Maleic Anhydride → (2-Methyl-2-propenyl)succinic Anhydride

HRID 2290701Notes

Reaction equation

HRID 2290701 reaction equation
[CH3:1][CH2:2][CH:3]=[CH2:4].[CH3:5]/C=C/C.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH:11]=C1>CCCCCCC>[CH3:4][C:3]([CH2:2][CH:1]1[C:9](=[O:15])[O:14][C:12](=[O:13])[CH2:11]1)=[CH2:5]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 6435908Butene, all isomers

Product 1

HCID 225375(2-Methyl-2-propenyl)succinic Anhydride

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 92.0 g (0.1 mole) of polyisobutene (Indopol H-100 ac. m. wt. 920) and 19.6 g. (0.2 mole) of maleic anhydride is heated at 205°-210° C. for 24 hours. During the first 2 hours of heating, the temperature remains at about 205° C., thereafter the heating range is 205°-210° C. The reaction mixture is allowed to cool to about 80° C. before the addition of 150 ml. of heptane and, after stirring well, is filtered. The filtrate is stripped at about 55° C. and 10 mm. pressure and finally at 150°-170° C. for about one hour to remove any trace of unreacted maleic anhydride. Weight of the dark, reddish, viscous reaction product is 93.6 g. In addition, 11.2 g. of unreacted maleic anhydride is recovered.

Workup

  1. temperatureDuring the first 2 hours of heating
  2. customremains at about 205° C.
  3. customis 205°-210° C
  4. filtrationis filtered
  5. customis stripped at about 55° C.
  6. custompressure and finally at 150°-170° C. for about one hour to remove any trace of unreacted maleic anhydride
  7. customof unreacted maleic anhydride is recovered

Sources & evidence

ORD record
ord-12e8b0048c0d4180b31414c08e7c8e7c
Source dataset
uspto-grants-1986_10
Patent number
US04618438

Reaction notes

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