Skip to main content
SpringerLink
Log in

Desulfurization of kraft lignin

  • Original
  • Published:
Wood Science and Technology Aims and scope Submit manuscript

Abstract

Kraft lignin is a product of the sulfate pulping process. It usually contains 2–3% total sulfur. Sulfur content acts as deterrent to lignin use in some areas. Sulfur-free lignins are more versatile and can be heat-treated without the release of foul-smelling sulfur compounds. These lignins are used to produce various low- and high-molecular products, as well as fuel. The existing soft desulfurization methods of kraft lignin allow reducing the total sulfur content, for example, fivefold by a method combining extraction of elemental sulfur, oxidation and reduction in sulfur compounds. Deeper desulfurization has earlier been achieved by catalytic hydrogenation, which is accompanied by depolymerization of lignin. In this paper, it was established that sequential treatment of sulfate lignin with benzene, silver in dimethylformamide, aqueous sodium sulfite solution and perchloric acid + acetic anhydride mixture can reduce the total sulfur content a hundredfold.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  • ASTM D4294–16e1 (2016) Standard test method for sulfur in petroleum and petroleum products by energy dispersive X-ray fluorescence spectrometry. ASTM International, West Conshohocken

    Google Scholar 

  • Azarov VI, Burov AV, Obolenskaya AV (1999) Wood chemistry and chemistry of synthetic polymers. Kirov’ Saint Petersburg State Forest Technical Academy, Saint Petersburg, pp 478–481 (in Russian)

    Google Scholar 

  • Bogomolov BD, Gorbunova OF (1974) On the nature of sulphur in the sulphate lignins. In: Kalniņš AI (ed) Chemistry and utilization of lignin. Zinātne, Riga, pp 284–288 (in Russian)

    Google Scholar 

  • Bogomolov BD, Sapotnitskiy SA, Sokolov OM, Sokolova AA, Filippov BS, Mariev AA, Tiranov PP, Tretyakov SI, Novozhilov EV, Gelfand ED, Selyanina LI, Borisov GV (1989) Processing of the sulphate and sulphite spent liquors. Lesnaya Prom-st, Moscow, pp 35–56 (in Russian)

    Google Scholar 

  • Calvo-Flores FG, Dobado JA, Isac-Garcia J, Martin-Martinez FJ (2015) Lignin and lignans as renewable raw materials: chemistry, technology and applications. Wiley, Chichester

    Book  Google Scholar 

  • Chakar FS, Ragauskas AJ (2004) Review of current and future softwood kraft lignin process chemistry. Ind Crops Prod 20(2):131–141

    Article  CAS  Google Scholar 

  • Ekman KH (1966) Retention by lignins of sulphur from sulphate liquors. Pap Puu 48(9):574–578

    Google Scholar 

  • Enkvist T, Rinaman TE (1963) The existence of thiolignins. Pap Puu 45(11):649–656

    CAS  Google Scholar 

  • Evdokimov AN, Kurzin AV, Popova LM, Trifonova AD, Vikhman TM (2014) Desulfurization of tall oil rosin. J Am Oil Chem Soc 91(12):2155–2157

    Article  CAS  Google Scholar 

  • Evdokimov AN, Popova LM, Kurzin AV, Trifonova AD, Buisman G (2017a) Method for purification of rosin. US Pat 9,828,526 B2

  • Evdokimov AN, Kurzin AV, Trifonova AD, Popova LM, Buisman GJH (2017b) Desulfurization of black liquor soap for production of crude tall oil with lower sulfur content. Wood Sci Technol 51(6):1353–1363

    Article  CAS  Google Scholar 

  • Fang Z, Smith RL Jr (2016) Production of biofuels and chemicals from lignin. Biofuels and biorefineries. Springer, Singapore

    Book  Google Scholar 

  • Fengel D, Wegener G (1984) Wood: chemistry, ultrastructure, reactions. Walter de Gruyter, Berlin

    Google Scholar 

  • Field L, Drummond PE, Jones EA (1958) The organic chemistry of sulphur in the kraft process. II. Nature of the sulphur linkages in pine thiolignin. Tappi J 41(12):727–733

    CAS  Google Scholar 

  • Gierer J (1970) The reactions of lignin during pulping: a description and comparison of conventional pulping processes. Svensk Papperstidn 73(18):571–596

    CAS  Google Scholar 

  • Gierer J (1980) Chemical aspects of kraft pulping. Wood Sci Technol 14(4):241–266

    Article  CAS  Google Scholar 

  • Gierer J (1985) Chemistry of delignification. Part 1: general concept and reactions during pulping. Wood Sci Technol 19(4):289–312. https://doi.org/10.1007/BF00350807

    Article  CAS  Google Scholar 

  • Gierer J, Alfredsson B (1957) Über die Reaktionen des Lignins bei der Sulfatkochung. Der Einbau des Schwefels in das Lignin (The reactions of lignin during sulphate pulping process. An appending of the sulphur into the lignin). Acta Chem Scand 11(9):1516–1529 (in German)

    Article  CAS  Google Scholar 

  • Glasser WG, Northey RA, Schultz TP (1999) Lignin: historical, biological, and materials perspectives. ACS Symp Ser 742:1–559

    Google Scholar 

  • Gorbunova OF (1969) The investigation of nature of the sulfur in alkaline-sulphate lignins in the pulping process. Ph.D. Dissertation, Institute of Wood Chemistry, The Academy of Sciences of the Latvian SSR, Riga (in Russian)

  • Hu Z, Du X, Liu J, Chang H, Jameel H (2016) Structural characterization of pine kraft lignin: BioChoice lignin vs Indulin AT. J Wood Chem Technol 36(6):432–446

    Article  CAS  Google Scholar 

  • Huang S (2014) Reductive depolymerization of kraft lignin for chemicals and fuels using formic acid as a in situ hydrogen source. M.Sc. Eng Thesis, University of Western Ontario, Ontario

  • Kawakami H, Takata M (1977) Inorganic sulfur in kraft lignin and their influence on bacterial decomposition of lignin models. Kami Pa Gikyoshi (Jpn Tappi J) 31(3):173–180. https://doi.org/10.2524/jtappij.31.3_173 (in Japanese)

    Article  CAS  Google Scholar 

  • Kazakov VG, Lukanin PV, Fedorova OV, Samoilenko DE (2016) Improvement of the technology for reprocessing black liquors from kraft pulp production. Russ J Appl Chem 89(5):787–792

    Article  CAS  Google Scholar 

  • Komshilov NF, Letonmäki MN, Pilyugina LG, Kyalina LV, Litvinova VB, Selivanova TA, Maslov VA, Volkov VA (1969) The sulphate black liquor and its utilization. Lesnaya Prom-st, Moscow (in Russian)

    Google Scholar 

  • Kouisni L, Gagné A, Maki K, Holt-Hindle P, Paleologou M (2016) LignoForce system for the recovery of lignin from black liquor: feedstock options, odor profile, and product characterization. ACS Sustain Chem Eng 4(10):5152–5159

    Article  CAS  Google Scholar 

  • Kurzin AV, Evdokimov AN, Trifonova AD (2014) Desulfurization of tall oil pitch. Russ J Appl Chem 87(3):299–302

    Article  CAS  Google Scholar 

  • Loutfi H, Blackwell B, Uloth V (1991) Lignin recovery from kraft black liquor: preliminary process design. Tappi J 74(1):203–210

    CAS  Google Scholar 

  • Meyer B (1976) Elemental sulfur. Chem Rev 76(3):367–388

    Article  CAS  Google Scholar 

  • Molinari V, Clavel G, Graglia M, Antonietti M, Esposito D (2016) Mild continuous hydrogenolysis of kraft lignin over titanium nitride–nickel catalyst. ACS Catal 6(3):1663–1670

    Article  CAS  Google Scholar 

  • Nepenin YN (1990) Technology of cellulose, 2nd edn. Volume 2. Production of kraft pulp. Lesnaya Prom-st, Moscow (in Russian)

    Google Scholar 

  • Niemelä K, Tamminen T, Ohra-aho T (2010) Characterisation of black liquor constituents. Analytical techniques for biorefineries. FP0901 Workshop, Wien

  • Oae S (1977) Organic chemistry of sulfur. Plenum Press, New York

    Book  Google Scholar 

  • Oliver AF, Palmer RC (1943) Method of treating tall oil and product obtained thereby. US Pat 2,317,797 A

  • Pollock CM, Miller HJ, Peterson MD (2012) Low sulfur tall oil fatty acid. US Pat 20120131847 A1

  • Radoykova T, Nenkova S, Valchev I (2013) Black liquor lignin products, isolation and characterization. J Chem Technol Metall 48(5):524–529

    CAS  Google Scholar 

  • Sander M (1966) Thiiranes. Chem Rev 66(3):297–339

    Article  Google Scholar 

  • Sanderson TF (1972) Tall oil rosin of low sulfur content. US Pat 3,655,635 A

  • Sarkanen KV, Ludwig CH (1971) Lignins: occurrence, formation, structure and reactions. Wiley, New York

    Google Scholar 

  • Sjöström E (1993) Wood chemistry: fundamentals and applications, 2nd edn. Academic Press Inc, San Diego, pp 114–164

    Book  Google Scholar 

  • Svensson S (2008) Minimizing the sulphur content in kraft lignin. Degree Project, Mälardalens Högskola, Västerås

  • Tomani P, Axegård P, Berglin N, Lovell A, Nordgren D (2011) Integration of lignin removal into a kraft pulp mill and use of lignin as a biofuel. Cellul Chem Technol 45(7–8):533–540

    CAS  Google Scholar 

  • Trifonova AD (2015) Desulfurization of tall oil-derived products of the sulphate pulping process. Ph.D. Dissertation, Saint Petersburg State Technological University of Plant Polymers, Saint Petersburg (in Russian)

  • Tymchyshyn M (2015) Hydrotreatment of lignin into green fuels and chemicals. Ph.D. Thesis, University of Western Ontario, Ontario

  • Vishtal A, Kraslawski A (2011) Challenges in industrial applications of technical lignins. BioResources 6(3):3547–3568. https://doi.org/10.15376/biores.6.3.3547-3568

    Article  Google Scholar 

  • Zhigalov YV, Tishchenko DV (1962) Sulfur in thiolignins. J Appl Chem USSR 35(1):130–135

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Saint Petersburg State University of Industrial Technologies and Design, Higher School of Technology and Energetics (the former Saint Petersburg State Technological University of Plant Polymers), 4, Ivan Chernykh Street, Saint Petersburg, Russian Federation, 198095

    Andrey N. Evdokimov, Alexander V. Kurzin, Olesya V. Fedorova, Pavel V. Lukanin & Vladimir G. Kazakov

  2. GC Alkor Bio, 40a, Zheleznodorozhniy Avenue, Saint Petersburg, Russian Federation, 192148

    Alena D. Trifonova

Authors
  1. Andrey N. Evdokimov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alexander V. Kurzin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Olesya V. Fedorova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Pavel V. Lukanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Vladimir G. Kazakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Alena D. Trifonova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Andrey N. Evdokimov.

Additional information

Publisher's Note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Evdokimov, A.N., Kurzin, A.V., Fedorova, O.V. et al. Desulfurization of kraft lignin. Wood Sci Technol 52, 1165–1174 (2018). https://doi.org/10.1007/s00226-018-1014-1

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00226-018-1014-1

Search

Navigation