ペンタクロロフェノール 化学特性,用途語,生産方法
外観
白色～ほとんど白色, 結晶～結晶性粉末
溶解性
水に難溶 (0.001g/100ml水, 20℃), エタノール, エーテルに可溶。エタノールに溶けやすく、水にほとんど溶けない。
解説
ペンタクロロフェノール刺激臭のある白色の針状晶．融点191 ℃(無水物)，174 ℃(一水和物)，沸点309～310 ℃．d22 1.978．pKa 8.2(メタノール)．有機溶媒に易溶，水に不溶．鼻，のどを刺激する．LD50 210 mg/kg(ラット，経口)．労働安全衛生法に規定があり，許容濃度0.5 ppm．
用途
木材の防腐剤，農業用殺菌剤(果樹用)に用いられる．魚毒性が強いため，除草剤としての使用が規制されている特定化学物質．
製造
ペンタクロロフェノール略称PCP．フェノールを触媒の存在下に塩素化すると得られる．
化学的特性
Pentachlorophenol is a colorless to white,
crystalline solid. It has a benzene-like odor; pungent when
hot. The Odor Threshold in water is 1600 μg/L and the
taste threshold in water is 30 μg/L.
物理的性質
White flakes or needles with a phenolic odor. At 40 °C, the average odor threshold concentration
and the lowest concentration at which an odor was detected were 23 and 9.3 μg/L, respectively. At
25 °C, the lowest concentration at which a taste was detected was 8 μg/L (Young et al., 1996).
使用
Pentachlorophenol (PCP) is an odourless, white or light brown powder or crystal in appearance. It is used as herbicide and fungicide. Pentachlorophenol is incompatible with strong oxidising agents. Pentachlorophenol has a very sharp characteristic phenolic smell when hot but very little odour at room temperature. Pentachlorophenol is a synthetic substance made from other chemicals and does not occur naturally in the environment. Initially pentachlorophenol was widely used as a wood preservative. It is now used industrially as a wood preservative for power line poles, cross arms, fence post, etc.
Used as insecticide for terminate control; pre-harvest defoliant; general herbicide. Antimicrobial preservative and fungicide for wood, wood products, starches, textiles, paints, adhesives, leather, pulp, paper, industrial waste systems, building materials. Surface disinfectant.
定義
ChEBI: A chlorophenol that is phenol substituted by 5 chloro groups.
調製方法
Pentachlorophenol can be produced by the chlorination of phenol in the presence of AlCl3, or by hydrolysis of hexachlorobenzene with NaOH in methanol.
一般的な説明
A white crystalline solid. Slightly soluble in water. Noncombustible. Toxic by inhalation, ingestion, and skin absorption. Used as a fungicide and as a wood preservative.
空気と水の反応
Slightly soluble in water.
反応プロフィール
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 .
健康ハザード
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.
火災危険
Special Hazards of Combustion Products: Generates toxic and irritating vapors.
使用用途
ペンタクロロフェノールは、過去には農薬、殺菌剤、木材保護材、植物成長調節剤、水田用除草剤等に使用・登録されていましたが、現在は、失効されております。
また、発がん性や強い魚毒性、環境ホルモン様物質などと疑われているため、2015年スイスのジュネーブにおいて、ストックホルム条約の締約国会議(COP7)で、新たにペンタクロロフェノールとその塩及びエステル類が同条約の附属書A（廃絶）に追加されることが決定されました。
农业用途
Fungicide, Herbicide, Slimicide, Wood
preservative: Pentachlorophenol (PCP) is a commercially produced
insecticide, fungicide, and slimicide. Since 1984 it
has been restricted to certified applicators and is no longer
available to the general public. It is primarily used to protect
timber from fungal rot and wood-boring insects, but
may also be used as a pre-harvest defoliant in cotton, a general
pre-emergence herbicide, and as a biocide in industrial
water systems. Not approved for use in EU countries.
Not registered for use in the U.S. There are 48 global
suppliers.
製品名
(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®
安全性プロファイル
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
職業ばく露
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
発がん性
The IARC has determined that there is
limited evidence for carcinogenicity in humans
and sufficient evidence of carcinogenicity in
experimental animals.
環境運命予測
Biological. Under aerobic conditions, microbes in estuarine water partially dechlorinated pentachlorophenol to trichlorophenol (Hwang et al., 1986). The disappearance of
pentachlorophenol 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 (Freitag
Pentachlorophenol 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
代謝
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.
輸送方法
UN3155 Pentachlorophenol, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
純化方法
Crystallise it twice from toluene/EtOH. Sublime it in vacuo.[Beilstein 6 IV 1025.]
不和合性
Reacts violently with strong oxidizers,
acids, alkalies, and water.
廃棄物の処理
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
ペンタクロロフェノール 上流と下流の製品情報
原材料
準備製品