Oxygen → Diisobutyl Succinate

HRID 224951Notes

Reaction equation

HRID 224951 reaction equation
C=C.[C]=[O:4].O=O.N([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=O.[C:14]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])(=[O:26])[CH2:15][CH2:16][CH2:17]CC(OCC(C)C)=O>C(O)C(C)C.[Pd](Cl)Cl>[C:14]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])(=[O:26])[CH2:15][CH2:16][C:17]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[O:4]

Participants

8

Reactant 5

HCID 977OxygenHCID 6325EthyleneHCID 8831Diisobutyl Adipate2×HCID 10958Isobutyl nitriteHCID 178418416HCID 178418416, compound

Product 1

HCID 70214Diisobutyl Succinate

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6560IsobutanolSolvent2×

Conditions

Temperature
105 °C

Procedure

An autoclave made of stainless steel, equipped with a rotary stirrer and having a capacity of 300 ml. was charged with 50 ml. of isobutanol, 50 ml. of diisobutyl adipate as a solvent and 0.19 mmol. of palladium chloride. After sealing, 20 atm. of a gas mixture consisting of 78 vol.% of ethylene, 18 vol.% of carbon monoxide and 4 vol.% of oxygen was pressured thereinto. Subsequently, after the contents of the autoclave was heated to 105° C. with stirring, the reaction was carried out for one hour while supplying the above-mentioned gas mixture at a rate of 0.6 l./min. and isobutyl nitrite dissolved in a mixed solvent of isobutanol and diisobutyl adipate (1:1, volume ratio) at a rate of 40 mmol./hr. as the result, it was found that 22.5 mmol. of diisobutyl succinate was produced and 0.54 mmol. of diisobutyl oxalate was produced as by-product.

Workup

  1. customequipped with a rotary stirrer
  2. additionwas charged with 50 ml

Sources & evidence

ORD record
ord-6c1ad24653dc4def8bdbec5258ecfaad
Source dataset
uspto-grants-1980_11
Patent number
US04234740

Reaction notes

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