Hexachlorobenzene
Encyclopedia
Hexachlorobenzene, or perchlorobenzene, is a chlorocarbon
with the molecular formula C6Cl6. It is a fungicide
formerly used as a seed treatment, especially on wheat to control the fungal disease bunt
. It has been banned globally under the Stockholm Convention
on persistent organic pollutants.
, benzene
, ethanol
and chloroform
. Its vapour pressure is 1.09×10−5 mmHg (1.45 mPa) at 20 °C. Its flash point is 242 °C and it sublimes at 322 °C.
and is considered to be a probable human carcinogen. After its introduction as a fungicide in 1945, for crop seeds, this toxic chemical was found in all food types. Hexachlorobenzene was banned from use in the United States in 1966.
This material has been classified by the International Agency for Research on Cancer
(IARC) as a Group 2B carcinogen (possibly carcinogenic to humans). Animal carcinogenicity data for hexachlorobenzene show increased incidences of liver
, kidney
(renal tubular tumours) and thyroid cancer
s. Chronic oral exposure in humans has been shown to give rise to a liver disease (porphyria cutanea tarda
), skin lesions with discoloration, ulceration, photosensitivity
, thyroid effects, bone effects and loss of hair. Neurological changes have been reported in rodents exposed to hexachlorobenzene. Hexachlorobenzene may cause embryolethality and teratogenic effects. Human and animal studies have demonstrated that hexachlorobenzene crosses the placenta to accumulate in foetal tissues and is transferred in breast milk.
HCB is very toxic to aquatic organisms. It may cause long term adverse effects in the aquatic environment
. Therefore, release into waterways should be avoided. It is persistent in the environment. Ecological investigations have found that biomagnification
up the food chain does occur. Hexachlorobenzene has a half life in the soil of between 3 and 6 years. Risk of bioaccumulation in an aquatic species is high.
Material has relatively low acute toxicity but is toxic because of its persistent and cumulative nature in body tissues in rich lipid content.
, Turkey between 1955 and 1959, during a period when bread wheat was unavailable, 500 people were fatally poisoned and more than 4,000 people fell ill by eating bread made with HCB-treated seed that was intended for agriculture use. Most of the sick were affected with a liver condition called porphyria cutanea tarda, which disturbs the metabolism of hemoglobin and results in skin lesions. Almost all breastfeeding children under the age of two, whose mothers had eaten tainted bread, died from a condition called "pembe yara" or "pink sore," most likely from high doses of HCB in the breast milk. In one mother's breast milk the HCB level was found to be 20 parts per million in lipid, approximately 2,000 times the average levels of contamination found in breast-milk samples around the world. Follow-up studies 20 to 30 years after the poisoning found average HCB levels in breast milk were still more than seven times the average for unexposed women in that part of the world (56 specimens of human milk obtained from mothers with porphyria, average value was 0.51 ppm in HCB-exposed patients compared to 0.07 ppm in unexposed controls), and 150 times the level allowed in cow's milk.
In the same follow-up study of 252 patients (162 males and 90 females, avg. current age of 35.7 years), 20–30 years postexposure, many subjects had dermatologic, neurologic, and orthopedic symptoms and signs. The observed clinical findings include scarring of the face and hands (83.7%), hyperpigmentation (65%), hypertrichosis (44.8%), pinched faces (40.1%), painless arthritis (70.2%), small hands (66.6%), sensory shading (60.6%), myotonia (37.9%), cogwheeling (41.9%), enlarged thyroid (34.9%), and enlarged liver (4.8%). Urine and stool porphyrin levels were determined in all patients, and 17 have at least one of the porphyrins elevated. Offspring of mothers with three decades of HCB-induced porphyria appear normal.
Organochloride
An organochloride, organochlorine, chlorocarbon, chlorinated hydrocarbon, or chlorinated solvent is an organic compound containing at least one covalently bonded chlorine atom. Their wide structural variety and divergent chemical properties lead to a broad range of applications...
with the molecular formula C6Cl6. It is a fungicide
Fungicide
Fungicides are chemical compounds or biological organisms used to kill or inhibit fungi or fungal spores. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality and profit. Fungicides are used both in agriculture and to fight fungal infections in animals...
formerly used as a seed treatment, especially on wheat to control the fungal disease bunt
Karnal bunt
Karnal bunt is a fungal disease of wheat, durum wheat, and triticale. The smut fungus Tilletia indica invades the kernels and obtains its nutrition from the endosperm, leaving behind waste products with a disagreeable odor that makes bunted kernels too unpalatable for use in flour.-Origin and...
. It has been banned globally under the Stockholm Convention
Stockholm Convention
Stockholm Convention on Persistent Organic Pollutants is an international environmental treaty, signed in 2001 and effective from May 2004, that aims to eliminate or restrict the production and use of persistent organic pollutants .- History :...
on persistent organic pollutants.
Physical and chemical properties
HCB is a white crystalline solid that has negligible solubility in water. It is soluble in diethyl etherDiethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...
, benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
, ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
and chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...
. Its vapour pressure is 1.09×10−5 mmHg (1.45 mPa) at 20 °C. Its flash point is 242 °C and it sublimes at 322 °C.
Safety
Hexachlorobenzene is an animal carcinogenCarcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...
and is considered to be a probable human carcinogen. After its introduction as a fungicide in 1945, for crop seeds, this toxic chemical was found in all food types. Hexachlorobenzene was banned from use in the United States in 1966.
This material has been classified by the International Agency for Research on Cancer
International Agency for Research on Cancer
The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organisation of the United Nations....
(IARC) as a Group 2B carcinogen (possibly carcinogenic to humans). Animal carcinogenicity data for hexachlorobenzene show increased incidences of liver
Liver cancer
Liver tumors or hepatic tumors are tumors or growths on or in the liver . Several distinct types of tumors can develop in the liver because the liver is made up of various cell types. These growths can be benign or malignant...
, kidney
Kidney cancer
Kidney cancer is a type of cancer that starts in the cells in the kidney.The two most common types of kidney cancer are renal cell carcinoma and urothelial cell carcinoma of the renal pelvis...
(renal tubular tumours) and thyroid cancer
Thyroid cancer
Thyroid neoplasm is a neoplasm or tumor of the thyroid. It can be a benign tumor such as thyroid adenoma, or it can be a malignant neoplasm , such as papillary, follicular, medullary or anaplastic thyroid cancer. Most patients are 25 to 65 years of age when first diagnosed; women are more affected...
s. Chronic oral exposure in humans has been shown to give rise to a liver disease (porphyria cutanea tarda
Porphyria cutanea tarda
Porphyria cutanea tarda is the most common subtype of porphyria. The disorder results from low levels of the enzyme responsible for the fifth step in heme production. Heme is a vital molecule for all of the body's organs...
), skin lesions with discoloration, ulceration, photosensitivity
Photosensitivity
Photosensitivity is the amount to which an object reacts upon receiving photons, especially visible light.- Human medicine :Sensitivity of the skin to a light source can take various forms. People with particular skin types are more sensitive to sunburn...
, thyroid effects, bone effects and loss of hair. Neurological changes have been reported in rodents exposed to hexachlorobenzene. Hexachlorobenzene may cause embryolethality and teratogenic effects. Human and animal studies have demonstrated that hexachlorobenzene crosses the placenta to accumulate in foetal tissues and is transferred in breast milk.
HCB is very toxic to aquatic organisms. It may cause long term adverse effects in the aquatic environment
Ecosystem
An ecosystem is a biological environment consisting of all the organisms living in a particular area, as well as all the nonliving , physical components of the environment with which the organisms interact, such as air, soil, water and sunlight....
. Therefore, release into waterways should be avoided. It is persistent in the environment. Ecological investigations have found that biomagnification
Biomagnification
Biomagnification, also known as bioamplification or biological magnification, is the increase in concentration of a substance that occurs in a food chain as a consequence of:* Persistence...
up the food chain does occur. Hexachlorobenzene has a half life in the soil of between 3 and 6 years. Risk of bioaccumulation in an aquatic species is high.
Toxicology
- Oral LD50 (rat): 10,000 mg/kg
- Oral LD50 (mice): 4,000 mg/kg
- Inhalation LC50 (rat): 3600 mg/m3
Material has relatively low acute toxicity but is toxic because of its persistent and cumulative nature in body tissues in rich lipid content.
Unique Exposure Incident
In AnatoliaAnatolia
Anatolia is a geographic and historical term denoting the westernmost protrusion of Asia, comprising the majority of the Republic of Turkey...
, Turkey between 1955 and 1959, during a period when bread wheat was unavailable, 500 people were fatally poisoned and more than 4,000 people fell ill by eating bread made with HCB-treated seed that was intended for agriculture use. Most of the sick were affected with a liver condition called porphyria cutanea tarda, which disturbs the metabolism of hemoglobin and results in skin lesions. Almost all breastfeeding children under the age of two, whose mothers had eaten tainted bread, died from a condition called "pembe yara" or "pink sore," most likely from high doses of HCB in the breast milk. In one mother's breast milk the HCB level was found to be 20 parts per million in lipid, approximately 2,000 times the average levels of contamination found in breast-milk samples around the world. Follow-up studies 20 to 30 years after the poisoning found average HCB levels in breast milk were still more than seven times the average for unexposed women in that part of the world (56 specimens of human milk obtained from mothers with porphyria, average value was 0.51 ppm in HCB-exposed patients compared to 0.07 ppm in unexposed controls), and 150 times the level allowed in cow's milk.
In the same follow-up study of 252 patients (162 males and 90 females, avg. current age of 35.7 years), 20–30 years postexposure, many subjects had dermatologic, neurologic, and orthopedic symptoms and signs. The observed clinical findings include scarring of the face and hands (83.7%), hyperpigmentation (65%), hypertrichosis (44.8%), pinched faces (40.1%), painless arthritis (70.2%), small hands (66.6%), sensory shading (60.6%), myotonia (37.9%), cogwheeling (41.9%), enlarged thyroid (34.9%), and enlarged liver (4.8%). Urine and stool porphyrin levels were determined in all patients, and 17 have at least one of the porphyrins elevated. Offspring of mothers with three decades of HCB-induced porphyria appear normal.