Green and Efficient Modification of Grape Seed Oil to Synthesize Renewable Monomers

Gaglieri, Caroline; Alarcon, Rafael T; Moura, Aniele de; Magri, Raquel; Silva-Filho, Luiz C. da; Bannach, Gilbert

doi:10.21577/0103-5053.20210104

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Journal of the Brazilian Chemical Society

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Article • J. Braz. Chem. Soc. 32 (11) • 2021 • https://doi.org/10.21577/0103-5053.20210104 copy

Green and Efficient Modification of Grape Seed Oil to Synthesize Renewable Monomers

Authorship SCIMAGO INSTITUTIONS RANKINGS

Grape seed is a waste product from the wine and juice industries. However, vegetable oil can be extracted from it, which is a renewable chemical with a huge potential application after chemical modifications, such as epoxidation and maleinization processes. This paper therefore deals with the use of grape seed oil, to produce its epoxidized and maleinized derivatives. Both derivatives were synthesized in order to improve the conversion (99.4%), yield (98.9%) and selectivity (99.5%) values, as well as to decrease the reaction time (3 h) using cleaner energy sources and heterogeneous catalysts, which can be used 4× without regeneration and obtaining similar conversion and yield values, and at least 5× keeping high selectivity. Based on the characterization results, both grape seed oil derivatives may be applied in different fields, including polymer chemistry as a monomer, coating, and paint. In addition, they can be an option to industries that use petrochemical derivatives as precursors.

Keywords:
renewable chemicals; maleinization reaction; epoxidized derivatives; microwave synthesis; Amberlite-IR120 reusability

	This work	Reference 18	Reference 22	Reference 23	Reference 24	Reference 25^b a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.
Conversion / %	99.4	not complete^a a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	ca. 45%^c a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	-^b a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	-^b a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	93.5^g a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.
Yield / %	98.9	-^b a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	8.31	86	85	74.2^g a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.
Selectivity / %	99.5	-^b a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	ca. 20%^c a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	-^b a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	-^b a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	79.4^g a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.
n_C=C:n_H2O2:n_AA	1:6:1	1:1.5:0.5	1:6:0.3^d a It was not demonstrated the exact value, however by MIR spectra it was possible to observe residual C=C bonds; bit was not described in the paper and it was not possible to calculated it with the provided data; cobtained in a graph, the authors did not write the exact value; dmolar proportion between nC=C: nH2O2:nNa2CO3; ehexadecyltrimethyl-ammonium bromide; fsupercritical conditions; gcalculated based on results provided by the authors.	1:8:0.5	1:10:0.5	1:2:0.5
Temperature / °C	60	55	40	80	55/65	90
time / h	3	24	15	overnight	5/1	1
Pressure / atm	1	1	148	1	1	1
Catalyst	heterogeneous/Amberlite^® IR120	heterogeneous/Amberlite^® IR120	heterogeneous/HDTMAB^e	heterogeneous/Amberlite^® IR120	homogeneous/ H₂SO₄	homogeneous/ H₂SO₄
Solvent	no	yes/toluene	yes/CO₂^f	no	no	no
Heating type	conventional	conventional	conventional	conventional	conventional	conventional

	Method	GSO	EGSO	MGSO
IV / (g I₂ per 100 g of sample)	¹H NMR	122.97	0	69.31
IV / (g I₂ per 100 g of sample)	titration	121.58 ± 0.86	0.78 ± 0.25	62.54 ± 0.79
DB_average per triglyceride molecule		4.3	0	2.2

Temperature / °C	27	40	60	80
η_GSO / (mPa s)	46.02 ± 2.8	27.40 ± 0.15	15.00 ± 0.10	8.91 ± 0.09
η_EGSO / (mPa s)	336.91 ± 1.16	128.92 ± 0.36	68.08 ± 0.34	32.54 ± 0.70
η_MGSO / (mPa s)	8792 ± 20.19	2353.57 ± 2.64	609.03 ± 0.53	220.97 ± 0.3

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[1] *e-mail: gilbert.bannach@unesp.br