Abstract
Acidic ionic liquids based on phosphonium chloride and metal chlorides-recyclable media and catalysts in the Diels-Alder reaction Acidic ionic liquids based on trihexyltetradecylphosphonium chloride-P6.6.6.14 Cl and six different metal chlorides (YCl3, YbCl3, MgCl2, ZnCl2, CuCl2, InCl3) were prepared. The molar fraction of metal chloride (XMClx) used for the formation of acidic ionic liquids with P6.6.6.14 Cl was changed in the range from 0.3 to 0.5. The high catalytic activity in the Diels-Alder reaction of cyclopentadiene and various αβ-unsaturated carbonyl compounds showed ionic liquids at XMClx≤0.4. In general, the highest product yields and endo:exo ratios were achieved in the acidic ionic liquids formed from MgCl2, YCl3 and YbCl3. Thermogravimetric analysis suggested that the prepared ionic liquids were thermally stable up to nearly 400°C. Additionally, they could be reused with only little loss of catalytic activity after the 4th recycle.
Highlights
Reactions catalyzed by the Lewis or Br nsted acids and by super acids play an important role in the organic technology
Similar acidic catalytic systems were formed. They were based on the other metal chlorides, such as iron(III) chloride, zinc(II) chloride and imidazolium, pyridinium or phosphonium halogenides[3, 4, 5]
XMClx is the molar fraction of metal chloride in its mixture with P6.6.6.14Cl used to the formation of acidic ionic liquids
Summary
Acidic ionic liquids based on trihexyltetradecylphosphonium chloride – P Cl 6.6.6.14 and six different metal chlorides (YCl3, YbCl3, MgCl2, ZnCl2, CuCl2, InCl3) were prepared. The molar fraction of metal chloride (XMClx) used for the formation of acidic ionic liquids with P Cl 6.6.6.14 was changed in the range from 0.3 to 0.5. The high catalytic activity in the Diels-Alder reaction of cyclopentadiene and various α,ß-unsaturated carbonyl compounds showed ionic liquids at XMClx≥0.4. The highest product yields and endo:exo ratios were achieved in the acidic ionic liquids formed from MgCl2, YCl3 and YbCl3. Thermogravimetric analysis suggested that the prepared ionic liquids were thermally stable up to nearly 400°C. They could be reused with only little loss of catalytic activity after the 4th recycle
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