1-Butanol → HCID 68486048, compound

HRID 2247082Notes

Reaction equation

HRID 2247082 reaction equation
OS(O)(=O)=O.O=S(=O)=O.[C:10]([OH:21])(=[O:20])[C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.O1CC[CH2:25]OO1.[CH2:28](O)[CH2:29][CH2:30][CH3:31]>>[CH2:28]([O:16][C:15]([C:14]1[CH:18]=[C:19]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:21])[O:20][CH2:25]2)=[O:17])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 7489Terephthalic AcidHCID 24681Fuming sulfuric acidHCID 19593658CID 19593658

Product 1

HCID 68486048HCID 68486048, compound

Conditions

Temperature
60 °C

Procedure

Oleum (25% SO3, 95 ml) is charged into a reactor (350 ml). Under stirring terephthalic acid (19.0 g; 0.11 mol) is added to the reactor and the mixture is heated to 60° C. After stirring for additional 30 min terephthalic acid (31.0 g; 0.19 mol) is added and the mixture is heated to 100° C. for 1 hour. The mixture is cooled to 25-30° C., trioxane (12.0 g; 0.13 mol) is added in portions and the reaction mixture is heated slowly to 130-135° C. and agitated at this temperature for 1½ hours and for 4 hours at 155° C. The reaction mixture is cooled to 40° C. and added to a reactor containing butanol (150 ml) and heptanes (150 ml) witch has been heated to 95-100° C. The formed precipitates were diluted with butanol (85 ml) and stirring overnight. The precipitate is filtered off and dried.

Workup

  1. additionUnder stirring terephthalic acid (19.0 g; 0.11 mol) is added to the reactor
  2. additionis added
  3. temperaturethe mixture is heated to 100° C. for 1 hour
  4. temperatureThe mixture is cooled to 25-30° C.
  5. temperaturethe reaction mixture is heated slowly to 130-135° C.
  6. temperatureThe reaction mixture is cooled to 40° C.
  7. additionadded to a reactor
  8. temperaturehas been heated to 95-100° C
  9. customThe formed precipitates
  10. additionwere diluted with butanol (85 ml)
  11. stirringstirring overnight
  12. filtrationThe precipitate is filtered off
  13. customdried

Sources & evidence

ORD record
ord-18997bf42da54f6181c2952a9a40e6eb
Source dataset
uspto-grants-2010_03
Patent number
US07687645B2

Reaction notes

Loading…