Hydroquinone → 2,5-Bis(1,1,3,3-tetramethylbutyl)hydroquinone

HRID 1383886Notes

Reaction equation

HRID 1383886 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C=CC(O)=CC=1)O.[CH3:20][C:21]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH2:22].S(=O)(=O)(O)O.[CH3:33][C:34]([C:41]1[CH:47]=[C:46]([OH:48])[CH:45]=[CH:44][C:42]=1[OH:43])([CH3:40])[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37]>O>[CH3:22][C:21]([C:45]1[CH:44]=[C:42]([OH:43])[C:41]([C:34]([CH3:40])([CH3:33])[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:47][C:46]=1[OH:48])([CH3:20])[CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 5

HCID 785Hydroquinone2×HCID 1118Sulfuric Acid2×HCID 6101p-Toluenesulfonic acid2×HCID 78682,4,4-Trimethyl-1-pentene2×HCID 697491,4-Benzenediol, 2-(1,1,3,3-tetramethylbutyl)-

Product 1

HCID 701802,5-Bis(1,1,3,3-tetramethylbutyl)hydroquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
58 °C

Procedure

To a 500 mL, 3-neck, round-bottom flask equipped with a stirrer, thermocouple and nitrogen are added 67 weight percent p-toluenesulfonic acid (PTSA) in water (33.5 g), hydroquinone (20.0 g, 0.18 moles), diisobutylene (101.8 g, 0.91 moles) and 95% aqueous sulfuric acid (11.2 g, 0.112 moles). This mixture is heated to 58° C. under a nitrogen blanket with stirring. After 14 hours reaction time at 58° C., diisobutylene (50 g) is added and the lower aqueous phase (containing PTSA, sulfuric acid, hydroquinone, mono-(1,1,3,3-tetramethylbutyl)hydroquinone and small amounts of other polar side products) is transferred to another reactor. The diisobutylene phase is washed with 150 g water two times at 50° C. and once at 85°. The remaining clear organic phase at 85° C. is cooled to 70° C. and eventually to 0-10° C. and the 2,5-bis(1,1,3,3-tetramethylbutyl)hydroquinone product which crystallizes is collected by filtration. The product is washed with 60 g cold diisobutylene and dried at room temperature overnight. The 2,5-bis(1,1,3,3-tetramethylbutyl)hydroquinone product is obtained in a yield of 73% product and a purity greater than 98.5%.

Workup

  1. customTo a 500 mL, 3-neck, round-bottom flask equipped with a stirrer
  2. customAfter 14 hours reaction time at 58° C.
  3. customis transferred to another reactor
  4. washThe diisobutylene phase is washed with 150 g water two times at 50° C. and once at 85°
  5. temperatureThe remaining clear organic phase at 85° C. is cooled to 70° C. and eventually to 0-10° C.
  6. customthe 2,5-bis(1,1,3,3-tetramethylbutyl)hydroquinone product which crystallizes
  7. filtrationis collected by filtration
  8. washThe product is washed with 60 g cold diisobutylene
  9. customdried at room temperature overnight

Sources & evidence

ORD record
ord-181b4059eef740f29e75c52cd4884074
Source dataset
uspto-grants-2001_07
Patent number
US06255538B1

Reaction notes

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