Síntese de novas amidas graxas a partir da aminólise de ésteres metílicos

Lopes, Carolina Rosa; D’Oca, Caroline Da Ros Montes; Duarte, Rodrigo da Costa; Kurz, Márcia Helena Scherer; Prímel, Ednei Gilberto; Clementin, Rosilene Maria; Villarreyes, Joaquín Ariel Morón; D’Oca, Marcelo Gonçalves Montes

doi:10.1590/s0100-40422010000600022

Cited by 13 publications

(8 citation statements)

References 38 publications

(53 reference statements)

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“…Taking into account the average molecular weight of the oils used, it was possible to calculate the mass to be used in reactions to satisfy the molar ratio of 3:1 (alcohol/oil), 1.5 ml of the enzyme solution (Novozym 435 and crude extract) with enzymatic activity of 88.0 U/ml [33].…”

Section: Biodiesel Productionmentioning

confidence: 99%

Isolation and Screening of Filamentous Fungi Producing Extracellular Lipase with Potential in Biodiesel Production

Pacheco¹,

Júnior²,

Morgado³

et al. 2015

AER

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Nineteen fungal strains were isolated from a chicken slaughterhouse effluent and within those, only one showed high values of lipolytic activity in submerged cultures. This fungus was identified as Trametes hirsuta. The crude extract was immobilized in chitosan/clay beads, with an immobilization yield of 80.9%. The analyses of the crude extract and the immobilized derivative at different temperatures, pH (s), solvents, metallic ions and storage showed that the immobilization process increased the enzyme life span. Ethyl esters were obtained in solvent free systems using chicken viscera oil and the enzyme crude extract. For effective comparison, a reaction using viscera oil and commercial lipase Novozym 435 was carried out. The result revealed 35% and 28% esters conversion in the reactions containing chicken viscera oil, using Novozym 435 and the crude extract respectively. The extract was also used in a reaction with soybean oil, traditionally used as starting substrate for biodiesel production.

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Section: Biodiesel Productionmentioning

confidence: 99%

Isolation and Screening of Filamentous Fungi Producing Extracellular Lipase with Potential in Biodiesel Production

Pacheco¹,

Júnior²,

Morgado³

et al. 2015

AER

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“…Different methods for preparation of ricinoleic acid amides can be found in literature, e.g., the aminolysis of fatty acid methyl esters with corresponding amines in the presence of sodium methoxide (Lopes et al, ) or in acetonitrile (D'Oca et al, ). However, in the present study, we have developed more environment‐friendly solvent‐free procedure that provides relatively good performance in the range of 43–88%.…”

Section: Resultsmentioning

confidence: 99%

“…1 H NMR (CDCl 3 , δ ppm): 5.53 (m, 1H; ─C H ═), 5.38 (m, 1H; ─C H ═), 3.63 (m, 7H; ─C H OH─, equatorial ─N(C H 2 ) 2 ─, ─(C H 2 ) 2 O), 3.44 (t, J = 4.8 Hz, 2H; axial ─N(C H 2 ) 2 ─), 2.29 (t, J = 7.6 Hz, 2H; ─C H 2 CO─), 2.19 (t, J = 6.8 Hz, 2H; ─CHC H 2 CH═), 1.60 (q, J = 6.9 Hz, 2H), 1.29 (m, 16H), 0.86 (t, J = 6.6 Hz, 3H; ─C H 3 ); lit. 1 H NMR (300 MHz, CDCl 3 ) δ 5.49 (m, 1H), 5.37 (m, 1H), 3.60 (m, 6H), 3.39 (m, 2H), 2.23 (t, J = 7.5 Hz, 2H), 2.13 (m, 2H), 1.96 (m, 2H), 1.55 (m, 2H), 1.21 (m, 20H), 0.81 (t, J = 7.2 Hz, 3H) (Lopes et al, ). 13 C NMR (CDCl 3 ): 171.80 (s, – C O─), 133.13 (d, ─ C H═), 125.25 (d, ─ C H═), 71.38 (d, ─ C HOH─), 66.87 (t, ─ C H 2 O─), 66.60 (t, ─ C H 2 O─), 45.97 (t, ─NC H 2 ─), 41.79 (t, ─NC H 2 ─), 36.78 (t, ─CH C H 2 CH═), 35.29 (t), 33.01 (t), 31.76 (t), 29.49 (t), 29.29 (t, 2xCH 2 ), 29.18 (t), 29.02 (t), 27.28 (t), 25.64 (t), 25.11 (t), 22.53 (t), 14.01 (q, ─ C H 3 ); lit.…”

Section: Methodsmentioning

confidence: 99%

“…13 C NMR (CDCl 3 ): 171.80 (s, – C O─), 133.13 (d, ─ C H═), 125.25 (d, ─ C H═), 71.38 (d, ─ C HOH─), 66.87 (t, ─ C H 2 O─), 66.60 (t, ─ C H 2 O─), 45.97 (t, ─NC H 2 ─), 41.79 (t, ─NC H 2 ─), 36.78 (t, ─CH C H 2 CH═), 35.29 (t), 33.01 (t), 31.76 (t), 29.49 (t), 29.29 (t, 2xCH 2 ), 29.18 (t), 29.02 (t), 27.28 (t), 25.64 (t), 25.11 (t), 22.53 (t), 14.01 (q, ─ C H 3 ); lit. 13 C NMR (75 MHz, CDCl 3 ) δ 172.17, 133.49, 125.51, 71.68, 67.19, 66.92, 46.29, 42.12, 37.07, 35.59, 33.35, 32.09, 29.82, 29.62 (2C), 29.50, 29.35, 27.61, 25.97, 25.45, 22.87, 14.35 (Lopes et al, ). ESI MS m / z : 368.4 (100%) [M + H] + , 390.4 (9.6%) [M + Na] + .…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (CDCl 3 , δ ppm): 5.44 (m, 1H; ─C H ═), 5.36 (m, 1H; ─C H ═), 3.52 (m, 1H; ─C H OH─ ) , 3.39 and 3.34 (t, J = 6.4 Hz, t, J = 6.3 Hz, 4H; ─N(C H 2 ) 2 ─), 2.15 (m, 4H; ─C H 2 CO─, ─CHC H 2 CH═), 1.57 (m, 2H), 1.22 (m, 16H), 0.81 (t, J = 7 Hz, 3H; ─C H 3 ); lit. 1 H NMR (300 MHz, CDCl 3 ) δ 5.51 (m, 1H), 5.42 (m, 1H), 3.68 (m, 1H), 3.43 (m, 4H), 2.27 (sl, 1H), 2.25 (m, 4H), 2.03 (m, 2H), 1.95 (m, 2H), 1.85 (m, 2H), 1.63 (m, 2H), 1.25 (m, 18H), 0.88 (t, J = 6.6 Hz, 3H) (Lopes et al, ). 13 C NMR (CDCl 3 ): 171.65 (s; ─ C O─), 132.79 (d; ─ C H═), 125.24 (d; ─ C H═), 71.20 (d; ─ C HOH─), 46.43 (t; ─N C H 2 ─), 45.39 (t; ─N C H 2 ─), 36.65 (t; ─CH C H 2 CH═), 35.20 (t), 34.60 (t), 31.67 (t), 29.39 (t), 29.23 (t), 29.20 (t), 29.11 (t), 28.93 (t), 27.18 (t), 25.94 (t), 25.54 (t), 24.70 (t), 24.22 (t), 22.44 (t), 13.91 (q; ─ C H 3 ); lit.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of (R)‐ and (S)‐Ricinoleic Acid Amides and Evaluation of Their Antimicrobial Activity

Matysiak

Zabielska

Kula

et al. 2018

J Americ Oil Chem Soc

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A series of fatty acid amides derived from (R)‐ and (S)‐ricinoleic acid and 4 cyclic and acyclic amines were synthesized in a proecological solvent‐free process with yields ranging from 43 to 88%. All S‐configured compounds and both enantiomers of amide with 2‐amino‐2‐methyl‐1‐propanol were obtained and studied in terms of biological activity for the first time. The evaluation of antimicrobial activity of (R)‐ and (S)‐ricinoleic acid derivatives against 13 different microorganisms representing Gram‐negative and Gram‐positive bacteria, yeast, and molds showed significant inhibitory activity against Gram‐positive bacteria, especially Micrococcus luteus and Bacillus subtilis, and against selected molds. Ethanolamine‐ and pyrrolidine‐derived amides showed the most promising antibacterial and antimold potential. Derivatives from ricinoleic acid and pyrrolidine were the most active against both selected molds, Aspergillus brasiliensis and Penicillium expansum. Moreover, the R‐configured analog was the most potent against B. subtilis. The amides of ricinoleic acid with ethanolamine exhibited significant potential to Staphylococcus aureus, which distinguished them from the rest of tested derivatives to which this bacterium was very resistant.

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Catalytic Aminolysis (Amide Formation) from Esters and Carboxylic Acids: Mechanism, Enhanced Ionic Liquid Effect, and its Origin

et al. 2011

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This paper describes the use of imidazolium‐based ionic liquids {1‐n‐butyl‐3‐methylimidazolium tetrafluoroborate [BMI‐BF4], 1‐n‐butyl‐3‐methylimidazolium hexafluorophosphate [BMI‐PF6], and 1‐n‐butyl‐3‐methylimidazolium bis(trifluoromethylsulfonyl)imide [BMI‐NTf2]} as efficient supports for Lewis and Brønsted acids ,which are promoters of the aminolysis of some esters, fatty acids, and fatty acid esters (among others) to form amide derivatives. Some esters and carboxylic acids were tested to demonstrate the generality of the methodology, and the corresponding amides were obtained in high yields. Recycling reactions (at least eight reuses) without a notable loss in activity could be performed by using CdO and SnCl2 as catalysts in BMI‐NTf2 as the ionic medium. Brønsted acids, such as H2SO4 and HCl, were also tested with impressive results; however, it was not possible to perform recycling reactions because of catalyst leaching. The same was true when using BF3⋅OEt2 as the catalyst. Mechanistic insights and the ionic‐liquid effect were investigated by using 13C{1H} NMR spectroscopy, which showed that there is a strong interaction of the imidazolium cation with the CO and CC bonds of methyl oleate, most likely through CH⋅⋅⋅π interactions, π‐stacking interactions, and ion‐pair formation in the presence of a metal catalyst. Electrospray ionization–quadrupole time‐of‐flight experiments allowed a better understanding of the reaction mechanism. The results could explain the enhanced ionic‐liquid effect on the stabilization of the formed intermediates, which facilitated the amide bond formation.

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Síntese de novas amidas graxas a partir da aminólise de ésteres metílicos

Cited by 13 publications

References 38 publications

Isolation and Screening of Filamentous Fungi Producing Extracellular Lipase with Potential in Biodiesel Production

Isolation and Screening of Filamentous Fungi Producing Extracellular Lipase with Potential in Biodiesel Production

Synthesis of (R)‐ and (S)‐Ricinoleic Acid Amides and Evaluation of Their Antimicrobial Activity

Catalytic Aminolysis (Amide Formation) from Esters and Carboxylic Acids: Mechanism, Enhanced Ionic Liquid Effect, and its Origin

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