https://aiche.onlinelibrary.wiley.com/doi/pdf/10.1002/amp2.10042

Propoxylation of fatty amines: Switching from batch to flow

The mechanism of the autocatalytic alkoxylation of fatty amines was elucidated using a combined experimental and theoretical approach. The kinetic parameters of the elementary reaction steps are fitted to the experimental data gained in semibatch for propylene and butylene oxides with dodecylamine. A quality-of-fit sensitivity study was conducted to assess the robustness and accuracy of the model. Herein, we identified the kinetic parameters that are either crucial for a good fit or rate controlling in terms of the overall kinetics. It was found that the critical steps are the activation of the epoxide ring by a hydroxyl group present on either the intermediate or final product, highlighting the autocatalytic nature of the reaction. Furthermore, we introduced a so-called degree of conversion control to characterize the importance of each elementary reaction step toward the epoxide conversion. The degree of conversion control showed that the uncatalyzed route toward the secondary amine is only influential at low conversion. At higher conversion the route via the catalytic intermediate dominates. Alternative mechanisms were investigated as well but did not significantly improve the quality of fitting and were thus discarded.

Detailed chemomechanistic sensitivity study on the alkoxylation of fatty amines

The cyclisation of ethoxylates of ethylenediamine (EDA) and piperazina (PIP) over ZSM-5 zeolite to 1,4-diazabicyclo[2,2,2]octane (TEDA) was studied. It was found that monoethoxylates of EDA and PIP provide significantly higher yield then any of the bisethoxylates investigated. All of tested compounds provide over the zeolite catalyst unsaturated cyclic compounds, mostly pyrazine derivatives.

Reactions of ethoxylates of ethylenediamine and piperazine over zsm-5 zeolite

Ethoxylation kinetics of isomeric and secondary alcohols are crucial to the ethylene oxide (EO) distribution of alcohol ethoxylates, which might be influenced by basicity intensity of catalysts, similar as the ethoxylation of linear alcohols in the presence of alkali hydroxides/alkoxides catalysts; but may be affected by the steric hindrance caused by the branch chains of the ethoxylates. A kinetic model is derived based on SN2 mechanism of base-catalyzed ethoxylation of fatty alcohols, and experimentally verified with the initial kinetic characteristics in ethoxylation of 2-ethylhexanol (2-EH), 2-octanol (2-OT) and 1-octanol (1-OT) catalyzed by alkali hydroxides/alkoxides, CH3OK, CH3ONa, KOH and NaOH by GC monitoring the yields of each monodisperse oligo (ethylene glycol) iso/sec/n-octyl ethers. With same catalyst, the ethoxylation rate constants of mono- (k0′) and di-adduction (k1′) products of iso/sec/n-octanol are dominated by the steric hindrance of the octanols, resulting higher k1′/k0′ for 2-EH and 2-OT than that of 1-OT; but the effect of the steric hindrance on initial EO distribution could be eliminated by stronger catalyst basicity. This finding suggests that the stronger catalyst basicity is beneficial to suppress the adverse steric hindrance of branch octanols (2-EH and 2-OT) on initial adduction rates, therefore resulting in a narrower EO distribution profile of the ethoxylates. 

Cascade Kinetic Model on Ethoxylation of Iso/Sec/n-Octanol Catalyzed by Alkali Hydroxides/Alkoxides and Its Experimental Verification

Monoethanolamine oxypropylation kinetics

The butoxylation of dodecylamine: Reaction mechanism and kinetics

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The butoxylation of dodecylamine: Reaction mechanism and kinetics