aerosolize a small amount of aniline, this is best done outside. As aniline has a strong and unpleasant smell, '''do not do this indoors'''! |
| + | |||
| + | Adding water or an acid to aniline will generate a white mist, consisting of a very fine aniline salt, resulted from the reaction of aniline and acid vapors. This will (very slowly) settle on in the room, on various objects, clothes, furniture and will release aniline in contact with a stronger base. | ||
==References== | ==References== | ||
| Line 149: | Line 154: | ||
[[Category:Amines]] | [[Category:Amines]] | ||
[[Category:Bases]] | [[Category:Bases]] | ||
| + | [[Category:Organic bases]] | ||
[[Category:Lewis bases]] | [[Category:Lewis bases]] | ||
[[Category:Materials unstable in acidic solution]] | [[Category:Materials unstable in acidic solution]] | ||
| Line 154: | Line 160: | ||
[[Category:Foul smelling compounds]] | [[Category:Foul smelling compounds]] | ||
[[Category:Liquids]] | [[Category:Liquids]] | ||
| + | [[Category:Irritants]] | ||
| + | [[Category:Air-sensitive materials]] | ||
Latest revision as of 14:54, 12 July 2020
| Names | |
|---|---|
| IUPAC name
Phenylamine
| |
| Other names
Aminobenzene
Aminophen Benzenamine Benzamine Phenylamine | |
| Identifiers | |
| Jmol-3D images | Image |
| |
| Properties | |
| C6H5NH2 | |
| Molar mass | 93.13 g/mol |
| Appearance | Colorless to yellow liquid |
| Odor | Aromatic aminic |
| Density | 1.0217 (at 20 °C) |
| Melting point | −6.3 °C (20.7 °F; 266.8 K) |
| Boiling point | 184.13 °C (363.43 °F; 457.28 K) |
| 3.6 g/100 ml (20 °C) | |
| Solubility | Miscible with acetone, benzene, chloroform, diethyl ether, ethanol, oils |
| Vapor pressure | 0.6 mmHg (20 °C) |
| Acidity (pKa) | 4.6 (for the conjugate acid) |
| Thermochemistry | |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 70 °C (158 °F; 343 K) |
| Lethal dose or concentration (LD, LC): | |
| LC50 (Median concentration)
|
175 ppm (mouse, 7 hr) |
| Related compounds | |
| Related compounds
|
Nitrobenzene Benzylamine |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Aniline, also known as aminobenzene or phenylamine is an aromatic organic compound, the simplest aromatic amine. It has the chemical formula C6H7N or more convenient C6H5NH2.
Contents
Properties
Chemical
Aniline can be oxidized with potassium permanganate to nitrobenzene. This reaction is the opposite of aniline's synthesis.
Physical
Aniline is a colorless liquid with a strong ammonia or fish-like odor. It is miscible with water and most organic solvents.
Availability
Aniline is sold by various chemical suppliers, though it's not easy to obtain.
Preparation
There are several ways to make aniline. The most common way involves the reduction of nitrobenzene with hydrogen in the presence of a metal catalyst.
Another method of obtaining aniline is through the destructive distillation of Indigo.
Projects
- Make trinitroaniline
Handling
Safety
Aniline is toxic in large quantities and it's best to avoid being exposed to it for too long.
Storage
Aniline should be stored in closed bottles, best in amber glass bottler with a PTFE lining, away from any source of ignition and copper alloys. Due to its foul smell, it's best to keep it in a separate cabinet. Aniline will darken after a period of time, due to oxidation from air. To limit this, you can either make the bottle air-tight, store it under inert gas or add a compatible reducing agent, to scavenge the dissolved oxygen.
When using the aniline for reactions, it's best to purify it first, and this can be done by distilling it under vacuum.
Disposal
Due to aniline's high flash point (70 °C), burning it in not a (good) option, as heating it to achieve the flash point will release lots of unpleasant and highly toxic aniline vapors. You can however, dilute it in a more flammable solvent and burn it in this form. Since some aniline will escape, it's mandatory to do this outside.
Aniline can be destroyed by adding it dropwise in a fresh solution of Fenton's reagent. Since the oxidation will aerosolize a small amount of aniline, this is best done outside. As aniline has a strong and unpleasant smell, do not do this indoors!
Adding water or an acid to aniline will generate a white mist, consisting of a very fine aniline salt, resulted from the reaction of aniline and acid vapors. This will (very slowly) settle on in the room, on various objects, clothes, furniture and will release aniline in contact with a stronger base.
References
Relevant Sciencemadness threads
- Chemical pages without CAS Registry Number
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Articles containing unverified chemical infoboxes
- Chembox articles without image
- Chemical compounds
- Organic compounds
- Aromatic compounds
- Amines
- Bases
- Organic bases
- Lewis bases
- Materials unstable in acidic solution
- Volatile chemicals
- Foul smelling compounds
- Liquids
- Irritants
- Air-sensitive materials
