Melamine → 2-{2-[(4,6-Diamino-1,3,5-triazin-2-yl)amino]ethoxy}ethan-1-ol

HRID 381665Notes

Reaction equation

HRID 381665 reaction equation
[N:1]1[C:8]([NH2:9])=[N:7][C:5]([NH2:6])=[N:4][C:2]=1[NH2:3].[H][H].[CH2:12]([OH:18])[CH2:13][O:14][CH2:15][CH2:16]O>>[NH2:3][C:2]1[N:4]=[C:5]([NH2:6])[N:7]=[C:8]([NH:9][CH2:16][CH2:15][O:14][CH2:13][CH2:12][OH:18])[N:1]=1

Participants

4

Reactant 3

HCID 7955Melamine2×HCID 8117Diethylene GlycolHCID 178418361HCID 178418361, compound

Product 1

HCID 155976522-{2-[(4,6-Diamino-1,3,5-triazin-2-yl)amino]ethoxy}ethan-1-olYield 2%

Procedure

In a stainless steel autoclave of an inner volume of 100 ml, 1.26 g (10 mmol) of melamine, 250 mg of CuO—Cr2O3—NiO—BaO catalyst (T-4364, manufactured by Nissan Girdler Catalyst Co., Ltd.), and 30 ml of diethylene glycol were charged. After the inside of the reaction system was sufficiently substituted with nitrogen gas, 10 kg/cm2 of hydrogen gas was introduced under pressure at normal temperature. Then, the temperature was elevated while stirring, and after the temperature reached 260° C., the reaction was carried out at the same temperature for further 2 hours. After cooling, the reaction mixture was taken out and quantitative analysis of the reaction product was performed under the above analytical conditions. As a result, the reaction conversion rate of the starting material melamine was 11% and it was confirmed that there were produced only about 2% of 2,4-diamino-6-(5-hydroxy-3-oxapentylamino)-1,3,5-triazine together with many byproducts and an obvious decrease in activity as compared with the mixed catalyst systems was confirmed.

Workup

  1. additionwas introduced under pressure at normal temperature
  2. customreached 260° C.
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-cf7e1f4251fa4451b867fb0263e99685
Source dataset
uspto-grants-2001_10
Patent number
US06307046B1

Reaction notes

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