Renewable glycoaldehyde isolation from pyrolysis oil by reactive extraction with primary amines

C.R. Vitasari, G.W. Meindersma, A.B. Haan, de

Research output: Chapter in Book/Report/Conference proceedingConference contributionAcademicpeer-review

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Abstract

The transition to a sustainable bio-based economy has rapidly increased the interest to obtain renewable platform chemicals from biomass. Glycolaldehyde is one of potential future platform chemicals, which is present in high quantity (5–13 wt%) in wood-derived pyrolysis oil. Water addition to pyrolysis oil isolates glycolaldehyde and other polar compounds, nearly quantitatively in the aqueous phase. In order to apply extraction for the subsequent glycolaldehyde recovery a water-insoluble solvent is required. This work was done to identify a suitable solvent. Firstly, several long chain alkanes and alcohols were evaluated by extracting an aqueous solution of 6.2 wt% glycolaldehyde. The results demonstrated that alkanes cannot extract glycolaldehyde whereas the distribution coefficient of glycolaldehyde in alcohols decreases with chain length, from 0.23 for 1-octanol to 0.04 for oleyl alcohol. Due to low distribution coefficients, primary amines were considered extractants since they can form reversible imines with aldehydes. A solution of 1 M Primene JM-T in 1-octanol and pure Primene JM-T increases the distribution coefficient of glycolaldehyde in 1-octanol by a factor of 10 and 75, respectively. The extraction factors are 0.46 for 1-octanol, 3.79 for 1 M Primene JM-T in 1-octanol and 30.87 for pure Primene JM-T. Another alternative is aniline derivatives. At a concentration of 1 M, 4-ethylaniline gives more than two orders of magnitude higher distribution ratio than 2-ethylaniline and Primene JM-T. The extraction capability of amines is: octylamine >4-ethylaniline >phenylethylamine >>Primene JM-T >2-ethylaniline. In conclusion, highly branched primary amines and orthoalkylanilines are promising extractants, taking into account the reversibility of the Schiff base formation. The final selection of the most suitable extractant/diluent combination will depend on the actual selectivity towards glycolaldehyde and back-extraction yield.
Original languageEnglish
Title of host publicationProceedings of the 19th International Solvent Extraction Conference - ISEC 2011, 3-7 October 2011, Santiago, Chile
Pages1-7
Publication statusPublished - 2011
Event19th International Solvent Extraction Conference (ISEC 2011), October 3-7, 2011, Santiago, Chile - Santiago, Chile
Duration: 3 Oct 20117 Oct 2011
https://gecamin.com/isec2011/index.php?option=com_content&view=frontpage&Itemid=1&lang=en

Conference

Conference19th International Solvent Extraction Conference (ISEC 2011), October 3-7, 2011, Santiago, Chile
Abbreviated titleISEC 2011
CountryChile
CitySantiago
Period3/10/117/10/11
Internet address

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primary amines
octanol
pyrolysis
oils
alkanes
alcohols
phenethylamines
polar compounds
aniline
amines
aldehydes
water
chemical derivatives
biomass
extracts

Cite this

Vitasari, C. R., Meindersma, G. W., & Haan, de, A. B. (2011). Renewable glycoaldehyde isolation from pyrolysis oil by reactive extraction with primary amines. In Proceedings of the 19th International Solvent Extraction Conference - ISEC 2011, 3-7 October 2011, Santiago, Chile (pp. 1-7)
Vitasari, C.R. ; Meindersma, G.W. ; Haan, de, A.B. / Renewable glycoaldehyde isolation from pyrolysis oil by reactive extraction with primary amines. Proceedings of the 19th International Solvent Extraction Conference - ISEC 2011, 3-7 October 2011, Santiago, Chile. 2011. pp. 1-7
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abstract = "The transition to a sustainable bio-based economy has rapidly increased the interest to obtain renewable platform chemicals from biomass. Glycolaldehyde is one of potential future platform chemicals, which is present in high quantity (5–13 wt{\%}) in wood-derived pyrolysis oil. Water addition to pyrolysis oil isolates glycolaldehyde and other polar compounds, nearly quantitatively in the aqueous phase. In order to apply extraction for the subsequent glycolaldehyde recovery a water-insoluble solvent is required. This work was done to identify a suitable solvent. Firstly, several long chain alkanes and alcohols were evaluated by extracting an aqueous solution of 6.2 wt{\%} glycolaldehyde. The results demonstrated that alkanes cannot extract glycolaldehyde whereas the distribution coefficient of glycolaldehyde in alcohols decreases with chain length, from 0.23 for 1-octanol to 0.04 for oleyl alcohol. Due to low distribution coefficients, primary amines were considered extractants since they can form reversible imines with aldehydes. A solution of 1 M Primene JM-T in 1-octanol and pure Primene JM-T increases the distribution coefficient of glycolaldehyde in 1-octanol by a factor of 10 and 75, respectively. The extraction factors are 0.46 for 1-octanol, 3.79 for 1 M Primene JM-T in 1-octanol and 30.87 for pure Primene JM-T. Another alternative is aniline derivatives. At a concentration of 1 M, 4-ethylaniline gives more than two orders of magnitude higher distribution ratio than 2-ethylaniline and Primene JM-T. The extraction capability of amines is: octylamine >4-ethylaniline >phenylethylamine >>Primene JM-T >2-ethylaniline. In conclusion, highly branched primary amines and orthoalkylanilines are promising extractants, taking into account the reversibility of the Schiff base formation. The final selection of the most suitable extractant/diluent combination will depend on the actual selectivity towards glycolaldehyde and back-extraction yield.",
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year = "2011",
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Vitasari, CR, Meindersma, GW & Haan, de, AB 2011, Renewable glycoaldehyde isolation from pyrolysis oil by reactive extraction with primary amines. in Proceedings of the 19th International Solvent Extraction Conference - ISEC 2011, 3-7 October 2011, Santiago, Chile. pp. 1-7, 19th International Solvent Extraction Conference (ISEC 2011), October 3-7, 2011, Santiago, Chile, Santiago, Chile, 3/10/11.

Renewable glycoaldehyde isolation from pyrolysis oil by reactive extraction with primary amines. / Vitasari, C.R.; Meindersma, G.W.; Haan, de, A.B.

Proceedings of the 19th International Solvent Extraction Conference - ISEC 2011, 3-7 October 2011, Santiago, Chile. 2011. p. 1-7.

Research output: Chapter in Book/Report/Conference proceedingConference contributionAcademicpeer-review

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AU - Haan, de, A.B.

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N2 - The transition to a sustainable bio-based economy has rapidly increased the interest to obtain renewable platform chemicals from biomass. Glycolaldehyde is one of potential future platform chemicals, which is present in high quantity (5–13 wt%) in wood-derived pyrolysis oil. Water addition to pyrolysis oil isolates glycolaldehyde and other polar compounds, nearly quantitatively in the aqueous phase. In order to apply extraction for the subsequent glycolaldehyde recovery a water-insoluble solvent is required. This work was done to identify a suitable solvent. Firstly, several long chain alkanes and alcohols were evaluated by extracting an aqueous solution of 6.2 wt% glycolaldehyde. The results demonstrated that alkanes cannot extract glycolaldehyde whereas the distribution coefficient of glycolaldehyde in alcohols decreases with chain length, from 0.23 for 1-octanol to 0.04 for oleyl alcohol. Due to low distribution coefficients, primary amines were considered extractants since they can form reversible imines with aldehydes. A solution of 1 M Primene JM-T in 1-octanol and pure Primene JM-T increases the distribution coefficient of glycolaldehyde in 1-octanol by a factor of 10 and 75, respectively. The extraction factors are 0.46 for 1-octanol, 3.79 for 1 M Primene JM-T in 1-octanol and 30.87 for pure Primene JM-T. Another alternative is aniline derivatives. At a concentration of 1 M, 4-ethylaniline gives more than two orders of magnitude higher distribution ratio than 2-ethylaniline and Primene JM-T. The extraction capability of amines is: octylamine >4-ethylaniline >phenylethylamine >>Primene JM-T >2-ethylaniline. In conclusion, highly branched primary amines and orthoalkylanilines are promising extractants, taking into account the reversibility of the Schiff base formation. The final selection of the most suitable extractant/diluent combination will depend on the actual selectivity towards glycolaldehyde and back-extraction yield.

AB - The transition to a sustainable bio-based economy has rapidly increased the interest to obtain renewable platform chemicals from biomass. Glycolaldehyde is one of potential future platform chemicals, which is present in high quantity (5–13 wt%) in wood-derived pyrolysis oil. Water addition to pyrolysis oil isolates glycolaldehyde and other polar compounds, nearly quantitatively in the aqueous phase. In order to apply extraction for the subsequent glycolaldehyde recovery a water-insoluble solvent is required. This work was done to identify a suitable solvent. Firstly, several long chain alkanes and alcohols were evaluated by extracting an aqueous solution of 6.2 wt% glycolaldehyde. The results demonstrated that alkanes cannot extract glycolaldehyde whereas the distribution coefficient of glycolaldehyde in alcohols decreases with chain length, from 0.23 for 1-octanol to 0.04 for oleyl alcohol. Due to low distribution coefficients, primary amines were considered extractants since they can form reversible imines with aldehydes. A solution of 1 M Primene JM-T in 1-octanol and pure Primene JM-T increases the distribution coefficient of glycolaldehyde in 1-octanol by a factor of 10 and 75, respectively. The extraction factors are 0.46 for 1-octanol, 3.79 for 1 M Primene JM-T in 1-octanol and 30.87 for pure Primene JM-T. Another alternative is aniline derivatives. At a concentration of 1 M, 4-ethylaniline gives more than two orders of magnitude higher distribution ratio than 2-ethylaniline and Primene JM-T. The extraction capability of amines is: octylamine >4-ethylaniline >phenylethylamine >>Primene JM-T >2-ethylaniline. In conclusion, highly branched primary amines and orthoalkylanilines are promising extractants, taking into account the reversibility of the Schiff base formation. The final selection of the most suitable extractant/diluent combination will depend on the actual selectivity towards glycolaldehyde and back-extraction yield.

M3 - Conference contribution

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EP - 7

BT - Proceedings of the 19th International Solvent Extraction Conference - ISEC 2011, 3-7 October 2011, Santiago, Chile

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Vitasari CR, Meindersma GW, Haan, de AB. Renewable glycoaldehyde isolation from pyrolysis oil by reactive extraction with primary amines. In Proceedings of the 19th International Solvent Extraction Conference - ISEC 2011, 3-7 October 2011, Santiago, Chile. 2011. p. 1-7