Sustainable conversion regenerated cellulose into cellulose oleate by sonochemistry

Abstract

Derivatization has great potential for the high-value utilization of cellulose by enhancing its processability and functionality. However, due to the low reactivity of natural cellulose, it remains challenging to rapidly prepare cellulose derivatives with high degrees of substitution. The “cavitation effect” of ultrasound can reduce the particle size and crystalline index of cellulose, which provides a possible method for preparing cellulose derivatives. Herein, a feasible method was proposed for efficiently converting regenerated cellulose to cellulose oleate with the assistance of ultrasonic treatment. By adjusting the reaction conditions including ultrasonic intensity, feeding ratios of oleic acid, reaction time, and reaction solvent, a series of cellulose oleates with degrees of substitution ranging from 0.37 to 1.71 were synthesized. Additionally, the effects of different reaction conditions on the chemical structures, crystalline structures, and thermal behaviors were investigated thoroughly. Cellulose oleates with degrees of substitution exceeding 1.23 exhibited amorphous structures and thermoplasticity with glass transition temperatures at 159.8 to 172.6 °C. This study presented a sustainable and practicable method for effectively derivatizing cellulose.

Graphical abstract

Keywords

regenerated cellulose / cellulose oleate / sonochemistry / degree of substitution / thermoplasticity

References

[1] Nadeem H, Athar M, Dehghani M, Garnier G, Batchelor W. Recent advancements, trends, fundamental challenges and opportunities in spray deposited cellulose nanofibril films for packaging applications. Science of the Total Environment, 2022, 836: 155654

[2] Janaswamy S, Yadav M P, Hoque M, Bhattarai S, Ahmed S. Cellulosic fraction from agricultural biomass as a viable alternative for plastics and plastic products. Industrial Crops and Products, 2022, 179: 114692

[3] Li T, Chen C, Brozena A H, Zhu J Y, Xu L, Driemeier C, Dai J, Rojas O J, Isogai A, Wågberg L, Hu L. Developing fibrillated cellulose as a sustainable technological material. Nature, 2021, 590(7844): 47–56

[4] Tu H, Zhu M, Duan B, Zhang L. Recent progress in high-strength and robust regenerated cellulose materials. Advanced Materials, 2021, 33(28): 2000682

[5] Xia Z, Li J, Zhang J, Zhang X, Zheng X, Zhang J. Processing and valorization of cellulose, lignin and lignocellulose using ionic liquids. Journal of Bioresources and Bioproducts, 2020, 5(2): 79–95

[6] Lu Y, Wu Y. Influence of coagulation bath on morphology of cellulose membranes prepared by NMMO method. Frontiers of Chemical Engineering in China, 2008, 2(2): 204–208

[7] Dufresne A. Cellulose nanomaterial reinforced polymer nanocomposites. Current Opinion in Colloid & Interface Science, 2017, 29: 1–8

[8] Wu B, Geng B, Chen Y, Liu H, Li G, Wu Q. Preparation and characteristics of TEMPO-oxidized cellulose nanofibrils from bamboo pulp and their oxygen-barrier application in PLA films. Frontiers of Chemical Science and Engineering, 2017, 11(4): 554–563

[9] Zhang X, Cheng Y, You J, Zhang J, Yin C, Zhang J. Ultralong phosphorescence cellulose with excellent anti-bacterial, water-resistant and ease-to-process performance. Nature Communications, 2022, 13(1): 1117

[10] Wang N, Ding E, Cheng R. Surface modification of cellulose nanocrystals. Frontiers of Chemical Engineering in China, 2007, 1(3): 228–232

[11] Yao P, Gong H, Wu Z Y, Fu H, Li B, Zhu B, Ji J, Wang X, Xu N, Tang C, Zhang H, Zhu J. Greener and higher conversion of esterification via interfacial photothermal catalysis. Nature Sustainability, 2022, 5(4): 348–356

[12] Edgar K J, Buchanan C M, Debenham J S, Rundquist P A, Seiler B D, Shelton M C, Tindall D. Advances in cellulose ester performance and application. Progress in Polymer Science, 2001, 26(9): 1605–1688

[13] Arca H C, Mosquera-Giraldo L I, Bi V, Xu D, Taylor L S, Edgar K J. Pharmaceutical applications of cellulose ethers and cellulose ether esters. Biomacromolecules, 2018, 19(7): 2351–2376

[14] El SeoudO AHeinzeT. Organic esters of cellulose: new perspectives for old polymers. In: Heinze T, ed. Polysaccharides I: Structure, Characterization and Use. Berlin: Springer, 2005, 103–149

[15] Jia R, Tian W, Bai H, Zhang J, Wang S, Zhang J. Amine-responsive cellulose-based ratiometric fluorescent materials for real-time and visual detection of shrimp and crab freshness. Nature Communications, 2019, 10(1): 795

[16] Esen E, Hädinger P, Meier M A R. Sustainable fatty acid modification of cellulose in a CO₂-based switchable solvent and subsequent thiol-ene modification. Biomacromolecules, 2021, 22(2): 586–593

[17] Bendaoud A, Chalamet Y. Plasticizing effect of ionic liquid on cellulose acetate obtained by melt processing. Carbohydrate Polymers, 2014, 108: 75–82

[18] Zhang G, Huang K, Jiang X, Huang D, Yang Y. Acetylation of rice straw for thermoplastic applications. Carbohydrate Polymers, 2013, 96(1): 218–226

[19] Duchatel-Crépy L, Joly N, Martin P, Marin A, Tahon J F, Lefebvre J M, Gaucher V. Substitution degree and fatty chain length influence on structure and properties of fatty acid cellulose esters. Carbohydrate Polymers, 2020, 234: 115912

[20] Chen Z, Zhang J, Xiao P, Tian W, Zhang J. Novel thermoplastic cellulose esters containing bulky moieties and soft segments. ACS Sustainable Chemistry & Engineering, 2018, 6(4): 4931–4939

[21] Huang L, Wu Q, Wang Q, Wolcott M. One-step activation and surface fatty acylation of cellulose fibers in a solvent-free condition. ACS Sustainable Chemistry & Engineering, 2019, 7(19): 15920–15927

[22] Kanwar S, Ali U, Mazumder K. Effect of cellulose and starch fatty acid esters addition on microstructure and physical properties of arabinoxylan films. Carbohydrate Polymers, 2021, 270: 118317

[23] Onwukamike K N, Grelier S, Grau E, Cramail H, Meier M A R. Critical review on sustainable homogeneous cellulose modification: why renewability is not enough. ACS Sustainable Chemistry & Engineering, 2019, 7(2): 1826–1840

[24] Wang P, Tao B Y. Synthesis and characterization of long-chain fatty acid cellulose ester (FACE). Journal of Applied Polymer Science, 1994, 52(6): 755–761

[25] Morooka T, Norimoto M, Yamada T, Shiraishi N. Dielectric properties of cellulose acylates. Journal of Applied Polymer Science, 1984, 29(12): 3981–3990

[26] Malm C J, Mench J W, Kendall D L, Hiatt G D. Aliphatic acid esters of cellulose: preparation by acid-chloride-pyridine procedure. Industrial & Engineering Chemistry, 1951, 43(3): 684–688

[27] Guiao K S, Gupta A, Tzoganakis C, Mekonnen T H. Reactive extrusion as a sustainable alternative for the processing and valorization of biomass components. Journal of Cleaner Production, 2022, 355: 131840

[28] Chatel G, Varma R S. Ultrasound and microwave irradiation: contributions of alternative physicochemical activation methods to green chemistry. Green Chemistry, 2019, 21(22): 6043–6050

[29] Amaniampong P N, Trinh Q T, De Oliveira Vigier K, Dao D Q, Tran N H, Wang Y, Sherburne M P, Jerome F. Synergistic effect of high-frequency ultrasound with cupric oxide catalyst resulting in a selectivity switch in glucose oxidation under argon. Journal of the American Chemical Society, 2019, 141(37): 14772–14779

[30] Lan L, Chen H, Lee D, Xu S, Skillen N, Tedstone A, Robertson P, Garforth A, Daly H, Hardacre C, Fan X. Effect of ball-milling pretreatment of cellulose on its photoreforming for H₂ production. ACS Sustainable Chemistry & Engineering, 2022, 10(15): 4862–4871

[31] Yang C, Yuan X, Wang X, Wu K, Liu Y, Liu C, Lu H, Liang B. Ball milling promoted direct liquefaction of lignocellulosic biomass in supercritical ethanol. Frontiers of Chemical Science and Engineering, 2020, 14(4): 605–613

[32] Chatel G, De Oliveira Vigier K, Jerome F. Sonochemistry: what potential for conversion of lignocellulosic biomass into platform chemicals?. ChemSusChem, 2014, 7(10): 2774–2787

[33] Bussemaker M J, Zhang D. Effect of ultrasound on lignocellulosic biomass as a pretreatment for biorefinery and biofuel applications. Industrial & Engineering Chemistry Research, 2013, 52(10): 3563–3580

[34] Zhang Q, Benoit M, De Oliveira Vigier K, Barrault J, Jégou G, Philippe M, Jérôme F. Pretreatment of microcrystalline cellulose by ultrasounds: effect of particle size in the heterogeneously-catalyzed hydrolysis of cellulose to glucose. Green Chemistry, 2013, 15(4): 963–969

[35] Aimin T, Hongwei Z, Gang C, Guohui X, Wenzhi L. Influence of ultrasound treatment on accessibility and regioselective oxidation reactivity of cellulose. Ultrasonics Sonochemistry, 2005, 12(6): 467–472

[36] Hou D F, Tan H, Li M L, Tang Y, Liu Z Y, Yang W, Yang M B. Synthesis of thermoplastic cellulose grafted polyurethane from regenerated cellulose. Cellulose, 2020, 27(15): 8667–8679

[37] Hou D F, Li M L, Yan C, Zhou L, Liu Z Y, Yang W, Yang M B. Mechanochemical preparation of thermoplastic cellulose oleate by ball milling. Green Chemistry, 2021, 23(5): 2069–2078

[38] Samaranayake G, Glasser W G. Cellulose derivatives with low DS. I. A novel acylation system. Carbohydrate Polymers, 1993, 22(1): 1–7

[39] Zhou L, Zhai Y M, Yang M B, Yang W. Flexible and tough cellulose nanocrystal/polycaprolactone hybrid aerogel based on the strategy of macromolecule cross-linking via click chemistry. ACS Sustainable Chemistry & Engineering, 2019, 7(18): 15617–15627

[40] Jing M, Zhang L, Fan Z, Liu X, Wang Y, Liu C, Shen C. Markedly improved hydrophobicity of cellulose film via a simple one-step aminosilane-assisted ball milling. Carbohydrate Polymers, 2022, 275: 118701

[41] Liu C, Li M C, Chen W, Huang R, Hong S, Wu Q, Mei C. Production of lignin-containing cellulose nanofibers using deep eutectic solvents for UV-absorbing polymer reinforcement. Carbohydrate Polymers, 2020, 246: 116548

[42] Onwukamike K N, Grelier S, Grau E, Cramail H, Meier M A R. Sustainable transesterification of cellulose with high oleic sunflower oil in a DBU-CO₂ switchable solvent. ACS Sustainable Chemistry & Engineering, 2018, 6(7): 8826–8835

[43] Jebrane M, Terziev N, Heinmaa I. Biobased and sustainable alternative route to long-chain cellulose esters. Biomacromolecules, 2017, 18(2): 498–504

[44] Zhong Y, Wu J, Kang H, Liu R. Choline hydroxide based deep eutectic solvent for dissolving cellulose. Green Chemistry, 2022, 24(6): 2464–2475

[45] Xi Y, Zhang L, Tian Y, Song J, Ma J, Wang Z. Rapid dissolution of cellulose in an AlCl₃/ZnCl₂ aqueous system at room temperature and its versatile adaptability in functional materials. Green Chemistry, 2022, 24(2): 885–897

[46] Hirase R, Miyamoto H, Yuguchi Y, Yamane C. Dissolution of cellulose into supercritical water and its dissolving state followed by structure formation from the solution system. Carbohydrate Polymers, 2022, 275: 118669

[47] Jing Y, Wu C, Zhang X, Su S, Mahmud S, Zhu J. Construction of anti-counterfeiting pattern on the cellulose film by in-situ regulation strategies. Cellulose, 2022, 29(14): 7751–7760

[48] Zhang L, Jiang Z, Yang S, Zeng Z, Zhang W, Zhang L. Different rheological behaviours of cellulose/tetrabutylammonium acetate/dimethyl sulfoxide/water mixtures. Cellulose, 2020, 27(14): 7967–7978

[49] Wei L, Song J, Cheng B, Yang Z. Synthesis, characterization and antibacterial properties of novel cellulose acetate sorbate. Carbohydrate Polymers, 2020, 243: 116416

[50] Crépy L, Miri V, Joly N, Martin P, Lefebvre J M. Effect of side chain length on structure and thermomechanical properties of fully substituted cellulose fatty esters. Carbohydrate Polymers, 2011, 83(4): 1812–1820

Conflicts of interest

There are no conflicts to declare.

Acknowledgements

The authors are grateful for financial support from the National Natural Science Foundation of China (Grant Nos. 52273040 and 51873128) and Yunnan Fundamental Research Projects (Grant No. 202301AT070232). Moreover, the authors thank Dr. Xiao-Rong Sun from the National Demonstration Center for Experimental Materials Science and Engineering Education of Sichuan University for her help in the SEM test.

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-023-2317-9 and is accessible for authorized users.

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