Applied Catalysis A: General, Vol.543, 173-179, 2017
Palladium-catalyzed hydroamination of farnesene-Long chain amines as building blocks for surfactants based on a renewable feedstock
Long chain amines are of great importance for industrial chemistry as they are precursors for surfactants like amine oxides or quaternary ammonia compounds. The atom efficient, homogeneously catalyzed hydroamination using 1,3-dienes offers linear linkage of the amine group to renewables like beta-famesene, offering a C-15 skeletal structure, which is a desired size for surfactants, the so called laurics. The presented paper describes the development of a catalytic system for the hydroamination of the industrially available terpene beta-famesene in good to excellent yields. The reaction works with a broad range of amines, aliphatic and aromatic ones. Furthermore, functionalities, like alcohol or ether groups, are tolerated, yielding functionalized farnesylamines. With two model nucleophiles, a scale-up to a 5000 mL reactor was accomplished; the obtained products were functionalized to surfactants and afterwards characterized by their surface activity.