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Detection and Identification of Lignosulfonate Depolymerization Products Using UPLC-QTOF-MS and a Self-Built Database

  • Peng Cui
  • Hong-Xia FangEmail author
  • Chen Qian
  • Man-Huan Cheng
Original

Abstract

In this study, based on depolymerization solution of commercially available sodium lignosulfonate under mild conditions, an efficient method for the chromatographic separation of lignosulfonate depolymerization products was firstly established. The self-built database contains 18 lignin-based standards and the information on their names, formulas, structures, retention times, fragments, and corresponding MSE data was developed. By searching the online spectral data in a novel informatics database, a total of nine aromatic lignin depolymerization products were identified automatically. Thus, a fast standard protocol for detection and identification of real lignin degradation products was preliminary built.

Keywords

Lignosulfonate Identification Aromatics UPLC-QTOF-MS Informatics database 

Notes

Funding

This study was funded by Natural Science Foundation of Anhui Higher Education Institutions of China: KJHS2019B14; KJ2019A0613; KJHS2017B14; KJHS2017B03; KJHS2015B15.

Compliance with Ethical standards

Conflict of Interest

The authors declare that they have no conflict of interest.

Supplementary material

10337_2019_3821_MOESM1_ESM.pdf (391 kb)
Supplementary material 1 (PDF 390 kb)

References

  1. 1.
    Rahimi A, Ulbrich A, Coon JJ, Stahl SS (2014) Formic-acid-induced depolymerization of oxidized lignin to aromatics. Nature 515:249–252CrossRefGoogle Scholar
  2. 2.
    Li C, Zhao X, Wang A, Huber GW, Zhang T (2015) Catalytic transformation of lignin for the production of chemicals and fuels. Chem Rev 115:11559–11624CrossRefGoogle Scholar
  3. 3.
    Chio C, Sain M, Qin W (2019) Lignin utilization: a review of lignin depolymerization from various aspects. Renew Sust Energ Rev 107:232–249CrossRefGoogle Scholar
  4. 4.
    Gillet S, Aguedo M, Petitjean L (2017) Lignin transformations for high value applications: towards targeted modifications using green chemistry. Green Chem 19:4200–4233CrossRefGoogle Scholar
  5. 5.
    Singh SK, Dhepe PL (2016) Ionic liquids catalyzed lignin liquefaction: mechanistic studies using TPO-MS, FT-IR, RAMAN and 1D, 2D-HSQC/NOSEY NMR. Green Chem 18:4098–4108CrossRefGoogle Scholar
  6. 6.
    Wang W, Wang M, Huang J, Zhao X, Su Y, Wang Y, Li X (2019) Formate-assisted analytical pyrolysis of kraft lignin to phenols. Bioresour Technol 278:464–467CrossRefGoogle Scholar
  7. 7.
    Toledano A, Serrano L, Labidi J (2012) Organosolv lignin depolymerization with different base catalysts. J Chem Technol Biotechnol 87:1593–1599CrossRefGoogle Scholar
  8. 8.
    Jia S, Cox BJ, Guo X, ZhangZC Ekerdt JG (2010) Cleaving the β-O-4 bonds of lignin model compounds in an acidic ionic liquid, 1-H-3-methylimidazolium chloride: an optional strategy for the degradation of lignin. Chemsuschem 3:1078–1084CrossRefGoogle Scholar
  9. 9.
    Xu J, Jiang J, Hse C, Shupe TF (2012) Renewable chemical feedstocks from integrated liquefaction processing of lignocellulosic materials using microwave energy. Green Chem 14:2821–2830CrossRefGoogle Scholar
  10. 10.
    Neumann GT, Hicks JC (2012) Novel hierarchical cerium-incorporated MFI zeolite catalysts for the catalytic fast pyrolysis of lignocellulosic biomass. ACS Catal 2:642–646CrossRefGoogle Scholar
  11. 11.
    Barta K, Warner GR, Beach ES, Anastas PT (2014) Depolymerization of organosolv lignin to aromatic compounds over Cu-doped porous metal oxides. Green Chem 16:191–196CrossRefGoogle Scholar
  12. 12.
    Song Q, Wang F, Cai J, Wang Y, Zhang J, Yu W, Xu J (2013) Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation-hydrogenolysis process. Energy Environ Sci 6:994–1007CrossRefGoogle Scholar
  13. 13.
    Lange H, Decina S, Crestini C (2013) Oxidative upgrade of lignin-Recent routes reviewed. Eur Polym J 49:1151–1173CrossRefGoogle Scholar
  14. 14.
    Azarpira A, Ralph J, Lu FC (2014) Catalytic alkaline oxidation of lignin and its model compounds: a pathway to aromatic biochemicals. Bioenergy Res 7:78–86CrossRefGoogle Scholar
  15. 15.
    Fang H, Cui P, Qian C, Liu J, Liu T, Li D, Hu X (2018) Products separation and analysis of depolymerized lignosulfonate under mild acid-catalyzed conditions. Nat Prod Res Dev 30:176–1781Google Scholar
  16. 16.
    Qian Ch, Fang HX, Cui P, Cai F, Gao XY, He HL, Hu XP (2019) Rapid determination of lignosulfonate depolymerization products by advanced polymer chromatography. J Sep Sci 42:2289–2297CrossRefGoogle Scholar
  17. 17.
    Shuai L, Sitison J, Sadula S, Ding J, Thies MC, Saha B (2018) Selective C-C bond cleavage of methylene-linked lignin models and kraft lignin. ACS Catal 8:6507–6512CrossRefGoogle Scholar
  18. 18.
    Rinesch T, Bolm C (2018) Cobalt-catalyzed oxidation of the β-O-4 bond in lignin and lignin model compounds. ACS Omega 3:8386–8392CrossRefGoogle Scholar
  19. 19.
    Zhang FX, Li M, Qiao LR, Yao ZH, Li C, Shen XY, Wang Y, Yu K, Yao XS, Dai Y (2016) Rapid characterization of Ziziphi Spinosae Semen by UPLC/Qtof MS with novel informatics platform and its application in evaluation of two seeds from Ziziphus species. J Pharm Biomed Anal 122:59–80CrossRefGoogle Scholar
  20. 20.
    Fang M, Ivanisevic J, Benton HP, Johnson CH, Patti GJ, Hoang LT, Uritboonthai W, Kurczy ME, Siuzdak G (2015) Thermal degradation of small molecules: a global metabolomic investigation. Anal Chem 87:10935–10941CrossRefGoogle Scholar
  21. 21.
    Hao X, Li T, Zhao L, Wang Y, Yang M, Yin J, Liu J (2019) Chemical ingredients identified from the white SAP of metaplexis japonica using UPLC-QTOF/MS. Chem Nat Compd 55:164–168CrossRefGoogle Scholar
  22. 22.
    Boes KS, Roberts MS, Vinueza NR (2018) Rapid quadrupole-time-of-flight mass spectrometry method quantifies oxygen-rich lignin compound in complex mixtures. J Am Soc Mass Spectrom 29:535–542CrossRefGoogle Scholar
  23. 23.
    Zheng W, Wang F, Zhao Y, SunX Kang L, Fan Z, Qiao L, Yan R, Liu S, Ma B (2017) Rapid characterization of constituents in Tribulus terrestris from different habitats by UHPLC/Q-TOF MS. J Am Soc Mass Spectrom 28:2302–2318CrossRefGoogle Scholar
  24. 24.
    Qiao Y, Chen G, Ma C, Tao B, Ma H, Zhang X, Liu F (2019) Identification of photoproducts of florasulam in water using UPLC-QTOF-MS. Environ Sci Pollut Res 26:7132–7142CrossRefGoogle Scholar
  25. 25.
    Dabral S, Wotruba H, Hernández JG, Bolm C (2018) A mechanochemicaloxidation and cleavage of lignin β-O-4 model compounds and lignin. ACS Sustain Chem Eng 6:3242–3254CrossRefGoogle Scholar
  26. 26.
    ChavanBB Kalariya PD, Srinivas R, Talluri MK (2018) Alcaftadine: selective separation and characterization of degradation products by LC–QTOF–MS/MS. Chromatographia 81:631–638CrossRefGoogle Scholar
  27. 27.
    Deng L, Shi AM, Liu HZ, Meruva N, Liu L, Hu H, Yang Y, Huang C, Li P, Wang Q (2016) Identification of chemical ingredients of peanut stems and leaves extracts using UPLC-QTOF-MS coupled with novel informatics UNIFI platform. J Mass Spectrom 51:1157–1167CrossRefGoogle Scholar
  28. 28.
    Peng-Peng L, Guo-Shun S, Zhang F, Chen JN, Tian-Zhu J (2018) Metabolomics analysis and rapid identification of changes in chemical ingredients in crude and processed Astragali Radix by UPLC-QTOF-MS combined with novel informatics UNIFI platform. Chin J Nat Med 16:714–720Google Scholar
  29. 29.
    Zhang Y, Sun S, Xing X, Du Z, Guo Q, Yu W (2016) Detection and identification of leachables in vaccine from plastic packaging materials using UPLC-QTOF MS with self-built polymer additives library. Anal Chem 88:6749–6757CrossRefGoogle Scholar
  30. 30.
    Frolov A, Henning A, Böttcher C, Tissier A, Strack D (2012) An UPLC-MS/MS method for the simultaneous identification and quantitation of cell wall phenolics in Brassica napus seeds. J Agric Food Chem 61:1219–1227CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Applied Chemistry Laboratory of Huangshan UniversityHuangshanChina
  2. 2.Analysis and Test Center of Huangshan UniversityHuangshanChina

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