Method for preparing nonanal by selective oxidation of erucic acid or ester thereof
A selective and nonanal technology, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, can solve problems such as heavy metal pollution, and achieve mild reaction conditions, good selectivity, and environmental friendliness.
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Embodiment 1
[0024] Synthesis of isosterveol derivative amino alcohols: Isosterveol derivative amino alcohols were synthesized according to the literature (Lai Hongtao, Synthesis of novel diamine chiral ligands and their application in asymmetric organic catalysis Research, 2016, Master Thesis of Zhengzhou University).
[0025] Synthesis of isosterveol derivative aminoalcohol glyoxal condensate: Add 20mL methanol and 9.4g (0.025mol) isosterveol derivative aminoalcohol into a 100mL three-neck flask, stir and drop glyoxal 1.9g (0.013mol), stirred at room temperature for 8 hours, filtered the precipitate, washed with methanol, and dried in vacuum at 50°C to obtain 8.1g of isosterveol derivative amino alcohol glyoxal condensate, with a yield of 80.2%. Its structural formula is:
[0026] ;
[0027] 1H NMR (400 MHz, CDCl3, TMS): δ7.5 (d, 2H), 4.06–4.11 (m, 4H), 3.82 (d,2H),, 3.33 (m, 4H), 3.04 (d, 2H) , 2.49 ( s, 2H), 2.15 (d, 2H), 1.42–1.83(m,18H), 1.83–1.09 (m, 14H) , 1.27 (s, 6H), 1.16 (...
Embodiment 2
[0033] Add 3.5 g (0.01 mol) methyl erucate, 0.083 g (0.0001 mol) manganese complex of isosteviol derivatives, 10.5 g 1,4-dioxane, 1.0 g (0.008 mol) to the autoclave For tert-butanol peroxide, oxygen was introduced to the pressure of the reactor to 0.2MPa, the reaction temperature was 100°C, and the reaction time was 60 minutes. The specific reaction results are shown in Table 1.
[0034] Nonanal (C 9 h 18 O): 1H NMR (400 MHz, CDCl 3 , TMS): δ9.7 (s, 1H), 2.4 (d, 2H), 1.6 (d, 2H), 1.28–1.33(m, 10H), 0.91 (d, 3H); GC-MS: [M] + 142, [M-27] + 115.
[0035] 2,4-Dinitrononanalphenylhydrazone (C 15 h 22 N 4 o 4 ): 1H NMR (400 MHz, CDCl 3 , TMS): δ8.8 (s,1H), 8.3 (d, 1H), 7.5 (s, 1H), 7.0 (s, 1H), 6.8(d, 1H), 1.29-1.33 (m, 14H), 0.9 (t, 3H).
Embodiment 3
[0037] Add 3.7 g (0.01 mol) ethyl erucate, 0.25 g (0.0003 mol) manganese complex of isosteviol derivatives, 14.8 g 1,4-dioxane, 1.3 g (0.01 mol) to the autoclave For tert-butanol peroxide, oxygen was introduced until the pressure of the reactor was 0.5 MPa, the reaction temperature was 140° C., and the reaction time was 120 minutes. The specific reaction results are shown in Table 1.
[0038] Nonanal (C 9 h 18 O): 1H NMR (400 MHz, CDCl3 , TMS): δ9.7 (s, 1H), 2.4 (d, 2H), 1.6 (d, 2H), 1.28–1.33(m, 10H), 0.91 (d, 3H); GC-MS: [M] + 142, [M-27] + 115.
[0039] 2,4-Dinitrononanalphenylhydrazone (C 15 h 22 N 4 o 4 ): 1H NMR (400 MHz, CDCl 3 , TMS): δ8.8 (s,1H), 8.3 (d, 1H), 7.5 (s, 1H), 7.0 (s, 1H), 6.8(d, 1H), 1.29-1.33 (m, 14H), 0.9 (t, 3H).
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