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  • 1.
    Areskogh, Dimitri
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Structural Modifications of Lignosulphonates2011Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Lignosulphonates are by‐products from the sulphite pulping process for the manufacture ofspecialty dissolving pulps and paper. During the liberation of the cellulose, the lignin isfractionated and solubilised through covalent addition of sulphonic acid groups at variouspositions in the structure. The formed sulphonated lignin, lignosulphonate is then furtherisolated and refined.

    The amphiphilic nature of lignosulphonates has enabled them to be used as additives to varioussuspensions to improve their dispersion and stability. The by far largest utilisation oflignosulphonates is as dispersants in concrete. Here, lignosulphonates act by dispersing cementparticles to prevent flocculation, un‐even particle distribution and reduced strengthdevelopment. The dispersion is achieved through steric and electrostatic repulsion of the cementparticles by the lignosulphonate polymer. This behaviour is intimately linked with the overallsize and amount of charged groups in the dispersing polymer. Traditional modifications oflignosulphonates have been limited to removal of sugars, filtration and fractionation. Thesemodifications are not sufficient for utilisation of lignosulphonates in high‐strength concrete. Heresynthetic dispersants and superplasticisers are used which are considerably more efficient evenat low dosages. To compete with these, additional modifications of lignosulphonates are likely tobe necessary. The molecular weight and functional group composition have been identified anddescribed as the most interesting parameters that can be modified.

    Currently, no suitable method exists to increase the molecular weight of lignosulphonates.Oxidation by the natural radical initiating enzyme laccase is an interesting tool to achieve suchmodifications. In this thesis several aspects of the mechanism through which this enzyme reactswith lignin and lignosulphonate structures have been elucidated through model compoundstudies. Further studies showed that laccase alone was a highly efficient tool for increasing themolecular weight of commercial lignosulphonates at low dosages and in short incubation times.Immobilisation of the laccase to a solid support to enable re‐utilisation was also investigated.

    Modification of functional group composition of lignosulphonates was achieved throughozonolysis and the Fenton’s reagent, a mixture of hydrogen peroxide and iron(II)acetate.Introduction of charged carboxylic groups was achieved through opening of the benzyl rings oflignosulphonates. It was found that a two‐stage process consisting of laccase oxidation followedby ozonolysis was an efficient technique to create a polymer enriched with carboxylic acidgroups with a sufficient molecular size.

    Oxidation by the Fenton’s reagent was shown to yield similar modifications as the combinedlaccase/ozonolysis treatment albeit with less pronounced results but with a large level of controlthrough variation of a number of reaction parameters. The Fenton’s reagent can therefore be aninteresting alternative to the aforementioned two‐stage treatment.

    These modifications are interesting for large‐scale applications not only because of theirsimplicity in terms of reaction parameters but also because of the ubiquity of the used enzymeand the chemicals in the pulp and paper industry.

  • 2.
    Areskogh, Dimitri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Fenton's reaction: a simple and versatile method to structurally modify commercial lignosulphonates2011In: Nordic Pulp & Paper Research Journal, ISSN 0283-2631, E-ISSN 2000-0669, Vol. 26, no 1, p. 90-98Article in journal (Refereed)
    Abstract [en]

    Treatment of lignosulphonates with hydrogen peroxide and Fe (II) acetate under mild conditions can be used to increase the molecular weight and content of carboxylic acids. Such Fenton's oxidation can produce, in some of the conditions of and lignosulphonate concentration, a two-fold increase in the molecular weight and a 6-7 fold increase in the carboxylic acid content. The structural modifications of lignosulphonate may increase the technical performance of the product in several applications. Possible reaction mechanisms of the Fenton system are proposed and discussed.

  • 3.
    Areskogh, Dimitri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Immobilisation of laccase for polymerisation of commercial lignosulphonates2011In: Process Biochemistry, ISSN 1359-5113, E-ISSN 1873-3298, Vol. 46, no 5, p. 1071-1075Article in journal (Refereed)
    Abstract [en]

    The oxidoreductive enzyme laccase has previously been shown to be able to increase the average molecular weight of lignosulphonatesthrough generation of phenoxy radicals on end groups and the subsequent radical-radical coupling reactions that cross-link individual lignosulphonate molecules. Utilisation of laccases for this purpose is a potential industrial process not only to improve the properties of technical lignosulphonates but also to expand their utilisation to new areas. Immobilisation of the laccase is an interesting technique to enable reusage of the enzyme and thus reduce costs involved with such process. In this work, we demonstrate the potential of immobilised laccase to polymerise technical lignosulphonates. A number of factors that limits re-utilisation of the immobilised catalyst such as lignosulphonate adsorption onto the carrier and laccase deactivation have been identified and are discussed. However, by using a low-porosity support and lower reaction temperatures these problems can be limited.

  • 4.
    Areskogh, Dimitri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Li, Jiebing
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Gellerstedt, Göran
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Investigation of the Molecular Weight Increase of Commercial Lignosulfonates by Laccase Catalysis2010In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 11, no 4, p. 904-910Article in journal (Refereed)
    Abstract [en]

    Lignosulfonates are by-products from the sulfite pulping process. During this process, lignin is liberated from pulp fibers through sulfonation and washed away. As a consequence, the lignosulfonate molecules contain both hydrophobic and hydrophilic moieties. Lignosulfonates are low-value products with limited performance and are used as such as binders, surfactants, and plasticizers in concrete. Lignosulfonates face strong competition from synthetic petroleum-based plasticizers with superior quality. Therefore, increasing the performance of lignosulfonates is desirable not only from a sustainability point of view but also to expand their usage. One important aspect that describes how well lignosulfonates can act as plasticizers is the molecular weight. In this paper, the molecular weight of four commercial lignosulfonates is increased through oxidation by two laccases without utilization of mediators. Different parameters to obtain maximal molecular weight increase were identified and the technical significance of the experiments is discussed.

  • 5.
    Areskogh, Dimitri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Li, Jiebing
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Gellerstedt, Göran
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Polymerization of lignosulohonates by laccase - from model studies to application evaluation trials2010In: Oxidative enzymes as sustainable industrial biocatalysts / [ed] G Feijoo and MT Moreira, 2010, p. 151-156Conference paper (Refereed)
  • 6.
    Areskogh, Dimitri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Li, Jiebing
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Gellerstedt, Göran
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Reaction mechanism of laccase-catalyzed polymerization of lignin revealed with model study2008In: 10th European workshop on lignocellulosics and pulp proceedings, 2008, p. 101-104Conference paper (Refereed)
  • 7.
    Areskogh, Dimitri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Li, Jiebing
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Gellerstedt, Göran
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Structural modification of commercial lignosulphonates through laccase catalysis and ozonolysis2010In: Industrial crops and products (Print), ISSN 0926-6690, E-ISSN 1872-633X, Vol. 32, no 3, p. 458-466Article in journal (Refereed)
    Abstract [en]

    Lignosulphonates are by-products from the sulphite pulping process, in which lignin is separated from cellulose by the addition of sulphonic acid groups to the alpha-position of lignin, thereby increasing the solubility of lignin in water. The predominant industrial utilisations of lignosulphonates are as dispersants, plasticisers and water-reducing agents in concrete preparation. The ability of lignosulphonates to function as a good plasticisers and water reducers is intimately linked with the purity of the lignosulphonate, its molecular weight and the number of charged groups present in the macromolecule. Currently, lignosulphonates are outrivaled by synthetic plasticisers termed superplasticisers due to their superior properties when used as additives to high-strength concrete. If lignosulphonates are to successfully compete with these superplasticisers, significant modifications are required. This paper describes a two-stage treatment of lignosulphonates in which the molecular weight is increased through laccase oxidation and carboxylic groups are introduced through ozonolysis. The technical significance of the results is also discussed.

  • 8.
    Areskogh, Dimitri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Li, Jiebing
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Nousiainen, Paula
    University of Helsinki, Department of Chemistry.
    Gellerstedt, Göran
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Sipilä, Jussi
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Oxidative polymerisation of models for phenolic lignin end-groups by laccase2010In: Holzforschung, ISSN 0018-3830, E-ISSN 1437-434X, Vol. 64, no 1, p. 21-34Article in journal (Refereed)
    Abstract [en]

    The redox enzyme laccase can lead to cross-linking of lignin molecules by oxidising phenolic end groups to resonance-stabilised radicals that can undergo radical coupling to form covalent bonds. This property has potential for many technical applications. However, laccase treatment can also lead to degradation. Experiments were performed with two laccases of different oxidation potential and pH and temperature optima. The predominant reaction following laccase oxidation is the formation of 5-5' and 4-O-5' bonds. If the 5-position is blocked, other reactions occur, including coupling of the 1-position and oxidation of the a-position, which aggravates cross-linking of different lignin molecules. The product profile generated by the two laccases is somewhat different, mainly because of the different pH rather than differences in enzyme activity. Reaction mechanisms and the technical and biological significance of the results are discussed.

  • 9.
    Areskogh, Dimitri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Nousiainen, Paula
    University of Helsinki, Department of Chemistry.
    Li, Jiebing
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Gellerstedt, Göran
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Sipilä, Jussi
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Sulfonation of phenolic end groups in lignin directs laccase-initiated reactions towards cross-linking2010In: Industrial Biotechnology, ISSN 1550-9087, E-ISSN 1931-8421, Vol. 6, no 1, p. 50-59Article in journal (Refereed)
    Abstract [en]

    The effect of sulfonation of the a-carbon on model compounds representing phenolic end groups on lignin was studied with respect to the reactions initiated by oxidation of laccase, by mass spectrometry. Sulfonation seems to direct the reactions towards formation of 5-5´ and 4-O-5´ bonds, avoiding formation of 1-O-4´ bonds and oxidation of the a-carbon. This, in turn, will facilitate cross-linking reactions between lignin molecules. Sulfonation therefore has potential as an industrial pretreatment prior to laccase treatment for various wood-containing materials.

  • 10. Nilsson, H.
    et al.
    Olsson, Ann
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Areskogh, Dimitri
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Iversen, Tommy
    Lipase Catalyzed Co-polymerization of the Suberin Monomercis-9,10-Epoxy-18-hydroxyoctadecanoic Acid with LactonesManuscript (preprint) (Other academic)
  • 11.
    Oinonen, Petri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology. KTH, School of Chemical Science and Engineering (CHE), Centres, Wallenberg Wood Science Center.
    Areskogh, Dimitri
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology. KTH, School of Chemical Science and Engineering (CHE), Centres, Wallenberg Wood Science Center.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology. KTH, School of Chemical Science and Engineering (CHE), Centres, Wallenberg Wood Science Center.
    Enzyme catalyzed cross-linking of spruce galactoglucomannan improves its applicability in barrier films2013In: Carbohydrate Polymers, ISSN 0144-8617, E-ISSN 1879-1344, Vol. 95, no 2, p. 690-696Article in journal (Refereed)
    Abstract [en]

    Hemicelluloses are one of the main constituents of plant cell walls and thereby one of the most abundant biopolymers on earth. They can be obtained as by-products from different wood based processes, most importantly from the mechanical pulping. Hemicelluloses have interesting properties in e.g. barrier film applications. However, their relatively low molecular weight after isolation and co-extraction with lignin has limited their use. In this work, we present a novel technique for increasing the molecular weight of different wood hemicelluloses from mechanical pulping process waters as well as from pre-hydrolysis extracts. This is achieved by enzyme-catalyzed cross-linking of aromatic moieties bound to the hemicelluloses. The cross-linking treatment resulted in significantly improved mechanical properties in barrier films made with spruce galactoglucomannan. To our knowledge, this is the first time that wood hemicelluloses have been cross-linked by utilizing the bound aromatic moieties and creates new possibilities for utilizing this raw material source.

  • 12.
    Oinonen, Petri
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Areskogh, Dimitri
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
    The processing and upgrading of hemicellulose mixtures2011In: Proceedings 16th international symposium on wood, fiber and pulping chemistry, 2011, p. 1028-1031Conference paper (Refereed)
  • 13.
    Zhu, Hongli
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Areskogh, Dimitri
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Helander, Mikaela
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology. KTH, School of Chemical Science and Engineering (CHE), Centres, Wallenberg Wood Science Center.
    A preliminary investigation on enzymatic oxidative polymerization of lignin2011In: 16th International Symposium on Wood, Fiber and Pulping Chemistry: Proceedings, ISWFPC, 2011, p. 238-241Conference paper (Refereed)
    Abstract [en]

    Enzyme catalyzed oxidative polymerization of technical bagasse lignin and low-molecular-weight ultra-filtered kraft pulp lignin (UFL) were studied in methanol-water solution. Lignin was dissolved in methanol-water solution at pH 13 in steam heated autoclave at 130°C for 2h. The polymerization reaction was conducted at 40°C with a commercial laccase under oxygen saturation. The weight-average molecular weight (Mw) of original macromonomer and polymerized lignin were characterized with alkaline size exclusion Chromatograph (SEC) system. Enzyme treatment increased the molecular weight of both technical bagasse lignin and ultra-filtered lignin up to 20 times. The reaction time and the enzyme dosage were studied to obtain the maximal molecular weight.

  • 14.
    Zhu, Hongli
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Areskogh, Dimitri
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Helander, Mikaela
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Investigation on enzymatic oxidative polymerization of technical soda lignin2012In: Abstract of Papers of the American Chemical Society, ISSN 0065-7727, Vol. 243Article in journal (Other academic)
  • 15.
    Zhu, Hongli
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Areskogh, Dimitri
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Helander, Mikaela
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology. KTH, School of Chemical Science and Engineering (CHE), Centres, Wallenberg Wood Science Center.
    Henriksson, Gunnar
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology. KTH, School of Chemical Science and Engineering (CHE), Centres, Wallenberg Wood Science Center.
    Investigation on enzymatic oxidative polymerization of technical soda lignin2012In: Current organic chemistry, ISSN 1385-2728, E-ISSN 1875-5348, Vol. 16, no 16, p. 1850-1854Article in journal (Refereed)
    Abstract [en]

    Enzyme, including laccase and peroxidase, catalyzed oxidative polymerization of technical bagasse soda lignin and low molecular weight ultra-filtrated kraft pulp lignin in methanol-water solution were studied. The weight average molecular weight of original macromonomer and polymerized lignin were characterized with alkaline size exclusion chromatograph system. Laccase treatment increased the molecular weight of both technical bagasse lignin and ultra-filtrated lignin up to 20 times in 24h. Compared to the low molecular weight ultra filtrated lignin, the reaction rate of bagasse lignin was consistant during the whole procedure. The reaction time and the laccase dosage were investigated to obtain the maximal molecular weight. The horseradish peroxidase treatment was a potential method for low molecular weight ultra filtrated lignin.

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