Skip to main content
Log in

Fully Automated Determination of Trimellitic Anhydride in Saturated Polyester Resins Using Programmed Temperature Vaporization-Large Volume Injection-Gas Chromatography Previous Aqueous Derivatization with Triethyloxonium Tetrafluoroborate

  • Original
  • Published:
Chromatographia Aims and scope Submit manuscript

Abstract

Trimellitic anhydride (TMAn) is an essential starting material of the chemical manufacturing industry; it is widely used in saturated polyester resins (SPR) manufacturing to produce plasticizers for different purposes. TMAn was recently added, as a new substance of very high concern, to the candidate list by the European Chemicals Agency, since it can lead to sensitization, respiratory tract irritation and lung disease. Any substance from the list of candidates if present in manufactured products at concentrations above 0.1% (w/w) obliges the manufacturer to communicate this to customers down the supply chain and to consumers. We propose here a method that allows the fully automated determination of TMAn in SPR samples by using large volume injection (LVI), with programmed temperature vaporization (PTV) injection, in a gas chromatographic (GC) system equipped with ion trap mass spectrometer (IT) operating in tandem mass spectrometry (MS/MS). The method optimization was obtained by a chemometric model, using the experimental design. Introducing the use of short chromatographic column, triethyloxonium tetrafluoroborate (TEO) as derivatization agent and IS granted specificity, sensitivity and robustness. The detection and quantification limits for TMAn were 0.01% and 0.03% w/w, respectively. Trueness (between 94 and 98%) and precision (RSD lower than 10%, n = 6) were also assessed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Honest Version, Lake Wales, FL, USA. Trimellitic Anhydride market growing at a cagr of 2.1% during 2019–2025. Available at: https://honestversion.com/trimellitic-anhydride-market-growing-at-a-cagr-of-2-1-during-2019-2025/. Accessed 23 Oct 2019

  2. Hexa Research, Felton, California 95018, United States. Trimellitic anhydride market analysis, market size, application analysis, regional outlook, competitive strategies and forecasts, 2016–2024. Available at: https://www.hexaresearch.com/research-report/trimellitic-anhydride-market. Accessed 23 Oct 2019

  3. Ullmann F, Gerhartz W, Yamamoto YS, Campbell FT, Pfefferkorn R, Rounsaville JF (1985) Ullmann’s encyclopedia of industrial chemistry. VCH publishers, Weinheim

    Google Scholar 

  4. MarketsandMarkets™ Research Private Ltd. Tower B5, office 101, Magarpatta SEZ, Hadapsar, Pune-411013, India. Saturated Polyester Resin Market by Type (Liquid SPR and Solid SPR), Application (Powder Coatings, Industrial Paints, Coil & Can Coatings, Automotive Paints, Flexible Packaging, and 2k PU Coatings), and by Region - Global Forecasts to 2021. Available at: https://www.marketsandmarkets.com/Market-Reports/saturated-polyester-resin-market-127811947.html?gclid=Cj0KCQjw1MXpBRDjARIsAHtdN-3xVL7Bh2cG_FY_d42HXW2LlCEPeMkdkC6ffl63S-dbZ9nSr_oSWwgaAkKFEALw_wcB. Accessed 23 Oct 2019

  5. Grand View Research San Francisco, California, United State. Saturated Polyester Resin Market Analysis, Market Size, Application Analysis, Regional Outlook, Competitive Strategies, And Segment Forecasts, 2015–2022.

  6. Patterson R, Zeiss CR, Pruzansky JJ (1982) Immunology and immunopathology of trimellitic anhydride pulmonary reactions. Allergy Clin Immunol 70:19–23

    Article  CAS  Google Scholar 

  7. European Chemicals Agency (ECHA), Annankatu 18, P.O. Box 400, FI-00121 Helsinki, Finland. 10 new substances added to the candidate list. Available at: https://echa.europa.eu/it/-/ten-new-substances-added-to-the-candidate-list. Accessed 26 Oct 2019

  8. Yucui H, Jian L, Shuhang R, Muge N, Weize W (2014) Separation of the isomers of benzene poly(carboxylic acid)s by quaternary ammonium salt via formation of deep eutectic solvents. J Phys Chem B 118:13646–13650

    Article  Google Scholar 

  9. Khaled MY, McNair HM (1996) Capillary zone electrophoretic separation of isomeric benzoic acids using cyclodextrin. J High Resolut Chromatogr 19(3):143–150

    Article  CAS  Google Scholar 

  10. Palassis J, Posner JC, Slick E, Schulte K (1981) Air sampling and analysis of trimellitic anhydride. Am Ind Hyg Assoc J 42(11):785–789

    Article  CAS  Google Scholar 

  11. Rushing LG, Althaus JR, Thompson HC Jr (1982) Simultaneous determination of trimellitic anhydride and its trimellitic acid impurity by GC/FID. J Anal Toxicol 6(6):290–293

    Article  CAS  Google Scholar 

  12. Pfäffli P (1994) Determination of low concentrations of trimellitic anhydride in air. J Chromatogr A 684(2):269–275

    Article  Google Scholar 

  13. Method: OSHA 98; Procedure: high performance liquid chromatography using ultraviolet detector; Analyte: trimellitic anhydride; Matrix: air; Detection Limit: 0.623 ug/cu m. US Department of Labor/Occupational Safety and Health Administration's Index of Sampling and Analytical Methods. Available from: https://www.osha.gov/dts/sltc/methods/toc.html on Trimellitic Anhydride (552–30–7) as of October 3, 2006. Last access 29 Dec 2019

  14. Leardi R (2018) D-optimal designs. Encyclopedia of analytical chemistry. Wiley, Amsterdam, pp 1–11

    Google Scholar 

  15. ICH official web site. Rue de Pre-Bois, 20 PO Box 1894, 1215 Geneva, Switzerland. Quality guidelines. Available at: https://www.ich.org/products/guidelines/quality/article/quality-guidelines.html. Accessed 6 Nov 2019

  16. Guandalini G, Soldani L, Rosi L, Calamai L, Bartolucci G (2015) A methodological approach to the selection of liquid reagents for chemical ionization ion trap-gas chromatography mass spectrometry: a case study of GBL and 1,4-BD. Int J Mass Spectrom 388:34–39

    Article  CAS  Google Scholar 

  17. Tauler R, Walczak B, Brown SD (2009) Comprehensive chemometrics: chemical and biochemical data analysis. Elsevier, New York

    Google Scholar 

  18. Myers RH, Montgomery DC, Anderson-Cook CM (2009) Response surface methodology. Wiley, New York

    Google Scholar 

  19. Liebich HM, Xu G, Di Stefano C, Lehmann R (1998) Capillary electrophoresis of urinary normal and modified nucleosides of cancer patients. J Chromatogr A 793(2):341–347

    Article  CAS  Google Scholar 

  20. Liebich HM, Gesele E, Wöll J (1998) Urinary organic acid screening by solid-phase microextraction of the methyl esters. J Chromatogr B Biomed Sci Appl 713(2):427–432

    Article  CAS  Google Scholar 

  21. Sonntag M, Strohriegl P (2004) Novel 2, 7-linked carbazole trimers as model compounds for conjugated carbazole polymers. Chem Mater 16(23):4736–4742

    Article  CAS  Google Scholar 

  22. Meerwein H, Hinz G, Hofmann P, Kroning E, Pfeil E (1937) Über tertiäre oxoniumsalze, I. J Prakt Chem 147:257

    Article  CAS  Google Scholar 

  23. Ammazzini S, Onor M, Pagliano E, Mester Z, Campanella B, Pitzalis E, Bramanti E, D'Ulivo A (2015) Determination of thiocyanate in saliva by headspace gas chromatography-mass spectrometry, following a single-step aqueous derivatization with triethyloxonium tetrafluoroborate. J Chromatogr A 1400:124–130

    Article  CAS  Google Scholar 

  24. Raber DJ, Gariano P Jr, Brod AO, Gariano A, Guida WC, Guida AR, Herbst MD (1979) Esterification of carboxylic acids with trialkyloxonium salts. J Organ Chem 44(7):1149–1154

    Article  CAS  Google Scholar 

  25. Dugheri S, Bonari A, Pompilio I, Mucci N, Montalti M, Arcangeli G (2016) Development of new gas chromatography/mass spectrometry procedure for the determination of hexahydrophthalic anhydride in unsaturated polyester resins. RASĀYAN J Chem 9(4):657–666

    CAS  Google Scholar 

  26. Staniewski J, Rijks JA (1992) Solvent elimination rate in temperature-programmed injections of large sample volumes in capillary gas chromatography. J Chromatogr A 623(1):105–113

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Stefano Dugheri.

Ethics declarations

Conflict of Interest

The authors declare that they have no conflict of interest.

Ethical Approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 245 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dugheri, S., Marrubini, G., Speltini, A. et al. Fully Automated Determination of Trimellitic Anhydride in Saturated Polyester Resins Using Programmed Temperature Vaporization-Large Volume Injection-Gas Chromatography Previous Aqueous Derivatization with Triethyloxonium Tetrafluoroborate. Chromatographia 83, 601–613 (2020). https://doi.org/10.1007/s10337-020-03877-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10337-020-03877-0

Keywords

Navigation