Hexachloroacetone

Chemical Properties

clear colorless to yellowish liquid

Uses

Reagent used for the polymerization of vinyl compounds and for the conversion of nucleoside-3′-phosphonates to the corresponding phosphates

Uses

Hexachloro-2-propanone (hexachloroacetone) was used in the synthesis of chirally deuterated benzyl chlorides and enol phosphate 2,2-dichloro-1-(trichloromethyl)ethenyl diethyl phosphate. It was also used in obtaining efficient amino acid activation by exploiting the rapid formation of acid chlorides under low temperature and acid/base free conditions.

Definition

ChEBI: Hexachloroacetone is a ketone.

Production Methods

Hexachloroacetone is produced industrially by catalytic liquid phase chlorination of acetone or partially chlorinated acetone derivatives, a process in which chlorine gas is introduced stepwise to replace all six hydrogen atoms on the acetone molecule. In this method, acetone (or intermediates such as mono , di , or trichloroacetone) is reacted with chlorine in a suitable solvent under controlled temperature and pressure, typically in the presence of catalysts such as activated carbon, pyridine derivatives, or phosphines, which improve reaction efficiency and yield. The reaction proceeds through successive chlorination stages until the fully substituted product, hexachloroacetone, is formed. Industrial setups often use flow reactors operating at elevated temperatures (around 150–160 DegC) and modest pressure to maintain reaction rate and chlorine solubility. After chlorination, the mixture is purified, commonly by distillation or solvent removal, to isolate technical grade hexachloroacetone.

General Description

A yellow-colored liquid. Slightly soluble in water and denser than water. Vapors are much heavier than air. Irritates skin and eyes. May be toxic by ingestion or inhalation. Used to make other chemicals.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

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.

Hazard

Toxic by ingestion and inhalation, strong irritant. Combustible. Evolves phosgene when heated.

Health Hazard

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.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. 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.

Pesticide Type

Herbicide