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Preparation of alkyl 11‐anilino‐10‐hydroxy undecanoates and evaluation of their antioxidant activity
Author(s) -
Geethanjali Gorla,
Padmaja Korlipara V.,
Sreedhar Bojja,
Prasad Rachapudi Badari N.
Publication year - 2013
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201200392
Subject(s) - butylated hydroxytoluene , chemistry , antioxidant , differential scanning calorimetry , alkyl , organic chemistry , nuclear chemistry , polymer chemistry , physics , thermodynamics
A novel class of 10‐undecenoic acid‐based alkyl 11‐anilino‐10‐hydroxy undecanoates were prepared by reacting n ‐alkyl (C 1 and C 4 ) and iso alkyl (C 3 , C 4 , and C 8 ) epoxy undecanoates with aniline under catalyst‐free reaction conditions. The synthesized products were characterized by 1 H NMR, IR, GC, and GC‐MS and evaluated for their antioxidant activity using rancimat and differential scanning calorimetry (DSC) methods. The effect of antioxidants was studied at 0.25 and 0. 5% concentrations using rancimat method and at 0.5% in DSC analysis by adding in a lubricant base stock, namely epoxy karanja fatty acid 2‐ethylhexyl esters. All the products exhibited good antioxidant properties at 0.25% concentration and enhanced antioxidant activity with the increased antioxidant concentration at 0.5%. The results obtained from isothermal DSC correlated well with those based on the rancimat method. n ‐Butyl 11‐anilino‐10‐hydroxy undecanoate (4c) exhibited the best stabilizing effect on lubricant base stock with longest induction time compared to butylated hydroxytoluene (BHT) and other products. The data indicate that the synthesized products are potential antioxidants for lubricant formulations.