6693-29-4

Usage

Uses

Used in Epoxy Resin Industry:
[trans(trans)]-4,4'-methylenebis(cyclohexylamine) is used as a curing agent for epoxy resins. It improves the impact resistance and flexibility of these resins, which is crucial for applications that require toughness and durability.
Used in Polyurethane Production:
In the polyurethane industry, [trans(trans)]-4,4'-methylenebis(cyclohexylamine) is utilized in the production process. Its incorporation contributes to the enhancement of the material's overall performance, making it suitable for a wide range of applications.

Upstream product

• 101-77-9 4,4'-diamino diphenyl methane 
• 620-92-8 bis-(4-hydroxyphenyl)methane 
• 1761-71-3 4,4'-diaminodicyclohexylmethane 

Downstream Products

• 52506-03-3 bis-(trans-4-acetylamino-cyclohexyl)-methane 
• 61366-99-2 C₁₉H₃₄Cl₂N₄O₂ 
• 60324-95-0 C₁₉H₃₂Cl₂N₆O₄ 

Relevant academic research and scientific papers

Ceria supported Ru0-Ruδ+ clusters as efficient catalyst for arenes hydrogenation

Selective hydrogenation of aromatic amines, especially chemicals such as aniline and bis(4-aminocyclohexyl)methane for non-yellowing polyurethane, is of particular interests due to the extensive applications. To conquer the existing difficulties in selective hydrogenation, the Ru0-Ruδ+/CeO2 catalyst with solid frustrated Lewis pairs was developed for aromatic amines hydrogenation with excellent activity and selectivity under relative milder conditions. The morphology, electronic and chemical properties, especially the Ru0-Ruδ+ clusters and reducible ceria were characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electronic microscopy (SEM), X-ray photoelectron spectroscopy (XPS), CO2 temperature programmed desorption (CO2-TPD), H2 temperature programmed reduction (H2-TPR), H2 diffuse reflectance Fourier transform infrared spectroscopy (H2-DRIFT), Raman, etc. The 2% Ru/CeO2 catalyst exhibited good conversion of 95% and selectivity greater than 99% toward cyclohexylamine. The volcano curve describing the activity and Ru state was found. Owning to the “acidic site isolation” by surrounding alkaline sites, condensation between the neighboring amine molecules could be effectively suppressed. The catalyst also showed good stability and applicability for other aromatic amines and heteroarenes containing different functional groups.

Ni-Catalyzed reductive amination of phenols with ammonia or amines into cyclohexylamines

Phenol and its derivatives, which naturally occur in lignocellulose, can be considered as a renewable feedstock not only for aromatic, but also for alicyclic compounds, such as primary and N-substituted cyclohexylamines. So far, the latter are mostly produced from non-renewable starting materials like benzene via problematic nitration/reduction or cross-coupling routes. Herein, an efficient reductive amination of phenol with ammonia or amines is demonstrated, for the first time without the need for rare and expensive noble metals and without using any additives. Various supported Ni catalysts were screened and we elucidated the influence of the key parameters, including the acid-base properties of the supporting material. Acquired knowledge was then applied to different phenol-ammonia/amine combinations, resulting in the synthesis of various primary, secondary and tertiary cyclohexylamines in fair to very high yields.

PROCESS FOR HYDROGENATING 4,4'-METHYLENEDIANILINE

The present invention relates to a process for hydrogenating 4,4′-methylenedianiline and/or polymeric MDA with hydrogen in the presence of a catalyst comprising ruthenium on a zirconium oxide support material, and also to the use of a catalyst comprising ruthenium on a zirconium oxide support material for hydrogenating 4,4′-methylenedianiline and/or polymeric MDA.

METHOD FOR PREPARING DIAMINO-DICYCLOHEXYL METHANE

Disclosed is a method for preparing diamino-dicyclohexyl methane (H12MDA) by hydrogenation of diamino-diphenyl methane (MDA). In the process, 4,4′-MDA used as the starting material is firstly hydrogenated to prepare 4,4′-H12MDA. When the activity of the catalyst is reduced, the feed is switched from 4,4′-MDA to the mixture of 2,4′-MDA and 4,4′-MDA, and then when the conversion is stabilized, the feed is switched to 4,4′-MDA again. The deactivated catalyst is activated on line by switching the feed to the mixture of 2,4′-MDA and 4,4′-MDA. 4,4′-H12MDA having the trans-trans isomer content of 16?24 wt % is produced, and the mixture of 2,4′-H12MDA and 4,4′-H12MDA is also produced, wherein the content of 2,4′-H12MDA in the mixture is 4?15 wt %.

Process for hydrogenation of aromatic amines in presence of a supported ruthenium catalyst

Hydrogenation of an amine with at least one aromatic ring-bonded amine group by reaction with hydrogen in presence of a supported catalyst with 0.01-20 wt.% active metal comprising ruthenium alone or with a sub-Group I, VII or VIII metal is such that the support has: (I) a BET surface area above 30 but below 70 m2/g; and (II) a macropore (diameter above 50nm) content above 50% and a mesopore (diameter 2-50nm) content below 50%.