| Identification | More | [Name]
HEXACHLOROBENZENE | [CAS]
118-74-1 | [Synonyms]
1,2,3,4,5,6-HEXACHLOROBENZENE
ANTICARIE(R)
BENZENE HEXACHLORIDE
bexachlorobenzene
BUNT-CURE(R)
BUNT-NO-MORE(R)
HCB
HCB(R)
Hexachlorbenzd
HEXACHLOROBENZENE
Hexachlorocyclohexane
JULIN'S CARBON CHLORIDE
'LGC' (1131)
NO BUNT
PERCHLOROBENZENE
ai3.01719
Amatin
Anticarie
Antitcatil
Bunt-cure | [EINECS(EC#)]
204-273-9 | [Molecular Formula]
C6Cl6 | [MDL Number]
MFCD00000540 | [Molecular Weight]
284.78 | [MOL File]
118-74-1.mol |
| Chemical Properties | Back Directory | [Description]
Hexachlorobenzene is a white crystalline solid. This compound does not occur naturally.
It is formed as a by-product during the manufacture of chemicals used as solvents
(substances used to dissolve other substances), other chlorine-containing compounds,
and pesticides. Small amounts of hexachlorobenzene can also be produced during combustion
processes such as burning of city wastes. It may also be produced as a by-product
in waste streams of chlor-alkali and wood-preserving plants. Hexachlorobenzene
was widely used as a pesticide until 1965. It was also used to make fireworks, ammunition,
and synthetic rubber. | [Appearance]
Hexachlorobenzene is a solid, crystallizing in nee dles. | [Melting point ]
227-229 °C(lit.) | [Boiling point ]
323-326 °C(lit.) | [density ]
1.5691 | [vapor pressure ]
1.45 x l0-3 Pa (20 °C) | [refractive index ]
1.5691 (estimate) | [Fp ]
11 °C | [storage temp. ]
APPROX 4°C
| [solubility ]
Chloroform, Hexanes (Slightly) | [form ]
neat | [Water Solubility ]
Practically insoluble in water | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Merck ]
13,4696 | [BRN ]
1912585 | [Henry's Law Constant]
6.11 at 25 °C (continuous flow sparger, Sproule et al., 1991) | [Exposure limits]
No exposure limit has been set for this com pound. Carcinogenicity: Animal Sufficient
Evidence, Human Limited Evidence (IARC). | [InChIKey]
CKAPSXZOOQJIBF-UHFFFAOYSA-N | [CAS DataBase Reference]
118-74-1(CAS DataBase Reference) | [IARC]
2B (Vol. Sup 7, 79) 2001 | [EPA Substance Registry System]
Hexachlorobenzene (118-74-1) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,Xn,F,Xi | [Risk Statements ]
R45:May cause cancer.
R48/25:Toxic: danger of serious damage to health by prolonged exposure if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R62:Possible risk of impaired fertility.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation .
R38:Irritating to the skin.
R11:Highly Flammable.
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R66:Repeated exposure may cause skin dryness or cracking.
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S36/37:Wear suitable protective clothing and gloves .
S33:Take precautionary measures against static discharges .
S29:Do not empty into drains .
S16:Keep away from sources of ignition-No smoking .
S9:Keep container in a well-ventilated place .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 2729 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
DA2975000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
2903920000 | [Hazardous Substances Data]
118-74-1(Hazardous Substances Data) | [Toxicity]
LC50 for ?ve freshwater species 0.05-0.2 mg/L (Hartley and Kidd, 1987); acute oral LD50 for rats 10,000 mg/kg (RTECS, 1985).
|
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Hydrochloric acid-->1,2,4-Trichlorobenzene-->fulvene-->1,3,5-Trichlorobenzene | [Preparation Products]
Sodium pentachlorophenolate-->PENTACHLOROTHIOPHENOL-->Quintozine-->PENTACHLOROPHENOL ACETATE-->2,3,4,5,6-PENTACHLOROTOLUENE-->hexafluorobenzene-->Carbon tetrachloride-->3,4,5,6-Tetrachloro-1,2-benzenedithiol |
| Hazard Information | Back Directory | [General Description]
A white crystalline substance. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals. | [Reactivity Profile]
HEXACHLOROBENZENE(118-74-1) reacts violently with dimethylformamide. . | [Air & Water Reactions]
This chemical is sensitive to moisture. Insoluble in water. | [Hazard]
Possible carcinogen. Toxic by ingestion.
Combustible. | [Health Hazard]
Harmful by dust inhalation or if swallowed. Irritating to eyes, skin and mucous membranes. Prolonged periods of ingestion may cause cutaneous porphyria. | [Potential Exposure]
Hexachlorobenzene was used as a fun gicide; an additive for pyrotechnic compositions; and as
wood preservative. It was used widely as a pesticide to pro tect seeds of onions and sorghum, wheat, and other grains
against fungus until 1965. This material was used to make
fireworks; ammunition for military uses; synthetic rubber;
as a porosity controller in the manufacture of electrodes; as
an intermediate in dye manufacture; in organic synthesis. It
is formed as a by-product of making other chemicals; in
the waste streams of chloralkali and wood-preserving
plants; and when burning municipal waste. Currently, there
are no commercial uses of hexachlorobenzene in the United
States. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, includ ing resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medi cal attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit. Note
to Physician: For ingestions of less than 10 mg/kg body
weight occurring less than an hour before treatment, induce
emesis. For ingestions of more than 10 mg/kg body weight
occurring less than an hour before treatment, use gastric
lavage. For ingestion occurring more than an hour before
treatment, use activated charcoal. There is no specific anti dote, and supervision for at least 72 hours is recommended.
Personal Protective Methods: Wear protective eye protec tion, gloves, and clothing to prevent any reasonable
probability of skin or eye contact. Safety equipment suppliers/manufacturers can provide recommendations on
the most protective glove/clothing material for your opera tion. All protective clothing (suits, gloves, footwear, head gear) should be clean, available each day, and put on
before work. Contact lenses should not be worn when
working with this chemical. Wear dust-proof chemical gog gles and face shield unless full facepiece respiratory protec tion is worn. Employees should wash immediately with
soap when skin is wet or contaminated. Provide emergency
showers and eyewash. | [Shipping]
UN2729 Hexachlorobenzene, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials. | [Incompatibilities]
Reacts violently with oxidizers; dimethyl
formamide above 65 ℃. | [Chemical Properties]
Hexachlorobenzene is a solid, crystallizing in nee dles. | [Chemical Properties]
white powder | [Waste Disposal]
Incineration is most effective
@ 1300 ℃ and 0.25 seconds. Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform to EPA regulations governing
storage, transportation, treatment, and waste disposal. | [Uses]
Hexachlorobenzene is used as a fungicideand as an intermediate in organic synthesis. | [Uses]
In organic syntheses. Formerly as agricultural fungicide. | [Uses]
No commercial uses of hexachlorobenzene as an end product in the United States were identified (ATSDR 2002). Previously, it was used as a seed-treatment fungicide for onions, sorghum, wheat, and other grains (IARC 1979). All registered pesticide uses in the United States were voluntarily cancelled in 1984 (ATSDR 2002). Hexachlorobenzene was also used as a chemical intermediate in dye manufacturing, in the synthesis of other organic chemicals, and in the production of pyrotechnic compositions for the military. It was used as a raw material for synthetic rubber, as a plasticizer for polyvinyl chloride, as a porosity controller in the manufacture of electrodes, and as a wood preservative (IARC 1979, ATSDR 2002). | [Uses]
Seed fungicide | [Definition]
ChEBI: A member of the class of chlorobenzenes that is benzene in which all of the hydrogens are replaced by chlorines. An agricultural fungicide introduced in the mid-1940s and formerly used as a seed treatment, its use has been banned since 1984 under the Stock
olm Convention on Persistent Organic Pollutants. | [Definition]
hexachlorobenzene: A colourlesscrystalline compound, C6Cl6; m.p.227°C. It is made by the chlorinationof benzene with an iron(III) chloridecatalyst or by treating hexachlorocyclohexanewith chlorine in hexachloroethane.It is used to preservewood and dress seeds, and in themanufacture of hexafluorobenzene. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 69, p. 3146, 1947 DOI: 10.1021/ja01204a507 | [Fire Hazard]
Noncombustible solid; very low reactiv ity. Reaction with dimethyl formamide is
reported to be violent at temperatures above
65°C (149°F) (NFPA 1997). | [Carcinogenicity]
Hexachlorobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. | [Source]
Hexachlorobenzene may enter the environment from incomplete combustion of
chlorinated compounds including mirex, kepone, chlorobenzenes, pentachlorophenol, PVC,
polychlorinated biphenyls, and chlorinated solvents (Ahling et al., 1978; Dellinger et al., 1991). In
addition, hexachlorobenzene may enter the environment as a reaction by-product in the production
of carbon tetrachloride, dichloroethylene, hexachlorobutadiene, trichloroethylene, tetrachloroethylene,
pentachloronitrobenzene, and vinyl chloride monomer (quoted, Verschueren, 1983). | [Environmental Fate]
Biological. Reductive monodechlorination occurred in an anaerobic sewage sludge yielding principally 1,3,5-trichlorobenzene. Other compounds identified included pentachlorobenzene, 1,2,3,5-tetrachlorobenzene and dichlorobenzenes (Fathepure et al., 1988). In activated sludge, only 1.5% of the applied hexachlorobenzene mineralized to carbon dioxide after 5 days (Freitag et al., 1985). In a 5-day experiment, 14C-labeled hexachlorobenzene applied to soil-water suspensions under aerobic and anaerobic conditions gave 14CO2 yields of 0.4 and 0.2%, respectively (Scheunert et al., 1987).
When hexachlorobenzene was statically incubated in the dark at 25°C with yeast extract and settled domestic wastewater inoculum, no signi?cant biodegradation was observed. At a concentration of 5 mg/L, percent losses after 7, 14, 21 and 28-day incubation
Groundwater. According to the U.S. EPA (1986) hexachlorobenzene has a high potential to leach to groundwater.
Photolytic. Solid hexachlorobenzene exposed to arti?cial sunlight for 5 months photolyzed at a very slow rate with no decomposition products identified (Plimmer and Klingebiel, 1976). The sunlight irradiation of hexachlorobenzene (20 g) in a 100 mL borosilicate glass-stoppered Erlenmeyer ?ask for 56 days yielded 64 ppm pentachlorobiphenyl (Uyeta et al., 1976). A carbon dioxide yield <0.1% was observed when hexachlorobenzene adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 hours (Freitag et al., 1985).
Irradiation (λ ≥285 nm) of hexachlorobenzene (1.1–1.2 mM/L) in an acetonitrile-water mixture containing acetone (concentration = 0.553 mM/L) as a sensitizer gave the following products (% yield): pentachlorobenzene (71.0), 1,2,3,4-tetrachlorobenzene (0.6) | [Metabolic pathway]
With the incubation of rat liver microsomes,
hexachlorobenzene is metabolized to give
pentachlorophenol and tetrachlorohydroquinone, and,
in addition, a considerable amount of covalent binding
to protein is detected (250 pM pentachlorophenol,
17 pM tetrachlorohydroquinone, and 11 pM
tetrachlorobenzoquinone covalent binding in an
incubation containing 50 μM hexachlorobenzene). | [Metabolism]
Sensitized photolysis of HCB at wavelengths greater
than 285 nm in acetonitrile/water containing acetone gave
dechlorinated products: pentachlorobenzene (78) (71%),
1,2,3,4-tetrachlorobenzene (79) (0.6%), 1,2,3,5-tetrachlorobenzene
(80) (2.2%), and 1,2,4,5- tetrachlorobenzene
(81) (3.7%). Without acetone, products included
pentachlorobenzene (78) (76.8%), 1,2,3,5-tetrachlorobenzene
(80) (1.2%), 1,2,4,5- tetrachlorobenzene (81) (1.7%),
and 1,2,4-trichlorobenzene (82) (0.2%) (105).
Irradiation of hexachlorobenzene in methanol solution
at wavelengths greater than 260 nm gave a
mixture of reductively dechlorinated products (pentachlorobenzene
and a tetrachlorobenzene, probably 80)
and pentachlorobenzyl alcohol 83, and also a tetrachlorodi(
hydroxymethyl)benzene (106). A similar product
mixture was obtained by exposing a methanolic solution of
hexachlorobenzene inmethanol to sunlight outdoors. After
15 days, only 30% of hexachlorobenzene was recovered.
Photolysis rates were enhanced by the addition of sensitizers
(diphenylamine, tryptophane, and naturally occurring
organic substances), but no products were identified.
In an anaerobic sewage sludge, hexachlorobenzene was
reductively dechlorinated and the principal product was
1,3,5-trichlorobenzene (84). Pentachlorobenzene, 1,2,3,5-
tetrachlorobenzene, and dichlorobenzenes were also identified
(107). In activated sludge, 1.5% of hexachlorobenzene
was mineralized as carbon dioxide after 5 days. | [Solubility in organics]
In millimole fraction at 25 °C: 2.62 in n-hexane, 3.14 in n-heptane, 3.71 in n-octane, 4.10 in nnonane,
4.60 in n-decane, 6.81 in n-hexadecane, 2.95 in cyclohexane, 3.87 in methylcyclohexane,
2.52 in 2,2,4-trimethylpentane, 4.71 in tert-butylcyclohexane, 4.40 in dibutyl ether, 3.20
in methyl tert-butyl ether, 5.92 in tetrahydrofuran, 3.97 in 1,4-dioxane, 0.0902 in methanol,
0.236 in ethanol, 0.398 in 1-propanol, 0.298 in 2-propanol, 0.667 in 1-butanol, 0.521 in 2-
butanol, 0.533 in 2-methyl-1-propanol, 0.517 in 2-methyl-2-propanol, 1.03 in 1-pentanol, 0.860
in 2-propanol, 0.770 in 3-methyl-1-butanol, 1.20 on 2-methyl-2-butanol, 1.44 in 1-hexanol, 1.40
in 2-methyl-1-pentanol, 1.43 in 4-methyl-2-pentanol, 1.90 in 1-heptanol, 2.38 in 1-octanol, 1.74
in 2-ethyl-1-hexanol, 3.80 in 1-decanol, 0.920 in cyclopentanol, 3.65 in butyl acetate, 2.11 in
ethyl acetate, 1.48 in methyl acetate, 2.86 in 1,2-dichloroethane, 3.83 in 1-chlorobutane, 5.08 in
1-chlorohexane, 6.06 in 1-chlorooctane, 6.10 in chlorocyclohexane (De Fina et al., 2000) | [Solubility in water]
In millimole fraction at 25 °C: 2.62 in n-hexane, 3.14 in n-heptane, 3.71 in n-octane, 4.10 in nnonane,
4.60 in n-decane, 6.81 in n-hexadecane, 2.95 in cyclohexane, 3.87 in methylcyclohexane,
2.52 in 2,2,4-trimethylpentane, 4.71 in tert-butylcyclohexane, 4.40 in dibutyl ether, 3.20
in methyl tert-butyl ether, 5.92 in tetrahydrofuran, 3.97 in 1,4-dioxane, 0.0902 in methanol,
0.236 in ethanol, 0.398 in 1-propanol, 0.298 in 2-propanol, 0.667 in 1-butanol, 0.521 in 2-
butanol, 0.533 in 2-methyl-1-propanol, 0.517 in 2-methyl-2-propanol, 1.03 in 1-pentanol, 0.860
in 2-propanol, 0.770 in 3-methyl-1-butanol, 1.20 on 2-methyl-2-butanol, 1.44 in 1-hexanol, 1.40
in 2-methyl-1-pentanol, 1.43 in 4-methyl-2-pentanol, 1.90 in 1-heptanol, 2.38 in 1-octanol, 1.74
in 2-ethyl-1-hexanol, 3.80 in 1-decanol, 0.920 in cyclopentanol, 3.65 in butyl acetate, 2.11 in
ethyl acetate, 1.48 in methyl acetate, 2.86 in 1,2-dichloroethane, 3.83 in 1-chlorobutane, 5.08 in
1-chlorohexane, 6.06 in 1-chlorooctane, 6.10 in chlorocyclohexane (De Fina et al., 2000) | [storage]
Color Code- Blue: Health Hazard/Poison: Storeinia securepoison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, well-ventilated area away from oxidizers, dimethyl formamide,and heat. Where possible, automatically pump liquid fromdrums or other storage containers to process containers. Aregulated, marked area should be established where thischemical is handled, used, or stored in compliance withOSHA Standard 1910.1045. | [Purification Methods]
Crystallise hexachlorobenzene repeatedly from *benzene. Dry it under vacuum over P2O5. [Beilstein 5 H 205, 5 IV 670.] | [Degradation]
Hexachlorobenzene is very stable and is unreactive toward acids and
bases.
Photolysis is very slow and in artificial sunlight, solid HCB photodecomposed
after 5 months. In sunlight, 20 g of HCB contained in a borosilicate flask gave a concentration of 64 mg kg-1 of pentachlorobiphenyl
after 56 days (Uyeta et al., 1976).
Sensitised photolysis of HCB in an acetonitrile/water mixture containing
acetone at wavelengths greater than 285 nm gave the following products:
pentachlorobenzene (2) (71%), 1,2,3,4-tetrachlorobenzene (3)
(0.6%), 1,2,3,5-tetrachlorobenzene (4) (2.2%) and 1,2,4,5-tetrachlorobenzene
(5) (3.7%). In the absence of acetone, products identified included
2 (76.8%), 4 (1.2%), 5 (1.7%) and 1,2,4-trichlorobenzene (6) (0.2%)
(Choudhry and Hutzinger, 1984) (see Scheme 1). | [Toxicity evaluation]
There are no reports of avian casualties, although raptors
found dead in The Netherlands had substantial levels
of HCB in their livers along with cyclodiene and DDE
residues (33). The same authors reported porphyria in
quail following a 3-month dosing period with 20-ppm
HCB. Product registrations in Canada at the time allowed
up to 1000 ppm on various cereal seeds. In the early
1970s, levels in the range of 3–4 ppm (fresh weight
basis) were seen in eggs of fish-eating birds of the
Great Lakes and likely contributed to the high levels
of embryonic mortality seen (34). However, because HCB
is also an intermediate in the manufacture of several
chemicals, industrial pollution rather than use of the
chemical on farm fields could have been the source of
the contamination. |
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