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A shielding phenolic compound, its manufacture method and its application as antioxidant

A manufacturing method and technology of phenolic compounds, applied in lubricating compositions, additives, organic chemistry, etc.

Active Publication Date: 2019-02-01
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still room for improvement in the high temperature oxidation resistance of these prior art compounds

Method used

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  • A shielding phenolic compound, its manufacture method and its application as antioxidant
  • A shielding phenolic compound, its manufacture method and its application as antioxidant
  • A shielding phenolic compound, its manufacture method and its application as antioxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0232] In a 500ml four-neck flask equipped with a stirrer, thermometer, condenser and dropping funnel, add 58.79g (0.323mol) of 2-tert-butyl-6-mercaptophenol, 6.88g (0.048mol) of boron trifluoride Ethyl ether (catalyst for alkylation reaction), 100ml of n-hexane solvent and 161.61g (0.162mol) of polyisobutene (Mn=1000, manufactured by Jihua Group Fine Chemicals Co., Ltd.) were reacted at 80°C for 2h. After the reaction, the reaction mixture was washed once with 5% potassium hydroxide solution by mass fraction, and washed to neutrality with hot water to remove the catalyst, and then the solvent and unreacted phenol were distilled off under reduced pressure to obtain polyisobutylene mercaptophenol, hydroxyl The value was 53.49 mgKOH / g. For the determination of hydroxyl value, refer to the acetic anhydride method in GB / T7383-2007.

[0233] An example reaction is as follows:

[0234]

[0235] From the proton nuclear magnetic spectrum analysis of the polyisobutylene mercaptoph...

Embodiment 2

[0237]

[0238] Under a nitrogen protection atmosphere, in a 250ml four-necked flask equipped with a stirrer, a thermometer, a condenser and a dropping funnel, add 30.58 grams (156 mmol) of 2-mercapto-4-methyl-6-methylphenol, 9.29 grams ( 112mmol) formaldehyde, 32.38g (176mmol) N-phenyl-p-phenylenediamine and 100mL toluene, stirred rapidly, and reacted at 100°C for 2h. After the reaction was finished, the solvent and a small amount of water generated were distilled off under reduced pressure, and the shielded phenol product with the structure shown in the title was obtained through column chromatography separation.

[0239] Product characterization data are as follows:

[0240] 1 H NMR (300MHz, CDCl 3 ): δ1.40(9H), 2.37(3H), 4.02(1H), 4.83(2H), 6.95-7.00(12H), 7.26(2H), 7.55(1H);

[0241] 13 C NMR (75MHz, CDCl 3 ): δ21.2, 30.1, 34.1, 49.9, 114.3, 118.9, 119.4, 121.8, 122.2, 125.8, 126.5, 129.5, 131.8, 132.3, 133.5, 143.3, 150.8;

[0242] C 24 h 28 N 2 Calculated OS...

Embodiment 3

[0244]

[0245] Under nitrogen protection atmosphere, in the 250ml four-necked flask that stirrer, thermometer, condenser tube and dropping funnel are equipped with, add 31.65 grams (133mmol) 2,6-di-tert-butyl-4-mercaptophenol, 1.86 grams (62mmol ) formaldehyde, 28.15 grams (153 mmol) of N-phenyl-p-phenylenediamine, 0.75 grams (7.5 mmol) of hydrochloric acid and 150 mL of isopropanol, stirred rapidly, and reacted at 25 ° C for 24 h. After the reaction was finished, the solvent and a small amount of water generated were distilled off under reduced pressure, and the shielded phenol product with the structure shown in the title was obtained through column chromatography separation.

[0246] Product characterization data are as follows:

[0247] 1 H NMR (300MHz, CDCl 3 ): δ1.36-1.54(18H), 3.75(1H), 4.80(2H), 5.32(1H), 6.80(2H), 6.97(5H), 7.17(2H), 7.26(2H), 7.55(1H) ;

[0248] 13 C NMR (75MHz, CDCl 3 ): δ29.6, 34.6, 51.2, 119.4, 121.8, 126.5, 129.5, 131.4, 136.6, 144.5, 1...

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Abstract

The present invention relates to a screen phenol compound as shown in formula (I), a manufacturing method and application thereof as an antioxidant, groups of the formula (I) are defined as the specification, and by use of the screen phenol compound as the antioxidant, an excellent high temperature oxidation resistance lubricating oil composition can be produced.

Description

technical field [0001] The present invention relates to a novel shielding phenol compound. Specifically, the present invention relates to a shielded phenolic compound containing sulfur and aromatic amines, a method for its manufacture and its use as an antioxidant. Background technique [0002] Oxidation stability of oil is one of the most important indicators of oil performance. For example, for almost all lubricating oils, antioxidants must be added to prolong service life. Moreover, with the rapid development of modern automobiles and machinery industries, the power of engines and mechanical equipment continues to increase, the operating temperature of lubricating oils increases further, and the oxidation problem becomes more prominent. At the same time, the quality level of lubricating oil continues to improve, requiring lubricating oil to further extend the oil change interval, which puts forward higher requirements for the high-temperature oxidation stability of lubr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/25C07C319/14C07D219/08C07D279/20C07D513/04C07C323/32C10M135/30C10M135/36C10N30/10
Inventor 苏朔龙军段庆华周涵武志强李新华赵毅赵晓光
Owner CHINA PETROLEUM & CHEM CORP
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