Radiation-Initiated Side-Chain Chlorination of Toluene. Kinetic Investigations

Yang, John Y.; Thomas, C.C.; Cullinan, Harry T.

doi:10.1021/i260034a009

Ind. Eng. Chem. Proc. Des. Dev.

1970

DOI: 10.1021/i260034a009

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Radiation-Initiated Side-Chain Chlorination of Toluene. Kinetic Investigations

John Y. Yang¹,

C.C. Thomas²,

Harry T. Cullinan³

Abstract: Research supported by the Division of Isotopes Development, U.S. Atomic Energy Commission, under contract AT(30-l)-3864.

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Cited by 9 publications

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Benzyl Chloride, Benzal Chloride, and Benzotrichloride

Lin

Bieron

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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When toluene reacts with chlorine under experimental conditions that promote free‐radical chlorination, a mixture of benzyl chloride, benzal chloride, and benzotrichloride is obtained. The product distribution is determined in large part by the chlorine:toluene ratio. Competing reactions result in chlorination of the aromatic ring, reducing the yield of side‐chain chlorination products. Benzyl chloride undergoes reactions typical of a reactive alkyl halide. Hydrolysis gives benzyl alcohol, reaction with ammonia yields benzylamines, and benzyl esters form by reaction with salts of carboxylic acids. Reaction with other nucleophiles yield substitution products; alkoxides give benzyl ethers and cyanide give phenylacetonitrile. Benzal chloride is hydrolyzed to benzaldehyde and benzotrichloride to benzoic acid. Benzotrifluoride is formed by the reaction of benzotrichloride with anhydrous hydrogen fluoride. Reaction conditions have been determined for aromatic ring chlorination and nitration of benzyl chloride, benzal chloride, and benzotrichloride. More than two‐thirds of benzyl chloride produced is used to make the plasticizer benzyl butyl phthalate. Nearly all of the benzal chloride produced is consumed in the manufacture of benzaldehyde. Benzotrichloride is used in the manufacture of benzoyl chloride and in the synthesis of the herbicide intermediate p ‐chlorobenzotrifluoride.

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Benzyl Chloride, Benzal Chloride, and Benzotrichloride

Lin

Bieron

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Benzyl Chloride, Benzal Chloride, and Benzotrichloride

Seper

2001

Kirk-Othmer Encyclopedia of Chemical Technology

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Chlorinated Hydrocarbons

Rossberg

Lendle

Pfleiderer

et al. 2006

Ullmann's Encyclopedia of Industrial Chemistry

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Radiation-Initiated Side-Chain Chlorination of Toluene. Kinetic Investigations

Abstract: Research supported by the Division of Isotopes Development, U.S. Atomic Energy Commission, under contract AT(30-l)-3864.

Cited by 9 publications

References 4 publications

Benzyl Chloride, Benzal Chloride, and Benzotrichloride

Benzyl Chloride, Benzal Chloride, and Benzotrichloride

Benzyl Chloride, Benzal Chloride, and Benzotrichloride

Chlorinated Hydrocarbons

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