Pentachlorophenol

Base Information

• Chemical Name: Pentachlorophenol
• CAS No.: 87-86-5
• Deprecated CAS: 101802-54-4,39390-77-7,1135443-67-2,1135443-67-2,39390-77-7
• Molecular Formula: C6Cl5OH
• Molecular Weight: 266.338
• Hs Code.: 2908.10 Oral, rat LD50: 27 mg/kg
• European Community (EC) Number: 201-778-6
• ICSC Number: 0069
• NSC Number: 40792,263497
• UN Number: 3155
• UNII: D9BSU0SE4T
• DSSTox Substance ID: DTXSID7021106
• Nikkaji Number: J3.904G
• Wikipedia: Pentachlorophenol
• Wikidata: Q423922
• Metabolomics Workbench ID: 49670
• ChEMBL ID: CHEMBL75967
• Mol file: 87-86-5.mol

Synonyms:Pentachlorophenate, Sodium;Pentachlorophenol;Sodium Pentachlorophenate

Chemical Property of Pentachlorophenol

Chemical Property:

• Appearance/Colour: odourless white or light brown powder or crystals
• Vapor Pressure: 40 mm Hg ( 211.2 °C)
• Melting Point: 165-180 °C(lit.)
• Refractive Index: 1.6310 (estimate)
• Boiling Point: 309.5 °C at 760 mmHg
• PKA: 4.80 (Blackman et al., 1955) 5.3 (Eder and Weber, 1980)
• Flash Point: 133.7 °C
• PSA: 20.23000
• Density: 1.804 g/cm³
• LogP: 4.65920
• Storage Temp.: 0-6°C
• Water Solubility.: 80 mg l-1(30 °C)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 265.844053
• Heavy Atom Count: 12
• Complexity: 150
• Transport DOT Label: Poison

Purity/Quality:

98%+ ^*data from raw suppliers

Pentachlorophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+; N; Xn
• Hazard Codes: T+,N,T,F,Xn
• Statements: 24/25-26-36/37/38-40-50/53-39/23/24/25-23/24/25-11-52/53-51/53
• Safety Statements: 22-36/37-45-52-60-61-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Chlorophenols
• Canonical SMILES: C1(=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)O
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the cardiovascular system. This may result in cardiac disorders and heart failure.
• Effects of Long Term Exposure: The substance may have effects on the central nervous system, kidneys, liver, lungs, immune system and thyroid. This substance is possibly carcinogenic to humans. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• Description: Pentachlorophenol is a restricted use pesticide and is used industrially as a wood preservative for utility poles, railroad ties, and wharf pilings. Pentachlorophenol was widely used as wood preservative until 1987 when its use was restricted to certified applicators. Pentachlorophenol is considered a probable human carcinogen and exposure to high levels can also have other health risks. Pentachlorophenol is a synthetic substance, made from other chemicals, and does not occur naturally in the environment. It is made by only one company in the United States. At one time, it was one of the most widely used biocides in the United States. Since 1984, the purchase and use of pentachlorophenol has been restricted to certified applicators. It is no longer available to the general public. Application of pentachlorophenol in the home as an herbicide and pesticide accounted for only 3% of its consumption in the 1970s. Before use restrictions, pentachlorophenol was widely used as a wood preservative. It is now used industrially as a wood preservative for power line poles, cross arms, fence posts, and the like. Pure pentachlorophenol exists as colorless crystals. It has a very sharp characteristic phenolic smell when hot but very little odor at room temperature. Most people can begin to smell pentachlorophenol in water at less than 12 parts pentachlorophenol per million parts of water (ppm). Impure pentachlorophenol (the form usually found at hazardous waste sites) is dark gray to brown and exists as dust, beads, or flakes. Pentachlorophenol can be found in two forms: pentachlorophenol itself or as the sodium salt of pentachlorophenol. The sodium salt dissolves easily in water, but pentachlorophenol does not. These two forms have some different physical properties, but are expected to have similar toxic effects. Humans are generally exposed to technical-grade pentachlorophenol, which usually contains such toxic impurities as polychlorinated dibenzo- p-dioxins and dibenzofurans.
• Physical properties: 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).
• Uses: Pentachlorophenol is used to control termites and, as the laurate ester, wood boring insects. The ester and the sodium salt are used to protect wood from fungal rot and as general herbicides and defoliants. The sodium salt is also used as a general disinfectant. Pentachlorophenol (PCP) is used for termite control, asa defoliant, and in the preservation of wood and wood products. It is an indoor air pollutant. It has been detected in timbers in the ppm range, causing contamination of air, surfaces, and materials in the homes. Its concentrations in blood samples have been reported in the range of sub-ppb to 110 μ/kg (Ruh et al. 1984). It has been detected in flue gas at 760–870°C (1400–1598°F) exit temperature from an incinerator at a concentration of 1.033 mg/m3 (Guinivan et al. 1985). The incinerator burned pentachlorophenol-treated wooden ammunition boxes and there was no afterburning. Methyl ethers of pentachlorophenol—pentachloroanisole and tetrachlorohydroquinone dimethyl ether —formed from microbial methylation of pentachlorophenol have been identified in the pg/m3 range in marine air samples from both the northern and southern hemispheres (Atlas et al. 1986).. 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. .Insecticide; fungicide; herbicide.

Technology Process of Pentachlorophenol

There total 100 articles about Pentachlorophenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

pentachlorophenol-TMS (62269-80-1) → Pentachlorophenol (87-86-5,67471-28-7)

Guidance literature:

With nano magnetic sulfated zirconia (Fe₃O₄ at ZrO₂/SO₄^2-); In neat (no solvent); at 20 ℃; for 0.833333h; Green chemistry;

DOI:10.1080/10426507.2016.1236104

Reference yield: 50.0%

Quintozene (82-68-8) → Pentachlorophenol (87-86-5,67471-28-7)

Guidance literature:

With sodium hydroxide; In water; for 3h; Heating;

Reference yield: 20.0%

phenol (108-95-2,27073-41-2) → Pentachlorophenol (87-86-5,67471-28-7) + 2,3,4,6-tetrachlorophenol (58-90-2)

Guidance literature:

With chlorine; aluminum (III) chloride; at 100 - 180 ℃; for 10.8333h; Product distribution / selectivity;

upstream raw materials:

tetrachloromethane

3-Iodophenol

3,5-dihydroxyphenol

ethanol

Downstream raw materials:

nonanoic acid pentachlorophenyl ester

1-(2,4-dichloro-phenoxy)-2-pentachlorophenoxy-ethane

pentachlorophenyl-picryl ether

2-pentachlorophenoxy-butyric acid methyl ester

Refernces

• 1、 -. "Sodium pentachlorophenol liquid product preparation method". Paragraph 0016; 0017. . Retrieved 2017/01/12.
• 2、 Ohta, Minoru,Oshima, Shozo,Osawa, Naoki,Iwasa, Toshio,Nakamura, Tadashi. "Formation of PCDDs and PCDFs during the combustion of polyvinylidene chloride and other polymers in the presence of HCl". . p. 1521 - 1531. Retrieved 2007/10/03.