Hindered amine antioxidant preparation method

A technology of hindered amines and antioxidants, applied in the field of organic chemical synthesis, can solve the problems of harsh preparation conditions of antioxidants, poor compatibility of antioxidants, easy dissolution, etc., and achieve good anti-solvent extraction performance and not easy to color , good compatibility effect

Active Publication Date: 2018-06-15
PETROCHINA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The main purpose of the present invention is to provide a preparation method of hindered amine antioxidants, to overcome the harsh preparation conditions of antioxidants in the prior art, the poor compatibility of antioxidants, and the problems of easy dissolution

Method used

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preparation example Construction

[0036] The invention discloses a method for preparing hindered amine antioxidants, and the method specifically includes:

[0037] (1) Synthesis of intermediate (Ⅰ): First, dissolve the p-haloaniline compound and the accelerator N,N-diisopropylethylamine in tetrahydrofuran and drop them at low temperature (preferably -5℃~5℃) Add acid halide compound, react at room temperature for a certain period of time (preferably 3-7h), after the completion of the reaction, add a certain amount of saturated NH to the reaction mixture 4 Cl aqueous solution was used to stop the reaction, and then the organic phase was extracted with a certain amount of ethyl acetate. 2 SO 4 Drying, and then drying under vacuum conditions, to obtain intermediate (I).

[0038] (2) Synthesis of intermediate (Ⅱ): Dissolve intermediate (Ⅰ) in ethanol, N 2 Protect, add dropwise the ethanol solution of chain fatty amine at room temperature, react at 70-90°C for 60-80h, the reaction mixture is concentrated under vacuum, and...

Embodiment 1

[0045] This embodiment provides a method for preparing a novel hindered amine antioxidant, which includes the following steps:

[0046] Step 1, accurately weigh 60g of p-bromoaniline and 67.6g of N,N-diisopropylethylamine and dissolve in 1.5L of tetrahydrofuran, slowly add 34.7g of acryloyl chloride dropwise while stirring at 0°C, and react for 4h at 25°C. Add saturated NH to the reaction mixture 4 1L Cl solution was used to stop the reaction, and then extracted with 3L ethyl acetate, Na 2 SO 4 After dehydration, filtration, and vacuum drying at 30°C, N-(4-bromophenyl)acrylamide (I) is obtained.

[0047] Step two, accurately weigh out 60g of N-(4-bromophenyl)acryloyl chloride and dissolve it in 1.0L of ethanol. 2 Under protection, 24.6g of dodecylamine was slowly added dropwise while stirring at 25°C, and reacted for 72h at 85°C. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography. The eluent used was petroleum ether: ethyl acetate = 10:1...

Embodiment 2

[0056] Step one: accurately weigh 60g of p-bromoaniline and 67.6g of N,N-diisopropylethylamine, dissolve in 1.5L of tetrahydrofuran, slowly add 39.5g of acryloyl chloride dropwise while stirring at 0°C, and react for 4h at 25°C. Add saturated NH to the reaction mixture 4 1L Cl solution was used to stop the reaction, and then extracted with 3L ethyl acetate, Na 2 SO 4 After dehydration, filtration, and vacuum drying at 30°C, N-(4-bromophenyl)acrylamide (I) is obtained.

[0057] Step two, accurately weigh out 60g of N-(4-bromophenyl)acryloyl chloride and dissolve it in 1.0L of ethanol. 2 Under protection, 26.5g n-tetradecylamine was slowly added dropwise while stirring at 25°C, and reacted for 75h at 85°C. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography. The eluent used was petroleum ether: ethyl acetate = 10:1 to obtain 3,3'-tetradecylamine-bis-(4-bromophenylhydrazine) ) Propionamide (II).

[0058] Step 3: Weigh accurately 28.2g 3,3'-...

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Abstract

The invention discloses a hindered amine antioxidant preparation method, which comprises: (1) carrying out a substitution reaction on a halogenated aniline compound and an acyl halide compound to produce an intermediate (I); (2) carrying out a carbon-carbon double bond addition reaction on the intermediate (I) and chain-like fatty amine to produce an intermediate (II); and (3) carrying out a substitution reaction on the intermediate (II) and a 2-naphthylamine compound to generate the hindered amine antioxidant, wherein the acyl halide compound contains unsaturated carbon-carbon double bond. According to the present invention, the prepared hindered amine antioxidant has advantages of good compatibility with polymers, good migration resistance and good solvent-extraction resistance, and canbe used for the anti-aging of a variety of polymer materials.

Description

Technical field [0001] The invention relates to a method for preparing a novel hindered amine antioxidant, which belongs to the technical field of organic chemical synthesis. Background technique [0002] Antioxidant is an antioxidant often added to polymer materials, which can prevent polymer materials from losing their performance due to heat and oxygen during processing, storage and use. Commonly used antioxidants include hindered phenolic antioxidants. Hindered amine antioxidants and hindered amine antioxidants. Among them, hindered amine antioxidants can not only prevent thermal oxidation of polymer materials, but also prevent photooxidation. Therefore, they are widely used in the field of polymer materials. [0003] At present, the main antioxidants used in polymer materials, especially polyolefin materials, are mostly hindered phenolic antioxidants, while amine antioxidants are generally easy to color and are generally not suitable for plastic products. However, amine antio...

Claims

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Application Information

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IPC IPC(8): C07C231/12C07C237/04C08L23/06C08K5/20C08K5/526
CPCC07C231/02C07C231/12C08K5/20C08K5/526C08L2201/08C07C237/04C07C233/15C08L23/06
Inventor 王华王俊宋磊李翠勤张瑞杨勇施伟光高宇新张志秋任鹤王玉如王斯晗王嘉明郭常辉宫向英姜进宪马丽杨琦王文燕孙彬彬和树立李冬霞张怀志梁利伟田炳权李波
Owner PETROCHINA CO LTD
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