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. 2023 Sep 20;17(1):118.
doi: 10.1186/s13065-023-01031-z.

Thermal stability of levopimaric acid and its oxidation products

Yuanlin Li  1 , Hongqin Chen  1 , Heng Yan  1 , Yangyong Xu  1 , Jinwen Tang  1 , Runsen Wang  1 , Mengru Yan  1 , Yuqiao Dai  2 , Yongguang Huang  3 , Xiongmin Liu  4
Affiliations

Thermal stability of levopimaric acid and its oxidation products

Yuanlin Li et al. BMC Chem. .

Abstract

Biofuels are renewable alternatives to fossil fuels. Levopimaric acid‒base biofuels have attracted increasing attention. However, their stability remains a critical issue in practice. Thus, there is a strong impetus to evaluate the thermal stability of levopimaric acid. Through thermogravimetry (TG) and a custom-designed mini closed pressure vessel test (MCPVT) operating under isothermal and stepped temperature conditions, we investigated thermal oxidation characteristics of levopimaric acid under oxygen atmosphere. Thin-layer chromatography (TLC) and iodimetry were used to measure the hydrogen peroxides generated by levopimaric acid oxidation. A high pressure differential scanning calorimeter (HPDSC) was used to assess hydroperoxide thermal decomposition characteristics. Gas chromatography-mass spectrometry (GC-MS) was used to characterize the oxidation products. The thermal decomposition kinetics of levopimaric acid were thus elucidated, and a high peroxide value was detected in the levopimaric acid. The decomposition heat (QDSC) and exothermic onset temperature (Tonset) of hydroperoxides were 338.75 J g-1 and 375.37 K, respectively. Finally, levopimaric acid underwent a second-stage oxidation process at its melt point (423.15 K), resulting in complex oxidation products. Thermal oxidation of levopimaric acid could yield potential thermal hazards, indicating that antioxidants must be added during levopimaric acid application to protect against such hazardous effects.

Keywords: Oxidation characteristics; Peroxide value; Reaction progress; Thermal decomposition; Thermal oxidation.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Scheme 1
Scheme 1
Schematic diagram of the research
Fig. 1
Fig. 1
a The TG curves of levopimaric acid in an oxygen atmosphere b The DTG curves of levopimaric acid in an oxygen atmosphere
Fig. 2
Fig. 2
a Linear fitting plots obtained by the FWO method of thermal decomposition b Ea of levopimaric acid vs. reaction progress with two models
Fig. 3
Fig. 3
Pressure vs. time of levopimaric acid reaction
Fig. 4
Fig. 4
a Peroxide value vs. reaction time; b Peroxide value vs. reaction temperature at 2 h
Fig. 5
Fig. 5
TLC analysis of separated levopimaric acid peroxides
Fig. 6
Fig. 6
Heat flow vs. temperature of Levopimaric acid peroxides by HPDSC
Fig. 7
Fig. 7
Levopimaric acid stepped oxidation a Temperature vs. time; b Pressure vs. time
Scheme 2
Scheme 2
Proposed reaction scheme for levopimaric acid oxidation
See this image and copyright information in PMC

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