Oxygen → 2,5-Dioctyladipic anhydride

HRID 1266690

Reaction equation

HRID 1266690 reaction equation
C1(=O)OC(=O)CCCC1.[CH2:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].O=O.[CH2:20]([CH:28]1[CH2:35][CH2:34][CH2:33][C:32](=[O:36])[O:31][C:29]1=[O:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C([O-])(=O)C.[Mn+2].C([O-])(=O)C.C(O)(=O)C>[CH2:20]([CH:28]1[CH2:35][CH2:34][CH:33]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:32](=[O:36])[O:31][C:29]1=[O:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 4

HCID 977OxygenHCID 81251-OcteneHCID 567658Adipic anhydrideHCID 120841292-Octyladipic anhydride

Product 1

HCID 865863762,5-Dioctyladipic anhydride

Reagents, catalysts & solvents 2

HCID 12525Manganous AcetateCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 20 mmol of adipic anhydride, 2 mmol of 1-octene, 0.04 mmol of manganese (II) acetate, 0.002 mmol of cobalt (II) 0 acetate and 2 ml of acetic acid was stirred at 90° C. in an atmosphere of a gaseous mixture of nitrogen and oxygen (9:1) (1 atm=0.101 MPa) for 3 hours. The resulting reaction mixture was analyzed to find that 2-octyladipic anhydride and 2,5-dioctyladipic anhydride were produced in yields of 29% and 2%, respectively, with a conversion from 1-octene of 63%.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-1d461ff77aca480ca60a77506d122af6
Source dataset
uspto-grants-2003_04
Patent number
US06548713B2

Linked notes

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