Sulfuric Acid → Propanoic acid, 3-(nitrooxy)-2,2-bis[(nitrooxy)methyl]-

HRID 567930Notes

Reaction equation

HRID 567930 reaction equation
[O-][Mn](=O)(=O)=O.[K+].[CH2:7]([OH:24])[C:8]([CH2:19][O:20][N+:21]([O-:23])=[O:22])([CH2:14][O:15][N+:16]([O-:18])=[O:17])[CH2:9][O:10][N+:11]([O-:13])=[O:12].S([O-])(O)=[O:26].OS(O)(=O)=O>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O.C1C=CC=CC=1>[N+:16]([O:15][CH2:14][C:8]([CH2:19][O:20][N+:21]([O-:23])=[O:22])([CH2:9][O:10][N+:11]([O-:13])=[O:12])[C:7]([OH:26])=[O:24])([O-:18])=[O:17]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 15353Pentaerythritol, trinitrateHCID 104748BisulfiteHCID 516875Potassium Permanganate

Product 1

HCID 9882291Propanoic acid, 3-(nitrooxy)-2,2-bis[(nitrooxy)methyl]-Yield 72%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

0.0074 mol of KMnO4 is added in portions, with vigorous stirring, to a solution of 0.0037 mol of pentaerythrityl trinitrate (PETriN), 5.5 ml of benzene, 9 ml of water and 0.15 ml of Aliquat® 336. When the addition has ended, the temperature is kept at 15° C. for 2 hours. Aqueous hydrogensulfite solution is then added, the mixture is acidified with H2SO4 and the benzene layer is separated off. After removal of the solvent, 3-nitryloxy-2,2-bis(nitryloxymethyl)propionic acid (Tri-PA) is obtained as a solid residue, which is recrystallized several times from methylene chloride. Yield: 72%.

Workup

  1. additionWhen the addition
  2. customthe benzene layer is separated off
  3. customAfter removal of the solvent

Sources & evidence

ORD record
ord-d523d9157cc143ec9dc001aaf4db2333
Source dataset
uspto-grants-2001_01
Patent number
US06180664B2

Reaction notes

Loading…