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Syntes av betulinderivat och deras applikation som mjukgörare för PVC
KTH, School of Chemical Science and Engineering (CHE).
2015 (Swedish)Independent thesis Advanced level (degree of Master (Two Years)), 20 credits / 30 HE creditsStudent thesisAlternative title
Synthesis of Betulin Derivatives and their Application as Plasticizers for PVC (English)
Abstract [en]

Betulin is an easily extractable substance that is found in high concentrations in the bark of birch trees. As bark is a by-product that is generated in thousands of tonnes every year in pulp and paper mills, it would be of both economic and environmental gain to utilize its possible extractives. Betulin has currently found application as an additive in skin care products, but is as of yet not considered a large scale industrial resource.

In this project betulin was used as a starting material to synthesize mono- and di-substituted betulin derivatives via esterification of the hydroxyl groups with propionyl chloride, isopropionyl chloride, 2- chloropropionyl chloride, 3-chloropropionyl chloride, nonanoyl chloride, palmitoyl chloride, trimethyl acetyl chloride and methacrylic anhydride. The structures of the products were confirmed with FT-IR and 1H-NMR. The products’ potential as plasticizers for poly (vinyl chloride) (PVC) was evaluated theoretically with the Hansen Solubility Parameter and practically via solvent casting with PVC and determination of the glass transition temperature with differential scanning calorimetry (DSC). It was found that most of the derivatives appeared to be soluble in PVC at 10-30wt% but appeared to induce only minor effects on the thermal properties when compared to pure PVC films.

Abstract [sv]

Betulin är en substans som lätt kan extraheras från björknäver i förhållandevis höga koncentrationer. Eftersom bark är en biprodukt som varje år genereras i tusentals ton av pappers- och massaindustrin skulle det vara både ekonomiskt och miljömässigt lönsamt att finna användningsområden för dess extraktivämnen. Betulin används för närvarande främst inom kosmetika och som tillsatsämne i hudkrämer, men anses ännu inte vara en storskalig industriell resurs.

I detta projekt användes betulin som startmaterial för att syntetisera mono- och di-substituerade betulinderivat via esterifiering av hydroxylgrupperna med: propionylklorid, isopropionylklorid, 2-kloropropionylklorid, 3-kloropropionylklorid, palmitoylklorid, trimetyl-acetylklorid samt metakrylanhydrid. Strukturerna av de slutgiltiga produkterna bekräftades med FT-IR och 1H-NMR. Produkternas potential som mjukgörare till polyvinylklorid uppskattades teoretiskt med Hansens löslighetsparametrar och praktiskt via lösningsmedelsgjutning med polyvinylklorid samt framtagande av glasomvandlingstemperaturen med hjälp av differentiell svepkalorimetri (DSC). Resultaten visade på att de flesta derivat var lösliga i polyvinylklorid vid 10-30 viktprocent, men deras påverkan på plastfilmernas termiska egenskaper var liten.

Place, publisher, year, edition, pages
2015. , 58 p.
Keyword [en]
Betulin, plasticizers, PVC, esterification, birch bark
National Category
Other Chemistry Topics
Identifiers
URN: urn:nbn:se:kth:diva-172406OAI: oai:DiVA.org:kth-172406DiVA: diva2:847695
Available from: 2015-08-21 Created: 2015-08-21 Last updated: 2015-08-21Bibliographically approved

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