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Cardanol-based antioxidant as well as preparation method and application thereof

A cardanol-based, antioxidant technology is applied in the preparation of amino hydroxy compounds, chemical instruments and methods, preparation of organic compounds, etc. The effect of easy handling, reduced pollution, and simple and easy operation

Active Publication Date: 2018-04-20
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

[0005] Although the antioxidant performance of these existing cardanol-based antioxidants has been improved compared with that of cardanol, the improvement range is limited, especially the application in high-temperature environments is limited; Harsh conditions and high costs

Method used

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  • Cardanol-based antioxidant as well as preparation method and application thereof
  • Cardanol-based antioxidant as well as preparation method and application thereof
  • Cardanol-based antioxidant as well as preparation method and application thereof

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preparation example Construction

[0048] Another aspect of the present invention provides a method for preparing the cardanol-based antioxidant, comprising: taking cardanol and / or cardanol derivatives, aromatic amines and / or aromatic amine derivatives in a liquid phase system with The coupling reagent reacts to obtain the cardanol-based antioxidant. In some embodiments, the preparation method of the cardanol-based antioxidant includes: taking cardanol and / or cardanol derivatives, aromatic amines and / or coupling reagents in the liquid phase reaction system, The reaction is carried out under the condition of a catalyst to obtain the cardanol-based antioxidant.

[0049] In some embodiments, the preparation method specifically includes: taking cardanol and / or cardanol derivatives, aldehydes, arylamines and / or arylamine derivatives and / or amino aromatic heterocycles and / or amino aromatic heterocycles The ring derivatives, coupling reagents and catalysts are mixed and reacted in a liquid phase reaction medium to ob...

Embodiment 1

[0071] Example 1: After fully drying the 250ml three-necked reaction flask, the reactant hydrogenated cardanol (3.04g), paraformaldehyde (0.45g), p-aminodiphenylamine (1.84g), and reaction solvent methanol (50ml) were added successively , the temperature was raised to 85° C., and the reaction was stirred for 5 hours, and water was removed during the reaction. Then, it was washed and filtered with methanol, and the filter cake was recrystallized three times with ethyl acetate, and after drying, 4.5 g of a light yellow solid product was obtained. of the product 1 H NMR spectrum (DMSO, 400MHz) and 13 C NMR spectrum (DMSO, 100MHz) can be found in figure 2 with image 3 .

Embodiment 2

[0072] Embodiment 2: After fully drying the three-necked reaction flask of 250ml, add reactant hydrogenated cardanol (6.08g), paraformaldehyde (0.75g), p-phenylenediamine (1.1g), reaction solvent methanol (70ml) successively, The temperature was raised to 85° C., the reaction was stirred for 5 hours, and water was removed during the reaction. Then, it was washed and filtered with methanol, and the filter cake was recrystallized three times with ethyl acetate, and after drying, 6.8 g of a light-colored solid product was obtained. of the product 1 H NMR spectrum (DMSO, 400MHz) and 13 C NMR spectrum (DMSO, 100MHz) can be found in Figure 4 with Figure 5 .

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Abstract

The invention discloses a cardanol-based antioxidant as well as a preparation method and application thereof. The cardanol-based antioxidant contains a compound with a structure shown as a formula (1): (shown in the description), wherein n ranges from 0 to 3; R1 and R2 are respectively and independently selected from H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl; at least one of R3 and R4 has a structure shown as a formula (2) or (3): (shown in the description); R and R' are respectively and independently selected from H, alkyl, cycloalkyl, aryl, alkaryl or aralkyl; R5 is selected from -S-, -O-, -NH- or -(CH2)n'-; n' ranges from 0 to 3; Ra and Rb are respectively and independently selected from H, -OH, -SH, -NH2, alkyl, cycloalkyl, aryl, alkaryl or aralkyl; m and m' are any integer of 0 to 3 respectively. The cardanol-based antioxidant disclosed by the invention has the characteristics of greenness, environmental protection, antioxidation property, excellent thermal stability and extreme pressure resistance and the like; a preparation process has the advantages of simplicity, feasibility, mild conditions and wide application prospect in the fields of multiple oil products, fuel, plastic, rubber, fibers, coatings and the like.

Description

technical field [0001] The invention relates to an antioxidant, in particular to a cardanol-based antioxidant, its preparation method and application. Background technique [0002] Bio-based additives are renewable, low-toxic and degradable, and have a mitigating effect on increasingly serious energy and environmental problems, so they have received more and more attention in recent years. In order to maximize the utilization of renewable resources, the design of biomass molecules must be fully combined with its unique chemical structure through chemical modification. Antioxidants present in natural plants can be used as antioxidants in food, plastics, rubber and lubricating oils because they can directly scavenge peroxyl free radicals formed in the process of oxidative degradation and break the self-oxidative chain reaction. In recent years, many applications of natural antioxidants have focused on extracts, such as cardanol, rosemary extract, birch pyrolysis bio-oil, wood...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/50C07D279/20C07C213/02C08K5/18C08K5/46C08L7/00C09K15/20C09K15/30C10M133/14C10M135/36C10N30/10
CPCC07C213/02C07C215/50C07D279/20C08K5/18C08K5/46C08L7/00C09K15/20C09K15/30C10M133/14C10M135/36C10M2215/066C10M2219/108C10N2030/10
Inventor 冯建湘赵红冉曾红玲刘升高
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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