Some carbon, nitrogen- and carbon, oxygen-bond forming additions to unsaturated fatty compounds

Biermann, Ursula; Fürmeier, Sandra; Metzger, Jürgen O.

doi:10.1002/(sici)1521-4133(199806)100:6<236::aid-lipi236>3.0.co;2-1

Cited by 8 publications

(4 citation statements)

References 28 publications

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“…The reactivity of the double bonds of fatty chains was widely explored in the design of bio-based materials. 9,10 Herein the synthesis of bio-based amine from vegetable oil was investigated even if several synthetic methods were already developed via aziridine, 18 hydrazine, 20,21 nitrile. 23 In this context, thiol-ene chemistry (TEC) represents a direct and efficient method for the introduction of amine group into vegetable oil.…”

Section: Synthesis Of Aminated Vegetable Oil By Uv Initiatedmentioning

confidence: 99%

“…Some attempts to convert lipids or compounds derived from lipids into amines or polyamines have been described. Biermann et al 18 reviewed different methods to functionalize unsaturated fatty acids. The use of manganese III acetate mediated addition of sodium azide followed by the catalytic reduction of the azide group to give the corresponding amine was explored but not extended to triglycerides.…”

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confidence: 99%

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A fully biobased epoxy resin from vegetable oils: From the synthesis of the precursors by thiol‐ene reaction to the study of the final material

Stemmelen

Pessel

Lapinte

et al. 2011

J. Polym. Sci. A Polym. Chem.

237

144

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A novel vegetable oil-based polyamine issued from grapeseed oil (GSO) was prepared using cysteamine chloride (CAHC) by thiol-ene coupling (TEC). The structure of the polyamine oil (AGSO) was carefully examined using a large range of chemical analyses (FTIR, 1 H NMR and 13 C NMR, LC-MS…). The effects of the amination of GSO on the vegetable oil properties were also studied using viscosimetry. Then, AGSO was employed as a novel curing agent for bio-based epoxy resin. The thermal crosslinking reaction between AGSO and epoxi-dized linseed oil (ELO) was studied by DSC and rheology. This study also dealt with the definition of the thermomechanical properties of the final material obtained by the mixing and curing of AGSO with ELO in stoichiometric proportions.

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Section: Synthesis Of Aminated Vegetable Oil By Uv Initiatedmentioning

confidence: 99%

mentioning

confidence: 99%

A fully biobased epoxy resin from vegetable oils: From the synthesis of the precursors by thiol‐ene reaction to the study of the final material

Stemmelen

Pessel

Lapinte

et al. 2011

J. Polym. Sci. A Polym. Chem.

237

144

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“…Biobased amine hardeners were synthesized from fatty acids, grapeseed oil and cardanol (Scheme 5). Different strategies for the amination of unsaturated fatty acids were reviewed by Metzger et al [85]. Most of the described approaches involve multistep procedures, which do not respect several of the principles of green chemistry.…”

Section: Copolymerization With Hardenersmentioning

confidence: 99%

Sustainable Synthetic Approaches for the Preparation of Plant Oil‐Based Thermosets

Llevot

2016

J Americ Oil Chem Soc

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a more sustainable future. Due to an ever-increasing population on our planet and industrial developments, a major focus is on energy and fuel supply, as well as chemical and polymer production. In search for alternatives to the finite fossil feedstocks, the renewability and structural diversity of biomass makes it an excellent candidate [1][2][3][4][5][6]. Especially in polymer science, the use of renewable resources has been intensively investigated and discussed in several reviews over the last years [7][8][9][10][11]. Amongst biomass, vegetable oils constitute a platform of aliphatic hydrocarbons, particularly studied as polymer precursors due to their good availability, low price, inherent biodegradability and potential for chemical modifications [12][13][14][15][16]. Vegetable oils are composed of triglycerides, which consist of three fatty acid chains esterified with glycerol. Fatty acids vary in their chain length, as well as degree and location of their unsaturations. The fatty acid structures of the plant oils discussed in this review are shown in Scheme 1 and the composition of these oils displayed in Table 1. The fatty acid composition of the triglycerides, depending on the plant origin, influences their properties significantly [14]. Well-defined fatty acids can be recovered after hydrolysis of triglycerides and further separation and purification [17]. The latter can be transformed into difunctional monomers for the synthesis of a broad range of thermoplastic polymers [18]. However, this additional step decreases the sustainability of the synthesis. Thus, the direct polymerization of poly-functional vegetable oils into thermoset polymers represents a "greener" approach towards polymeric materials.Thermosets are cross-linked polymeric materials known for their good thermomechanical properties and chemical resistance. The production of these polymers represents ~20% of the total annual polymer production [19]. Thermosets can be synthesized in different chemical ways and the production of biobased thermosets has been recently Abstract The good availability and high degree of functionalization possibilities of plant oils entitles them to be one of the most intensively studied renewable resources, especially in polymer science. However, in line with the principles of green chemistry, the use of renewable resources should be accompanied with catalytic procedures, comparably less or non-toxic chemicals, as well as reduction of waste and energy consumption to achieve an overall sustainable process. In this review, these aspects are addressed using the example of plant oil-based thermoset materials, which bear the advantage, in terms of sustainability, of not requiring a separation or purification step prior to polymerization. The direct homopolymerization of plant oils, as well as copolymerization, exclusively with other renewable resources, are highlighted. The sustainability of the synthesis of a broad range of thermosets including epoxy resins, polyurethane networks, polybenzoxazines and unsaturated poly...

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“…17 Numerous studies have analyzed a range of compounds prepared from benzene and unsaturated fatty acids. [18][19][20][21] A series of compounds were generated by the Friedel-Crafts alkylation which was confirmed to be phenyl octadecanoic acid isomers of phenyl at different positions under the influence of carbocation rearrangement, and most of the phenyl existed at the positions between C-6 and C-17. 22,23 The products were repeatedly crystallized at low temperature with solvents such as acetone and n-hexane, and pure 17-, 16-, 15-and 13-phenyl methyl stearate could be isolated, accounting for 3.6%, 2.3%, 2.6%, and 1.5%, with a purity of over 98%.…”

Section: Introductionmentioning

confidence: 99%

Carbocation rearrangement, methyl migration, and long-range hydrogen transfer in phenyl fatty acid esters

Lang,

Gang,

et al. 2023

Journal of Chemical Research

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Various isomers can be observed in the Friedel–Crafts alkylation of benzene. However, the mechanism and influence of these isomerization reactions were still unclear. In this work, several methyl phenylundecanoate were analyzed by gas chromatography–mass spectrometry to explore the isomerization of the Friedel–Crafts alkylation. The results showed that there were three isomerization reactions in the Friedel–Crafts alkylation reaction: five isomers of methyl 6–10-phenylundecanoate due to carbocation rearrangement, five isomers of methyl 6–9-methyldecanoate and methyl undecanoate due to methyl migration, and the loss of neutral alcohol molecular fragments due to hydrogen transfer. At higher reaction temperature, carbocation migration was more active and the formation of methyl undecanoate isomers was observed. There was a competitive relationship between the production of methyl undecanoate isomers and methyl phenylundecanoate isomers. In addition, the hydrogen transfer could be initiated in the presence of unsaturated bonds and alcohol molecules lost as a fragment. The hydrogen from the phenyl groups, which were at a different position on the carbon chain of fatty acid esters, could be transferred to the ester group. It was found that hydrogen could be transferred intramolecularly over a long range. This work revealed the isomerization process in the Friedel–Crafts alkylation and further deepened the understanding of alkylation.

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Some carbon, nitrogen- and carbon, oxygen-bond forming additions to unsaturated fatty compounds

Cited by 8 publications

References 28 publications

A fully biobased epoxy resin from vegetable oils: From the synthesis of the precursors by thiol‐ene reaction to the study of the final material

A fully biobased epoxy resin from vegetable oils: From the synthesis of the precursors by thiol‐ene reaction to the study of the final material

Sustainable Synthetic Approaches for the Preparation of Plant Oil‐Based Thermosets

Carbocation rearrangement, methyl migration, and long-range hydrogen transfer in phenyl fatty acid esters

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