87-86-5 Usage
Description
Pentachlorophenol (PCP) is a synthetic, colorless to white crystalline solid that is odorless at room temperature but has a sharp phenolic smell when hot. It is toxic by inhalation, ingestion, and skin absorption, and is used as a fungicide, herbicide, and wood preservative.
Uses
Used in Wood Preservation Industry:
Pentachlorophenol is used as a wood preservative for power line poles, cross arms, fence posts, and other utility structures to protect them from fungal rot and wood-boring insects.
Used in Agricultural Industry:
Pentachlorophenol is used as a pre-harvest defoliant in cotton, a general pre-emergence herbicide, and as a biocide in industrial water systems.
Used in Industrial Applications:
Pentachlorophenol is used as an antimicrobial preservative and fungicide for textiles, leather, paper, and industrial waste systems. It is also used as a surface disinfectant.
Used in Environmental Control:
Pentachlorophenol is used to control termites and wood-boring insects, as well as to protect wood from fungal rot. The sodium salt of pentachlorophenol is used as a general disinfectant.
Production Methods
Pentachlorophenol can be produced by the chlorination of phenol in the presence of AlCl3, or by hydrolysis of hexachlorobenzene with NaOH in methanol.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
Pentachlorophenol may react with strong oxidizing agents. Incompatible with strong bases, acid chlorides and acid anhydrides. Forms salts with alkaline metals. Solutions in oil cause natural rubber to deteriorate, but synthetic rubber may be used in equipment and for protective clothing .
Health Hazard
Dust or vapor irritates skin and mucous membranes, causing coughing and sneezing. Ingestion causes loss of appetite, respiratory difficulties, anesthesia, sweating, coma. Overexposure can cause death.
Health Hazard
Pentachlorophenol is a severe acute toxicant by ingestion and dermal penetration. The compound and its alkali salts can produce local and systemic effects. The symptoms of acute toxicity are headache, dizziness, sweating, nausea, vomiting, dyspnea, chest pain, weakness, fever, collapse, convulsions, and heart failure. Inhalation of its dusts or vapors can cause irritation of the eyes, nose, and throat, and coughing and sneezing. There is no evidence of chronic poisoning or any cumulative effects.LD50 value, oral (mice): 117 mg/kg LD50 value, skin (rats): 96 mg/kg Subacute toxicity studies on rats orally administered pentachlorophenol at a dose of 0.2 mmol/kg/day for 28 days showed no effect on growth. However, this treatment induced cell alterations in liver and changes in relative liver weights (Renner et al. 1987).Fathead minnows exposed to 8–130 g/L of pentachlorophenol for 90 days experienced no adverse effects on their survival, growth, or bone development (Hamilton et al. 1986). Fathead minnows exposed to 8–130 g/L of pentachlorophenol for 90 days experienced no adverse effects on their survival, growth, or bone development (Hamilton et al. 1986). McKim and associates (1986) have conducted aquatic toxicokinetic studies using 14C-labeled pentachlorophenol in rainbow trouts. At sublethal doses and over its 65hour half-life period, about 50% was eliminated over the gills, 30% in the feces and bile, and 20% in the urine. It was found that pentachlorophenol and its metabolites were rapidly eliminated from the bodies of fish .McKim and associates (1986) have conducted aquatic toxicokinetic studies using 14C-labeled pentachlorophenol in rainbow trouts. At sublethal doses and over its 65hour half-life period, about 50% was eliminated over the gills, 30% in the feces and bile, and 20% in the urine. It was found that pentachlorophenol and its metabolites were rapidly eliminated from the bodies of fish.
Fire Hazard
Special Hazards of Combustion Products: Generates toxic and irritating vapors.
Trade name
(The U.S. EPA lists 626 active and canceled/
transferredlabelsforthischemical) CHEM-TOL?; CHLON?;
CHLOROPHEN?; CRYPTOGIL OL?; DOWCIDE? 7;
DOWICIDE? 7; DOW PENTACHLOROPHENOL DP-2
ANTIMICROBIAL?; DURA TREET II?; DUROTOX?;
EP 30?; FORPEN-50?; FUNGIFEN?; GLAZDPENTA
?; GRUNDIER ARBEZOL?; LAUXTOL?;
LIROPREM?; ONTRACK WE HERBICIDE?; ORTHO
TRIOX?; OSMOSE WPC?; PENTACHLOROPHENOL,
DOWICIDE EC-7?; PENTACHLOROPHENOL, DP-
2?; PENTACON?; PENTA-KIL?; PENTA READY?;
PENTASOL?; PENWAR?; PERATOX?; PERMACIDE?;
PERMAGARD?; PERMASAN?; PERMATOX DP-
2?PERMATOX PENTA?; PERMITE?; POL NU?;
PREVENTOL P?; PRILTOX?; SANTOBRITE?;
SANTOPHEN?; SINITUHO?; TERM-I-TROL?;
THOMPSON'S WOOD FIX?; WATERSHED WP?;
WEEDONE?; WOODTREAT A?
Safety Profile
Confirmed human carcinogen with experimental tumorigenic data. Human poison by ingestion. Poison experimentally by ingestion, skin contact, intraperitoneal, and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. A skin irritant. Mutation data reported. Acute poisoning is marked by weakness with changes in respiration, blood pressure, and urinary output. Also causes dermatitis, convulsions, and collapse. Chronic exposure can cause liver and hdney injury. Dangerous; when heated to decomposition it emits highly toxic fumes of Cl-. See also CHLOROPHENOLS
Potential Exposure
Pentachlorophenol (PCP) is a commercially
produced bactericide, fungicide, and slimicide
used primarily for the preservation of wood, wood
products; and other materials. As a chlorinated hydrocarbon,
its biological properties have also resulted in its
use as an herbicide, and molluscicide. Two groups can be expected to encounter the largest exposures. One involves
the small number of employees involved in the manufacture
of PCP. All of these are presently under industrial
health surveillance programs. The second and larger group
are the formulators and wood theaters. Exposure, hygiene
and industrial health practices can be expected to vary from
the small theaters to the larger companies. The principal
use as a wood preservative results in both point source
water contamination at manufacturing and wood preservation
sites and, conceivably, nonpoint source water contamination
through runoff wherever there are PCP-treated
lumber products exposing PCP to soil
Carcinogenicity
The IARC has determined that there is
limited evidence for carcinogenicity in humans
and sufficient evidence of carcinogenicity in
experimental animals.
Environmental Fate
Biological. Under aerobic conditions, microbes in estuarine water partially dechlorinated pentachlorophenol to trichlorophenol (Hwang et al., 1986). The disappearance ofpentachlorophenol was studied in four aquaria with and without mud under aerobic and
anaerobic conditions. Potential biological and/or chemical products identified include
pentachloroanisole, 2,3,4,5-, 2,3,4,6- and 2,3,5,6-tetrachlorophenol (Boyle et al.,Pentachlorophenol degraded in anaerobic sludge to 3,4,5-trichlorophenol which was
further reduced to 3,5-dichlorophenol (Mikesell and Boyd, 1985). In activated sludge, only
0.2% of the applied amount was mineralized to carbon dioxide after 5 days (FreitagPentachlorophenol was statically incubated in the dark at 25°C with yeast extract and
settled domestic wastewater inoculum. Significant biooxidation was observed but with a
gradual adaptation over a 14-day period to achieve complete degradation at 5 mg/L
substrate cultures. At a concentration of 10 mg/L, it took 28 days for pentachlorophenol
to degrade completely (Tabak et al., 1981).Melcer and Bedford (1988) studied the fate of pentachlorophenol in municipal activated
sludge reactor systems that were operated at solids retention times of 10 to 20 days and
hydraulic retention times of 120 days. Under these conditions, pentachloropheno
Metabolic pathway
The insecticidal, antimicrobial and fungicidal properties of pentachlorophenol
were discovered some time ago and the compound was first
used in the 1930s for wood preservation and treatment. This and various
industrial uses and its herbicidal and molluscicidal properties have led to
its widespread use. Many countries have banned the use of pentachlorophenol
as a wood preservative. Its main uses are now in cooling towers,
paper mills and drilling muds (Litchfield and Rao, 1998). The compound
has become distributed in various ecosystems, including those close to
man’s living space. It is volatile and it may be absorbed via ingestion,
inhalation or skin contact.
There exists a very large literature on the toxicology, metabolism, persistence
and environmental effects and fate of pentachlorophenol, with
well over 500 papers published in the last 30 years. Pentachlorophenol is
rapidly and completely decomposed in sunlight; it is biodegraded in soil
and plants and it is metabolised in animals. Pathways include dechlorination,
methylation, oxidation, conjugation with sugars and sulfate and
ring scission. The environmental fate and metabolism of pentachlorophenol
were reviewed in 1986 by Engelhardt et al. (1986) and Renner and
Muecke (1986). The pathways reported below are largely taken from these
papers which are supported by more than 120 references. Other selected
papers which cover important aspects are also quoted. The microbial
degradation of the compound, particularly in relation to waste clean-up,
has been reviewed recently (Litchfield and Rao, 1998).
Metabolism
Pentachlorophenol was metabolized in rats
by conjugation with glucuronic acid and eliminated as
the glucuronide. P450 catalyzed oxidative dechlorination
also occurred to form tetrachlorohydroquinone, and this
was conjugated to form a monoglucuronide representing
27% of the dose administered. Other metabolites
have been reported, including isomeric tetrachlorophenols,
tetrachlorocatechol and tetrachlororesorcinol. Trace
amounts of benzoquinones were also noted.
Metabolites in female rats were tetrachloromonophenols,
diphenols, and hydroquinones.
Solubility in organics
At 20 °C (g/100 g solution): methanol (57.0), anhydrous ethanol (53.0), 95% ethanol (47.5),
diethylene glycol monomethyl ether (48.0), pine oil (32.0), diethylene glycol monoethyl ether
(30.0), diethylene glycol (27.5), 2-ethoxyethanol (27.0), dioxane (11.5), benzene (11.0), ethylene
glycol (6.0), diesel oil (3.1), fuel oil (2.6) (Carswell and Nason, 1938).
Solubility in water
At 20 °C (g/100 g solution): methanol (57.0), anhydrous ethanol (53.0), 95% ethanol (47.5),
diethylene glycol monomethyl ether (48.0), pine oil (32.0), diethylene glycol monoethyl ether
(30.0), diethylene glycol (27.5), 2-ethoxyethanol (27.0), dioxane (11.5), benzene (11.0), ethylene
glycol (6.0), diesel oil (3.1), fuel oil (2.6) (Carswell and Nason, 1938).
Shipping
UN3155 Pentachlorophenol, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
Purification Methods
Crystallise it twice from toluene/EtOH. Sublime it in vacuo.[Beilstein 6 IV 1025.]
Toxicity evaluation
The toxicology has been addressed in a
recent risk assessment (119). Acutely, pentachlorophenol
was reported to have LD50 values in the rat of 12 mg/kg (inhalation) and 146 mg/kg (M)–175 mg/kg (F) by oral
gavage. More detailed studies of the toxicology of pentachlorophenol
have been compromised by the toxicity of
impurities present in most of the earlier samples used
in the evaluation process.Although a number of toxicity
studies have been conducted with both known impurities
and TCHQ, it is often difficult to know whether
animal experiments are valid for human health risk assessment.
Nevertheless, it appears that the main target organ
of purified TCP in animals is the liver.This toxicity
was manifested as liver inflammation, increased relative
weight, and increased serum alkaline phosphatase. The
estimated chronic NOEL in the dog for these effects was
0.15 mg/kg/day, from a 1-year study, based on a LOEL of 1.5 mg/kg/day. In the rat, a significantly increased
incidence of mesotheliomas (p<0.05) and nasal carcinomas
in males was reported at the highest dose tested,
~60 mg/kg/day.
Degradation
Pentachlorophenol has the typical weak acidic properties of a phenol,
readily forming the sodium salt. At physiological pH a major proportion
is ionised and the metabolism (but not necessarily the mobility and
absorption) of pentachlorophenol and its sodium salt should be very similar.
The laurate ester, being lipophilic, is absorbed more readily than the
phenate ion and it is also more volatile. However, the ester should be
readily hydrolysed in dilute base to pentachlorophenol and lauric acid
and by estersases in vivo to the same products. Thus the metabolism of the
three forms may be considered together.
Pentachlorophenol is rapidly degraded under conditions of aqueous
photolysis in W light and sunlight (Engelhardt et al., 1986). Products
detected (Scheme 1) include the reductive dechlorination products
2,3,4,6- and 2,3,5,6-tetrachlorophenol (2 and 3) and trichlorophenols.
Ring chlorine atoms were displaced by hydroxyl groups to afford
2,3,5,6-tetrachlorohydroquinone (4), tetrachlorocatechol (5) and tetrachlororesorcinol(
6). The hydroquinone (4) was very rapidly decomposed in air. Irradiation of each of 4, 5 and 6 afforded trichlorobenzenediols,
trichloroquinones and 2,3-dichloromaleic acid (7).
Hydroquinone 4 oxidised in the dark (and in light) to 2,3,5,6-
tetrachloro-l,4-benzoquinone (8), the 2-hydroxy analogue (9), the
dichlorohydroxybenzoquinone (10) and the maleic acid (7). The latter
eventually affords CO2 and HCl.
Exposure of an aqueous solution of the sodium salt to sunlight gave
small amounts of octachlorodibenzodioxin but none of the extremely
toxic 2,3,7,8-tetrachloro derivative could be detected. Much of the original
work on the photolysis of pentachlorophenol was reported by Wong and
Crosby (1978).
Incompatibilities
Reacts violently with strong oxidizers,
acids, alkalies, and water.
Waste Disposal
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform with EPA regulations governing
storage, transportation, treatment, and waste disposal.
In accordance with 40CFR165, follow recommendations
for the disposal of pesticides and pesticide containers. Must
be disposed properly by following package label directions
or by contacting your local or federal environmental
control agency, or by contacting your regional EPA office.
Incineration (600°to 900°C) coupled with acequate scrubbing
and ash disposal facilities. Alternatively pentachlorophenol
Check Digit Verification of cas no
The CAS Registry Mumber 87-86-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 87-86:
(4*8)+(3*7)+(2*8)+(1*6)=75
75 % 10 = 5
So 87-86-5 is a valid CAS Registry Number.
InChI:InChI=1/C6HCl5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
87-86-5Relevant articles and documents
Nano Fe3O4@ZrO2/SO42?: A highly efficient catalyst for the protection and deprotection of hydroxyl groups using HMDS under solvent-free condition
Ghafuri, Hossein,Paravand, Fatemeh,Rashidizadeh, Afsaneh
supporting information, p. 129 - 135 (2016/12/24)
In this work, we introduce a new procedure for the protection and deprotection process of various types of alcohols and phenols by HMDS in the presence of nano magnetic sulfated zirconia (Fe3O4@ZrO2/SO42?) as a solid acid catalyst under very mild and solvent-free condition. This method has interesting advantages like short reaction times and a simple workup process. With regard to some outstanding benefits of this new heterogeneous catalyst such as excellent yield, reusability of the catalyst and easy thermal stability, high acidity, strong and excellent magnetic properties, this method can be very interesting in aspect of green chemistry Principles.
Method for reducing microcontaminants during synthesis of pentachlorophenol
-
Page/Page column 5, (2008/06/13)
A method for reducing contaminants during synthesis of pentachlorophenol includes providing a phenol-based starting material and a catalyst, which form a reaction mixture. A chlorine flow is introduced so that it is in contact with the reaction mixture, and the starting material and chlorine are reacted via a temperature-programmed reaction. The chlorine flow is terminated at a predetermined temperature prior to an end of the temperature-programmed reaction and/or at a point where the yield of pentachlorophenol is less than about 95%.
Formation of PCDDs and PCDFs during the combustion of polyvinylidene chloride and other polymers in the presence of HCl
Ohta, Minoru,Oshima, Shozo,Osawa, Naoki,Iwasa, Toshio,Nakamura, Tadashi
, p. 1521 - 1531 (2007/10/03)
PVDC and three non-chlorinated polymers (PP, PET, and PA) were incinerated at 700-850°C in a laboratory-scale quartz tubular furnace in the presence of HCl (ca. 500 ppm?0.8 mg/l), and the gas-phase formation of PCDD/Fs, their putative precursors and their homologue profiles were investigated. The addition of HCl had little or no apparent effect on the level of PCDD/Fs formation during PVDC combustion, and their homologue profiles were quite different from those of the three non-chlorinated polymers. With PVDC, O 8CDD and particularly O8CDF were by far most prevalent, apparently as a result of the selective formation of the precursors. With each of the three non-chlorinated polymers, combustion at 800°C or higher in the presence of HCl resulted in PCDD/Fs formation at levels equaling or exceeding those observed with PVDC. In trials made with one of them (PP) under the same conditions but using a large polymer sample (100 mg vs 20 mg in all other trials), the level of PCDD/Fs formation was far higher than with the smaller polymer samples, and thus demonstrated the importance of appropriate combustion conditions for polymer incineration.