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Optimization of green and environmentally-benign synthesis of isoamyl acetate in the presence of ball-milled seashells by response surface methodology

  • McElroy, C. R., Constantinou, A., Jones, L. C., Summerton, L. & Clark, J. H. Towards a holistic approach to metrics for the 21st century pharmaceutical industry. Green Chem. 17, 3111–3121. https://doi.org/10.1039/C5GC00340G (2015).

    Article 
    CAS 

    Google Scholar 

  • Zimmerman, J. B., Anastas, P. T., Erythropel, H. C. & Leitner, W. Designing for a green chemistry future. Science 367, 397–400. https://doi.org/10.1126/science.aay3060 (2020).

    Article 
    ADS 
    CAS 
    PubMed 

    Google Scholar 

  • Sheldon, R. A. Metrics of green chemistry and sustainability: Past, present, and future. ACS Sustain. Chem. Eng. 6, 32–48. https://doi.org/10.1021/acssuschemeng.7b03505 (2018).

    Article 
    CAS 

    Google Scholar 

  • Anastas, P. T. & Williamson, T. C. in Green Chemistry, Vol. 626 ACS Symposium Series Ch. 1, 1–17 (American Chemical Society, 1996). https://doi.org/10.1021/bk-1996-0626.ch001.

  • Clark, H. J. Green chemistry: Challenges and opportunities. Green Chem. 1, 1–8. https://doi.org/10.1039/A807961G (1999).

    Article 
    CAS 

    Google Scholar 

  • Dekamin, M. G. & Eslami, M. Highly efficient organocatalytic synthesis of diverse and densely functionalized 2-amino-3-cyano-4 H-pyrans under mechanochemical ball milling. Green Chem. 16, 4914–4921 (2014).

    Article 
    CAS 

    Google Scholar 

  • Eze, A. A. et al. Wet ball milling of niobium by using ethanol, determination of the crystallite size and microstructures. Sci. Rep. 11, 1–8 (2021).

    Article 

    Google Scholar 

  • Gorrasi, G. & Sorrentino, A. Mechanical milling as a technology to produce structural and functional bio-nanocomposites. Green Chem. 17, 2610–2625 (2015).

    Article 
    CAS 

    Google Scholar 

  • Li, L. H., Glushenkov, A. M., Hait, S. K., Hodgson, P. & Chen, Y. High-efficient production of boron nitride nanosheets via an optimized ball milling process for lubrication in oil. Sci. Rep. 4, 1–6 (2014).

    Google Scholar 

  • Mac Naughton, G. E., Rolfe, S. A. & Siraj-Blatchford, I. E. Doing Early Childhood Research: International Perspectives on Theory and Practice (Open University Press, 2001).

  • Evangelisti, L. et al. The borderline between reactivity and pre-reactivity of binary mixtures of gaseous carboxylic acids and alcohols. Angew. Chem. 129, 3930–3933 (2017).

    Article 
    ADS 

    Google Scholar 

  • Gaspa, S., Porcheddu, A. & De Luca, L. Metal-free oxidative cross esterification of alcohols via acyl chloride formation. Adv. Synth. Catal. 358, 154–158 (2016).

    Article 
    CAS 

    Google Scholar 

  • Fiorio, J. L., Braga, A. H., Guedes, C. L. S. B. & Rossi, L. M. Reusable heterogeneous tungstophosphoric acid-derived catalyst for green esterification of carboxylic acids. ACS Sustain. Chem. Eng. 7, 15874–15883 (2019).

    Article 
    CAS 

    Google Scholar 

  • Karimi, B., Mirzaei, H. M. & Mobaraki, A. Periodic mesoporous organosilica functionalized sulfonic acids as highly efficient and recyclable catalysts in biodiesel production. Catal. Sci. Technol. 2, 828–834 (2012).

    Article 
    CAS 

    Google Scholar 

  • Tran, T. T. V. et al. Selective production of green solvent (isoamyl acetate) from fusel oil using a sulfonic acid-functionalized KIT-6 catalyst. Mol. Catal. 484, 110724 (2020).

    Article 
    CAS 

    Google Scholar 

  • Afshar, S. et al. Optimization of catalytic activity of sulfated titania for efficient synthesis of isoamyl acetate by response surface methodology. Mon. Chem. Chem. Mon. 146, 1949–1957 (2015).

    Article 
    CAS 

    Google Scholar 

  • Chng, L. L., Yang, J. & Ying, J. Y. Efficient synthesis of amides and esters from alcohols under aerobic ambient conditions catalyzed by a Au/mesoporous Al2O3 nanocatalyst. Chemsuschem 8, 1916–1925 (2015).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Lozano, P., Bernal, J. M. & Navarro, A. A clean enzymatic process for producing flavour esters by direct esterification in switchable ionic liquid/solid phases. Green Chem. 14, 3026–3033 (2012).

    Article 
    CAS 

    Google Scholar 

  • Su, L., Hong, R., Guo, X., Wu, J. & Xia, Y. Short-chain aliphatic ester synthesis using Thermobifida fusca cutinase. Food Chem. 206, 131–136 (2016).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Güvenç, A., Kapucu, N., Kapucu, H., Aydoğan, Ö. & Mehmetoğlu, Ü. Enzymatic esterification of isoamyl alcohol obtained from fusel oil: Optimization by response surface methodolgy. Enzyme Microb. Technol. 40, 778–785 (2007).

    Article 

    Google Scholar 

  • Torres, S., Baigorí, M. D., Swathy, S., Pandey, A. & Castro, G. R. Enzymatic synthesis of banana flavour (isoamyl acetate) by Bacillus licheniformis S-86 esterase. Food Res. Int. 42, 454–460 (2009).

    Article 
    CAS 

    Google Scholar 

  • Ando, H., Kurata, A. & Kishimoto, N. Antimicrobial properties and mechanism of volatile isoamyl acetate, a main flavour component of Japanese sake (Ginjo-shu). J. Appl. Microbiol. 118, 873–880 (2015).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Ghamgui, H., Karra-Chaâbouni, M., Bezzine, S., Miled, N. & Gargouri, Y. Production of isoamyl acetate with immobilized Staphylococcus simulans lipase in a solvent-free system. Enzyme Microb. Technol. 38, 788–794 (2006).

    Article 
    CAS 

    Google Scholar 

  • Romero, M., Calvo, L., Alba, C., Daneshfar, A. & Ghaziaskar, H. Enzymatic synthesis of isoamyl acetate with immobilized Candida antarctica lipase in n-hexane. Enzyme Microb. Technol. 37, 42–48 (2005).

    Article 
    CAS 

    Google Scholar 

  • Borges, M. E. & Díaz, L. Recent developments on heterogeneous catalysts for biodiesel production by oil esterification and transesterification reactions: A review. Renew. Sustain. Energy Rev. 16, 2839–2849 (2012).

    Article 
    CAS 

    Google Scholar 

  • Li, K.-T., Wang, C.-K., Wang, I. & Wang, C.-M. Esterification of lactic acid over TiO2–ZrO2 catalysts. Appl. Catal. A 392, 180–183 (2011).

    Article 
    CAS 

    Google Scholar 

  • Clark, J. H. & Rhodes, C. N. In Clean Synthesis Using Porous Inorganic Solid Catalysts and Supported Reagents, Vol. 4, (Royal Society of Chemistry, London, 2000). https://doi.org/10.1039/9781847550569

  • Dekamin, M. G. et al. Sodium alginate: An efficient biopolymeric catalyst for green synthesis of 2-amino-4H-pyran derivatives. Int. J. Biol. Macromol. 87, 172–179 (2016).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Melfi, D. T., dos Santos, K. C., Ramos, L. P. & Corazza, M. L. Supercritical CO2 as solvent for fatty acids esterification with ethanol catalyzed by Amberlyst-15. J. Supercrit. Fluids 158, 104736 (2020).

    Article 
    CAS 

    Google Scholar 

  • Azudin, N. Y., Mashitah, M. & Abd Shukor, S. R. Optimization of isoamyl acetate production in a solvent-free system. J. Food Qual. 36, 441–446 (2013).

    Article 
    CAS 

    Google Scholar 

  • Ćorović, M. et al. Immobilization of Candida antarctica lipase B onto Purolite® MN102 and its application in solvent-free and organic media esterification. Bioprocess Biosyst. Eng. 40, 23–34 (2017).

    Article 
    PubMed 

    Google Scholar 

  • Liu, C. & Luo, G. Synthesis of isoamyl acetate catalyzed by ferric tri-dodecylsulfonate. Riyong Huaxue Gongye 34, 403–405 (2004).

    Google Scholar 

  • Narwal, S. K., Saun, N. K., Dogra, P. & Gupta, R. Green synthesis of isoamyl acetate via silica immobilized novel thermophilic lipase from Bacillus aerius. Russ. J. Bioorg. Chem. 42, 69–73 (2016).

    Article 
    CAS 

    Google Scholar 

  • Pizzio, L., Vázquez, P., Cáceres, C. & Blanco, M. Tungstophosphoric and molybdophosphoric acids supported on zirconia as esterification catalysts. Catal. Lett. 77, 233–239 (2001).

    Article 
    CAS 

    Google Scholar 

  • Saha, B., Alqahtani, A. & Teo, H. T. R. Production of iso-Amyl Acetate: Heterogeneous Kinetics and Techno-feasibility Evaluation for Catalytic Distillation. Int. J. Chem. React. Eng. 3(1), https://doi.org/10.2202/1542-6580.1231 (2005).

  • Osorio-Viana, W., Ibarra-Taquez, H. N., Dobrosz-Gomez, I. & Gómez-García, M. Á. Hybrid membrane and conventional processes comparison for isoamyl acetate production. Chem. Eng. Process. 76, 70–82 (2014).

    Article 
    CAS 

    Google Scholar 

  • Fang, M. et al. Synthesis of isoamyl acetate using polyoxometalate-based sulfonated ionic liquid as catalyst. Indian J. Chem. Sect. A 53A, 1485–1492 (2014).

  • Yang, Z., Zhou, C., Zhang, W., Li, H. & Chen, M. β-MnO2 nanorods: A new and efficient catalyst for isoamyl acetate synthesis. Colloids Surf., A 356, 134–139 (2010).

    Article 
    CAS 

    Google Scholar 

  • Yang, Z. et al. Kinetic study and process simulation of transesterification of methyl acetate and isoamyl alcohol catalyzed by ionic liquid. Ind. Eng. Chem. Res. 54, 1204–1215 (2015).

    Article 
    CAS 

    Google Scholar 

  • Dohendou, M., Pakzad, K., Nezafat, Z., Nasrollahzadeh, M. & Dekamin, M. G. Progresses in chitin, chitosan, starch, cellulose, pectin, alginate, gelatin and gum based (nano)catalysts for the Heck coupling reactions: A review. Int. J. Biol. Macromol. 192, 771–819. https://doi.org/10.1016/j.ijbiomac.2021.09.162 (2021).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Valiey, E., Dekamin, M. G. & Alirezvani, Z. Melamine-modified chitosan materials: An efficient and recyclable bifunctional organocatalyst for green synthesis of densely functionalized bioactive dihydropyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives. Int. J. Biol. Macromol. 129, 407–421. https://doi.org/10.1016/j.ijbiomac.2019.01.027 (2019).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Dekamin, M. G., Kazemi, E., Karimi, Z., Mohammadalipoor, M. & Naimi-Jamal, M. R. Chitosan: An efficient biomacromolecule support for synergic catalyzing of Hantzsch esters by CuSO4. Int. J. Biol. Macromol. 93, 767–774. https://doi.org/10.1016/j.ijbiomac.2016.09.012 (2016).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Valiey, E., Dekamin, M. G. & Bondarian, S. Sulfamic acid grafted to cross-linked chitosan by dendritic units: A bio-based, highly efficient and heterogeneous organocatalyst for green synthesis of 2,3-dihydroquinazoline derivatives. RSC Adv. 13, 320–334. https://doi.org/10.1039/D2RA07319F (2023).

    Article 
    ADS 
    CAS 

    Google Scholar 

  • Dekamin, M. G., Azimoshan, M. & Ramezani, L. Chitosan: A highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions. Green Chem. 15, 811–820. https://doi.org/10.1039/C3GC36901C (2013).

    Article 
    CAS 

    Google Scholar 

  • Alirezvani, Z., Dekamin, M. G. & Valiey, E. Cu (II) and magnetite nanoparticles decorated melamine-functionalized chitosan: A synergistic multifunctional catalyst for sustainable cascade oxidation of benzyl alcohols/Knoevenagel condensation. Sci. Rep. 9, 17758 (2019).

    Article 
    ADS 
    PubMed 
    PubMed Central 

    Google Scholar 

  • Rostami, N., Dekamin, M., Valiey, E. & Fanimoghadam, H. Chitosan-EDTA-Cellulose network as a green, recyclable and multifunctional biopolymeric organocatalyst for the one-pot synthesis of 2-amino-4H-pyran derivatives. Sci. Rep. 12, 8642–8642 (2022).

    Article 
    ADS 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar 

  • Frindy, S., el Kadib, A., Lahcini, M., Primo, A. & García, H. Copper nanoparticles stabilized in a porous chitosan aerogel as a heterogeneous catalyst for C−S cross-coupling. ChemCatChem 7, 3307–3315 (2015).

    Article 
    CAS 

    Google Scholar 

  • Pettignano, A. et al. Alginic acid aerogel: A heterogeneous Brønsted acid promoter for the direct Mannich reaction. New J. Chem. 39, 4222–4226 (2015).

    Article 
    CAS 

    Google Scholar 

  • Schnepp, Z. Biopolymers as a flexible resource for nanochemistry. Angew. Chem. Int. Ed. 52, 1096–1108 (2013).

    Article 
    CAS 

    Google Scholar 

  • Khrunyk, Y., Lach, S., Petrenko, I. & Ehrlich, H. Progress in modern marine biomaterials research. Mar. Drugs 18, 589 (2020).

    Article 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar 

  • Lee, I. Molecular self-assembly: Smart design of surface and interface via secondary molecular interactions. Langmuir 29, 2476–2489. https://doi.org/10.1021/la304123b (2013).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Shaheed, N., Javanshir, S., Esmkhani, M., Dekamin, M. G. & Naimi-Jamal, M. R. Synthesis of nanocellulose aerogels and Cu-BTC/nanocellulose aerogel composites for adsorption of organic dyes and heavy metal ions. Sci. Rep. 11, 18553 (2021).

    Article 
    ADS 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar 

  • Abdullah, M. A. et al. Processing Aspects and biomedical and environmental applications of sustainable nanocomposites containing nanofillers. In Sustainable Polymer Composites and Nanocomposites, (eds Inamuddin et al.) 727–757 (Springer, Cham, 2019). https://doi.org/10.1007/978-3-030-05399-4_25

  • Dekamin, M. G. et al. Alginic acid: A highly efficient renewable and heterogeneous biopolymeric catalyst for one-pot synthesis of the Hantzsch 1,4-dihydropyridines. RSC Adv. 4, 56658–56664. https://doi.org/10.1039/C4RA11801D (2014).

    Article 
    ADS 
    CAS 

    Google Scholar 

  • Ilkhanizadeh, S., Khalafy, J. & Dekamin, M. G. Sodium alginate: A biopolymeric catalyst for the synthesis of novel and known polysubstituted pyrano[3,2-c]chromenes. Int. J. Biol. Macromol. 140, 605–613. https://doi.org/10.1016/j.ijbiomac.2019.08.154 (2019).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Dekamin, M. G. et al. Alginic acid: A mild and renewable bifunctional heterogeneous biopolymeric organocatalyst for efficient and facile synthesis of polyhydroquinolines. Int. J. Biol. Macromol. 108, 1273–1280. https://doi.org/10.1016/j.ijbiomac.2017.11.050 (2018).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Rostami, N., Dekamin, M. G. & Valiey, E. Chitosan-EDTA-cellulose bio-based network: A recyclable multifunctional organocatalyst for green and expeditious synthesis of Hantzsch esters. Carbohydr. Polym. Technol. Appl. 5, 100279. https://doi.org/10.1016/j.carpta.2022.100279 (2023).

    Article 
    CAS 

    Google Scholar 

  • Bezerra, M. A., Santelli, R. E., Oliveira, E. P., Villar, L. S. & Escaleira, L. A. Response surface methodology (RSM) as a tool for optimization in analytical chemistry. Talanta 76, 965–977. https://doi.org/10.1016/j.talanta.2008.05.019 (2008).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Hill, W. J. & Hunter, W. G. A review of response surface methodology: A literature survey. Technometrics 8, 571–590. https://doi.org/10.1080/00401706.1966.10490404 (1966).

    Article 
    MathSciNet 

    Google Scholar 

  • Hamidi, F. et al. Acid red 18 removal from aqueous solution by nanocrystalline granular ferric hydroxide (GFH); optimization by response surface methodology & genetic-algorithm. Sci. Rep. 12, 1–15 (2022).

    Article 

    Google Scholar 

  • Han, X.-X. et al. Syntheses of novel halogen-free Brønsted–Lewis acidic ionic liquid catalysts and their applications for synthesis of methyl caprylate. Green Chem. 17, 499–508 (2015).

    Article 
    CAS 

    Google Scholar 

  • Rehman, K. et al. Operational parameters optimization for remediation of crude oil-polluted water in floating treatment wetlands using response surface methodology. Sci. Rep. 12, 1–11 (2022).

    Article 

    Google Scholar 

  • Kamari, S., Ghorbani, F. & Sanati, A. M. Adsorptive removal of lead from aqueous solutions by amine–functionalized magMCM-41 as a low–cost nanocomposite prepared from rice husk: Modeling and optimization by response surface methodology. Sustain. Chem. Pharm. 13, 100153. https://doi.org/10.1016/j.scp.2019.100153 (2019).

    Article 

    Google Scholar 

  • Sanati, A. M., Kamari, S. & Ghorbani, F. Application of response surface methodology for optimization of cadmium adsorption from aqueous solutions by Fe3O4@SiO2@APTMS core–shell magnetic nanohybrid. Surf. Interfaces 17, 100374. https://doi.org/10.1016/j.surfin.2019.100374 (2019).

    Article 
    CAS 

    Google Scholar 

  • Guner, S. G. & Dericioglu, A. Nacre-mimetic epoxy matrix composites reinforced by two-dimensional glass reinforcements. RSC Adv. 6, 33184–33196 (2016).

    Article 
    ADS 
    CAS 

    Google Scholar 

  • Shao, Y., Zhao, H.-P. & Feng, X.-Q. Optimal characteristic nanosizes of mineral bridges in mollusk nacre. RSC Adv. 4, 32451–32456 (2014).

    Article 
    ADS 
    CAS 

    Google Scholar 

  • Jaji, A. Z. et al. Synthesis, characterization, and cytocompatibility of potential cockle shell aragonite nanocrystals for osteoporosis therapy and hormonal delivery. Nanotechnol. Sci. Appl. 10, 23 (2017).

    Article 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar 

  • Çam, M. & Aaby, K. Optimization of extraction of apple pomace phenolics with water by response surface methodology. J. Agric. Food Chem. 58, 9103–9111 (2010).

    Article 
    PubMed 

    Google Scholar 

  • Iwuchukwu, I. J. et al. Optimization of photosynthetic hydrogen yield from platinized photosystem I complexes using response surface methodology. Int. J. Hydrog. Energy 36, 11684–11692 (2011).

    Article 
    CAS 

    Google Scholar 

  • Hu, C. et al. Characterization and photocatalytic activity of noble-metal-supported surface TiO2/SiO2. Appl. Catal. A 253, 389–396 (2003).

    Article 
    CAS 

    Google Scholar 

  • Noda, L. K., de Almeida, R. M., Probst, L. F. D. & Gonçalves, N. S. Characterization of sulfated TiO2 prepared by the sol–gel method and its catalytic activity in the n-hexane isomerization reaction. J. Mol. Catal. A Chem. 225, 39–46 (2005).

    Article 
    CAS 

    Google Scholar 

  • Jalali-Heravi, M., Parastar, H. & Ebrahimi-Najafabadi, H. Characterization of volatile components of Iranian saffron using factorial-based response surface modeling of ultrasonic extraction combined with gas chromatography–mass spectrometry analysis. J. Chromatogr. A 1216, 6088–6097 (2009).

    Article 
    CAS 
    PubMed 

    Google Scholar 

  • Sendzikiene, E., Sinkuniene, D., Kazanceva, I. & Kazancev, K. Optimization of low quality rapeseed oil transesterification with butanol by applying the response surface methodology. Renew. Energy 87, 266–272 (2016).

    Article 
    CAS 

    Google Scholar 

  • Das, R., Sarkar, S. & Bhattacharjee, C. Photocatalytic degradation of chlorhexidine—a chemical assessment and prediction of optimal condition by response surface methodology. J. Water Process Eng. 2, 79–86 (2014).

    Article 

    Google Scholar 

  • Nandiwale, K. Y., Galande, N. D. & Bokade, V. V. Process optimization by response surface methodology for transesterification of renewable ethyl acetate to butyl acetate biofuel additive over borated USY zeolite. RSC Adv. 5, 17109–17116 (2015).

    Article 
    ADS 
    CAS 

    Google Scholar 

  • Soltani, R. D. C. & Safari, M. Periodate-assisted pulsed sonocatalysis of real textile wastewater in the presence of MgO nanoparticles: Response surface methodological optimization. Ultrason. Sonochem. 32, 181–190 (2016).

    Article 

    Google Scholar 

  • Tan, K. T., Lee, K. T. & Mohamed, A. R. A glycerol-free process to produce biodiesel by supercritical methyl acetate technology: An optimization study via response surface methodology. Biores. Technol. 101, 965–969 (2010).

    Article 
    CAS 

    Google Scholar 

  • Nagaraju, N., Peeran, M. & Prasad, D. Synthesis of isoamyl acetate usin NaX and NaY zeolites as catalysts. React. Kinet. Catal. Lett. 61, 155–160 (1997).

    Article 
    CAS 

    Google Scholar 

  • Pizzio, L. R. & Blanco, M. N. Isoamyl acetate production catalyzed by H3PW12O40 on their partially substituted Cs or K salts. Appl. Catal. A 255, 265–277 (2003).

    Article 
    CAS 

    Google Scholar 

  • Dekamin, M. G., Karimi, Z. & Farahmand, M. Tetraethylammonium 2-(N-hydroxycarbamoyl)benzoate: A powerful bifunctional metal-free catalyst for efficient and rapid cyanosilylation of carbonyl compounds under mild conditions. Catal. Sci. Technol. 2, 1375–1381. https://doi.org/10.1039/C2CY20037F (2012).

    Article 
    CAS 

    Google Scholar 

  • Dekamin, M. G., Sagheb-Asl, S. & Reza Naimi-Jamal, M. An expeditious synthesis of cyanohydrin trimethylsilyl ethers using tetraethylammonium 2-(carbamoyl)benzoate as a bifunctional organocatalyst. Tetrahedron Lett. 50, 4063–4066. https://doi.org/10.1016/j.tetlet.2009.04.090 (2009).

    Article 
    CAS 

    Google Scholar 

  • Alirezvani, Z., Dekamin, M. G. & Valiey, E. New hydrogen-bond-enriched 1,3,5-tris(2-hydroxyethyl) isocyanurate covalently functionalized MCM-41: An efficient and recoverable hybrid catalyst for convenient synthesis of acridinedione derivatives. ACS Omega 4, 20618–20633. https://doi.org/10.1021/acsomega.9b02755 (2019).

    Article 
    CAS 
    PubMed 
    PubMed Central 

    Google Scholar 


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