My watch list
my.chemeurope.com  
Login  

Pentachlorophenol



Pentachlorophenol
IUPAC name 2,3,4,5,6-Pentachlorophenol
Identifiers
CAS number 87-86-5
PubChem 992
SMILES Clc1c(Cl)c(Cl)c(Cl)c(Cl)c1O
Properties
Molecular formula C6HCl5O
Molar mass 266.34 g mol-1
Appearance White crystalline solid
Density 1.978 g/cm3 at 22 °C
Melting point

190-191 °C

Boiling point

309-310 °C (dec.)

Solubility in water 0.020 g/L at 30 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Pentachlorophenol (PCP) is a synthetic substance that was first produced in the 1930s. It is marketed under the trade names, Santophen, Pentachlorol, Chlorophen, Chlon, Dowicide 7, Pentacon, Penwar, Sinituho and Penta among others. It can be found in two forms: PCP itself or as the sodium salt of PCP, which dissolves easily in water. In the past, it has been used as a herbicide, insecticide, fungicide, algaecide, disinfectant and as an ingredient in antifouling paint. Some applications were in agricultural seeds (for nonfood uses), leather, masonry, wood, cooling tower water, rope and paper mill system.

Since the early 1980s, the purchase and use of PCP in the U.S has not been available to the general public. Nowadays most of the PCP used in the U.S is restricted to the treatment of utility poles and railroads ties.

There are two general methods for preserving wood. The pressure process method involves placing wood in a pressure-treating vessel where it is immersed in PCP and then subjected to applied pressure. In the non-pressure process method, PCP is applied by spraying, brushing, dipping, and soaking. Utility companies save millions of dollars in replacement poles, because the life of these poles increases from approximately 7 years for an untreated pole to about 35 years for a preservative-treated pole.

Additional recommended knowledge

Contents

Synthesis

PCP can be produced by the chlorination of phenol in the presence of catalyst (anhydrous aluminium or ferric chloride) and a temperature of up to approximately 191 °C. However this process is incomplete. As a result, commercial grade PCP is between 84% and 90% pure. During the process several contaminants including other polychlorinated phenols, polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans are produced too, which can be more toxic than the PCP itself.

Exposure

People may be exposed to PCP in occupational settings through the inhalation of contaminated workplace air and dermal contact or with wood products treated with the chemical. Also, general population exposure may occur through contact with contaminated environment media, particularly in the vicinity of wood treatment facilities and hazardous wastes sites. In addition, some other important routes of exposure seem to be the inhalation of contaminated air, ingestion of contaminated ground water used as a source of drinking water, ingestion of contaminated food, and dermal contact with soils or products treated with the chemical.

Toxicity

Short-term exposure to large amounts of PCP can cause harmful effects on the liver, kidneys, blood, lungs, nervous system, immune system, and gastrointestinal tract. Further, elevated temperature, profuse sweating, uncoordinated movement, muscle twitching, and coma are additional side effects.

Contact with PCP (particularly in the form of vapor) can irritate the skin, eyes, and mouth. Long-term exposure to low levels such as those that occur in the workplace can cause damage to the liver, kidneys, blood, and nervous system. Finally exposure to PCP is also associated with carcinogenic, renal, and neurological effects. The EPA classifies PCP in group B2 (probable human carcinogen).

Fate in humans and animals

PCP is quickly absorbed through the gastrointestinal tract following ingestion. Accumulation is not common, but if it does occur, the major sites are the liver, kidneys, plasma protein, spleen and fat. Unless kidney and liver functions are impaired, PCP is quickly eliminated from tissues and blood, and is excreted, mainly unchanged or in conjugated form via the urine. Single doses of PCP have half-lives in blood of 30 to 50 hours in humans. Biomagnification of PCP in the food chain is not thought to be significant due to the fairly rapid metabolism of the compound by exposed organisms.

Releases to the environment

PCP has been detected in surface waters and sediments, rainwater, drinking water, aquatic organisms, soil, and food, as well as in human milk, adipose tissue, and urine.

Currently, releases to the environment are more limited as a result of decreasing volumes used and changing use methods. However PCP is still released, to surface waters from the atmosphere by wet deposition, from soil by run off and leaching, manufacturing and processes facilities. Also, PCP is released directly into the atmosphere via volatilization from treated woods products and during production. Finally, releases to the soil can be by leaching from treated wood products, atmospheric deposition in precipitation (such as rain and snow), spills at industrial facilities and at hazardous waste sites.

Environmental fate

After PCP is released into the atmosphere it is transformed via photolysis. The main biodegradative pathway for PCP is reductive dehalogenation. In this process, the compound PCP is broken down to tetra-, tri-, and dichlorophenols. Another pathway is methylation to pentaclhloroanisole (a more lipid soluble compound). These two methods eventually lead to ring cleavage and complete degradation.

In shallow waters, PCP is also quickly removed by photolysis. In deep or turbid water processes such as sorption and biodegradation take place. In soil and sediments, PCP is degraded within 14 days to 5 years depending on the soil bacteria present. However, adsorption of PCP in soils is pH dependent because it increases under acidic conditions and it decreases in neutral and basic conditions.

References

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Pentachlorophenol". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE