2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol
2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol
CAS: 3896-11-5
Molecular Formula: C17H18ClN3O
2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol - Names and Identifiers
| Name | 2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol |
| Synonyms | UV 326 UV-326 Bumetrizole TINUVIN 326 BUMETRIZOLE LABOTEST-BB LT00138024 ULTRAVIOLET ABSORBENT UV-326 ULTRA-VIOLET ABSORBER UV-326 Ultraviolet absorbent UV-326 2-T-BUTYL-6-(5-CHLORO-2 H-BENZOTRIAZOL-2-YL)-4-METHYLPHENOL 2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol 2-(5-chloro-2h-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methyl-pheno Phenol, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methyl- |
| CAS | 3896-11-5 |
| EINECS | 223-445-4 |
| InChI | InChI=1/C17H18ClN3O/c1-10-7-12(17(2,3)4)16(22)15(8-10)21-19-13-6-5-11(18)9-14(13)20-21/h5-9,22H,1-4H3 |
| InChIKey | OCWYEMOEOGEQAN-UHFFFAOYSA-N |
2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol - Physico-chemical Properties
| Molecular Formula | C17H18ClN3O |
| Molar Mass | 315.8 |
| Density | 1.26±0.1 g/cm3(Predicted) |
| Melting Point | 144-147°C(lit.) |
| Boling Point | 460.4±55.0 °C(Predicted) |
| Flash Point | 232.3°C |
| Water Solubility | 4μg/L at 20℃ |
| Solubility | Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) |
| Vapor Presure | 0Pa at 20℃ |
| Appearance | yellowish-like powder |
| Color | Pale Yellow to Light Yellow |
| pKa | 9.31±0.48(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.628 |
| MDL | MFCD00059707 |
| Physical and Chemical Properties | Light yellow crystalline powder, density 1.32g/cm3, melting point 137~141 ℃, boiling point 460.4 ℃, flash point 232.3 ℃. Slightly soluble in benzene, toluene, and styrene, insoluble in water. |
| Use | Mainly used in polyvinyl chloride, polystyrene, unsaturated resin, polycarbonate, polymethyl methacrylate, polyethylene, ABS resin, epoxy resin |
2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R53 - May cause long-term adverse effects in the aquatic environment |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| WGK Germany | 1 |
| HS Code | 29339900 |
2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol - safety
Open Data Verified Data
This product is non-toxic, non flammable, non corrosive, and stored and transported under dry, ventilated, and low temperature conditions.
Last Update：2023-10-13 10:15:49
2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol - Preparation method
Open Data Verified Data
1. Preparation of 2-Nitro-5-Chlorodiazobenzene Hydrochloride
Add 2-nitro-5-chloroaniline to the reactor, then add an appropriate amount of hydrochloric acid, stir and dissolve. Cool the system to a temperature of 0-5 ℃, slowly add 25% -30% sodium nitrite solution for diazotization reaction. The product is 2-nitro-5-chlorodiazobenzene hydrochloride.
2. Coupling reaction
Add 50% caustic soda solution and 4-methyl-2-tert-butylphenol to the reactor, stir and dissolve to obtain 4-methyl-2-tert-butylphenol sodium. Afterwards, the prepared 2-nitro-5-chlorodiazobenzene hydrochloride solution was added to this reactor. Control the temperature to around 15 ℃, add sodium carbonate solution under stirring, and maintain it at 15 ℃ for coupling reaction. When the alkalinity of the material in the kettle no longer decreases, stop the reaction and filter to obtain azo compounds.
3. Preparation of 2- (2 '- hydroxy-3' - tert butyl-5 '- methylphenyl) -5-chlorobenzotriazole
Add the azo compound prepared above to the reaction kettle, then add an appropriate amount of 50% sodium hydroxide solution, and stir evenly. Slowly add an appropriate amount of zinc powder under stirring, control the temperature to 40-45 ℃, and proceed with the reduction reaction. After the reaction is completed, filter to remove solid substances such as zinc powder, and then feed the filtrate into the reaction kettle. Stir at room temperature while adding hydrochloric acid for acidification and filtration to obtain the crude product.
4. Product Refinement
Dissolve the crude product prepared above in alkaline solution, and the dissolution process can be heated appropriately. Then, filter the filtrate while it is hot and undergo acidification, crystallization, filtration, water washing, drying, gasoline washing, activated carbon decolorization, filtration, cooling crystallization, and filtration to obtain a high purity finished product.
Last Update：2024-01-02 23:10:35
2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | ultraviolet absorber refers to a preparation that can prevent a large amount of ultraviolet rays from passing through. ultraviolet absorber should have the following conditions: good thermal stability, no change due to heat even during processing, and low thermal volatility; It can strongly absorb ultraviolet rays (especially the wavelength is 290-400nm) and has good chemical stability, it does not react adversely with the material components in the product; it has good miscibility, can be evenly dispersed in the material, does not spray frost, does not exude; the absorbent itself has good photochemical stability, does not decompose, and does not change color; colorless, Non-toxic and odorless; resistant to immersion; cheap and easy to obtain. Ultraviolet absorbers can be divided into the following categories according to their chemical structure: salicylates, phenylketones, benzotriazoles, substituted acrylonitrile, triazines and other categories. The fabric with UV absorber can obtain good UV blocking effect. It can reduce fading and enhance the solar fastness of polyester disperse dyes. Ultraviolet absorber UV-326 is one of them. |
| characteristics | ultraviolet absorber is UV-326 light yellow crystalline powder with melting point of 137-141 ℃, soluble in styrene, benzene, toluene and other solvents, can effectively absorb 270-380nm ultraviolet light. It has low volatility and good compatibility with resin. It is mainly used for polyolefin, polychloroethylene olefin, unsaturated polyester, polyamide, polyurethane, epoxy resin, ABS resin and cellulose resin. It is suitable for natural rubber and synthetic rubber. |
| Application | The ultraviolet absorber is UV-326 benzotriazole light stabilizer, 2 '-(2'-hydroxy -3 '-tert-butyl -5'-methyl phenyl)-5-chlorobenzotriazole. UV-326 can absorb 280-370nm ultraviolet rays, has good stability, low toxicity, and has no irritation to the human body. It is widely used in coatings, synthetic rubber, synthetic fibers, photosensitive materials, etc., which can effectively improve the light resistance of these materials and reduce The phenomenon of yellowing and aging caused by the excitation of ultraviolet rays in sunlight. |
| preparation | diazotization reaction: weigh 6g of 98wt%H2SO4, 50ml of water and 0.03mol of p-chloro-o-nitroaniline into a reaction kettle, slowly add 15g of 20wt%NaNO2 solution dropwise when cooled to 5 ℃, and continue stirring for 1h until the reaction is over. Add urea to decompose residual nitrous acid and filter to remove slag. Coupling reaction: weigh 0.03mol 2-tert-butyl p-cresol, 50mL water and 0.1g sodium dodecyl benzene sulfonate into the reaction kettle and stir to form a uniform white emulsion. The pH was adjusted to 7-9, and the diazonium salt solution was added dropwise within 2 hours under this weak alkali condition. Filtering, washing, drying and weighing after the reaction. Glucose reduction reaction: weigh the product obtained by 0.015mol diazo coupling reaction and add 10g NaOH solution (20wt%) into the reaction kettle. When the temperature is 50 ℃, slowly add 100ml of 30wt% glucose solution dropwise, continue the reaction for 1h, filter and drain after cooling to obtain nitrogen oxide intermediate. Reduction reaction of zinc powder: 17mL chlorobenzene and 42 g14wt%H2SO4 were added to the above nitrogen oxides and heated to 90 ℃. Add 1.1g zinc powder in batches within 2h, add activated carbon after the reaction, stir for 0.5h, filter while hot, layer the filtrate, wash the oil layer to neutral, and evaporate the solvent to obtain the target product. The analysis results show that the yield of the product is 90.9% and the purity is 99.3%. |
| UV absorber UV-326 | UV absorber UV-326 as a light stabilizer, is a more representative of benzotriazole UV absorbers. Its advantages are stable performance, low toxicity, and strong ultraviolet absorption. It can be widely used in photosensitive materials such as color film, color film, color photo paper and polymer, outer protective coating and many fields. It can effectively absorb ultraviolet light with a wavelength of 270-380nm. It has a wide range of non-food direct contact permits in polyolefins. It has low volatility at high temperatures and has high resistance to thermal degradation. Therefore, it can be used in polyolefin The decomposition loss is reduced during polymerization and film compression molding, and ultraviolet protection is used in polyester resin. This product will not form metal non-ferrous salts during the heating process of the resin. |
| ultraviolet absorber | ultraviolet absorber is a light stabilizer, which can absorb the ultraviolet part of sunlight and fluorescent light source without changing itself. The plastic is protected from photo-oxidative degradation caused by ultraviolet radiation, thus greatly prolonging the service life of the product. Plastics and other polymer materials under sunlight and fluorescence, due to the action of ultraviolet rays, produce an automatic oxidation reaction, which leads to the degradation of the polymer and deterioration of the appearance and mechanical properties. After adding the ultraviolet absorber, the high-energy ultraviolet rays can be selectively absorbed, so that they can be turned into harmless energy and released or consumed. Different types of polymers make the ultraviolet wavelengths deteriorated different. Different ultraviolet absorbers can absorb ultraviolet rays of different wavelengths. When using, ultraviolet absorbers should be selected according to the type of polymer. The ultraviolet absorber should meet the following conditions: ①It can strongly absorb ultraviolet rays (especially the wavelength is 290-400nm); ②It has good thermal stability, will not change due to heat even during processing, and has low thermal volatility; ③Chemical stability Good, no adverse reaction with the material components in the product; ④Good miscibility, can be evenly dispersed in the material, no frost, no exudation; ⑤ The absorbent itself has good photochemical stability, does not decompose, and does not change color; ⑥ Colorless, non-toxic and odorless; ⑦ Immersion resistance; ⑧ Cheap and easy to obtain. Ultraviolet absorbers can be divided into the following categories according to their chemical structure: salicylates, phenylketones, benzotriazoles, substituted acrylonitrile, triazines and other categories. UV absorbers are used in plastics, coatings, dyes, car windshields, cosmetics, medicines, sunscreens, etc. |
| common ultraviolet absorber | salicyl ester phenyl ester (composition: phenyl o-hydroxybenzoate), ultraviolet absorber UV-P (composition: o-nitroaniline, p-cresol reaction product), ultraviolet absorber UV-O (composition: 2, 4-dihydroxybenzophenone), ultraviolet absorber UV-9 (composition: 2-hydroxy-4-methoxybenzophenone), ultraviolet absorber UV-531 (composition: 2-Hydroxy-4-nooxybenzophenone), UV absorber UVP-327 (composition: 2-(2 '-hydroxy -3',5 '-di-tert-phenyl)-5-chlorinated benzotriazole), UV absorber RMB (composition: resorcinol monobenzoate), light stabilizer AM-101 (composition: 2,2'-thiobis (4-tert-octylphenoxy) nickel), light stabilizer GW-540 (composition: tris (1,2,2,6, 6-pentamepidinyl) phosphite), light stabilizer 744 (composition: 4-benzoyloxy-2, 2,6, 6-tetramethylpiperidine), light stabilizer HPT (composition: hexamethylphosphide) |
| Production and application of ultraviolet absorber UV-326 | The production process of ultraviolet absorber UV-326 is to combine 4-chloro-2-nitroaniline (1) with sodium nitrite (2) and sulfuric acid diazotization with 2-terbutyl-4-methylphenol (3) for coupling reaction, the molar ratio of 2-nitro -4-chloro -2 ′-hydroxy -3 ′-tert-butyl -5 ′-methyl azobenzene (4).(1), (2), (3) is: 1:1.04:1.18. Reduce (4) to 2-(2 '-hydroxy -3'-terbutyl-5 '-methylphenyl)-5-chlorobenzotriazole nitrogen oxide (5) with sodium sulfide, finally, the final product 2-(2'-hydroxy -3 '-terbutyl-5'-methylphenyl)-5-chlorobenzotriazole (6)(UV-326) was made by reducing (5) with zinc powder. UV-326 is an excellent light stabilizer for polyolefin, ABS, polyester and other resins, and has synergistic effect with hindered amine light stabilizer (HALS). Author: Ding Zhu Ming Zhuming Author: Tianjin Institute of Synthetic Materials Industry, Tianjin, 300200 |
| inorganic ultraviolet absorber | light stabilizers used in history can be roughly divided into 4 categories, namely ultraviolet absorber, quenching agent, free radical spreading agent and light shielding agent. From the principle of action, it mainly works in three directions. One is to prevent ultraviolet rays from entering the product and resist the enemy outside the door. However, the shielding agent has no choice for light shielding. As a result, the product is opaque. The second is to capture free radicals caused by ultraviolet rays entering the polymer to prevent free radicals from further triggering other molecular breakage. In essence, it is to protect the overall integrity of the product at the cost of very few molecular bond breakage. Fading is easy to occur when using UV-sensitive pigments. Third, it absorbs the energy of ultraviolet rays and converts it into heat energy for emission, which is a good method. At present, the international concept of green consumption is increasingly strengthened, requiring products to have a long service life to protect limited resources. The toxicity of the product has attracted more attention. In this context, inorganic nano-ultraviolet absorbers came into being. Nanomaterials mean that the size of the material is at least one-dimensional between 1-100nm. At present, the powders used as ultraviolet absorbers are basically spherical particles. The particle size is equivalent to the ultraviolet wavelength, and the ultraviolet light wave undergoes strong reflection on the ion surface. This phenomenon is called the small size effect of nanomaterials. Under the effect of small size, nanomaterials can strongly shield ultraviolet rays, and the wavelength of visible light is much larger than the particle size. They will cause light diffraction through the particles, making nanomaterials have high permeability to visible light while shielding ultraviolet rays. Generally speaking, the outstanding advantages of inorganic ultraviolet absorber are: 1. High ultraviolet shielding efficiency and good visible light transmission filtration. 2. Excellent stability, long-term function, long-term maintenance of polymer products bright appearance, prolong the life of polymer products. 3. The products currently developed are basically non-toxic and have a wide range of applications. 4. As the biological, optical, electrical and magnetic properties of the particles have changed greatly after reaching the nanometer level, this will bring about the optimization of the mechanical properties of polymer materials, making it possible to produce functional materials. At present, high-strength plastics have been produced by using nanomaterials, and sterilization and self-cleaning functional coatings have been produced by using the high surface activity of nanomaterials. |
| use | mainly used for polyvinyl chloride, polystyrene, unsaturated resin, polycarbonate, polymethyl methacrylate, polyethylene, ABS resin, epoxy resin, etc. |
Last Update：2024-04-09 21:01:54
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