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Butylated hydroxyluene(BHT), also known as antioxidant 264, CAS 128-37-0, Molecular formula C15H24O, antioxidant 264,2, 2,6-di-t-butyl-p-cresol, 2,6-di-t-butyl-4-methylphenol, antioxidant T501 and BHT. It is light yellow powder, and the pure product is white crystal. The color turns yellow when it meets light, and gradually deepens. Soluble in benzene, toluene, methanol, ethanol, isopropanol, butanone, petroleum ether, carbon tetrachloride, ethyl acetate, insoluble in water and dilute alkali solution. Chemical characteristics: 264 has a protective effect against heat and oxygen aging, and is flammable. It can inhibit or delay the oxidation degradation of plastics or rubber and prolong the service life. It is an excellent antioxidant additive for various petroleum products. It is widely used in various lubricating oils, gasoline, paraffin and various raw oils to prevent the increase of acid value or viscosity of lubricating oils and fuel oils. As food antioxidant and stabilizer in food grade plastics and packaged food, it can delay food rancidity.
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Chemical Formula |
C15H24O |
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Exact Mass |
220 |
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Molecular Weight |
220 |
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m/z |
220 (100.0%), 221 (16.2%), 222 (1.2%) |
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Elemental Analysis |
C, 81.76; H, 10.98; O, 7.26 |
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Synthetic butylated hydroxyluene(BHT):
(1) Put the molar ratio of p-cresol and t-butanol 1:1.1 into the reaction kettle for heating and dissolution.
Under the action of catalyst phosphoric acid, the reaction was carried out under strong stirring at 65-70 ℃;
After the reaction is completed, the reaction product is first washed with 10% sodium hydroxide solution to alkaline, and then washed with water to neutral;
Remove the solvent and recrystallize with ethanol to obtain the finished product.
CH3C6H4OH+(CH3)3COH[H3PO4]→BHT
(2) Isobutylene was introduced into the mixture of 98% p-cresol and 2% concentrated sulfuric acid and reacted at 65-70 ℃ for 5 h;
Wash the acid with hot water at 60 ℃, and then wash it with 10% NaOH and hot water to neutral to obtain the crude product.
Dissolve the crude product in 50% hot ethanol, add 0.5% thiourea, filter it while hot, shake it dry, and dry it to obtain the finished product.
The yield is as high as 90% ~ 95%, the purity is 99.5%, and the melting point is > 69.5 ℃.
In industry, the main and auxiliary towers are connected in series.
Firstly, p-cresol and catalyst are added into the main and auxiliary towers, and the temperature of the main tower is controlled at 65-80 ℃, and the temperature of the auxiliary tower is controlled at 50-70 ℃.
Isobutylene gas is introduced from the bottom of the main tower, most of which reacts with p-cresol in the main tower, and the rest comes out from the top of the main tower and enters the bottom of the sub tower to further react with p-cresol.
The reaction cycle of the main tower is controlled at 4-5h. After the reaction is completed, the isobutylene gas is stopped, 20% NaOH solution is added, and the compressed gas is bubbled.
The neutralized alkylation product is separated into crude products by distillation column (8 theoretical trays).
The latter is dissolved in 95% ethanol, ion exchanged to remove inorganic salts, cooled to 10-20 ℃, crystallized, separated and vacuum dried to obtain a product with a melting point greater than 69 ℃.
CH3C6H4OH+(CH3)2C=CH2[H2SO4]→BHT
Butylated hydroxyluene(BHT), chemical name 2,6-di-tert-butyl-4-methylphenol, also known as BHT, antioxidant 264, antioxidant and anti glue agent T501, etc., CAS registration number 128-37-0, is a widely used phenolic antioxidant.
(1) Universal anti-aging agent
Antioxidant 264 is the most commonly used phenolic antioxidant for natural rubber and synthetic rubber, including styrene butadiene rubber, butyl rubber, nitrile rubber, and ethylene propylene rubber. It has a certain protective effect on thermal and oxygen aging, which can inhibit or delay the oxidative degradation of rubber, thereby extending the service life of rubber products. In the rubber industry, antioxidant 264 is widely used and can be used to manufacture various colored and light colored rubber products, latex products, etc. For example, in the production of white, light colored, and transparent rubber products such as rubber shoes and rubber cloth products, antioxidant 264 can play a good anti-aging role, ensuring the quality and performance of the products.
(2) Raw rubber protection and application of latex products
Antioxidant 264 can not only be used in the production of rubber products, but also as a protective agent for raw rubber to prevent oxidation and deterioration during storage and transportation. In the production of latex products, antioxidant 264 can be made into a dispersion and directly mixed into latex to improve the antioxidant properties of latex products. For example, in the production of medical and health products, antioxidant 264 can ensure the quality and safety of the products and extend their service life.
(3) Protection against various aging factors
Antioxidant 264 has a certain protective effect on natural rubber, styrene butadiene rubber, and chloroprene rubber during thermal oxidative aging, and also has a certain protective effect on photo aging and insect pests. During the use of rubber products, they are affected by various factors such as heat, oxygen, and light, leading to aging and deterioration of the rubber. Antioxidant 264 can inhibit the oxidation reaction of rubber and reduce the generation of aging products by eliminating free radicals, thereby protecting the performance of rubber products. For example, in the outdoor use of rubber products, antioxidant 264 can prevent rubber from undergoing photo aging due to light exposure, maintaining the appearance and performance of the product.
(1) General antioxidant3
Antioxidant 264 is a cheap general antioxidant for polyethylene, polypropylene, polystyrene, ABS resin, polyester, cellulose resin and foam plastics, especially suitable for white or light colored products. During the processing and use of plastics, they are affected by factors such as heat and oxygen, leading to oxidative degradation and a decrease in their properties, such as discoloration, brittleness, and strength. Antioxidant 264 can inhibit the oxidation reaction of plastics and extend the service life of plastic products by capturing free radicals and other methods. For example, in the production of food grade plastics and polymer materials for packaging food, antioxidant 264 can ensure the quality and safety of plastic products, preventing food from being contaminated due to plastic oxidation.
(2) The dosage and application of different plastics
In polyethylene and polyvinyl chloride, the dosage of antioxidant 264 is generally 0.01% -0.1%, which can effectively suppress the discoloration and strength decrease of the plastic. In polystyrene and ABS resins, a dosage of less than 1% can prevent changes in plastic properties due to oxidation. In cellulose resin, antioxidant 264 can protect the resin from thermal aging and photo aging, and the dosage is also less than 1%. Although the antioxidant performance of antioxidant 264 may be insufficient in some aspects compared to antioxidants such as 1010 and 1076, it still has a wide range of applications in some plastic products that require high cost and not particularly strict performance requirements.
(3) Comparison with other antioxidants and application trends
Antioxidant 1010 is a high-performance antioxidant widely used in polyethylene, polypropylene, polyoxymethylene, ABS resin, PS resin PVC, Engineering plastics, rubber, and petroleum products, etc. Compared with antioxidant 264, antioxidant 1010 has better antioxidant performance, but its price is relatively high. Antioxidant 1076 is an excellent non polluting and non-toxic antioxidant with good heat resistance and water extraction resistance. Butylated hydroxyluene(BHT) is widely used in polyolefins, polyamides, polyesters, polyvinyl chloride, ABS resins, and petroleum products. It is often used in conjunction with antioxidant DLTP to improve its antioxidant effect. In recent years, due to the low molecular weight and high volatility of antioxidant 264, its antioxidant effect has decreased in some plastic products processed at high temperatures and stored for a long time. Therefore, it has gradually been replaced by other low volatility antioxidants abroad. However, in some developing countries and specific application areas, antioxidant 264 still holds a significant proportion.
Petroleum industry
(1) Lubricant antioxidant
Antioxidant 264 is an excellent antioxidant for various lubricating oils, which can prevent the increase of acid value or viscosity caused by oxidation of lubricating oils and prolong their service life. During the use of lubricating oil, it is affected by factors such as high temperature, high pressure, and metal catalysis, leading to oxidation reactions and the formation of acidic substances and colloids, resulting in a decrease in the performance of the lubricating oil. Antioxidant 264 can inhibit the oxidation reaction of lubricating oil by capturing free radicals and maintaining the stability of lubricating oil performance. For example, in automotive engine lubricating oil, industrial gear lubricating oil, etc., antioxidant 264 can ensure the normal lubrication performance of the lubricating oil and reduce the wear of mechanical equipment.
(2) Antioxidant properties of secondary processed mineral oils such as gasoline and paraffin
In addition to lubricating oil, antioxidant 264 can also be used as an antioxidant for secondary processing of gasoline, paraffin, and other mineral oils. During the storage and use of gasoline, substances such as gum are generated due to oxidation, leading to a decrease in the quality of gasoline and affecting the normal operation of the engine. Antioxidant 264 can prevent the oxidation and deterioration of gasoline, and maintain the stability of gasoline performance. In mineral oils such as paraffin, antioxidant 264 can also exert antioxidant effects, extending the service life of mineral oils.
(3) Collaborative application with other petroleum products
Antioxidant 264 can be used in conjunction with other antioxidants and additives to enhance the antioxidant and overall performance of petroleum products. For example, when used in conjunction with antioxidant DLTP, it can enhance the antioxidant effect and extend the service life of petroleum products. In some high-end petroleum products, various antioxidants and additives are also added to meet the performance and quality requirements of the product.
Food industry
(1) Edible oil antioxidant
Antioxidant 264 is an effective antioxidant for edible oils and fats, which can prevent oils and fats from becoming rancid due to oxidation and extend their shelf life. During the storage and processing of oils and fats, they are affected by factors such as heat, oxygen, and light, leading to oxidation reactions and the formation of peroxides, aldehydes, ketones, and other substances. This can cause oils and fats to produce odors, change color, and reduce their nutritional value. Antioxidant 264 can inhibit the oxidation reaction of oil and maintain the quality of oil by capturing free radicals and other methods. According to Chinese regulations, antioxidant 264 can be used for edible oils, fried foods, biscuits, instant noodles, instant rice, canned nuts, dried fish products, and cured meat products, with a dosage of 0.2g/kg.
(2) Antioxidants in Foods Containing Animal and Plant Oils and Fats
In addition to edible oils and fats, antioxidant 264 is also widely used in foods containing animal and vegetable oils and fats, such as oils, butter, dried fish and shellfish products, salted fish and shellfish products, frozen whale meat products, etc., with a dosage of less than 0.2 grams per kilogram; The dosage in chewing gum is below 0.75 grams per kilogram. It can prevent food from spoiling due to oil oxidation and maintain the taste and nutritional value of the food. For example, in some fried foods, antioxidant 264 can prevent oil oxidation and spoilage, keeping the food crispy and with a good color.
(3) Application in food processing technology
The use of Butylated hydroxyluene(BHT) includes immersion method, direct mixing method, mixing method dissolved in ethanol and spray method. In the process of food processing, appropriate addition methods can be selected according to different types of food and processing techniques. For example, in some solid foods, antioxidant 264 can be added to the food using impregnation or direct mixing methods; In some liquid food, it can be added by mixing method or spray method after dissolving in ethanol.
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