A study of ketone migration for the synthesis of hydroxy fatty acids from natural plant based oil

• Main Author: Kuek, Eugene Jun Rong
• Other Authors: Tan Choon Hong
• Format: Thesis-Master by Research
• Language: English
• Published: Nanyang Technological University 2025
• Subjects: Chemistry; Oleochemicals; Long chain fatty acids
• Online Access: https://hdl.handle.net/10356/182949
• Institution: Nanyang Technological University

This thesis explores the synthesis of novel lipids from commercially available oleic acid using a ketone migration chemical technique. The primary objective was to modify the structure of oleic acid to create unique lipid derivatives with potentially distinct physical and chemical properties. A key innovation was the development of a straightforward chemical procedure employing elemental sulfur and pyrrolidine for ketone migration, which enabled the modification of long linear alkyl chains and facilitated the synthesis of terminally functionalized long-chain fatty acids with yields up to 10%. In addition to this, the research demonstrated that unsaturated fatty acids can serve as effective starting substrates for synthesizing various positional-hydroxy fatty acids, including 8/9/10/11-hydroxy stearic acid. This method provides an affordable and efficient approach to lipid modification. The thesis also investigated the enzymatic synthesis of fatty acyl hydroxy fatty acid esters using immobilized C.andida Antartica A in a one-step process, exploring their potential as skin moisturizers with initial indications of improved efficacy.