Skip to main content
Log in

Introducing carboxyl and aldehyde groups to softwood-derived cellulosic fibers by laccase/TEMPO-catalyzed oxidation

  • Original Paper
  • Published:
Cellulose Aims and scope Submit manuscript

Abstract

For more cost-effective and/or value-added utilization of cellulosic fibers in pulp and paper industry, fiber engineering is an important concept. Essentially, fibers can be engineered via various mechanical, chemical, and biological processes. In the current study, the combined use of laccase and TEMPO was applied to introduce carboxyl and aldehyde groups to softwood-derived cellulosic fibers (bleached softwood kraft pulp). The process conditions in preparation of the engineered fibers were optimized. Under the conditions studied, the maximum increases in carboxyl and aldehyde contents were 360 % and 225 %, respectively. The effectiveness of the laccase/TEMPO system could be well explained by the reaction cycles in catalytic oxidation pathways. The findings of the current work may provide useful insights into the enzymatic modification of cellulosic fibers for papermaking applications.

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

Similar content being viewed by others

References

  • Aracri E, Vidal T (2012) Enhancing the effectiveness of a laccase-TEMPO treatment has a biorefining effect on sisal cellulose fibres. Cellulose 19:867–877

    Article  CAS  Google Scholar 

  • Aracri E, Vidal T, Ragauskas AJ (2011a) Wet strength development in sisal cellulose fibers by effect of a laccase-TEMPO treatment. Carbohydr Polym 84:1384–1390

    Article  CAS  Google Scholar 

  • Aracri E, Roncero MB, Vidal T (2011b) Studying the effects of laccase-catalysed grafting of ferulic acid on sisal pulp fibers. Bioresour Technol 102:7555–7560

    Article  CAS  Google Scholar 

  • Aracri E, Valls C, Vidal T (2012) Paper strength improvement by oxidative modification of sisal cellulose fibers with laccase-TEMPO system: influence of the process variables. Carbohydr Polym 88:830–837

    Article  CAS  Google Scholar 

  • Banci L, Ciofi-Baffoni S, Tien M (1999) Lignin and Mn peroxidase-catalyzed oxidation of phenolic lignin oligomers. Biochemistry 38:3205–3210

    Article  CAS  Google Scholar 

  • Baum GA (2002) Fiber engineering: the key to industry change. Solut People Process Pap 85(8):42–45

    Google Scholar 

  • Cantarella G, Galli C, Gentili P (2004) Oxidation of non-phenolic substrates with the laccase/N-hydroxyacetanilide system: structure of the key intermediate from the mediator and mechanistic insight. N J Chem 28:366–372

    Article  CAS  Google Scholar 

  • Cha R, Wang D, He Z, Ni Y (2012) Development of cellulose paper testing strips for quick measurement of glucose using chromogen agent. Carbohydr Polym. 88:1414–1419

    Article  CAS  Google Scholar 

  • Chai X-S, Zhang D, Hou Q, Yoon S-H (2007) Spectrophotometric determination of reducing aldehyde groups in bleached chemical pulps. J Ind Eng Chem 13:597–601

    CAS  Google Scholar 

  • Chivukula M, Renganathan V (1995) Phenolic azo dye oxidation by laccase from Pyricularia oryzae. Appl Environ Microbiol 61:4374–4377

    CAS  Google Scholar 

  • Ding B, Ye Y, Cheng J, Wang K, Luo J, Jiang B (2008) TEMPO-mediated selective oxidation of substituted polysaccharides—an efficient approach for the determination of the degree of substitution at C-6. Carbohydr Res 343:3112–3116

    Article  CAS  Google Scholar 

  • Ding C, Qian X, Yu G, An X (2010) Dopant effect and characterization of polypyrrole-cellulose composites prepared by in situ polymerization process. Cellulose 17:1067–1077

    Article  CAS  Google Scholar 

  • Espy HH (1995) The mechanism of wet-strength development in paper: a review. Tappi J 78(4):90–99

    CAS  Google Scholar 

  • Fabbrini M, Galli C, Gentili P, Macchitella D (2001) An oxidation of alcohols by oxygen with the enzyme laccase and mediation by TEMPO. Tetrahedron Lett 42:7551–7553

    Article  CAS  Google Scholar 

  • Fatehi P, Tutus A, Xiao H (2009) Cationic-modified PVA as a dry strength additive for rice straw pulp. Bioresour Technol 100:749–758

    Article  CAS  Google Scholar 

  • Fatehi P, Liu X, Ni Y, Xiao H (2010) Interaction of cationic modified poly vinyl alcohol with high yield pulp. Cellulose 17:1021–1031

    Article  CAS  Google Scholar 

  • Fornué ED, Allan GG, Quiñones HJC, González GT, Saucedo JT (2011) Fundamental aspects of adhesion between cellulosic surfaces in contact—a review. O Papel 72:85–90

    Google Scholar 

  • Hoshida H, Fujita T, Murata K, Kubo K, Akada R (2005) Copper-dependent production of a Pycnoporus coccineus extracellular laccase in Aspergillus oryzae and Saccharomyces cerevisiae. Biosci Biotechnol Biochem 69:1090–1097

    Article  CAS  Google Scholar 

  • Hou Q, Liu W, Liu Z, Duan B, Bai L (2008) Characteristics of antimicrobial fibers prepared with wood periodate oxycellulose. Carbohydr Polym 74:235–240

    Article  CAS  Google Scholar 

  • Huang B, Kang G, Ni Y (2005) Electrically conductive fiber composites prepared from polypyrrole-engineered pulp fibres. Can J Chem Eng 83:896–903

    Article  CAS  Google Scholar 

  • Hubbe MA, Venditti RA, Rojas OJ (2007) What happens to cellulosic fibers during papermaking and recycling? A review. BioResources 2:739–788

    CAS  Google Scholar 

  • Isogai A, Kato Y (1998) Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation. Cellulose 5:153–164

    Article  CAS  Google Scholar 

  • Laine J (2007) Fibre surface modification by different polyelectrolytes—a possibility to obtain new paper properties. In: PulPaper 2007 conference: innovative and sustainable use of forest resources, Helsinki

  • Larson TM, Anderson AM, Rich JO (2013) Combinatorial evaluation of laccase-mediator system in the oxidation of veratryl alcohol. Biotechnol Lett 35:225–231

    Article  CAS  Google Scholar 

  • Lavazza M, Formantici C, Langella V, Monti D, Pfeiffer U, Galante YM (2011) Oxidation of galactomannan by laccase plus TEMPO yields an elastic gel. J Biotechnol 156:108–116

    Article  CAS  Google Scholar 

  • Marjasvaara A, Torvinen M, Vainiotalo P (2004) Laccase-catalyzed mediated oxidation of benzyl alcohol: the role of TEMPO and formation of products including benzonitrile studied by nanoelectrospray ionization Fourier transform ion cyclotron resonance mass spectrometry. J Mass Spectrom 39:1139–1946

    Article  CAS  Google Scholar 

  • Mathew S, Adlercreutz P (2009) Mediator facilitated, laccase catalysed oxidation of granular potato starch and the physico-chemical characterisation of the oxidized products. Bioresour Technol 100:3576–3584

    Article  CAS  Google Scholar 

  • Mendes P, Sansana P, Silvy J, Costa CAV, Belgacem MN (2001) Cationic starch as a dry strength additive for bleached Eucalyptus globulus kraft pulps. Appita J 54:281–284

    CAS  Google Scholar 

  • Morozova OV, Shumakovich GP, Shleev SV, Yaropolov YI (2007) Laccase-mediator systems and their applications: a review. Appl Biochem Microbiol 43:523–535

    Article  CAS  Google Scholar 

  • Patel I (2010) Studies into the chemoenzymatic modification of cellulose by the laccase/TEMPO system. MSc Thesis of University of Natural Resources and Life Sciences, Vienna

  • Patel I, Ludwig R, Haltrich D, Rosenau T, Potthast A (2011) Studies of the chemoenzymatic modification of cellulosic pulps by the laccase-TEMPO system. Holzforschung 65:475–481

    Article  CAS  Google Scholar 

  • Resalati H (2006) Mixed hardwood CMP pulp reinforcement by wheat straw chemical pulps. In: Proceedings of 2006 TAPPI engineering, pulping and environmental conference, Atlanta, GA, USA

  • Rodgers CJ, Blanford CF, Giddens SR, Skamnioti P, Armstrong FA, Gurr SJ (2010) Designer laccases: a vogue for high-potential fungal enzymes? Trends Biotechnol 28:63–72

    Article  CAS  Google Scholar 

  • Saito T, Isogai A (2004) TEMPO-mediated oxidation of native cellulose. The effect of oxidation conditions on chemical and crystal structures of the water-insoluble fractions. Biomacromolecules 5:1983–1989

    Article  CAS  Google Scholar 

  • Shen J, Song Z, Qian X, Liu W (2009a) Modification of papermaking grade fillers: a brief review. BioResources 4:1190–1209

    CAS  Google Scholar 

  • Shen J, Song Z, Qian X (2009b) Investigations on the preparation of starch/sodium oleate/alum modified precipitated calcium carbonate filler and its use in papermaking. Appita J 62:360–364

    CAS  Google Scholar 

  • Shen J, Song Z, Qian X, Liu W, Yang F (2010a) Filler engineering for papermaking: comparison with fiber engineering and some important research topics. BioResources 5:501–503

    Google Scholar 

  • Shen J, Song Z, Qian X, Yang F (2010b) Carboxymethyl cellulose/alum modified precipitated calcium carbonate fillers: preparation and their use in papermaking. Carbohydr Polym 81:545–553

    Article  CAS  Google Scholar 

  • Talwar KK (1957) A study of improved strength in paper made from low-substituted carboxymethylcellulose pulps. Ph.D Thesis of the Institute of Paper Chemistry. Retrieved Jan 18, 2013. Url:https://smartech.gatech.edu/xmlui/bitstream/handle/1853/5638/talwar_kk.pdf?sequence=1

  • Yano A, Kikuchi S, Nakagawa Y, Sakamoto Y, Sato T (2009) Secretory expression of the non-secretory-type Lentinula edodes laccase by Aspergillus oryzae. Microbiol Res 164:642–649

    Article  CAS  Google Scholar 

  • Zhang DC, Chai XS, Ragauskas AJ (2005) Chemical modification of pulp fibers by selective catalytic oxidation during oxygen delignification. 2005 Engineering, Pulping, and Environmental Conference. Retrieved Jan 10, 2013. Url:http://www.tappi.org/Downloads/unsorted/UNTITLED-05EPE192pdf.aspx

  • Zhang H, Li J, Hu H, He Z, Ni Y (2012) Improvement of bleached wheat straw pulp properties by using aspen high-yield pulp. Bioresour Technol 120:40–44

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Xueren Qian.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Xu, S., Song, Z., Qian, X. et al. Introducing carboxyl and aldehyde groups to softwood-derived cellulosic fibers by laccase/TEMPO-catalyzed oxidation. Cellulose 20, 2371–2378 (2013). https://doi.org/10.1007/s10570-013-9985-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10570-013-9985-4

Keywords

Navigation