Sulfuric Acid → Pentyl formate

HRID 2225044Notes

Reaction equation

HRID 2225044 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([CH3:6])=[O:5].[CH:9](=O)[C:10]1[O:14][CH:13]=[CH:12][CH:11]=1.S(=O)(=O)(O)O>C(O)=O>[C:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:7])[CH2:2][CH2:3][C:4]([CH3:6])=[O:5].[CH:13]([O:8][CH2:1][CH2:2][CH2:3][CH2:4][CH3:6])=[O:14]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7362FurfuralHCID 11579Levulinic Acid

Product 2

HCID 12529Pentyl formateHCID 88453Pentyl 4-oxovalerate

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The liquid fraction comprises levulinic acid, formic acid, furfural, and sulphuric acid. The liquid fraction is supplied via line 8 to reactive extraction reactor 9. 1-pentanol, which may be fresh pentanol and/or recycled pentanol, is countercurrently supplied to reactor 9 via line 10. In reactive extraction reactor 9, levulinic acid and formic acid react with 1-pentanol to form pentyl levulinate and pentyl formate. The esters formed and furfural will be extracted to the organic, pentanol phase. Thus, an aqueous phase comprising sulphuric acid and an organic phase comprising 1-pentanol, pentyl levulinate, pentyl formate and furfural are formed. The organic, pentanol phase is discharged from reactor 9 via line 11 and may be separated into its individual components in a product separation section (see FIG. 2). The aqueous phase is discharged from reactor 9 via line 12 and for the greater part recycled to acid hydrolysis reaction zone 1 via line 13. Part of the aqueous phase is fed to extraction column 14 via line 15. 1-Pentanol is supplied to extraction column 14 via line 16. In column 14, the remainder of the organic compounds is extracted from the aqueous phase to yield a second aqueous phase that is removed from the process via line 17 and a second organic pentanol phase that is recycled to reactive extraction reactor 9 via line 18.

Workup

  1. extractionextraction reactor 9
  2. customis countercurrently supplied to reactor
  3. customIn reactive extraction reactor 9, levulinic acid and formic acid react with 1-pentanol

Sources & evidence

ORD record
ord-19138de1ac03463fa0a39b7b9fcef6bf
Source dataset
uspto-grants-2008_05
Patent number
US07378549B2

Reaction notes

Loading…