N-METHYLACRYLAMIDE Chemical Properties

Melting point:

102-106 °C

Boiling point:

156.6°C (rough estimate)

Density 

1.0408 (rough estimate)

refractive index 

1.4340 (estimate)

storage temp. 

2-8°C

pka

15.12±0.46(Predicted)

Appearance

Colorless to light yellow Liquid

CAS DataBase Reference

1187-59-3

EPA Substance Registry System

2-Propenamide, N-methyl- (1187-59-3)

Safety Information

Risk Statements 

20/21/22-36/37/38

Safety Statements 

23-26-36/37/39

RIDADR 

2810

HazardClass 

6.1(b)

PackingGroup 

III

N-METHYLACRYLAMIDE Usage And Synthesis

Safety Profile

Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

(C) To a 1000 mL four-necked flask equipped with a stirrer, thermometer, and gas introduction tube was added 400 g of MeO-DEAA obtained in step (b), followed by 6.8 g of potassium hydroxide and 0.4 g of TDA.A distillation column equipped with a packer, condenser, and distillation receiver was mounted on the flask, and a trace amount of nitrogen was passed through to act as a carrier gas. The reaction temperature was adjusted to 180 °C while stirring the reaction mixture. The system vacuum was adjusted to 60 kPa and the pyrolysis reaction was carried out for 12 hours. 307 g of crude N,N-diethylacrylamide (DEAA) (purity = 93%, yield = 92%) was obtained by collection through a water condenser. The crude DEAA was transferred to a distillation purification unit equipped with a 20 cm McMahon packing (6 mm particle size) filled column and purified by reduced pressure distillation (60 °C/0.13 kPa). The final 258 g of high purity DEAA (99.8% purity) was obtained as a colorless liquid. Examples 2-18: On the basis of Example 1, the raw materials, catalysts, solvents, polymerization blockers and reaction conditions were varied as shown in Table 1 and synthesized according to the same steps as in Example 1 to obtain the corresponding N-methyl-2-acrylamide. The results are summarized in Table 2.

References

[1] Patent: JP2015/101554, 2015, A. Location in patent: Paragraph 0057; 0060

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