Amidation of fatty acid methyl ester using metal oxides and hydroxides as catalysts
Comparison of catalytic activity of metal oxides and hydroxides in amidation reaction between fatty acid methyl esters and 3-(dimethylamino)-1-propylamine was made for the first time. Influences of basicity, structure and solubility of catalysts on its catalytic activity were shown. It was detected, that catalysis of amidation of fatty acid methyl esters is homogenous. High activity of mixed oxides (Fe3O4 and Co3O4) was noted.
KeywordsAmidation 3-(Dimethylamino)-1-propylamine Fatty acid methyl esters Hydroxides Oxides
The investigation of metal hydroxides activities was financially supported by The Ministry of Education and Science of the Russian Federation (State assignment No 10.2326.2017/PP). The investigation of metal oxides activities was financially supported within the framework of the Program of development of Flagship University of Russia for Nizhny Novgorod State Technical University n.a. R.E. Alekseev.
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Conflict of interest
On behalf of all authors, the corresponding author states that there is no conflict of interest.
- De Oliveira VM, Silva de Jesus R, Gomes AF, Gozzo FC, Umpierre AP, Suarez PAZ, Rubim JC, Neto BAD (2011) Catalytic aminolysis (amide formation) from esters and carboxylic acids: mechanism, enhanced ionic liquid effect, and its origin. ChemCatChem. 3:1911–1920. https://doi.org/10.1002/cctc.201100221 CrossRefGoogle Scholar
- Gernigon N, Al-Zoubi RM, Hall DG (2012) Direct amidation of carboxylic acids catalyzed by ortho-iodo arylboronic acids: catalyst optimization, scope, and preliminary mechanistic study supporting a peculiar halogen acceleration effect. J Org Chem 77:8386–8400. https://doi.org/10.1021/jo3013258 CrossRefGoogle Scholar
- Gervajio CG (2005) Fatty acids and derivatives from coconut oil. In: Shahidi F (ed) Bailey’s industrial oil and fat products. Wiley, New York, pp 1–56Google Scholar
- Lange KR (1999) Surfactants. A practical handbook. Hanser Publishers, MunichGoogle Scholar
- Li W, Ivanov S, Mozaffari S, Shanaiah N, Karim AM (2018) Palladium acetate trimer: understanding its ligand-induced dissociation thermochemistry using isothermal titration calorimetry, X-ray absorption fine structure, and 31P nuclear magnetic resonance. Organometallics. https://doi.org/10.1021/acs.organomet.8b00787 Google Scholar
- Litjens MJJ, Sha M, Straathof AJJ, Jongejan JA, Heijnen JJ (1999) Competitive lipase-catalyzed ester hydrolysis and ammoniolysis in organic solvents; equilibrium model of a solid–liquid–vapor system. Biotechnol Bioeng 65:347–356. https://doi.org/10.1002/(SICI)1097-0290(19991105)65:3%3c347:AID-BIT13%3e3.0.CO;2-9 CrossRefGoogle Scholar
- Mozaffari S, Li W, Thompson C, Ivanov S, Seifert S, Lee B, Kovarik L, Karim AM (2017) Colloidal nanoparticle size control: experimental and kinetic modeling investigation of the ligand–metal binding role in controlling the nucleation and growth kinetics. Nanoscale 9:13772–13785CrossRefGoogle Scholar
- Raymond BE, Prislinger A (1989) Soap cosmetics chemical specialties. MacNair-Dorland Co., New York, pp 46–48Google Scholar
- Scheibel JJ, Shumate R. E (1997) US Patent 5681971AGoogle Scholar
- Stevens R (2015) US Patent 20150267024A1Google Scholar
- Vlasova LI, Latypova DR, Akhmet’yanova LA, Gibadullina NN, Ratner AA, Telin AG, Dokichev VA (2017) Preparation and hydrophobizing properties of carboxylic acid N-[3-(dimethylamino)propyl]amide hydrochlorides. Russ J Appl Chem 90(7):1102–1106. https://doi.org/10.1134/S1070427217070126 CrossRefGoogle Scholar
- Xie X, Li Y, Liu Z, Haruta M, Shen W (2009) Low-temperature oxidation of CO catalysed by Co(3)O(4) nanorods. Nature. 458:746. https://doi.org/10.1038/nature07877. http://www.periodensystem-online.de/index.php?show=list&id=acid&prop=pKb-Werte&sel=oz&el=92 CrossRefGoogle Scholar