Propylene Oxide → 2-hydroxymethylethyl isopropyl maleate

HRID 976611Notes

Reaction equation

HRID 976611 reaction equation
[C:1]([O:8][CH:9]([CH3:11])[CH3:10])(=[O:7])/[CH:2]=[CH:3]\[C:4]([O-:6])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:31]1[O:34][CH:32]1[CH3:33]>>[C:1]([O:8][CH:9]([CH3:11])[CH3:10])(=[O:7])/[CH:2]=[CH:3]\[C:4]([O:6][CH2:33][CH2:32][CH2:31][OH:34])=[O:5]

Participants

4

Reactant 3

HCID 6378Propylene Oxide2×HCID 11776TriphenylphosphineHCID 86752558HCID 86752558, compound

Product 1

HCID 64329732-hydroxymethylethyl isopropyl maleate

Conditions

Temperature
85 °C

Procedure

2100 grams of 2-propyl maleate (Example 9), 8.12 grams of triphenylphosphine, and 8.12 grams of tri-2-ethylhexylphosphite were charged to a 4 liter stirred stainless steel pressure autoclave. The reactor was twice pressurized with nitrogen then depressurized, finally leaving 0.36 kPa nitrogen. The reactor contents were heated to 85° C., and 829.74 grams of propylene oxide were added over 3 hours. Then 270 grams of propylene oxide were added. After 3 hours, the pressure was lowered to remove residual propylene oxide. The product was a liquid containing less than 100 parts per million propylene oxide, having a viscosity of 75.7 centipoise at 25° C. and an acid number of 0.61 milligrams KOH/gram of solution.

Workup

  1. customfinally leaving 0.36 kPa nitrogen
  2. customto remove residual propylene oxide
  3. additioncontaining less than 100 parts per million propylene oxide
  4. customat 25° C.

Sources & evidence

ORD record
ord-6dc11cc9a282437f927df395105a8ed7
Source dataset
uspto-grants-1997_03
Patent number
US05612416

Reaction notes

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