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ChemicalBook CAS DataBase List VINYL CHLOROFORMATE
5130-24-5

VINYL CHLOROFORMATE synthesis

6synthesis methods
Two processes have been used commercially to make Vinyl Chloroformate. First, ethylene glycol is converted to its bis(chloroformate) with phosgene. This fragments to VOC-Cl in 30- 40% yield when passed through a hot tube packed with glass helices at 480 °C. More recently, VOC-Cl has been made commercially using a two-step route involving the oxymercuration of vinyl acetate.
VINYL CHLOROFORMATE
-

Yield: 85.2%

Reaction Conditions:

palladium diacetate in hexanedinitrile at -2 - 2; for 63 h;Product distribution / selectivity;

Steps:

32
To a 2 L jacketed 3-neck flask fitted with a -2° C. chiller unit, mechanical stirrer with Teflon paddle, graduated dropping funnel with 213.3 grams adiponitrile topped with a dry ice condenser, and a gas outlet, was added 637 grams of adiponitrile, 116 grams (1.0 mole) VOTMS, and 1.7 grams (0.0075 mol) PdAc2. The reagents were stirred for 30 minutes. Next, 112 grams, (1.1 mol) of phosgene was condensed into the dropping funnel with 213.3 grams of adiponitrile. The phosgene was added to the pot over a period of 63 minutes so the temperature was -2° C. to +2° C. The reaction mixture was allowed to stir and after 63 hours the reaction mixture was sparged with dry N2 to remove excess phosgene, filtered to remove catalyst, and tert-butylhydroquinone was added to inhibit polymerization. A total of 1015 grams of 8.94% VCF solution was obtained from the reaction and provided 85.2% yield of VCF.

References:

Bausch & Lomb Incorporated US8273914, 2012, B1 Location in patent:Page/Page column 11; 12

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