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Table 1 The hydroxylation of methyl linoleate (ML) in presence of the iron catalyst with different sulfate metal ions

From: Efficient and selective catalytic hydroxylation of unsaturated plant oils: a novel method for producing anti-pathogens

Entry Catalyst Ligands Conv.% Yield of CHLM%
1 FeCl3 Na2S2O8 52.2 N.D
2 FeCl3·6H2O Na2S2O8 67.3 18.6 ± 1.4
3 FeCl2·4H2O Na2S2O8 45.5 21.3 ± 5.4
4 Fe2(SO4)3 Na2S2O8 58.1 13.5 ± 4.6
5 FePc Na2S2O8  > 90 N.D
6a Fe3+-cit·H2O Na2S2O8 100 95.3 ± 3.2(88.7 ± 3.3)
7 Fe3+-cit·H2O Na2S2O3·5H2O 87.9 81.7 ± 3.5
8 Fe3+-cit·H2O NaO3V 82.0 14.2 ± 4.2
9b Fe3+-cit·H2O Na2SeO3 100 18.3 ± 5.2
10 Fe3+-cit·H2O NaCNBH3 100 21.3 ± 2.1
11c Fe3+cit· H2O Na2S2O8 100 33.4 ± 2.5
12d Fe3+-cit·H2O Na2S2O8 97.2 ± 1.3 73.2 ± 5.2
13 Fe3+-cit·H2O 19.7 ± 2.1 11.5 ± 1.5
14 Na2S2O8 100 38.2 ± 4.1
15 Fe3+-cit·H2O Sc(OTf)3 54 N.D
16 Fe3+-cit·H2O H2O2 80.2 ± 5.5 59.4 ± 5.2
  1. Condition: in mixture solvent MeCN/H2O (v/v, 4 mL/1 mL), the 1.0 mmol (316.6 µL), of methyl linoleate was added to the solution containing Fe(III) citrate -monohydrate 0.05 mmol and Na2S2O8 (6 equiv.). Reaction mixture was stirred 24 h at 80 °C under O2 balloon. Yield determined by HPLC with internal standard
  2. aIsolated and, determined yield by 1H NMR analysis with internal standard, N.D. = Not detected
  3. bReaction at 50 °C
  4. cReaction under Argon
  5. dReaction under air