Todays supply of chemical raw materials heavily relies on petroleum based resources whose extraction becomes increasingly difficult due to the progressing depletion of underground deposits. Because of that recent chemical research is intent upon seeking alternative feedstocks to replace petroleum based raw materials and substitute products obtained from these fossil basic materials. Hence green chemistry was developed which deals with avoiding petroleum based raw materials, toxic reagents, unnecessary waist and pollution of the environment. Green chemistry aims at using eco-friendly starting materials, reagents and reactions to contribute to a more sustainable world and to decrease or avoid the proceeding pollution of our environment. The substitution of raw materials gained from fossil resources with sustainable feedstocks is one major principle of green chemistry. Therefore we sought out use wood as a promising renewable resource for chemical raw materials (Xylochemistry). We use small molecules which can be gained from wood (Xylochemicals) as starting materials for the synthesis of natural products and functional chemical materials like colorants and polymers. The sole carbon source for the syntheses of these are xylochemicals.
Applying this concept we synthesized the complex natural products Ilicifoline B starting from ferulic acid, veratrole, methanol and formaldehyde as the xylochemical materials. This preparation represents the first and sole synthesis of this natural product.
Furthermore we developed xylochemical syntheses for indigo dyes and polyamides starting from vanillin and 4-propylcyclohexanol respectively. To further enhance the sustainability of this approach the syntheses were conducted using methods according to the principles of green chemistry.
5,5’,6,6’-Tetramethoxyindigo was prepared from veratrumaldehyde in a straightforward synthesis without using organic solvents.
For the synthesis of the polyamide monomers 4-propylcyclohexanol served as the xylochemical starting material.
These monomers were polymerized by anionic ring opening polymerization (AROP) for the AB-type polyamide and by polycondensation for the A2/B2-type polyamide leading to polymers with unusual properties.
For selected publications on Xylochemistry please see:
Examples of Xylochemistry: Colorants and Polymers
J. Kühlborn, A.-K. Danner, H. Frey, R. Iyer, A. J. Arduengo III, T. Opatz, Green Chem. 2017, 19, 3780–3786.
Xylochemistry - Making Natural Products Entirely from Wood
D. Stubba, G. Lahm, M. Geffe, J. W. Runyon, A. J. Arduengo III, T. Opatz
Angew. Chem. 2015, 127, 14394–14396 (Titelbild).
Angew. Chem. Int. Ed. 2015, 54, 14187–14189 (Cover Picture).
For more information about Xylochemistry please see: