Abstract
The ester acid method primarily employs sulfuric acid (H2SO4) as a catalyst and is used in the current cellulose triacetate (CTA) industry from cotton linters. However, the problems of acid wastewater and cellulose degradation caused by H2SO4 still need to be solved. In this study, CTA was successfully produced from bleached softwood dissolving pulp (BSDP) utilizing the recyclable solid acid p-toluenesulfonic acid (p-TsOH). CTA prepared using either H2SO4 or p-TsOH with the same degree of substitution (DS) or the same H+ concentration was compared. The results show that p-TsOH-treated CTA demonstrated better performance in terms of the degree of polymerization (DP), dispersion stability, acetylation rate, and thermal stability. The mechanism for polymerization of acetylation catalyzed by p-TsOH was postulated. The results suggest that using p-TsOH can reduce carbohydrate degradation, solve the problem of inorganic acid derivatization, and allow the use of alternative cellulose resources—bleached wood fibers for producing CTA.
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References
Ali S, Khatri Z, Oh KW, Kim IS, Kim SH (2014) Zein/cellulose acetate hybrid nanofibres: electrospinning and characterization. Macromol Res 22(9):971–977
ASTM D871-96 (2019) Standard Test Methods of Testing Cellulose Acetate, ASTM International, West Conshohocken, PA, 2019, www.astm.org
Cao L, Luo G, Tsang DCW, Chen H, Zhang S, Chen J (2018) A novel process for obtaining high-quality cellulose acetate from green landscaping waste. J Clean Prod 176:338–347
Celebioglu A, Demirci S, Uyar T (2014) Cyclodextrin-grafted electrospun cellulose acetate nanofibres via “Click” reaction for removal of phenanthrene. Appl Surf Sci 305:581–588
Cerveira GS, Borges CP, de Araujo Kronemberger F (2018) Gas permeation applied to biogas upgrading using cellulose acetate and polydimethylsiloxane membranes. J Clean Prod 187:830–838
Chen J, Jikun X, Wang K, Cao X, Sun R (2016) Cellulose acetate fibers prepared from different raw materials with a rapid synthesis method. Carbohydr Polym 137:685–692
Edgar KJ, Buchanan CM, Debenhan JS, Rundquist PA, Seiler BD, Shelton MC et al (2001) Advances in cellulose ester performance and application. Prog Polym Sci 26:1605–1688
El Nemr A, Ragab S, El Sikaily A, Khaled A (2015) Synthesis of cellulose triacetate from cotton cellulose by using NIS as a catalyst under mild reaction conditions. Carbohyd Polym 130:41–48
Fischer S, Thümmler K, Volkert B, Hettrich K, Schmidt I, Fischer K (2008) Properties and applications of cellulose acetate. Macromol Symp 262(1):89–96
French AD (2014) Idealized powder diffraction patterns for cellulose polymorphs. Cellulose 21:885–896
French AD (2020) Increment in evolution of cellulose crystallinity analysis. Cellulose 27(10):5445–5448
French AD, Santiago Cintrón M (2013) Cellulose polymorphy, crystallite size, and the segal crystallinity index. Cellulose 20(1):583–588
Goda K, Sreekala MS, Gomes A, Kaji T, Ohgi J (2006) Improvement of plant-based natural fibers of toughening green composites—effect of load application during mercerization of ramie fibers. Compos A: Appl Sci Manuf 37:2213–2220
Habibi Y, Lucia LA, Rojas OJ (2010) Cellulose nanocrystals: chemistry, self-assembly, and applications. Chem Rev 110(6):3479–3500
He Z, Meng M, Yan L, Zhu W, Sun F, Yan Y et al (2015) Fabrication of new cellulose acetate blend imprinted membrane assisted with ionic liquid ([BMIM]Cl) for selective adsorption of salicylic acid from industrial wastewater. Sep Purif Technol 145:63–74
Klemm D, Philipp B, Heinze T, Heinze U, Wagenknecht W (1998a) Comprehensive cellulose chemistry: fundamentals and analytical methods. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Klemm D, Philipp B, Heinze T, Heinze U, Wagenknecht W (1998b) Comprehensive cellulose chemistry: functionalization of cellulose. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Kono H, Hashimoto H, Shimizu Y (2015) NMR characterization of cellulose acetate: chemical shift assignments, substituent effects, and chemical shift additivity. Carbohyd Polym 118:91–100
Kuo CM (1988) A short-course on cellulose esters. ACS Symp Series 196:24
Ohlrogge J, Allen D, Berguson B, DellaPenna D, Shachar-Hill Y, Stymne S (2009) Driving on biomass. Science 324(5930):1019–1020
Roche EJ, Chanzy HD, Boudeulle M, Marchessault RH, Sundararajan PR (1978) Three-dimensional crystalline structure of cellulose triacetate II. Macromolecules 11:86–94
Schilling M, Bouchard M, Khanjian H, Learner T, Phenix A, Rivenc R (2010) Application of chemical and thermal analysis methods for studying cellulose ester plastics. Acc Chem Res 43(6):888–896
Shangyu J, Minhua C (2016) Liquid chromatography detection technology of para toluene sulfonic acid in chemical products. Modern Chem Res 12:25–26
Sun XW, Lu CH, Zhang W, Tian D, Zhang XX (2013) Acetone-soluble cellulose acetate extracted from waste blended fabrics via ionic liquid catalyzed acetylation. Carbohyd Polym 98(1):405–411
Tang L, Huang B, Qilin Lu, Wang S, Wen Ou, Lin W, Chen X (2013) Ultrasonication-assisted manufacture of cellulose nanocrystals esterified with acetic acid. Biores Technol 127:100–105
Acknowledgments
The authors acknowledge Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Provincial Key Lab of Pulp & Paper Science & Technology, Nanjing Forestry University, which made it possible to finish this work.
Funding
This work was funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) and the National Natural Science Foundation of China Youth Project: Emulsion liquid membrane separation mechanism based on deformation memory microreactor and its solid/liquid interface stability (52103112).
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XZ: Investigation, experimentalize, methodology, software, data curation, writing—original manuscript. FZ: methodology, funding support. PL: investigation, reviewing. GT: conceptualization, methodology, supervision, project administration.
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Zhang, X., Zhang, F., Li, P. et al. Synthesis of cellulose triacetate from softwood dissolving pulp using p-toluenesulfonic acid and its properties. Cellulose 30, 6787–6797 (2023). https://doi.org/10.1007/s10570-023-05294-6
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DOI: https://doi.org/10.1007/s10570-023-05294-6