Reaction of 3‐methyl phenol with tung oil

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Abstract
The aromatic ring substitution reaction of 3‐methyl phenol with tung oil under acidic conditions was carried out. The product was analyzed to find out if 3‐methyl phenol was subjected to the ring substitution reaction with tung oil at its conjugated double bonds. Up to two molecules of 3‐methyl phenol were addition‐reacted with the conjugated triene of one eleostearyl group of triglyceride of α‐eleostearic acid which is the major component of tung oil. The 4‐position of 3‐methyl phenol was preferentially subjected to the cresol's ring substitution. Therefore, up to 6 mol of 3‐methyl phenol was added to 1 mol of tung oil, most of which was bonded to 3‐methyl phenol at its 4‐position. When 3‐methyl phenol was reacted with a relatively large amount of tung oil, the substitution reaction occurred at the 6‐as well as 4‐position of 3‐methyl phenol to yield a tung oil dimer having 3‐methyl phenol units in its molecule. The above results were confirmed by infrared (IR), nuclear magnetic resonance (NMR), and high‐speed liquid chromatographic (HLC) analyses.

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