Sustainable conversion regenerated cellulose into cellulose oleate by sonochemistry
Sustainable conversion regenerated cellulose into cellulose oleate by sonochemistry
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.
regenerated cellulose / cellulose oleate / sonochemistry / degree of substitution / thermoplasticity
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[7] |
Dufresne A. Cellulose nanomaterial reinforced polymer nanocomposites. Current Opinion in Colloid & Interface Science, 2017, 29: 1–8
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[10] |
Wang N, Ding E, Cheng R. Surface modification of cellulose nanocrystals. Frontiers of Chemical Engineering in China, 2007, 1(3): 228–232
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[17] |
Bendaoud A, Chalamet Y. Plasticizing effect of ionic liquid on cellulose acetate obtained by melt processing. Carbohydrate Polymers, 2014, 108: 75–82
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[25] |
Morooka T, Norimoto M, Yamada T, Shiraishi N. Dielectric properties of cellulose acylates. Journal of Applied Polymer Science, 1984, 29(12): 3981–3990
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[38] |
Samaranayake G, Glasser W G. Cellulose derivatives with low DS. I. A novel acylation system. Carbohydrate Polymers, 1993, 22(1): 1–7
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[43] |
Jebrane M, Terziev N, Heinmaa I. Biobased and sustainable alternative route to long-chain cellulose esters. Biomacromolecules, 2017, 18(2): 498–504
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
[49] |
Wei L, Song J, Cheng B, Yang Z. Synthesis, characterization and antibacterial properties of novel cellulose acetate sorbate. Carbohydrate Polymers, 2020, 243: 116416
CrossRef
ADS
Google scholar
|
[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
CrossRef
ADS
Google scholar
|
/
〈 | 〉 |