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. 2020 Aug 12;68(39):10456–10488. doi: 10.1021/acs.jafc.0c02894

Table 2. Overview of Anions Used in HIL Synthesis Divided by Reaction Types.

anion type of reaction yield (%) refs
MCPA metathesis 86–99 (16,25,43,45,50,55,56,58,59,63,73,79)
  quaternary ammonium hydroxide resulting from KOH in methanol 86–99 (37,47,55,60,67,68)
2,4-D metathesis 82–99 (25,45,46,48,59,63,73)
  quaternary ammonium hydroxide resulting from KOH in methanol 89–99 (47,67)
  quaternary ammonium hydroxide resulting from KOH in ethanol 90–92 (41)
  quaternary ammonium hydroxide with the use of ion-exchange resin 82–99 (46)
  from commercially available choline hydroxide 97 (44)
dicamba metathesis 90–99 (26,39,45,51,58,63,73)
  quaternary ammonium hydroxide resulting from KOH in methanol 90–98 (47,67,68)
  quaternary ammonium hydroxide with the use of ion-exchange resin 74–99 (26,51)
fomesafen metathesis 81–98 (32)
MCPP metathesis 90–98 (25,45,51,63,73)
  quaternary ammonium hydroxide resulting from KOH in methanol 92–97 (47,67)
  quaternary ammonium hydroxide with the use of ion-exchange resin >92 (51,66)
metsulfuron-methyl (MSM) metathesis 91–98 (29)
  quaternary ammonium hydroxide resulting from KOH in methanol 90–99 (29)
diclofop metathesis   (8)
clodinafop metathesis   (8)
bentazone metathesis 83–97 (24)
clopyralid metathesis   (27)
4-CPA metathesis 85–91 (25)
bromoxynil metathesis 94–99 (23)
pelargonate metathesis 93–99 (33,62)
  quaternary ammonium hydroxide resulting from KOH in methanol 96–99 (34)
  from commercially available choline hydroxide 98 (77)
iodosulfuron-methyl (ISM) metathesis 88–98 (62)
glyphosate quaternary ammonium hydroxide resulting from KOH in methanol 90–98 (31,42)
2,4-DP quaternary ammonium hydroxide resulting from KOH in methanol 89–95 (57)
  quaternary ammonium hydroxide with the use of ion-exchange resin 91–98 (65)
nicosulfuron quaternary ammonium hydroxide resulting from KOH in methanol 86–93 (30)
MCPB quaternary ammonium hydroxide with the use of ion-exchange resin 91–96 (64)
mesotrione quaternary ammonium hydroxide resulting from KOH in methanol 87–95 (38)