Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis

Jamil, Md. A. R.; Siddiki, S. M. A. Hakim; Touchy, Abeda S.; Rashed, Md. Nurnobi; Poly, Sharmin Sultana; Yuan, Jing; Ting, Kah Wei; Toyao, Takashi; Maeno, Zen; Shimizu, Ken‐ichi

doi:10.1002/cssc.201900365

Cited by 31 publications

(36 citation statements)

References 74 publications

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“…5b, L2) as privileged ligands in combination with a ruthenium or cobalt precursor. Notable developments from 2015 to 2019 reached in the field of heterogeneous catalysis were described by the groups of Kim 146 148 respectively, were showcased as active systems.…”

Section: Related Catalytic Hydrogenative Transformationsmentioning

confidence: 99%

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

et al. 2020

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Catalytic hydrogenation of amides is of great interest for chemists working in organic synthesis, as the resulting amines are widely featured in natural products, drugs, agrochemicals, dyes, etc. Compared to traditional reduction of amides using (over)stoichiometric reductants, the direct hydrogenation of amides using molecular hydrogen represents a greener approach. Furthermore, amide hydrogenation is a highly versatile transformation, since not only higher amines (obtained by CO cleavage), but also lower amines and alcohols, or amino alcohols (obtained by C-N cleavage) can be selectively accessed by fine tuning of reaction conditions. This review describes the most recent advances in the area of amide hydrogenation using H 2 exclusively and molecularly defined homogeneous as well as nanostructured heterogeneous catalysts, with a special focus on catalyst development and synthetic applications. T he development of green and sustainable methods is a central focus of modern organic synthesis and its applications in various areas of the chemical industry. In this respect, many reduction reactions, traditionally employing stoichiometric amounts of metal hydrides with inherent low atom efficiency 1 , can be favorably replaced by catalytic hydrogenations. In fact, the combination of molecular hydrogen and catalysts does not only allow avoiding formation of waste products 2 , it also opens the door to clean transformations based on renewable energies as the conversion of solar or wind energy to "green" hydrogen is likely to be implemented in the coming years. Among the many reduction reactions known, amide hydrogenation can be encountered as one of the most desired considering the importance of the derived amines in several branches of chemical industry. In fact, since the start of the Green Chemistry Institute Pharmaceutical Roundtable in the United States in 2005, several projects aimed to the achievement of a practical amide hydrogenation methodology have been supported 3,4. The long-term interest of the pharmaceutical industry in this specific transformation is explained by the fact that it ideally affords structurally complex amines, present in many of the currently employed drugs. Furthermore, amines are also in bulk and fine chemicals used in the manufacture of plastics, textiles, surfactants, dyes, and many more 5. Amides play a central role in the chemistry of life, as they are the key elements to generate peptides and proteins from amino acid monomers. At the same time, they are present in artificial

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Section: Related Catalytic Hydrogenative Transformationsmentioning

confidence: 99%

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

et al. 2020

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“…[66][67][68][69][70][71][72] Among biomass materials, triglycerides serve as the most important feedstocks for the synthesis of fatty amines, amides, nitriles and alcohols used in the production of surfactants, polymers and other useful commodity chemicals. 73 However, benign manufacturing processes for the direct transformation of triglycerides into these chemicals are not well developed. In this study, we demonstrated the potential applicability of Re(5)/TiO2 catalyzed hydrogenations to direct transformation of triglycerides into the corresponding alcohols.…”

Section: Selective Hydrogenation Of Triglyceridesmentioning

confidence: 99%

Mechanistic study of the selective hydrogenation of carboxylic acid derivatives over supported rhenium catalysts

Toyao

Wei

Siddiki

et al. 2019

Catal. Sci. Technol.

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“…Oils undergo the biocatalysis process using ethanolamide, as evidenced in the Mass spectrometry (MS) profile when samples showed characteristic signals ofFAAs, as observed in other characterization studies of these compounds using Fourier transform infrared analysis (FTIR), and in previous studies that have used the Gas chromatography mass spectrometry (GC-MS) technique to quantify fatty acid and fatty acid amide content in various sample types [47,51]. Other studies also have obtained fatty amides from direct amidation of triglycerides from other natural sources [38,52].…”

Section: Discussionmentioning

confidence: 73%

“…The most frequent biosynthetic routes for these endocannabinoids are through arachidonic acid and involve compounds that are easily obtained (by chemical synthesis) and can be developed in the presence of a metallic catalyst [32,33] or biocatalyst [34,35]. Another possibility is based on the direct reaction from rich fatty acid oils from plants with amine that appear to be feasible for a biosynthetic route [36][37][38].…”

Section: Introductionmentioning

confidence: 99%

Fatty Acid Amides Synthesized from Andiroba Oil (Carapa guianensis Aublet.) Exhibit Anticonvulsant Action with Modulation on GABA-A Receptor in Mice: A Putative Therapeutic Option

et al. 2020

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Epilepsy is a chronic neurological disease characterized by excessive neuronal activity leading to seizure; about 30% of affected patients suffer from the refractory and pharmacoresistant form of the disease. The anticonvulsant drugs currently used for seizure control are associated with adverse reactions, making it important to search for more effective drugs with fewer adverse reactions. There is increasing evidence that endocannabinoids can pharmacologically modulate action against seizure and antiepileptic disorders. Therefore, the objective of this study is to investigate the anticonvulsant effects of fatty acid amides (FAAs) in a pentylenetetrazole (PTZ)-induced seizure model in mice. FAAs (FAA1 and FAA2) are obtained from Carapa guianensis oil by biocatalysis and are characterized by Fourier Transform Infrared Analysis (FT-IR) and Gas Chromatography-Mass Spectrometry (GC-MS). Only FAA1 is effective in controlling the increased latency time of the first myoclonic jerk and in significantly decreasing the total duration of tonic-clonic seizures relative to the pentylenetetrazol model. Also, electrocortical alterations produced by pentylenetetrazol are reduced when treated by FAA1 that subsequently decreased wave amplitude and energy in Beta rhythm. The anticonvulsant effects of FAA1 are reversed by flumazenil, a benzodiazepine antagonist on Gamma-Aminobutyric Acid-A (GABA-A) receptors, indicating a mode of action via the benzodiazepine site of these receptors. To conclude, the FAA obtained from C. guianensis oil is promising against PTZ-induced seizures.

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Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis

Cited by 31 publications

References 74 publications

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

Mechanistic study of the selective hydrogenation of carboxylic acid derivatives over supported rhenium catalysts

Fatty Acid Amides Synthesized from Andiroba Oil (Carapa guianensis Aublet.) Exhibit Anticonvulsant Action with Modulation on GABA-A Receptor in Mice: A Putative Therapeutic Option

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