Unsaturated Renewable Oil Transformation into Novel Biofuel Compositions via an Olefin Metathesis-Transesterification-Hydrogenation Sequence

Lima, Priscilla S.; Ferreira, Leonildo A.; Freitas, Luiza H.; Rheinheimer, Martin W.; Sokolovicz, Yuri C. A.; Schrekker, Henri S.

doi:10.5935/0103-5053.20140208

Priscilla S. Lima

Laboratory of Technological Processes and Catalysis, Institute of Chemistry, Federal University of Rio Grande do Sul, Av. Bento Gonçalves, 9500, 91501-970 Porto Alegre-RS, Brazil

Leonildo A. Ferreira

Laboratory of Technological Processes and Catalysis, Institute of Chemistry, Federal University of Rio Grande do Sul, Av. Bento Gonçalves, 9500, 91501-970 Porto Alegre-RS, Brazil

Luiza H. Freitas

Laboratory of Technological Processes and Catalysis, Institute of Chemistry, Federal University of Rio Grande do Sul, Av. Bento Gonçalves, 9500, 91501-970 Porto Alegre-RS, Brazil

Martin W. Rheinheimer

Laboratory of Technological Processes and Catalysis, Institute of Chemistry, Federal University of Rio Grande do Sul, Av. Bento Gonçalves, 9500, 91501-970 Porto Alegre-RS, Brazil

Yuri C. A. Sokolovicz

Laboratory of Technological Processes and Catalysis, Institute of Chemistry, Federal University of Rio Grande do Sul, Av. Bento Gonçalves, 9500, 91501-970 Porto Alegre-RS, Brazil

Henri S. Schrekker ^** e-mail: henri.schrekker@ufrgs.br

Laboratory of Technological Processes and Catalysis, Institute of Chemistry, Federal University of Rio Grande do Sul, Av. Bento Gonçalves, 9500, 91501-970 Porto Alegre-RS, Brazil

* e-mail: henri.schrekker@ufrgs.br

Oil			Unsaturated fatty acid / %
Oil	Palmitoleic (16:1)	Oleic (18:1)	Linoleic (18:2)	Linolenic (18:3)	Total
Olive^a a Edible oil;	0.92	75.5	7.02	0.66	84.10
Canola^a a Edible oil;	0.21	62.41	20.12	8.37	91.11
Peanut^a a Edible oil;	0.06	48.71	31.06	0.23	80.06
Soybean^a a Edible oil;	0.08	21.35	56.02	7.15	84.60
Tobbaco seed^b b non-edible oil.	0.2	14.54	69.49	0.69	84.92
Milkweed seed^b b non-edible oil.	6.8	34.8	48.7	1.2	91.5
Caper spurge^b b non-edible oil.	0.5	81.46	3.71	2.78	88.45
Jatropha^b b non-edible oil.	0.7	39.1	41.6	0.2	81.6
Rice bran^b b non-edible oil.	0	47.5	35.4	1.1	84.0
Chinese tallow seed^b b non-edible oil.	3.7	16.7	31.5	41.5	93.4
Croton^b b non-edible oil.	0.11	9.95	74.31	3.62	87.99

entry	Oil / g	Toluene:oil ratio^b b molar ratio;	Catalyst	Oil:catalyst ratio^b b molar ratio;	Pressure / bar^c c ethylene pressure;	time / min	Conversion / %^d d determined by 1H NMR (see Supplementary Information);
1	10	1:4	G1	2000:1	45	120	14
2	10	15:1	G1	2000:1	45	120	23
3	10	13:1	G1	100:1	45	120	52
4	10^e e olive oil treated with activated carbon;	1:4	G1	2000:1	45	120	37
5	2^e e olive oil treated with activated carbon;	63:1	G1	333:1	1	30	50
6	2^e e olive oil treated with activated carbon;	63:1	G2	333:1	1	30	48
7	2^e e olive oil treated with activated carbon;	63:1	HG2	333:1	1	30	19
8	2^e e olive oil treated with activated carbon;	63:1	G1	333:1	1	60	49
9	2^e e olive oil treated with activated carbon;	63:1	G1	333:1	2	60	70
10	2^e e olive oil treated with activated carbon;	63:1	G1	333:1	3	60	64
11	2^e e olive oil treated with activated carbon;	63:1	G1	333:1	4	60	63
12	10^f f transesterified olive oil;	1:12	G1	2000:1	45	120	8
13	5^g g commercial methyl oleate.	1:6	G1	2000:1	45	240	48

Component C₁₀-C₁₈	Potential biofuel^a a Compositions determined by GC-MS; ,^b b numbers between parentheses show the ethenolysis conversion (%) determined by 1H NMR;
Component C₁₀-C₁₈	1 (10)^c c not reported in Table 1.	2 (42)^c c not reported in Table 1.	3 (52)
Decane	7.9	15.8	19.1
Methyl decanoate	10.4	25.9	27.0
Methyl hexadecanoate	11.9	11.0	13.2
Methyl octadecanoate	68.8	45.0	36.5
Biogasoline/biokerosene (C₁₀) in biofuel / %	18.3	41.7	46.0
Biodiesel (C₁₆-C₁₈) in biofuel / %	80.7	56.0	49.6

[1] * e-mail: henri.schrekker@ufrgs.br

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Unsaturated Renewable Oil Transformation into Novel Biofuel Compositions via an Olefin Metathesis-Transesterification-Hydrogenation Sequence