Synthesis 1,1-Dibutoxybutane from Single Reagent of n-Butanol Using Cr/Activated Carbon Catalyst

https://doi.org/10.22146/ijc.44829

Iip Izul Falah(1*), Mokhammad Fajar Pradipta(2), Alvan Luthfi Rinaldi(3), Wega Trisunaryanti(4)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara BLS 21, Bulaksumur, Yogyakarta 55281, Indonesia
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara BLS 21, Bulaksumur, Yogyakarta 55281, Indonesia
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara BLS 21, Bulaksumur, Yogyakarta 55281, Indonesia
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara BLS 21, Bulaksumur, Yogyakarta 55281, Indonesia
(*) Corresponding Author

Abstract


Synthesis of 1,1-dibutoxybutane from the single reagent of n-butanol using Cr/Activated Carbon (Cr/AC) as a catalyst has been done. The aims of this research were to evaluate the effect of temperature, amount of catalyst, and alcohol flow rate towards the yield of 1,1-dibutoxybutane. Activated carbon (AC) was prepared by activating coconut shell carbon at 650 °C in the atmosphere of H2 at a flow rate of 15 mL/min for 4 h, and then it was washed using acetone in a Soxhlet for 15 rounds, washed 3 times by 1.0 M HCl, and finally, it was sieved at 60–80 mesh. Metal content was analyzed using atomic absorption spectroscopy (AAS) of Na, Ca, and Fe. The AC was impregnated with Cr(VI) solution and reduced with H2 at 650 °C. The acidity of Cr/AC catalyst was determined by the adsorption of ammonia vapor. Optimization of n-butanol conversion to 1,1-dibutoxybutane using Cr/AC catalyst was conducted in an oven using variations of temperature of 450, 500, and 550 °C, catalyst amount of 5, 10, and 15 g, under an alcohol flow rate of 0.10, 0.50, and 0.90 mL/min. The conversions of 1,1-dibutoxybutane were analyzed by GC-MS and 1H-NMR. The results showed that after washing by acetone and 1.0 M HCl, the content of metals in the AC was significantly decreased. The AC and Cr/AC showed acidity of 2.49 and 8.27 mmol/g, respectively. The highest product of 1,1-dibutoxybutane (53.42%) was reached at 450 °C using 5 g catalyst of Cr/AC under the alcohol flow rate of 0.10 mL/min.

Keywords


n-butanol; 1,1-dibutoxybutane; Cr/AC; catalyst

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References

[1] Bencivenga, C., D’Ecclesia, R.L., and Triulzi, U., 2012, Oil prices and the financial crisis, Rev. Manag. Sci., 6, 227–238.

[2] Houdková, L., Boráň, J., Pěček, J., and Šumpela P., 2008, Biogas: A renewable source of energy, Therm. Sci., 12, 4, 27–33.

[3] Bhatti, H.N., Hanif, M.A., Qasim, M., and Rehman, A., 2008, Biodiesel production from waste tallow, Fuel, 87 (13-14), 2961–2966.

[4] Nebel, B.A., and Mittelbach, M., 2006, Biodiesel from extracted fat out of meat and bone meal, Eur. J. Lipid Sci. Technol., 108 (5), 398–403.

[5] Lebedevas, S., Vaicekauskas, A., Lebedeva, G., Makareviciene, V., Janulis, P., and Kazancev, K., 2006, Use of waste fats of animal and vegetable origin for the production of biodiesel fuel: Quality, motor properties, and emissions of harmful components, Energy Fuel, 20 (5), 2274–2280.

[6] Akoh, C.C., Chang, S.W., Lee, G.C., and Shaw, J.F., 2007, Enzymatic approach to biodiesel production, J. Agric. Food Chem., 55 (22), 8995–9005.

[7] Ooi, Y.S., Zakaria, R., Mohamed, A.R., and Bhatia, S., 2005, Catalytic conversion of fatty acid mixture to liquid fuels over mesoporous material, React. Kinet. Catal. Lett., 84 (2), 295–302

[8] Twaiq, F.A., Zabidi, N.A.M., Mohamed, A.R., and Bhatia, S., 2003, Catalytic conversion of palm oil over mesoporous aluminosilicate MCM 41 for the production of liquid hydrocarbon fuels, Fuel Process. Technol., 84 (1-3), 105–120.

[9] Gopal, S., and Smirniotis, P.G., 2002, Deactivation behavior of bifunctional Pt/H-zeolite catalysts during cyclopentane hydroconversion, J. Catal., 205 (2), 231–243.

[10] Ma, D., Wang, D., Su, L., Shu, Y., Xu, Y., and Bao, X., 2002, Carbonaceous deposition on Mo/HMCM-22 catalysts for methane aromatization: A TP technique investigation, J. Catal., 208, 260–269.

[11] Ali, O.M., Abdullah, N.R., Mamat, R., and Abdullah, A.A., 2015, Comparison of the effect of different alcohol additives with blended fuel on cyclic variation in diesel engine, Energy Procedia, 75, 2357–2362.

[12] Topgül, T., 2015, The effect of MTBE blends on engine performance and exhaust. Emission in a spark ignition engine, Fuel Process. Technol., 138, 480–489.

[13] Xing-Cai, L., Jian-Guang, Y., Wu-Gao, Z., and Zhen, H., 2014, Effect of cetane number improver on heat release rate and emissions of high speed diesel engine fueled with ethanol-diesel blend fuel, Fuel, 83 (14-15), 2013–2020.

[14] Geng, P., Cao, E., Tan, Q., and Wei, L., 2017, Effects of alternative fuels on the combustion characteristics and emission products from diesel engines: A review, Renewable Sustainable Energy Rev., 71, 523–534.

[15] Nord, K.E., and Haupt, D., 2005, Reducing the emission of particles from a diesel engine by adding an oxygenate to the fuel, Environ. Sci. Technol., 39 (16), 6260–6265.

[16] Agirre, L., Güemez, M.B., Ugarte, A., Requies, J., Barrio, V.L., Cambra, J.F., and Arias, P.L., 2013, Glycerol acetals as diesel additives: Kinetic study of the reaction between glycerol and acetaldehyde, Fuel Process. Technol., 116, 182–188.

[17] Rahaman, M., Graça, N.S., Pereira, C.S.M., and Rodrigues, A.E., 2015, Thermodynamic and kinetic studies for synthesis of the acetal (1,1-diethoxybuthane) catalyzed by Amberlyst 47 ion-exchange resin, Chem. Eng. J., 264, 257–267.

[18] Bueno, A.C., Goçalves, J.A., and Gusevskaya, E.V., 2007, Palladium-catalyzed oxidation of primary alcohol: Highly selective direct synthesis of acetals, Appl. Catal., A, 329, 1–6.

[19] Capeletti, M.R., Balzano, L., de la Puente, G., Laborde, M., and Sedran, U., 2000, Synthesis of acetal (1,1-diethoxyethane) from ethanol and acetaldehyde over acidic catalysts, Appl. Catal., A, 198 (1-2), L1–L4.

[20] Kaufhold, M., and El-Chawawi, M., 1996, Process for preparing acetaldehyde diethyl acetal, U.S. Patent, US5527969A.

[21] He, X., and Liu, H., 2014, Efficient synthesis of 1,1-diethoxyethane via sequential ethanol reaction on silica-supported copper and H-Y zeolite catalyst, Catal. Today, 233, 133–139.

[22] Pérez, M.A., Bringué, R., Iborra, M., Tejero, J., and Cunnil, F., 2014, Ion exchange resins as catalysts for the liquid-phase dehydration of 1-butanol to di-n-butyl ether, Appl. Catal., A, 482, 38–48.

[23] Siwale, L., Kristóf, L., Adam, T., Bereczky, A., Mbarawa, M., Penninger, A., and Kolesnikov, A., 2013, Combustion and emission characteristics of n-butanol/diesel fuel blend in a turbo-charged compression ignition engine, Fuel, 107, 409–418.

[24] Zhang, Z.H., and Balasubramanian, R., 2016, Investigation of particulate emission characteristics of a diesel engine fueled with higher alcohols/biodiesel blends, Appl. Energy, 163, 71–80.

[25] Zaharin, M.S.M., Abdullah, N.R., Najafi, G., Sharudin, H., and Yusaf, T., 2017, Effects of physicochemical properties of biodiesel fuel blends with alcohol on diesel engine performance and exhaust emissions: A review, Renewable Sustainable Energy Rev., 79, 475–493.

[26] Falah, I.I., and Triyono, 2010, Conversion of n-pentanol and n-butanol over Cu/AC catalyst, J. Chem. Chem. Eng., 4 (6), 22–28.



DOI: https://doi.org/10.22146/ijc.44829

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