Formic Acid → Butyl levulinate

HRID 860906

Reaction equation

HRID 860906 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([CH3:6])=[O:5].C(O)=O.S(=O)(=O)(O)O.[CH2:17]=[CH:18][CH2:19][CH3:20]>C(CC(C)(C)C)(C)C>[C:1]([O:8][CH2:17][CH2:18][CH2:19][CH3:20])(=[O:7])[CH2:2][CH2:3][C:4]([CH3:6])=[O:5]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 1118Sulfuric AcidHCID 78441-Butene2×HCID 11579Levulinic Acid

Product 1

HCID 16331Butyl levulinate

Reagents, catalysts & solvents 1

HCID 109072,2,4-TrimethylpentaneSolvent

Conditions

Temperature
100 °C

Procedure

A 5 cc autoclave is charged with 1 cc of iso-octane and 1 cc of an aqueous solution containing 2 mmoles of levulinic acid and 2 mmoles of formic acid. 5 wt. % sulfuric acid is added as a catalyst. The reactor is pressurized to 0.69 MPa with 1-butene and heated to 100° C. for 2 hours while maintaining a constant pressure of 1-butene. After cooling, the organic phase is separated. A mixture of butyl formate and butyl levulinate is formed as product.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase is separated
  3. additionA mixture of butyl formate

Sources & evidence

ORD record
ord-e7650c739dbe45d2bc04ace808cdc09e
Source dataset
uspto-grants-2006_12
Patent number
US07153996B2

Linked notes

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