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Journal of Wood Science

, Volume 64, Issue 6, pp 810–815 | Cite as

Vanillin production from native softwood lignin in the presence of tetrabutylammonium ion

  • Misaki Maeda
  • Takashi Hosoya
  • Koichi Yoshioka
  • Hisashi Miyafuji
  • Hiroyuki Ohno
  • Tatsuhiko Yamada
Original Article
  • 67 Downloads

Abstract

Vanillin is one of the industrially important compounds that can be produced from lignin. This study presents production of vanillin and vanillic acid (oxidized form of vanillin) through aerobic oxidation of Japanese cedar (Cryptomeria japonica) at 120 °C for 72 h in aqueous alkali solutions with several Bu4N+ and OH concentrations (1.25, 2.50, and 3.75 mol/L), where Bu4N+ is an enhancer of the vanillin formation reported in our previous study. The concentrations of Bu4N+ and OH were adjusted by the additions of Bu4NCl and solid NaOH into the base medium Bu4NOH·30H2O, which forms 1.25 mol/L aqueous solution of Bu4NOH at the elevated temperature. Vanillin and vanillic acid were produced with the maximum yields of 21.0 and 1.7 wt% (lignin-base), respectively, at the 1.25 mol/L Bu4N+ and 3.75 mol/L OH concentrations. This vanillin yield is close to that obtained by the alkaline nitrobenzene oxidation (26.5 wt%), indicating significantly high selectivity of our lignin degradation with Bu4N+ toward vanillin formation. We also proposed a novel Bu4NOH·30H2O-free reaction medium, where Bu4NOH·30H2O as the base medium were substituted with an aqueous solution of Bu4NCl and NaOH to avoid using expensive Bu4NOH·30H2O. The treatment of the Japanese cedar with this alternative medium exhibited the moderately decreased vanillin yield of 14.6 wt%, which is, however, much higher than the vanillin yield obtained with a simple 1.25 mol/L NaOH solution.

Keywords

Lignin Aerobic oxidation Vanillin Quaternary ammonium Alkali 

Notes

Acknowledgements

This work was supported by the Technologies for Creating Next-Generation Agriculture, Forestry and Fisheries under the Cross-Ministerial Strategic Innovation Promotion Program (SIP) administered by Council for Science, Technology and Innovation (CSTI), Japan, and a Grant-in-Aid for Young Scientists (B) (No. 17K18008) from the Japan Society for the Promotion of Science.

Supplementary material

10086_2018_1766_MOESM1_ESM.docx (30 kb)
Supplementary material 1 (DOCX 29 KB)

References

  1. 1.
    Brianna MU, Andrea MK (2016) Strategies for the conversion of lignin to high-value polymeric materials: review and perspective. Chem Rev 116:2275–2306CrossRefGoogle Scholar
  2. 2.
    Audrey L, Etienne G, Stéphane C, Stéphane G, Henri C (2016) From lignin-derived aromatic compounds to novel biobased polymers. Macromol Rapid Comm 37:9–28CrossRefGoogle Scholar
  3. 3.
    Francisco G, Dobado AJ (2010) Lignin as renewable raw material. Chem Sus Chem 3:1227–1235CrossRefGoogle Scholar
  4. 4.
    Jiang G, Nowakowski JD, Bridgwater VA (2010) Effect of the temperature on the composition of lignin pyrolysis products. Energy Fuels 24:4470–4475CrossRefGoogle Scholar
  5. 5.
    Kang S, Li X, Fan J, Chang J (2013) Hydrothermal conversion of lignin. Renew Sust Energ Rev 27:546–558CrossRefGoogle Scholar
  6. 6.
    Borges da Silva EA, Zabkova M, Araujo JD, Cateto CA, Barreiro MF, Belgacem MN, Rodrigues AE (2009) An integrated process to produce vanillin and lignin-based polyurethanes from kraft lignin. Chem Eng Res Des 87:1276–1292CrossRefGoogle Scholar
  7. 7.
    Jose DPA, Carlos AG, Alirio ER (2009) Structured packed bubble column reactor for continuous production of vanillin from kraft lignin oxidation. Catal Today 147:330–335CrossRefGoogle Scholar
  8. 8.
    Jose DPA, Carlos AG, Alirio ER (2010) Vanillin production from lignin oxidation in a batch reactor. Chem Eng Res Des 88:1024–1032CrossRefGoogle Scholar
  9. 9.
    Paula CRP, Carina EC, Alirio ER (2013) Oxidation of lignin from eucalyptus globulus pulping liquors to produce syringaldehyde and vanillin. Ind Eng Chem Res 52:4421–4428CrossRefGoogle Scholar
  10. 10.
    Mathias LA, Rodrigues EA (1995) Production of vanillin by oxidation of pine kraft lignins with oxygen. Holzofrsch 49:273–278CrossRefGoogle Scholar
  11. 11.
    Claire F, Alvaro M, Alirio R (1996) Kinetic of vanillin production from kraft lignin oxidation. Ind Eng Chem Res 35:28–36CrossRefGoogle Scholar
  12. 12.
    Guozzhan J, Daniel JN, Anthony VB (2010) Effect of the temperature on the composition of lignin pyrolysis products. Energy Fuels 24:4470–4475CrossRefGoogle Scholar
  13. 13.
    Shimin K, Xianglan L, Juan F, Jie C (2013) Hydrothermal conversion of lignin. Renew Sust Energ Rev 27:546–558CrossRefGoogle Scholar
  14. 14.
    Ogawa S, Miyafuji H (2015) Reaction behavior of milled wood lignin in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 61:285–291CrossRefGoogle Scholar
  15. 15.
    Forss GK, Talka TE, Fremer KE (1986) Isolation of vanillin from alkaline oxidized spent sulfite liquor. Ind Eng Chem Prod Res Dev 25:103–108CrossRefGoogle Scholar
  16. 16.
    Hocking MB (1997) Vanillin: synthetic flavoring from spent sulfite liquor. J Chem Edu 74:1055–1059CrossRefGoogle Scholar
  17. 17.
    Tomlinson G 2nd, Hibbert H (1936) Studies on lignin and related compounds. XXIV. The formation of vanillin from waste sulfite liquor. J Am Chem Soc 58:345–348CrossRefGoogle Scholar
  18. 18.
    Tomlinson G 2nd, Hibbert H (1936) Studies on lignin and related compounds. XXIV. Mechanism of vanillin formation from spruce lignin sulfonic acids in relation to lignin structure. J Am Chem Soc 58:348–353CrossRefGoogle Scholar
  19. 19.
    Triumph Venture Capitals Limited (2004) Part three-Aroma chemicals derived from petrochemical feedstocks. In: Study into the establishment of an aroma and fragrance fine chemicals value chain in South Africa, Triumph Venture Capitals Limited, South AfricaGoogle Scholar
  20. 20.
    Vidal JP (2006) Vanillin. In: Kirk-Othmer encyclopedia of chemical technology. Wiley, Hoboken.  https://doi.org/10.1002/0471238961.2201140905191615.a01.pub2 CrossRefGoogle Scholar
  21. 21.
    Chang HM, Allan GG (1971) Oxidation. In: Sarkanen KV, Ludwig CH (eds) Lignins: occurrence, formation, structure, and reactions. Wiley Interscience, New York, pp 433–485Google Scholar
  22. 22.
    Schultz TP, Templeton MC (1986) Proposed mechanism for the nitrobenzene oxidation of lignin. Holzforsch 40:93–97CrossRefGoogle Scholar
  23. 23.
    Yamamoto K, Hosoya T, Yoshioka K, Miyafuji H, Ohno H, Yamada T (2017) Tetrabutylammonium hydroxide 30-hydrate as novel reaction medium for lignin conversion. ACS Sus Chem Eng 5:10111–10115CrossRefGoogle Scholar
  24. 24.
    Björkman A (1956) Studied on finely divided wood. part1. Extraction of lignin with neutral solvents. Svensk Papperstidn 59:477–485Google Scholar
  25. 25.
    Safdar R, Omar AZ, Ismail LB, Bari A, Lal B (2015) Measurement and correlation of physical properties of aqueous solutions of tetrabutylammonium hydroxide, piperazine and their aqueous blends. Chin J Chem Eng 23:1811–1818CrossRefGoogle Scholar

Copyright information

© The Japan Wood Research Society 2018

Authors and Affiliations

  • Misaki Maeda
    • 1
  • Takashi Hosoya
    • 1
  • Koichi Yoshioka
    • 1
  • Hisashi Miyafuji
    • 1
  • Hiroyuki Ohno
    • 2
  • Tatsuhiko Yamada
    • 3
  1. 1.Graduate School of life and Environmental SciencesKyoto prefectural UniversityKyotoJapan
  2. 2.Graduate School of engineering departmentTokyo University of Agriculture and TechnologyKoganeiJapan
  3. 3.Forestry and Forest Products Research InstituteTsukubaJapan

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