Formaldehyde → Methyl diacetate

HRID 1248285Notes

Reaction equation

HRID 1248285 reaction equation
S(=O)(=O)(O)O.C=O.[C:8]([O-:11])(=[O:10])[CH3:9].[Na+].[C:13]([O:16][C:17](=O)C)(=[O:15])[CH3:14]>>[C:8]([O:11][CH2:17][O:16][C:13](=[O:15])[CH3:14])(=[O:10])[CH3:9]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 517045Sodium Acetate2×

Product 1

HCID 12345Methyl diacetateYield 2,856.3%

Conditions

Temperature
150 °C

Procedure

5 g of concentrated sulphuric acid are added dropwise to a suspension of 300 g of paraformaldehyde in 1,020 g of acetic anhydride in the course of 5 minutes, during which the temperature rises from room temperature to about 100° C. When the addition had ended, the mixture is heated to 150° C. and is stirred at this temperature for 3 hours. It is then cooled to room temperature, 25 g of sodium acetate are added and the volatile constituents are distilled off in vacuo. About 1,300 g of distillate are thereby obtained, and are then fractionated, with addition of 10 g of sodium acetate, over a 50 cm packed column. 1,150 g (87.1% of theory) of methylene diacetate of boiling point 96° to 99° C. under 90 mbar are thereby obtained.

Workup

  1. customrises from room temperature to about 100° C
  2. additionWhen the addition
  3. temperatureIt is then cooled to room temperature
  4. distillationthe volatile constituents are distilled off in vacuo
  5. customAbout 1,300 g of distillate are thereby obtained

Sources & evidence

ORD record
ord-cc5a0d57e3a849b98f5411c198b5ece5
Source dataset
uspto-grants-1985_06
Patent number
US04523023

Reaction notes

Loading…