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Polychlorinated naphthalene (PCN) are the products obtained upon treatment of naphthalene with chlorine. The generic chemical formula is C 10 H 8−(m+n) Cl (m+n). Commercial PCNs are mixtures of up to 75 components and byproducts. [1] The material is an oil or a waxy solid, depending on the degree of chlorination.
2-Chloronaphthalene is obtained directly by chlorination of naphthalene, with the formation of more highly substituted derivatives such as dichloro- and trichloronaphthalenes, in addition to the two monochlorinated isomeric compounds: 1-chloronaphthalene and 2-chloronaphthalene. [4]
For example, chlorination and bromination of naphthalene proceeds without a catalyst to give 1-chloronaphthalene and 1-bromonaphthalene, respectively. Likewise, whereas both benzene and naphthalene can be alkylated using Friedel–Crafts reaction conditions, naphthalene can also be easily alkylated by reaction with alkenes or alcohols , using ...
The relative potency of three ring Cl-PAHs was found to increase with increasing degree of chlorination as well as with increasing degree of chlorination. However, the relative potencies of the most toxic Cl-PAHs assessed up to now have been found to be 100,000-fold lower than the relative potency of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). [9]
p-DCB is produced by chlorination of benzene using ferric chloride as a catalyst: . C 6 H 6 + 2 Cl 2 → C 6 H 4 Cl 2 + 2 HCl. The chief impurity is the 1,2 isomer.The compound can be purified by fractional crystallization, taking advantage of its relatively high melting point of 53.5 °C; the isomeric dichlorobenzenes and chlorobenzene melt well below room temperature.
The reaction mechanism for chlorination of benzene is the same as bromination of benzene. Iron(III) bromide and iron(III) chloride become inactivated if they react with water, including moisture in the air. Therefore, they are generated by adding iron filings to bromine or chlorine. Here is the mechanism of this reaction:
The most commonly employed Sandmeyer reactions are the chlorination, bromination, cyanation, and hydroxylation reactions using CuCl, CuBr, CuCN, and Cu 2 O, respectively. More recently, trifluoromethylation of diazonium salts has been developed and is referred to as a 'Sandmeyer-type' reaction.
The reagent removes pairs of H atoms from organic molecules. The stoichiometry of its action is illustrated by the conversion of tetralin to naphthalene: 2 C 6 Cl 2 (CN) 2 O 2 + C 10 H 12 → 2 C 6 Cl 2 (CN) 2 (OH) 2 + C 10 H 8. The resulting hydroquinone is poorly soluble in typical reaction solvents (dioxane, benzene, alkanes), which ...