Dimethyl carbonate was evaluated as a green methylating and transesterification reagent and solvent for the chemical-valorisation of renewable platform chemicals from lignin model compounds using a range of catalysts. Of the major components of lignocellulosic biomass (namely cellulose, hemicellulose, and lignin), chemical technologies for the conversion of lignin into higher value-added compounds are the least studied.[1] With a view to developing new chemical products from lignin, it is desirable to first study lignin model compounds. Thus, cinnamyl alcohol, 3-(4-hydroxypropyl)phenol, vanillyl alcohol, and syringic acid were chosen as representative of the p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol building blocks of lignin. Moreover, dimethyl carbonate was chosen because it is cheap, readily available, and has low toxicity, making it a good alternative to traditional methylating agents such as dimethyl sulfate and methyl halides.[2] In the present work, a range of catalysts, including K2CO3, CsF/αAl2O3, NaX, NaY and [P8881][CH3OCOO], are investigated for the methylation and transesterification of the model compounds. One approach is to form the methyl carbonate product in a first step, followed by the methylation reaction in a second step. References [1] J. Zakzeski, P. C. A. Bruijnincx, A. L. Jongerius, B. M. Weckhuysen, Chem. Rev. (Washington, DC, U. S.) 2010, 110, 3552-3599. [2] M. Selva, A. Perosa, Green Chem. 2008, 10, 457-464.
Dimethyl carbonate as a green solvent for the synthesis of platform chemicals from renewable lignin feedstocks
SELVA, Maurizio;PEROSA, Alvise
2012-01-01
Abstract
Dimethyl carbonate was evaluated as a green methylating and transesterification reagent and solvent for the chemical-valorisation of renewable platform chemicals from lignin model compounds using a range of catalysts. Of the major components of lignocellulosic biomass (namely cellulose, hemicellulose, and lignin), chemical technologies for the conversion of lignin into higher value-added compounds are the least studied.[1] With a view to developing new chemical products from lignin, it is desirable to first study lignin model compounds. Thus, cinnamyl alcohol, 3-(4-hydroxypropyl)phenol, vanillyl alcohol, and syringic acid were chosen as representative of the p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol building blocks of lignin. Moreover, dimethyl carbonate was chosen because it is cheap, readily available, and has low toxicity, making it a good alternative to traditional methylating agents such as dimethyl sulfate and methyl halides.[2] In the present work, a range of catalysts, including K2CO3, CsF/αAl2O3, NaX, NaY and [P8881][CH3OCOO], are investigated for the methylation and transesterification of the model compounds. One approach is to form the methyl carbonate product in a first step, followed by the methylation reaction in a second step. References [1] J. Zakzeski, P. C. A. Bruijnincx, A. L. Jongerius, B. M. Weckhuysen, Chem. Rev. (Washington, DC, U. S.) 2010, 110, 3552-3599. [2] M. Selva, A. Perosa, Green Chem. 2008, 10, 457-464.
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