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BENZOPHENONE 1 = 2, 4-DIHYDROXYBENZOPHENONE
CAS Number: 131-56-6
Chemical Formula: C13H10O3
Molecular Weight: 214.217
Benzophenone-1 is an off white or light yellow crystalline powder with a melting point of 142-146 min.
Is a light stabilizer agent, applicable to polyolefine, poyvinyl chlornamee, polystyrene etc. and as the intermediate of UV-absorbing agents as well.
Many 7-free, 10-free and ‘non-toxic’ nail polish brands still use Benzophenone-1 in their formulas.
Benzophenone -1 is a UV blocker that is used in sunscreens as well as cosmetics to stop discolouration of products.
Just to be clear, there are some studies that show Benzophenone-1 is relatively harmless in small quantities, however Benzophenone-1 has also been linked to breast cancer, ovarian cancer, prostate cancer, and has been found in human placental tissue.
Benzophenone-1 powder polymer additive applicable to polyolefine, poyvinyl chlornamee, polystyrene etc as a stabilizer with the incorporation of 0.1% to0.5% (based on polymer weight) required.
Benzophenone-1, -3, -4, -5, -9 and-11 are compounds made from 2-hydroxybenzophenone.
These compounds are powders.
In cosmetics and personal care products, Benzophenone-1 and Benzophenone-3 are used mostly in the formulation of nail polishes and enamels.
These Benzophenone ingredients are also used in bath products, makeup products, hair products, sunscreens and skin care products.
In cosmetics and personal care products, Benzophenone-1 and Benzophenone-3 are used mostly in the formulation of nail polishes and enamels.
These Benzophenone ingredients are also used in bath products, makeup products, hair products, sunscreens and skin care products.
The Food and Drug Administration (FDA) has approved the use of Benzophenone-3 and Benzophenone-4 as safe and effective, over-the-counter (OTC) sunscreen ingredients.
When used as a sunscreen ingredient in the United States, Benzophenone-3 is called Oxybenzone, and may be used at concentrations up to 6%, and Benzophenone-4 is called Sulisobenzone, and may be used at concentrations up to 10%.
Benzophenone ingredients absorb and dissipate UV radiation, which serves to protect cosmetics and personal care products.
As part of sunscreen products, which are OTC drugs in the United States, Benzophenone-3 (Oxybenzone) and Benzophenone-4 (Sulisobenzone) protect the skin from the harmful effects of the sun.
Exposing unprotected skin to UV light (primarily in the UV-B range) can result in sunburn and can promote premature aging of the skin and skin cancer.
Elimination of Benzophenone-1 in Water by High-Frequency Ultrasound:
Benzophenone-1 (BP1) has been classified as a potential endocrine disruptor due to its reported negative effect on different living beings.
In addition, Benzophenone-1 presence in different water bodies has been detected.
In this way, the ultrasonic removal of BP1 was studied considering the effects of the frequency, the power density, and the pollutant initial concentration.
In general, results indicated that very high values of frequency and power density inhibit the pollutant removal.
Two kinetic models were evaluated to describe BP1 initial degradation rate considering that the pollutant elimination could take place in the bulk solution and the bubble–liquid interfacial region.
Experiments carried out under the presence of some radical scavengers showed that BP1 removal occurs mainly over the generated cavitation bubbles surface, and that HO• radicals could be the main species responsible for the pollutant elimination.
Five degradation byproducts were identified, and a plausible reaction route was proposed.
Finally, samples’ toxicity was analyzed considering changes in the Vibrio fischeri bacteria luminescence.
Why is Benzophenone-1 used in cosmetics and personal care products?
Benzophenone-1, Benzophenone-3, Benzophenone-4, Benzophenone-5, Benzophenone-9 and Benzophenone-11 protect cosmetics and personal care products from deterioration by absorbing, reflecting, or scattering UV rays.
When used as sunscreen ingredients, Benzophenone-3 and Benzophenone-4 protect the skin from UV rays.
Benzophenone-1 - Uses and synthesis methods:
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 Benzophenone-1 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: It can strongly absorb ultraviolet rays (especially the wavelength is 290-400nm);
Benzophenone-1 has good thermal stability, will not change due to heat even during processing, and has low thermal volatility;
Good chemical stability, no adverse reaction with the material components in the product;
Good miscibility, can be evenly dispersed in the material, no frost, no exudation; 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;
Insoluble or insoluble in water.
Ultraviolet absorbers are used in plastics, coatings, dyes, car windshields, cosmetics, medicines, sunscreens, etc.
Main Features of Benzophenone 1:
Ultraviolet absorber UVA is a wide-band oil-soluble ultraviolet absorber.
Benzophenone-1 has strong absorption of ultraviolet rays in the whole UVA band (320-400nm) with a maximum absorption peak of 354nm.
Benzophenone-1 is currently one of the best UV absorbers in UVA band.
Compared with UV1789 (Avobenzone), Benzophenone-1 has more excellent light stability.
Avobenzone is limited by Benzophenone-1 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 Benzophenone-1 can play a long-term protection.
UV absorber UV-P
Ingredients: reaction products of o-nitroaniline and p-cresol
Performance And Use of Benzophenone 1:
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.
Benzophenone-1 can be ionized with heavy metals to synthesize salts.
Benzophenone-1 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 of Benzophenone 1:
Benzophenone-1 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 Benzophenone-1 is not decomposed at 200 ℃.
Benzophenone-1 hardly absorbs visible light, so it is suitable for light-colored transparent products.
Benzophenone-1 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 Benzophenone-1 is used in food contact products.
Performance And Application:
The characteristics and application of ultraviolet absorber UVP-327 are similar to those of UV-326.
Benzophenone-1 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, Benzophenone-1 can also be used for polyvinyl chloride, polymethyl methacrylate, polyoxymethylene, polyurethane, unsaturated polyester, ABS resin, epoxy resin and cellulose resin.
Benzophenone-1 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:
Benzophenone-1 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 Benzophenone-1 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:
Benzophenone-1 is 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.
Benzophenone-1 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.
Benzophenone-1 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.
Uses of Benzophenone 1:
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.
Physico-chemical Properties of Benzophenone 1:
Molecular Formula: C13H10O3
Molar Mass: 214.217
Density: 1.302g/cm3
Melting Point: 142-147℃
Boling Point: 409°C at 760 mmHg
Flash Point: 215.3°C
Solubility: insoluble
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
Specification of Benzophenone 1:
Appearance: Off white or light yellow crystalline powder
Assay: 99.0%min
Melting Point: 142.0-146.0℃
Gardner Color(2%，w/v，in methanol）: 3.0 max
Specific Extinction(1%,1cm) E290: 630 min
Loss on drying: 0.2% max
Heavy Metals: 5ppm max
Burnt Residue: 0.5% max
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
Compatible Polymers & Resins: Polyvinyl Chloride (PVC), Polystyrenes (PS)
Function: UV Absorber
Synonyms of Benzophenone 1:
Benzophenone-1
Benzophenone 1
benzofenon 1
benzo fenon 1
benzofenone 1
benzofenon1
benzo phenone 1
benzophenone
benzophenon
benzophenon 1
benzofenon 1
benzofenon bir
benzo fenon bir
benzo fenon 1
benzofenon-1
aduvex 12
CAS Number: 131-56-6
advastab 48
benzophenone, 2,4-dihydroxy-
4- benzoyl resorcinol
4- benzoylresorcinol
dastib 263
2,4- dihydroxy benzophenone
2,4- dihydroxy-benzophenone
(2,4- dihydroxy-phenyl)-phenyl-methanone
2,4- dihydroxybenzophenone
2,4- dihydroxyphenyl phenyl ketone
(2,4- dihydroxyphenyl)(phenyl)methanone
(2,4- dihydroxyphenyl)phenylmethanone
eastman Inhibitor DHPB
inhibitor DHBP
methanone, (2,4-dihydroxyphenyl)phenyl-
quinsorb 010
seesorb 100
sumisorb 100
syntase 100
ultrafast 800
uvinol 400
uvinul 400
uvistat 12
viosorb 100
inhibitor DHBP
methanone, (2,4-dihydroxyphenyl)phenyl-
quinsorb 010
seesorb 100
sumisorb 100
syntase 100
Benzoresorcinol
4-benzoylresorcinol
BP-1
UV-0
Benzophenone-1
Ultraviolet absorber UV-0
2,4-Dihydroxy Benzophenone
Ultraviolet absorbent UV-0
2,4-Dihydroxybenzophenone(Benzophenone-1)
(2,4-dihydroxyphenyl)phenyl-methanone
Resbenzophenone
