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Erschienen in: Clean Technologies and Environmental Policy 5/2016

27.02.2016 | Original Paper

Enhancing the biodiesel manufacturing process by use of glycerin to produce hyacinth fragrance

verfasst von: Cauê A. C. Silva, Flávia C. A. Figueiredo, Raphael Rodrigues, Mirela I. Sairre, Maraisa Gonçalves, Ines Matos, Isabel M. Fonseca, Dalmo Mandelli, Wagner A. Carvalho

Erschienen in: Clean Technologies and Environmental Policy | Ausgabe 5/2016

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Abstract

Oxidized and sulfonated-activated carbons (AC) were tested in the catalytic conversion of glycerol by acetalization reactions. The solids were treated with concentrated nitric acid and/or fuming sulfuric acid (AC, AC-N, AC-S, and AC-NS). The presence of sulfur and an increase in the acidity of the solids demonstrate the suitability of the oxidation as well as the sulfonation process, especially in the sample treated with concentrated nitric acid and fuming sulfuric acid (AC-NS). The best catalyst for the reaction of glycerol acetalization with phenylacetaldehyde was AC-NS, with a phenylacetaldehyde conversion of 95 % after 90 min at 383 K and selectivity of 88 and 12 %, respectively, to dioxolane and dioxane. These products can be used as hyacinth fragrance flavoring compounds. Furthermore, a contribution of homogeneous catalysis in these systems was not identified. Thus, we identified a possibility of glycerol conversion, a biodiesel by-product, into value-added products by suitable catalysts produced from activated carbons.

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Literatur
Zurück zum Zitat de Araujo Filho CA, Salmi T, Bernas A, Mikkola JP (2013) Kinetic Model for Homogeneously Catalyzed Halogenation of Glycerol. Ind Eng Chem Res 52:1523–1530. doi:10.1021/ie302610v CrossRef de Araujo Filho CA, Salmi T, Bernas A, Mikkola JP (2013) Kinetic Model for Homogeneously Catalyzed Halogenation of Glycerol. Ind Eng Chem Res 52:1523–1530. doi:10.​1021/​ie302610v CrossRef
Zurück zum Zitat Dean JA (1999) Binary Azeotropic (Constant-Boiling) Mixtures. In: Perry RH, Green DW (eds) Lange’s handbook of chemistry, 15th edn. McGraw-Hill, New York Dean JA (1999) Binary Azeotropic (Constant-Boiling) Mixtures. In: Perry RH, Green DW (eds) Lange’s handbook of chemistry, 15th edn. McGraw-Hill, New York
Zurück zum Zitat Faria RPV, Pereira CSM, Silva VMTM, Loureiro JM, Rodrigues AE (2013a) Glycerol valorisation as biofuels: selection of a suitable solvent for an innovative process for the synthesis of GEA. Chem Eng J 233:159–167. doi:10.1016/j.cej.2013.08.035 CrossRef Faria RPV, Pereira CSM, Silva VMTM, Loureiro JM, Rodrigues AE (2013a) Glycerol valorisation as biofuels: selection of a suitable solvent for an innovative process for the synthesis of GEA. Chem Eng J 233:159–167. doi:10.​1016/​j.​cej.​2013.​08.​035 CrossRef
Zurück zum Zitat Faria RPV, Pereira CSM, Silva VMTM, Loureiro JM, Rodrigues AE (2013b) Glycerol Valorization as Biofuel: thermodynamic and Kinetic Study of the Acetalization of Glycerol with Acetaldehyde. Ind Eng Chem Res 52:1538–1547. doi:10.1021/ie302935w CrossRef Faria RPV, Pereira CSM, Silva VMTM, Loureiro JM, Rodrigues AE (2013b) Glycerol Valorization as Biofuel: thermodynamic and Kinetic Study of the Acetalization of Glycerol with Acetaldehyde. Ind Eng Chem Res 52:1538–1547. doi:10.​1021/​ie302935w CrossRef
Zurück zum Zitat Ferreira ACS, Barbe J-C, Bertrand A (2002) Heterocyclic acetals from glycerol and acetaldehyde in Port wines: evolution with aging. J Agric Food Chem 50:2560–2564. doi:10.1021/jf011391j CrossRef Ferreira ACS, Barbe J-C, Bertrand A (2002) Heterocyclic acetals from glycerol and acetaldehyde in Port wines: evolution with aging. J Agric Food Chem 50:2560–2564. doi:10.​1021/​jf011391j CrossRef
Zurück zum Zitat Galhardo TS, Simone N, Gonçalves M, Figueiredo FCA, Mandelli D, Carvalho WA (2013) Preparation of sulfonated carbons from rice husk and their application in catalytic conversion of glycerol. ACS Sustain Chem Eng 1:1381–1389. doi:10.1021/sc400117t CrossRef Galhardo TS, Simone N, Gonçalves M, Figueiredo FCA, Mandelli D, Carvalho WA (2013) Preparation of sulfonated carbons from rice husk and their application in catalytic conversion of glycerol. ACS Sustain Chem Eng 1:1381–1389. doi:10.​1021/​sc400117t CrossRef
Zurück zum Zitat Gelosa D, Ramaioli M, Valente G, Morbidelli M (2003) Chromatographic reactors: esterification of glycerol with acetic acid using acidic polymeric resins. Ind Eng Chem Res 42:6536–6544. doi:10.1021/ie030292n CrossRef Gelosa D, Ramaioli M, Valente G, Morbidelli M (2003) Chromatographic reactors: esterification of glycerol with acetic acid using acidic polymeric resins. Ind Eng Chem Res 42:6536–6544. doi:10.​1021/​ie030292n CrossRef
Zurück zum Zitat Gonçalves M, Souza VC, Galhardo TS, Mantovani M, Figueiredo FCA, Mandelli D, Carvalho WA (2013) Glycerol conversion catalyzed by carbons prepared from agroindustrial wastes. Ind Eng Chem Res 52:2832–2839. doi:10.1021/ie303072d CrossRef Gonçalves M, Souza VC, Galhardo TS, Mantovani M, Figueiredo FCA, Mandelli D, Carvalho WA (2013) Glycerol conversion catalyzed by carbons prepared from agroindustrial wastes. Ind Eng Chem Res 52:2832–2839. doi:10.​1021/​ie303072d CrossRef
Zurück zum Zitat Gordobil O, Moriana R, Zhang L, Labidi J, Sevastyanova O (2016) Assesment of technical lignins for uses in biofuels and biomaterials: structure-related properties, proximate analysis and chemical modification. Ind Crop Prod 83:155–165. doi:10.1016/j.indcrop.2015.12.048 CrossRef Gordobil O, Moriana R, Zhang L, Labidi J, Sevastyanova O (2016) Assesment of technical lignins for uses in biofuels and biomaterials: structure-related properties, proximate analysis and chemical modification. Ind Crop Prod 83:155–165. doi:10.​1016/​j.​indcrop.​2015.​12.​048 CrossRef
Zurück zum Zitat Gorgulho HF, Mesquita JP, Goncalves F, Pereira MFR, Figueiredo JL (2008) Characterization of the surface chemistry of carbon materials by potentiometric titrations and temperature-programmed desorption. Carbon 46:1544–1555. doi:10.1016/j.carbon.2008.06.045 CrossRef Gorgulho HF, Mesquita JP, Goncalves F, Pereira MFR, Figueiredo JL (2008) Characterization of the surface chemistry of carbon materials by potentiometric titrations and temperature-programmed desorption. Carbon 46:1544–1555. doi:10.​1016/​j.​carbon.​2008.​06.​045 CrossRef
Zurück zum Zitat Güemez MB, Requies J, Agirre I, Arias PL, Barrio VL, Cambra JF (2013) Acetalization reaction between glycerol and n-butyraldehyde using an acidic ion exchange resin. Kinetic modelling. Chem Eng J 228:300–307. doi:10.1016/j.cej.2013.04.107 CrossRef Güemez MB, Requies J, Agirre I, Arias PL, Barrio VL, Cambra JF (2013) Acetalization reaction between glycerol and n-butyraldehyde using an acidic ion exchange resin. Kinetic modelling. Chem Eng J 228:300–307. doi:10.​1016/​j.​cej.​2013.​04.​107 CrossRef
Zurück zum Zitat Kaufhold M, El-Chahawi M (1996) Process for preparing acetaldehyde diethyl acetal. Germany Patent 5527969 Kaufhold M, El-Chahawi M (1996) Process for preparing acetaldehyde diethyl acetal. Germany Patent 5527969
Zurück zum Zitat Knübel G, Bomhard A, Schaper UA, Stalberg T, Markert T (1997) US Patent 5,670,670 Knübel G, Bomhard A, Schaper UA, Stalberg T, Markert T (1997) US Patent 5,670,670
Zurück zum Zitat Mandelli D, Carvalho WA, Shul’pina LS, Kirillov AM, Kirillova MV, Pombeiro AJ, Shul’pin GB (2013) Oxidation of glycerol with hydrogen peroxide catalyzed by metal complexes. In: Advances in organometallic chemistry and catalysis: the silver/gold jubilee international conference on organometallic chemistry celebratory book, Wiley, pp 247–257 Mandelli D, Carvalho WA, Shul’pina LS, Kirillov AM, Kirillova MV, Pombeiro AJ, Shul’pin GB (2013) Oxidation of glycerol with hydrogen peroxide catalyzed by metal complexes. In: Advances in organometallic chemistry and catalysis: the silver/gold jubilee international conference on organometallic chemistry celebratory book, Wiley, pp 247–257
Zurück zum Zitat Melero JA, Iglesias J, Morales G (2009) Heterogeneous acid catalysts for biodiesel production: current status and future challenges. Green Chem 11:1285–1308. doi:10.1039/B902086A CrossRef Melero JA, Iglesias J, Morales G (2009) Heterogeneous acid catalysts for biodiesel production: current status and future challenges. Green Chem 11:1285–1308. doi:10.​1039/​B902086A CrossRef
Zurück zum Zitat Moreno-Castilla C, Ferro-Garcia MA, Joly JP, Bautista-Toledo I, Carrasco-Marin F, Rivera-Atrilla J (1995) Activated carbon surface modifications by nitric-acid, hydrogen-peroxide, and ammonium peroxydisulfate treatments. Langmuir 11:4386–4392. doi:10.1021/la00011a035 CrossRef Moreno-Castilla C, Ferro-Garcia MA, Joly JP, Bautista-Toledo I, Carrasco-Marin F, Rivera-Atrilla J (1995) Activated carbon surface modifications by nitric-acid, hydrogen-peroxide, and ammonium peroxydisulfate treatments. Langmuir 11:4386–4392. doi:10.​1021/​la00011a035 CrossRef
Zurück zum Zitat Mota CJA, Silva CXA, Gonçalves VLC (2009) Gliceroquímica: novos produtos e processos a partir da glicerina de produção de biodiesel. Quim Nova 32:639–648CrossRef Mota CJA, Silva CXA, Gonçalves VLC (2009) Gliceroquímica: novos produtos e processos a partir da glicerina de produção de biodiesel. Quim Nova 32:639–648CrossRef
Zurück zum Zitat Neely BJ, Wagner J, Robinson RL Jr, Gasem KAM (2008) Mutual solubility measurements of hydrocarbon-water systems containing benzene, toluene, and 3-methylpentane. J Chem Eng Data 53:165–174. doi:10.1021/je700449z CrossRef Neely BJ, Wagner J, Robinson RL Jr, Gasem KAM (2008) Mutual solubility measurements of hydrocarbon-water systems containing benzene, toluene, and 3-methylpentane. J Chem Eng Data 53:165–174. doi:10.​1021/​je700449z CrossRef
Zurück zum Zitat Olivier JP, Conklin WB, Vonszombathely M (1994) Determination of pore-size distribution from density functional theory—a comparison of nitrogen and argon results. Characterization of porous solid III. Stud Surf Sci Catal 87:81–89. doi:10.1016/S0167-2991(08)63067-0 CrossRef Olivier JP, Conklin WB, Vonszombathely M (1994) Determination of pore-size distribution from density functional theory—a comparison of nitrogen and argon results. Characterization of porous solid III. Stud Surf Sci Catal 87:81–89. doi:10.​1016/​S0167-2991(08)63067-0 CrossRef
Zurück zum Zitat Ozbay N, Oktar N, Dogu G, Dogu T (2013) Activity comparison of different solid acid catalysts in Etherification of glycerol with tert-butyl alcohol in flow and batch reactors. Top Catal 56:1790–1803. doi:10.1007/s11244-013-0116-0 CrossRef Ozbay N, Oktar N, Dogu G, Dogu T (2013) Activity comparison of different solid acid catalysts in Etherification of glycerol with tert-butyl alcohol in flow and batch reactors. Top Catal 56:1790–1803. doi:10.​1007/​s11244-013-0116-0 CrossRef
Zurück zum Zitat Rodrigues R, Goncalves M, Mandelli D, Pescarmona PP, Carvalho WA (2014) Solvent-free conversion of glycerol to solketal catalysed by activated carbons functionalised with acid groups. Catal Sci Technol 4:2293–2301. doi:10.1039/C4CY00181H CrossRef Rodrigues R, Goncalves M, Mandelli D, Pescarmona PP, Carvalho WA (2014) Solvent-free conversion of glycerol to solketal catalysed by activated carbons functionalised with acid groups. Catal Sci Technol 4:2293–2301. doi:10.​1039/​C4CY00181H CrossRef
Zurück zum Zitat Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquerol J, Siemieniewska T (1985) Reporting physisorption data for gas solid systems with special reference to the determination of surface-area and porosity (recommendations 1984). Pure Appl Chem 57:603–619. doi:10.1351/pac198557040603 CrossRef Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquerol J, Siemieniewska T (1985) Reporting physisorption data for gas solid systems with special reference to the determination of surface-area and porosity (recommendations 1984). Pure Appl Chem 57:603–619. doi:10.​1351/​pac198557040603 CrossRef
Zurück zum Zitat Tao L-Z, Yan B, Liang Y, Xu B-Q (2013) Sustainable production of acrolein: catalytic performance of hydrated tantalum oxides for gas-phase dehydration of glycerol. Green Chem 15:696–705. doi:10.1039/c2gc16483c CrossRef Tao L-Z, Yan B, Liang Y, Xu B-Q (2013) Sustainable production of acrolein: catalytic performance of hydrated tantalum oxides for gas-phase dehydration of glycerol. Green Chem 15:696–705. doi:10.​1039/​c2gc16483c CrossRef
Zurück zum Zitat Verma S, Nasir Baig RB, Nadagouda MN, Varma RS (2016) Visible light mediated upgrading of biomass to biofuel. Green Chem. doi:10.1039/C5GC02951A Verma S, Nasir Baig RB, Nadagouda MN, Varma RS (2016) Visible light mediated upgrading of biomass to biofuel. Green Chem. doi:10.​1039/​C5GC02951A
Metadaten
Titel
Enhancing the biodiesel manufacturing process by use of glycerin to produce hyacinth fragrance
verfasst von
Cauê A. C. Silva
Flávia C. A. Figueiredo
Raphael Rodrigues
Mirela I. Sairre
Maraisa Gonçalves
Ines Matos
Isabel M. Fonseca
Dalmo Mandelli
Wagner A. Carvalho
Publikationsdatum
27.02.2016
Verlag
Springer Berlin Heidelberg
Erschienen in
Clean Technologies and Environmental Policy / Ausgabe 5/2016
Print ISSN: 1618-954X
Elektronische ISSN: 1618-9558
DOI
https://doi.org/10.1007/s10098-016-1136-9

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