The following methods of preparing monochlorohydrin are described
in the literature: action on glycerol of gaseous hydrogen
chloride;[1] action of gaseous hydrogen chloride on glycerol
mixed with an equal volume of acetic acid;[2] action of aqueous
hydrochloric acid on glycerol[3] alone or with an organic acid
(1-2 per cent), such as acetic, as a catalyst;[4] gaseous hydrogen
chloride with an organic acid, as acetic, as a catalyst;[1b] gaseous
hydrogen chloride with the ester of an organic or inorganic acid
as a catalyst;[2b] the action of sulfur monochloride on glycerol.[3b]
[1] Ann. 88, 311 (1853); Ann. chim. phys. (3) 41, 297
(1834); V. R. P. 254,709; 269,657; Frdl. 11, 31 (1912).
[2] Ann. chim. phys. (3) 60, 18 (1860).
[3] D. R. P. 180,668; Frdl. 8, 27 (1907); J. Am. Chem. Soc. 42, 2096
(1920).
[4] D. R. P. 197,309; Frdl. 9, 34 (1908).
[1b] D. R. P. 197,308; Frdl. 9, 33 (1908).
[2b] D. R. P. Anm. 23,510; 16,579; Frdl. 9, 36 (1908).
[3b] D. R. P. 201,230; Frdl. 9, 35 (1908).
X