6693-30-7

Usage

Type of compound

Combination of trans and cis isomers of cyclohexylamine

Usage

Production of polymers, pharmaceuticals, and agrochemicals

Classification

Diamine (contains two amine groups)

Physical state

Colorless liquid

Odor

Slightly ammonia-like

Application

Curing agent for epoxy resins

Additional uses

Production of flexible polyurethanes and adhesives

Pharmaceutical potential

Synthesis of various drugs

Safety precautions

Harmful if ingested or inhaled, can cause skin and eye irritation

Upstream product

• 620-92-8 bis-(4-hydroxyphenyl)methane 
• 101-77-9 4,4'-diamino diphenyl methane 
• 1761-71-3 4,4'-diaminodicyclohexylmethane 
• 52506-03-3 (cis-4-acetylamino-cyclohexyl)-(trans-4-acetylamino-cyclohexyl)-methane 
• 62-53-3 aniline 

Downstream Products

• 112343-42-7 (cis-4-formylamino-cyclohexyl)-(trans-4-formylamino-cyclohexyl)-methane 
• 52506-03-3 (cis-4-acetylamino-cyclohexyl)-(trans-4-acetylamino-cyclohexyl)-methane 
• 135269-81-7 bis-(cis-4-acetylamino-cyclohexyl)-methane 

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.

The Rhodium Catalysed Direct Conversion of Phenols to Primary Cyclohexylamines

Cyclohexylamines are important intermediates in chemical industry, which are currently produced from petrochemical sources. Phenols, however, are an attractive sustainable feedstock. We here demonstrate the transformation of phenols with ammonia to primary cyclohexylamines. In contrast to previously reported chemistry which used palladium catalysts, we here show that rhodium is an excellent catalyst for the formation of primary cyclohexylamines. Different parameters were studied and it was shown that the reaction is applicable to a scope of phenolic compounds providing high selectivity.

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.

Potential DNA bis-intercalating agents. Synthesis and antitumor activity of N,N-Methylenedi-4,1-cyclohexanediyl- bis(9-acridinamine) isomers

We describe the synthesis and antitumor activity of three novel isomeric bis-acridines 14-16 possessing a non-aromatic, semi-rigid dicyclohexylmethylene tether.

CO-PRODUCTION OF CYCLOHEXYLAMINE AND BIS-(PARA-AMINOCYCLOHEXYL) METHANE

Embodiments of the present invention disclose a process for the co-production of bis(para-aminocyclohexyl) methane (PACM). Also disclosed are articles of manufacture made using PACM produced by methods of this invention. The methods of the present invention generally include using a first mixture having methylene di-aniline (MDA) and a second aromatic amine. The first mixture has less than 15% polymeric MDA by weight and the second aromatic amine is present in an amount to render the first mixture a liquid. The first mixture is hydrogenated to produce a product mixture comprising PACM and at least one second non-aromatic amine.