Toluene → Silver behenate

HRID 544704Notes

Reaction equation

HRID 544704 reaction equation
[C:1]([OH:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C1(C)C=CC=CC=1.[N+]([O-])([O-])=O.[Ag+:36]>O>[C:1]([O-:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Ag+:36]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8215Docosanoic AcidHCID 24470Silver Nitrate2×

Product 1

HCID 164971Silver behenate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 54.4 g of behenic acid dissolved into 1200 ml of toluene were added 2400 ml of water, and the mixture liquid was homogenized by a high-speed homogenizer. To this solution, with stirring, were added dropwise spending about 30 minutes 400 ml of an aqueous ammoniacal silver nitrate solution containing 27.7 g of silver nitrate, with keeping the temperature of the reaction liquid at 60° C. The stirring was further continued for another 30 minutes. The resulting crystals were filtrated, washed with water, washed with methanol, and then dried under reduced pressure, whereby 65.0 g of silver behenate were obtained.

Workup

  1. stirringTo this solution, with stirring
  2. additionwere added dropwise
  3. customthe temperature of the reaction liquid at 60° C
  4. waitThe stirring was further continued for another 30 minutes
  5. filtrationThe resulting crystals were filtrated
  6. washwashed with water
  7. washwashed with methanol
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-55e4ff6c138240ee912d987f284ea01a
Source dataset
uspto-grants-1984_05
Patent number
US04451561

Reaction notes

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