Controlling Product Selectivity in Jojoba Oil Functionalization: Competition Between Alkoxylation and Transesterification Pathway

ABSTRACT

Jojoba oil is a distinctive renewable resource mainly composed of long‐chain wax esters, making it an appealing feedstock for creating high‐value bio‐based materials. In this study, jojoba oil was first epoxidized to activate its double bonds with reactive oxirane groups, then functionalized through acid‐catalyzed alkoxylation using tetrafluoroboric acid, which involves ring‐opening of the epoxide with a nucleophilic alcohol, benzyl alcohol (BnOH). However, alongside the intended alkoxylation, side reactions like transesterification can also occur depending on the experimental conditions. The effects of reaction parameters—catalyst loading, BnOH equivalents, and solvent—were examined to control the product selectivity between transesterification and alkoxylation. A ¹ H NMR study was performed to explore the catalyst's affinity toward different chemical groups in jojoba oil during epoxide ring‐opening. The products were analyzed using ¹ H NMR and Fourier transform infrared (FT‐IR), whereas LC–HRMS helped identify main and side products. A method based on integrating chromatogram peak areas was developed to determine which conditions promote alkoxylation over transesterification. This research enhances understanding of the competitive reactions during jojoba oil functionalization, enabling identification of conditions that favor specific pathways and opening new avenues for using jojoba oil as a bio‐based platform for material development.

Practical Applications : The selective functionalization of jojoba oil provides a practical route to convert a renewable feedstock into tailored bio‐based building blocks for polymer and coating applications. Controlling the balance between alkoxylation and transesterification enables adjustment of the chemical functionality of the resulting products to meet specific material requirements. Alkoxylated jojoba derivatives could serve as reactive components in bio‐based resins, coatings, adhesives, plasticizers, and other polymeric materials. Identifying conditions that favor alkoxylation while limiting undesired transesterification can improve product consistency, reproducibility, and potentially simplify downstream purification. The chromatographic method developed in this study offers a practical tool for rapidly screening reaction conditions and monitoring product selectivity. More broadly, this work demonstrates how the intrinsic chemical structure of jojoba oil can be exploited to produce value‐added renewable chemical building blocks, supporting the development of more sustainable alternatives to fossil‐derived ingredients for high performance polymeric materials.