Selective Synthesis of Fatty Alcohols over Mild Reaction Conditions via Non-Catalytic Liquid-Phase Fatty Acid Methyl Esters’ Reduction
The upgrading of fatty alcohols synthesis from natural fatty acid methyl esters’ reduction using alumina-supported NaBH<sub>4</sub> without H<sub>2</sub> supply was investigated. It was possible to synthesize fatty alcohols efficiently with high yields. By using pure NaBH<...
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2023-11-01
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| author | Alejandro Vallejo Orrego Cristián A. Ferretti Verónica K. Díez |
| author_facet | Alejandro Vallejo Orrego Cristián A. Ferretti Verónica K. Díez |
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| description | The upgrading of fatty alcohols synthesis from natural fatty acid methyl esters’ reduction using alumina-supported NaBH<sub>4</sub> without H<sub>2</sub> supply was investigated. It was possible to synthesize fatty alcohols efficiently with high yields. By using pure NaBH<sub>4</sub> or alumina-supported NaBH<sub>4</sub> and methanol as co-reactants, 100% selectivity towards fatty alcohols was achieved. The purpose of supporting the metal hydride is to increase its stability and ensure the recovery of the product at the end of the reaction. A high final fatty alcohol yield was obtained when alumina-supported NaBH<sub>4</sub> was used. The use of more than stoichiometric amounts of methanol and NaBH<sub>4</sub> is important to produce alkoxyborohydride anions that act as better reducing species than NaBH<sub>4</sub>. The reaction conditions effect was investigated and the role of short carbon chain alcohol structure was explained. The effect of fatty acid methyl ester structure was also examined. Saturated fatty acid methyl esters (methyl laurate, methyl myristate) with short carbon chains can be easily reduced using NaBH<sub>4</sub>/Al<sub>2</sub>O<sub>3</sub> and methanol, thus obtaining high conversion and selectable fuel alcohol. Unsaturated fatty acid methyl ester (methyl oleate) with longer carbon shows steric hindrance, which is not suitable for the interaction of esters and reduces the surface area, meaning that the conversion of fatty acid methyl ester is lower. |
| format | Article |
| id | doaj-art-560e623e5b684b6599db7f3c421a5de4 |
| institution | DOAJ |
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| language | English |
| publishDate | 2023-11-01 |
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| spelling | doaj-art-560e623e5b684b6599db7f3c421a5de42025-08-20T02:50:52ZengMDPI AGChemistry Proceedings2673-45832023-11-011418710.3390/ecsoc-27-16384Selective Synthesis of Fatty Alcohols over Mild Reaction Conditions via Non-Catalytic Liquid-Phase Fatty Acid Methyl Esters’ ReductionAlejandro Vallejo Orrego0Cristián A. Ferretti1Verónica K. Díez2Catalysis Science and Engineering Research Group (GICIC), Catalysis and Petrochemistry Research Institute (INCAPE) (UNL-CONICET), CCT CONICET, Santa Fe 3000, ArgentinaGroup of Organic Synthesis and Materials (GSOM), Laboratorio Fester—Organic Chemistry (FIQ), Institute of Applied Chemistry of the Litoral (IQAL) (UNL-CONICET), Universidad Nacional del Litoral, Santa Fe 3000, ArgentinaCatalysis Science and Engineering Research Group (GICIC), Catalysis and Petrochemistry Research Institute (INCAPE) (UNL-CONICET), CCT CONICET, Santa Fe 3000, ArgentinaThe upgrading of fatty alcohols synthesis from natural fatty acid methyl esters’ reduction using alumina-supported NaBH<sub>4</sub> without H<sub>2</sub> supply was investigated. It was possible to synthesize fatty alcohols efficiently with high yields. By using pure NaBH<sub>4</sub> or alumina-supported NaBH<sub>4</sub> and methanol as co-reactants, 100% selectivity towards fatty alcohols was achieved. The purpose of supporting the metal hydride is to increase its stability and ensure the recovery of the product at the end of the reaction. A high final fatty alcohol yield was obtained when alumina-supported NaBH<sub>4</sub> was used. The use of more than stoichiometric amounts of methanol and NaBH<sub>4</sub> is important to produce alkoxyborohydride anions that act as better reducing species than NaBH<sub>4</sub>. The reaction conditions effect was investigated and the role of short carbon chain alcohol structure was explained. The effect of fatty acid methyl ester structure was also examined. Saturated fatty acid methyl esters (methyl laurate, methyl myristate) with short carbon chains can be easily reduced using NaBH<sub>4</sub>/Al<sub>2</sub>O<sub>3</sub> and methanol, thus obtaining high conversion and selectable fuel alcohol. Unsaturated fatty acid methyl ester (methyl oleate) with longer carbon shows steric hindrance, which is not suitable for the interaction of esters and reduces the surface area, meaning that the conversion of fatty acid methyl ester is lower.https://www.mdpi.com/2673-4583/14/1/87fatty alcoholsreduction reactionfatty acid methyl esters |
| spellingShingle | Alejandro Vallejo Orrego Cristián A. Ferretti Verónica K. Díez Selective Synthesis of Fatty Alcohols over Mild Reaction Conditions via Non-Catalytic Liquid-Phase Fatty Acid Methyl Esters’ Reduction Chemistry Proceedings fatty alcohols reduction reaction fatty acid methyl esters |
| title | Selective Synthesis of Fatty Alcohols over Mild Reaction Conditions via Non-Catalytic Liquid-Phase Fatty Acid Methyl Esters’ Reduction |
| title_full | Selective Synthesis of Fatty Alcohols over Mild Reaction Conditions via Non-Catalytic Liquid-Phase Fatty Acid Methyl Esters’ Reduction |
| title_fullStr | Selective Synthesis of Fatty Alcohols over Mild Reaction Conditions via Non-Catalytic Liquid-Phase Fatty Acid Methyl Esters’ Reduction |
| title_full_unstemmed | Selective Synthesis of Fatty Alcohols over Mild Reaction Conditions via Non-Catalytic Liquid-Phase Fatty Acid Methyl Esters’ Reduction |
| title_short | Selective Synthesis of Fatty Alcohols over Mild Reaction Conditions via Non-Catalytic Liquid-Phase Fatty Acid Methyl Esters’ Reduction |
| title_sort | selective synthesis of fatty alcohols over mild reaction conditions via non catalytic liquid phase fatty acid methyl esters reduction |
| topic | fatty alcohols reduction reaction fatty acid methyl esters |
| url | https://www.mdpi.com/2673-4583/14/1/87 |
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