Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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

References

    1. Morkhade DM, Nande VS, Barabde UV, Patil AT, Joshi SB. Design and evaluation of dental films of pegylated rosin derivatives containing sparfloxacin for periodontitis. Drug Dev Ind Pharm. 2018;44(6):914–22. doi: 10.1080/03639045.2017.1421660. - DOI - PubMed
    1. Li Z, Yang X, Liu H, Yang X, Shan Y, Xu X, et al. Dual-functional antimicrobial coating based on a quaternary ammonium salt from rosin acid with in vitro and in vivo antimicrobial and antifouling properties. Chem Eng J. 2019;374:564–75. doi: 10.1016/j.cej.2019.05.208. - DOI
    1. Mei L, Yan Y, Li Z, Ran J, Shen L, Wu R, et al. Identification of the diterpenoid biosynthesis genes and their expression status in relation to oleoresin yield of masson pine. Ind Crop Prod. 2021;170:113827. doi: 10.1016/j.indcrop.2021.113827. - DOI
    1. Mantzaridis C, Brocas AL, Llevot A, Cendejas G, Auvergne R, Caillol S, et al. Rosin acid oligomers as precursors of dgeba-free epoxy resins. Green Chem. 2013;15(11):3091–8. doi: 10.1039/c3gc41004h. - DOI
    1. Hamulić D, Stadler M, Hering S, Padrón JM, Bassett R, Rivas F, et al. Synthesis and biological studies of (+)-liquiditerpenoic acid a (abietopinoic acid) and representative analogues: sar studies. J Nat Prod. 2019;82(4):823–31. doi: 10.1021/acs.jnatprod.8b00884. - DOI - PubMed

LinkOut - more resources