Maleic Anhydride → Dihydro-3-(1-octadecen-1-yl)-2,5-furandione

HRID 1979782Notes

Reaction equation

HRID 1979782 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:19]1(=[O:25])[O:24][C:22](=[O:23])[CH:21]=[CH:20]1>>[CH:1]([CH:20]1[CH2:21][C:22](=[O:23])[O:24][C:19]1=[O:25])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 7923Maleic AnhydrideHCID 82171-Octadecene

Product 1

HCID 225771Dihydro-3-(1-octadecen-1-yl)-2,5-furandioneYield 53.5%

Conditions

Temperature
200 °C

Procedure

One thousand and eight grams (4.0 moles) of 1-octadecene and 490 grams (5.0 moles) of maleic anhydride were placed in a 2 liter stirred autoclave equipped with a thermocouple. The reaction was carried out by heating the mixture at 200° C. for 4 hours, and the cooled product was transferred to a 2 liter round bottom flask equipped with a magnetic stir bar, a thermometer, and a distilling head mounted on a Vigreux Column. Unreacted starting materials were removed at 200° C. and 10 torr, leaving the product ODSA (750 grams) in the pot. It was typically a tan solid (m.p. 40°-55° C.) with strong adsorption in its IR spectrum at 1860 and 1785 cm-1.

Workup

  1. customequipped with a thermocouple
  2. customthe cooled product was transferred to a 2 liter round bottom flask
  3. customequipped with a magnetic stir bar
  4. customwere removed at 200° C.

Sources & evidence

ORD record
ord-ec85af8affc1426e883a61831fbcbc57
Source dataset
uspto-grants-1984_11
Patent number
US04482655

Reaction notes

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