Synthesis of diphosgene

Preparation of diphosgene

Diphosgene is prepared by the action of chlorine on methyl formate and is very related to phosgene.

Preparation of diphosgene

Preparation of diphosgene

The method of chlorination requires a suitable UV source of light (for example mercury vapor lamp). To the flask connected by a ground-glass joint with a condenser containing ice and salt 100 ml of methyl formate are placed. In the beginning of reaction the flask is exposed to a 500-watt lamp, and the current of chlorine is introduced. The flow of chlorine in the beginning of reaction should be maintained at a very low-speed with the temperature is maintained at 30° C. As the reaction proceeded the rate of addition of the chlorine is gradually increased and by this stage the temperature reaches about 90° C. The duration of chlorination process is about 30 hours. Diphosgene obtained is distilled under reduced pressure in an all-glass apparatus provided with a fractionating column and a condenser. The middle fraction, boiling between 50.0-50.4° C at 48 mm of Hg is collected in a receiver containing calcium chloride. Diphosgene is additionally purified by redistillation. Yield of diphosgene is about 70% of theoretical. Diphosgene is colorless liquids it is hydrolyzed by water even at room temperatures and reacts readily with various compounds.

The war gases chemistry and analysis, by M. Sartory, 105, 1939.

IUPAC Name

trichloromethyl carbonochloridate

InChI

InChI=1S/C2Cl4O2/c3-1(7)8-2(4,5)6

InChI Key

HCUYBXPSSCRKRF-UHFFFAOYSA-N

Canonical SMILES

C(=O)(OC(Cl)(Cl)Cl)Cl

MeSH Synonyms

diphosgene, trichloromethyl chloroformate

Depositor-Supplied Synonyms

DIPHOSGENE, Trichloromethyl chloroformate, 503-38-8, trichloromethyl carbonochloridate, Diphosgen, di-Phosgene, Difosgen [Czech], Perchloromethyl formate, Carbonochloridic acid, trichloromethyl ester, HSDB 371, Methanol, trichloro-, chloroformate, EINECS 207-965-9, BRN 0970225, Carbonochloridic acid trichloromethyl ester, Formic acid, chloro-, trichloromethyl ester, Trichlormethylester kyseliny chlormravenci [Czech], Difosgen, Diphosgene; Di-phosgene, trichloromethylchloroformate, tricloromethyl chloroformate, UNII-PO4Q4R80LV, AC1L1V6B, AC1Q3GC7, SCHEMBL4986, trichioromethyl chloroformate, trichloromethyl-chloroformate, PO4Q4R80LV, trichloromethyl chlorocarbonate, 23261_ALDRICH, ACMC-1B029, trichloromethyl chloridocarbonate, 23261_FLUKA, CTK3J0050, HCUYBXPSSCRKRF-UHFFFAOYSA-N, MolPort-003-928-265, BB_SC-6609, AR-1I6140, BBL027815, chloroformic acid trichloromethylester, STL146453, ZINC04261978, AKOS005720866, chloroformic acid trichloromethyl ester, MCULE-6546171284, RTR-031614, Trichlormethylester kyseliny chlormravenci, AN-45386, LS-69680, AB1007691, TR-031614, FT-0659990, 5180-EP2270017A1, 5180-EP2281810A1, 5180-EP2295409A1, 5180-EP2301941A1, 5180-EP2305655A2, 5180-EP2308510A1, 5180-EP2308562A2, 5180-EP2308881A1, 5180-EP2311464A1, 5180-EP2316824A1, 5180-EP2371811A2, 5180-EP2371823A1, 11497-EP2270008A1, 11497-EP2292606A1, 11497-EP2292617A1, 11497-EP2295426A1, 11497-EP2295427A1, 11497-EP2298772A1, 11497-EP2301939A1, 11497-EP2308839A1, 11497-EP2308851A1, 11497-EP2308858A1, 11497-EP2311816A1, 11497-EP2311817A1, 11497-EP2316827A1, 66273-EP2295426A1, 66273-EP2295427A1, 66273-EP2301939A1, 66273-EP2305648A1, 66273-EP2305676A1, 66273-EP2308851A1, 66273-EP2308869A1, 4-03-00-00033 (Beilstein Handbook Reference), 3B4-0483, S14-1192

Removed Synonyms

Superpalite, CID10426, DP, 5203-78-1

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