Oxygen → Diisobutyl Succinate

HRID 224950Notes

Reaction equation

HRID 224950 reaction equation
[Cl-].[Li+].C=C.[C]=[O:6].O=O.N([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=O.[C:16]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])(=[O:28])[CH2:17][CH2:18][CH2:19]CC(OCC(C)C)=O>C(O)C(C)C>[C:16]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])(=[O:28])[CH2:17][CH2:18][C:19]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:6]

Participants

8

Reactant 6

HCID 977OxygenHCID 6325EthyleneHCID 8831Diisobutyl AdipateHCID 10958Isobutyl nitriteHCID 433294Lithium ChlorideHCID 178418416HCID 178418416, compound

Product 1

HCID 70214Diisobutyl Succinate

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

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, 1 g. of palladium-on-activated-carbon (2 wt.%Pd) and 4 mg. of lithium chloride ##EQU2## After sealing and heating the reaction system to 105° C., the reaction was carried out at the same temperature for one hour, passing a gas mixture consisting of 78 vol.% of ethylene, 18 vol.% of carbon monoxide and 4 vol.% of oxygen; maintaining the total pressure at 30 atm.; and supplying isobutyl nitrite continuously at a rate of 39 mmol./hr. After completion of the reaction, the reaction mixture was analyzed quantitatively by gas chromatography. As the result, it was revealed that 20.4 mmol. of diisobutyl succinate was produced and only 1.1 mmol. of diisobutyl oxalate was produced as by-product.

Workup

  1. customequipped with a rotary stirrer
  2. additionwas charged with 50 ml
  3. temperaturemaintaining the total pressure at 30 atm.
  4. customAfter completion of the reaction

Sources & evidence

ORD record
ord-b94e9e7dd95b4c00b8e55d91d3c57e6e
Source dataset
uspto-grants-1980_11
Patent number
US04234740

Reaction notes

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