Addition of aromatic compounds to oleic acid catalyzed by heterogeneous acid catalysts

Abstract

The addition of aromatic compounds to the double bond of oleic acid was studied using solid acid catalysts. For example, in the presence of an acid clay catalyst (bentonite), phenol reacted with oleic acid to yield 96% of an alkylphenol addition product. When toluene was used as the aromatic reactant, however, the yield of alkylbenzene addition product was less than 2%. In this instance, the major reactions observed were elaidinization and migration of the double bond of oleic acid. The addition of phenol to oleic acid in greater than 95% yield also was accomplished with the use of a sulfonic acid ion-exchange resin catalyst. This same catalyst also catalyzed the addition of toluene and benzene to oleic acid to yield 82% and 22%, respectively, of alkylbenzene-type addition products. In the latter instances, the major side product formed was 3,-stearolactone. Capillary gas chromatographic (GC) analyses of the alkylbenzene addition products obtained showed them to be mixtures of positional isomers. The isomer distributions were subsequently determined by GC-mass spectrometry (MS).

Catalytic synthesis and characterization of phenol‐branched‐chain fatty acid isomers*

“…Roe et al reported the first example of heterogeneously catalyzed branching of ulc‐FA by condensing a phenolic compound and oleic acid (OLA) with an ion‐exchange resin, leading to an approximately 30% yield of phenyl‐branched‐fatty acid which were reported to have antioxidant properties. Kohashi and Foglia reported the addition of aromatic compounds to fatty acid double bonds by heterogeneous acid clay catalysts to give aryl‐branched‐chain fatty acids (abc‐FAs). In 1995, Alink reported the catalytic arylation of OLA with aromatic hydrocarbons (i.e.…”

Synthesis of Novel Biolubricants from Waste Cooking Oil and Cyclic Oxygenates through an Integrated Catalytic Process

“…In addition to FC acylation products, the C23-ester in P17 (peak 11 in Figure S18 and Table S18) was expected to be formed via esterification of oleic acid and CPL according to reaction : Phenolic alkylation of fatty acid methyl esters on CC bond has been studied by Maglinao et al in a two-step process, including a first HDO step to eliminate the hydroxyl group of phenol and a second alkylation of benzene or toluene. However, the presence of aromatic–alkylated species (such as peak 7 in Figure S14 and Table S14) in this work is ascribed to FC alkylation reaction with anisole, that has been reported to occur over both homogeneous and heterogeneous acid catalysts. , In addition, the C14 and C16 aromatic alkylated fatty acids (peaks 5 and 9 in Figure S14 and Table S14) could have formed from the reaction of P12 anhydrides with anisole.…”

“…However, the presence of aromatic−alkylated species (such as peak 7 in Figure S14 and Table S14) in this work is ascribed to FC alkylation reaction with anisole, that has been reported to occur over both homogeneous and heterogeneous acid catalysts. 48,49 In addition, the C14 and C16 aromatic alkylated fatty acids (peaks 5 and 9 in Figure S14 and Table S14) could have formed from the reaction of P12 anhydrides with anisole. In P17, some unreacted oleic acid and anhydride were identified (peaks 5 and 8, respectively, in Figure S18 and Table S18).…”

Phenolated Oleic Acid Based Polybenzoxazine Derivatives as Corrosion Protection Layers

“…[21] Alkylation of phenols with oleic acid and its esters, including triglycerides,h as been performed using various acid catalysts ranging from ion-exchanger esinst os uperacids such as trifluoromethanesulfonic acid. [22][23][24] Addition of phenol to the oleic acid double bond yields alkylphenols (i.e. hydroxyphenylstearic acids) and phenyle thers (i.e.…”