Methanol → 2,5-Tetrahydrofurandimethanol

HRID 1462226

Reaction equation

HRID 1462226 reaction equation
[OH:1][CH2:2][C:3]1[O:4][C:5]([CH2:8][OH:9])=[CH:6][CH:7]=1.CO>O>[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[O:4]1

Participants

4

Conditions

Temperature
30 °C

Procedure

To a 2 gal. stainless steel stirred autoclave was charged 1420.5 g. of 2,5-dihydroxymethylfuran and 113.68 g. of the cationic ruthenium zeolite and 1 gal. of methanol. The system was pressurized with H2 to 3500 psig and heated to 30° C. An exothermic gas uptake was seen and the temperature rose within a minute to 82° C. Cooling water was started to control the exothermic reaction. After 5 hours, gas uptake had essentially ceased and gas chromatographic analysis indicated no starting material was present. Distillation gave 92 percent yield of 2,5-dihydroxymethyl tetrahydrofuran and about 8 percent of a product identified as 5-methyl tetrahydrofuran-2-methanol (hydrogenolysis product).

Workup

  1. customrose within a minute to 82° C
  2. customthe exothermic reaction
  3. distillationDistillation

Sources & evidence

ORD record
ord-74df195c91fc41a986461aa79a0f242f
Source dataset
uspto-grants-1984_07
Patent number
US04459419

Linked notes

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