Propylene Glycol → HCID 86751389, compound

HRID 1489303Notes

Reaction equation

HRID 1489303 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1(=[O:18])[O:13][C:11](=[O:12])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[CH2:19]([OH:23])[CH:20]([OH:22])[CH3:21].[OH-].[K+].C1(C)C=CC(S(O)(=O)=[O:33])=CC=1.C=CC1C=CC=CC=1>>[C:1]([OH:6])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:12])=[O:5].[C:11]([OH:12])(=[O:22])/[CH:10]=[CH:9]\[C:8]([OH:13])=[O:18].[CH2:19]([OH:23])[CH:20]([OH:22])[CH3:21].[C:8]([O-:13])(=[O:18])[C:9]1[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:11]([O-:33])=[O:12]

Participants

7

Reactant 6

HCID 1030Propylene Glycol2×HCID 6101p-Toluenesulfonic acidHCID 6811Phthalic AnhydrideHCID 7501StyreneHCID 7923Maleic AnhydrideHCID 14797Potassium Hydroxide3×

Product 1

HCID 86751389HCID 86751389, compoundYield 89%

Conditions

Temperature
70 °C

Procedure

A three-liter reactor equipped as described in Example 2 is charged with a mixture of maleic anhydride (750 g) and phthalic anhydride (250 g), which is melted by heating to 70° C. Propylene glycol (348 g) is added, and the exothermic reaction is maintained at 130° C. or less until the reaction subsides (about 2 h). The acid number of this bis-maleate/phthalate intermediate is 417 mg KOH/g. A 3000 mol. wt. polyoxypropylene triol (1152 g) and p-toluenesulfonic acid (2.5 g) are added, and the mixture is heated at 190° C. until the acid number drops to 123 mg KOH/g. Propylene glycol (237 g) is added, and heating continues until the acid number reaches 42 mg KOH/g. The product is cooled and isolated (2372 g, 89% yield). GPC analysis shows: Mn =1475, Mw=7590. A blend of the resin with 40 wt. % styrene has APHA color =150.

Workup

  1. customA three-liter reactor equipped
  2. customthe exothermic reaction
  3. temperatureis maintained at 130° C. or less until the reaction subsides (about 2 h)
  4. temperaturethe mixture is heated at 190° C. until the acid number
  5. temperatureheating
  6. temperatureThe product is cooled
  7. customisolated (2372 g, 89% yield)

Sources & evidence

ORD record
ord-f96411fccec441f2adb49cd803cf4aa7
Source dataset
uspto-grants-1997_10
Patent number
US05677396

Reaction notes

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