2-Ethyl-4-methylimidazole Chemical Properties

Melting point:

47-54 °C (lit.)

Boiling point:

292-295 °C (lit.)

Density 

0.975 g/mL at 25 °C (lit.)

vapor pressure 

0.028Pa at 20℃

refractive index 

n20/D 1.5(lit.)

Flash point:

280 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to lump to clear liquid

pka

15.32±0.10(Predicted)

Specific Gravity

0.975

color 

White or Colorless to Yellow to Orange

Water Solubility 

210 g/L (20 ºC)

BRN 

1711

InChIKey

ULKLGIFJWFIQFF-UHFFFAOYSA-N

LogP

1.13 at 25℃

CAS DataBase Reference

931-36-2(CAS DataBase Reference)

NIST Chemistry Reference

1H-Imidazole, 2-ethyl-4-methyl-(931-36-2)

EPA Substance Registry System

2-Ethyl-4-methylimidazole (931-36-2)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

2

RTECS 

NI6147500

F 

10

Hazard Note 

Irritant/Harmful

TSCA 

Yes

HS Code 

29339900

MSDS

• Language:English Provider:2-Ethyl-4-methylimidazole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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2-Ethyl-4-methylimidazole Usage And Synthesis

Chemical Properties

clear yellow viscous liquid after melting

Uses

Curing epoxy-resin systems.

Uses

2-Ethyl-4-methylimidazole can be used as a:

• cross-linker for epoxy resins to synthesize network polymers with improved thermal resistance and physical properties.
• curing agent for polysiloxane episulfide resin (PSER).
• catalyst to promote curing of blends of hyperbranched aromatic epoxy polymer and bisphenol F diglycidyl ether.

Definition

ChEBI: 5K8XI641G3 is a member of imidazoles.

Application

2-Ethyl-4-methylimidazole is an important synthetic intermediate. It is used as an intermediate in pharmaceuticals, agrochemicals, dyes, textile auxiliaries, pigments and other organic chemicals. It can be used as a basic ingredient in other active ingredients, as a catalyst in chemical reactions, and in the curing of epoxy resins.

Preparation

2-Ethyl-4-methylimidazole was prepared as follows: diamine and propionitrile have a cyclization reaction sequentially at the temperature of 80-110 °C and 120-140 °C under the catalysis of a catalyst; a product after the cyclization reaction has a dehydrogenation reaction through raney nickel at the temperature of 170-200 °C, and 2-ethyl-4-methylimidazole is obtained.

Flammability and Explosibility

Non flammable

Synthesis

Dehydrogenation reaction: 550 g of 2-ethyl-4-methylimidazole dihydrochloride was placed in a three-necked flask fitted with an electric stirring device. Preparation of Ruanne nickel catalyst: 22 g of Ruanne nickel was added to 60 mL of 20 wt% potassium hydroxide aqueous solution and stirred for 15 min, followed by washing with pure water and ethanol. The prepared nickel ruanne catalyst was added to the reaction system. The reaction system was heated in an oil bath, the temperature was controlled to 190°C, and the reaction was continuously stirred for 3.5 hours. Upon completion of the reaction, the reaction solution was left to clarify, and the upper layer of clarified liquid was separated and removed. The residue was diluted with a small amount of toluene and filtered to remove the Nguyenay Ni catalyst. The filtrates were combined and vacuum distilled. Fractions with boiling points of 150-160°C/10 mmHg were collected to give 488 g of 2-ethyl-4-methylimidazole in 90.4% yield. The product was analyzed by gas chromatography and the purity was greater than 97%.

References

[1] Patent: CN105367499, 2016, A. Location in patent: Paragraph 0019; 0029; 0031; 0032; 0033

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