General Description
A colorless liquid with a mild odor. Insoluble in water and denser than water. Nonflammable. May be toxic by ingestion or inhalation. Used as a solvent and heat transfer fluid.
Reactivity Profile
HEXACHLOROBUTADIENE(87-68-3) rapidly decomposes rubber on contact. Can react vigorously with oxidizing materials. Reacts to form an explosive product with bromine perchlorate. . Gives highly toxic and irritating chloride fumes when burned.
Air & Water Reactions
Insoluble in water.
Hazard
Toxic by ingestion and inhalation, a questionable carcinogen.
Health Hazard
Poisonous; may be fatal if inhaled, swallowed or absorbed through the skin. Inhalation causes repiratory difficulty and irritation of mucous membranes. Skin and eye irritant; may cause burns.
Potential Exposure
Hexachlorobutadiene is used as a sol vent; heat-transfer fluid; transformer fluid; hydraulic fluid;
as a solvent for elastomers; as a wash liquor for removing
higher hydrocarbons.
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.
Shipping
UN2279 Hexachlorobutadiene, Hazard Class:
6.1; Labels: 6.1-Poisonous materials.
Incompatibilities
Strong reaction with oxidizers, aluminum
powder. Attacks aluminum; some plastics, rubber and coatings
Description
Hexachlorobutadiene was first synthesized in 1877 by chlorination
of hexyl iodide. It is an industrial by-product of
tetrachloroethylene, trichloroethylene, and perchloroethylene
production.
Chemical Properties
colourless liquid (typical odour recognition threshold:
Chemical Properties
Hexachlorobutadiene is a clear, colorless
liquid with a faint, turpentine-like odor.
Waste Disposal
High temperature incineration
with flue gas scrubbing. 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.
Physical properties
Clear, yellowish-green liquid with a mild to pungent, turpentine-like odor. Odor threshold
concentration is 6 ppb (quoted, Keith and Walters, 1992).
Uses
Hexachloro-1,3-butadiene is used as an urinary biomarker as a tool for early screening of potential kidney toxicity. Hexachloro-1,3-butadiene (HCBD) causes kidney injury.
Uses
Intermediate in the manufacture of rubber Compounds, chlorofluorocarbons, and lubricants. Hydraulic fluid, fluid for gyroscopes, heat transfer fluid, solvent, laboratory reagent. Soil fumigant for vineyards.
Uses
Produced as an unwanted by-product
during the production of tetrachloroethylene,
trichloroethylene, carbon tetrachloride, and
chlorine; formerly used as a pesticide in other
countries
Definition
ChEBI: Hexachloro-1,3-butadiene is an organochlorine compound.
Carcinogenicity
In rats given oral administration, it produced
benign and malignant tumors in the kidneys in both
sexes. The IARC then concluded that there is limited evidence
that HCBD is carcinogenic in rats.
Nakagawa et al. reported that HCBD is a potent nephrotoxicant
that selectively damaged the straight portion (pars
recta) of the proximal tubule in the rat. They also
reported administering 0.1% HCBD for 30 weeks to male
Wistar rats previously given 0.1% N-ethyl-N-hydroxyethylnitrosamine
(EHEN) in their drinking water for 2 weeks and
that the combined treatment resulted in a significantly higher
incidence of renal cell tumors than when EHEN was administered
alone.
Source
Hydraulic fluids and rubber (quoted, Verschueren, 1983). An impurity in aldrin.
Environmental Fate
Chemical/Physical. Hexachlorobutadiene will not hydrolyze to any reasonable extent (Kollig,
1993).
At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities
were 258, 91, 21, and 11 mg/g, respectively (Dobbs and Cohen, 1980).
Metabolic pathway
In the presence of glutathione (GSH), mouse liver
microsomes and cytosol transform 14C-hexachloro-
1,3-butadiene (HCBD) to S-
(pentachlorobutadienyl)glutathione (PCBG). PCBG
formation in subcellular fractions from a mouse kidney
is very limited. After an oral dose of HCBD to mice,
PCBG in feces, and S-(pentachlorobutadienyl)-L-
cysteine, N-acetyl-S-(pentachlorobutadienyl)-L-
cysteine, and 1,1,2,3-tetrachlorobutenoic acid in the
urine are identified as the metabolites.
storage
Color Code- Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, well-venti lated area away from oxidizers. Where possible, auto-matically pump liquid from drums or other storage contain-ers to process containers A regulated, marked area shouldbe established w here hex achlorobutadiene is handled, used,or stored. A regulated, marked area should be establi shedwhere this chemical is handled, used, or stored in compli-ance with OSHA Standard 1910. 1045.
Purification Methods
Wash the diene with four or five 1/10th volumes of MeOH (or until the yellow colour has been extracted), then stir it for 2hours with H2SO4, wash it with distilled water until neutral and filter it through a column of P2O5. Distil it under reduced pressure through a packed column. [Rytner & Bauer J Am Chem Soc 82 298 1960, Beilstein 1 IV 998.]
Toxicity evaluation
Hexachlorobutadiene specifically damages the pars recta portion
of the proximal tubule with loss of the brush border. The
mechanism involves nonoxidative formation of the glutathione
conjugate in liver with subsequent transport to the kidney for
mercapturic acid conjugate excretion. The resulting cysteine
conjugates are substrates for cysteine-conjugate b-lyase, which
removes ammonia and pyruvate from the cysteine conjugate to
produce thionylacyl halides and thioketenes. These toxic thiol
compounds can then bind covalently to proteins and DNA in
proximal tubular cells to produce nephrotoxicity. S-(1,2,3,4,4-
Pentachloro-1,3-butadienyl)-L-cysteine has been identified as the
ultimate metabolite responsible for hexachlorobutadieneinduced
nephrotoxicity. Mitochondrial dysfunction is reported
to be the ultimate subcellular toxic lesion. Enterohepatic
recirculation of hexachlorobutadiene–glutathione conjugates is
believed to play a major role in this mechanism, since cannulation
of the bile duct of rats prevents nephrotoxicity.
