Lignin reactions with hypochlorite

HH Nknz and G Turznik. Reactions of Lignin with Singlet Oxygen. I. Oxidation of Monomeric and Dimeric Model Compounds with Sodium Hypochlorite Hydrogen Peroxide. Cell Chem Technol 14 727-742, 1980. 

Conversion of Aromatic Rings to Nonaromatic Cyclic Structures. On treatment with oxidants such as chlorine, hypochlorite anion, chlorine dioxide, oxygen, hydrogen peroxide, and peroxy acids, the aromatic nuclei in lignin typically ate converted to o- and -quinoid stmctures and oxinane derivatives of quinols. Because of thein relatively high reactivity, these stmctures often appear as transient intermediates rather than as end products. Further reactions of the intermediates lead to the formation of catechol, hydroquinone, and mono- and dicarboxyhc acids. 

Commercially, most cellulose is extracted from wood by one of two methods, the kraft (sulfate) process or the steam explosion process. The product of these reactions is wood pulp, which consists primarily of cellulose. In the kraft process, wood chips are treated with a solution of sodium hydroxide (NaOH) and sodium sulfide (Na2S) at temperatures of about 175°C (35o°F) for two to six hours. This process usually results in a yield of about 40 to 45 percent wood pulp. The pulp is then treated with a bleaching agent, such as calcium or sodium hypochlorite (Ca(0Cl)2 or NaCIO) or chlorine dioxide (C102) to remove the color of lignin and other impurities. 

In conventional pulp bleaching, chlorine, hypochlorite, and chlorine dioxide are used with or without intermediate alkaline extraction steps. The first step in conventional lignin-dissolving bleaching is the chlorination. Qilorine water is normally used for this chlorination. It converts the residual lignin to products, that are soluble in water and/or alkali. Chlorine and hypochlorite react primarily with the benzene or phenol rings of lignin, in which substitution and oxidation reactions take place. In a separate extraction step, the unwanted soluble substances are removed with water and/or diluted sodium hydroxide solution. 

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