Tetramethylol acetylenediurea Chemical Properties

Melting point:

137-138 °C

Boiling point:

624.2±55.0 °C(Predicted)

Density 

1.697±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

13.90±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C8H14N4O6/c13-1-9-5-6(11(3-15)7(9)17)12(4-16)8(18)10(5)2-14/h5-6,13-16H,1-4H2

InChIKey

UUGLSEIATNSHRI-UHFFFAOYSA-N

SMILES

C(N1C(N(C2N(C(N(C21)CO)=O)CO)CO)=O)O

EPA Substance Registry System

Imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)- (5395-50-6)

Tetramethylol acetylenediurea Usage And Synthesis

Uses

Crosslinker, Fungicide, Concrete additive

Uses

Tetramethylol acetylene diurea is a formaldehyde type of textile-finish resin.

Uses

Tetramethylol Acetylenediurea is a useful additive for forming etching patterns in semiconductor manufacturing.

Flammability and Explosibility

Not classified

Synthesis

In a suitable reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser, 688 parts (10 mol) of a 44% aqueous formaldehyde solution were added and the pH was adjusted to 8.7 with 22 parts of 0.5 N NaOH solution.The temperature of the reaction system was maintained at 40 °C to which 284 parts (2 mol) of glyburide were subsequently added. During the reaction, the temperature was gradually increased to 55 °C, at which time most of the glyburide was dissolved. After about 15 minutes, the pH of the reaction system was adjusted to 8.0 with 5 parts of 0.5N NaOH solution to obtain a clarified light yellow solution. This solution was subjected to reduced pressure distillation at 50°C to remove the water until about 640 parts remained in the reaction vessel. The concentrated syrupy product was poured into 800 parts of methanol and a white crystalline precipitate was precipitated. After filtration and drying, 483 parts (92% yield) of 1,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione were obtained with a melting point of 132°C~136°C.

References

[1] Patent: WO2014/166347, 2014, A1. Location in patent: Page/Page column 14
[2] Patent: WO2015/143974, 2015, A1. Location in patent: Page/Page column 15; 16
[3] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 3, p. 365 - 376
[4] Russian Journal of Applied Chemistry, 2016, vol. 89, # 1, p. 132 - 139
[5] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2016, vol. 89, # 1, p. 103 - 111,9

Tetramethylol acetylenediurea(5395-50-6)Related Product Information

• TETRAPHENYLOLETHANE GLYCIDYL ETHER
• (Hydroxymethyl)urea
• Urea formaldehyde
• 2-Hydroxyethyl methacrylate
• Trimethylolpropane
• methylol cellulose
• Imidazole
• Tetrakis(hydroxymethyl)phosphonium sulfate
• Tris(hydroxymethyl)aminomethane
• Glycoluril
• 1-METHYL-2-IMIDAZOLIDINONE
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• Dimethylolurea
• 1,3-Dimethyl-2-imidazolidinone
• 1,3,4,6-Tetrakis(methoxymethyl)glycoluril
• DIMETHYLOL ETHYLENE UREA
• 1,3,4,6-TETRAKIS(BUTOXYMETHYL)GLYCOLURIL, TECH.
• N-(2-DIMETHYLAMINOETHYL)-N-METHYLFORMAM&