Synthesis, chemical characterization, and economical feasibility of poly‐phenolic‐branched‐chain fatty acids

Abstract

New poly‐phenolic branched‐chain fatty acid (poly‐PBC‐FA) products were synthesized from a combination of soybean fatty acids and phenolic materials through a highly efficient zeolite catalyzed arylation method. These poly‐PBC‐FAs are liquid at room temperature and do not have the unpleasant odor like the parent phenol reagent. They were found to be comprised of various numbers of phenol rings on the fatty acid chain, and this is important because compounds with a higher number of hydroxyl groups are expected to have better antimicrobial activities. Detailed characterization using gas chromatography and high performance liquid chromatography coupled to a quadrupole‐time of flight mass spectrometer techniques were used to measure the number of phenol groups on the alkyl fatty acid chains. A cost process modeling technique was used to determine the economic feasibility of this arylation process to make these important poly‐PBC‐FA products.Practical applications: The continued outbreaks of Listeria monocytogenes in foods imply that current antimicrobial products are not sufficient to control pathogen contamination. These new phenolic branched‐chain fatty acid products contain hydrophobic and hydrophilic properties. They are found to bear close resemblance to antimicrobial compounds that are receiving a great deal of attention for biomedical and/or materials applications. This finding is highly encouraging because the phenolic products are odorless which should make them appealing for possible food applications to kill the harmful Listeria monocytogenes.New poly‐phenolic branched‐chain fatty acid products were synthesized from a combination of soybean fatty acids and phenol materials through a highly efficient zeolite catalyzed arylation method. These isolated phenolic fatty acid materials are liquid at room temperature and do not have the unpleasant odor like the parent phenol reagent. Mass spectroscopy results confirmed more than one phenol group is on the alkyl chain due to the polyunsaturated fatty acid materials used. The cost model indicated that the process is feasible at the industrial scale.