Reaction of Fatty Acid Methyl Ester with Monoethanolamine and Diethanolamine
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Markéta Berčíková
Markéta Berčíková is an Assistant Professor at Department of Dairy, Fat and Cosmetics, Faculty of Food and Biochemical Technology, University of Chemistry and Technology (UCT), Prague, Czech Republic. She received her MSc at UCT Prague (2002) and PhD at UCT Prague (2008). Her research interest encompasses surfactant chemistry and physico-chemical properties of detergents.
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Jiří Lád
Jiří Lád received his MSc at University of Chemistry and Technology Prague (UCT) (2001) and PhD at UCT Prague (2006). He is working in chemical industry.
Iveta Hrádková is an Assistant Professor at Department of Dairy, Fat and Cosmetics, Faculty of Food and Biochemical Technology, University of Chemistry and Technology (UCT), Prague, Czech Republic. She received her MSc at UCT Prague (2002) and PhD at UCT Prague (2006). Her research interest encompasses cosmetic and lipid chemistry.
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Monika Kumherová
Monika Kumherová is a PhD student at Department of Dairy, Fat and Cosmetics, Faculty of Food and Biochemical Technology, University of Chemistry and Technology (UCT), Prague, Czech Republic. She received her MSc at UCT Prague (2016). Her research interests include cosmetic chemistry and microbiology.
Jan Smidrkal is a Professor at Department of Dairy, Fat and Cosmetics, Faculty of Food and Biochemical Technology, University of Chemistry and Technology (UCT), Prague. He received his MSc at UCT Prague (1970) and he obtained his PhD (1976) in organic chemistry at the Charles University in Prague. He has more than 40 years researching experience in surfactant and detergent chemistry and more than 25 years teaching experience in chemistry.
Abstract
The course of the reaction between lauric acid and monoethanolamine as well as the reaction of methyl laurate with monoethanolamine and diethanolamine were investigated. Thin layer chromatography with flame ionisation detector was used for reaction mixture analysis. The fatty acid methyl ester is more suitable for production of monoethanolamide and diethanolamide. Sodium methoxide or potassium hydroxide (0.02 mol % ester) was used as suitable alkaline catalysts of reaction. The optimal temperature of methyl laurate or coconut oil with diethanolamine reaction is 80°C. Higher temperatures (over 100°C) lead to a higher concentration of amide ester in the product.
Zusammenfassung
Untersucht wurden der Verlauf der Reaktion zwischen Laurinsäure und Monoethanolamin sowie die Reaktion von Methyllaurat mit Monoethanolamin und Diethanolamin. Zur Analyse des Reaktionsgemisches wurde die Dünnschichtchromatographie mit Flammen-Ionisations-Detektor eingesetzt. Zur Herstellung von Monoethanolamid und Diethanolamid ist der Fettsäuremethylester besser geeignet. Als geeignete alkalische Reaktionskatalysatoren wurden Natriummethoxid oder Kaliumhydroxid (0,02 Mol-% Ester) verwendet. Die optimale Temperatur für die Reaktion von Methyllaurat oder Kokosnussöl mit Diethanolamin liegt bei 80°C. Höhere Temperaturen (über 100°C) führen zu einer höheren Konzentration von Amidester im Produkt.
About the authors
Markéta Berčíková is an Assistant Professor at Department of Dairy, Fat and Cosmetics, Faculty of Food and Biochemical Technology, University of Chemistry and Technology (UCT), Prague, Czech Republic. She received her MSc at UCT Prague (2002) and PhD at UCT Prague (2008). Her research interest encompasses surfactant chemistry and physico-chemical properties of detergents.
Jiří Lád received his MSc at University of Chemistry and Technology Prague (UCT) (2001) and PhD at UCT Prague (2006). He is working in chemical industry.
Iveta Hrádková is an Assistant Professor at Department of Dairy, Fat and Cosmetics, Faculty of Food and Biochemical Technology, University of Chemistry and Technology (UCT), Prague, Czech Republic. She received her MSc at UCT Prague (2002) and PhD at UCT Prague (2006). Her research interest encompasses cosmetic and lipid chemistry.
Monika Kumherová is a PhD student at Department of Dairy, Fat and Cosmetics, Faculty of Food and Biochemical Technology, University of Chemistry and Technology (UCT), Prague, Czech Republic. She received her MSc at UCT Prague (2016). Her research interests include cosmetic chemistry and microbiology.
Jan Smidrkal is a Professor at Department of Dairy, Fat and Cosmetics, Faculty of Food and Biochemical Technology, University of Chemistry and Technology (UCT), Prague. He received his MSc at UCT Prague (1970) and he obtained his PhD (1976) in organic chemistry at the Charles University in Prague. He has more than 40 years researching experience in surfactant and detergent chemistry and more than 25 years teaching experience in chemistry.
Acknowledgements
This work was supported by specific university research (MSMT No. 20-SVV/2020).
Abbreviations
- DEA,
diethanolamine;
- DIPA,
diisopropylamine;
- HPLC,
High Pressure Liquid Chromatography;
- LaAc,
lauric acid;
- MEA,
monoethanolamine;
- MeLa,
methyl ester of lauric acid;
- MIPA,
monoisopropanolamine;
- TLC/FID,
Thin Layer Chromatography/Flame Ionisation Detector.
References
1 Kritchevsky, W.: Hydrotropic Fatty Material and Method of Making Same, (1937) U. S. Patent 2,089,212.Search in Google Scholar
2 Meade, E. M.: Process for the Amidation of Esters, (1949) U. S. Patent 2,464,094.Search in Google Scholar
3 Monick, J. A.: Continuous High Temperature Preparation of Alkylolamides, J Am. Oil. Chem Soc. 39 (1962) 213–215. DOI:10.1007/BF0263582210.1007/BF02635822Search in Google Scholar
4 Betts, R. L., Hammet, L.: A Kinetic Study of the Ammonolysis of Phenylacetic Esters in Methanol Solution, J. Am. Chem. Soc. 59 (1937) 1568–1572. DOI:10.1021/ja01287a04310.1021/ja01287a043Search in Google Scholar
5 Wetzel, F. H., Miller, J .G. and Day, A. R.: Effect of Structure on Reactivity. VII. The Energies of Activation and the Entropies of Activation for the Ammonolysis of Esters, J. Am. Chem. Soc. 75 (1953) 1150–1153. DOI:10.1021/ja01101a04210.1021/ja01101a042Search in Google Scholar
6 Trowbridge, J. R., Falk, R. A. and Krems, I. J.: Fatty Acid Derivatives of Diethanolamine, J. Org. Chem. 20 (1955) 990–995. DOI:10.1021/jo01365a00510.1021/jo01365a005Search in Google Scholar
7 Morales-Sanfrutos, J., Megia-Fernandez, A., Hernandez-Mateo, F., Giron-Gonzalez M. D., Salto-Gonzalez, R. and Santoyo-Gonzalez, F.: Alkyl sulfonyl derivatized PAMAM-G2 dendrimers as nonviral gene delivery vectors with improved transfection efficiencies, Org. Biomol. Chem. 9 (2011) 851–864. PMid:21120228; DOI:10.1039/c0ob00355 g10.1039/c0ob00355gSearch in Google Scholar PubMed
8 Han, D., Wang, B., Jin, H., Wang, H. and Chen, M.: Design, synthesis and CoMFA studies of OEA derivatives as FAAH inhibitors, Med. Chem. Res 26 (2017) 2951–2966; DOI:10.1007/s00044-017-1995-610.1007/s00044-017-1995-6Search in Google Scholar
9 Sanders, H. L.: Fatty Acid Alkylolamides, J Am. Oil. Chem Soc. 35 (1958) 548–551. DOI:10.1007/BF0263795910.1007/BF02637959Search in Google Scholar
10 Desnuelle, P., Naudet, M. and Sambuc, E.: Sur la transposition des a-oxyéthylamides gras en les a-amino-esters correspondats, Bull. Soc. Chim. Fr. 152 (1949), 650–654.Search in Google Scholar
11 van Tamelen, E. E.: The Mechanism of Nitrogen-Oxygen Acyl Migrations, J. Am. Chem. Soc. 73 (1951) 5773–5774. DOI:10.1021/ja01156a08310.1021/ja01156a083Search in Google Scholar
12 Lee, C. S., Ooi, T. L., Chuah, C. H. and Ahmad, S.: Synthesis of Palm Oil-Based Diethanolamides, J Am. Oil. Chem Soc. 84 (2007), 945–952. DOI:10.1007/s11746-007-1123-810.1007/s11746-007-1123-8Search in Google Scholar
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Articles in the same Issue
- Contents
- Biosufractants
- Fermentative Production of Mannosylerythritol Lipids using Sweetwater as Waste Substrate by Pseudozyma antarctica (MTCC 2706)
- Environmental chemistry
- Heavy Oil Storage Tanks Clean-up Using Biosurfactants and Investigation of the Synergistic Effect with Silica Nanoparticles
- Physical chemistry
- Phase Studies and Efficient Recovery of Inorganic Metal Salts from the Microemulsion System Using a Sugar-Based Non-Ionic Surfactant
- Stability of the PEG Fatty Acid Glycerides Based O/W Emulsions
- The Effect of Halide Counter Ions and Methanol on the Foaming Behavior of Cationic Surfactants and a Mechanism Study
- Synthesis
- Reaction of Fatty Acid Methyl Ester with Monoethanolamine and Diethanolamine
- Micellar catalysis
- Aggregation of Surfactants: Catalytic Reinforcement in Oxidation of Unsaturated E-Crotonaldehyde
- Application
- Enhancing the Stability of Asphalt Emulsion Using Environmentally Friendly Cationically Modified Hydroxyethyl Cellulose (CMHEC) at Different Concentrations and pH Values
- Preparation of Ammonium Oleic Acid Salts and Their Evaluation as Shale Swelling Inhibitors in Water-Based Drilling Fluid
Articles in the same Issue
- Contents
- Biosufractants
- Fermentative Production of Mannosylerythritol Lipids using Sweetwater as Waste Substrate by Pseudozyma antarctica (MTCC 2706)
- Environmental chemistry
- Heavy Oil Storage Tanks Clean-up Using Biosurfactants and Investigation of the Synergistic Effect with Silica Nanoparticles
- Physical chemistry
- Phase Studies and Efficient Recovery of Inorganic Metal Salts from the Microemulsion System Using a Sugar-Based Non-Ionic Surfactant
- Stability of the PEG Fatty Acid Glycerides Based O/W Emulsions
- The Effect of Halide Counter Ions and Methanol on the Foaming Behavior of Cationic Surfactants and a Mechanism Study
- Synthesis
- Reaction of Fatty Acid Methyl Ester with Monoethanolamine and Diethanolamine
- Micellar catalysis
- Aggregation of Surfactants: Catalytic Reinforcement in Oxidation of Unsaturated E-Crotonaldehyde
- Application
- Enhancing the Stability of Asphalt Emulsion Using Environmentally Friendly Cationically Modified Hydroxyethyl Cellulose (CMHEC) at Different Concentrations and pH Values
- Preparation of Ammonium Oleic Acid Salts and Their Evaluation as Shale Swelling Inhibitors in Water-Based Drilling Fluid
