Glutaric anhydride → Pentaerythritol trinitrate glutarate

HRID 2380393Notes

Reaction equation

HRID 2380393 reaction equation
[N+:1]([O:4][CH2:5][C:6]([CH2:17][OH:18])([CH2:12][O:13][N+]([O-])=O)[CH2:7][O:8][N+]([O-])=O)([O-:3])=[O:2].[C:19]1(=[O:26])[O:25][C:23](=[O:24])[CH2:22][CH2:21][CH2:20]1>CN(C)C1C=CN=CC=1.CCOCC>[C:19]([OH:25])(=[O:26])[CH2:20][CH2:21][CH2:22][C:23]([OH:2])=[O:24].[N+:1]([O-:4])([OH:3])=[O:2].[N+:1]([O-:4])([OH:3])=[O:2].[N+:1]([O-:4])([OH:3])=[O:2].[OH:4][CH2:5][C:6]([CH2:17][OH:18])([CH2:12][OH:13])[CH2:7][OH:8]

Participants

5

Reactant 2

HCID 7940Glutaric anhydrideHCID 15353Pentaerythritol, trinitrate

Product 1

HCID 86748279Pentaerythritol trinitrate glutarateYield 145.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

Pentaerythritol trinitrate (0.8 gram, 0.003 mol) was combined with 0.4 gram (0.03 mol) of glutaric anhydride and 50 mg of 4-dimethylamino pyridine in 25 ml of ether. The mixture was stirred at boiling for 12 hours and concentrated under vacuum, then the oily residue was partitioned between ether and saturated NaHCO3. The aqueous base layer was removed and acidified with 1N HCl to approximately pH 6. The solution was cooled in ice and after 15 minutes a white precipitate was collected, washed with water and air dried, yielding 0.5 gram of pentaerythritol trinitrate glutarate in the form of a white powder.

Workup

  1. concentrationconcentrated under vacuum
  2. customthe oily residue was partitioned between ether and saturated NaHCO3
  3. customThe aqueous base layer was removed
  4. temperatureThe solution was cooled in ice and after 15 minutes a white precipitate
  5. customwas collected
  6. washwashed with water and air
  7. customdried

Sources & evidence

ORD record
ord-cef31c830bfe4aa68ae78394ae15c614
Source dataset
uspto-grants-1994_11
Patent number
US05367061

Reaction notes

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