Novel Schiff base type amine antioxidant as well as preparation method and application thereof

A technology of Schiff base amine and antioxidant, applied in the field of antioxidants, can solve problems such as comprehensive performance needs to be further improved, and achieve the effects of excellent thermal stability, simple post-processing, and simple and easy operation process

Inactive Publication Date: 2018-05-25
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the overall performance of such Schiff base antioxidants as lubricating oils and fuel oil additives needs to be further improved.

Method used

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  • Novel Schiff base type amine antioxidant as well as preparation method and application thereof
  • Novel Schiff base type amine antioxidant as well as preparation method and application thereof
  • Novel Schiff base type amine antioxidant as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0054] In some preferred embodiments, the preparation method comprises: taking aldehydes or ketones, diphenylamine and / or diphenylamine derivatives and / or phenothiazines and / or phenothiazine derivatives in the presence of a catalyst react in a liquid phase reaction medium to obtain the Schiff base amine antioxidant.

[0055] For example, in a more specific embodiment, the preparation method may include: reactant A and reactant B exist in catalyst C, and react in optional liquid phase reaction medium D, thereby forming suitable, especially suitable As the reaction product of antioxidants, namely the aforementioned Schiff base amine antioxidants.

[0056] For example, the following components can be used as reactants to form the products of the invention:

[0057] Reactant A: aldehydes or ketones include alkyl aldehydes or ketones and / or aromatic aldehydes or ketones; preferably, the reactant A is selected from aldehydes, which can be non-limitingly selected from various types ...

Embodiment 1

[0078] Embodiment 1 Benzaldehyde 5g-7.5g, 4-aminodiphenylamine 12g-15g and sulfuric acid 0.1g-1g are dissolved in about 100mL tetrahydrofuran, join in the thick-walled pressure-resistant glass bottle that has magneton, at reaction temperature React under the condition of 50°C-110°C for 3h-8h. After the reaction is over, cool the reaction mixture to room temperature, remove the solvent under reduced pressure, and recrystallize to obtain the target product. 1 H NMR spectrum, 13 C NMR spectra can be found separately Figure 1-Figure 2 . 1 H NMR (400MHz, DMSO-d 6 )δ6.85(t,J=6.8Hz,1H),7.11-7.15(m,4H),7.24-7.30(m,4H),7.49(s,3H),7.92(s,2H),8.33(s ,1H),8.66(s,1H). 13 C NMR (100MHz, DMSO-d 6 )δ116.87, 117.04, 119.83, 122.41, 128.25, 128.73, 129.21, 130.80, 136.51, 142.21, 142.95, 143.23, 156.79. IR (film): 745, 824, 1315, 1450, 1508, 158, 158, The average yield is more than 70%, the preferred product yield is greater than 95%, and the product purity is greater than 98%.

Embodiment 2

[0079] Example 2 Dissolve 6g-9g of p-tolualdehyde, 14g-17g of 4-aminodiphenylamine and 0.1g-2g of hydrochloric acid in about 100mL of chloroform, and add them to a thick-walled pressure-resistant glass bottle with a magnet , react at a reaction temperature of 60°C-100°C for 6h-10h, after the reaction is over, cool the reaction mixture to room temperature, remove the solvent under reduced pressure, and recrystallize to obtain the target product. 1 H NMR spectrum, 13 C NMR spectra can be found separately Figure 3-Figure 4 . 1 H NMR (400MHz, CDCl 3 )δ2.38(s,3H),5.76(s,1H),6.89-6.93(m,1H),7.05(d,J=8Hz,4H),7.18-7.27(m,6H),7.77(d, J=7.6Hz,2H),8.44(s,1H). 13 C NMR (100MHz, CDCl 3 )δ21.54,117.54,118.48,120.83,122.14,128.52,129.30,129.42,133.87,141.33,143.13,145.18,157.89.IR(film):686,738,826,1333,1348,1498,1530,1587,1603,1623,2920, 3034, 3398. The average product yield in this example is above 50%, the preferred product yield is greater than 75%, and the product purity is great...

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Abstract

The invention discloses a novel Schiff base type amine antioxidant as well as a preparation method and application thereof. The novel Schiff base type amine antioxidant comprises a compound shown as aformula (I) or (II) in the description, wherein the R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8>, R<9> and R<10> are at least selected from H or C1 to C20 straight-chain or branch-chain alkyls or contain benzene substitutes or contain O, S, N, P and/or Si alkyl or aryl; the R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8>, R<9> and R<10> represent identical groups or different groups; X is at least selected from -S-, -O-, -NH-, or a formula shown in the description, wherein m is 0 or 1. The novel Schiff base type amine antioxidant provided by the invention has excellent thermal stability andgood anti-oxidization performance; the preparation process is simple; the novel Schiff base type amine antioxidant is suitable for large-scale production and can be widely applied to various fields such as lubricating oil, liquid fuel, thermal plastic polymers, resin or oligomers or natural or synthetic plastics or rubber or elastomers.

Description

technical field [0001] The invention relates to an antioxidant, in particular to a novel Schiff base type amine antioxidant, its preparation method and application. Background technique [0002] Lubricating oils are mostly composed of base oils and additives. Lubricating oil additives are special chemical substances added to the base oil to make the lubricating oil acquire some new characteristics or improve some existing characteristics of the lubricating oil. For example, during the long-term storage and use of automobile engine oil (that is, automobile engine lubricating oil), it will inevitably come into contact with air, and then react with oxygen in the air to cause oxidation, especially when lubricated under high temperature and metal catalysis. The hydrocarbons in the oil will be converted into various oxidation products, including acidic substances, deposits, sludge, etc., which will seriously affect the normal operation of the engine and directly affect the normal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/24C07C251/08C07C251/16C07C249/02C07C323/45C07C319/20C07D279/20C10M133/22C10M135/30C10M169/04C10N30/10C10N30/08C10N30/06
CPCC07C251/08C07C251/16C07C251/24C07C323/45C07D279/20C10M133/22C10M135/30C10M169/045C10M2205/0206C10M2215/064C10M2219/087C10M2223/045C10N2030/06C10N2030/08C10N2030/10C10N2010/04
Inventor 俞莎莎冯建湘蔡涛曾红玲刘升高
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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