1,4-Dichlorobenzene

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1,4-Dichlorobenzene
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Template:Longitem 49722
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UN number 3077
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance Colorless/white crystals[1]
Odor mothball-like[1]
Density 1.25 g/cm3, solid
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Vapor pressure 1.3 mmHg (20 °C)[1]
Template:Longitem −82.93·10−6 cm3/mol
Template:Longitem 1,2-Dichlorobenzene
1,3-Dichlorobenzene

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1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.

It is used as a disinfectant, pesticide, and deodorant, most familiarly in mothballs in which it is a replacement for the more traditional naphthalene because of naphthalene's greater flammability (though both chemicals have the same NFPA 704 rating). It is also used as a precursor in the production of the chemically and thermally resistant polymer poly(p-phenylene sulfide).[2]

Production

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. The compound 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.[2]

Uses

Disinfectant, deodorant, and pesticide

File:1,4 dichlorobenzene balls.jpg
1,4-dichlorobenzene balls sold as urinal disinfectant

p-DCB is used to control moths, molds, and mildew.[3] It also finds use as a disinfectant[2] in waste containers and restrooms and is the characteristic smell associated with urinal cakes. Its usefulness for these applications arises from p-DCB's low solubility in water and its relatively high volatility: it sublimes readily near room temperature.[2]

Precursor to other chemicals

Nitration gives 1,4-dichloronitrobenzene, a precursor to commercial dyes and pigments.[4] The chloride sites on p-DCB can be substituted with hydroxylamine and sulfide groups. In a growing application, p-DCB is the precursor to the high performance polymer poly(p-phenylene sulfide):[5]

Synthesis of polyphenylensulfide

As ceruminolytic agent

2% Paradichlorobenzene used as a ceruminolytic agent for the treatment of impacted earwax.[6]

Environmental and health effects

p-DCB is poorly soluble in water and is not easily broken down by soil organisms. Like many hydrocarbons, p-DCB is lipophilic and will accumulate in fatty tissues if consumed by a person or animal.

The United States Department of Health and Human Services (DHHS) and the International Agency for Research on Cancer (IARC) have determined that p-DCB may reasonably be anticipated to be a carcinogen.[7] This has been indicated by animal studies, although a full-scale human study has not been done.[8]

The United States Environmental Protection Agency (EPA) has set a target maximum contaminant level of 75 micrograms of p-DCB per liter of drinking water (75 μg/L),[9] but publishes no information on the cancer risk.[10] p-DCB is also an EPA-registered pesticide.[11] The United States Occupational Safety and Health Administration (OSHA) has set a maximum level of 75 parts of p-DCB per million parts air in the workplace (75 ppm) for an 8-hour day, 40-hour workweek.[12][13]

A mechanism for the carcinogenic effects of mothballs and some types of air fresheners containing p-DCB has been identified in roundworms.[14]

Due to its carcinogenic nature, use of paradichlorobenzene in the European Union is forbidden as an air freshener (since 2005) and in mothballs (since 2008).

Biodegradation

Rhodococcus phenolicus is a bacterium species able to degrade dichlorobenzene as its sole carbon source.[15]

See also

References

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  5. ↑ Script error: No such module "Citation/CS1".
  6. ↑ Script error: No such module "Citation/CS1".
  7. ↑ Preamble to the IARC Monographs Template:Webarchive definition of "Group 2B: Possibly carcinogenic to humans", the International Agency for Research on Cancer classification of this chemical
  8. ↑ Script error: No such module "citation/CS1".
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External links

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