journal article·2025-03

Activation behavior of 4-AcNH-TEMPO by ClO2 for selective oxidation of cellulose in DMAc/LiCl system

Yao Zhao, Xueping Wang, Bowen Li, Tian Si, Xin Gao, Lincai Peng, Heng Zhang

Cellulose· Volume 32· Issue 5
Publisher page

Abstract

Abstract The cellulose catalytic oxidation system mainly comprises of inorganic ion-based oxidants. Hence, the selective oxidation of C6−primary hydroxyls (C6-OH) of cellulose, catalyzed by piperidine free radicals, was limited to the homogeneous cellulosic system containing protic solvents or heterogeneous system. In this work, use of the catalytic system containing 4-acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (4-AcNH-TEMPO) was extended to the cellulosic solution in N, N-dimethylacetamide (DMAc) and combined with chlorine dioxide. Results showed that the carboxyl content was 0.832 mmol/g. Meanwhile, the degree of polymerization decreased slightly from 900 to 489. This study provides an effective route for the homogeneous selective oxidation of primary hydroxyl groups in cellulose and explored its oxidation mechanism in DMAc solvent. Furthermore, studies showed that the reactive chlorine species- ClO•, Cl•, and ClO2 played a crucial role in the oxidation process. The methodology developed here displayed great potential to be utilized to various biomolecules in aprotic solvents homogeneous system based on 4-AcNH-TEMPO as oxidation catalysts.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Advanced Cellulose Research Studies · Enzyme-mediated dye degradation · Lignin and Wood Chemistry

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (95)

Show source-provided references
1. Abral H, Lawrensius V, Handayani D, Sugiarti E (2018) Preparation of nano-sized particles from bacterial cellulose using ultrasonication and their characterization. Carbohydr Polym 191:161–167. https://doi.org/10.1016/j.carbpol.2018.03.02610.1016/j.carbpol.2018.03.026 ↗
2. Aravind P, Subramanyan V, Ferro S, Gopalakrishnan R (2016) Eco-friendly and facile integrated biological-cum-photo assisted electrooxidation process for degradation of textile wastewater. Water Res 93:230–241. https://doi.org/10.1016/j.watres.2016.02.04110.1016/j.watres.2016.02.041 ↗
3. Bailey WF, Bobbitt JM, Wiberg KB (2007) Mechanism of the oxidation of alcohols by oxoammonium cations. J Org Chem 72:4504–4509. https://doi.org/10.1021/jo070461410.1021/jo0704614 ↗
4. Biliuta G, Fras L, Drobota M, Persin Z, Kreze T, Ribitsch V (2013) Comparison study of TEMPO and phthalimide-N-oxyl (PINO) radicals on oxidation efficiency toward cellulose. Carbohydr Polym 91:502–507. https://doi.org/10.1016/j.carbpol.2012.08.04710.1016/j.carbpol.2012.08.047 ↗
5. Bobbitt JM, Eddy NA, Cady CX, Jin J, Gascon JA, Zakrzewski J, Morton MD (2017) Preparation of Some Homologous TEMPO Nitroxides and Oxoammonium Salts; Notes on the NMR Spectroscopy of Nitroxide Free Radicals; Observed Radical Nature of Oxoammonium Salt Solutions Containing Trace Amounts of Corresponding Nitroxides in an Equilibrium R. J Org Chem 82:9279–9290. https://doi.org/10.1021/acs.joc.7b0084610.1021/acs.joc.7b00846 ↗
6. Bu X, Li Y, Zhen X, Wang J, Zhang X, Bian N, Chan H, Liu K, Zhang F, Pei J (2019) Effect of carboxyl content on the physicochemical properties and intramolecular water distribution of 6-carboxyl chitooligomer prepared by laccase-TEMPO. J Appl Polym Sci 136:1–9. https://doi.org/10.1002/app.4750910.1002/app.47509 ↗
7. Chen S, Yue N, Cui M, Penkova A, Huang R, Qi W, He Z, Su R (2022) Integrating direct reuse and extraction recovery of TEMPO for production of cellulose nanofibrils. Carbohydr Polym 294:119803. https://doi.org/10.1016/j.carbpol.2022.11980310.1016/j.carbpol.2022.119803 ↗
8. Chen X, Li H, Liu J (2012) The dissolution enthalpy and entropy of KF in aprotic polar solvents. Russ J Phys Chem A 86:1943–1946. https://doi.org/10.1134/S003602441213025010.1134/S0036024412130250 ↗
9. Cheng F, He J, Yan T, Liu C, Wei X, Li J, Huang Y (2016) Antibacterial and hemostatic composite gauze of N, O-carboxymethyl chitosan/oxidized regenerated cellulose. RSC Adv 6:94429–94436. https://doi.org/10.1039/c6ra15983d10.1039/c6ra15983d ↗
10. Cheng W, He J, Wu Y, Song C, Xie S, Huang Y, Fu B (2013) Preparation and characterization of oxidized regenerated cellulose film for hemostasis and the effect of blood on its surface. Cellulose 20:2547–2558. https://doi.org/10.1007/s10570-013-0005-510.1007/s10570-013-0005-5 ↗
11. Coseri S, Biliuta G (2012) Bromide-free oxidizing system for carboxylic moiety formation in cellulose chain. Carbohydr Polym 90:1415–1419. https://doi.org/10.1016/j.carbpol.2012.07.00910.1016/j.carbpol.2012.07.009 ↗
12. Coseri S, Biliuta G, Simionescu BC, Kleinschek KS, Ribitsch V, Harabagiu V (2013) Oxidized cellulose - Survey of the most recent achievements. Carbohydr Polym 93:207–215. https://doi.org/10.1016/j.carbpol.2012.03.08610.1016/j.carbpol.2012.03.086 ↗
13. D’Acierno F, Hamad WY, Michal CA, Maclachlan MJ (2020) Thermal Degradation of Cellulose Filaments and Nanocrystals. Biomacromol 21:3374–3386. https://doi.org/10.1021/acs.biomac.0c0080510.1021/acs.biomac.0c00805 ↗
14. Da Silva PD, Montanari S, Vignon MR (2003) TEMPO-mediated oxidation of cellulose III. Biomacromol 4:1417–1425. https://doi.org/10.1021/bm034144s10.1021/bm034144s ↗
15. Demartini JD, Pattathil S, Miller JS, Li H, Hahn MG, Wyman CE (2013) Investigating plant cell wall components that affect biomass recalcitrance in poplar and switchgrass. Energy Environ Sci 6:898–909. https://doi.org/10.1039/c3ee23801f10.1039/c3ee23801f ↗
16. Follain N, Marais MF, Montanari S, Vignon MR (2010) Coupling onto surface carboxylated cellulose nanocrystals. Polymer (Guildf) 51:5332–5344. https://doi.org/10.1016/j.polymer.2010.09.00110.1016/j.polymer.2010.09.001 ↗
17. Follain N, Montanari S, Jeacomine I, Gambarelli S, Vignon MR (2008) Coupling of amines with polyglucuronic acid: Evidence for amide bond formation. Carbohydr Polym 74:333–343. https://doi.org/10.1016/j.carbpol.2008.02.01610.1016/j.carbpol.2008.02.016 ↗
18. Fras L, Johansson LS, Stenius P, Laine J, Stana-Kleinschek K, Ribitsch V (2005) Analysis of the oxidation of cellulose fibres by titration and XPS. Colloids Surfaces A Physicochem Eng Asp 260:101–108. https://doi.org/10.1016/j.colsurfa.2005.01.03510.1016/j.colsurfa.2005.01.035 ↗
19. Fu X, Zhang F, Dong C, Zhu W, Xiong K, Pang Z (2021) Efficient homogeneous TEMPO-mediated oxidation of cellulose in lithium bromide hydrates. Int J Biol Macromol 191:637–645. https://doi.org/10.1016/j.ijbiomac.2021.09.10410.1016/j.ijbiomac.2021.09.104 ↗
20. Fukuzumi H, Saito T, Okita Y, Isogai A (2010) Thermal stabilization of TEMPO-oxidized cellulose. Polym Degrad Stab 95:1502–1508. https://doi.org/10.1016/j.polymdegradstab.2010.06.01510.1016/j.polymdegradstab.2010.06.015 ↗
21. Furukawa K, Shibuya M, Yamamoto Y (2015) Chemoselective catalytic oxidation of 1,2-diols to α-hydroxy acids controlled by TEMPO-ClO2 charge-transfer complex. Org Lett 17:2282–2285. https://doi.org/10.1021/acs.orglett.5b0100310.1021/acs.orglett.5b01003 ↗
22. Ganiev IM, Timerghazin QK, Khalizov AF, Shereshovets VV, Tolstikov GA (2001) Complex of chlorine dioxide with TEMPO and its conversion into oxoammonium salt. J Phys Org Chem 14:38–42. https://doi.org/10.1002/1099-1395(200101)14:1%3c38::AID-POC334%3e3.0.CO;2-Z10.1002/1099-1395(200101)14:1<38::AID-POC334>3.0.CO;2-Z ↗
23. Ganiev IM, Timerghazin QK, Khalizov AF (1999) Complexes of chlorine dioxide with nitroxyl radicals. Tetrahedron Lett 40:4737–4740. https://doi.org/10.1016/S0040-4039(99)00837-010.1016/S0040-4039(99)00837-0 ↗
24. Gao X, Chen K, Zhang H, Peng L (2014a) The preparation of soluble cellouronic acid sodium salt by 4-acetamide-TEMPO mediated oxidation of ultrasound-pretreated parenchyma cellulose from bagasse pith. Arch Acoust 39:267–275. https://doi.org/10.2478/aoa-2014-003110.2478/aoa-2014-0031 ↗
25. Gao X, Chen KL, Zhang H, Peng LC, Liu QX (2014b) Isolation and characterization of cellulose obtained from bagasse pith by oxygen-containing agents. BioResources 9:4094–4107. https://doi.org/10.15376/biores.9.3.4094-410710.15376/biores.9.3.4094-4107 ↗
26. Gao X, Li M, Zhang H, Tang X, Chen K (2021) Fabrication of regenerated cellulose films by DMAc dissolution using parenchyma cells via low-temperature pulping from Yunnan-endemic bamboos. Ind Crops Prod 160:113116. https://doi.org/10.1016/j.indcrop.2020.11311610.1016/j.indcrop.2020.113116 ↗
27. Gu H, Gao X, Zhang H, Chen K, Peng L (2020) Fabrication and characterization of cellulose nanoparticles from maize stalk pith via ultrasonic-mediated cationic etherification. Ultrason Sonochem 66:104932. https://doi.org/10.1016/j.ultsonch.2019.10493210.1016/j.ultsonch.2019.104932 ↗
28. Habibi Y, Chanzy H, Vignon MR (2006) TEMPO-mediated surface oxidation of cellulose whiskers. Cellulose 13:679–687. https://doi.org/10.1007/s10570-006-9075-y10.1007/s10570-006-9075-y ↗
29. Han Q, Gao X, Zhang H, Chen K, Peng L, Jia Q (2019) Preparation and comparative assessment of regenerated cellulose films from corn (Zea mays)stalk pulp fines in DMAc/LiCl solution. Carbohydr Polym 218:315–323. https://doi.org/10.1016/j.carbpol.2019.04.08310.1016/j.carbpol.2019.04.083 ↗
30. Hao R, Mao X, Qian Z, Zhao Y, Wang L, Yuan B, Wang K, Liu Z, Qi M, Crittenden J (2019) Simultaneous Removal of SO2 and NO Using a Novel Method of Ultraviolet Irradiating Chlorite-Ammonia Complex. Environ Sci Technol 53:9014–9023. https://doi.org/10.1021/acs.est.8b0695010.1021/acs.est.8b06950 ↗
31. Heux L, Dinand E, Vignon MR (1999) Structural aspects in ultrathin cellulose microfibrils followed by 13C CP-MAS NMR. Carbohydr Polym 40:115–124. https://doi.org/10.1016/S0144-8617(99)00051-X10.1016/S0144-8617(99)00051-X ↗
32. Hirota M, Tamura N, Saito T, Isogai A (2012) Cellulose II nanoelements prepared from fully mercerized, partially mercerized and regenerated celluloses by 4-acetamido-TEMPO/NaClO/NaClO2 oxidation. Cellulose 19:435–442. https://doi.org/10.1007/s10570-011-9642-810.1007/s10570-011-9642-8 ↗
33. Hosoya T, Bacher M, Potthast A, Elder T, Rosenau T (2018) Insights into degradation pathways of oxidized anhydroglucose units in cellulose by β-alkoxy-elimination: a combined theoretical and experimental approach. Cellulose 25:3797–3814. https://doi.org/10.1007/s10570-018-1835-y10.1007/s10570-018-1835-y ↗
34. Hua X, Kaliaguine S, Kokta BV, Adnot A (1993) Surface analysis of explosion pulps by ESCA Part 1. Carbon (1s) spectra and oxygen-to-carbon ratios. Wood Sci Technol 27:449–459. https://doi.org/10.1007/BF0019386810.1007/BF00193868 ↗
35. Isogai A, Zhou Y (2019) Diverse nanocelluloses prepared from TEMPO-oxidized wood cellulose fibers: Nanonetworks, nanofibers, and nanocrystals. Curr Opin Solid State Mater Sci 23:101–106. https://doi.org/10.1016/j.cossms.2019.01.00110.1016/j.cossms.2019.01.001 ↗
36. Iwamoto S, Kai W, Isogai T, Saito T, Isogai A, Iwata T (2010) Comparison study of TEMPO-analogous compounds on oxidation efficiency of wood cellulose for preparation of cellulose nanofibrils. Polym Degrad Stab 95:1394–1398. https://doi.org/10.1016/j.polymdegradstab.2010.01.01710.1016/j.polymdegradstab.2010.01.017 ↗
37. Jo YK, Heo SJ, Peredo AP, Mauck RL, Dodge GR, Lee D (2021) Stretch-responsive adhesive microcapsules for strain-regulated antibiotic release from fabric wound dressings. Biomater Sci 9:5136–5143. https://doi.org/10.1039/d1bm00628b10.1039/d1bm00628b ↗
38. Joncourt MJ, Froment P, Lachenal D (1998) Formation of radical species during ClO2 delignification. J Wood Chem Technol 18:159–170. https://doi.org/10.1080/0277381980934957410.1080/02773819809349574 ↗
39. Kato Y, Matsuo R, Isogai A (2003) Oxidation process of water-soluble starch in TEMPO-mediated system. Carbohydr Polym 51:69–75. https://doi.org/10.1016/S0144-8617(02)00159-510.1016/S0144-8617(02)00159-5 ↗
40. Kong X, Wu Z, Ren Z, Guo K, Hou S, Hua Z, Li X, Fang J (2018) Degradation of lipid regulators by the UV/chlorine process: Radical mechanisms, chlorine oxide radical (ClO·)-mediated transformation pathways and toxicity changes. Water Res 137:242–250. https://doi.org/10.1016/j.watres.2018.03.00410.1016/j.watres.2018.03.004 ↗
41. Korntner P, Hosoya T, Dietz T, Eibinger K, Reiter H, Spitzbart M, Borgards A (2015) Chromophores in lignin-free cellulosic materials belong to three compound classes. Chromophores in cellulosics. XII Cellulose 22:1053–1062. https://doi.org/10.1007/s10570-015-0566-610.1007/s10570-015-0566-6 ↗
42. Kushch O, Hordieieva I, Novikova K, Litvinov Y, Kompanets M, Shendrik A, Opeida I (2020) Kinetics of N-oxyl Radicals’ Decay. J Org Chem 85:7112–7124. https://doi.org/10.1021/acs.joc.0c0050610.1021/acs.joc.0c00506 ↗
43. Lei Y, Lei X, Westerhoff P, Zhang X, Yang X (2021) Reactivity of Chlorine Radicals (Cl· and Cl2·-) with Dissolved Organic Matter and the Formation of Chlorinated Byproducts. Environ Sci Technol 55:689–699. https://doi.org/10.1021/acs.est.0c0559610.1021/acs.est.0c05596 ↗
44. Levanič J, Šenk VP, Nadrah P, Oven P, Haapala A (2020) Analyzing TEMPO-Oxidized Cellulose Fiber Morphology: New Insights into Optimization of the Oxidation Process and Nanocellulose Dispersion Quality. ACS Sustain Chem Eng 8:17752–17762. https://doi.org/10.1021/acssuschemeng.0c0598910.1021/acssuschemeng.0c05989 ↗
45. Li Q, Liu G hua, Chen S, Qi L, Wang H (2023) Clarifying the contributor of ammonia oxidation in chlorine-mediated electrochemical process. Chem Eng J 473:. https://doi.org/10.1016/j.cej.2023.14512010.1016/j.cej.2023.145120 ↗
46. Li X, Li H, Ling Z, Xu D, You T, Wu Y, Xu F (2020) Room-Temperature Superbase-Derived Ionic Liquids with Facile Synthesis and Low Viscosity: Powerful Solvents for Cellulose Dissolution by Destroying the Cellulose Aggregate Structure. Macromolecules 53:3284–3295. https://doi.org/10.1021/acs.macromol.0c0059210.1021/acs.macromol.0c00592 ↗
47. Liu B, Niu W, Hu X, Liu F, Jiang J, Wang H, Wang S (2022) Enhanced oxidative activation of chlorine dioxide by divalent manganese ion for efficient removal of PAHs in industrial soil. Chem Eng J 434:134631. https://doi.org/10.1016/j.cej.2022.13463110.1016/j.cej.2022.134631 ↗
48. Liu J, Korpinen R, Mikkonen KS, Liu J, Korpinen R, Mikkonen KS, Xu C (2014) Nanofibrillated cellulose originated from birch sawdust after sequential extractions: A promising polymeric material from waste to films. Cellulose 21:2587–2598. https://doi.org/10.1007/s10570-014-0321-410.1007/s10570-014-0321-4 ↗
49. Marcon J, Mortha G, Marlin N, Molton F, Duboc C, Burnet A (2017) New insights into the decomposition mechanism of chlorine dioxide at alkaline pH. Holzforschung 71:599–610. https://doi.org/10.1515/hf-2016-014710.1515/hf-2016-0147 ↗
50. Montanari S, Roumani M, Heux L, Vignon MR (2005) Topochemistry of carboxylated cellulose nanocrystals resulting from TEMPO-mediated oxidation. Macromolecules 38:1665–1671. https://doi.org/10.1021/ma048396c10.1021/ma048396c ↗
51. Moon RJ, Martini A, Nairn J, Simonsen J, Youngblood J (2011) Cellulose nanomaterials review: Structure, properties and nanocomposites. Chem. Soc. Rev. 40: 3941–3994. http://pubs.rsc.orghttps://doi.org/10.1039/C0CS00108B10.1039/C0CS00108B ↗
52. Ozawa T, Miura Y, Ueda JI (1996) Oxidation of spin-traps by chlorine dioxide (ClO2) radical in aqueous solutions: First ESR evidence of formation of new nitroxide radicals. Free Radic Biol Med 20:837–841. https://doi.org/10.1016/0891-5849(95)02092-610.1016/0891-5849(95)02092-6 ↗
53. Pääkkönen T, Pönni R, Dou J, Nuopponen M, Vuorinen T (2017) Activation of TEMPO by ClO2 for oxidation of cellulose by hypochlorite—Fundamental and practical aspects of the catalytic system. Carbohydr Polym 174:524–530. https://doi.org/10.1016/j.carbpol.2017.06.11710.1016/j.carbpol.2017.06.117 ↗
54. Potthast A, Rosenau T, Buchner R (2002) Cellulose in lithium chloride/N, N-dimethylacetamide, optimisation of a dissolution method using paper substrates and stability of the solutions. Polymer (Guildf) 44:4117–4126. https://doi.org/10.1016/S0032-3861(03)00398-710.1016/S0032-3861(03)00398-7 ↗
55. Patel I, Opietnik M, Böhmdorfer S, Becker M, Potthast A, Saito T, Isogai A, Rosenau T (2010) Side reactions of 4-acetamide-TEMPO as the catalyst in cellulose oxidation systems. Holzforschung 64:549–554. https://doi.org/10.1515/HF.2010.07210.1515/HF.2010.072 ↗
56. Peng J, Yin R, Yang X, Shang C (2022) A Novel UVA/ClO2 Advanced Oxidation Process for the Degradation of Micropollutants in Water. Environ Sci Technol 56:1257–1266. https://doi.org/10.1021/acs.est.1c0513310.1021/acs.est.1c05133 ↗
57. Ran Y, Qingmin C, Maorun F (2019) Chlorine Dioxide Generation Method and Its Action Mechanism for Removing Harmful Substances and Maintaining Quality Attributes of Agricultural Products. Food Bioprocess Technol 12:1110–1122. https://doi.org/10.1007/s11947-019-02279-x10.1007/s11947-019-02279-x ↗
58. Saito T, Hirota M, Tamura N, Isogai A (2010) Oxidation of bleached wood pulp by TEMPO/NaClO/NaClO2 system: Effect of the oxidation conditions on carboxylate content and degree of polymerization. J Wood Sci 56:227–232. https://doi.org/10.1007/s10086-009-1092-710.1007/s10086-009-1092-7 ↗
59. Saito T, Shibata I, Isogai A, Suguri N, Sumikawa N (2005) Distribution of carboxylate groups introduced into cotton linters by the TEMPO-mediated oxidation. Carbohydr Polym 61:414–419. https://doi.org/10.1016/j.carbpol.2005.05.01410.1016/j.carbpol.2005.05.014 ↗
60. Salmén L, Bergström E (2009) Cellulose structural arrangement in relation to spectral changes in tensile loading FTIR. Cellulose 16:975–982. https://doi.org/10.1007/s10570-009-9331-z10.1007/s10570-009-9331-z ↗
61. Shao C, Shi K, Hua Q, Zhang L, Dai Y, You W, Liu Y, Li C, Zhang C (2018) Mechanism for the depolymerization of cellulose under alkaline conditions. J Mol Model 24:. https://doi.org/10.1007/s00894-018-3654-310.1007/s00894-018-3654-3 ↗
62. Shibata I, Isogai A (2003) Depolymerization of cellouronic acid during TEMPO-mediated oxidation. Cellulose 10:151–158. https://doi.org/10.1023/A:102405151402610.1023/A:1024051514026 ↗
63. Smith GN (2018) Proton transfer in nonpolar solvents: An approach to generate electrolytes in aprotic media. Phys Chem Chem Phys 20:18919–18923. https://doi.org/10.1039/c8cp02349b10.1039/c8cp02349b ↗
64. Su R, Huang L, Li N, Li L, Jin B, Zhou W, Gao B, Yue Q, Li Q (2021) Chlorine dioxide radicals triggered by chlorite under visible-light irradiation for enhanced degradation and detoxification of norfloxacin antibiotic: Radical mechanism and toxicity evaluation. Chem Eng J 414:108–113. https://doi.org/10.1016/j.cej.2021.12876810.1016/j.cej.2021.128768 ↗
65. Tan T, Zhou J, Gao X, Tang X, Zhang H (2021) Synthesis, characterization and water-absorption behavior of tartaric acid-modified cellulose gel fromcorn stalk pith. Ind Crops Prod 169:113641. https://doi.org/10.1016/j.indcrop.2021.11364110.1016/j.indcrop.2021.113641 ↗
66. Tanaka R, Saito T, Isogai A (2012) Cellulose nanofibrils prepared from softwood cellulose by TEMPO/NaClO/NaClO2 systems in water at pH 4.8 or 6.8. Int J Biol Macromol 51:228–234. https://doi.org/10.1016/j.ijbiomac.2012.05.01610.1016/j.ijbiomac.2012.05.016 ↗
67. Tang X, Liu G, Zhang H, Gao X, Li M, Zhang S (2021) Facile preparation of all-cellulose composites from softwood, hardwood, and agricultural straw cellulose by a simple route of partial dissolution. Carbohydr Polym 256:117591. https://doi.org/10.1016/j.carbpol.2020.11759110.1016/j.carbpol.2020.117591 ↗
68. Tang Z, Li W, Lin X, Xiao H, Miao Q, Huang L, Chen L, Wu H (2017) TEMPO-Oxidized cellulose with high degree of oxidation. Polymers (Basel) 9:3–4. https://doi.org/10.3390/polym909042110.3390/polym9090421 ↗
69. Tzanavaras PD, Themelis DG, Kika FS (2007) Review of Analytical Methods for the Determination of Chlorine Dioxide 5:1–12. https://doi.org/10.2478/s11532-006-0054-910.2478/s11532-006-0054-9 ↗
70. Wagner K, Friese T, Schulz S, Ulbig P (1998) Solubilities of sodium chloride in organic and aqueous-organic solvent mixtures. J Chem Eng Data 43:871–875. https://doi.org/10.1021/je980051010.1021/je9800510 ↗
71. Wang L, Li K, Copenhaver K, MacKay S, Lamm M, Zhao X, Dixon B, Wang J, Han Y, Neivandt D, Johnson DA, Walker CC, Ozcan S, Gardner DJ (2021) Review on Nonconventional Fibrillation Methods of Producing Cellulose Nanofibrils and Their Applications. Biomacromol 22:4037–4059. https://doi.org/10.1021/acs.biomac.1c0064010.1021/acs.biomac.1c00640 ↗
72. Wu Y, Wang F (2019) Study of the degradation mechanisms of oxidized Cellulose-Derivative hemostatic agent by using model compound. J Biomater Sci Polym Ed 30:580–591. https://doi.org/10.1080/09205063.2019.159279710.1080/09205063.2019.1592797 ↗
73. Wu YD, He JM, Huang YD, Wang FW, Tang F (2012) Oxidation of regenerated cellulose with nitrogen dioxide/carbon tetrachloride. Fibers Polym 13:576–581. https://doi.org/10.1007/s12221-012-0576-z10.1007/s12221-012-0576-z ↗
74. Yao W, Weng Y, Catchmark JM (2020) Improved cellulose X-ray diffraction analysis using Fourier series modeling. Cellulose 27:5563–5579. https://doi.org/10.1007/s10570-020-03177-810.1007/s10570-020-03177-8 ↗
75. Yan JK, Pei JJ, Le MH, Bin WZ (2015) Effects of ultrasound on molecular properties, structure, chain conformation and degradation kinetics of carboxylic curdlan. Carbohydr Polym 121:64–70. https://doi.org/10.1016/j.carbpol.2014.11.06610.1016/j.carbpol.2014.11.066 ↗
76. Yan Z, Dai Z, Zheng W, Lei Z, Qiu J, Kuang W, Huang W, Feng C (2021) Facile ammonium oxidation to nitrogen gas in acid wastewater by in situ photogenerated chlorine radicals. Water Res 205:. https://doi.org/10.1016/j.watres.2021.11767810.1016/j.watres.2021.117678 ↗
77. Yang H, Benatti MR, Karve RA, Fox A, Meilan R, Carpita NC, McCann MC (2020) Rhamnogalacturonan-I is a determinant of cell–cell adhesion in poplar wood. Plant Biotechnol J 18:1027–1040. https://doi.org/10.1111/pbi.1327110.1111/pbi.13271 ↗
78. Yang H, Yan R, Chen H (2007) Characteristics of hemicellulose, cellulose and lignin pyrolysis. Fuel 86:1781–1788. https://doi.org/10.1016/j.fuel.2006.12.01310.1016/j.fuel.2006.12.013 ↗
79. Ye D, Lei X, Li T, Cheng Q, Chang C, Hu L, Zhang L (2019) Ultrahigh Tough, Super Clear, and Highly Anisotropic Nanofiber-Structured Regenerated Cellulose Films. ACS Nano 13:4843–4853. https://doi.org/10.1021/acsnano.9b0208110.1021/acsnano.9b02081 ↗
80. Yin L, Zhang J, Yao J, Li H (2018) A Designed TEMPO-derivate Catalyst with Switchable Signals of EPR and Photoluminescence: Application in the Mechanism of Alcohol Oxidation. ChemCatChem 10:3513–3519. https://doi.org/10.1002/cctc.20180034510.1002/cctc.201800345 ↗
81. Yin R, Blatchley ER, Shang C (2020) UV Photolysis of Mono- And Dichloramine Using UV-LEDs as Radiation Sources: Photodecay Rates and Radical Concentrations. Environ Sci Technol 54:8420–8429. https://doi.org/10.1021/acs.est.0c0163910.1021/acs.est.0c01639 ↗
82. Yuan H, Chen L, Hong FF (2020) A Biodegradable Antibacterial Nanocomposite Based on Oxidized Bacterial Nanocellulose for Rapid Hemostasis and Wound Healing. ACS Appl Mater Interfaces 12:3382–3392. https://doi.org/10.1021/acsami.9b1773210.1021/acsami.9b17732 ↗
83. Zhang H, Chen K, Gao X, Han Q, Peng L (2019a) Improved thermal stability of regenerated cellulose films from corn (Zea mays)stalk pith using facile preparation with low-concentration zinc chloride dissolving. Carbohydr Polym 217:190–198. https://doi.org/10.1016/j.carbpol.2018.10.10710.1016/j.carbpol.2018.10.107 ↗
84. Zhang H, Gao X, Chen KL, Liu QX (2016) Maximizing the yield of water-soluble cellouronic acid sodium salt with high carboxyl content by 4-acetamide-TEMPO mediated oxidation of parenchyma cellulose from bagasse pith. Iran Polym J 25:465–474. https://doi.org/10.1007/s13726-016-0438-410.1007/s13726-016-0438-4 ↗
85. Zhang H, Tang X, Gao X, Chen K (2019b) Fabrication and comparative evaluation of regenerated cellulose films using pulp fines and pith from corn stalk in DMAc/LiCl solvent system. BioResources 14:6421–6432. https://doi.org/10.15376/biores.14.3.6421-643210.15376/biores.14.3.6421-6432 ↗
86. Zhang J, Liu J, Liu R (2015) Effects of pyrolysis temperature and heating time on biochar obtained from the pyrolysis of straw and lignosulfonate. Bioresour Technol 176:288–291. https://doi.org/10.1016/j.biortech.2014.11.01110.1016/j.biortech.2014.11.011 ↗
87. Zhang K, Fischer S, Geissler A, Brendler E (2012) Analysis of carboxylate groups in oxidized never-dried cellulose II catalyzed by TEMPO and 4-acetamide-TEMPO. Carbohydr Polym 87:894–900. https://doi.org/10.1016/j.carbpol.2011.08.09010.1016/j.carbpol.2011.08.090 ↗
88. Zhang S, Li J, Chen S, Zhang X, Ma J, He J (2020) Oxidized cellulose-based hemostatic materials. Carbohydr Polym 230:115585. https://doi.org/10.1016/j.carbpol.2019.11558510.1016/j.carbpol.2019.115585 ↗
89. Zhang S, Shan S, Zhang H, Gao X, Tang X, Chen K (2022a) Antimicrobial cellulose hydrogels preparation with RIF loading from bamboo parenchyma cells: A green approach towards wound healing. Int J Biol Macromol 203:1–9. https://doi.org/10.1016/j.ijbiomac.2022.01.04610.1016/j.ijbiomac.2022.01.046 ↗
90. Zhang X, Guo F, Yu Z, Cao M, Wang H, Yang R, Yu Y (2022b) Why Do Bamboo Parenchyma Cells Show Higher Nanofibrillation Efficiency than Fibers: An Investigation on Their Hierarchical Cell Wall Structure. Biomacromol 23:4053–4062. https://doi.org/10.1021/acs.biomac.2c0022410.1021/acs.biomac.2c00224 ↗
91. Zhang X, Ren P, Li W, Lei Y, Yang X, Blatchley ER (2019c) Synergistic removal of ammonium by monochloramine photolysis. Water Res 152:226–233. https://doi.org/10.1016/j.watres.2018.12.06510.1016/j.watres.2018.12.065 ↗
92. Zhang Y, Li J, Bai J, Li L, Chen S, Zhou T, Wang J, Xia L, Xu Q, Xu Q, Zhou B (2019d) Extremely Efficient Decomposition of Ammonia N to N2 Using ClO· from Reactions of HO· and HOCl Generated in Situ on a Novel Bifacial Photoelectroanode. Environ Sci Technol 53:6945–6953. https://doi.org/10.1021/acs.est.9b0095910.1021/acs.est.9b00959 ↗
93. Zhao J, He X, Wang Y, Zhang W, Zhang X, Zhang X, Deng Y, Lu C (2014) Reinforcement of all-cellulose nanocomposite films using native cellulose nanofibrils. Carbohydr Polym 104:143–150. https://doi.org/10.1016/j.carbpol.2014.01.00710.1016/j.carbpol.2014.01.007 ↗
94. Zheng W, Zhu L, Liang S, Ye J, Yang X, Lei Z, Yan Z, Li Y, Wei C, Feng C (2020) Discovering the Importance of ClO· in a Coupled Electrochemical System for the Simultaneous Removal of Carbon and Nitrogen from Secondary Coking Wastewater Effluent. Environ Sci Technol 54:9015–9024. https://doi.org/10.1021/acs.est.9b0770410.1021/acs.est.9b07704 ↗
95. Zhou P, Zhu P, Chen G, Liu Y, Kuang Y, Liu Y, Fang Z (2018) A study on the transmission haze and mechanical properties of highly transparent paper with different fiber species. Cellulose 25:2051–2061. https://doi.org/10.1007/s10570-018-1663-010.1007/s10570-018-1663-0 ↗