ChemicalBook CAS DataBase List Triphosgene

Triphosgene synthesis

5synthesis methods

Product Name:Triphosgene
CAS Number:32315-10-9
Molecular formula:C3Cl6O3
Molecular Weight:296.73

Triphosgene is synthesized by exhaustive free radical chlorination of dimethyl carbonate:
CH₃OCO₂CH₃ + 6 Cl₂ → CCl₃OCO₂CCl₃ + 6 HCl
Triphosgene can be easily recrystallized from hot hexanes.

594-42-3 Synthesis

594-42-3
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32315-10-9
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Yield:-

Reaction Conditions:

with sulfur dioxide in dichloromethane;water at 10; for 4 h;

Steps:

12

Example 12To a glass reactor having a central vertical stirrer, a vertical condenser & a dip tube for passing chlorine gas, was charged 730 ml of 3N HC1 in 83.4gm of carbon disulfide, 388gm chlorine gas bubbled over 10 hrs at 24- 25°C. Reaction was terminated when carbon disulfide was < 1%. Trichloromethylsulfenyl chloride, 193 gm was obtained after work up & fractionation.Trichloromethylsulfenyl chloride (193 gm) was added in to a mixture of 500 gm water & 100 ml methylene dichloride, along with 83gm Sulfur dioxide gas at 10°C, over a period of 4 hrs. Reaction was terminated, when trichloromethyl sulfenyl chloride was <1%. Layer separation gave 228 g of thiophosgene which was added to a stirred mixture of 175 gm activated KF, 1 10 gm ortho-chlorobenzyl chloride and 340 gm spherogel (with 2mm diameter), at 60°C, over a period of 3hrs & further maintained at 60°C for 2 hrs gave 98% conversion. ortho-Chlorobenzyl trifluoromethylsulfide (138 gms) was isolated by filtration, followed by distillation, which was added to 500 ml methylene chloride, cooled to 0 to 10°C & 41 gm chlorine gas was bubbled into it, the reaction was maintained for 2 hrs & then heated slowly to 40-45°C. Generated trifluoromethylsulfenyl chloride was passed in to a solution of 5-amino-3-cyano-l-(2,6-dichloro-4- trifluoromethyl phenyl)-pyrazole in methylene dichloride to get 225 g of 5- amino-l-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethyl thiopyrazole.

References:

WO2011/107998,2011,A1 Location in patent:Page/Page column 22-23

616-38-6 Synthesis