Behaviour of Residual Lignin in Kraft Pulp During Bleaching

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1 25. LI, J. and van HEININGEN, A.R.P., Kinetics dium SulfatePotassium Sulfate Eutectic: Re Thesis, McGill Univ. (1991). of Gasification of Black Liquor Char by actions of Some Sulfur Compounds, Inorg. 28. WYNNYCKYJ, J.R. and RSUKIN, W.J., An Steam, IEC Research 30(7): 1594 (1991). Chem. 22(22):3243 (1983). Intrinsic Transport Model for SolidSolid Re 26. DEARNALEY, R.I., KERRIDGE, D.H. and 27. ZOU, X., Recovery of Kraft Black Liquor actions Involving a Gaseous Intermediate, ROGERS, D.J., Molten Lithium SulfateSo Including Direct Causticization, Ph.D. Metallurgical Trans. B 19B(2):73 (1988). Behaviour of Residual Lignin in Kraft Pulp During Bleaching D. LACHENAL, J.C. FERNANDES and P. FROMENT The behaviour of residual lignin in softwood kraft pulp during bleaching has been investigated. Chlorine, chlorine dioxide, oxygen, hydrogen peroxide and ozone treatments have been carried out on unbleached pulp and the residual lignin has been extracted by enzymatic hydrolysis of the carbohydrates. The main functional groups have been measured by I9F NMR spectroscopy and the molecular weight distribution has been studied. New information on the chemistry of the bleaching agents has been obtained, which explains some of the differences observed in their bleaching effect. For example, chlorine has the capability to depolymerize the residual lignin while forming new free phenolic groups, which makes it without any equivalent among the bleaching agents. On the contrary, ozone does not cleave the residual lignin very efficiently. Consequently, it must be associated with another chemical which has this capability, like oxygen or chlorine dioxide.!ntrod!jction The recent concern [I] about the fate of chlorinated organic compounds downstream from a kraft mill has generated unprecedented research activity in the bleaching area. Although the major objec rs D. Lachenal, J.C. Fernandes and P. Froment Ecole Franqaise de Papeterie B.P Saint Martin d'heres Cedex France tive has been to replace chlorine, hypochlorite and, if necessary, chlorine dioxide by oxygenbased reagents (oxygen, hydrogen peroxide, ozone, peracids), it is of prime importance to have a better understanding of the reasons why the chlorinecontaining chemicals are such efficient bleaching agents. The role of chlorine during bleaching was reexamined recently and a new mechanism has been found to explain its outstanding reactivity on lignin [2]. Chlorine dioxide bleaching has also been under investigation in many places during recent years [361, primarily to try to inhibit the side reactions. Simultaneously, oxygen, peroxide and ozone bleaching chemistry has been the subject of considerable research activity [7 IO]. The merit of these studies has been to explain why chlorinefree bleaching is feasible, where the problems are coming from and how some of them could be solved. However, the understanding is still fragmented and does not give satisfactory answers to many questions, especially those which relatc to thc optimum order of application during bleaching, and to the respective delignification power of the various reagents. The reason for this lack of information comes partly from the fact that the actual modifications brought about to the residual lignin during the bleaching stages have very seldom been investigated [ The reactions of lignin model compounds or of kraft lignin cannot fully represent the behaviour of the insoluble and relatively unreactive residual lignin embedded in a cellulosic matrix. The approach described in this paper consists of analyzing the actual effect of the bleaching chemicals on the residual lignin. Basically two factors strongly influence lignin solubilization during bleaching. The first one is the amount of hydrophilic groups (mainly phenolic and carboxylic) and the second one is the size of the degraded lignin macromolecules. Several experimental procedures had to be developed. First the residual lignin was extracted in an almost quantitative way after each bleaching stage. Enzymatic hydrolysis of the carbohydrate fraction was achieved [1415] by using a very powerful enzyme mixture [IO]. Then a new technique based on the analysis of some fluoro derivatives by I9F NMR was applied for the determination of the main functional groups in the lignin structure [ The molecular weight distribution of lignin was also measured by gel permeation chromatography. With these tools in hand there was no obstacle to obtaining new and informative rzsults cjn the effect of the bleaching cheniicals (chlorine, chlorine dioxide, oxygen, hydrogen peroxide and ozone) on residual lignin and to improve our understanding of the bleaching process. EXPERIMENTAL Bleaching stages An unbleached softwood (roughly 50% Picea abies, 50% Pinus sylvestris) kraft pulp of kappa number 30 was used in this study. J173

2 The bleaching stages were carried out under the following conditions: Chlorine bleaching (C): room temperature, 3.5% consistency, 60 min, 2 and 4% C12 on pulp. After treatment the kappa numbers were 14.2 and 7.4, respectively. Chlorine dioxide bleaching (D): 70 C, 10% consistency, 60 min, 2 and 5% active Cl2 on pulp. After treatment, the kappa numbers were 21.1 and 12.0, respectively. Oxygen bleaching (0): 1 OO C, 10% consistency, 60 min, 3% NaOH on pulp, 0.5 MgS04, 7H20 on pulp, 5 bars oxygen. After treatment the kappa number was Hydrogen peroxide bleaching (P): 90 C, 10% consistency, 120 min, 2% NaOH on pulp, 3% H202 on pulp. After treatment the kappa number was Ozone bleaching (Z): room temperature, 35% consistency, 1.2% ozone consumed on pulp. Before treatment the pulp was acidified to ph 2.5 with sulphuric acid. After treatment the kappa number was Extraction of Residual Lignin Enzymatic hydrolysis was performed on the unbleached and on each treated pulp with a commercial cellulasehemicellulase preparation (ONOZUKA R10, Yakult Pharmaceutical Industries, Tokyo Japan). Hydrolysis was performed at ph 4.6 (acetic acidsodium acetate buffer) and 37 C. Five successive treatments of 72 h each were carried out. The residue was dissolved in dioxanewater (9: 1) and after evaporation solubilized in DMF and then precipitated with ether. Part of the lignin went into solution during the enzymatic hydrolysis. It was recovered by acidification to ph 2 with HCI, dissolution in DMF and precipitation with ether. The yield of lignin represented at least 80% of the theoretical content in pulp calculated according to the formula: lignin content in pulp (in per cent) = 0.15* kappa number). The carbohydrate impurities in the extracted lignin represented 4 to 6%. Residual proteins were of the order of 5% (average N content around 0.8 %). Each lignin sample was given the name of the treatment carried out just before extraction. Determination of OH Groups The lignin samples were esterified with 4fluorobenzoic anhydride following the procedure described in [ 171. Alcoholic and phenolic OH groups are reacting according to the reaction: R OH + FC6H4 CO O CO C6H4F > R O CO C&F + FC6HdCOOH In a second step, esterification of COOH groups in lignin was performed by reaction with the 4fluorophenyldiazomethane according to: RCOOH + F C&,CHN2 > RCO O CH,C,H,F The 4fluorophenyldiazomethane was obtained from 4fluorobenzylamine following the procedure described by Overberger and Anselme [ 181. The 4fluorophenyldiazomethane was recovered as a 0.5 moil solution in ether and was used just after its preparation. The lignin previously treated with 4fluorobenzoic anhydride (400 mg) was dissolved in 60 ml of dioxane and 20 ml of the solution of 4fluorophenyldiazomethane. After 24 h at 40 C, the volume was reduced to 5 ml by evaporation under reduced pressure. The derivatized lignin was recovered by precipitation with ether, washed with ether and dried. 19F NMR spectra of the derivatives were recorded at MHz on a Bruker AC 200 spectrometer as already described [1617]. The phenolic and alcoholic OH groups were measured after the first esterification and the carboxyl groups after the second one. Precision of the data is around 10%. Determination of Carbonyl Groups The carbonyl groups present in lignin were reacted with the 4fluorophenylhydrazine according to: \ / C = 0 + NH2 NH C,H,F \ > C = N NH C6H4F Lignin (100 mg) was dissolved in 5 mlofdioxane/dmf(l:l)andmixed with a solution of 4fluorophenylhydrazine (100 mg of 4fluorophenylhydrazine in 2 ml of DMF and 0.5 ml of orthophosphoric acid). The mixture was allowed to react for three days in the dark at ambient temperature. The derivatized lignin was re covered by precipitation with water, washed with water and dried. I9F NMR spectra were performed as before. Precision of the data is around 10%. Molecular Weight Distribution of Lignin The lignin samples were dissolved in DMF and their elution curves obtained by HPLC (polystyrene gel: PL gel mixed D, 2 columns) with a UV detector (flow rate 0.5 ml/min, 60 C). Analysis of Carbohydrates Lignin (100 mg) was treated with 20 ml of a 2 mol/l solution of trifluoroacetic acid at boiling temperature for 4 h. The hydrolysate was extracted twice with ethyl ether and evaporated to dryness. The residue was redissolved in 2 mlof water and analyzed by HPLC (Column: Polysphere OH Pb, Merck; solvent: water; flow rate: 0.4 ml/min; temperature: 80 C). RESULTS AND DISCUSSION Characterization of Residual Lignin Extraction of lignin by the enzymatic treatment gave preliminary information on its solubility at ph 4.6. Table I shows the respective weight (in percent of the theoretical content of lignin in pulp) of the insoluble and soluble fractions. Most of the residual lignin went into solution during enzymatic hydrolysis after oxygen, chlorine dioxide and hydrogen peroxide bleaching, indicating that these bleaching stages caused some depolymerization and created new hydrophilic groups. Solubilization was less after chlorination and very low after ozonation, indicating that chlorine and ozone differ radically from the other chemicals in their action on lignin. Table I1 gives the amount of the major functional groups in residual lignin after each bleaching stage. The quantity is expressed as the number of groups per 200 g of lignin. The results show substantial differences between the bleaching chemicals. The only one causing an increase in the amount J174

3 of free phenolic groups was chlorine. The others led to a significant decrease. A considerable amount of new carboxyl groups was created during ozonation, which confirms the results obtained with I3C NMR [IO]. A significant but smaller amount was observed after oxygen, chlorine dioxide and hydrogen peroxide treatments. Chlorination, on the contrary, introduced very few carboxyl groups. The alcoholic OH groups did not show any large change, suggesting that the side chains remained unaffected during the bleaching stages. Carbonyl groups were increased in the case of oxygen bleaching and to a lesser extent in chlorine dioxide bleaching. Demethoxylation was observed in all cases except ozonation. Figures 1 to 4 give the elution curve of the residual lignin before and after treatment with the bleaching chemicals (the high molecular weights are on the left part of the curves). Again, ozonation showed a peculiar feature since no depolymerization was observed in contrast to what happened after the other treatments. The greatest effect was produced by chlorination. Lignin depolymerization followed the order: C (4% C12) > 0 > D (5% active Cl2) = P > Z. Relevance to the Bleaching of Kraft Pulp These results will help to understand better the role of the bleaching chemicals. Chlorination of the aromatic rings in lignin cannot explain the extensive lignin removal during chlorine bleaching. It is clearly shown here that the lignin macromolecules are cleaved, with leads to the for E I I I I I c g 0.04 ' Unbl. c 2%... c 4% E I I Elution volume (ml) 0.02 i I I I I Elution volume (ml) Fig. 1. Elution curve of residual lignin in unbleached pulp (Unbl) and in chlorinetreated pulps (C). Fig. 2. Elution curve of residual lignin in unbleached pulp (Unbl) and in chlorine dioxidetreated pulp (D) I I I r I, I I E 0.07 m c P ' I I I 1 I Elutlon volume (mi) ' I I I I Elution volume (ml) Fig. 3. Elution curve of residual lignin in unbleached pulp (Unbl), and in pulps treated with oxygen (0) or hydrogen peroxide (P). Fig. 4. Comparison of the effect of the bleaching agents on the elution curves of residual lignin. (C chlorine; D chlorine dioxide; 0 oxygen; Z ozone) J175

4 mation of new phenolic groups. This is consistent with the mechanism recently described [2] where chlorine is shown to cause the hydrolysis of ether groups (OCH3 and remaining ether linkages). The substantial depolymerization observed in this study indicates that a fair amount of interunit ether linkages survive the kraft pulping process. For the first time, the highly phenolic character of the residual lignin after chlorination is demonstrated. This explains why chlorination activates a subsequent oxygen bleaching stage, as shown in several studies [ 191. Oxygen, being a radical, reacts primarily with the free phenolic groups. The very low content of carboxyl groups after chlorine treatment indicates that oxidation of the phenol or catechol groups does not take place to a great extent. The situation differs completely with chlorine dioxide. Instead of creating new free phenolic groups, C102 reacts with them and reduces their number. As aconsequence, chlorine dioxide is not an activating agent before oxygen bleaching. Depolymerization is less than with chlorine. Lignin dissolution during the D stage may be caused by the large number of carboxyl groups which are introduced. This confirms the fact the C102, as a radical, reacts mainly with the free phenolic groups and opens the aromatic ring to generate muconic acid derivatives [4]. This major reaction does not give rise to depolymerization. The behaviour of residual lignin during ozonation is quite unexpected. According to the molecular weight distribution, no depolymerization seems to take place. This is consistent with the small lignin fraction which passes into solution during the enzymatic hydrolysis. After ozonation the residual lignin looks like the lignin in unbleached pulp in many respects, except its considerable content in carboxyl groups. Since the number of OH alcoholic groups is not changed, the origin of the carboxyl groups must be the oxidation of aromatic rings, including the nonphenolic ones. It is suggested that the aromatic rings would be destroyed one by one, thereby introducing the carboxyl groups. The absence of depolymerization limits the removal of lignin, which would mean that ozonation must be combined with other stages. On the positive side, the high carboxyl content makes the final bleaching easier. Since no free phenolic groups are created during ozonation, ozone does not activate the lignin prior to oxygen bleaching. Many similarities exist between oxygen and chlorine dioxide bleaching. They both react with phenolic groups, generate new carboxyl groups and cause some depolymerization. Some carbonyl groups are introduced too. Oxygen and chlorine dioxide will therefore not complement each other very effectively in a bleaching sequence, contrary to chlorine and chlorine dioxide in a CED process. Residual lignin after hydrogen perox ide and oxygen bleaching is also very similar. This would suggest that hydrogen peroxide delignification proceeds like oxygen delignification. The species responsible for lignin degradation during peroxide treatment are not well known. The perhydroxyl anion HOO cannot degrade the phenolic groups [2O]. It has been claimed that the decomposition products of hydrogen peroxide (OHO, 020, 02) are the actual lignindegrading species [21]. The superoxide anion 020 was recently suggested as the key species in oxygen bleaching [22]. The results obtained in this study suggest that it would be the same in peroxide bleaching. The role of the perhydroxyl anion would be restricted to the elimination of carbonyl groups and thereby the destruction of colored groups. This explains why brightness development is better in a P stage than in an 0 stage. The lower carbonyl content after P is in agreement with this hypothesis. Consequently the only advantage of adding H202 in an 0 stage is the higher level of brightness reached. Another consequence is that a twostage OP process should not be an efficient process in terms of delignification. CONCLUSION This study presents new information on the effect of the bleaching chemicals on residual lignin in kraft pulp. This information is particularly useful in explaining some previous results and for defining optimum bleaching sequences. It appears that chlorine exhibits unique features which makes it without any equivalent among the known bleaching chemicals. Indeed none of the others has the capability to depolymerize the residual lignin while forming new free phenolic groups. A real substitute for chlorine must possess this property. Ozone, at the opposite extreme, does not depolymerize the residual lignin very efficiently. Consequently it must be associated with another chemical which has this capability. Apart from chlorine, oxygen is the best one. This suggests that OZ is a good sequence. Unfortunately, delignification must be limited in order to avoid severe cellulose degradation. Then a final stage is required. From the results obtained in this study, chlorine dioxide and hydrogen peroxide should be equally good candidates. However, some recent studies [IO] indicate that H202 causes cellulose degradation after an ozone stage. REFERENCES I. REEVE, D.W. and EARL, P.F., Chlorinated Organic Matter in Bleached Chemical Pulp Production: Part I, Environmental Impact and Regulation of Effluent, Pulp Paper Can. 90(4):6570 (I 989). 2. NI, Y. and Van HEININGEN, A.R.P., A New Mechanism for Pulp Delignification during Chlorination,.I. Pulp Paper Sci. 16( 1):J13 J19 (1990). 3. KOLAR, J.J., LINDGREN, B.O. and PETTERSSON, B., Chemical Reactions in FT PULPS, BLEACH, IDE, OZONE, CHEM J176

5 * Chlorine Dioxide Stages of Pulp Bleaching, Wood Sci. Technol. 17: ( 1983). 4. GELLERSTEDT, G., LINDFORS, E.L., 11 PETTERSSON, M., SJOHOLM, E. and ROBERT, D., Chemical Aspects on Chlorine Dioxide as a Bleaching Agent for Chemical Pulps, Proc. 6th Intl. Symp. Wood 12 Pulping Chem., Melbourne, (1991). 5. WARTIOVAARA, I., Reaction Mechanism of Effective Chlorine Dioxide Bleaching, Tuppi J. 69(2):8285 (1986). 6. NI, Y., KUBES, G.J. and Van HEININGEN, 13. A.R.P., Mechanism of Chlorate Formation During Bleaching of Kraft Pulp with Chlorine Dioxide, J. Pulp Paper Sci. 19(1):JIJ6 (1993) EK, M., GIERER, J. and JANSBO, K., Study on the Selectivity of Bleaching with Oxygen Containing Species, Hol7,forschung 43(6): (1989) ERIKSSON, T. and GIERER, J., Studies on the Ozonation of Structural Elements in Residual Kraft Lignins, J. Wood Chem. Technol. 5(1):5384 (1985). 9. GIERER, J., Basic Principles of Bleaching, Parts 1 and 2, Holzforschung 44(5):387394, ( 1990). 16. IO. CHIRAT, C. and LACHENAL, D., Effect of Ozone on Pulp Components. Application to Bleaching of Kraft Pulps, Holzforschung 48 (Suppl.): (1994). GELLERSTEDT, G., GUSTAFSSON, K. and LINDFORS, E.L., Structural Changes in Lignin During Oxygen Bleaching, Nordic Pulp PaperRes. J. l1(3):1417 (1986). GELLERSTEDT, G., LJUNGGREN, S. and PETTERSSON, M., Chemical Aspects of the Degradation of Lignin During Oxygen Bleaching, Proc. 6th Intl. Symp. Wood Pulping Chem., Melbourne, (1991). BACKMAN, L. and GELLERSTEDT, G., Reactions of Kraft Pulp Lignin with Alkaline Peroxide, Proc. 7th Intl. Symp. Wood Pulping Chem., Beijing, (1):223229(1993). LACHENAL D. and PAPADOPOULOS, J., Improvement of Hydrogen Peroxide Delignification, Cell. Chem. Technol. (22): (1988). HORTLING, B., TURUNEN, E. and SUNDQUIST, J., Isolation of Residual Lignin from Enzymatically Hydrolysed Pulps by Dissolution in Aprotic (DMAC) and Protic (Alkali) Solutions. Proc. 6th Intl. Symp. Wood Pulping Chem., Melbourne, (1991). BARRELLE, M., A New Method for the Quantitative I9F NMR Spectroscopic Analysis of Hydroxyl Groups in Lignins, Holzjor schung 47(3): (1993). 17. BARRELLE, M., FERNANDES, J.C., FROMENT, P. and LACHENAL, D., An Approach to the Determination of Functional Groups in Oxidized Lignins by I9F NMR, J. Wood Chem. Technol. 12(4): ( 1992). 18. OVERBERGER, C.G. and ANSELME, J.P., A Convenient Synthesis of Phenyldiazomethane, J. Org. Chem. 28: (1963). 19. LACHENAL, D., BOURSON, L., MU GUET, M. and CHAUVET, A,, Lignin Activation Improves Oxygen and Peroxide Delignification, Cellulose Chem. Technol (1990).,, 20. GIERER, J. and IMSGARD, F., The Reactions of Lignin with Oxygen and Hydrogen Peroxide in Alkaline Media, Svensk Pappersfidn. 80(16): (1977). 21. AGNEMO, R. and GELLERSTEDT, G., The Reactions of Lignin with Alkaline Hydrogen Peroxide. Part 11. Factors Influencing the Decomposition of Phenolic Structures, Acta Chem. Scand. B 33(5): (1979). 22. GIERER, J., YANG, E. and REITBERGER, T., The Role of Superoxide Anion Radicals in Delignification, Proc. 7th Intl. Symp. Wood Pulping Chem., Beijing, (1):24O 247 (1993). MICROGRAPHS NEEDED FOR THE FRONT COVERS OF JPPS Do you have any interesting micrographs which would be suitable for publication on the front covers of the Journal of Pulp and Paper Science? Preference is given to micrographs with esthetic appeal that contain useful scientific information. Coloured micrographs would be preferred, but black and white ones which could be printed with a coloured tint would also be considered. The micrographs should be 4 x 4 and submitted with a caption, including magnification, and your name, company affiliation and address, to: Dr. Derek Page Scientific Editor, Journal of Pulp and Paper Science c/o Paprican, 570 St. John s Blvd. Pointe Claire, QC, Canada H9R 359 Photo credits will be published for all micrographs used. J177

6 Y Fibre S H.A. CISNEROS, G. it. WILLIAMS and J.V. HATTO A fundamental study into the breakdown of aspen and birch fibres was undertaken to provide a better understanding of the peeling and fibrillation processes that occur during chip refining of hardwoods. Fibres of TMe CTMP and CMP pulps were analyzed in crosssection. The degrees to which the compound middle lamella and outer secondary wall (SI layer) were retained, and the S2 layer exposed, were recorded. Higher proportions of S2 layers were exposed in TMPfibres compared with CTMP and CMP fibres. Alkaline sulphite pretreatment of chips did not improve the degree of S2 layer exposure or the extent of fibrillation of the.fibres. These treated fibres retained most of their compound middle lamellae. Pulp strength was not related to the degree of INTRODUCTION 1 Mechanical pulps from bardwoods are important members of the large family of mechanical pulps available today and it is anticipated that their use will continue to increase, particularly in printing papers [1,2i. The stiefigth of these pulps is fiat satisfactory for their inclusion in printing papers unless some type of chemical treatment is applied during the pulping process [3,4]. The initial fibre length is not considered to be an important limiting factor for strength JP ps H.A. Cisneros, G.J. Williams and J.V. Hatton Paprican 3800 Wesbrook Mall Vancouver, BC V6S 2L9 s the structure of a this work was to analyze a large number of hardwood refiner pulp fibres in crosssection. The primary objective of this work, therefore, was to determine the effects of refiner mechanical pulping conditions on the surface development and cell wall damage of hardwood fibres; a secondary objective was to attempt to clarify the relationships between fibre surface development and pulp properties. This detailed microscopical study is expected to contribute to a better understanding of the behaviour of hardwood fibres during chip refining. due to its carbohydraterich Further, exvosure of the presumes the formation of fibrillar, \ loserich fines with improved bonding a ility. In addition, the fibres become mo flexible as the surface layers are removed [9]. The exposure of the S2 layer is particularly desirable for hardwood fibres. Since hardwoods have a higher concentration of carbohydrates in the S2 layer than do softwood tracheids [lo], a high surface bonding capacity would be expected for fibres from which the SI layers have been removed and the S2 layers exposed. A chemical treatment applied to the wood chips could cause the S 1 layer to peel off in a mamer similar tc that fer spruce TMP fibres [6]. This is known as the rollingsleeve mechanism or skinning, since the fibre outer layers are rolled back to expose the S2 layer. There is, however, no quantitative evidence that hardwood refiner pulp fibres from chemically treated chips would expose more S2 layer material than those produced from Fig. 1. Model of the cell wall structure of untreated chips. The longitudinal examinasoftwood tracheids and hardwood libriform fibres. ML = middle lamella, P = prition of tibres provides insufficient informa mary wall, S1 = secondary wall 1, S2 = tion about their surface or the pattem of secondarv wall 2. T = tertiarv wall. W = removal of the outer layers. Our approach in warty layer. 5178

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