Amidation of triglycerides by amino alcohols and their impact on plant oil-derived polymers

Yuan, Liang; Wang, Zhongkai; Trenor, Nathan M.; Tang, Chuanbing

doi:10.1039/c6py00048g

Cited by 54 publications

(45 citation statements)

References 56 publications

(62 reference statements)

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“…Industrially, fatty amides are currently produced by using a two‐step process (Scheme ): the conversion of triglycerides into fatty acid esters, followed by a high‐temperature aminolysis to produce fatty amides . Several studies have reported the direct amidation of triglycerides with amino alcohols or isopropylamine by using basic promoters such as methoxides, NaOH/CaO, Na‐doped Ca(OH) 2 , and Li‐doped CaO, or by using solid acid catalysts or biocatalysts . However, reports on the direct amidation of triglycerides with NH 3 remain scarce.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2019

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Section: Introductionmentioning

confidence: 99%

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

et al. 2019

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“…Moreover, the appearance of a peak at 2.05 ppm can be ascribed to −CH 2 − protons in the α position of the CO of an amide group, according to the literature . As can be seen in Scheme , the trans ‐amidification yield decreases the content of functionalized triglycerides and increases the formation of free aliphatic chains, resulting in a decrease in the final cross‐linking ratio.…”

Section: Resultsmentioning

confidence: 71%

“…[36][37][38] As can be seen in Scheme 1, the trans-amidification yield decreases the content of functionalized triglycerides and increases the formation of free aliphatic chains, resulting in a decrease in the final cross-linking ratio. [36][37][38] As can be seen in Scheme 1, the trans-amidification yield decreases the content of functionalized triglycerides and increases the formation of free aliphatic chains, resulting in a decrease in the final cross-linking ratio.…”

Section: H Nmr Monitoring Of Reactionmentioning

confidence: 99%

Preparation and Spectroscopic Characterization of Si‐Coated Vegetable Oils and their Application in In Situ Curing of Hybrid Coatings

Maurin‐Pasturel

Lemor²,

Robin

et al. 2019

Euro J Lipid Sci & Tech

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The modification of natural oils with heteroatoms leads to materials that can be employed in various areas thanks to their specific properties. Here, a solventless chemical modification of epoxidized linseed oil with an aminosilane without a catalyst is developed, and a detailed study of the chemical reactions involved during the process is reported. The mechanism results in two competitive reactions: the ring‐opening of epoxides and trans‐amidification of triglycerides with the amine functional group of aminosilane. These competitive reactions are shown by infrared spectroscopy (FTIR) and 1H, 13C, and 2D nuclear magnetic resonance (NMR). Even if the epoxy ring‐opening remains the major route, the trans‐amidification cannot be ignored. These modified oils are very reactive under atmospheric conditions by cross‐linking according to a polycondensation of the −Si(OMe)3 moieties or via a sol‐gel process and lead to a rapid hardening. The final material gives hydrophobic and glossy coatings on cellulose and glass. Practical Applications: This paper details the easy route to convert vegetable oils into coatings by crosslinking under mild conditions. These bio‐based materials can be applied as oil‐based impregnating products for exterior wood protection and in the hydrophobization of paper. Epoxidized linseed oil is chemically modified with an amino silane to make it reactive under atmospheric conditions. The chemical reaction is detailed and side reactions identified. Polycondensation of the grafted alkoxysilanes leads to hydrophobic coatings on cellulose and glass.

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“…The synthesized methacrylate monomers based on high oleic soybean oil, depending on the nature of the branches in the side chain, have a wide range of glass transition temperatures [ 16 ]. In further studies, Tang and co-authors used more than twenty amino alcohols to establish the mechanism of amidation of plant oils, in particular high-oleic soybean oil [ 8 ]. Depending on the nature of the acyl fatty acid and amide structures, the polymers have a wide range of glass transition temperatures – from viscoelastic to thermoplastic materials.…”

Section: Features Of Synthesis Of Vinyl Monomers From Plant Oilsmentioning

confidence: 99%

“…The total production of plant oils in the world in 2019 amounted to more than 200 million tons, of which about 15% are used as raw materials for the synthesis of new chemical compounds and materials [ 6 ]. The presence of plant oils or their derivatives (fatty acids) in various compositions of polymeric materials improves their optical (gloss), physical (flexibility, adhesion) [ 7 , 8 ], and chemical (resistance to water and chemicals) properties [ 9 ]. The synthesis of biobased monomers from renewable resources is a promising platform for the synthesis and implementation of new environmentally friendly industrial polymer materials [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Non-Conventional Features of Plant Oil-Based Acrylic Monomers in Emulsion Polymerization

et al. 2020

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In recent years, polymer chemistry has experienced an intensive development of a new field regarding the synthesis of aliphatic and aromatic biobased monomers obtained from renewable plant sources. A one-step process for the synthesis of new vinyl monomers by the reaction of direct transesterification of plant oil triglycerides with N-(hydroxyethyl)acrylamide has been recently invented to yield plant oil-based monomers (POBMs). The features of the POBM chemical structure, containing both a polar (hydrophilic) fragment capable of electrostatic interactions, and hydrophobic acyl fatty acid moieties (C15-C17) capable of van der Waals interactions, ensures the participation of the POBMs fragments of polymers in intermolecular interactions before and during polymerization. The use of the POBMs with different unsaturations in copolymerization reactions with conventional vinyl monomers allows for obtaining copolymers with enhanced hydrophobicity, provides a mechanism of internal plasticization and control of crosslinking degree. Synthesized latexes and latex polymers are promising candidates for the formation of hydrophobic polymer coatings with controlled physical and mechanical properties through the targeted control of the content of different POBM units with different degrees of unsaturation in the latex polymers.

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Amidation of triglycerides by amino alcohols and their impact on plant oil-derived polymers

Abstract: Amidation of plant oils with amino alcohols was methodologically examined.

Cited by 54 publications

References 56 publications

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

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

Preparation and Spectroscopic Characterization of Si‐Coated Vegetable Oils and their Application in In Situ Curing of Hybrid Coatings

Non-Conventional Features of Plant Oil-Based Acrylic Monomers in Emulsion Polymerization

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