Methanol → Levulinic Acid

HRID 1528005

Reaction equation

HRID 1528005 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])O)[OH:6])O.[CH3:13][OH:14].S(=O)(=O)(O)[OH:16]>O>[OH:12][CH2:11][C:9]1[O:10][C:3]([CH:2]=[O:1])=[CH:5][CH:7]=1.[CH3:13][O:14][CH2:11][C:9]1[O:10][C:3]([CH:2]=[O:1])=[CH:5][CH:7]=1.[CH3:13][O:14][C:11](=[O:12])[CH2:9][CH2:7][C:5]([CH3:3])=[O:6].[C:11]([OH:12])(=[O:16])[CH2:9][CH2:7][C:5]([CH3:3])=[O:6]

Participants

8

Reactant 3

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal4×

Product 4

HCID 11579Levulinic AcidHCID 69354Methyl levulinateHCID 747115-(Methoxymethyl)-2-furaldehydeHCID 2373325-(Hydroxymethyl)furfural

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

An amount of 100 g glucose was added to 800 mL of a mixture of methanol and water (5 vol % water) that contained 55 mmol (5.4 gr) sulphuric acid. The admixture obtained was stirred at 60° C. until all solids were dissolved in about 4 hours. After the dissolution, the volume of the solution is adjusted to 1 L by adding a mixture of methanol and water (5 vol % water). The solution obtained which contains a mixture of glucose and glucosides was passed through a plug flow reactor that was heated at different temperatures, varying from 200 to 220° C. The residence time in the heated zone of the reactor was also varied and was set at 2, 4 or 8 minutes. The pressure in the reactor was maintained at 65 bar. After having obtained a steady state condition in the reactor the product stream was analysed. The analysis determined the conversion (1 minus the number of moles of glucose and glucosides in the product stream divided by the number of moles of glucose in the starting material, expressed in percent), and the yields for 5-hydroxymethylfurfural (“HMF”), 5-methoxymethylfurfural (“MMF”), methyllevulinate (“Me-Lev”) and levulinic acid (“LA”). The yield is expressed in percent and has been calculated as the number of moles of the compound in question divided by the initial moles of glucose times 100. The results are shown in Table 5.

Workup

  1. customThe admixture obtained
  2. dissolutionwere dissolved in about 4 hours
  3. dissolutionAfter the dissolution
  4. additionby adding
  5. customThe solution obtained which
  6. customwas passed through a plug flow reactor
  7. temperaturethat was heated at different temperatures
  8. customvarying from 200 to 220° C
  9. customwas set at 2, 4 or 8 minutes
  10. temperatureThe pressure in the reactor was maintained at 65 bar
  11. customAfter having obtained a steady state condition in the reactor the product stream

Sources & evidence

ORD record
ord-bb1915d607024c829555cb4620772476
Source dataset
uspto-grants-2015_07
Patent number
US09090581B2

Linked notes

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