Hydrogen Peroxide → HCID 131730705, compound

HRID 448531Notes

Reaction equation

HRID 448531 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([C:16]1[N:21]=[CH:20][N:19]=[C:18]([N:22]([CH:40]2[CH2:45][C:44]([CH3:47])([CH3:46])[NH:43][C:42]([CH3:49])([CH3:48])[CH2:41]2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][CH:30]2[CH2:35][C:34]([CH3:37])([CH3:36])[NH:33][C:32]([CH3:39])([CH3:38])[CH2:31]2)[N:17]=1)[CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[NH:9][C:8]([CH3:15])([CH3:14])[CH2:7]1.OO.[OH2:52].O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)(C)C>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([C:16]1[N:21]=[CH:20][N:19]=[C:18]([N:22]([CH:40]2[CH2:45][C:44]([CH3:47])([CH3:46])[NH:43][C:42]([CH3:48])([CH3:49])[CH2:41]2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][CH:30]2[CH2:31][C:32]([CH3:39])([CH3:38])[NH:33][C:34]([CH3:37])([CH3:36])[CH2:35]2)[N:17]=1)[CH:6]1[CH2:11][C:10]([CH3:12])([CH3:13])[NH:9][C:8]([CH3:14])([CH3:15])[CH2:7]1.[NH:5]=[O:52]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 151402Sodium Carbonate DecahydrateHCID 69485870HCID 69485870, compound

Product 1

HCID 131730705HCID 131730705, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

100 g Chimassorb 2020® (commercial product of Ciba Specialty Chemicals Inc.) in t-butanol is reacted with 120 g 50% hydrogen peroxide in the presence of 3 g sodium carbonate decahydrate to afford the Chimassorb 2020-nitroxyl after approximately 7-9 hrs. of reaction at 75° C. The batch is treated with sodium sulfite solution to destroy unreacted peroxides and then the aqueous layer is split off. The batch pH is brought to 7 with a trace of glacial acetic acid. Additional 140 g t-butanol is added, followed by 100 g butyraldehyde and 0.2 g Cu(I)Cl. Hydrogen peroxide (120 g) is dosed in while maintaining the reaction temperature at 35° C. The batch is on hold at 35° C. until the reaction is complete. A combination of sodium sulfite and sodium hydroxide solution is added. t-Butanol/water is stripped off under partial vacuum (15-20 mm Hg.) and the t-butanol is replaced by hexane. After 30 min. of stirring at 60° C., the aqueous layer is split. The batch pH is adjusted to 7 with a small quantity of acid. An EDTA wash is performed and the product is isolated with hot water stripping and dried in an oven at 80° C. to constant weight. Yield: 117 g; yellow powder.

Sources & evidence

ORD record
ord-15e66877b2c7448690a1f0e8445dd877
Source dataset
uspto-grants-2013_07
Patent number
US08481726B2

Reaction notes

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