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Lundquist, K., Parkås, J., Paulsson, M., and Heitner, C. (2007). "Reactions of lignin chromophores of the enal and enone type with sulfite," BioRes. 2(3), 334-350.


In NaHSO3-solutions of coniferaldehyde and its methyl ether (models for lignin chromophores of the cinnamaldehyde type) a dynamic equilibrium between the aldehydes and their hydrogen sulfite adducts is set up. A comparatively slow addition of hydrogen sulfite to the double bond leading to 1,3-disulfonic acid derivatives occurs; coniferaldehyde reacts slower than its methyl ether. In Na2SO3-solution both aldehydes are rapidly converted to 1,3-disulfonic acid derivatives. The results suggest that in both NaHSO3-solution and Na2SO3-solution the free cinnamaldehydes and sulfite ion are the reactants in the formation of disulfonic acid derivatives. Alkaline treatment of the 1,3-disulfonic acids leads to regeneration of the cinnamaldehydes. On prolonged storage in Na2SO3-solution, the 1,3-disulfonic acid derivative of the methyl ether of coniferaldehyde undergoes reactions leading to colored products and regeneration of the cinnamaldehyde on alkaline treatment fails. A model compound representative of lignin chromophores of enone type (trans-3,3’,4,4’-tetramethoxychalcone) rapidly undergoes addition to the double bond with formation of a sulfonic acid derivative in Na2SO3-solution. Treatment of a second model of enone type, 2,6-dimethoxy-p-quinone, with NaHSO3/Na2SO3-solution results in formation of a sulfonic acid derivative. The reactions of lignin chromophores of the enone and enal types with hydrogen sulfite/sulfite are discussed.
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