Skip to main navigation menu Skip to main content Skip to site footer

Research article

Vol 15 No 2 (2021): Volume 15, Number 2, 2021

Characteristics and kinetics study of glycerolabietate from glycerol and abietic acid from rosin

DOI
https://doi.org/10.22146/jrekpros.69206
Submitted
November 20, 2023
Published
December 31, 2021

Abstract

Rosin is a natural resin from the coniferous tree sap, which separated from its oil content (terpenes). Rosin is brittle. Therefore modifications are needed to improve its mechanical properties. The main content of rosin is abietic acid which has a carboxylic group, so it can form an ester group when reacted with polyhydric alcohol (polyalcohol) such as glycerol. The research aimed to study the kinetics of the esterification reaction between the hydroxyl group in glycerol and the carboxylic group in abietic acid from rosin at various reaction temperatures and reactant compositions. This reaction is carried out in a three-neck flask at atmospheric pressure without a catalyst. The reaction temperatures used were 180˚C, 200˚C, and 220˚C, and the ratio of rosin and glycerol was 1:1, 1:3, and 1:5. The reaction kinetics calculations were analyzed with acid number data over the reaction time using three different models. The calculations showed that this reaction involves positioning a hydroxyl group on glycerol, which the primary and secondary hydroxyl groups contribute to forming a rosin ester (glycerolabietate). The rate of reaction constants of primary hydroxyl of glycerol and abietic acid were in the range 6.25x10-4 - 3.90x10-3 g/(mgeq.min), while reaction rate constants of secondary hydroxyl and abietic acid were in the range 1.06x10-5 - 1.15x10-4 g/(mgeq.min). FTIR analysis showed a change in the hydroxyl, carboxylate, and ester groups which were assigned by a shift of wavenumber and a difference of intensity at 3200-3570 cm-1, 1697.36 cm-1, and 1273.02 cm-1.

References

Bayu, A., Nandiyanto, D., Oktiani, R., & Ragadhita, R. (2019). How to Read and Interpret FTIR Spectroscope of Organic Material. Indonesian Journal of Science & Technology, 4(1), 97–118.

Domene-López, D., Guillén, M. M., Martin-Gullon, I., García-Quesada, J. C., & Montalbán, M. G. (2018). Study of the behavior of biodegradable starch/polyvinyl alcohol/rosin blends. Carbohydrate Polymers, 202, 299–305.

Gandini, A., & Lacerda, T. M. (2015). From Monomers to Polymers from Renewable Resources: Recent Advances. Progress in Polymer Science, 48, 1–39.

García, D. F., Bustamante, F., Villa, A. L., & Alarcón, E. A. (2021). Esterification of rosin with methyl alcohol for fuel applications. Redin (100), 10–20.

Hartanto, D. T., Rochmadi, & Budhijanto. (2020). Mechanism and kinetic model for glycerolysis of shellac. IOP Conference Series: Materials Science and Engineering, 778, 012053.

Hsieh, C. C., & Chen, Y. C. (2020). Synthesis of bio-based polyurethane foam modified with rosin using an environmentally-friendly process. Journal of Cleaner Production, 276, 124203.

Kugler, S., Ossowicz, P., Malarczyk-Matusiak, K., & Wierzbicka, E. (2019). Advances in rosin-based chemicals: The latest recipes, applications and future trends. Molecules, 24(9), 1651. doi:10.3390/molecules24091651.

Kumooka, Y. (2008). Analysis of rosin and modified rosin esters in adhesives by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS). Forensic Science International, 176(2–3), 111–120.

Ladero, M., de Gracia, M., Tamayo, J. J., Ahumada, I. L. de, Trujillo, F., & Garcia-Ochoa, F. (2011). Kinetic modelling of the esterification of rosin and glycerol: Application to industrial operation. Chemical Engineering Journal, 169(1–3), 319–328.

Ladero, M., de Gracia, M., Trujillo, F., & Garcia-Ochoa, F. (2012). Phenomenological kinetic modelling of the esterification of rosin and polyols. Chemical Engineering Journal, 197, 387–397.

Lin, R., Li, H., Long, H., Su, J., & Huang, W. (2014). Synthesis of Rosin Acid Starch Catalyzed by Lipase.

Mumtaz, I., Majeed, Z., Ajab, Z., Ahmad, B., Khurshid, K., & Mubashir, M. (2019). Optimized tuning of rosin adduct with maleic anhydride for smart applications in controlled and targeted delivery of urea for higher plant's uptake and growth efficiency. Industrial Crops and Products, 133(March), 395–408.

Satriana, S., & Supardan, M. D. (2008). Kinetic Study of Esterification of Free Fatty Acid in Low Grade Crude Palm Oil using Sulfuric Acid. ASEAN Journal of Chemical Engineering, 8(1 & 2), 1.

Su, N., Fang, C., Zhou, H., Tang, T., Zhang, S., & Fei, B. (2021). Hydrophobic treatment of bamboo with rosin. Construction and Building Materials, 271. doi:10.1016/j.conbuildmat.2020.121507.

Sun, S., Cheng, X., Ma, M., Liu, Y., Wang, G., Yu, H., Liu, S., et al. (2021). High-efficient esterification of rosin and glycerol catalyzed by novel rare earth Lewis acidic ionic liquid: Reaction development and mechanistic study. Journal of the Taiwan Institute of Chemical Engineers. doi:10.1016/j.jtice.2021.07.026.

Xu, Z., Lou, W., Zhao, G., Zhang, M., Hao, J., & Wang, X. (2019). Pentaerythritol rosin ester as an environmentally friendly multifunctional additive in vegetable

oil-based lubricant. Tribology International, 135(February), 213–218.

Zhou, D., Chen, X., Liang, B., Fan, X., Wei, X., Liang, J., & Wang, L. (2019). Embedding MIL-100(Fe) with magnetically recyclable Fe3O4 nanoparticles for highly efficient esterification of diterpene resin acids and the associated kinetics. Microporous Mesoporous Materials, 289(July). doi:10.1016/j.micromeso.2019.109615.