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ARS Home » Northeast Area » Wyndmoor, Pennsylvania » Eastern Regional Research Center » Sustainable Biofuels and Co-products Research » Research » Publications at this Location » Publication #343729

Research Project: Enable New Marketable, Value-added Coproducts to Improve Biorefining Profitability

Location: Sustainable Biofuels and Co-products Research

Title: Bio-based phenolic-branched-chain fatty acid isomers synthesized from vegetable oils and natural monophenols using modified h+-ferrierite zeolite

item YAN, ZONGCHENG - South China University Of Technology
item Wagner, Karen
item Fan, Xuetong
item Nunez, Alberto
item Moreau, Robert
item Ngo, Helen

Submitted to: Industrial Crops and Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 1/19/2018
Publication Date: 2/16/2018
Citation: Yan, Z., Wagner, K., Fan, X., Nunez, A., Moreau, R.A., Lew, H.N. 2018. Bio-based phenolic-branched-chain fatty acid isomers synthesized from vegetable oils and natural monophenols using modified h+-ferrierite zeolite. Industrial Crops and Products. 114:115-122.

Interpretive Summary: Synthesized antimicrobials (preservatives) are commonly used by the food industry to enhance microbial safety and increase shelf-life. However, food and agricultural industries are experiencing an insufficient selection of nontoxic and potent antimicrobial agents to secure the safety and maintain the quality of food products. Some synthetic preservatives may produce harmful by-products and damage the environment. Therefore, the development of new bioactive and biodegradable materials from vegetable oils would be beneficial to this field. The objective of this study is to develop novel products from vegetable oils with desirable chemical properties to target the bioactive applications. A new class of natural phenolic lipid composed of hydrophobic aliphatic long chains and hydrophilic phenolic regions was successfully prepared and thoroughly purified to result in up to 95% purity. These phenolic lipid products are also odorless which should potentially make them appealing for use as food preservatives.

Technical Abstract: A new group of phenolic branched-chain fatty acids (n-PBC-FA), hybrid molecules of natural monophenols (i.e., thymol, carvacrol and creosote) and mixed fatty acid (i.e., derived from soybean and safflower oils), were efficiently produced through a process known as arylation. The reaction involves a combination of the modified H+-Ferrierite zeolite catalyst and water co-catalyst to give 72.4%, 77.2%, and 48.8% yields thymol-safflower BCFA, creosote-safflower BCFA and carvacrol-BCFA, respectively. The ratio (2.2 to 17 wt/wt) of water co-catalyst to zeolite catalyst were found to have a significant influence to the arylation reaction as the water co-catalyst depressed the isomerization reaction and favored the arylation reaction. The n-PBC-FA products were purified up to >95 wt% by the wiped-film molecular distillation. The modified H+-ferrierite zeolite catalyst can be regenerated by calcining at 500 degree C in air for 2 hours. The activity of the catalyst can be maintained at a relatively stable level without significant deactivation even after 8 reused cycles. The n-PBC-FA products were thoroughly characterized by gas chromatography and high performance liquid chromatography with high-resolution mass spectrometry.