Synthesis and characterization of sulfonated carbon catalysts derived from biomass waste and its evaluation in glycerol acetylation

Biomass Conversion and Biorefinery - Tập 12 - Trang 2045-2060 - 2020
Usman Idris Nda-Umar1,2, Irmawati Ramli1,3, Ernee Noryana Muhamad1,3, Yun Hin Taufiq-Yap4,3, Norsahida Azri1,3
1Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, UPM Serdang, Malaysia
2Department of Chemical Sciences, Federal Polytechnic, Bida, Nigeria
3Catalysis Science and Technology Research Centre (PutraCat), Faculty of Science, Universiti Putra Malaysia (UPM), Serdang, Malaysia
4Department of Chemistry, Faculty of Science, Universiti Putra Malaysia-UPM, Serdang, Malaysia

Tóm tắt

Sulfonated carbon catalysts were synthesized from palm kernel shell biomass using direct, chemical and template methods of carbonization under CO2 environment at 400 and 800 °C respectively and subsequently functionalized with concentrated sulfuric acid. The precursor material and the synthesized catalysts were characterized by proximate analysis, CHNS, XRD, FTIR, TPD, TGA, SEM, N2 adsorption isotherm, BET surface area, and acid-base titration. The synthesized acid catalysts were evaluated in glycerol acetylation with acetic acid (molar ratio 1:6) in a batch liquid phase reaction under atmospheric pressure at 120 °C, 450 rpm for 1 h, 3 h, and 5 h respectively. The performance was compared with commercial Amberlyst-15 catalysts and homogeneous concentrated sulfuric acid. Of all the synthesized catalysts, the catalyst obtained from the template method carbonized at 800 °C showed the highest selectivity to triacetin (58.9%) with over 97% glycerol conversion within a 3-h reaction time. The selectivity to monoacetin and diacetin was 5.8 and 32.2% respectively. The catalytic activity of the catalyst was attributed to the synergistic effect of good physicochemical characteristics including textural properties and high acidic site density.

Tài liệu tham khảo

Nanda MR, Yuan Z, Qin W, Ghaziaskar HS, Poirier MA, Xu CC (2014) Thermodynamic and kinetic studies of a catalytic process to convert glycerol into solketal as an oxygenated fuel additive. Fuel 117:470–477. https://doi.org/10.1016/j.fuel.2013.09.066 Naylor RL, Higgins MM (2017) The political economy of biodiesel in an era of low oil prices. Renew Sust Energ Rev 77:695–705. https://doi.org/10.1016/j.rser.2017.04.026 Cahyono RB, Mufrodi Z, Hidayat A, Budiman A (2016) Acetylation of glycerol for triacetin production using Zr-natural zeolite catalyst. ARPN J Eng Appl Sci 11:5194–5197 Mallesham B, Rao BG, Reddy BM (2016) Production of biofuel additives by esteri fi cation and acetalization of bioglycerol. Comptes rendus - Chim 19:1194–1202. https://doi.org/10.1016/j.crci.2015.09.011 Khayoon MS, Triwahyono S, Hameed BH, Jalil AA (2014) Improved production of fuel oxygenates via glycerol acetylation with acetic acid. Chem Eng J 243:473–484. https://doi.org/10.1016/j.cej.2014.01.027 Setyaningsih L, Siddiq F, Pramezy A (2018) Esterification of glycerol with acetic acid over Lewatit catalyst. MATEC Web Conf 154:2–5. https://doi.org/10.1051/matecconf/201815401028 Gao X, Zhu S, Li Y (2015) Graphene oxide as a facile solid acid catalyst for the production of bioadditives from glycerol esteri fi cation. Catal Commun 62:48–51. https://doi.org/10.1016/j.catcom.2015.01.007 Kong PS, Aroua MK, Daud WMAW, Lee HV, Cognet P, Pérès Y (2016) Catalytic role of solid acid catalysts in glycerol acetylation for the production of bio-additives: a review. RSC Adv 6:68885–68905. https://doi.org/10.1039/c6ra10686b Gonçalves CE, Laier LO, Cardoso AL, Da Silva MJ (2012) Bioadditive synthesis from H 3 PW 12 O 40 -catalyzed glycerol esteri fi cation with HOAc under mild reaction conditions. Fuel Process Technol 102:46–52. https://doi.org/10.1016/j.fuproc.2012.04.027 Kakasaheb YN, Prashant SN, Vijay VB (2018) Synthesis of oxygenated fuel additives via acetylation of bio-glycerol over H 2 SO 4 modified montmorillonite K10 catalyst. Prog Petrochemical Sci 1:1–5 Ramalingam RJ, Radhika T, Adam F, Dolla HT (2016) Acetylation of glycerol over bimetallic Ag – Cu doped rice husk silica based biomass catalyst for bio-fuel additives application. Int J Ind Chem 7:187–194. https://doi.org/10.1007/s40090-016-0073-0 Testa ML, La Parola V, Liotta LF, Venezia AM (2013) Screening of different solid acid catalysts for glycerol acetylation. J Mol Catal A Chem 367:69–76. https://doi.org/10.1016/j.molcata.2012.10.027 Okoye PU, Abdullah AZ, Hameed BH (2017) Synthesis of oxygenated fuel additives via glycerol esterification with acetic acid over bio-derived carbon catalyst. Fuel 209:538–544. https://doi.org/10.1016/j.fuel.2017.08.024 Sánchez JA, Hernández DL, Moreno JA, Mondragón F, Fernández JJ (2011) Alternative carbon based acid catalyst for selective esterification of glycerol to acetylglycerols. Appl Catal A Gen 405:55–60. https://doi.org/10.1016/j.apcata.2011.07.027 Zhou Y, Niu S, Li J (2016) Activity of the carbon-based heterogeneous acid catalyst derived from bamboo in esterification of oleic acid with ethanol. Energy Convers Manag 114:188–196. https://doi.org/10.1016/j.enconman.2016.02.027 Carvalho WA, Galhardo TS, Simone N et al (2013) Preparation of sulfonated carbons from rice husk and their application in catalytic conversion of glycerol. ACS Sustain Chem Eng 1:1381–1389. https://doi.org/10.1021/sc400117t Goscianska J, Malaika A (2019) A facile post-synthetic modification of ordered mesoporous carbon to get efficient catalysts for the formation of acetins. Catal Today:1–10. https://doi.org/10.1016/j.cattod.2019.02.049 Mee Chin C, Basri Wahid M, Kook Weng C (2008) Availability and potential of biomass resources from the Malaysian Palm Oil Industry for generating renewable energy**. Oil Palm Bull 56:23–28 Yakout SM, Sharaf El-Deen G (2016) Characterization of activated carbon prepared by phosphoric acid activation of olive stones. Arab J Chem 9:S1155–S1162. https://doi.org/10.1016/j.arabjc.2011.12.002 Konwar LJ, Mäki-Arvela P, Kumar N, Mikkola JP, Sarma AK, Deka D (2016) Selective esterification of fatty acids with glycerol to monoglycerides over –SO3H functionalized carbon catalysts. React Kinet Mech Catal 119:121–138. https://doi.org/10.1007/s11144-016-1040-7 Kambo HS, Dutta A (2014) Strength, storage, and combustion characteristics of densified lignocellulosic biomass produced via torrefaction and hydrothermal carbonization. Appl Energy 135:182–191. https://doi.org/10.1016/j.apenergy.2014.08.094 Jiménez Toro MJ, Dou X, Ajewole I, Wang J, Chong K, Ai N, Zeng G, Chen T (2019) Preparation and optimization of macroalgae-derived solid acid catalysts. Waste Biomass Valorization 10:805–816. https://doi.org/10.1007/s12649-017-0101-0 Lathiya DR, Bhatt DV, Maheria KC (2018) Synthesis of sulfonated carbon catalyst from waste orange peel for cost effective biodiesel production. Bioresour Technol Rep 2:69–76. https://doi.org/10.1016/j.biteb.2018.04.007 Dalla Costa BO, Decolatti HP, Legnoverde MS, Querini CA (2017) Influence of acidic properties of different solid acid catalysts for glycerol acetylation. Catal Today 289:222–230. https://doi.org/10.1016/j.cattod.2016.09.015 Kumar A, Jena HM (2016) Preparation and characterization of high surface area activated carbon from Fox nut (Euryale ferox) shell by chemical activation with H3PO4. Results Phys 6:651–658. https://doi.org/10.1016/j.rinp.2016.09.012 Chellappan S, Nair V, Sajith V, Aparna K (2018) Synthesis, optimization and characterization of biochar based catalyst from sawdust for simultaneous esterification and transesterification. Chin J Chem Eng:2654–2663. https://doi.org/10.1016/j.cjche.2018.02.034 Ning Y, Niu S (2017) Preparation and catalytic performance in esterification of a bamboo-based heterogeneous acid catalyst with microwave assistance. Energy Convers Manag 153:446–454. https://doi.org/10.1016/j.enconman.2017.10.025 Thushari I, Babel S (2018) Sustainable utilization of waste palm oil and sulfonated carbon catalyst derived from coconut meal residue for biodiesel production. Bioresour Technol 248:199–203. https://doi.org/10.1016/j.biortech.2017.06.106 Thushari I, Babel S (2018) Preparation of solid acid catalysts from waste biomass and their application for microwave-assisted biodiesel production from waste palm oil. Waste Manag Res 36:719–728. https://doi.org/10.1177/0734242X18789821 Laohapornchaiphan J, Smith CB, Smith SM (2017) One-step preparation of carbon-based solid acid catalyst from water hyacinth leaves for esterification of oleic acid and dehydration of xylose. Chem - An Asian J 12:3178–3186. https://doi.org/10.1002/asia.201701369 Shen S, Li H, Wang T, Han Y, Qin H (2013) Preparation of a carbon-based material derived from coking industry solid waste–phenol residue and its performance as hydrolysis catalysts. Asia Pac J Chem Eng 8:447–452. https://doi.org/10.1002/apj Tang X, Niu S (2019) Preparation of carbon-based solid acid with large surface area to catalyze esterification for biodiesel production. J Ind Eng Chem 69:187–195. https://doi.org/10.1016/j.jiec.2018.09.016 Akinfalabi SI, Rashid U, Yunus R, Taufiq-Yap YH (2017) Synthesis of biodiesel from palm fatty acid distillate using sulfonated palm seed cake catalyst. Renew Energy 111:611–619. https://doi.org/10.1016/j.renene.2017.04.056 Shuit SH, Tan SH (2014) Feasibility study of various sulphonation methods for transforming carbon nanotubes into catalysts for the esterification of palm fatty acid distillate. Energy Convers Manag 88:1283–1289. https://doi.org/10.1016/j.enconman.2014.01.035 Figueiredo JL (2013) Functionalization of porous carbons for catalytic applications. J Mater Chem A 1:9351. https://doi.org/10.1039/c3ta10876g Rocha RP, Pereira MFR, Figueiredo JL (2013) Carbon as a catalyst: esterification of acetic acid with ethanol. Catal Today 218–219:51–56. https://doi.org/10.1016/j.cattod.2013.09.049 Ishii T, Kashihara S, Hoshikawa Y, Ozaki JI, Kannari N, Takai K, Enoki T, Kyotani T (2014) A quantitative analysis of carbon edge sites and an estimation of graphene sheet size in high-temperature treated, non-porous carbons. Carbon N Y 80:135–145. https://doi.org/10.1016/j.carbon.2014.08.048 Lokman IM, Rashid U, Taufiq-Yap YH (2016) Meso- and macroporous sulfonated starch solid acid catalyst for esterification of palm fatty acid distillate. Arab J Chem 9:179–189. https://doi.org/10.1016/j.arabjc.2015.06.034 Dosuna-Rodríguez I, Adriany C, Gaigneaux EM (2011) Glycerol acetylation on sulphated zirconia in mild conditions. Catal Today 167:56–63. https://doi.org/10.1016/j.cattod.2010.11.057 Figueiredo JL, Pereira MFR (2013) Synthesis and functionalization of carbon xerogels to be used as supports for fuel cell catalysts. J Energy Chem 22:195–201. https://doi.org/10.1016/S2095-4956(13)60025-X Boehm HP (2002) Surface oxides on carbon and their analysis: a critical assessment. Carbon N Y 40:145–149. https://doi.org/10.1016/S0008-6223(01)00165-8 Konwar LJ, Mäki-Arvela P, Salminen E, Kumar N, Thakur AJ, Mikkola JP, Deka D (2015) Towards carbon efficient biorefining: multifunctional mesoporous solid acids obtained from biodiesel production wastes for biomass conversion. Appl Catal B Environ 176–177:20–35. https://doi.org/10.1016/j.apcatb.2015.03.005 Li M, Chen D, Zhu X (2013) Preparation of solid acid catalyst from rice husk char and its catalytic performance in esterification. Cuihua Xuebao/Chinese J Catal 34:1674–1682. https://doi.org/10.1016/s1872-2067(12)60634-2 Kastner JR, Miller J, Geller DP, Locklin J, Keith LH, Johnson T (2012) Catalytic esterification of fatty acids using solid acid catalysts generated from biochar and activated carbon. Catal Today 190:122–132. https://doi.org/10.1016/j.cattod.2012.02.006 Jain A, Balasubramanian R, Srinivasan MP (2016) Hydrothermal conversion of biomass waste to activated carbon with high porosity: a review. Chem Eng J 283:789–805. https://doi.org/10.1016/j.cej.2015.08.014 Zhang M, Sun A, Meng Y, Wang L, Jiang H, Li G (2015) High activity ordered mesoporous carbon-based solid acid catalyst for the esterification of free fatty acids. Microporous Mesoporous Mater 204:210–217. https://doi.org/10.1016/j.micromeso.2014.11.027 Primo A, Forneli A, Corma A, García H (2012) From biomass wastes to highly efficient CO2 adsorbents: graphitisation of chitosan and alginate biopolymers. ChemSusChem 5:2207–2214. https://doi.org/10.1002/cssc.201200366 Yu JT, Dehkhoda AM, Ellis N (2011) Development of biochar-based catalyst for transesterification of canola oil. Energy Fuel 25:337–344. https://doi.org/10.1021/ef100977d Konwar LJ, Das R, Thakur AJ, Salminen E, Mäki-Arvela P, Kumar N, Mikkola JP, Deka D (2014) Biodiesel production from acid oils using sulfonated carbon catalyst derived from oil-cake waste. J Mol Catal A Chem 388–389:167–176. https://doi.org/10.1016/j.molcata.2013.09.031 Zhou L, Dong B, Tang S, Ma H, Chen C, Yang X, Xu J (2013) Sulfonated carbon catalyzed oxidation of aldehydes to carboxylic acids by hydrogen peroxide. J Energy Chem 22:659–664. https://doi.org/10.1016/S2095-4956(13)60087-X Ezebor F, Khairuddean M, Abdullah AZ, Boey PL (2014) Oil palm trunk and sugarcane bagasse derived solid acid catalysts for rapid esterification of fatty acids and moisture-assisted transesterification of oils under pseudo-infinite methanol. Bioresour Technol 157:254–262. https://doi.org/10.1016/j.biortech.2014.01.110 Konwar LJ, Mäki-Arvela P, Begum P, Kumar N, Thakur AJ, Mikkola JP, Deka RC, Deka D (2015) Shape selectivity and acidity effects in glycerol acetylation with acetic anhydride : selective synthesis of triacetin over Y-zeolite and sulfonated mesoporous carbons. J Catal 329:237–247. https://doi.org/10.1016/j.jcat.2015.05.021 Donald J, Ohtsuka Y, Xu CC (2011) Effects of activation agents and intrinsic minerals on pore development in activated carbons derived from a Canadian peat. Mater Lett 65:744–747. https://doi.org/10.1016/j.matlet.2010.11.049 Wong S, Lee Y, Ngadi N, Inuwa IM, Mohamed NB (2018) Synthesis of activated carbon from spent tea leaves for aspirin removal. Chin J Chem Eng 26:1003–1011. https://doi.org/10.1016/j.cjche.2017.11.004 Lee CL, H’ng PS, Chin KL et al (2019) Characterization of bioadsorbent produced using incorporated treatment of chemical and carbonization procedures. R Soc Open Sci:6. https://doi.org/10.1098/rsos.190667 Chen HY, Cui ZW (2016) A microwave-sensitive solid acid catalyst prepared from sweet potato via a simple method. Catalysts:6. https://doi.org/10.3390/catal6120211 Geng L, Yu G, Wang Y, Zhu Y (2012) Ph-SO 3 H-modified mesoporous carbon as an efficient catalyst for the esterification of oleic acid. Appl Catal A Gen 427–428:137–144. https://doi.org/10.1016/j.apcata.2012.03.044 Thommes M, Kaneko K, Neimark AV, Olivier JP, Rodriguez-Reinoso F, Rouquerol J, Sing KSW (2015) Physisorption of gases, with special reference to the evaluation of surface area and pore size distribution (IUPAC Technical Report). Pure Appl Chem 87:1051–1069. https://doi.org/10.1515/pac-2014-1117 Zeng D, Zhang Q, Chen S, Liu S, Wang G (2016) Synthesis porous carbon-based solid acid from rice husk for esterification of fatty acids. Microporous Mesoporous Mater 219:54–58. https://doi.org/10.1016/j.micromeso.2015.07.028 Malins K, Brinks J, Kampars V, Malina I (2016) Esterification of rapeseed oil fatty acids using a carbon-based heterogeneous acid catalyst derived from cellulose. Appl Catal A Gen 519:99–106. https://doi.org/10.1016/j.apcata.2016.03.020 Kitano M, Arai K, Kodama A, Kousaka T, Nakajima K, Hayashi S, Hara M (2009) Preparation of a sulfonated porous carbon catalyst with high specific surface area. Catal Lett 131:242–249. https://doi.org/10.1007/s10562-009-0062-4 Ouyang S, Kuang X, Xu Q, Yin D (2014) Preparation of a carbon-based solid acid with high acid density via a novel method. J Mater Sci Chem Eng 02:4–8. https://doi.org/10.4236/msce.2014.26002 Santos EM, Teixeira APDC, Da Silva FG et al (2015) New heterogeneous catalyst for the esterification of fatty acid produced by surface aromatization/sulfonation of oilseed cake. Fuel 150:408–414. https://doi.org/10.1016/j.fuel.2015.02.027 Nagasundaram N, Kokila M, Sivaguru P, Santhosh R, Lalitha A (2020) SO3H@carbon powder derived from waste orange peel: an efficient, nano-sized greener catalyst for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives. Adv Powder Technol. https://doi.org/10.1016/j.apt.2020.01.012 Omri A, Benzina M (2012) Characterization of activated carbon prepared from a new raw lignocellulosic material : Ziziphus spina-christi seeds. J Soc Chim Tunis 14:175–183 Zhu S, Zhu Y, Gao X, Mo T, Zhu Y, Li Y (2013) Production of bioadditives from glycerol esterification over zirconia supported heteropolyacids. Bioresour Technol 130:45–51. https://doi.org/10.1016/j.biortech.2012.12.011 Tao ML, Guan HY, Wang XH, Liu YC, Louh RF (2015) Fabrication of sulfonated carbon catalyst from biomass waste and its use for glycerol esterification. Fuel Process Technol 138:355–360. https://doi.org/10.1016/j.fuproc.2015.06.021 Kim I, Kim J, Lee D (2014) Environmental A comparative study on catalytic properties of solid acid catalysts for glycerol acetylation at low temperatures. Appl Catal B Environ 148–149:295–303. https://doi.org/10.1016/j.apcatb.2013.11.008 Zhou L, Al-zaini E, Adesina AA (2013) Catalytic characteristics and parameters optimization of the glycerol acetylation over solid acid catalysts. Fuel 103:617–625. https://doi.org/10.1016/j.fuel.2012.05.042