Hydroaminomethylation of fatty acids with primary and secondary amines — A new route to interesting surfactant substrates

Behr, Arno; Fiene, Martin; Buß, Christian; Eilbracht, Peter

doi:10.1002/1438-9312(200008)102:7<467::aid-ejlt467>3.0.co;2-j

Cited by 64 publications

(34 citation statements)

References 13 publications

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“…Hydroformylation is an important part of the hydroaminomethylation, which is a three step autotandem catalysis catalyzed by a single catalyst [16,[18][19][20][21][22][23][24]. Past investigations have applied different renewables [25][26][27][28][29][30] in the hydroaminomethylation reaction to increase the sustainability of the overall reaction sequence.…”

Section: Introductionmentioning

confidence: 99%

Catalyst recycling in the hydroaminomethylation of methyl oleate: A route to novel polyamide monomers

Vorholt

Immohr

Ostrowski

et al. 2016

Euro J Lipid Sci & Tech

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This article describes the development of an effective thermomorphic multicomponent solvent (TMS) system for the production of branched polyamide monomers. In this system, methyl oleate, a renewable from fats and oils, and a functionalized amine are used as starting materials in a tandem catalytic reaction, which merges different reaction steps into a single preparative step. This particular TMS system consisted of a heptane/acetonitrile solvent mixture and made reusing the precious rhodium catalyst possible in three recycle runs. A constant yield of 61–65% was obtained for each run due to low‐catalyst leaching. Fortunately, the catalyst system does not require any additional phosphorous ligands and allows high yields. A scale‐up for the production of 10–11 g of the desired product in each run was realized. Subsequent hydrogenation of the product directly provided an amine ester, which is a valuable polyamide monomer. Practical applications: A method was developed to enable access to primary amines via hydroaminomethylation and hydrogenation. The product, a nitrile ester, is a valuable intermediate for polyamide monomers. This nitrile ester was successfully hydrogenated to an amine ester, which features a potential polyamide monomer directly. A catalyst recycle of the homogeneous rhodium complex within the hydroaminomethylation of methyl oleate and an amino nitrile was successfully carried out, enabling constant homogeneous catalyst activity over the course of three recycle runs. A scale‐up to obtain 10–11 g of the hydroaminomethylation product was realized. A general method is described for the conversion of methyl oleate within a hydroaminomethylation reaction. The catalyst can be recovered and reused. Valuable polyamide intermediates were obtained.

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Section: Introductionmentioning

confidence: 99%

Catalyst recycling in the hydroaminomethylation of methyl oleate: A route to novel polyamide monomers

Vorholt

Immohr

Ostrowski

et al. 2016

Euro J Lipid Sci & Tech

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“…Nearly quantitative yields can be achieved under mild conditions (140 7C and 10 bar synthesis gas), within 20 h [39]. Numerous amines like mor-pholine, valinol, hexyl amine, aspartic acid diethyl ester, and benzyl amine were applied [40]. The corresponding conversions and yields are listed in Table 4.…”

Section: Hydroaminomethylationsmentioning

confidence: 99%

The refinement of renewable resources: New important derivatives of fatty acids and glycerol

Behr

Gomes

2010

Euro J Lipid Sci & Tech

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121

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During the last years, the industrial significance of renewable resources has highly increased. The ever‐growing use of fossil resources for energy consumption, polymers, fine chemicals and pharmaceuticals and the therefore steadily increasing price favour the substitution of oil and gas by renewable resources. Here, especially products of catalytic functionalisations of vegetable fats and oils such as rapeseed oil, sunflower oil, palm oil or coconut oil play a decisive role. The present article gives a survey of several important catalytic functionalisations of fatty compounds and glycerol resulting in new attractive products. With their emerging properties, they could find a rapid introduction into the chemical market. Particularly the functionalisations via heterogeneous and homogeneous catalysis, like additions, reductions, oxidations and metathesis reactions, will be presented.

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“…Hydroaminomethylation is an excellent method to insert an amino function into the fatty acid chain [21,22]. Mechanistically, it is a tandem or domino reaction, which consists of several interlocking steps (see Fig.…”

Section: Catalytic Hydroaminomethylationmentioning

confidence: 99%

Catalytic Processes for the Technical Use of Natural Fats and Oils

Westfechtel²,

2008

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Vegetable fats such as rapeseed oil, sunflower oil, palm oil or coconut oil consisting of triglycerides offer different carbon chain distributions. The use of these raw materials for the production of industrial chemicals as well as for fuel (biodiesel), which is finally a substitution for mineral oil, is a political discussion with various facets. The basic products such as fatty acids, fatty alcohols, and esters have different physical properties and lead to various areas of application depending on the carbon chain distribution. While the chain length range of C 12 represents important raw materials for detergents, chain lengths of C 18 are used mainly in industrial applications, e.g. as lubricants. Natural fatty alcohols are produced by the heterogeneous catalyzed high-pressure hydrogenation of methyl esters or fatty acids. The unsaturated fats and oils can be derivatized catalytically by functionalization, oligomerization, oxidation or metathesis. Thereby, new functional groups are introduced into the oleochemical substrate. The carbon chain length can be increased or reduced respectively, or a branching in the fatty chain is introduced. Products with completely new properties and areas of applications are available due to these catalytic variations of fats and oils.

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Hydroaminomethylation of fatty acids with primary and secondary amines — A new route to interesting surfactant substrates

Cited by 64 publications

References 13 publications

Catalyst recycling in the hydroaminomethylation of methyl oleate: A route to novel polyamide monomers

Catalyst recycling in the hydroaminomethylation of methyl oleate: A route to novel polyamide monomers

The refinement of renewable resources: New important derivatives of fatty acids and glycerol

Catalytic Processes for the Technical Use of Natural Fats and Oils

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