N-Cyclohexylmaleimide

N-Cyclohexylmaleimide Property

Melting point:

89-91 °C (lit.)

Boiling point:

132 °C / 17mmHg

Density 

1.226±0.06 g/cm3(Predicted)

vapor pressure 

80Pa at 25℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Insoluble in water

form 

powder to lump

pka

-2.26±0.20(Predicted)

color 

White to Almost white

Water Solubility 

260mg/L at 25℃

InChI

InChI=1S/C10H13NO2/c12-9-6-7-10(13)11(9)8-4-2-1-3-5-8/h6-8H,1-5H2

InChIKey

BQTPKSBXMONSJI-UHFFFAOYSA-N

SMILES

N1(C2CCCCC2)C(=O)C=CC1=O

LogP

2.57 at 23℃

CAS DataBase Reference

1631-25-0(CAS DataBase Reference)

EPA Substance Registry System

1H-Pyrrole-2,5-dione, 1-cyclohexyl- (1631-25-0)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29251900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

N-Cyclohexylmaleimide Chemical Properties,Usage,Production

Uses

N-Cyclohexylmaleimide (CHMI, NCMI) may be used for the preparation of hyperbranched copolymers of p-(chloromethyl)styrene (CMS) and NCMI, via atom transfer radical copolymerization reaction.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1607, 1990 DOI: 10.1080/00397919008053079

General Description

N-Cyclohexylmaleimide (CHMI, NCMI) is a cyclic imide. Diels-Alder reactions of 9-hydroxymethylanthracene with CHMI catalyzed by hydrophobic nanospace confined within the self-assembled Pd₆ open cage bearing triimidazole walls have been reported. It undergoes Diels-Alder reactions with various aromatic hydrocarbons promoted by self-assembled coordination cage. This cage acts as nanometer-sized molecular flask and hence promotes this reaction. CHMI is reported to undergo radical polymerization readily under various polymerization conditions to afford poly(CHMI), having excellent thermal stability.

Flammability and Explosibility

Not classified

Synthesis

1. In a 100 L reactor equipped with a thermometer, water separator, cooler and stirrer, 40 kg of xylene was added as solvent. Subsequently, 2 kg of silica gel as carrier, 2 kg (17.3 mol) o-phosphoric acid, 30 g (0.19 mol) of zinc acetate and 30 g (0.14 mol) of 2,4-dimethyl-6-tert-butylphenol were added sequentially. 200 g (1.96 mol) of triethylamine was added to neutralize the reaction system, followed by the slow addition of 4 kg (43.0 mol) of cyclohexylamine over 5 min to form the amine salt. 2. 4.4kg of maleic anhydride was added to the reactor over 5 minutes. The reaction temperature was maintained at 140°C and the resulting water was removed by azeotropic distillation along with xylene through a water separator. The reaction was maintained at this temperature for 3 hours. 3. After 3 hours of reaction, an additional 200g of maleic anhydride was added and the reaction was continued for another 3 hours. Upon completion of the reaction, the reaction mixture was cooled to 30°C and the catalyst layer was removed by layer separation. 4. The xylene solution layer was transferred to a neutralization tank, 500 g of 5% aqueous sodium carbonate solution was added, stirred for 20 minutes and then allowed to stand for 20 minutes to stratify the solution. Separate and discard the aqueous layer. 5. Add 500g of water to the organic layer, stir for 20 minutes and leave for 20 minutes, separate again and discard the aqueous layer. 6. The purified organic layer was transferred to a concentration tank and gradually heated under reduced pressure to 50°C, 100°C and finally distilled at 20°C to remove xylene. After complete evaporation of the solvent, 7.1 kg of light white solid product was obtained. 7. The purity of the product N-cyclohexylmaleimide was 98% by liquid chromatography analysis, based on a 97% yield of cyclohexylamine.

References

[1] Patent: EP2311804, 2011, A2. Location in patent: Page/Page column 7-8
[2] Patent: US2011/124882, 2011, A1. Location in patent: Page/Page column 5
[3] Patent: JP6273389, 2018, B1. Location in patent: Paragraph 0044-0054
[4] Patent: JP6336192, 2018, B1. Location in patent: Paragraph 0054; 0055; 0057; 0059; 0060; 0061-0066
[5] Molecules, 2018, vol. 23, # 11,