<i>In situ</i> Transesterification of Crambe Seeds with Dimethyl Carbonate Using an Enzymatic Catalyst

Silva, Camila da; Massa, Thainara B.; Mello, Bruna Tais F. de; Feiten, Mirian Cristina; Stevanato, Natália; Postaue, Najla

doi:10.21577/0103-5053.20230194

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Article • J. Braz. Chem. Soc. 35 (6) • 2024 • https://doi.org/10.21577/0103-5053.20230194 copy

In situ Transesterification of Crambe Seeds with Dimethyl Carbonate Using an Enzymatic Catalyst

Authorship SCIMAGO INSTITUTIONS RANKINGS

In situ transesterification of crambe seeds oil was investigated to produce fatty acid methyl esters using dimethyl carbonate as acyl acceptor and lipase Novozyme 435® as the catalyst. First, the effects of solvent-to-seeds ratio, seed pretreatment, and extraction time were evaluated on the seed oil removal, comparing the results with conventional Soxhlet extraction. Then, the effects of enzyme loading (5 to 30 wt.% based on the oil mass) and reaction time (60 to 540 min) were evaluated on the simultaneous extraction and reaction. The highest oil extraction yield (ca. 26 wt.%) was achieved at the solvent-to-seeds ratio of 6 mL g^-1 and 360 min. The oil obtained from seeds that received thermal pretreatment showed a higher concentration of minor compounds. The highest ester content (76.71 wt.%) was obtained with an enzyme loading of 20 wt.%, solvent-to-seeds ratio of 6 mL g^-1, for 480 min. The reaction samples showed a predominance of erucate and oleate esters, with identification of the co-products formation (glycerol carbonate and glycerol dicarbonate), and ca. 5 wt.% of acylglycerols.

Keywords:
Crambe abyssinica Hochst; oil extraction; methyl esters; Novozyme 435®; glycerol carbonate

Oil	FFA / wt.%	Phytosterol / (mg per 100 g of oil)			γ-Tocopherol / (mg per 100 g of oil)
Oil	FFA / wt.%	Stigmasterol	β-Sitosterol	Campesterol	γ-Tocopherol / (mg per 100 g of oil)
UTS	0.79 ± 0.04^a	58.30 ± 0.50^a	111.23 ± 1.53^a	56.81 ± 0.26^a	115.14 ± 1.88^a
TT	0.65 ± 0.02^b	69.45 ± 2.14^b	141.24 ± 3.64^b	61.41 ± 0.09^b	125.75 ± 1.69^b

Property	Reaction time / min
Property	360	420	480	540
FAMEs / %	myristate	0.10 ± 0.01^a	0.07 ± < 0.01^ab	0.06 ± 0.01^b	0.07 ± 0.01^ab
	palmitate	2.15 ± 0.06^b	2.08 ± 0.17^b	2.28 ± < 0.01^b	2.68 ± 0.01^a
	palmitoleate	0.13 ± 0.02^a	0.10 ± < 0.01^a	0.14 ± 0.01^a	0.13 ± < 0.01^a
	stearate	1.14 ± 0.04^a	1.24 ± 0.12^a	1.17 ± 0.02^a	1.31 ± 0.02^a
	oleate	18.98 ± 0.02^a	18.45 ± 0.80^a	19.16 ± 0.03^a	19.32 ± 0.05^a
	linoleate	7.11 ± 0.04^b	6.98 ± 0.46^b	7.28 ± <0.01^ab	8.07 ± 0.04^a
	linolenate	3.90 ± 0.09^a	3.69 ± 0.41^a	3.86 ± 0.01^a	3.74 ± < 0.01^a
	arachisate	1.16 ± 0.05^a	1.23 ± 0.04^a	1.19 ± 0.01^a	1.22 ± 0.02^a
	gadoleate	5.74 ± 0.02^a	5.73 ± 0.40^a	5.88 ± 0.02^a	5.80 ± 0.13^a
	behenate	2.07 ± 0.08^a	2.23 ± 0.15^a	2.07 ± 0.01^a	2.37 ± 0.02^a
	erucate	54.51±0.48^a	55.18 ± 1.97^a	53.93 ± 0.06^a	52.34 ± 0.13^a
	lignocerate	0.71 ± 0.01^a	0.81 ± 0.10^a	0.80 ± 0.02^a	0.78 ± 0.10^a
	nervonate	1.48 ± 0.06^a	1.47 ± 0.04^a	1.41 ± < 0.01^a	1.42 ± 0.02^a
	not identified	0.83 ± 0.03	0.83 ± < 0.01	0.79 ± 0.03	0.75 ± 0.06
Glycerol carbonate / ppm		125.77 ± 0.7^b	105.49 ± 0.82^c	108.90 ± 1.59^c	227.16 ± 2.28^a
Glycerol dicarbonate / ppm		550.88± 1.63^a	291.82 ± 9.96^b	184.85 ± 3.34^c	130.79 ± 1.25^d
Triglycerides / wt.%		5.97 ± 0.28^a	3.37 ± 0.30^b	2.83 ± 0.32^b	1.91 ± 0.33^c
Diglycerides / wt.%		4.52 ± 0.45^a	2.12 ± 0.25^b	2.16 ± 0.18^b	1.17 ± 0.16^c
Monoglycerides / wt.%		0.19 ± 0.01^b	0.36 ± 0.02^a	0.36 ± 0.03^a	0.22 ± 0.01^b

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[1] * e-mail: csilva@uem.br