Water → HCID 23156002, compound

HRID 1515385Notes

Reaction equation

HRID 1515385 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[OH-:9].[Na+].[C:11](Cl)(=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17].[OH2:21]>CC(CC(C)C)=O>[C:11]([O:19][C:1]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:21])[CH:3]=1)(=[O:9])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 5054Resorcinol2×HCID 14798Sodium HydroxideHCID 61034Adipoyl chloride

Product 1

HCID 23156002HCID 23156002, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent2×

Conditions

Temperature
10 °C

Procedure

110.2 g (1.0 mol) of resorcin (hereinafter abbreviated as RS) is dissolved in 110 g of methylisobutyl ketone (hereinafter abbreviated as MIBK) and partially neutralized by adding 26.7 g (0.204 mol) of an aqueous solution of 30.6 weight % of NaOH. Thereafter, the resulting mixture is cooled to 10° C. and added dropwise with 18.3 g (0.10 mol) of adipoyl chloride (hereinafter abbreviated as ADC) over 1 hour while maintaining at 10-15° C. to conduct esterification reaction, which is matured at the same temperature for 1 hour. b Thereafter, azeotropic dehydration is carried out under a reduced pressure (around 40 torr) while raising the temperature. The azeotropic dehydration is stopped at a time that an inner temperature comes to 65° C. after about 3 hours. The water content in the system is 0.3 weight %. Then, MIBK is distilled out under a reduced pressure (30 torr) while raising the temperature. The removal of MIBK is ended at a tome that the inner temperature comes to 120° C. after about 2 hours. In this case, the concentration of MIBK in the system is 5 weight %. After the oligomer decomposition is conducted by maturing at the same temperature for 2 hours, the reaction mixture is discharged into 540 g of water cooled to 5° C. over 30 minutes to separate out crystal. The crystal is filtered by filtration with a Buchner flask under a reduced pressure, washed with 540 g of water and dried under a reduced pressure at 60° C. for 15 hours to obtain 29.8 g of white-light yellowish powder (yield (crude) 90.3%/ADC). As an analytical result through HPLC, bis(3-hydroxyphenyl) adipate is 89/0 weight %, and an oligomer (dimer) is 7.4 weight %, and the starting resorcin is 3.1 weight %. The results are shown in Table 1.

Workup

  1. customover 1 hour
  2. temperaturewhile maintaining at 10-15° C.
  3. customesterification reaction, which
  4. temperaturewhile raising the temperature
  5. waitcomes to 65° C. after about 3 hours
  6. distillationThen, MIBK is distilled out under a reduced pressure (30 torr)
  7. temperaturewhile raising the temperature
  8. customThe removal of MIBK
  9. waitcomes to 120° C. after about 2 hours
  10. waitby maturing at the same temperature for 2 hours
  11. temperaturecooled to 5° C. over 30 minutes
  12. customto separate out crystal
  13. filtrationThe crystal is filtered by filtration with a Buchner flask under a reduced pressure
  14. washwashed with 540 g of water
  15. customdried under a reduced pressure at 60° C. for 15 hours
  16. customto obtain
  17. custom29.8 g of white-light yellowish powder (yield (crude) 90.3%/ADC)

Sources & evidence

ORD record
ord-7857dcb7462b4f34a058644d86fbcc60
Source dataset
uspto-grants-2012_07
Patent number
US08222446B2

Reaction notes

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