Abstract
Recently, polysaccharides have attracted tremendous interest as potential candidates to develop promising high-energy dense polymers through the chemical functionalization of their structures. Therefore, chitosan nitrate (CSN), as an energetic polysaccharide was fabricated by nitration of chitosan (CS) derived from shrimp Parapenaeus longirostris shells. The physicochemical, structural, and thermal features of the designed energetic CSN and its precursors were elucidated by density measurements, elemental analysis, FTIR, SEM, TGA, and DSC experiments. The mechanical sensitivities and calorific energy of the produced CSN were also determined and its theoretical detonation performance was computed using the EXPLO5 V6.04 software. The results demonstrated the efficiency of the performed method to produce the desired CSN with attractive characteristics such as a density of 1.701 g/cm3, nitration content of 16.55%, impact sensitivity of 15 J, heat of combustion of 10,610 J/g, detonation velocity of 7764 m/s, and specific impulse of 242 s, which are better than those of commonly used nitrocellulose (NC). Besides that, new energetic CSN/NC polymer blends with different mass ratios (CSN:NC (wt%) = 25:75, 50:50, and 75:25) were elaborated and characterized in terms of their chemical structure, thermal behavior, and energetic performance. Experimental findings highlighted the attractive properties of the developed CSN/NC blends, providing evidence for the excellent synergistic effect between energetic CSN and NC polymers. Finally, this work established that shrimp shells wastes could serve as valuable biomass for the production of promising insensitive and high-energy dense polysaccharide, which is expected to be widely employed in the next generation of energetic formulations.
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References
Ahmad A, Mubarak N, Naseem K, Tabassum H, Rizwan M, Najda A, Kashif M, Bin-Jumah M, Hussain A, Shaheen A (2020) Recent advancement and development of chitin and chitosan-based nanocomposite for drug delivery: critical approach to clinical research. Arab J Chem 13(12):8935–8964
Barbosa HF, Francisco DS, Ferreira AP, Cavalheiro ÉT (2019) A new look towards the thermal decomposition of chitins and chitosans with different degrees of deacetylation by coupled TG-FTIR. Carbohydr Polym 225:115232
Begum S, Yuhana NY, Saleh NM, Kamarudin NHN, Sulong AB (2021) Review of chitosan composite as a heavy metal adsorbent: material preparation and properties. Carbohydr Polym 259:117613
Ben Seghir B, Benhamza M (2017) Preparation, optimization and characterization of chitosan polymer from shrimp shells. J Food Meas Charact 11(3):1137–1147
Benhabiles M, Salah R, Lounici H, Drouiche N, Goosen M, Mameri N (2012) Antibacterial activity of chitin, chitosan and its oligomers prepared from shrimp shell waste. Food Hydrocoll 29(1):48–56
Benhammada A, Trache D, Kesraoui M, Chelouche S (2020) Hydrothermal synthesis of hematite nanoparticles decorated on carbon mesospheres and their synergetic action on the thermal decomposition of nitrocellulose. Nanomaterials 10(5):968
Betzler FM, Hartdegen VA, Klapötke TM, Sproll SM (2016) A new energetic binder: glycidyl nitramine polymer. Cent Eur J Energ Mater 13(2):289–300
Bhardwaj S, Bhardwaj NK, Negi YS (2021) Surface coating of chitosan of different degree of acetylation on non surface sized writing and printing grade paper. Carbohydr Polym 269:117674
Chalghoum F, Trache D, Benziane M, Chelouche S (2022) Effect of complex metal hydride on the thermal decomposition behavior of AP/HTPB-based aluminized solid rocket propellant. J Therm Anal Calorim 147(20):11507–11534
Chen F, Wang Y, Zhang Q (2022) Recent advances in the synthesis and properties of energetic plasticizers. New J Chem 46(43):20540–20553
da Silva Lucas AJ, Oreste EQ, Costa HLG, Lopez HM, Saad CDM, Prentice C (2021) Extraction, physicochemical characterization, and morphological properties of chitin and chitosan from cuticles of edible insects. Food Chem 343:128550
Doğdu SA, Turan C, Depci T (2021) Extraction and characterization of chitin and Chitosan from invasive alien swimming crab Charybdis longicollis. Nat Eng Sci 6(2):96–101
Domszy JG, Roberts GA (1985) Evaluation of infrared spectroscopic techniques for analysing chitosan. Die Makromol Chem Macromol Chem Phys 186(8):1671–1677
Dou J, Xu M, Tan B, Lu X, Mo H, Wang B, Liu N (2022) Research progress of nitrate ester binders. Fire Phys Chem 3(1):54–77
El Knidri H, Belaabed R, Addaou A, Laajeb A, Lahsini A (2018) Extraction, chemical modification and characterization of chitin and chitosan. Int J Biol Macromol 120:1181–1189
Elbasuney S, Fahd A, Mostafa HE (2017) Combustion characteristics of extruded double base propellant based on ammonium perchlorate/aluminum binary mixture. Fuel 208:296–304
Flórez M, Guerra-Rodríguez E, Cazón P, Vázquez M (2022) Chitosan for food packaging: recent advances in active and intelligent films. Food Hydrocoll 124:107328
Francis AO, Zaini MAA, Muhammad IM, Abdulsalam S, El-Nafaty UAJBC, Biorefinery (2021) Physicochemical modification of chitosan adsorbent: a perspective. Biomass Convers Biorefin. https://doi.org/10.1007/s13399-021-01599-3
Guo M, Ma Z, He L, He W, Wang Y (2017) Effect of varied proportion of GAP-ETPE/NC as binder on thermal decomposition behaviors, stability and mechanical properties of nitramine propellants. J Therm Anal Calorim 130(2):909–918
Huet G, Hadad C, González-Domínguez JM, Courty M, Jamali A, Cailleu D, van Nhien AN (2021) IL versus DES: impact on chitin pretreatment to afford high quality and highly functionalizable chitosan. Carbohydr Polym 269:118332
Jha PK, Halada GP, McLennan SM (2013) Electrochemical synthesis of nitro-chitosan and its performance in chromium removal. Coatings 3(3):140–152
Joseph SM, Krishnamoorthy S, Paranthaman R, Moses J, Anandharamakrishnan C (2021) A review on source-specific chemistry, functionality, and applications of chitin and chitosan. Carbohydr Polym Technol Appl 2:100036
Kasaai MR (2008) A review of several reported procedures to determine the degree of N-acetylation for chitin and chitosan using infrared spectroscopy. Carbohydr Polym 71(4):497–508
Kaya M, Baran T, Mentes A, Asaroglu M, Sezen G, Tozak KO (2014) Extraction and characterization of α-chitin and chitosan from six different aquatic invertebrates. Food Biophys 9(2):145–157
Kumari S, Annamareddy SHK, Abanti S, Rath PK (2017) Physicochemical properties and characterization of chitosan synthesized from fish scales, crab and shrimp shells. Int J Biol Macromol 104:1697–1705
Lavall RL, Assis OB, Campana-Filho SP (2007) β-Chitin from the pens of Loligo sp.: extraction and characterization. Bioresour Technol 98(13):2465–2472
Li C, Li H, Xu K (2020) High-substitute Nitrochitosan used as energetic materials: Preparation and Detonation Properties. Carbohydr Polym 237:116176
Liakos EV, Lazaridou M, Michailidou G, Koumentakou I, Lambropoulou DA, Bikiaris DN, Kyzas GZ (2021) Chitosan adsorbent derivatives for pharmaceuticals removal from effluents: a review. Macromol 1(2):130–154
Liu H, Zhang L (2001) Structure and properties of semiinterpenetrating polymer networks based on polyurethane and nitrochitosan. J Appl Polym Sci 82(12):3109–3117
Luo T, Wang Y, Huang H, Shang F, Song X (2019) An electrospun preparation of the NC/GAP/nano-LLM-105 nanofiber and its properties. Nanomaterials 9(6):854
Luo Q, Hong J, Xu H, Han S, Tan H, Wang Q, Tao J, Ma N, Cheng Y, Su H (2020) Hygroscopicity of amino acids and their effect on the water uptake of ammonium sulfate in the mixed aerosol particles. Sci Total Environ 734:139318
Marei NH, Abd El-Samie E, Salah T, Saad GR, Elwahy AHJIjobm (2016) Isolation and characterization of chitosan from different local insects in Egypt. Int J Biol Macromol 82:871–877
Mezroua A, Hamada RA, Brahmine KS, Abdelaziz A, Tarchoun AF, Boukeciat H, Bekhouche S, Bessa W, Benhammada A, Trache D (2022) Unraveling the role of ammonium perchlorate on the thermal decomposition behavior and kinetics of NC/DEGDN energetic composite. Thermochim Acta 716:179305
Mohan K, Ganesan AR, Muralisankar T, Jayakumar R, Sathishkumar P, Uthayakumar V, Chandirasekar R, Revathi N (2020) Recent insights into the extraction, characterization, and bioactivities of chitin and chitosan from insects. Trends Food Sci Technol 105:17–42
Mohanty AK, Wu F, Mincheva R, Hakkarainen M, Raquez J-M, Mielewski DF, Narayan R, Netravali AN, Misra M (2022) Sustainable polymers. Nat Rev Methods Prim 2(1):1–27
Muñoz-Nuñez C, Cuervo-Rodríguez R, Echeverría C, Fernández-García M, Muñoz-Bonilla A (2022) Synthesis and characterization of thiazolium chitosan derivative with enhanced antimicrobial properties and its use as component of chitosan based films. Carbohydr Polym 302:120438
Muravyev NV, Wozniak DR, Piercey DG (2022) Progress and performance of energetic materials: open dataset, tool, and implications for synthesis. J Mater Chem A 10(20):11054–11073
Nasrollahzadeh M, Sajjadi M, Iravani S, Varma RS (2021) Starch, cellulose, pectin, gum, alginate, chitin and chitosan derived (nano) materials for sustainable water treatment: a review. Carbohydr Polym 251:116986
Negm NA, Hefni HH, Abd-Elaal AA, Badr EA, Abou Kana MT (2020) Advancement on modification of chitosan biopolymer and its potential applications. Int J Biol Macromol 152:681–702
Olaosebikan AO, Kehinde OA, Tolulase OA, Victor EB (2021) Extraction and characterization of chitin and chitosan from callinectes amnicola and penaeus notialis shell wastes. J Chem Eng Mater Sci 12(12):1–30
Pal K, Bharti D, Sarkar P, Anis A, Kim D, Chałas R, Maksymiuk P, Stachurski P, Jarzębski M (2021) Selected applications of chitosan composites. Int J Mol Sci 22(20):10968
Phuong PTD, Trung TS, Stevens WF, Minh NC, Bao HND, Hoa NV (2022) Valorization of heavy waste of modern intensive shrimp farming as a potential source for chitin and chitosan production. Waste Biomass Valoriz 13(2):823–830
Rahman NA, Abu Hanifah S, Mobarak NN, Su’ait MS, Ahmad A, Shyuan LK, Khoon LT (2019) Synthesis and characterizations of o-nitrochitosan based biopolymer electrolyte for electrochemical devices. PLoS ONE 14(2):e0212066
Rashki S, Asgarpour K, Tarrahimofrad H, Hashemipour M, Ebrahimi MS, Fathizadeh H, Khorshidi A, Khan H, Marzhoseyni Z, Salavati-Niasari M (2021) Chitosan-based nanoparticles against bacterial infections. Carbohydr Polym 251:117108
Rasweefali M, Sabu S, Sunooj K, Sasidharan A, Xavier KM (2021) Consequences of chemical deacetylation on physicochemical, structural and functional characteristics of chitosan extracted from deep-sea mud shrimp. Carbohydr Polym Technol Appl 2:100032
Reshmy R, Philip E, Madhavan A, Sirohi R, Pugazhendhi A, Binod P, Awasthi MK, Vivek N, Kumar V, Sindhu R (2022) Lignocellulose in future biorefineries: strategies for cost-effective production of biomaterials and bioenergy. Bioresour Technol 344:126241
Saravana PS, Ho TC, Chae S-J, Cho Y-J, Park J-S, Lee H-J, Chun B-S (2018) Deep eutectic solvent-based extraction and fabrication of chitin films from crustacean waste. Carbohydr Polym 195:622–630
Srinivasan H, Kanayairam V, Ravichandran RJIjobm (2018) Chitin and chitosan preparation from shrimp shells Penaeus monodon and its human ovarian cancer cell line, PA-1. Int J Biol Macromol 107:662–667
Tang Y, Yin Z, Chinnam AK, Staples RJ, Shreeve JnM (2020) A duo and a trio of triazoles as very thermostable and insensitive energetic materials. Inorg Chem 59(23):17766–17774
Tarchoun AF, Trache D, Klapötke TM (2019a) Microcrystalline cellulose from Posidonia oceanica brown algae: extraction and characterization. Int J Biol Macromol 138:837–845
Tarchoun AF, Trache D, Klapötke TM, Derradji M, Bessa W (2019b) Ecofriendly isolation and characterization of microcrystalline cellulose from giant reed using various acidic media. Cellulose 26(13–14):7635–7651
Tarchoun AF, Trache D, Klapötke TM, Belmerabet M, Abdelaziz A, Derradji M, Belgacemi R (2020a) Synthesis, characterization, and thermal decomposition kinetics of nitrogen-rich energetic biopolymers from aminated giant reed cellulosic fibers. Ind Eng Chem Res 59(52):22677–22689
Tarchoun AF, Trache D, Klapötke TM, Krumm B (2020b) New insensitive nitrogen-rich energetic polymers based on amino-functionalized cellulose and microcrystalline cellulose: synthesis and characterization. Fuel 277:118258
Tarchoun AF, Trache D, Klapötke TM, Krumm B, Khimeche K, Mezroua A (2020c) A promising energetic biopolymer based on azide-functionalized microcrystalline cellulose: synthesis and characterization. Carbohydr Polym 249:116820
Tarchoun AF, Trache D, Klapötke TM, Abdelaziz A, Derradji M, Bekhouche S (2021a) Chemical design and characterization of cellulosic derivatives containing high-nitrogen functional groups: towards the next generation of energetic biopolymers. Def Technol 18(4):537–546
Tarchoun AF, Trache D, Klapötke TM, Selmani A, Saada M, Chelouche S, Mezroua A, Abdelaziz A (2021b) New insensitive high-energy dense biopolymers from giant reed cellulosic fibers: their synthesis, characterization, and non-isothermal decomposition kinetics. New J Chem 45(11):5099–5113
Tarchoun AF, Trache D, Abdelaziz A, Harrat A, Boukecha WO, Hamouche MA, Boukeciat H, Dourari M (2022a) Elaboration, characterization and thermal decomposition kinetics of new nanoenergetic composite based on hydrazine 3-Nitro-1, 2, 4-triazol-5-one and nanostructured cellulose nitrate. Molecules 27(20):6945
Tarchoun AF, Trache D, Hamouche MA, Bessa W, Abdelaziz A, Boukeciat H, Bekhouche S, Belmehdi D (2022b) Insights into characteristics and thermokinetic behavior of potential energy-rich polysaccharide based on chitosan. Cellulose 29(15):8085–8101
Tarchoun AF, Trache D, Klapötke TM, Abdelaziz A, Bekhouche S, Boukeciat H, Sahnoun N (2022c) Making progress towards promising energetic cellulosic microcrystals developed from alternative lignocellulosic biomasses. J Energ Mater. https://doi.org/10.1080/07370652.2022.2032484
Tarchoun AF, Trache D, Klapötke TM, Slimani K, Belouettar Be, Abdelaziz A, Bekhouche S, Bessa W (2022d) Valorization of esparto grass cellulosic derivatives for the development of promising energetic azidodeoxy biopolymers: synthesis, characterization and isoconversional thermal kinetic analysis. Propellants Explos Pyrotech 47(3):e202100293
Teli M, Sheikh JJIjobm (2012) Extraction of chitosan from shrimp shells waste and application in antibacterial finishing of bamboo rayon. Int J Biol Macromol 50:1195–12005
Touidjine S, Boulkadid KM, Trache D, Belkhiri S, Mezroua A (2022) Preparation and characterization of polyurethane/nitrocellulose blends as binder for composite solid propellants. Propellants Explos Pyrotech 47(1):e202000340
Trache D, Tarchoun AF (2019) Differentiation of stabilized nitrocellulose during artificial aging: spectroscopy methods coupled with principal component analysis. J Chemom 33(8):e3163
Trung TS, Van Tan N, Van Hoa N, Minh NC, Loc PT, Stevens WF (2020) Improved method for production of chitin and chitosan from shrimp shells. Carbohydr Res 489:107913
Wang Y, Song X, Song D, Liang L, An C, Wang J (2016) Synthesis, thermolysis, and sensitivities of HMX/NC energetic nanocomposites. J Hazard Mater 312:73–83
Wang B, Feng Y, Qi X, Deng M, Tian J, Zhang Q (2018) Designing explosive poly (ionic liquid) s as novel energetic polymers. Chem A Eur J 24(59):15897–15902
Wu Q, Ma Q, Zhang Z, Yang W, Gou S, Huang J, Fan G (2020) Combustion and catalytic performance of metal-free heat-resistant energetic polymeric materials. Chem Eng J 399:125739
Yan Q-L, Cohen A, Chinnam AK, Petrutik N, Shlomovich A, Burstein L, Gozin M (2016) A layered 2D triaminoguanidine–glyoxal polymer and its transition metal complexes as novel insensitive energetic nanomaterials. J Mater Chem A 4(47):18401–18408
Yuan Y, Hong S, Lian H, Zhang K, Liimatainen H (2020) Comparison of acidic deep eutectic solvents in production of chitin nanocrystals. Carbohydr Polym 236:116095
Zhang L, Chen P, Huang J, Yang G, Zheng L (2003) Ways of strengthening biodegradable soy-dreg plastics. J Appl Polym Sci 88(2):422–427
Zhang W, Qin Z, Yi J, Chen S, Xu K (2022) Laser ignition and combustion properties of composite with high-substituted nitrochitosan and nano-Ti powder. Combust Flame 240:112056
Zhao D, Huang W-C, Guo N, Zhang S, Xue C, Mao X (2019) Two-step separation of chitin from shrimp shells using citric acid and deep eutectic solvents with the assistance of microwave. Polymers 11(3):409
Aili D, Arbia W, Adour L (2017) Treatment of colored waters by beads chitosan, extracted from shrimp waste. In: International symposium on materials and sustainable development. Springer, Cham, p 492–505
NATO SA (1999) 4489 (STANAG 4489), explosives. Impact Sensitivity Tests
NATO SA (2002) 4487 (STANAG 4487), explosives. Friction Sensitivity Tests
Sućeska M (2017) EXPLO5 V6. Brodarski Institute: Zagreb, p 04
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Tarchoun, A.F., Trache, D., Hamouche, M.A. et al. Elucidating the characteristics of a promising nitrate ester polysaccharide derived from shrimp shells and its blends with cellulose nitrate. Cellulose 30, 4941–4955 (2023). https://doi.org/10.1007/s10570-023-05200-0
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DOI: https://doi.org/10.1007/s10570-023-05200-0