Reaction of 3‐methyl phenol with tung oil

Abstract

SynopsisThe 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 a t 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 a-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 t u g 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.

Identification of an Original Non-Terpenoid Varnish from the Early 20th Century Oil Painting “The White Horse” (1929), by H. Menzel

“…The phenolic resins appear to react with the drying oil to produce what is essentially a copolymer of the oil and resin − and Ziebarth et al. , have reported on the formation of copolymers between the phenolic resins and tung oil. A nuclear substitution reaction can occur between the para or meta positions of the alkylphenol and the tung oil.…”

Resource utilization of Sambucus williamsii Hance root

“…Phenol, 3-methyl-is mainly used as pesticide intermediates in the production of insecticides such as fenthion, methomyl and pyrethroid-like isophenoxybenzaldehyde. It is also used in analytical reagents, organic synthesis, color film, resin plasticizer, perfume, medicine, antioxidants and other industries requiring the use of m-cresol in chemical industry [35,36] [37][38][39]. The functions of some other substances need to be further developed and studied.…”

Kinetics of reactions of methyl α‐eleostearate with cresols

“…with phenols in the presence of an acid catalyst. [20][21][22] In these latter studies, we found out a number of things, including that the conjugated triene of an a-eleostearate group (constituting the backbone of tung oil) is addition reacted with a phenol on its ring, the conjugated triene of one a-eleostearate group is addition reacted with a maximum of two molecules of phenols, and the addition reaction occurs preferentially at the para position of the phenols. However, in implementing an investigation from the standpoint of kinetics, there is a difficulty in analyzing the reaction due to the large molecular weight of T.O.…”