Synthesis of functionalized Pararosaniline over mild conditions

VALLEJO ORREGO, ALEJANDRO; GUTIERREZ, LEANDRO G.; FERRETTI, CRISTIÁN A.

Basel

Conferencia; The 25th International Electronic Conference on Synthetic Organic Chemistry; 2021

MDPI

Dyes and pigments have many applications, and their growing development is driven by their increased use. As a contribution to this topic, in this work, the synthesis of functionalized pararosaline was evaluated with the aim to obtain an amphiphilic dye. Pararosaline is a dye highly soluble in water and polar solvents, presenting three amino groups in its structure. We realized that the functionalization of pararosaline by direct coupling of amino groups with halogenated fatty acids leads to amides derived from fatty acid. In the synthesis, fatty acid chloride from sunflower oil and basic catalysts were used. Over a single step one-pot procedure carried out at room temperature in moderate reaction time, a new functionalized pararosaline was synthesized. The results showed that after derivatization with chloride of fatty acids, the dye exhibits solubility both in water and in non-polar systems with different color intensities.