Hydroxybiphenyl
O-Phenyl phenol
CAS: 90-43-7
Molecular Formula: C12H10O
Hydroxybiphenyl - Names and Identifiers
| Name | O-Phenyl phenol |
| Synonyms | OPP Xenol Torsite o-Xonal Remol TRF FEMA 3959 Orthoxenol Dowicide 1 2-Biphenylol 2-DIPHENYLOL BIPHENYLOL-2 Tumescal OPE DOWICIDE 1(R) Biphenyl-2-ol BIPHENYL-2-OL AKOS BAR-1742 2-PHENYLPHENOL 2-Phenylphenol Hydroxdiphenyl o-phenylphenol O-Phenyl phenol Hydroxybiphenyl 2-Hydroxybiphenyl 2-HYDROXYDIPHENYL Preventol O extra O-HYDROXIDIPHENYL 1,1'-Biphenyl-2-ol Ortho Phenylphenol [1,1'-BIPHENYL]-2-OL orthohydroxydipbenyl Hydroxy-2-phenylbenzene HYDROXY-(2-PHENYL)BENZENE |
| CAS | 90-43-7 |
| EINECS | 201-993-5 |
| InChIKey | LLEMOWNGBBNAJR-UHFFFAOYSA-N |
Hydroxybiphenyl - Physico-chemical Properties
| Molecular Formula | C12H10O |
| Molar Mass | 170.21 |
| Density | 1.21 |
| Melting Point | 57-59°C(lit.) |
| Boling Point | 282°C(lit.) |
| Flash Point | 255°F |
| JECFA Number | 735 |
| Water Solubility | 0.7 g/L (20 ºC) |
| Solubility | Soluble in ethanol, acetone, benzene,sodium hydroxide, chloroform, acetonitrile, toluene, hexane, ligroin, ethyl ether, pyridine, ethylene glycol, isopropanol, glycol ethers and polyglycols. |
| Vapor Presure | 7 mm Hg ( 140 °C) |
| Appearance | Crystalline Flakes |
| Color | White |
| Merck | 14,7304 |
| BRN | 606907 |
| pKa | 10.01(at 25℃) |
| PH | 7 (0.1g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, halogens. |
| Sensitive | Hygroscopic |
| Explosive Limit | 1.4-9.5%(V) |
| Refractive Index | 1.6188 (estimate) |
| Physical and Chemical Properties | Melting Point: 57 °c Boiling Point: 282 ℃ density: 1.213 flash point: 123 ℃ water-soluble:<0.01g/100 mL at 20.5 C Appearance: bright purple crystals
|
| Use | It is used as a carrier, surfactant, antiseptic and dye intermediate for hydrophobic synthetic fibers such as chlorinated polyamide and polyester. In Japan, 2-hydroxybiphenyl and its sodium salt are used for the fungicide of citrus. In the wax mixed with 0.8% of the goods, the use of spray method in the citrus after harvest, can also be used with biphenyl, rot blue to a minimum. The range of fruits allowed to be used in the United Kingdom, the United States and Canada |
Hydroxybiphenyl - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R50 - Very Toxic to aquatic organisms R37/38/50 - R36 - Irritating to the eyes |
| Safety Description | S22 - Do not breathe dust. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | DV5775000 |
| TSCA | Yes |
| HS Code | 29071900 |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 2.48 g/kg (Hodge) |
Hydroxybiphenyl - Upstream Downstream Industry
| Raw Materials | Sodium carbonate Sodium hydroxide |
Hydroxybiphenyl - Nature
Open Data Verified Data
white, light yellow to light red powder, slightly phenolic. Flammable. Almost insoluble in water, soluble in methanol, acetone, benzene, xylene, trichloroethylene, dichlorobenzene and other organic solvents. In case of high heat, open flame or contact with oxidant, there is a risk of combustion. Toxic nitrogen oxide smoke is released by thermal decomposition.
Last Update：2024-01-02 23:10:35
Hydroxybiphenyl - Preparation Method
Open Data Verified Data
- using cyclohexanone route to prepare OPP, namely, using cyclohexanone as raw material, condensation dehydration under acid catalysis to obtain the dimerization Intermediate 2-(1-cyclohexenyl) cyclohexanone and 2-ring hexylene cyclohexanone, O-Phenylphenol was synthesized by dehydrogenation.
- a mixture of O-Phenylphenol and p-Phenylphenol is obtained from the by-product of phenol production by sulfonation method. The mixture is heated and dissolved in trichloroethylene, and the crystals of p-Phenylphenol are precipitated by cooling, and then centrifuged and filtered, the solid was dried to give P-Phenylphenol. The mother liquor was washed with sodium carbonate solution, neutralized with dilute sodium hydroxide and acidified to obtain O-Phenylphenol.
Last Update：2022-01-01 09:30:40
Hydroxybiphenyl - Use
Open Data Verified Data
has a strong bactericidal function, used as wood, leather, paper preservative and fruit and vegetable meat storage preservative. It is also used in the production of flame retardants, preservatives, dye carriers, surfactants, dye intermediates, cosmetics and for the production of advanced explosives.
Last Update：2022-01-01 09:30:40
Hydroxybiphenyl - Safety
Open Data Verified Data
rat oral LD50:2.48g/kg. It is irritating to the skin and eyes. Staff should be protected. Mixed loading and transportation with oxidant, alkali and edible chemicals are strictly prohibited. During transport should be protected against exposure to sunlight, rain, and high temperature.
Last Update：2022-01-01 09:30:41
Hydroxybiphenyl - Reference Information
| FEMA | 3959 | 2-PHENYLPHENOL |
| LogP | 3.18 at 22.5℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 73) 1999 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | O-Phenylphenol (OPP) is a very widely used organic chemical products, widely used in sterilization, printing and Dyeing auxiliaries and surfactants, synthetic new plastics, resin and polymer materials, stabilizers and flame retardants and other fields. OPP and its sodium salt has a broad spectrum of sterilization in addition to mildew, and low toxicity and tasteless, is a good preservative, can be used for fruit and vegetable mold preservation, especially for citrus mold, can also be used for the treatment of lemon, pineapple, pear, peach, tomato, cucumber, etc., can reduce the decay to a minimum. |
| Application | the use of O-Phenylphenol at high concentrations is suitable for inhibiting fungal growth (Fungistatic effect) or even for killing fungi (fungicidal effect). CN200580026288 discloses the use of O-Phenylphenol and/or its derivatives for inhibiting asexual propagation of fungi, and also relates to filter media, adhesives, building materials, building accessories, fabrics, fur, paper, leather or leather products, as well as detergents, detergents, rinses, hand washes, hand dishwashing agents, automatic dishwashing agents, and for finishing building materials, building accessories, fabrics, fur, paper, reagents for leather or leather products, etc. |
| identification test | take 1% sample of ethanol solution 1ml, add 0.2% borax solution 4m1 and a small amount of 2, small crystals of 6-dichlorobenzoquinone chlorimine, after shaking, the solution should appear blue to blue. Take 1% sample of ethanol solution lml, add formaldehyde sulfuric acid solution (TS-113) 1M1, the interface should be red. |
| content analysis | accurately weigh about 2g of powdered sample, add 25ml of sodium hydroxide solution (TS-224), if necessary, it can be dissolved by warming, and water is added to 500ml after cooling, which is used as a sample solution. Take 25ml of this sample solution into the iodine bottle, Add 30ml of 0.1mol/L potassium bromate solution accurately, add 5ml of potassium bromide solution (TS-181) and 50ml of methanol, and fully shake. Immediately add about 10ml of 1:1 dilute hydrochloric acid, plug it immediately, and shake it gently to react for 30s. 15ml of potassium iodide solution (TS-192) was taken and placed in the upper part of the iodine bottle. The stopper was released and allowed to flow into the bottle. Free iodine was titrated with 0.1mol/L sodium thiosulfate solution, and starch solution (TS-235) was used as indicator. Another blank test was carried out by the same method, and the content was obtained by the following formula. Content (%) = 4.255 ×(a-b)/sample volume (g)× 50 × 100% where a -- Volume of sodium thiosulfate consumed by blank, m1; B- volume of sodium thiosulfate consumed in the sample solution, ml. |
| toxicity | ADI 0~0.2mg/kg (0.2~1.0mg/kg under certain conditions; FAO/WHO,2001). LD50 2.7~3.0g/kg (rat, oral). Tokyo Tokyo Institute of Health found on experimental animals have obvious effect of bladder cancer. |
| usage limit | GB 2760-2001: Citrus Fresh-keeping 1.0g/kg, residue ≤ 12mg/kg. |
| Use | fungicide; Fruit and vegetable preservative. Mainly used for anti-mildew of citrus epidermis. In addition to citrus, European Economic Community countries and the United States are still used for cucumber, carrot, apple, melon, tomato, etc. Japan only for citrus, the maximum residue of 0.01g/kg(1990). The use of the following countries (allowed dosage, mg/kg) Canadian Cherry, 5; Citrus, cucumber, pepper, pineapple, tomato, 10; Sweet potato, 15; Carrot, peach, plum fruit, 20; Apple, pear, 25; Melon, 12. EC citrus, 12. Dutch citrus, 10. British citrus, 70; Apples, pears, pineapple, 10; Melon, 125. US (FDA,§ 180.129,2000) Cherry, 5; Citrus, cucumber, grape, grapefruit, kumquat, lemon, lime, orange, pepper, pineapple, tomato, sweet potato, 15; carrot, peach, Prunus, 20; Apple, pear, 25; Melon, 125 (edible part is less than or equal to 10). Usage: This product is mixed into the wax by about 0.8%, and treated by spraying or dipping, which can prevent the corruption caused by the white mould. This product has the best effect in combination with biphenyl. For moldy changes caused by Penicillium sp. On citrus, After 3~5 weeks, untreated about 60.5% moldy, and the goods after treatment only 3.4%. as antiseptic fungicide, China's provisions can be used for citrus preservation, the maximum use of 3.0g/kg, the residue is not more than 12mg/kg. as a preservative, China can also be used for citrus preservation, the maximum use of 3.0g/kg, the residue is not more than 12mg/kg. This product is used for strong sterilization function, used for wood, leather, paper preservation and fruit and vegetable meat storage preservation. 2-hydroxybiphenyls are used as carriers, surfactants, sterilization preservatives and dye intermediates for hydrophobic synthetic fibers such as chlorinated polyamide and polyester. In Japan, 2-hydroxybiphenyl and its sodium salt are used for the fungicide of citrus. In the wax mixed with 0.8% of the goods, the use of spray method in the citrus after harvest, can also be used with biphenyl, rot blue to a minimum. The United Kingdom, the United States and Canada allow the use of a larger range of fruits, including apples, pears, pineapple and so on. The product is also used in cosmetics as a preservative. The oral LD50 of 2-hydroxybiphenyl in rats is 2.7-3.0g/kg. It is used for preservation of fruits and vegetables detection of triose reagent by fluorescence. Dye Intermediates. used as a deoxyribonuclease (DNase) inhibitor; Used as a detection reagent for triose analysis |
| production method | can be recovered from the distillation residue of phenol produced by sulfonation. The distillation residue of phenol contains about 40% of phenyl phenol, and the other components are phenol, inorganic salts, water and the like. After vacuum distillation, the mixed phenyl phenol fraction section is separated, the vacuum degree is 53.3-66.7kPa, and the temperature is 65-75 °c, and the cut-off is above 100 °c, but not more than 1345 °c. The solubility of O-and p-hydroxybiphenyl in Trichloroethylene is different, and the two are separated into pure substances. The mixture (mainly 2-hydroxybiphenyl and 4-hydroxybiphenyl) was heated and dissolved in trichloroethylene. After cooling, 4-hydroxybiphenyl crystals were first precipitated, centrifuged and filtered, drying gave 4-hydroxybiphenyl. The mother liquor was washed with sodium carbonate solution, and diluted alkali solution was added to salt 2-hydroxybiphenyl. After being allowed to stand and layered, the sodium salt of 2-hydroxybiphenyl in the upper layer was dewatered under reduced pressure to obtain a finished sodium salt product. The sodium salt of 2-hydroxybiphenyl is a white to pale red powder. Very soluble in water, in 11.1g water soluble 122G, 2% of the aqueous solution pH 12.2. Also soluble in acetone, methanol, soluble in glycerol, but insoluble in oil. 2-hydroxybiphenyl sodium salt can be acidified to produce 2-hydroxybiphenyl, both of which are food additives. A mixture of O-Phenylphenol and p-Phenylphenol was obtained from the by-product of phenol production by sulfonation method. The mixture was heated and dissolved in trichloroethylene, and crystals of p-Phenylphenol were precipitated by cooling, and then centrifuged and filtered, the solid was dried to give P-Phenylphenol. The mother liquor was washed with sodium carbonate solution, neutralized with dilute sodium hydroxide and acidified to obtain O-Phenylphenol. The distillation residue of phenol production by sulfonation contains about 40% mixed sites (Para and ortho) phenyl phenol. Depending on their solubility in trichloroethylene, the distillation residue was fractionated under reduced pressure at a vacuum of 53.3-66.7KPa to collect a 65-100 ° C. Fraction, I .e., mixed Phenylphenol. The mixture was dissolved in trichloroethylene by heating, and after Cooling, p-Phenylphenol was freshly precipitated. After centrifugal filtration, the mother liquor was washed with sodium carbonate solution to make O-Phenylphenol a sodium salt. After standing, the upper sodium salt was taken out and acidified to obtain the product. The distillation residue from the sulfonation process to produce phenol contains about 40% of mixed-position (P-position and O-position) Phenylphenol, and the ortho-position product is isolated and recovered using the difference between fractional distillation and solubility in trichloroethylene. The distillation residue was subjected to fractional distillation under reduced pressure at a vacuum of 53.3 to 100 kPa, and a fraction at 65 to ° C. Was collected as mixed Phenylphenol. The mixture was dissolved in trichloroethylene by heating, and after Cooling, p-Phenylphenol was precipitated. After centrifugal filtration, the mother liquor was washed with sodium carbonate solution to make O-Phenylphenol a sodium salt. After standing, the upper sodium salt was taken out and acidified to obtain the product. The product obtained by heating dibenzofuran and metallic sodium to about 200 ° C. And decomposing with an acid. It is derived from the hydrolysis of 2-aminobiphenyl after diazotization. |
| category | pesticide |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 2000 mg/kg; Oral-mouse LD50: 1050 mg/kg |
| stimulation data | Skin-rabbits 20 mg/24 h moderate; eye-rabbit 0.05 mg/24 h severe |
| explosive hazard characteristics | explosive when mixed with air |
| flammability hazard characteristics | flammable; Combustion-induced irritating smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| extinguishing agent | dry powder, foam, sand |
| spontaneous combustion temperature | >520°C |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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Raw Materials for Hydroxybiphenyl