#phosphorous pentachloride

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Chlorination with 500 g phosphorous pentachloride. 

PCl5 is a highly toxic, corrosive ect. yellow solid and a pretty well working reagent. When adding it to ethers it could chlorinate the carbon by turning into the also highly toxic, corrosive ect. phosphorous trichloride what could be distilled out from the reaction mixture.

The problem starts when not everything reacted and you want to distill the products. PCl5 sublimes quite easily at 160 °C, so after the distillation you could easily end up with phosphorous pentachloride dissolved in everything.

Note: PCl5 reacts with water violently to form highly toxic phosphorous oxychloride: PCl5 + H2O → POCl3 + 2 HCl What will give ortho-phosphoric acid and hydrochloric acid upon standing in water: O=PCl3 + 3 H2O → O=P(OH)3 + 3 HCl