2,4-二羟基二苯甲酮
2,4-Dihydroxybenzophenone
CAS: 131-56-6
Molecular Formula: C13H10O3
2,4-二羟基二苯甲酮 - Names and Identifiers
| Name | 2,4-Dihydroxybenzophenone |
| Synonyms | BP-1 UV-0 Benzophenone-1 Benzoresorcinol Resbenzophenone 4-benzoylresorcinol Ultraviolet absorber UV-0 2,4-Dihydroxybenzophenone Ultraviolet absorbent UV-0 2,4-Dihydroxy Benzophenone (2,4-dihydroxyphenyl)phenyl-methanone 2,4-Dihydroxybenzophenone(Benzophenone-1) |
| CAS | 131-56-6 |
| EINECS | 205-029-4 |
| InChI | InChI=1/C13H10O3/c14-10-6-7-11(12(15)8-10)13(16)9-4-2-1-3-5-9/h1-8,14-15H |
| InChIKey | ZXDDPOHVAMWLBH-UHFFFAOYSA-N |
2,4-二羟基二苯甲酮 - Physico-chemical Properties
| Molecular Formula | C13H10O3 |
| Molar Mass | 214.22 |
| Density | 1.302g/cm3 |
| Melting Point | 142-147℃ |
| Boling Point | 409°C at 760 mmHg |
| Flash Point | 215.3°C |
| Water Solubility | insoluble |
| Solubility | Insoluble in water, soluble in ethanol, ether, glacial acetic acid, slightly soluble in cold benzene, soluble in methanol, isopropanol, acetone and ethyl acetate. |
| Vapor Presure | 2.84E-07mmHg at 25°C |
| Appearance | Form Crystalline Powder, color Yellow |
| pKa | 7.72±0.35(Predicted) |
| PH | 5 (10g/l, H2O, 20℃)(slurry) |
| Storage Condition | Store below +30°C. |
| Refractive Index | 1.647 |
| MDL | MFCD00002277 |
| Physical and Chemical Properties | Melting point 142-147°C boiling point 194°C (1 mmHg) flash point 125°C water-soluble insoluble |
| Use | Mainly used in plastic as a light stabilizer, can effectively protect the organic glass and cloth, to prevent information and other deterioration due to light, also used as an intermediate for the synthesis of other UV absorbers. |
2,4-二羟基二苯甲酮 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 2 |
| RTECS | DJ0700000 |
| TSCA | Yes |
| HS Code | 29145000 |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg |
2,4-二羟基二苯甲酮 - Upstream Downstream Industry
2,4-二羟基二苯甲酮 - Nature
Open Data Unverified Data
| Merck | 14,1106 |
| BRN | 1311566 |
| NIST chemical information | Methanone, (2,4-dihydroxyphenyl)phenyl-(131-56-6) |
| EPA chemical information | Methanone, (2,4-dihydroxyphenyl)phenyl- (131-56-6) |
Last Update：2024-04-09 19:43:38
2,4-二羟基二苯甲酮 - Uses and synthesis methods
Open Data Unverified Data
overview
Ultraviolet absorber is a light stabilizer, which can absorb the ultraviolet part of sunlight and fluorescent light source without changing itself. 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 the deterioration of the appearance and mechanical properties. After adding the ultraviolet absorber, the high-energy ultraviolet rays can be selectively absorbed, so that it becomes harmless energy and is released or consumed. Due to the different types of polymers, the ultraviolet wavelengths that deteriorate are also different. Different ultraviolet absorbers can absorb ultraviolet rays of different wavelengths. When using, ultraviolet absorbers should be selected according to the types of polymers.
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; ③Good chemical stability, 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 resistant to immersion; ⑧ Cheap and easy to obtain; ⑨ Insoluble or insoluble in water.
Ultraviolet absorbers are used in plastics, coatings, dyes, car windshields, cosmetics, medicines, sunscreens, etc.
main features
ultraviolet absorber UVA is a wide-band oil-soluble ultraviolet absorber. this product has strong absorption of ultraviolet rays in the whole UVA band (320-400nm) with a maximum absorption peak of 354nm. It is currently one of the best UV absorbers in UVA band. Compared with UV1789 (Avobenzone), it has more excellent light stability. Avobenzone is limited by its own structure, and its ultraviolet absorption performance will be greatly reduced under ultraviolet light irradiation. Therefore, MC80 (octyl methoxycinnamate) and HMS (humosyl) have to be used in the application process.) Wait for protection. The molecular structure of the ultraviolet absorber UVA has good resonance and hydrogen ion transfer effects. The molecular structure will not be destroyed during the absorption of ultraviolet rays by the absorber, so it can play a long-term protection.
UV absorber UV-P
Ingredients: reaction products of o-nitroaniline and p-cresol
performance and use: colorless or light yellow crystal in appearance. Soluble in gasoline, benzene, acetone and other organic solvents. The solubility in water is extremely small and will not be decomposed by concentrated alkali and concentrated acid. It can be ionized with heavy metals to synthesize salts. It can absorb ultraviolet rays with wavelengths of 270 ~ 280nm. Melting point 130~131 ℃.
UV absorber UV-P are mainly used in polyester, chlorine-containing polyester, vinegar fiber, polyvinyl chloride, polystyrene, plexiglass, polyacrylonitrile and other resins. The stability in transparent products is better than that in colored products. The dosage in the product is 0.%~ 0.5%.
UV absorber UV-9
Ingredients: 2-hydroxy-4-methoxybenzophenone
properties and uses: this product is light yellow or white crystalline powder. Density 1.324g/cm3. Melting point 62~66 ℃. Boiling point 150~160 ℃(0.67kPa) and 220 ℃(2.4kPa). Soluble in most organic solvents such as acetone, ketone, benzene, methanol, ethyl acetate, methyl ethyl ketone and ethanol, and insoluble in water. The solubility of this product in some solvents (g/100g solvent, 25 ℃) is solvent benzene 56.2, n-hexane 4.3, ethanol (95%)5.8, carbon tetrachloride 34.5, styrene 51.2, DOP18.7.
ultraviolet absorber is UV-9 suitable for polyvinyl chloride, polyvinylidene chloride, polymethyl methacrylate, unsaturated polyester, ABS resin, cellulose resin and other plastics. the maximum absorption wavelength range is 28 ~ 340nm, the general dosage is 0.1% ~ 1.5%, the thermal stability is good, and it is not decomposed at 200 ℃. This product hardly absorbs visible light, so it is suitable for light-colored transparent products. This product can also be used in paint and synthetic rubber.
safety precautions: Japan and Italy stipulate that the maximum dosage of this product shall not exceed 0.3% when it is used in food contact products.
UV absorber UVP-327
Ingredients: 2-(2 '-hydroxy -3',5 '-di-tert-phenyl)-5-benzotriazole chloride
performance and application: the characteristics and application of ultraviolet absorber UVP-327 are similar to those of UV-326. it can strongly absorb ultraviolet rays with a wavelength of 270 ~ 380nm, with good chemical stability and minimal volatility. Good compatibility with polyolefin. Especially suitable for polyethylene and polypropylene. In addition, it can also be used for polyvinyl chloride, polymethyl methacrylate, polyoxymethylene, polyurethane, unsaturated polyester, ABS resin, epoxy resin and cellulose resin. This product has excellent heat sublimation resistance, washing resistance, gas fading resistance and mechanical properties retention. Combined with antioxidants is a significant synergistic effect. To improve the thermal oxygen stability of the product. The general dosage of this product in plastic is 1% ~ 3%.
safety precautions: this product has low toxicity. Japan, the United States, France and Italy license this product to be used in polyolefin plastics contacting food. the maximum dosage is 0.5%, and it is used in other plastics contacting food. the maximum dosage stipulated by Italy is 0.2%, and that is 0.5% in Japan and France.
Preparation
1) Preparation of 2-(4-N, N-diethylamino-2-hydroxybenzoyl) benzoic acid
99g(0.60mol) 3-diethylaminophenol, 93.2g(0.63mol) phthalic anhydride and 460ml toluene were introduced into a 500ml four-neck flask equipped with Teflon agitator, thermometer and reflux condenser under nitrogen atmosphere, and heated to reflux temperature. After 2 hours of reaction, a total of 300g of toluene was distilled within 30 minutes, and then the mixture was stirred under reflux for 3 hours. The mixture was cooled to room temperature and aspirated and filtered. The filter cake was washed sequentially with 90ml toluene and 2 × 90ml hexanol. The hexanol-moistened acid can be used directly in the second step. Yield: 169g(90%) pink 2-(diethylamino-2-hydroxybenzoyl) benzoic acid.
2) Preparation of 2-(4-N, N-diethylamino-2-hydroxybenzoyl) n-hexyl benzoate (UV absorber UVA)
313g(1.0mol) hexanol wetted 2-(4-diethylamino-2-hydroxybenzoyl) benzoic acid (in 100%) and 750ml n-hexanol are introduced into a 1-liter shallow flange flask equipped with anchor stirrer, nitrogen conduit, thermocouple and water separator, mixed with 53g(519mmol)96% concentration sulfuric acid and heated to an internal temperature of 105-110°C. After heating, the water formed by the reaction was evaporated azeotropic for 6-8 hours at an internal temperature of 105-110°C and a pressure of about 200 mbar. After cooling to about 70°C, the mixture was mixed with 830ml of water and neutralized with a 25% concentration of NaOH solution at a temperature of 52-58°C. The aqueous phase was separated and the organic phase was extracted with 500ml of water (temperature: 52-58°C). The aqueous phase is separated, the organic phase is cooled to 20°C and the crystallization of the ester is awaited. After holding for 1 hour to mature the in-situ produced seed material, the mixture was cooled to 0-5°C at 5 K/h, stirred at this temperature for 2 hours and filtered. The filter cake was washed with 2 × 85ml cold hexanol. The crude pink product UV absorber UVA(407g), moist with hexanol, was thoroughly aspirated and purified by adsorption on activated carbon.
use
Used as an ultraviolet absorber, 2-hydroxy-4-methoxybenzophenone (UV-9), 2-hydroxy-4-nooxybenzophenone (UV-531) derived from this product Benzophenone, as well as other monohydroxy, dihydroxy, trihydroxy, and tetrahydroxy compounds are the most widely used absorption light stabilizers. It can absorb 290-400 nanometers of ultraviolet light, and has good compatibility with most synthetic resins, and is widely used in polymer materials. 2, 4-dihydroxybenzophenone is suitable for polyvinyl chloride, polystyrene, epoxy resin, cellulose resin, unsaturated polyester, paint and synthetic rubber. The maximum absorption wavelength range is 280-340 nm, and the general dosage is 0.1-1%. But the light stabilization effect of this product is not outstanding. This product is oral LD50 ash 8600 mg/kg to rats and 2336 mg/kg to mice.
Suitable for polyolefins, polyvinyl chloride and polystyrene, etc.
production method
There are four main methods. 1. Resorcinol and benzoyl chloride are used as raw materials. 2. Resorcinol and trichlorotoluene are used as raw materials. 3. Benzoic acid and resorcinol are used as raw materials. 4.2-(2 ',4'-dihydroxybenzoyl) benzoic acid is prepared by condensation of phthalic anhydride and resorcinol, and then 2,4-dihydroxybenzophenone is obtained by dehydroxylation reaction.
Last Update：2024-04-09 19:43:38
2,4-二羟基二苯甲酮 - Security information
Open Data Unverified Data
| Hazard Note | Irritant |
| toxic substance data | 131-56-6(Hazardous Substances Data) |
Last Update：2024-04-09 19:43:38
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View History
2,4-二羟基二苯甲酮
ALPHA-CYANO-(3-HYDROXY-4-NITRO)CINNAMONITRILE
4-Boc-3-cyanomorpholine
2-Methylpropyl 2-aminobenzoate
2-氰基-6-氟苯基硼酸
2-AMINO-5-METHYL-4-(4-NITROPHENYL)THIOPHENE-3-CARBONITRILE
Acetic acid, reaction products with formaldehyde and pyrolized 2,6,6-trimethylbicyclo[3.1.1]heptane
5-溴-4-嘧啶乙酸乙酯
4-4-氟苯基-3-胺基硫脲
Phthalyl-DL-Glutamic Acid
ALPHA-CYANO-(3-HYDROXY-4-NITRO)CINNAMONITRILE
4-Boc-3-cyanomorpholine
2-Methylpropyl 2-aminobenzoate
2-氰基-6-氟苯基硼酸
2-AMINO-5-METHYL-4-(4-NITROPHENYL)THIOPHENE-3-CARBONITRILE
Acetic acid, reaction products with formaldehyde and pyrolized 2,6,6-trimethylbicyclo[3.1.1]heptane
5-溴-4-嘧啶乙酸乙酯
4-4-氟苯基-3-胺基硫脲
Phthalyl-DL-Glutamic Acid
Raw Materials for 2,4-二羟基二苯甲酮
Downstream Products for 2,4-二羟基二苯甲酮
Fluotrimazol
Octabenzone
2-METHYL-ACRYLIC ACID-2-(4-BENZOYL-3-HYDROXY-PHENOXY)-ETHYL ESTER
2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate
Octabenzone
2-METHYL-ACRYLIC ACID-2-(4-BENZOYL-3-HYDROXY-PHENOXY)-ETHYL ESTER
2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate