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

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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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Acknowledgments

This work was supported by FAPESP (Project No. 2013/211260-6 and 2011/22264-4) and CNPq (Project No. 441936/2014-8).

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Authors and Affiliations

  1. Centro de Ciências Naturais e Humanas, Universidade Federal do ABC, Rua Santa Adélia, 166, Santo André, SP, CEP 09210-170, Brazil

    Cauê A. C. Silva, Flávia C. A. Figueiredo, Raphael Rodrigues, Mirela I. Sairre, Dalmo Mandelli & Wagner A. Carvalho

  2. Instituto de Ciência e Tecnologia, Universidade Federal de São Paulo, Rua Talim, 330, São José dos Campos, SP, CEP 12231-280, Brazil

    Maraisa Gonçalves

  3. REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Campus da Caparica, 2829-516, Caparica, Portugal

    Ines Matos & Isabel M. Fonseca

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  1. Cauê A. C. Silva
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  2. Flávia C. A. Figueiredo
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  3. Raphael Rodrigues
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  4. Mirela I. Sairre
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  5. Maraisa Gonçalves
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  9. Wagner A. Carvalho
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Corresponding author

Correspondence to Wagner A. Carvalho.

Electronic supplementary material

Below is the link to the electronic supplementary material. Characterization (textural analysis and TGA), 1H, and 13C NMR spectra of the products, glycerol acetalization reaction with PA using AC as catalyst, effect of reaction temperature, catalyst stability, and recycling are included.

10098_2016_1136_MOESM1_ESM.tif

Supplementary material 1 (TIFF 4080 kb) Nitrogen adsorption/desorption isotherms and pore diameter distribution of parent and treated AC samples

Supplementary material 2 (TIFF 8018 kb) Thermogravimetric analysis of AC, AC-N, AC-S and AC-NS catalysts

Supplementary material 3 (TIFF 7978 kb) Infrared spectra of AC, AC-N, AC-S and AC-NS catalysts

Supplementary material 4 (TIFF 8018 kb) 1H-NMR spectrum of products

Supplementary material 5 (TIFF 8545 kb) 13C-NMR spectra of products

10098_2016_1136_MOESM6_ESM.tif

Supplementary material 6 (TIFF 7978 kb) Glycerol acetalization reaction with PA using AC as catalyst (PA:glycerol molar ratio of 1:2, 383 K, 7.5 wt% catalyst)

10098_2016_1136_MOESM7_ESM.tif

Supplementary material 7 (TIFF 7978 kb) Effect of reaction temperature in the glycerol acetalization reaction with PA using AC-NS as catalyst (PA:glycerol molar ratio of 1:2, 7.5 wt% catalyst)

10098_2016_1136_MOESM8_ESM.tif

Supplementary material 8 (TIFF 8078 kb) Glycerol acetalization reaction with PA using AC-NS as catalyst as function of time and after catalyst separation from the reaction medium (PA:glycerol molar ratio of 1:2, 383 K, 7.5 wt% catalyst)

10098_2016_1136_MOESM9_ESM.tif

Supplementary material 9 (TIFF 8078 kb) Glycerol acetalization reaction with PA using AC-NS as catalyst in different use cycles (PA:glycerol molar ratio of 1:2, 383 K, 7.5 wt% catalyst)

10098_2016_1136_MOESM10_ESM.tif

Supplementary material 10 (TIFF 34811 kb) GC profile of Cycles 1, 2 and 3 of glycerol acetalization reaction with PA using AC-NS as catalyst (PA:glycerol molar ratio of 1:2, 383 K, 7.5 wt% catalyst)

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Silva, C.A.C., Figueiredo, F.C.A., Rodrigues, R. et al. Enhancing the biodiesel manufacturing process by use of glycerin to produce hyacinth fragrance. Clean Techn Environ Policy 18, 1551–1563 (2016). https://doi.org/10.1007/s10098-016-1136-9

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