4,4'-Diaminodicyclohexyl methane Chemical Properties

Melting point:

60-65°C

Boiling point:

330-331°C

Density 

0.95 g/mL at 25 °C(lit.)

vapor pressure 

<0.1 mm Hg ( 38 °C)

refractive index 

1.5032 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

powder to lump to clear liquid

pka

10.87±0.70(Predicted)

color 

White or Colorless to Almost white or Almost colorless

Odor

Ammonia odor

Water Solubility 

Insoluble (<0.1 g/100 mL)

BRN 

2079179

InChI

1S/C13H26N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h10-13H,1-9,14-15H2

InChIKey

DZIHTWJGPDVSGE-UHFFFAOYSA-N

SMILES

NC1CCC(CC1)CC2CCC(N)CC2

LogP

2.03 at 25℃

CAS DataBase Reference

1761-71-3(CAS DataBase Reference)

NIST Chemistry Reference

Cyclohexanamine, 4,4'-methylenebis-(1761-71-3)

EPA Substance Registry System

4,4'-Methylenebis(cyclohexylamine) (1761-71-3)

Safety Information

Hazard Codes 

T+,N,C

Risk 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 

TSCA listed

HazardClass 

8

PackingGroup 

III

HS Code 

29213000

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Acute Tox. 4 Oral
Aquatic Chronic 2
Skin Corr. 1B
Skin Sens. 1
STOT RE 2 Oral

Toxicity

LC50 inhalation in mouse: 400mg/m3/4H

MSDS

• Language:English Provider:Bis(4-aminocyclohexyl)methane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4,4'-Diaminodicyclohexyl methane Usage And Synthesis

Uses

4,4'-Methylenebis(cyclohexylamine) is a potential high inhibitive and high temperature resistant shale inhibitor.

Description

4,4'-Diaminodicyclohexyl methane is a sodium salt of a cyclic anhydride that is used as a specific treatment for removing dodecanedioic acid from fatty acids. The reaction solution is stable at pH 4-5 and has a viscosity of less than 1000 cps. It has good stability in the presence of amines and can be used in chromatographic science, including chromatography and gas-liquid chromatography. The UV absorption maxima for the acid complex are 195 nm and 240 nm.

Chemical Properties

Beige solidified mass or fragments

Uses

4,4'-Diaminodicyclohexyl methane be used as organic intermediates and epoxy curing agents.

Uses

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.

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

Non flammable

Toxicology

On resorption, predominant clinical signs of intoxication were hyperexcitability, excessive salivation, and convulsions in animals; repeated oral dosing (50 – 100 mg kg -1 d -1 in rats and mice for 10 and 16 d, respectively, 50 mg/kg in dogs for up to 82 weeks) resulted in gastrointestinal hemorrhagic inflammations, nephritis, and fatty changes to the liver. No changes in methemoglobin or in other hematological parameters were induced in cats on repeated doses of 50 and 100 mg kg -1 d -1, given twice per week over 2 months. Several in vitro and in vivo mutagenicity studies gave no evidence of a mutagenic or clastogenic potential.

Synthesis

1g of titanium dioxide powder was dispersed in 40mL of water and methanol mixture (water and methanol volume ratio of 9:1), stirred well, then added 60??mol/ml of RuCl3-xH2O dark brown aqueous solution, control the amount of addition so that the ruthenium in the titanium dioxide loading of 5wt%. After sealing and stirring for 3 hours at room temperature, 1M sodium hydroxide solution was added dropwise to pH10.5 and continued to seal and stir for 20 hours, centrifuged and washed with a mixture of water and ethanol for 3-5 times, and then vacuum-dried at 60??C overnight to obtain a light-green powder, and the catalyst was obtained.

The freshly prepared catalyst was placed in a reaction kettle, a certain volume of solvent was added, and an appropriate amount of 4,4'-diaminodiphenylmethane (MDA) was added, and the molar ratio of ruthenium in the MDA and the catalyst 4 was controlled to be 10,000, and the reaction kettle was closed and rinsed with hydrogen for 10 times, then the reaction kettle was heated up to 150 ?? to start the reaction, and the molar ratio of hydrogen and MDA was controlled to not be less than 80, and the hydrogen and MDA were controlled to be not less than 80. The molar ratio of hydrogen to MDA was controlled to be not less than 80, and the pressure of hydrogen was 1-5 MPa, and real-time samples were taken to check the reaction products and conversion rates.The benzene ring in MDA could be rapidly hydrogenated to produce a single benzene ring hydrogenation product (+6H) and a bis-benzene ring hydrogenation product, 4,4'-diaminodicyclohexylmethane (+12H) without deaminated products, which is worth mentioning that the 4,4'-diaminodicyclohexylmethane (+12H) is not deaminated. '-diaminodicyclohexylmethane is a feedstock compound for specialty nylons.

Toxics Screening Level

The initial threshold screening level (ITSL) for 4,4'-diaminodicyclohexylmethane is 6 μg/m3 based on an annual averaging time.

4,4'-Diaminodicyclohexyl methane (1761-71-3)Related Product Information

• Tris(hydroxymethyl)aminomethane
• Dimethoxymethane
• Dicyclohexylcarbodiimide
• 4,4'-Methylenedianiline
• Dicyclohexylchlorophosphine
• Cyclohexylamine
• Molasses
• Sodium N-cyclohexylsulfamate
• N,N'-(METHYLENEDICYCLOHEXYL)BIS[4-(2-PYRIDYL)-1-PIPERAZINECARBOXAMIDE]
• 4,4'-METHYLENEBIS(2-METHYLCYCLOHEXYLAMINE)
• Methylene-bis(4-cyclohexylisocyanate)
• 4,4'-METHYLENEBIS-(N,N-DIMETHYLCYCLOHEXANAMINE)
• mebezonium iodide
• dicyclohexylmethane
• 4,4'-Diaminodicyclohexyl methane
• Bis-(4-aminocyclohexyl)-methane carbamate
• 2-CYANO-N-(4-[4-[2-CYANO-3-(3,4-DIHYDROXYPHENYL)-ACRYLOYLAMINO]-CYCLOHEXYLMETHYL]-CYCLOHEXYL)-3-(3,4-DIHYDROXYPHENYL)-ACRYLAMIDE
• N,N'-(methylenedicyclohexane-1,4-diyl)distearamide