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Phthalic Anhydride → Maleic Anhydride

HRID 441503
Notes
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Reaction equation

HRID 441503 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1(=O)OC(=O)CC1.C1(=O)OC(=O)C=C1C.C1(=O)OC(=O)CC1=C.ClC1C(OC(=O)C=1)=O.CC1CC(=O)OC1=O.C(C1CC(=O)OC1=O)CC.C(C1CC(=O)OC1=O)CCCCC.C1(C2C(OC(=O)C=2)=O)C=CC=CC=1.CC1(C)C(CC2C=CC=CC=2)C(=O)OC1=O.C1(=O)OC(=O)C2=CC=CC=C12.C1(=O)OC(=O)C2CCC=CC12.C1(=O)OC(=O)C2CCCCC12>>[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH:2]=[CH:3]1.[CH:1]1[CH2:8][CH2:4][CH2:3][CH:2]=1.[O:6]1[CH:1]=[CH:2][CH:3]=[CH:4]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

16

Reactant 13

HCID 6811Phthalic AnhydrideHCID 7922Succinic anhydrideHCID 7923Maleic Anhydride2×HCID 12012Citraconic AnhydridesHCID 20051Methylsuccinic anhydrideHCID 66772Chloromaleic anhydrideHCID 75110Itaconic Anhydride
HCID 85689Hexahydrophthalic anhydride
HCID 99174Phenylmaleic anhydride
HCID 5127355Propylsuccinic anhydride
HCID 126561692,5-Furandione, 3-hexyldihydro-
HCID 127266013a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dione
HCID 86734988alpha,alpha-Dimethylbenzylsuccinic anhydride

Product 3

HCID 7923Maleic AnhydrideHCID 8029FuranHCID 8882Cyclopentene

Procedure

Desirable nonplasticizing monoanhydrides include maleic anhydride; succinic anhydride; and the one to six carbon alkyl, the chloro, the phenyl, the benzyl and the mono and dimethylbenzyl derivatives of maleic anhydride such as citraconic anhydride; itaconic anhydride; chloromaleic anhydride; methyl succinic anhydride; propylsuccinic anhydride, hexylsuccinic anhydride; phenylmaleic anhydride; α,α-dimethylbenzylsuccinic anhydride; and the like. Also desirable monoanhydrides include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, and their chloro, methyl and cyano derivatives, and the like, such as methyltrihydrophthalic anhydride; 1,2-dicarboxylic- 4-chlorocyclohexane anhydride; 1,2-dicarboxylic-4-cyanocyclohexane anhydride; and the like. Further desirable monoanhydrides include 1,2-dicarboxylic-cyclopentane; 1,2-dicarboxyliccycloheptane; and the three-ringed anhydrides formed by the Diels-Alder condensation of maleic anhydride with cyclopentene, furan, or their methyl derivatives, such as bicyclo(2.2.1)heptene-2,3-dicarboxylic anhydride (Nadic anhydride); a mixture of methylbicyclo(2.2.1)heptene-2,3-dicarboxylic anhydride isomers (Nadic methyl anhydride); 7-oxabicyclo(2.2.1)heptene-2,3-dicarboxylic anhydride; and the like.

Sources & evidence

ORD record
ord-cde1ca1f3b224c48a26c86540227f85c
Source dataset
uspto-grants-1977_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04041004

Reaction notes

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