Abstract
Phenol is the toxicant present in cigarette smoke that causes pulmonary diseases, eyes infection, and even various kinds of cancer. So, in this research, an attempt was done to prepare a suitable absorbent to remove phenol from cigarette smoke. A novel bio-based adsorbent succinylated carboxymethyl starch (S-CMS) was prepared by reacting carboxymethyl starch (CMS) with succinic anhydride (SA) in the presenting of N, N-dimethylformamide (DMF) solvent and pyridine. The structure of the S-CMS was confirmed by spectroscopic techniques including proton nuclear magnetic resonance and Fourier transform infrared. The S-CMS crystallinity and thermal properties were checked by x-ray diffraction and thermogravimetric analysis. The results showed a decrease in thermal properties and crystallinity for S-CMS. The S-CMS were tested as adsorbents for the removal of phenol. The adsorption efficiencies of CMS, S-CMS1, S-CMS2, and S-CMS3 towards phenol were shown to be 0.297 g/g, 0.321 g/g, 0.322 g/g, and 0.324 g/g, respectively.
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Conde-Petit B, Escher F, Nuessli J (2006) Structural features of starch-flavor complexation in food model systems. Trends Food Sci Tech 17:227–235
Xie F, Pollet E, Halley PJ, Avérous L (2013) Starch-based nano-biocomposites. Prog Polym Sci 38:1590–1628
Yang J, Xie F, Wen W, Chen L, Shang X, Liu P (2016) Understanding the structural features of high-amylose maize starch through hydrothermal treatment. Int J Biol Macromol 84:268–274
Haq F, Yu H, Wang L, Teng L, Haroon M, Khan RU et al (2019) Advances in chemical modifications of starches and their applications. Carbohyd Res 476:12–35
Tang Y, Xie F, Zhang D, Zhu M, Liu L, Liu P et al (2015) Physical properties and prebiotic activity of maize starch-based functional films. Starch-Starke 67:124–131
Bie P, Liu P, Yu L, Li X, Chen L, Xie F (2013) The properties of antimicrobial films derived from poly(lactic acid)/starch/chitosan blended matrix. Carbohyd Polym 98:959–966
Das D, Jayaram KK (2019) Enhancing resilient property of kaempferia galanga rhizome starch by succinylation. Int J Biol Macromol 124:1033–1039
Varma CAK, Jayaram KK (2018) Characterization and evaluation of smart releasing polysaccharide from yellow poinciana seed of Jharkhand. Int J Biol Macromol 118:2156–2162
Bhandari PN, Singhal RS (2002) Studies on the optimisation of preparation of succinate derivatives from corn and amaranth starches. Carbohyd Polym 47(3):277–283
Han JA, BeMiller JN (2007) Preparation and physical characteristics of slowly digesting modified food starches. Carbohyd Polym 67:366–374
Bao J (2003) Physical oroperties of octenyl succinic anhydride modified rice wheat and potato starches. J Agr Food Chem 51:2283–2287
Bhosale R, Singhal R (2007) Effect of octenylsuccinylation on physicochemical and functional properties of waxy maize and amaranth starches. Carbohyd Polym 68(3):447–456
He GQ (2006) Octenyl succinic anhydride modified early Indica rice starches differing in amylose content. J Agr Food Chem 54:2775–2779
Nilsson L, Bergenståhl B (2007) Adsorption of hydrophobically modified anionic starch at oppositely charged oil/water interfaces. J Colloid Interf Sci 308(2):508–513
Timgren A, Rayner M, Dejmek P, Marku D, Sjöö M (2013) Emulsion stabilizing capacity of intact starch granules modified by heat treatment or octenyl succinic anhydride. Food Sci Nutr 1(2):157–171
Eriksen M, Mackay J, Schluger N, Islami F, Drope J (2015) The Tobacco Atlas, 5th edn. American Cancer Society, Atlanta
Branton P, Lu AH, Schüth F (2009) The effect of carbon pore structure on the adsorption of cigarette smoke vapour phase compounds. Carbon 47(4):1005–1011
Esakky P, Moley KH (2016) Paternal smoking and germ cell death: A mechanistic link to the effects of cigarette smoke on spermatogenesis and possible long-term sequelae in offspring. Mol Cell Endocrinol 435:85–93
Mendel JR, Baig SA, Hall M, Jeong M, Byron M, Morgan JC et al (2018) Brand switching and toxic chemicals in cigarette smoke: a national study. PLOS ONE 13:e0189928
Noar SM, Kelley DE, Boynton MH, Morgan JC, Hall MG et al (2018) Identifying principles for effective messages about chemicals in cigarette smoke. Prev Med 106:31–37
Tindle HA, Duncan MS, Greevy RA, Vasan RS, Kundu S, Massion PP et al (2018) Lifetime smoking history and risk of lung cancer: Results from the framingham heart study. J Natl Cancer Inst 110(11):1201–1207
Chow WH, Dong LM, Devesa SS (2010) Epidemiology and risk factors for kidney cancer. Nat Rev Urol 7:245–257
Zuo JJ, Tao ZZ, Chen C, Hu ZW, Xu YX, Zheng AY et al (2017) Characteristics of cigarette smoking without alcohol consumption and laryngeal cancer: overall and time-risk relation: A meta-analysis of observational studies. Eur Arch Oto-Rhino-L 274(3):1617–1631
Beynon RA, Lang S, Schimansky S, Penfold CM, Waylen A, Thomas SJ et al (2018) Tobacco smoking and alcohol drinking at diagnosis of head and neck cancer and all-cause mortality: Results from head and neck 5000, a prospective observational cohort of people with head and neck cancer. Int J Cancer 143(5):1114–1127
Gild P, Vetterlein M, Gontero P, Roghmann F, Cumberbatch M, Dobruch J et al (2018) The impact of cigarette smoking on adverse pathological features and survival in patients undergoing radical cystectomy for urinary bladder cancer-a prospective European multicenter study of the EAU young academic urologists urothelial carcinoma group. Eur Urol Suppl 17(2):e1031–e1032
Oh TK, Jeon JH, Lee JM, Kim MS, Kim JH, Lee SJ, Eom W (2018) Chronic smoking is not associated with increased postoperative opioid use in patients with lung cancer or esophageal cancer. Pain Phys 21(1):49–55
Maisonneuve P, Lowenfels AB (2018) Variation of the age at onset of pancreatic cancer according to tobacco smoking and family history. Int J Epidemiol 47(4):1357–1357
Praud D, Rota M, Pelucchi C, Bertuccio P, Rosso T, Galeone C et al (2018) Cigarette smoking and gastric cancer in the stomach cancer pooling (stop) project. Eur J Cancer Prev 27(2):124–133
Vineis P, Alavanja M, Buffler P, Fontham E, Franceschi S, Gao YT et al (2004) Tobacco and cancer: Recent epidemiological evidence. J Natl Cancer Inst 96(2):99–106
Ahmaruzzaman M (2008) Adsorption of phenolic compounds on low-cost adsorbents: A review. Adv Colloid Interf 143(1):48–67
Chortyk OT, Schlotzhauer WS (1989) The contribution of low tar cigarettes to environmental tobacco smoke. J Anal Toxicol 13(3):129–134
Michałowicz JD (2007) Phenols sources and toxicity. Pol J Environ Stud 16(3):347–362
Pistonesi MF, Di NMS, Centurión ME, Lista AG, Fragoso WD, Pontes MJC et al (2010) Simultaneous determination of hydroquinone resorcinol phenol m-cresol and p-cresol in untreated air samples using spectrofluorimetry and a custom multiple linear regression-successive projection algorithm. Talanta 83(2):320–323
Mohammadi S, Kargari A, Sanaeepur H, Abbassian K, Najafi A, Mofarrah E (2015) Phenol removal from industrial wastewaters: a short review. Disalin Water Treat 53(8):2215–2234
Kulkarni SJ, Kaware JP (2013) Review on research for removal of phenol from wastewater. Int J Sci Res Pub 3(4):1–5
Villegas LGC, Mashhadi N, Chen M, Mukherjee D, Taylor KE, Biswas N (2016) A short review of techniques for phenol removal from wastewater. Cur Poll Rep 2(3):157–167
Pham TD, Tran TT, Pham TT, Dao TH, Le TS (2019) Adsorption characteristics of molecular oxytetracycline onto alumina particles: the role of surface modification with an anionic surfactant. J Mol Liq 287:110900.
Chen H, Wang C, Ye J, Zhou H, Tao R, Li W (2018) Preparation of starch-hard carbon spherules from ginkgo seeds and their phenol-adsorption characteristics. Molecules 23(1):96
Qiu C, Qin Y, Zhang S, Xiong L, Sun Q (2016) A comparative study of size-controlled worm-like amylopectin nanoparticles and spherical amylose nanoparticles: their characteristics and the adsorption properties of polyphenols. Food Chem 213:579–587
Haq F, Yu H, Wang Y, Wang L, Mehmood S, Haroon M et al (2021) Synthesis of succinylated starches and their application as adsorbents for the removal of phenol. J Polym Environ 29:2676–2685
Haq F, Yu H, Wang Y, Wang L, Haroon M, Khan A et al (2020) Synthesis of carboxymethyl starch grafted poly (methacrylic acids)(CMS-g-PMAAs) and their application as an adsorbent for the removal of ammonia and phenol. J Mol Struct 1207:127752
Haq F, Yu H, Wang L, Liu J, Mehmood S, Haroon M et al (2020) Dual modification of starches by phosphorylation and grafting and their application as adsorbents for the removal of phenol. J Polym Res 27(10):1–11
Haq F, Yu H, Wang L, Teng L, Mehmood S, Haroon M et al (2021) Synthesis of carboxymethyl starch grafted polyvinyl imidazole (CMS-g-PVIs) and their role as adsorbents for the removal of phenol. Environ Eng Res 26(5):200327
Sehaqui H, Kulasinski K, Pfenninger N, Zimmermann T, Tingaut P (2017) Highly carboxylated cellulose nanofibers via succinic anhydride esterification of wheat fibers and facile mechanical disintegration. Biomacromol 18(1):242–248
Ozmen N (2012) A study of the effect of acetylation on hemp fibres with vinyl acetate. BioResources 7(3):3800–3809
Guan W, Tang L, Wang Y, Cui H (2018) Fabrication of an effective avermectin nanoemulsion using a cleavable succinic ester emulsifier. J Agr Food Chem 66(29):7568–7576
Perez S, Bertoft E (2010) The molecular structures of starch components and their contribution to the architecture of starch granules: a comprehensive review. Starch - Stärke 62:389–420
Pham TD, Le TMA, Pham TMQ, Dang VH, Vu KL, Tran TK et al (2021) Synthesis and characterization of novel hybridized CeO2@ SiO2 nanoparticles based on rice husk and their application in antibiotic removal. Langmuir 37(9):2963–2973
Ngo TMV, Nguyen THL, Mai XT, Pham THN, Nguyen TTT, Pham TD (2021) Adsorptive removal of cationic dyes using hybrid material-based polyelectrolyte modified laterite soil. J Environ Chem Eng 9(2):105135
Altuna L, Herrera ML, Foresti ML (2018) Synthesis and characterization of octenyl succinic anhydride modified starches for food applications: A review of recent literature. Food Hydrocoll 80:97–110
Awokoya KN, Nwokocha LM, Moronkola BA, Moronkola DO (2011) Studies on the isolation structural and functional properties of starch succinate of cocoyam (Colocasia antiquorum). Chem Sin 2(6):228–244
Biparva P, Ranjbari E, Hadjmohammadi MR (2010) Application of dispersive liquid-liquid microextraction and spectrophotometric detection to the rapid determination of Rhodamine 6G in industrial effluents. Anal Chim Acta 674(2):206–210
Xueyu W, Xiaoxi L, Ling C, Fengwei X, Long Y, Bing L (2011) Preparation and characterisation of octenyl succinate starch as a delivery carrier for bioactive food components. Food Chem 126(3):1218–1225
Li D, Zhang X, Tian Y (2016) Ionic liquids as novel solvents for biosynthesis of octenyl succinic anhydride-modified waxy maize starch. Int J Biol Macromol 86:119–125
Xie W, Shao L, Liu Y (2010) Synthesis of starch esters in ionic liquids. J Appl Polym Sci 116(1):218–224
Li J, Ye F, Liu J, Zhao G (2015) Effects of octenylsuccination on physical, mechanical and moisture-proof properties of stretchable sweet potato starch film. Food Hydrocoll 46:226–232
Liu Z, Liu X, Cao Y, Xie W, Ma X, Yu X (2013) Edible starch sodium octenyl succinate film formation and Its physical properties. J Appl Polym Sci 127(4):2922–2927
Das D, Jha S, Kumar KJ (2015) Effect of carboxymethylation on physicochemical and release characteristics of Indian palo starch. Int J Biol Macromol 77:181–187
Pham TD, Pham TT, Phan MN, Ngo TMV, Vu CM (2020) Adsorption characteristics of anionic surfactant onto laterite soil with differently charged surfaces and application for cationic dye removal. J Mol Liq 301:112456
Shaarani F, Hameed B (2010) Batch adsorption of 2,4-dichlorophenol onto activated carbon derived from agricultural waste. Desalination 255(1–3):159–164
Terzyk AP, Ćwiertnia MS, Wiśniewski M, Gauden PA, Rychlicki G, Szymański GS (2007) Impact of the interaction with the positive charge in adsorption of benzene and other organic compounds from aqueous solutions on carbons. Appl Surf Sci 253(8):4006–4009
Haroon M, Yu H, Wang L, Ullah RS, Haq F, Teng L (2019) Synthesis and characterization of carboxymethyl starch-g-polyacrylic acids and their properties as adsorbents for ammonia and phenol. Int J Biol Macromol 138:349–358
An F, Du R, Wang X, Wan M, Dai X, Gao J (2012) Adsorption of phenolic compounds from aqueous solution using salicylic acid type adsorbent. J Hazard Mater 201:74–81
Ahmaruzzaman M (2008) Adsorption of phenolic compounds on low-cost adsorbents: a review. Adv Colloid Interfac 143(1–2):48–67
Srivastava VC, Swamy MM, Mall ID, Prasad B, Mishra IM (2006) Adsorptive removal of phenol by bagasse fly ash and activated carbon: equilibrium, kinetics and thermodynamics. Colloids Surf A 272(1–2):89–104
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Haq, F., Yu, H., Wang, L. et al. Synthesis of succinylated carboxymethyl starches and their role as adsorbents for the removal of phenol. Colloid Polym Sci 299, 1833–1841 (2021). https://doi.org/10.1007/s00396-021-04901-x
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DOI: https://doi.org/10.1007/s00396-021-04901-x