[5] Ann. 122, 73 (1862); 168, 43 (1873); Ber. 5, 354
(1872); Ann. chim. phys. (6) 22, 437 (1891).



IX

GLYCEROL a-MONOCHLOROHYDRIN

C3H5(OH)3 + HCl--> CH2ClCHOHCH2OH + H2O

Prepared by J. B. CONANT and O. R. QUAYLE. Checked by O. KAMM
and A. O. MATTHEWS.


1. Procedure

FIVE HUNDRED grams of glycerol (90 per cent) and 10 g.
of glacial acetic acid are mixed in a weighed 1-l. flask,
which is placed in an oil bath heated to 105-110'0. A rapid
stream of dry hydrogen chloride is introduced into the mixture.
The flask is removed from the bath from time to time and reweighed.
At the end of about four hours the flask will have gained 190 g.
in weight. The reaction is then complete.

The product is distilled under diminished pressure.
Below 114'0/14 mm., 220-250 g. distil; this portion is mostly water.
The monochlorohydrin is collected between 114-120'0/14 mm.;
it weighs 360 g., which is 66 per cent of the theoretical amount.
About 20 g. more may be obtained by neutralizing the first fraction