Bio-based monomers are a more sustainable alternative to conventional oil-based monomers [1]. The bis-epoxide limonene dioxide from the epoxidation of the terpene limonene has shown potential for different applications [2]. One of those applications is the use of limonene dioxide as a crosslinking agent to improve the solvent resistance of nanofiltration membranes. Epoxidation of terpenes is conventionally done using meta-chloroperoxybenzoic acid (m-CPBA), using metal complexes with metals such as Tungsten, Titanium, and Cobalt, or different hydroperoxides. A greener method of epoxidation explored is the use of in situ generated dimethyldioxirane from the reaction of acetone and potassium peroxy-monosulfate (Oxone) [3]. The reaction uses sodium bicarbonate buffer in aqueous solution with a mixture of limonene and acetone. This project aims to synthesize different bis-, and tris-epoxides from different bio-derived terpenes including limonene, gamma-terpinene, geraniol, farnesol, and nerol using the reported method using Oxone and ultrasonication. Epoxidation using m-CPBA is also investigated to compare it to the Oxone method. In general, epoxidation using m-CPBA results in higher amount of epoxide, but the Oxone method presents a more sustainable alternative with good results. Successfully synthesized epoxides are used to crosslink polybenzimidazole nanofiltration membranes. Solvent testing in dimethylacetamide is used to inspect whether crosslinking is successful. Polyethylene glycol diglycidyl ether is a commercial bis-epoxide that was used to validate the crosslinking method. Crosslinking was successful, as confirmed by solvent testing and FT-IR analysis. Filtration testing showed that the permeance of the membrane was not affected by crosslinking, while the membrane’s rejection was increased from 10.29 ± 1.01 % to 17.23 ± 2.49 % after crosslinking using polyethylene glycol diglycidyl ether. Nerol and limonene bis-epoxides were successfully synthesized with high purity and were tested as crosslinkers. However, crosslinking was unsuccessful, as demonstrated by solvent testing. This project successfully synthesized bis-epoxides from different terpenes using a greener method of epoxidation. The possibility of successful crosslinking using the terpene-based crosslinkers should be further investigated.
| Identifer | oai:union.ndltd.org:kaust.edu.sa/oai:repository.kaust.edu.sa:10754/691452 |
| Date | 04 1900 |
| Creators | Albahrani, Shaden |
| Contributors | Szekely, Gyorgy, Physical Science and Engineering (PSE) Division, Nunes, Suzana Pereira, Sarathy, Mani |
| Source Sets | King Abdullah University of Science and Technology |
| Language | English |
| Detected Language | English |
| Type | Thesis |
| Rights | 2024-05-04, At the time of archiving, the student author of this thesis opted to temporarily restrict access to it. The full text of this thesis will become available to the public after the expiration of the embargo on 2024-05-04. |
| Relation | N/A |
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