1,4-Dichlorobenzene
| Names | |
|---|---|
| IUPAC name
1,4-Dichlorobenzene
| |
| Other names
para-Dichlorobenzene
p-Dichlorobenzene p-DCB PDB PDCB Paramoth Para crystals Paracide Dichlorocide | |
| Properties | |
| C6H4Cl2 | |
| Molar mass | 147.00 g/mol |
| Appearance | White solid |
| Odor | Mothball-like |
| Density | 1.2475 g/cm3 (20 °C) |
| Melting point | 53.5 °C (128.3 °F; 326.6 K) |
| Boiling point | 174 °C (345 °F; 447 K) |
| 0.0105 g/100 ml (20 °C) | |
| Solubility | Soluble in acetone, benzene, chloroform, carbon disulfide, diethyl ether, ethanol |
| Vapor pressure | 1.3 mmHg (20 °C) |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 66 °C |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
500 mg/kg (oral, rat) 2950 mg/kg (oral, mouse) 2512 mg/kg (oral, rat) 2830 mg/kg (oral, rabbit) |
| Related compounds | |
| Related compounds
|
Benzene Chlorobenzene |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
1,4-Dichlorobenzene or p-dichlorobenzene, p-DCB is an organic compound with the formula C6H4Cl2.
Contents
Properties
Chemical
Nitration of p-DCB gives 1,4-dichloronitrobenzene, a precursor to many commercial dyes and pigments.
At standard conditions, p-dichlorobenzene does not react with strong alkaline bases, such as sodium hydroxide.
Physical
1,4-Dichlorobenzene is a white solid, with a strong odor, insoluble in water.
Availability
1,4-Dichlorobenzene is available as naphthalene-free moth balls. Neither compounds can be used safely as moth repellent when mixed, meaning p-DCB mothballs should be relative pure, though purification via recrystallization or sublimation may still be required if a purer product is desired.
Higher purity p-DCB can be bought from chemical suppliers.
Preparation
p-DCB is produced by chlorination of benzene using ferric chloride as a catalyst:
- C6H6 + 2 Cl2 → C6H4Cl2 + 2 HCl
The chief impurity is the 1,2 isomer, which can be purified by fractional crystallization, taking advantage of its relatively high melting point of 53.5 °C; the isomeric dichlorobenzenes and chlorobenzene melt well below room temperature.
Projects
- Make hydroquinone
- Make 1,4-dichloro-2-nitrobenzene
Handling
Safety
1,4-Dichlorobenzene is irritant and a suspected carcinogen. It is also classified as neurotoxin. Like many hydrocarbons, p-DCB is lipophilic and will accumulate in the fatty tissues.
Storage
Due to its strong smell and volatility, it's best to keep p-DCB is air-tight containers. Zipper bags are a good choice, but if you want better storage, an all-metal can with a lid, similar to those used for instant coffee or paint are better. If you worry about corrosion, check the interior of the can for any corrosion and then coat it in a protective polymer.
Disposal
The disposal of halogenated aromatic compounds is difficult, as these compounds are known to resist degradation, meaning you cannot simply just dump them down the drain.
If you really want to do a proper neutralization, you can slowly add the compound in an oxidizing solution, such as chromic acid, piranha solution or Fenton's reagent. Do this outside and make sure you don't add too much to limit splashing and aerosolization of p-DCB. Do not do this unless you know what you're doing.
