Thesis (M.Sc.)--Chulalongkorn University, 2005

Twenty one 2-alkylated hydroquinones (H1-H21) and four 2-alkylated-1,4-benzoquinones (Q1-Q4) were synthesized, characterized and explored for their antioxidant activity in lubricant. Among those synthesized compounds, nine hydroquinones (H3, H6-H8, H11-H13, H16 and H20) and a benzoquinones (Q3) were disclosed to be new compounds. The preliminary antioxidant activity results by DPPH radical scavenging assay pointed out that all synthesized hydroquinones exhibited high activity against scavenging DPPH radicals. Three new hydroquinones (H6, H7 and H12) showed the highest activity toward DPPH and exhibited better activity than TBHQ, a commercial antioxidant, possibly due to the formation of more stable phenoxyl radicals. On the contrary, synthesized benzoquinones had no activity. In Rotating Bomb Oxidation Test, three potent aforementioned compounds displayed antioxidant activity more than TBHQ observing from the longer period (IP value) for delaying autoxidation of base oils. The autoxidation inhibition of these compounds can occur in heterogeneous system and is not influenced by solubility confirmed by comparable IP values between H9 and its analogues bearing a lauryl group (L2).