Development and evaluation of gas and liquid chromatographic methods for the analysis of fatty amines

Breitbach, Zachary S.; Weatherly, Choyce A.; Woods, Ross M.; Xu, Chengdong; Vale, Glenda; Berthod, Alain; Armstrong, Daniel W.

doi:10.1002/jssc.201301265

Cited by 13 publications

(7 citation statements)

References 23 publications

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“…For example, for the production of fatty amines (approx. 800,000 t in 2011 [2]) different synthesis routes are known. In addition to the option of stoichiometric reducing agents such as NaBH 4 [3] also catalytic hydrogenation reactions can be applied, and their importance is steadily increasing.…”

Section: Introductionmentioning

confidence: 99%

Rh-Catalyzed Reductive Amination of Undecanal in an Aqueous Microemulsion System Using a Non-Ionic Surfactant

2021

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The homogeneously catalyzed reductive amination of the long-chain aldehyde undecanal with diethylamine was performed in an aqueous microemulsion system using the non-ionic surfactant Marlophen NP8. The experiments showed that the used water-soluble rhodium/SulfoXantphos catalyst system is suitable for this reaction. The Rh-catalyzed formation of the alcohol by-product can be completely suppressed by the use of carbon monoxide with its stabilizing effect of the catalyst system. In addition to pressure and temperature, the most important parameters for the reaction performance of the reductive amination are the concentrations of reactants. Especially, the initial concentration of the aldehyde has a strong impact on the chemoselectivity, and the formation of aldol by-product due to the fact that both, the enamine condensation and the aldol condensation are equilibrium reactions.

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Section: Introductionmentioning

confidence: 99%

Rh-Catalyzed Reductive Amination of Undecanal in an Aqueous Microemulsion System Using a Non-Ionic Surfactant

2021

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“…[9,43] Directa pplicationso fs uch nitrilesa re particularly known for short-chain nitriles,s uch as acetonitrile, whereas al arge portion of the longer-chaina liphatic nitriles serve as intermediates for hydrogenation to the corresponding amines.F or example, the resulting fatty amines canb ef ound in many household products, as well as industrial products, with aw orldwide demand reported to be 800 000 tons in 2011. [44] Furthermore, here, fats and oils as renewable building blocksc an serve as araw-material source and, thus, as an alternative to petrochemicals.…”

Section: Synthesis Of Aliphatic Nitriles With Utilization As Bulk Andmentioning

confidence: 99%

Synthetic Processes toward Nitriles without the Use of Cyanide: A Biocatalytic Concept Based on Dehydration of Aldoximes in Water

Hinzmann

Betke

Asano

et al. 2021

Chemistry A European J

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While belonging to the mostf undamentalf unctional groups,n itrilesr epresent ac lass of compound that still raises challenges in terms of an efficient, cost-effective, generala nd,a tt he same time, sustainable way for their synthesis. Complementing existing chemical routes, recently ac yanide-free enzymatic process technology based on the use of an aldoximed ehydratase (Oxd) as a biocatalyst component has been developed and successfully applied fort he synthesis of ar ange of nitrile products. In these biotransformations,t he Oxd enzymes catalyze the dehydration of aldoximes as readily available substrates to the nitrile products.H erein, these developments with such enzymesa re summarized, with as trong focus on synthetic applications. It is demonstrated that this biocatalytic technology has the potential to "cross the bridge" between the production of fine chemicals and pharmaceuticals, on one hand, and bulk and commodity chemicals, on the other.

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“…Fatty amines play an important role in the chemical industry since such compounds are either directly used in home products such as fabric softeners, dishwashing liquids, car wash detergents, or carpet cleaners or in a broad range of industrial DOI: 10.1002/ejlt.201900163 products, for example, lubricating additives, flotation agents, dispersants, emulsifiers, corrosion inhibitors, fungicides, and bactericides. [1][2][3] The worldwide demand of fatty amines was 800 000 tons in 2011, [3] thus representing a further large-scale option for the use of fats and oils as renewable building blocks and alternative raw material sources to petrochemicals. Among them, primary fatty amine are highly requested target products.…”

Section: Introductionmentioning

confidence: 99%

Selective Hydrogenation of Fatty Nitriles to Primary Fatty Amines: Catalyst Evaluation and Optimization Starting from Octanenitrile

Hinzmann

Gröger

2019

Euro J Lipid Sci & Tech

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In this contribution, an evaluation of the potential of various homogeneous and heterogeneous catalysts for a selective hydrogenation of fatty nitriles toward primary amines is reported exemplified for the conversion of octanenitrile into octane-1-amine as a model reaction. When using heterogeneous catalysts such as the ruthenium catalyst Ru/C, the palladium catalyst Pd/C, and the platinum catalyst Pt/Al 2 O 3 , low selectivities in the hydrogenation are observed, thus leading to a large portion of secondary and tertiary amine side-products. For example, when using Ru/C as a heterogeneous catalyst, high conversions of up to 99% are obtained but the selectivity remains low with a percentage of the primary amine being at 60% at the highest. The study further reveals a high potential of homogeneous ruthenium and manganese catalysts. When also taking into account economical considerations with respect to the metal price, in particular, manganese catalysts turn out to be attractive for the desired transformation and their application in the model reaction leads to the desired primary amine product with excellent conversion, selectivity, and high yield. Practical Applications: This work describes an optimized hydrogenation process for transforming fatty nitriles to their corresponding primary amines. In general, fatty amines belong to the most applied fatty acid-derived compounds in the chemical industry with an annual product volume exceeding 800 000 tons per year in 2011 and are widely required in the chemical industry since such compounds are either directly used in home products such as fabric softeners, dishwashing liquids, car wash detergents, or carpet cleaners or in a broad range of industrial products, for example, lubricating additives, flotation agents, dispersants, emulsifiers, corrosion inhibitors, fungicides, and bactericides, showing additional major applications, e.g., in the detergents industry. Among them primary amines play an important industrial role. However, a major concern of current processes is the lack of selectivity and the formation of secondary and tertiary amines as side-products. By modifying a recently developed catalytic system based on manganese as economically attractive and environmentally benign metal component an efficient and selective access to fatty amines when starting from the corresponding nitriles is achieved. For example, hydrogenation of octanenitrile leads to a synthesis of octane-1-amine with >99% conversion and excellent selectivity with formation of secondary and tertiary amine side-products being suppressed to an amount of <1%.

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Development and evaluation of gas and liquid chromatographic methods for the analysis of fatty amines

Cited by 13 publications

References 23 publications

Rh-Catalyzed Reductive Amination of Undecanal in an Aqueous Microemulsion System Using a Non-Ionic Surfactant

Rh-Catalyzed Reductive Amination of Undecanal in an Aqueous Microemulsion System Using a Non-Ionic Surfactant

Synthetic Processes toward Nitriles without the Use of Cyanide: A Biocatalytic Concept Based on Dehydration of Aldoximes in Water

Selective Hydrogenation of Fatty Nitriles to Primary Fatty Amines: Catalyst Evaluation and Optimization Starting from Octanenitrile

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