

Available forms:clear colorless to amber liquid
pd_proNo:171662-f96b8566-76af-425c-8754-2c365ed3e72a
pd_productuse:
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Synthesis Reference(s) |
The Journal of Organic Chemistry, 54, p. 3475, 1989 DOI: 10.1021/jo00275a039Synthesis, p. 209, 1973 |
|
Air & Water Reactions |
Highly flammable. 2,5-Dimethylfuran may be sensitive to exposure to air(not vigorous). Insoluble in water. |
|
Reactivity Profile |
2,5-Dimethylfuran can react vigorously with oxidizing materials. 2,5-Dimethylfuran is also incompatible with strong acids and strong bases. |
|
Fire Hazard |
2,5-Dimethylfuran is flammable. |
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General Description |
2,5-Dimethylfuran (DMF) is a bio-based chemical with significant potential as a biofuel additive, synthesized via the hydrogenation of 5-hydroxymethylfurfural (HMF). It can be efficiently produced using bimetallic or transition metal catalysts, such as Fe-Pd/C or Cu/ZrO2, which offer high selectivity (up to 98.7%) and conversion rates under environmentally friendly conditions. The catalytic processes often leverage metal-support interactions to enhance stability and efficiency, with some systems enabling magnetic separation for easy recovery. DMF production benefits from optimized reaction parameters, including temperature, pressure, and solvent systems, making it a promising renewable fuel candidate. |
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Aroma threshold values |
Medium strength odor, meaty type; recommend smelling in a 10.0% solution or less. |
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Taste threshold values |
Chemical meaty gravy taste at 30 ppm in water. |
InChI:InChI=1/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3
There is an ever increasing need to inno...
-
The high-pressure asymmetric Diels-Alder...
Catalytic hydrogenolysis reaction of 5-h...
Metal-support interfaces play a very imp...
A high-throughput composite catalyst is ...
We have previously shown that 2,5-dimeth...
An efficient catalysis system composed o...
Lignocellulosic biomass is a plentiful a...
New heterogeneous catalysts were obtaine...
Hydrodeoxygenation (HDO) for upgrading b...
The invention provides a magnetic gold-c...
Single-atom site catalysts (SACs) have b...
The invention relates to a method for pr...
5-hydroxymethyl-2-furfuraldehyde
2,5-dimethyltetrahydrofuran
2,5-dimethylfuran
| Conditions | Yield |
|---|---|
|
With
isopropyl alcohol;
In
decane;
at 160 ℃;
for 8h;
under 15001.5 Torr;
Reagent/catalyst;
Temperature;
Solvent;
Pressure;
Autoclave;
Inert atmosphere;
|
84% 8% |
|
With
hydrogen;
In
tetrahydrofuran;
at 220 ℃;
for 2.5h;
under 11251.1 Torr;
Time;
|
67.5% 6.4% |
|
With
rhodium on carbon; hydrogen; 1-butyl-3-methylimidazolium chloride;
In
tetrahydrofuran; water;
at 220 ℃;
for 5h;
under 37503.8 Torr;
Solvent;
Reagent/catalyst;
Autoclave;
|
47% 20% |
|
With
tetrahydro-5-methyl-2-furanmethanol; sulfuric acid; palladium on carbon; acetic acid;
In
tetrahydrofuran;
at 90 ℃;
for 20h;
under 2585.81 Torr;
|
|
|
With
hydrogen;
In
ethanol;
at 220 ℃;
for 6h;
under 37503.8 Torr;
Reagent/catalyst;
Solvent;
Overall yield = 80 %;
Autoclave;
|
|
|
With
Zn-Cu couple; hydrogen;
at 220 ℃;
for 6h;
under 15001.5 Torr;
Temperature;
Overall yield = 97 %Chromat.;
Catalytic behavior;
|
|
|
Multi-step reaction with 2 steps
1: hydrogen / butan-1-ol / 18 h / 109.84 °C / 22502.3 Torr / Autoclave
2: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
With
hydrogen;
In
butan-1-ol;
|
|
|
Multi-step reaction with 2 steps
1: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
2: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
With
hydrogen;
In
butan-1-ol;
|
|
|
Multi-step reaction with 2 steps
1: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
2: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
With
hydrogen;
In
butan-1-ol;
|
|
|
Multi-step reaction with 2 steps
1: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
2: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
With
hydrogen;
In
butan-1-ol;
|
|
|
Multi-step reaction with 2 steps
1: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
2: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
With
hydrogen;
In
butan-1-ol;
|
|
|
Multi-step reaction with 3 steps
1: hydrogen / butan-1-ol / 18 h / 109.84 °C / 22502.3 Torr / Autoclave
2: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
3: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
With
hydrogen;
In
butan-1-ol;
|
|
|
Multi-step reaction with 3 steps
1: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
2: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
3: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
With
hydrogen;
In
butan-1-ol;
|
|
|
Multi-step reaction with 3 steps
1: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
2: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
3: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
With
hydrogen;
In
butan-1-ol;
|
|
|
With
CuZn; hydrogen;
at 220 ℃;
for 18h;
under 15001.5 Torr;
Pressure;
Solvent;
Reagent/catalyst;
Overall yield = 97 %;
Autoclave;
|
|
|
With
hydrogen;
In
butan-1-ol;
at 200 ℃;
for 1h;
under 11251.1 Torr;
|
|
|
With
hydrogen;
In
tetrahydrofuran;
at 160 ℃;
for 3h;
under 7500.75 Torr;
|
68 %Chromat. 31 %Chromat. |
|
With
hydrogen;
at 240 ℃;
under 760.051 Torr;
|
|
|
With
hydrogen;
In
tetrahydrofuran;
at 150 ℃;
for 3h;
under 7500.75 Torr;
Reagent/catalyst;
Autoclave;
Sealed tube;
|
|
|
With
hydrogen;
In
1,4-dioxane;
at 220 ℃;
for 5h;
under 22502.3 Torr;
Autoclave;
|
85 %Chromat. 15 %Chromat. |
2,5-bis(hydroxymethyl)furan diacetate
2,5-dimethyltetrahydrofuran
2,5-dimethylfuran
| Conditions | Yield |
|---|---|
|
With
palladium on carbon; hydrogen;
In
tetrahydrofuran;
at 90 ℃;
for 2h;
under 12929 Torr;
|
5-Methylfurfural
5-hexyn-2-one
acetic anhydride
2,5-hexanedione
1,4-dimethyl-7-oxabicyclo<2.2.1>hept-5-ene-2,3-dicarboxylic anhydride
2,5-dimethoxy-2,5-dimethyl-2,5-dihydro-furan
2-(bromomethyl)-5-methylfuran
succinic acid
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