1761-71-3

Basic information

• Product Name: 4,4'-Diaminodicyclohexyl methane
• Synonyms: BIS-(P-AMINOCYCLOHEXYL)METHANE;BIS(4-AMINOCYCLOHEXYL)METHANE;4,4'-DIAMINODICYCLOHEXYLMETHANE;4,4'-METHYLENEBIS(CYCLOHEXYLAMINE);4,4-METHYLENEBIS(CYCLOHEXYLAMINE);4,4'-METHYLENEBIS(AMINOCYCLOHEXANE);PACM20;TIMTEC-BB SBB008433
• CAS NO: 1761-71-3
• Molecular Formula: C₁₃H₂₆N₂
• Molecular Weight: 210.36
• EINECS: 217-168-8
• Mol File: 1761-71-3.mol

Chemical Properties

• Melting Point: 60-65°C
• Boiling Point: 330-331°C
• Flash Point: >230 °F
• Appearance: yellowish white liquid or brown solid paste
• Density: 0.95 g/mL at 25 °C(lit.)
• Vapor Pressure: <0.1 mm Hg ( 38 °C)
• Refractive Index: 1.5032 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.87±0.70(Predicted)
• Water Solubility: Insoluble (
• BRN: 2079179
• CAS DataBase Reference: 4,4'-Diaminodicyclohexyl methane(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Diaminodicyclohexyl methane(1761-71-3)
• EPA Substance Registry System: 4,4'-Diaminodicyclohexyl methane(1761-71-3)

Safety Data

• Hazard Codes: T+,N,C
• Statements: 26-34-51/53-48/22-43-35-22
• Safety Statements: 26-28-36/37/39-45-61-50-14
• RIDADR: UN 2928 6.1/PG 2
• WGK Germany: 2
• RTECS: GX1530000
• F: 10-34
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1761-71-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1761-71-3 differently. You can refer to the following data:
1. 4,4'-Methylenebis(cyclohexylamine) is a potential high inhibitive and high temperature resistant shale inhibitor.
2. 4,4'-Diaminodicyclohexyl methane be used as organic intermediates and epoxy curing agents.
3. 4,4'-Diaminodicyclohexylmethane is used as epoxy curing agents. It is a versatile intermediate to produce leather, rubber products, plastics, dyes, and photo sensitive polymers. It is used in manufacturing diisocyanates and polyamides. It is also used as lubricant additive as and corrosion inhibitor.

Chemical Properties

Beige solidified mass or fragments

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 1156, 1953 DOI: 10.1021/ja01101a044

General Description

Yellowish white liquid or brown solid paste.

Air & Water Reactions

Sensitive to decomposition in air and light . Insoluble in water.

Reactivity Profile

4,4'-Diaminodicyclohexyl methane neutralizes acids in weakly exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: 4,4'-Diaminodicyclohexyl methane is corrosive.

Fire Hazard

4,4'-Diaminodicyclohexyl methane is probably combustible.

Flammability and Explosibility

Nonflammable

Upstream product

• 1208-52-2 2,4'-diaminodiphenylmethane 
• 26628-67-1 N-Methyl-4,4'-methylenedianiline 
• 101-77-9 4,4'-diamino diphenyl methane 
• 6582-52-1 2,2'-methylenedianiline 

Downstream Products

• 13474-64-1 bis-(4-dimethylamino-cyclohexyl)-methane 
• 6693-29-4 trans,trans-4,4′-diaminocyclohexylmethane 
• 6693-30-7 cis,trans-4,4′-diaminocyclohexylmethane 
• 6693-31-8 cis,cis-4,4′-diaminocyclohexylmethane 
• 13622-90-7 trans,trans-4,4'-diisocyanato dicyclohexylmethane 
• 59801-70-6 4,4'-(4,4'-methanediyl-dicyclohexyl)-bis-thiomorpholine 1,1,1',1'-tetraoxide 
• 61366-99-2 Bis-(4--cyclohexyl)-methan 
• 61796-68-7 Undec-10-enoic acid [4-(4-undec-10-enoylamino-cyclohexylmethyl)-cyclohexyl]-amide 
• 26118-88-7 Bis-<4-methylamidosulfonylamino-cyclohexyl>-methan 
• 106593-22-0 4,4'-methanediyl-bis-cyclohexanone dioxime 
• 73880-25-8 N,N'-(4,4'-Methylendicyclohexyl)bis<(trichlorvinyl)ketenimin> 
• 143957-75-9 4,4'-Methylenebis(nitrocyclohexane) 
• 99305-42-7 dibutyl (methylene-bis(cyclohexane-4,1,diyl))dicarbamate 
• 410090-47-0 4,4'-methylenebis(N,N'-tert-butyldimethylsilylcyclohexylamine) 

Relevant articles and documents

Ru/g-C3N4as an efficient catalyst for selective hydrogenation of aromatic diamines to alicyclic diamines

A series of Ru/g-C3N4materials with highly dispersed Ru were firstly prepared by an ultrasonic impregnation method using carbon nitride as a support. The catalysts were characterized by various techniques including BET and elemental analysis, ICP-AES, XPS, XRD, CO2-TPD and TEM. The results demonstrated that Ru/g-C3N4materials with a mesoporous structure and highly dispersed Ru were successfully prepared. The chemo-selective hydrogenation ofp-phenylenediamine (PPDA) to 1,4-cyclohexanediamine (CHDA) over Ru/g-C3N4as a model reaction was investigated in detail. PPDA conversion of 100% with a CHDA selectivity of more than 86% could be achieved under mild conditions. It can be inferred that the carbon nitride support possessed abundant basic sites and the Ru/g-C3N4-Tcatalysts provided suitable basicity for the aromatic ring hydrogenation. Compared to the N-free Ru/C catalyst, the involvement of nitrogen species in Ru/g-C3N4remarkably improved the catalytic performance. In addition, the recyclability of the catalyst demonstrated that the aggregation of Ru nanoparticles was responsible for the decrease of the catalytic activity. Furthermore, this strategy also could be expanded to the selective hydrogenation of other aromatic diamines to alicyclic diamines.

Method for preparing aliphatic amine through reduction of aromatic amine compound

The invention provides a method for preparing aliphatic amine through reduction of an aromatic amine compound. According to the method, the aromatic amine compound is taken as a reaction substrate, and is subjected to hydrogenation reaction with a supported ruthenium catalyst and a deamination retardant in a solvent, so that an aliphatic amine compound is obtained; the deamination retardant adoptsaluminum-containing inorganic salt. The method has the advantages that through the addition of the deamination retardant during catalytic hydrogenation reduction of aromatic amine, the frequency of deamination side reaction produced by target products is reduced, so that the yield of the target products is improved, and the production cost of the specific yield of the target products is reduced.By taking the preparation of PACM as an example, the yield of the target product PACM can reach greater than 98 percent, and the preparation method has an important application value for practical mass production in the industry.

4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol, and preparation method and application thereof

The invention provides 4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol, and a preparation method and an application thereof. According to the method, 4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol is synthesized by reaction of a byproduct 4-((4-cyclohexylamino)methyl)cyclohexanol in an HMDA reaction process with formaldehyde and hydrogen under the action of a catalyst. The obtained 4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol is purified and then can be used as a reactive catalyst for polyurethane foaming. The HMDA by-product is effectively utilized, the production cost is greatly reduced and resources are rationally utilized. 4-((4-(dimethylamino)cyclohexyl)methyl)cyclohexanol as the novel reactive catalyst is used for preparing polyisocyanurate/polyurethane and the like,has the characteristics of low odor and strong yellowing resistant ability, and the product has low VOC.

CATALYST AND METHOD FOR HYDROGENATION OF 4,4'-METHYLENEDIANILINE

Disclosed is a catalyst for hydrogenation of 4,4′-methylenedianiline (MDA), including a support, a magnesium-aluminum oxide layer covering the support, and a rhodium-ruthenium active layer loaded on the magnesium-aluminum oxide layer, wherein the rhodium and the ruthenium of the rhodium-ruthenium active layer have a weight ratio of 40:60 to 10:90. The hydrogenation catalyst can be collocated with hydrogen for hydrogenation of the MDA to form bis(para-amino cyclohexyl) methane (PACM), and the PACM contains O mol % to 25 mol % of (t,t)-isomer.

METHOD FOR PRODUCING (4-AMINOBENZYL) CYCLOHEXYLAMINE

PROBLEM TO BE SOLVED: To industrially produce (4-aminobenzyl) cyclohexylamine as a main product. SOLUTION: An aromatic ring hydrogenation reaction of methylenedianiline is performed with a catalyst comprising metal selected from the group consisting of rhodium, ruthenium, palladium, iridium, nickel, and cobalt under the condition of a hydrogen pressure in a reaction vessel of less than 5 MPa. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Catalyst and process for hydrogenating aromatics

The present invention relates to an eggshell catalyst comprising an active metal selected from the group consisting of ruthenium, rhodium, palladium, platinum and mixtures thereof, applied to a support material comprising silicon dioxide, wherein the pore volume of the support material is 0.6 to 1.0 ml/g, determined by Hg porosimetry, the BET surface area is 280 to 500 m2/g, and at least 90% of the pores present have a diameter of 6 to 12 nm, to a process for preparing this eggshell catalyst, to a process for hydrogenating an organic compound which comprises at least one hydrogenatable group using the eggshell catalyst, and to the use of the eggshell catalyst for hydrogenating an organic compound.

PROCESS FOR HYDROGENATING AROMATIC DI- AND POLYAMINES

A catalytic process for hydrogenating aromatic di- and polyamines with the aid of a selected catalyst system is provided, which comprises a mixture of a first heterogeneous catalyst and a second heterogeneous catalyst and a nitro compound (nitrate and/or nitrite salt). The first and second heterogeneous catalyst each independently comprise a metal selected from the group consisting of Cr, Mo, W, Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd and/or Pt and the metal selected for the second heterogeneous catalyst is different from the metal selected for the first heterogeneous catalyst. Hydrogenation of aromatic rings having two or more amino groups bound to the aromatic ring produces cycloaliphatic di- and polyamines, which are useful chemical intermediates, e.g., for further reaction with epoxides or isocyanates. The amino groups may also be converted to isocyanates via reaction with phosgene. The resulting cycloaliphatic di- and polyisocyanates may also be used as monomers for making polymers.

One pot catalytic NO2 reduction, ring hydrogenation, and N-alkylation from nitroarenes to generate alicyclic amines using Ru/C-NaNO 2

A report to produce alicyclic amines and subsequent N-alkylation with alcohols using Ru/C-NaNO2 catalyzed facile transformation of nitrobenzene was investigated. Effects of solvent, temperature, pressure, reaction time, and molar-ratio of substrate/catalyst on product composition were also studied. These mechanistic studies explain that nitrobenzene undergoes hydrogenation reaction in the following order; -NO2 reduction to -NH2, aromatic ring-hydrogenation to alicyclic, and from the reaction of alcohol to give N-alkylated amines. This investigation shed lights on possible application to polyurethane chemistry since these amines are used as important precursors for diisocyanates.

METHOD OF CONVEYING LIQUIDS

The present invention relates to a method of continuously conveying a liquid which is used as starting material in a chemical reaction by means of a displacement pump having physically separate forward-transport valves and a liquid-filled bidirectional flow line between displacement pump and forward-transport valves, wherein an auxiliary liquid which is a product or a starting material of the chemical reaction and has a melting point which is below the melting point or below the saturation temperature of the liquid to be conveyed is present in the bidirectional flow line. The present invention additionally provides for the use of a product formed by hydrogenation of an aromatic compound as auxiliary liquid for conveying an aromatic compound and also the use of an alcohol or an ester derived from alcohol and carboxylic acid as auxiliary liquid for conveying carboxylic acids or carboxylic acid derivatives.

METHOD FOR INTERMITTENT PREPARATION OF LOW CONTENT TRANS-TRANS ISOMER-CONTAINING 4,4'-DIAMINODICYCLOHEXYLMETHANE

The present invention discloses a method for intermittently producing 4,4'-diaminodicyclohexyl methane (H12MDA) with a low amount of the trans-trans isomer thereof, which comprises: controlling the reaction process by stopping the reaction when, except for a solvent, the reaction solution comprises MDA of 0-5 wt% and H6MAD of 1-20 wt%; and b) separating the reaction solution obtained from step a) by conventional means to obtain H12MDA product with desired purity, and allowing the un-reacted material and intermediate product to be recycled to the reactor after being accumulated. The method of the present invention decreases the amount of the trans-trans isomer in H12MDA, increases the yield of the reaction, and reduces the production cost. The present invention also provides a post treatment process of the reaction mixture.