RING-CHLORINATED TOLUENES

The ring-chlorinated derivatives of toluene form a group of stable, industrially important compounds. Many chlorotoluene isomers can be prepared by direct chlorination. Other chlorotoluenes are prepared by indirect routes involving the replacement of amino, hydroxyl, chlorosulfonyl, and nitro groups by chlorine and the use of substituents, such as nitro, amino, and sulfonic acid, to orient substitution followed by their removal from the ring. 

The first systematic study of the reaction of chlorine with toluene was carried out in 1866 by Bedstein and Geitner. During the next 40 years, many studies were performed to isolate and identify the various chlorination products (1). During the early 1930s, Hooker Electrochemical Co. (Hooker Chemicals Plastics Corp.) and the Heyden Chemical Corp. (Tenneco) began the manufacture of chlorotoluenes. Hooker Electrochemical Co. was later acquired by Occidental Petroleum Corp. and became the Occidental Chemical Corp. In the mid-1970s, Heyden exited chlorotoluenes production Occidental thus is the sole U.S. producer of chlorotoluenes. 

Mono- and dichlorotoluenes ate used chiefly as chemical iatermediates ia the manufacture of pesticides, dyestuffs, pharmaceuticals, and peroxides, and as solvents. Total annual production was limited prior to 1960 but has expanded greatly siace that time. Chlorinated toluenes ate produced ia the United States, Germany, Japan, and Italy. Siace the number of manufacturers is small and much of the production is utilised captively, statistics covering production quantities ate not available. Worldwide annual production of o- and -chlorotoluene is estimated at several tens of thousands of metric tons. Yearly productions of polychlorotoluene ate ia the range of 100—1000 tons. 

Kirk-Othmer Encyclopedia of Chemical Technology (4th Edition) 

The monochlorotoluenes are stable to the action of steam, alkahes, amines, and hydrochloric and phosphoric acids at moderate temperatures and pressures. Three classes of reactions, those involving the aromatic ring, the methyl group, and the chlorine substituent, are known for monochlorotoluenes. 

---

Chlorinated paraffins. Chlorinated ben2enes. Ring-chlorinated toluenes. Benzyl chloride. 

Ring-Chlorinated Toluenes" under "Chlorocarbons, Chlorohydrocarbons" in ECT3rd ed., Vol. 5, pp. 819—827, by S. Gelfand, Hooker Chemical Plastics Corp. 

CHLOROCARBONSANDCHLOROHYDROCARBONS - RING-CHLORINATED TOLUENES] (Vol 6) 2-Chloro-3(p-chlorophenyl)-l,4-benzoqumone [80632-61-7]... 

CHLOROCARBONSANDCHLOROHYDROCARBONS - RING-CHLORINATED TOLUENES] (Vol 6) [CHLOROCARBONSANDCHLOROHYDROCARBONS - RING-CHLORINATED TOLUENES] (Vol 6) [CHLOROCARBONSANDCHLOROHYDROCARBONS - RING-CHLORINATED TOLUENES] (Vol 6) [CHLOROCARBONSANDCHLOROHYDROCARBONS - RING-CHLORINATED TOLUENES] (Vol 6) [CHLOROCARBONSANDCHLOROHYDROCARBONS - RING-CHLORINATEDTOLUENES] (Vol 6)... 

---