SU785291A1 - N-(3,5-ditert-butyl-4-oxybenzyl)-para-aminophenol as antioxidative additive - Google Patents

Description

The invention relates to a novel compound, namely, N- (3,5-Ditretbu-4-oxybenzyl) -p-aminophenol forf (which can be used as an antioxidant additive to synthetic essential oils. Phenyl-oC-naphthylamine in As an antioxidant additive to synthetic essential oils, added to the oil in the amount of 0.050, 5 wt.% l. The disadvantage of phenyl-o.-naphthylamine is its low temperature resistance (at temperatures above the phenyl-i-naphthyl compound condenses with loss of antioxidant properties). also diisobtide Enylamine as an antioxidant additive to synthetic ether maynes, injected with 1c oil in an amount of 0.5-2 wt.% 2. The disadvantage of this technical solution is the high consumption of antioxidant (0.5-2 wt.%). The aim of the invention is Identification of compounds that can be used as an antioxidant additive to synthetic essential oils. The goal is achieved with the help of N - (3, 5-di-nitrate-butyl-4-oxy-benzyl) -n-aminophenol. The latter is obtained by reacting 3/5-di-tert-butyl-4-hydroxybenzyl chloride, with p-aminophenol at 35-80 ° C in the presence of triethylamine as an acceptor of hydrogen chloride. The drawing shows the kinetic curves for oxygen as measured by pentaerythritol ether and at 0.02 mol / l of the proposed compound. Example 1. To a solution of 0.1 mol of para-aminophenol in 100 ml of dimethylformamide, 0.1 mol is added with stirring. 2, b-ditertbutyl-4-hydroxybenzyl chloride. The reaction is exothermic, with the result that the temperature of the reaction mixture rises to b8-70 ° C. After the temperature drops to 35-40 ° C, O, 1 mole of triethylamine is added and the reaction mixture is stirred at 70-80 ° C for 4 ° -5 h

Triethylamine hydrochloride is filtered off. Dimethylformamide was removed from the residue by vacuum distillation. The resulting product is recrystallized from ethanol, so pl. 174-176 s, Yield 7080%. Found,%; C 77.00; H 8.82; N 4.16,

Calculated,%: C 77.03; H 8.93 N, 4.28.

The structure of the synthesized compound was proved by IR spectroscopy.

The spectrum is taken in a KBg tablet in the frequency range 400-40000

Absorption bands 1360 (cf.), 2870 (cf.-s), 2920 (cf.), 2970 (s) are characteristic of the tert-butyl group. Shielded phenol OH-group is represented by bands 1165 (cf.), 3620 (cf.-s) see. Bands 775 (bp.), 1430 (cf.) cm can be attributed to the RI-SND-fragment. .

Absorption bands of 1510 cm (cp) are characteristic of the Ph-CH-NH-fragment. The group -CHi-NH corresponds to the band 1120 El.

The NHPhOH fragment includes bands 515 Both (Ph-N), 1230 (cf.) cKf (OH-group oscillations in n-PhOH) 1265 (cf.) cm- (Ph-N) 1470 (

 (cf.) CM- (Ph).

5 g. Antioxidant properties

N- (3, 5- “ittretbutyl-4-oisibechzil) -para-amyiophenol is studied in the presence of aluminum, steel and copper plates with a flow rate of dry air stored through 50 g of synthetic oil, 50 cmUmin for 50 h.

The pentaerythritol ester of the synthetic fatty acid fraction is used as a synthetic oil.

The table shows the results of tests of synthetic essential oil without additives and with antioxidant additives: phenyl-naphthylamine, di-oooctyldiphenylamine N- (3,5-diterbutyl-4-oxybeneyl) -p-aminophenol 1.

Pentaerythritol 55.8 197 ether PE PE-1- 0.05% phenyl0, 19; 6.8 49.5 189 phylamine

38.4

6.1 0.16

Claims (2)

1. Zarubina I. in. And others. Synthesis of antioxidant additives based on aromatic amines i Chemistry and technology of fuels and oils 5,1973, pp.18-19. 2. In the same place, pp.19-21 (prototype). Nagar on the walls of 0.003 +0.009 -0.013 reactor 0.005 +0.010-0.0119 2 $ It 9 e 78 9 vec r 200c