Oxalyl chloride

• Oxalyl
• Oxalyl

Colorless liquid with a pungent odor

Liquid

1.48 g · cm -3 ( 20 ° C)

-12 ° C.

63-64 ° C

200 hPa ( 20 ° C)

• Decomposition in water
• Soluble in diethyl ether, chloroform and benzene

1.434 ( 13 ° C)

Risk

-367.6 KJ · mol -1

Template: Infobox chemical / molecular formula search available

Oxalyl chloride is a chemical compound with the formula ( COCl ) 2 It is an extremely aggressive and pungent smelling chemical. It is the dichloride of oxalic acid, from which there is also prepared. The colorless liquid is obtainable from a water-free oxalic acid and phosphorus pentachloride.

On 15 March 2000 an Airbus 330 of Malaysia Airlines suffered a total loss, as from wrongly declared canisters oxalyl licked. Five airport employees suffered transhipment of cargo poisoning.

Properties

Oxalyl chloride is a colorless, fuming in moist air due to hydrolysis of liquid. It is highly volatile, but on evaporation / vaporization often leaving a residue of hydrolyzed oxalic acid, which is produced by the reaction with atmospheric moisture.

Use

In the Swern oxidation, a selective method for the production of aldehydes from primary alcohols, of oxalyl chloride is used to activate the oxidant DMSO. It is used to prepare from the corresponding alcohols and acids sensitive chloroalkanes or acid chlorides. Despite the lower reactivity as compared with other halogenating agents it is used due to the better selectivity.

Also, it is required to prepare oxalic acid esters, are not directly accessible from oxalic acid, for example, for the Phenyloxalate Peroxychemolumineszenz.