Carbon Dioxide → HCID 23077197, compound

HRID 2265777Notes

Reaction equation

HRID 2265777 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH3:7].[C:8](=[O:13])([O:11]C)[O:9][CH3:10].[C:14](=O)=O>CO>[CH3:10][O:9][C:8](=[O:11])[O-:13].[CH3:1][N+:2]1[CH:6]=[CH:5][N:4]([CH3:14])[C:3]=1[CH3:7]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 12021Dimethyl CarbonateHCID 156171,2-Dimethylimidazole2×

Product 1

HCID 23077197HCID 23077197, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

96 parts of 1,2-dimethylimidazole (CUREZOL 1.2DMZ manufactured by Shikoku Chemicals Corporation), 135 parts of dimethyl carbonate and 192 parts of methanol were put into an autoclave made of a stainless steel equipped with a cooling condenser and mixed homogenously. After nitrogen substitution, the temperature was then raised to 130° C. while being sealed, so as to initiate a reaction. At the beginning, the pressure was approximately at 4.5 Kg/cm2, but it was gradually raised due to generation of carbon dioxide, so that the gasses were appropriately released from the upper part of the cooling condenser, adjusted at a pressure of about 7 Kg/cm2 or less. After 60 hours, they were cooled at 30° C., and the result of the reacted solution by means of 1H-NMR showed that 1,2-dimethylimidazole was disappeared and 1,2,3-trimethylimidazolium monomethyl carbonate was produced approximately under a quantitative theory. Into 415 parts of the resultant solution of 1,2,3-trimethylimidazolium monomethyl carbonate, methanol and dimethyl carbonate, 205 parts of an aqueous solution of fluoroboric acid at a concentration of 42 wt % was gradually put in drops while stirring at a temperature of 25° C. over a period of about 30 minutes. As putting it in drops, bubbles of carbon dioxide were generated. Finishing the dropping and the generation of the bubbles, all the solvents were removed at a pressure of 20 Torr and at a temperature of 150° C., so as to obtain 194 parts of a white solid (3). The examinations of 1H-NMR, 19F-NMR, 13C-NMR and HPLC of the white solid (3) resulted in showing that 98 mol % of 1,2,3-trimethylimidazolium tetrafluoroborate (which is hereinafter shortened as “TMI.BF4”), 2 mol %, in total, of 1,2,3-trimethyl-4-carboxylate imidazolium and 1,2,3-trimethyl-4-carboxy-5-carboxylate imidazolium.

Workup

  1. customequipped with a cooling condenser
  2. additionmixed homogenously
  3. customwhile being sealed
  4. customa reaction
  5. temperaturethey were cooled at 30° C.
  6. customthe result of the reacted solution by means

Sources & evidence

ORD record
ord-514c88d0b4f540759e7153d87f9aae0d
Source dataset
uspto-grants-2010_12
Patent number
US07858242B2

Reaction notes

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