Fusel Oil: Chemical Composition and an Overview of Its Potential Application

Massa, Thainara B.; Raspe, Djéssica T.; Feiten, Mirian C.; Cardozo-Filho, Lúcio; Silva, Camila da

doi:10.21577/0103-5053.20220145

Thainara B. Massa

Programa de Pós-Graduação em Engenharia Química, Universidade Estadual de Maringá, 87020-900 Maringá-PR, Brazil

https://orcid.org/0000-0002-1733-4547

Djéssica T. Raspe

Programa de Pós-Graduação em Agronomia, Universidade Estadual de Maringá, 87020-900 Maringá-PR, Brazil

https://orcid.org/0000-0003-1173-8636

Mirian C. Feiten

Departamento de Tecnologia, Universidade Estadual de Maringá, 87506-370 Umuarama-PR, Brazil

https://orcid.org/0000-0001-9522-7168

Lúcio Cardozo-Filho

Programa de Pós-Graduação em Engenharia Química, Universidade Estadual de Maringá, 87020-900 Maringá-PR, Brazil

https://orcid.org/0000-0002-1764-9979

Camila da Silva ^**e-mail: camiladasilva.eq@gmail.com

Programa de Pós-Graduação em Engenharia Química, Universidade Estadual de Maringá, 87020-900 Maringá-PR, Brazil

Departamento de Tecnologia, Universidade Estadual de Maringá, 87506-370 Umuarama-PR, Brazil

https://orcid.org/0000-0002-7989-7046

*e-mail: camiladasilva.eq@gmail.com

Editor handled this article: Albertina Moglioni (Associate)

Thainara Bovo Massa is Food Engineer, Master in Chemical Engineering, and PhD student in chemical engineering, at the State University of Maringá, Paraná, Brazil. She has experience in the area of food science and technology, with an emphasis on food engineering.

Djéssica Tatiane Raspe is Food Technologist, Master in Bioenergy, PhD in Food Science, State University of Maringá, Paraná, Brazil. She is currently doing a Post-doc in Agronomy as a fellow of the Conselho Nacional de Desenvolvimento Científico e Tecnológico. She has experience in Food Science and Technology, with an emphasis in the same area, working mainly with unconventional processes of modification of oils and fats and extraction of natural compounds from plant matrices.

Mirian Cristina Feiten is Food Engineer, Master, and PhD in Food Engineering. Currently, she is professor at the State University of Maringá, Paraná, Brazil. She has experience in Food Engineering, with an emphasis on processes development in the food industry, have been acting mainly on the following topics: emerging technologies, biocatalysis, development of new products, sensory analysis of food, and protein structural biochemistry.

Lúcio Cardozo Filho is Chemical Engineer, Master in Chemical Engineering, and PhD in Food Engineering. Currently, he is professor at the State University of Maringá, Paraná, Brazil. He has experience in chemical engineering, with emphasis on pressurized fluid technology, working mainly on the following topics: supercritical extraction, phase equilibrium, supercritical water, and thermodynamic analysis, as well as in the development of products, processes, and equipment.

Camila da Silva is Chemical Engineer, Master in Food Engineering, PhD in Chemical Engineering. Currently, she is professor at the State University of Maringá, Paraná, Brazil. She has experience in Engineering, with emphasis on chemical engineering and food engineering, working mainly on the following topics: processes in pressurized medium, ultrasound-assisted processes, biodiesel, and extraction of compounds from natural sources.

Country	Composition of fusel oil / wt.%								Reference
Country	Isoamyl alcohol	Ethanol	Isobutanol	Propanol	Butanol	Pentanol	Methanol	Water	Reference
Canada	70.85	3.44	nr	nr	nr	nr	nr	9.96	Montoya et al.⁹9 Montoya, N.; Durán, J.; Córdoba, F.; Gil, I.; Trujillo, C.; Rodríguez, G.; Ing. Invest. 2016, 36, 21. [Crossref]
Brazil	57.65	16.22	6.04	2.18	1.00	nr	nr	14.70	Dias et al.¹⁰10 Dias, A. L. B.; da Cunha, G. N.; dos Santos, P.; Meireles, M. A.; Martínez, J.; J. Supercrit. Fluids 2018, 142, 22. [Crossref]
Turkey	74.70	1.10	11.30	3.80	4.90	nr	nr	4.10	Sozen et al.¹¹11 Sozen, A.; Menlik, T.; Guru, M.; Aktas, M.; Heat Mass Transfer 2017, 53, 141. [Crossref]
Colombia	70.40	12.06	1.30	nr	1.40	nr	nr	14.30	Mendoza-Pedroza et al.¹²12 Mendoza-Pedroza, J. J.; Sánchez-Ramírez, E.; Segovia-Hernández, J. G.; Hernández, S.; Orjuela, A.; Chem. Eng. Process. 2021, 163, 108329. [Crossref]
Turkey	62.29	11.09	8.71	0.74	0.12	nr	nr	10.30	Simsek and Ozdalyan¹³13 Simsek, S.; Ozdalyan, B.; Energies 2018, 11, 625. [Crossref]
Brazil	53.72	8.35	6.47	0.90	0.50	0.003	nr	14.76	Ferreira et al.³³33 Ferreira, M. C.; Meirelles, A. J. A.; Batista, E. A.; Ind. Eng. Chem. Res. 2013, 52, 2336. [Crossref]
Brazil	49.13	11.44	6.53	0.76	0.54	0.02	0.03	16.40
Brazil	65.02	8.60	7.87	nr	nr	nr	nr	12.19	Li³⁸38 Li, H.; CN pat. 103980959, 2014.

Substrates/catalyst	Product	Result / %	Ideal conditions				Reference
Substrates/catalyst	Product	Result / %	Temperature / °C	R	C / wt.%	Reaction time / h	Reference
Acetic anhydride and isoamyl alcohol from FO/Lipozyme^® 435^a a Addition of supercritical CO2 to the reaction medium at 15 MPa;	isoamyl acetate	88.4 (isoamyl alcohol conversion)	60	2:1	2.5	1	Dias et al.¹⁴14 Dias, A. L. B.; Hatami, T.; Martínez, J.; Ciftci, O. N.; J. Supercrit. Fluids 2020, 164, 104917. [Crossref]
Acetic acid and FO/mesoporous silica KIT-6 functionalized with alkyl sulfonic acid	isoamyl acetate	95 (ester yield)	80	2:1	5	3	Tran et al.¹⁵15 Tran, T. T. V.; Kongparakul, S.; Karnjanakom, S.; Reubroycharoen, P.; Guan, G.; Chanlek, N.; Samart, C.; Mol. Catal. 2020, 484, 110724. [Crossref]
Butyric acid and FO/Candida rugosa	butyric esters	94.5 (esters yield)	30	1:2	10 mg mL^-1	24	Gamayurova et al.³⁶36 Gamayurova, V. S.; Shnaider, K. L.; Jamai, M. J.; Catal. Ind. 2017, 9, 85. [Crossref]
Lauric acid and FO/ Rhizopus oryzae lipase	isoamyl laurate	ca. 80 (lauric acid conversion)	45	1.5:1	11.65	24	Bôas et al.⁴³43 Bôas, R. N. B.; Ceron, A. A.; Bento, H. B. S.; de Castro, H. F.; Biomass Bioenergy 2018, 119, 61. [Crossref]
Acetic acid and isoamyl alcohol from FO/ Lipozyme^® 435	isoamyl acetate	92 (esterification percentage)	40	1:2	9	6	Bi et al.⁴⁷47 Bi, F.; Iqbal, S.; Ali, A.; Arman, M.; Hassan, M. U.; J. Chem. Soc. Pak. 2009, 31, 485.
Acetic acid and isoamyl alcohol from FO/cation-exchange resin H⁺ Amberlyst^® 15	isoamyl acetate	97 (ester yield)	120	1:1.2	3.2	1	Bandres et al.⁴⁸48 Bandres, M.; de Caro, P.; Thiebaud-Roux, S.; Borredon, M. E.; C. R. Chim. 2011, 14, 636. [Crossref]
Acetic anhydride and isoamyl alcohol from FO/cation-exchange resin H⁺ Amberlyst^® 15	isoamyl acetate	98 (ester yield)	120	1:2	1.6	2
Acetic anhydride and FO/Novozyme^® 435^b b addition of supercritical CO2 to the reaction medium at 10 MPa. FO: fusel oil; TL IM: Thermomyces lanuginosus immobilized; R: carboxylic acid to alcohol molar ratio; C: catalyst percentage in relation to substrate mass.	isoamyl acetate esters	95 (esterification yield)	40	2:1	1 g in a 10 mL-continuous reactor	1	Dias et al.⁴⁹49 Dias, A. L. B.; Ubeyitogullari, A.; Hatami, T.; Martínez, J.; Ciftci, O. N.; Chem. Eng. Res. Des. 2021, 176, 23. [Crossref]
Butyric acid and isoamyl alcohol from FO/Lipozyme^® TL IM	isoamyl butyrate	95.6 (esterification percentage)	45	1:2	11.25	18	Garcia⁵⁰50 Garcia, V.: Subproduto de Destilaria de Óleo Fúsel: Caracterização da Composição Química e Estudo de sua Aplicação Industrial; MSc Dissertation, Instituto Mauá de Tecnologia, São Caetano do Sul, Brazil, 2008. [Link] accessed in November 2022

Substrate	Catalyst	Product	Result / %	Ideal conditions				Reference
Substrate	Catalyst	Product	Result / %	Temperature / ºC	R	C / wt.%	t / h	Reference
Oleic acid and FO	Novozyme^® 435^a a Addition of ionic liquids to the reaction medium. FO: fusel oil; TL IM: Thermomyces lanuginosus immobilized; T: temperature; R: fatty acid or oil to FO molar ratio; C: catalyst percentage in relation to substrate mass; t: reaction time.	isoamyl oleate	ca. 100 (ester yield)	70	1:9	30	5	Bányai et al.¹⁶16 Bányai, T.; Bélafi-Bakó, K.; Nemestóthy, N.; Gubicza, L.; Hung. J. Ind. Chem. 2011, 39, 395. [Crossref]
Palm kernel oil and FO	Burkholderia cepacia	isoamyl esters	98 (esters yield)	45	1:4	22	8	Cérón et al.¹⁷17 Cérón, A. A.; Boas, R. N. V.; Biaggio, F. C.; de Castro, H. F.; Biomass Bioenergy 2018, 119, 166. [Crossref]
Waste cooking oil and FO	Novozyme^® 435	fatty acid esters	90 (esters yield)	40	1:3	14	24	Wang et al.¹⁸18 Wang, M.; Nie, K.; Yun, F.; Cao, H.; Deng, L.; Wang, F.; Tan, T.; Renewable Energy 2015, 83, 1020. [Crossref]
Babassu oil and isoamyl alcohol	potassium hydroxide	fatty acid esters	94 (esters yield)	25	1:10	2	1	Tebas et al.¹⁹19 Tebas, S. O. G.; Barañano, A. G.; Pinheiro, P. F.; Lacerda Jr., V.; Chem. Eng. Commun. 2021, 208, 432. [Crossref]
Triolein and FO	Pseudomonas cepacia	oleic acid alkyl esters	ca. 100 (triolein conversion)	40	1:3	1.5	6	Salis et al.⁵⁸58 Salis, A.; Pinna, M.; Monduzzi, M.; Solinas, V.; J Biotechnol. 2005, 119, 291. [Crossref]
Triolein and FO	Aspergillus oryzae	fatty acid esters	97 (esters yield)	35	1:5	2	24	Monroe et al.⁵⁹59 Monroe, E.; Shinde, S.; Carlson, J. S.; Eckles, T. P.; Liu, F.; Varman, A. M.; George, A.; Davis, R. W.; Fuel 2020, 268, 117408. [Crossref]
Oleic acid and FO	Novozyme^® 435	isoamyl oleate	ca. 100 (ester yield)	60	1:2	0.5	12	Dormo et al.⁶⁰60 Dormo, N.; Bakó, K. B.; Bartha, L.; Ehrenstein, U.; Gubicza, L.; Biochem. Eng. J. 2004, 21, 229. [Crossref]
Oleic acid and FO	sulfuric acid	oleate ester	97 (oleic acid conversion)	90	1:2	1.25	1	Özgülsün et al.⁶¹61 Özgülsün, A.; Karaosmanǒglu, F.; Tüter, M.; J. Am. Oil Chem. Soc. 2000, 77, 105. [Crossref]
Waste baked duck oil (WBDO) and FO	Novozyme^® 435 and Lipozyme^® TL IM	fatty acid esters	90 (WBDO conversion)	45	1:4	5	15	Liu et al.⁶²62 Liu, Y.; Tan, H.; Zhang, X.; Yan, Y.; Hameed, B. H.; Chem. Eng. Sci. 2010, 157, 223. [Crossref]
Coconut oil and FO	Lipozyme^® TL IM	octanoic acid esters	38 (octanoic acid esters yield)	23	1:3	15	20	Sun et al.⁶³63 Sun, J.; Yu, B.; Curran, P.; Liu, S.-Q.; Food Chem. 2012, 134, 89. [Crossref]
Microalgal oil and FO	Burkholderia cepacia	fatty acid esters	89 (esters yield)	45	1:8	4	120	Silva et al.⁶⁴64 da Silva, A. P. T.; Bredda, E. H.; de Castro, H. F.; da Rós, P. C. M.; Fuel 2020, 273, 117786. [Crossref]
Macaw palm oil and FO	Burkholderia cepacian	fatty acid esters	ca. 100 (esters yield)	45	1:8	4	96
Oleic acid and FO	Rhizopus oryzae	isoamyl oleate	90 (ester yield)	45	1.5:1	10	24	Bôas et al.⁶⁵65 Bôas, R. N. B.; de Lima, R.; Mendes, A. A.; Freitas, L.; Bento, H. B. S.; de Carvalho, A. K. F.; de Castro, H. F.; Chem. Eng. Process. 2021, 168, 108568. [Crossref]
Stearic acid and FO	Rhizopus oryzae	isoamyl stearate	94 (isoamyl alcohol conversion)	45	1:1	12	24	Lima et al.⁶⁶66 de Lima, R.; Bento, H. B. S.; Reis, C. E. R.; Bôas, R. N. V.; de Freitas, L.; Carvalho, A. K. F.; de Castro, H. F.; Catal. Lett. 2022, 152, 547. [Crossref]
Stearic acid and FO	Candida antarctica	isoamyl stearate	91 (isoamyl alcohol conversion)	45	1:1	12	24

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	RU 2471769 (C2)	Method for processing fusel oil waste from alcohol production by esterification with acetic acid in presence of sulfuric acid catalyst	Panteleev et al.⁷⁷77 Panteleev, E. V.; Panteleev, P. E.; Panteleeva, G. V.; RU pat. 2471769, 2013.
Fatty acid	MD 4173 (B1)	Process for the production of biodiesel fuel	Covaliov et al.⁷⁸78 Covaliov, V.; Sliusarenco, V.; Nenno, V.; Covaliova, O.; MD pat. 4173, 2012.
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Fuel	FO concentration^a a In volume. SI: spark ignition; CI: compression ignition; nr: not reported. / %	Engine	Rotation / rpm	Engine loads / %	Reference
Gasoline	10 to 20	SI	4500	15 to 60	Awad et al.³⁴34 Awad, O. I.; Ali, O. M.; Hammid, A. T.; Mamat, R.; Renewable Energy 2018, 123, 79. [Crossref]
	0 to 50	SI	3500	100	Calam et al.⁸³83 Calam, A.; Içingür, Y.; Solmaz, H.; Yamk, H.; Int. J. Green Energy 2013, 12, 767. [Crossref]
	0 to 30	SI	1500 to 5000	25 to 100	Calam et al.⁸⁴84 Calam, A.; Solmaz, H.; Uyumaz, A.; Uyumaz, A.; Polat, S.; Yilmaz, E.; Içingur, Y.; J. Energy Inst. 2015, 88, 258. [Crossref]
	0 to 100	SI	2500	25 to 100	Solmaz⁸⁵85 Solmaz, H.; Fuel Process. Technol. 2015, 133, 20. [Crossref]
	0 to 30	SI	2600 to 3200	nr	Uslu and Celik⁸⁶86 Uslu, S.; Celik, M. B.; Fuel 2020, 262, 116496. [Crossref]
Diesel	0 to 10	nr	2200	19 to 96	Yilmaz²¹21 Yilmaz, E.; Fuel 2019, 255, 115741. [Crossref]
	0 to 20	SI	1200 to 2400	50 to 75	Awad et al.⁸²82 Awad, O. L.; Mamat, R.; Ali, O. M.; Yusri, I. M.; Abdullah, A. A.; Yusop, A. F.; Noor, M. M.; J. Energy Inst. 2017, 90, 382. [Crossref]
	0 to 20	CI	2600	2.5 to 12.5	Akcay and Ozer⁸⁷87 Akcay, M.; Ozer, S.; Energy Sources, Part A 2019, 1-16. [Crossref]
	10 to 20	CI	2000	15 to 60	Ağbulu et al.⁸⁸88 Ağbulu, Ü.; Saridemir, S.; Karagoz, M.; Fuel 2020, 267, 117042. [Crossref]

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FO concentration^a a In volume. nr: not reported. / %	Flow application / (L per hectare)	Commercial herbicide concentration / (g per hectare)	Weed	Reference
12.5 to 100	nr	nr	Brachiaria decumbens Sida rhombifolia	Azania et al.²²22 Azania, A. A. P. M.; Azania, C. A. M.; Marques, M. O.; Pavani, M. C. M. D.; Furtado, D. E.; Rodrigues, D.; Planta Daninha 2003, 21, 443. [Crossref]
0 to 100	50 to 500	nr	Ipomoea hederifolia Ipomoea quamoclit Euphorbia heterophylla Digitaria spp. Cenchrus Echinatus Panicum maximum	Azania et al.²³23 Azania, C. A. M.; Azania, A. A. P. M.; Pizzo, I. V.; Schiavetto, A. R.; Planta Daninha 2010, 28, 541. [Crossref]
0 to 100	25	diuron + hexazinone: 819 + 231 to 1170 + 330 metribuzin: 1344 to 1920 amicarbazone: 980 to 1400	Ipomoea quamoclit Amaranthus deflexus Panicum maximum Euphorbia heterophylla Brachiaria decumbens	Pizzo et al.²⁸28 Pizzo, I. V.; Azania, C. A. M.; Azania, A. A. P. M.; Schiavetto, A. R.; Planta Daninha 2010, 28, 347. [Crossref]
0 to 100	0 to 75	glyphosate: 0 to 6800	Commelina benghalensis Cyperus sp. Digitaria sp. Eleusine indica	Azania et al.¹⁰⁵105 Azania, A. A. P. M.; Marques, M. O.; Pavani, M. C. M. D.; Azania, C. A. M.; Planta Daninha 2003, 26, 231. [Crossref]

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[1] *e-mail: camiladasilva.eq@gmail.com

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Fusel Oil: Chemical Composition and an Overview of Its Potential Application