Synthesis of a kairomone and other chemicals from cardanol, a renewable resource

Abstract

Synthesis of a tsetse fly kairomone component (3-propylphenol), a detergent [sodium 2-(dec-8-enyl)-6hydroxybenzenesulfonate], a polymer additive (1-octene), and a detergent precursor [3-(non-8enyl)phenol] using cardanol [3-(pentadec-8-enyl)phenol], has been accomplished. Both carboncarbon double bond isomerization and metathesis methodologies were employed in the syntheses of these target molecules. The kairomone component was obtained, albeit in low yield, in three steps starting with cardanol. Synthesis of a new detergent, sodium 2-(dec-8-enyl)-6-hydroxybenzenesulfonate, was achieved by direct metathesis of cardanol with cis-2-butene followed by sulfonation and basification. Finally, synthesis of 1-octene and 3-(non-8-enyl)phenol was accomplished in one pot by direct metathesis of cardanol with ethylene. These products have been characterized spectroscopically, especially using 1 H and 13 C NMR.

Synthesis of Modified Polycaprolactams Obtained from Renewable Resources

“…This solvent free method needed no plant oil purification, less catalyst and only a distillation as purification step, which made this synthesis very easy and environmentally friendly. Furthermore, Cole‐Hamilton and co‐workers described the metathesis of cardanol with ethylene, wherein 1,4‐cyclohexadiene was also formed as a byproduct . This synthetic method also offers a green alternative to conventionally produced 1,4‐cyclohexadiene.…”

Polymer precursors from catalytic reactions of natural oils

“…Moreover, the catalyst used on monounsaturated cardanol has been shown to be efficient for isomerising the C=C bond to the benzylic position, yielding isocardanol. 144 However, the conversion was only 40%, the remaining products being random isomers of cardanol. Finally, the isomerising olefin metathesis using a bi-catalytic system Ru/Pd was carried out by Goossen and co-workers.…”

Preparation of Musk‐Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination

“…[1][2][3] The most important in this respect are edible and nonedible oils obtained from variousc ultivars and from algae. [1][2][3] The most important in this respect are edible and nonedible oils obtained from variousc ultivars and from algae.…”