Abstract
Anthraquinone has been widely utilized in the pulp and paper industry as a catalyst for alkaline cooking; however, its application has been recently restricted due to its potential carcinogenic effects. Hence, safer alternatives to anthraquinone have been explored. Agro-industrial by-products have been utilized as sustainable sources of value-added materials. In this study, teak (Tectona grandis) wood waste from Gunung Kidul, Indonesia, which naturally contains lapachol, was utilized as a biocatalyst to enhance delignification and improve pulp yield in alkaline cooking for pulp and paper production. The use of lapachol as a cooking catalyst was investigated for kraft, soda, and prehydrolysis soda cooking. Lapachol accelerated delignification and retained carbohydrate in all three alkaline cooking methods, with its effect being more pronounced in kraft cooking than in soda cooking. This study demonstrates that teak wood extractives with lapachol are promising sustainable catalysts for alkaline cooking.
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References
Algar WH, Farrington A, Jessup B, Nelson PF, Vanderhoek N (1979) The mechanism of soda-quinone pulping. Appita 33:33–37
Anderson S, Dimmel D, Izsak P (2003) A study aimed at understanding the AQ/Polysulfide synergistic effect in alkaline pulping. J Wood Chem Technol 23(2):141–159. https://doi.org/10.1081/WCT-120021922
Anita Y, Putra AS, Tanifuji K, Nakagawa-Izumi A, Ohi H, Evelyn E (2021a) Kraft cooking with teak wood extract and determination of residual 2-methylanthraquinone in eucalyptus pulp. Jpn Tappi J 75:153–163. https://doi.org/10.2524/jtappij.75.153
Anita Y, Utami SP, Ohi H, Evelyn E, Nakagawa-Izumi A (2021b) Mutagenicity of Tectona grandis wood extracts and their ability to improve carbohydrate yield for kraft cooking eucalyptus wood. Molecules 26:7171. https://doi.org/10.3390/molecules26237171
Anita Y, Sari EO, Nakagawa-Izumi A, Evelyn E, Ohi H (2023) Tectona grandis wood as a catalyst for delignification and carbohydrate protection during the kraft cooking of eucalyptus wood. Cellulose 30:3363–3375. https://doi.org/10.1007/s10570-023-05063-5
Babu MS, Mahanta S, Lakhter AJ, Hato T, Paul S, Naidu SR (2018) Lapachol inhibits glycolysis in cancer cells by targeting pyruvate kinase M2. PLoS ONE 13(2):e0191419. https://doi.org/10.1371/journal.pone.0191419
Bachman JE, Curtiss LA, Assary RS (2014) Investigation of the redox chemistry of anthraquinone derivatives using density functional theory. J Phys Chem A 118(38):8852–8860. https://doi.org/10.1021/jp5060777
Bajpai P (2018) Biermann’s handbook of pulp and paper vol 1: raw material and pulp making, 3rd edn. Elsevier, Amsterdam
Barbieri L, Andreola F, Lancellotti I, Taurino R (2013) Management of agricultural biomass wastes: preliminary study on characterization and valorisation in clay matrix bricks. Waste Manag 33(11):2307–2315. https://doi.org/10.1016/j.wasman.2013.03.014
Barbosa TP, Neto HD (2013) Preparation of lapachol derivatives in acid and base media: proposed experiments for organic chemistry laboratory classes (preparação de derivados do lapachol em meio ácido e em meio básico: uma proposta de experimentos para a disciplina de química orgânica experimental). Quím Nova 36:331–334. https://doi.org/10.1590/S0100-40422013000200021
Bard AJ, Parsons B, Jordon J (eds) (1985) Standard potentials in aqueous solutions. Dekker, New York
Barreto ES, Baeta BEL, Pereira MC, Pasquini D, Guimaraes VM, Gurgel LVA (2020) 2-Hydroxy-1,4-naphtoquinone (lawsone) as a redox catalyst for the improvement of the alkaline pretreatment of sugarcane bagasse. Energy Fuels 34:16228–16239. https://doi.org/10.1021/acs.energyfuels.0c02990
Bränvall E (2017) Limits of delignification in kraft cooking. BioResources 12(1):2081–2107
Budiaman A, Komalasari P (2012) Waste of felling and on-site production of teak squarewood of the community forest. J Man Hut Trop 18(3):164–168. https://doi.org/10.7226/jtfm.18.3.164
Chávez-Salgado LP, Vandenbossche V, Vilarem G (2022) Tectona grandis Linn. f. secondary metabolites and their bioactive potential: a review. Iforest 15(2):112–120. https://doi.org/10.3832/ifor3714-015
Chem M, Tanifuji K, Utami SV, Putra AS, Ohi H, Nakagawa-Izumi A (2022) Development of dissolving pulp from Phyllostachys pubescens stem by prehydrolysis soda cooking with 2-methylanthraquinone. Ind Crops Prod 178:114570. https://doi.org/10.1016/j.indcrop.2022.114570
Chen S, Zhang X, Ling Z, Ji Z, Ramarao BV, Ramaswamy S, Xu F (2016) Probing and visualizing the heterogeneity of fiber cell wall deconstruction in sugar maple (Acer saccharum) during liquid hot water pretreatment. RSC Adv 6:79297–79306. https://doi.org/10.1039/C6RA18333F
Delarmelina M, Nicoletti CD, Moraes MC, Bühl DOF, Silva FC, Ferreira VF, Carneiro JWM (2018) α- and β-lapachone isomerization in acidic media: insights from experimental and implicit/explicit solvation approaches. ChemPlusChem 84:52–56. https://doi.org/10.1002/cplu.201800485
Dimmel DR, Althen E, Savidakis MC, Courchene C, Bozell JJ (1999) New quinone-based pulping catalyst. Tappi J 82:83–89
Dimmel DR, Sklar PI, Crews KE, Pullman GS (2000) Pulping catalysts in trees. J Wood Chem Technol 20(3):225–242. https://doi.org/10.1080/02773810009349634
Eshun JF, Potting J, Leemans R (2012) Wood waste minimization in the timber sector of Ghana: a systems approach to reduce environmental impact. J Clean Prod 26:67–78. https://doi.org/10.1016/j.jclepro.2011.12.025
Fearon O, Nykänen V, Kuitunen S, Ruuttunen K, Alén R, Alopaeus V, Vuorinen T (2020) Detailed modeling of the kraft pulping chemistry: carbohydrate reactions. AIChE J 66(8):e16252. https://doi.org/10.1002/aic.1625
Fišerová M, Gigac J (2006) Application of anthraquinone in kraft pulping. Wood Res 51(4):55–68
Francis RC, Shin SJ, Omori S, Amidon TE, Blain TJ (2006) Soda pulping of hardwoods catalyzed by AQ and methyl substituted AQs. J Wood Chem Technol 26(2):141–152. https://doi.org/10.1080/02773810600701737
Francis RC, Schnelle ST, Nicholson DJ, Agblevor FA, Kiemle DJ (2021) 2-methyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione (Me-THAD) as a catalyst in alkaline chemical pulping. J Wood Chem Technol 41:249–260. https://doi.org/10.1080/02773813.2021.1976798
Hardiyanto EB, Prayitno TA (2008) Present utilization of small-diameter teak log from community teak plantations in Java and Eastern Indonesia. Technical Report ITTO PPD 121/06 Rev. 2(I) https://www.itto.int/files/itto_project_db_input/2592/Technical/PPD12106%20%20Technical%20Report%20.pdf. Accessed 20 July 2023
Hart PW, Rudie AW (2014) Anthraquinone: a review of the rise and fall of a pulping catalyst. Tappi J 13:23–31. https://doi.org/10.32964/TJ13.10.23
Haryanto A, Hidayat W, Hasanudin U, Iryani DA, Kim S, Lee S, Yoo J (2021) Valorization of Indonesian wood wastes through pyrolysis: a review. Energies 14(1407):1–25. https://doi.org/10.3390/en14051407
IARC Groups (2021) Agents classified by the IARC Monographs, volumes 1-129-IARC monographs on the identification of carcinogenic hazards to humans (who.int). https://monographs.iarc.who.int/agents-classified-by-the-iarc/(accessed). Accessed 09 May 2022
Komatsu T, Usui K (1983) Process for producing 1,4,4A,9A-tetrahydroanthraquinone (US4412954A). US Patent. 4,412,954. https://patents.google.com/patent/US4412954A/en. Accessed 10 Sept 2023
Laurenco A, Gominho J, Marques AV, Pereira H (2012) Reactivity of syringyl and guaiacyl lignin units and delignification kinetics in the kraft pulping of Eucalyptus globulus wood using Py-GC-MS/FID. Bioresour Technol 123:296–302. https://doi.org/10.1016/j.biortech.2012.07.092
Lukmandaru G, Takahashi K (2009) Radial distribution of quinones in plantation teak (Tectona grandis L.f.). Ann for Sci 66:605. https://doi.org/10.1051/forest/2009051
Lukmandaru G, Ashitani T, Takahashi K (2009) Color and chemical characterization of partially black-streaked heartwood in teak (Tectona grandis). J for Res 20:377–380. https://doi.org/10.1007/s11676-009-0064-5
Marques LB, Ottoni FM, Pinto MCX, Ribeiro JM, Sousa F, Weinlich R, Victo NC, Kisitu J, Holzer AK, Leist M, Alves RJ, Souza-Fagundes EM (2020) Lapachol acetylglycosylation enhances its cytotoxic and pro-apoptotic activities in HL60 cells. Toxicol in Vitro 65:104772. https://doi.org/10.1016/j.tiv.2020.104772
Miranda SEM, Lemos JA, Fernandes RS, Silva JO, Ottoni FM, Townsend DM, Rubello D, Alves RJ, Cassali GD, Ferreira LAM, Barros ALB (2021) Enhanced antitumor efficacy of lapachol-loaded nanoemulsion in breast cancer tumor mode. Biomed Pharmacother 133:110936. https://doi.org/10.1016/j.biopha.2020.110936
Mongkhonsiri G, Anantpinijwatna A, Charoensuppanimit P, Arpornwichanop A, Gani R, Assabumungrat S (2021) Development of sustainable integrated biorefinery networks in pulp and paper industries. Comput Aided Chem Eng 50:1517–1522. https://doi.org/10.1016/B978-0-323-88506-5.50234-5
Nomura Y, Nakamura M (1978) Studies on quinone additive cooking part 1: effect of quinone addition on alkaline cooking. Jpn Tappi J 32:713–721. https://doi.org/10.2524/jtappij.32.12_713
Prince RC, Dutton PL, Gunner MR (2022) The aprotic electrochemistry of quinones. Biochim Biophys Acta Bioenerg 1863(2022):148558. https://doi.org/10.1016/j.bbabio.2022.148558
Ralph J, Ede RM, Robinson NP, Main L (1987) Reactions of β-aryl lignin model Quinone methides with anthrahydroquinone and anthranol. J Wood Chem Technol 7(2):133–160
Salaghi A, Putra AS, Maryana R, Kajiyama M, Ohi H (2018) Preparation of dissolving pulp by totally chlorine-free bleaching: roles of hardwood syringyl and guaiacyl lignins. Jpn Tappi J 72:1167–1175. https://doi.org/10.2524/jtappij.72.1167
Salaghi A, Putra AS, Rizaluddin AT, Kajiyama M, Ohi H (2019) Totally chlorine-free bleaching of prehydrolysis soda pulp from plantation hardwoods consisting of various lignin structures. J Wood Sci 65:10. https://doi.org/10.1186/s10086-019-1785-5
Samp JC (2008) A comprehensive mechanism for anthraquinone mass transfer in alkaline pulping. Georgia Institute of Technology, Atlanta
Utami SP, Sari EO, Chem M, Ohi H, Evelyn N-I (2023) Isolation of cellulose and lignin from Acacia crassicarpa and Eucalyptus pellita wood by prehydrolysis soda cooking with 2-methylanthraquinone as a green additive. Wood Sci Technol 57:253–273. https://doi.org/10.1007/s00226-022-01446-2
Vyas P, Yadav DK, Khandelwal P (2019) Tectona grandis (teak)–a review on its phytochemical and therapeutic potential. Nat Prod Res 33:2338–2354. https://doi.org/10.1080/14786419.2018.1440217
Wozniak JC, Dimmel DR, Malcolm EW (1989) The generation of quinones from lignin and lignin related compounds. J Wood Chem Technol 9(4):491–511. https://doi.org/10.1080/02773818908050312
Acknowledgements
Acacia crassicarpa was kindly provided by Mr. Azka Aman, PT. Riau Andalan Pulp and Paper. Eucalyptus pellita was kindly provided by Mr. Kosyke Imai, PT. Tanjungenim Lestari Pulp and Paper.
Funding
Esty Octiana Sari is grateful to the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japan for providing a scholarship to conduct the current research under the MEXT Special Scholarship Program on Trans-World Professional Human Resources Management for a Doctoral Course.
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EOS and HO contributed to the study conception and design. Data were collected by EOS, with SPU contributing to the experiments. Data analysis was performed by EOS. The GC–MS and NMR analyses were performed by AN-I. EOS wrote the first draft of this manuscript. HO, SPU, and AN-I reviewed the manuscript. The study was supervised by Hiroshi Ohi and Akiko Nakagawa-Izumi.
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Sari, E.O., Utami, S.P., Nakagawa-Izumi, A. et al. Lapachol from Indonesian teak (Tectona grandis) wood waste as a natural additive for alkaline cooking. Wood Sci Technol 58, 627–647 (2024). https://doi.org/10.1007/s00226-024-01537-2
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DOI: https://doi.org/10.1007/s00226-024-01537-2