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.

Antibacterial Agents from Waste Grease: Arylation of Brown Grease Fatty Acids with Beechwood Creosote and Derivatization

“…Our solvent-free arylation of BG with BC required only ferrierite zeolite as an affordable and reusable heterogeneous catalyst that can be simply recovered by filtration. We have demonstrated the catalytic role, reactivity, and regeneration of this catalyst by calcination for its repeated reuse in the past. ,, The resulting crude mixture from the arylation step (step I, Scheme ) was therefore filtered to retrieve the catalyst and then fed to a WFE to separate its components from one another including unreacted BC, any remaining FFAs, and BG fatty acids branched with BC’s natural monophenols (BCBG, Scheme ). In order to push the arylation toward completion, we used an excess ratio of BC to BG FFAs (2.5:1 w/w), and later retrieved the unreacted BC from the WFE’s cold trap.…”

“…To optimize and fine-tune our HPLC method, we analyzed a known mixture of various FFAs and derivatives of phenol-branched soybean fatty acids. 22 Phenol-branched soybean fatty acids and their derivatives only have phenol, instead of a mixture of phenolics present in BC, and hence are inherently less sophisticated than BCBG. Our newly developed HPLC method efficiently separated FFAs from one another (Figures S13 and S14) and enabled monitoring of the phenol-branched soybean fatty acids conversion to their ME and EDA-carrying derivatives (Figure 4).…”

“…We also discussed possible energyefficient alternatives for scale-up methods. Based on our former studies 22,44,45 and ongoing research, these antibacterial agents can copolymerize with epoxy resins.…”

“…Mankind has struggled with pathogenic bacteria since its dawn and has constantly sought new tools throughout history for the prevention of infections, diseases, suffering, and mortality. In order to combat pathogenic bacteria, we have demonstrated the branching of fatty acids with phenolic compounds 22 that results in the emergence of antibacterial properties. 23 Our research group recently branched safflower and soybean oil-derived fatty acids 24 with monophenols including phenol, thymol, carvacrol, and creosote, and correlated their biocidal activity and chemical composition.…”

Synthesis and Anti‐Listeria Properties of Odorless Hybrid Bio‐Based n‐Phenolic Vegetable Branched‐Chain Fatty Acids

“…Due to the complex nature of these arylated isomerized products, a battery of previously described analytical tests was necessary to determine the identity and quantity of the individual components. All synthesized compounds tested in the present study were characterized previously (Ngo et al, ; Yan et al, ). To characterize the compounds, a small amount of each crude arylation product, distillate, and residue was hydrogenated, methylated, and analyzed using gas chromatography with flame ionization detection (GC/FID) on an Agilent 7890B system equipped with a capillary inlet injector (Agilent, Wilmington, DE, USA).…”