Uses
It can be used for organic synthesis, for example: dyes, saccharin,etc.
General Description
A white to gray powdered solid with a distinctive odor. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. Used to make other chemicals.
Air & Water Reactions
Insoluble in water.
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
Preparation
Tosyl chloride is a by-product from the production of ortho-toluenesulfonyl chloride (a precursor for the synthesis of the common food additive and catalyst saccharin), via the chlorosulfonation of toluene:
CH3C6H5+ SO2Cl2→ CH3C6H4SO2Cl + HCl
Flammability and Explosibility
Nonflammable
Purification Methods
Material that has been standing for a long time contains tosic acid and HCl and has m ca 65-68o. It is purified by dissolving (10g) in the minimum volume of CHCl3 (ca 25mL) filtered, and diluted with five volumes (i.e. 125mL) of pet ether (b 30-60o) to precipitate impurities. The solution is filtered, clarified with charcoal and concentrated to 40mL by evaporation. Further evaporation to a very small volume gives 7g of white crystals which are analytically pure, m 67.5-68.5o. (The insoluble material is largely tosic acid and has m 101-104o.) [Pelletier Chem Ind (London) 1034 1953.] It also crystallises from toluene/pet ether in the cold, from pet ether (b 40-60o) or *benzene. Its solution in diethyl ether has been washed with aqueous 10% NaOH until colourless, then dried (Na2SO4) and crystallised by cooling in powdered Dry-ice. It has also been purified by dissolving in *benzene, washing with aqueous 5% NaOH , then dried with K2CO3 or MgSO4, and distilled under reduced pressure and can be sublimed at high vacuum [Ebel Chem Ber 60 20861927]. [Beilstein 11 IV 375.]
