Hexachloroacetone

1.444 AT 12 °C/12 °C

1.74 @ 12°C

Slightly sol in water; sol in acetone

MISCIBLE WITH ALIPHATIC HYDROCARBONS, VEGETABLE OILS, 2-PROPANOL AT 25 °C

MISCIBLE WITH METHANOL, AROMATIC HYDROCARBONS, MONOCHLOROBENZENE, ISOPROPANOL AT 25 °C

Sol in benzene

202-204 °C

202.2 °C @760 [mm Hg]

-2 °C

MP: 15 °C /HEXACHLOROACETONE HYDRATE/

-2 °C

-2 °C

0.12 [mmHg]

0.376 MM HG AT 20 °C

0.376 [mm Hg] @20 °C

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

H302 (91.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

2-Propanone, 1,1,1,3,3,3-hexachloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanone, 1,1,1,3,3,3-hexachloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 27-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/17343

Hexachloroacetone: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Highly irritating; Produces phosgene when heated; [Hawley] A skin and mucous membrane irritant; A mild lachrymator; Oral LD50 (rat) = 1550 mg/kg; In animal studies, caused pulmonary edema after inhalation and liver and kidney injury after ingestion; Can cause burns of skin and eyes; [HSDB] Oral TDLo (rat) = 450.8 mg/kg (1-14D preg) for maternal effects (oogenesis); [RTECS] Contact with molten substance may cause severe burns; [CAMEO] An irritant; Effects in high-dose animal studies include pulmonary edema; [MSDSonline]

The major hazards encountered in the use and handling of hexachloroacetone stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal contact), exposure to this musty-smelling liquid may occur from its use as an intermediate in the production of chloroform and hexafluoroacetone. Effects from exposure may include contact burns to the skin and eyes, and irritation of the mucous membranes. If contact should occur, immediately flush affected eyes with running water for at least 15 minutes, and wash skin with soap and water. Remove contaminated clothing and shoes at the site. While hexachloroacetone does not ignite easily, it may burn with the production of irritating and poisonous gases. Also, heating of this substance may give rise to toxic thermal decomposition products such as chlorine or phosgene. Fires involving hexachloroacetone may be extinguished with dry chemical, CO2, Halon, water spray, fog, or standard foam. Hexachloroacetone should be stored in well-ventilated areas, away from heat and sources of ignition. Containers for international shipment by air and by water must bear the labels, "Keep away from food" and "Poison", respectively. Small spills of hexachloroacetone may be taken up with sand or other noncombustible absorbent and placed into containers for later disposal. Before implementing land disposal of waste hexachloroacetone, consult with environmental regulatory agencies for guidance.

HEXACHLOROACETONE is a halogenated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.

For more DOT Emergency Guidelines (Complete) data for HEXACHLOROACETONE (8 total), please visit the HSDB record page.

Hexachloroacetone

UN2661

Div 6.1 Poisonous materials (49 eCFR § 173.132)

PG III: the degree of danger presented by the material is minor

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

General First Aid:

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

0.14 [mg/m3]

3.0 [mg/m3]

18 [mg/m3]

Hexachloroacetone without solvent was mutagenic, and this activity was enhanced when it was dissolved in dimethyl sulfoxide; in acetone it was not mutagenic. A time dependent reaction of hexachloroacetone with dimethyl sulfoxide was the only test material solvent interaction found. Results show clearly that dimethyl sulfoxide is not an appropriate solvent for hexachloroacetone.

TERRESTRIAL FATE: Hexachloroacetone has a vapor pressure of 0.376 mm Hg at 20 °C(2) indicating that the chemical is expected to evaporate significantly from dry surfaces(SRC). The estimated Koc of 1,886(3,SRC) suggests that hexachloroacetone will have low mobility in soil and will not leach(1). No data are available regarding biodegradation or other chemical processes in soil(SRC).

AQUATIC FATE: If released to water, hexachloroacetone is expected to evaporate into the atmosphere with a volatilization half-life of 6.5 hours from a model river(SRC). No data are available on other potential degradation processes in water. Based on the estimated Koc of 1,886(1,SRC), hexachloroacetone may partition from the water column to the sediment.

ATMOSPHERIC FATE: Based on a vapor pressure of 0.376 at 20 °C(1), hexachloroacetone will exist almost entirely in the vapor phase in the ambient atmosphere(2,SRC). Hexachloroacetone will not react with photochemically produced hydroxyl radicals in the ambient atmosphere(3,SRC).

Concentration of hexachloroacetone in chlorination stage effluent from a bleached kraft pulp mill in the interior of British Columbia was approximately 1.1 mg/l. (Fresh sample taken immediately prior to analysis) /From table/

Hexachloroacetone was deteted in pulp mill effluents with a concentration of approximately 30 g hexachloroacetone per ton pulp(1) and a concentration of approximately 0.2 g hexachloroacetone in the spent chlorination liquor per ton pulp(2) after the chlorination process. Hexachloroacetone was found in chlorinated municipal sewage effluents at a concentration of 30 ppb(3).

ANALYSIS OF A SAMPLE OF CHLORINATION STAGE EFFLUENT FROM A BLEACHED KRAFT PULP MILL REVEALED THE PRESENCE OF HEXACHLOROACETONE.

Hexachloroacetone was detected after the chlorination process in pulp mill effluents with a concentration of approximately 30 g hexachloroacetone per ton pulp(1) and a concentration of approximately 0.2 g hexachloroacetone in the spent chlorination liquor per ton pulp(2). Hexachloroacetone was found in chlorinated municipal sewage effluents at a concentration of 30 ppb(3). Hexachloroacetone was once used as a weedkiller, but it is currently believed to be of little commercial interest(4).

Based on an estimated log Kow of 3.49(2) and a recommended regression equation, the water solubility is estimated to be 154.7 mg/L(2,SRC). Based on a vapor pressure of 0.376 mm Hg at 20 °C(1) and a water solubility of 154.7 mg/L(2), the Henry's Law constant is estimated to be 8.33X10-4 atm cu-m/mole at 25 °C(SRC). This value of Henry's Law constant suggests that hexachloroacetone will volatilize significantly, but not rapidly from water. Based on this value, the volatilization half-life of hexachloroacetone from a model river 1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec has been estimated to be approximately 6.5 hours(3,SRC).

... /SRP: SIGNIFICANT/ PERCUTANEOUS TOXICITY IN RABBITS.

Inhalation exposure caused pulmonary edema, hemorrhage & congestion in laboratory rats. Only slight repair of lung tissue was noted in these animals, 15 days after exposure. Chronic feeding studies in rats revealed hypertrophy of liver & kidneys, & slight growth depression.

The oral toxicity of hexachloroacetone in adult male albino rats of the Wistar strain was CNS depression. The dermal toxicity in adult male albino rabbits was mild CNS depression and erythema at exposed area. The inhalation toxicity in adult albino rats was CNS depression manifested as hind leg instability, loss of postural and righting reflexes, and death. Gross exam of the lung immediately after death presented a picture of widespread hemorrhage. Edema, hemorrhage and congestion of the lung was evident microscopically 15 days after termination of exposure, with little indication of repair of the injury.

THE MUTAGENIC PROPERTIES OF HEXACHLOROACETONE IN SHORT TERM BACTERIAL MUTAGEN ASSAY SYSTEMS: HEXACHLOROACETONE REVERTS THE AMES SALMONELLA TYPHIMURIUM STRAINS TA98 & TA100, BUT NOT THE NON-PLASMID STRAINS TA1535, TA1537, & TA1538. IN ABSENCE OF SOLVENT, THE NUMBER OF REVERTANT COLONIES IS 5 TIMES THE SPONTANEOUS REVERSION RATE FOR TA100 & 10 TIMES THE SPONTANEOUS REVERSION RATE FOR TA98 WITH 26 MG HEXACHLOROACETONE/PLATE.

Compounds ... /including/ hexachloroacetone ... identified in pulp mill effluents were screened for genetic activity in growing cells using Saccharomyces cerevisiae strains D7 and XV185-14C without and with S9. Hexachloroacetone without solvent was mutagenic.

Used as reagent for N-trichloroacetylation of dipeptides, to produce chloroform, and formerly as a herbicide and pre-harvest desiccant on alfalfa seed crops; [HSDB]

Farming (Pesticides) [Category: Industry]

Reagent for N-trichloroacetylation of dipeptides under neutral conditions.

Hexafluoroacetone is manufactured by the reaction of hexachloroacetone and hydrogen fluoride in the presence of a chromium catalyst.

Chloroform may be produced from acetone by intermediate production of hexachloroacetone.

Hexachloroacetone was once used as a weedkiller, but it is currently believed to be of little commercial interest.

BY DIRECT CHLORINATION OF ACETONE.

... Chlorination /of isopropyl alcohol/ at 70-100 °C provides nearly complete conversion of lower chloroacetones into 1,1,1,3,3-pentachloroacetone and hexachloroacetone.

20% TECHNICAL IN AROMATIC PETROLEUM OILS, USED 1 PART TO 9 PARTS BY VOLUME OF AROMATIC PETROLEUM OILS, AT RATES OF 50-150 US GALLONS/ACRE.

FORMULATED AS AN EMULSIFIABLE CONCENTRATE, GRANULAR, & WETTABLE POWDER.

TECHNICAL PRODUCT IS ABOUT 85% PURE.

Discontinued mixture: Urox 379, (bromacil + hexachloracetone).

GC 1106

Miscellaneous Manufacturing

2-Propanone, 1,1,1,3,3,3-hexachloro-: ACTIVE

Discontinued by Allied Chemical Corp.