Journal
CHEMSUSCHEM
Volume 12, Issue 13, Pages 3103-3114Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201900406
Keywords
acid catalysts; C-1 building blocks; carbamates; renewable resources; zinc
Funding
- Fonds Wetenschappelijk Onderzoek Funding Source: Medline
- VLAIO/Catalisti (ARBOREF) Funding Source: Medline
- Hercules Foundation Funding Source: Medline
- UAntwerpen (IOF, BOF) Funding Source: Medline
- BIO-HArT Funding Source: Medline
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4-Propylcatechol carbonate is a shelf-stable, renewable C1 reactant. It is easily prepared from renewable 4-propylcatechol (derived from wood) and dimethyl carbonate (derived from CO2) using a reactive distillation system. In this work, the 4-propylcatechol carbonate is used for the two-step synthesis of carbamates under mild reaction conditions. In the first step, 4-propylcatechol carbonate is treated with an alcohol at 50-80 degrees C in the presence of a Lewis acid catalyst, such as Zn(OAc)2 center dot 2H(2)O. With liquid alcohols, no solvent is used and with solid alcohols 2-methyltetrahydrofuran is used as solvent. In the second step, the alkyl 2-hydroxy-propylphenyl carbonate intermediates obtained react with amines at room temperature in 2-methyltetrahydrofuran, forming the target carbamates and the byproduct 4-propylcatechol, which can be recycled into a carbonate reactant.
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