Molecular Formula | C6H6O |
Molar Mass | 94.11 |
Density | 1.071g/mLat 25°C(lit.) |
Melting Point | 40-42°C(lit.) |
Boling Point | 182°C(lit.) |
Flash Point | 175°F |
JECFA Number | 690 |
Water Solubility | 8 g/100 mL |
Solubility | H2O: 50mg/mL at20°C, clear, colorless |
Vapor Presure | 0.09 psi ( 55 °C) |
Vapor Density | 3.24 (vs air) |
Appearance | liquid |
Specific Gravity | 1.071 |
Color | faintly yellow |
Odor | Sweet, medicinal odor detectable at 0.06 ppm |
Exposure Limit | TLV-TWA skin 5 ppm (~19 mg/m3 )(ACGIH, MSHA, and OSHA); 10-hour TWA 5.2 ppm (~20 mg/m3 ) (NIOSH); ceiling60 mg (15 minutes) (NIOSH); IDLH 250ppm (NIOSH). |
Merck | 14,7241 |
BRN | 969616 |
pKa | 9.89(at 20℃) |
PH | 6.47(1 mM solution);5.99(10 mM solution);5.49(100 mM solution); |
Storage Condition | 2-8°C |
Sensitive | Air & Light Sensitive |
Explosive Limit | 1.3-9.5%(V) |
Refractive Index | n20/D 1.53 |
Physical and Chemical Properties | Characteristics of colorless needle-like crystals or white crystal frit. There is a special odor and burning taste, very dilute solution has a sweet taste. melting point 43 ℃ boiling point 181.7 ℃ freezing point 41 ℃ relative density 1.0576 refractive index 1.54178 flash point 79.5 ℃ easy solubility soluble in ethanol, ether, chloroform, glycerol, carbon disulfide, petrolatum, volatile oil, fixed oil, strong alkali aqueous solution. Almost insoluble in petroleum ether. |
Use | It is used as a raw material for the manufacture of resins, synthetic fibers and plastics, and also used in the production of medicines and pesticides. |
Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R34 - Causes burns R48/20/21/22 - R68 - Possible risk of irreversible effects R40 - Limited evidence of a carcinogenic effect R39/23/24/25 - R11 - Highly Flammable R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R24/25 - |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S28A - S28 - After contact with skin, wash immediately with plenty of soap-suds. S24/25 - Avoid contact with skin and eyes. S1/2 - Keep locked up and out of the reach of children. S36 - Wear suitable protective clothing. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. |
UN IDs | UN 2821 6.1/PG 2 |
WGK Germany | 2 |
RTECS | SJ3325000 |
FLUKA BRAND F CODES | 8-23 |
TSCA | Yes |
HS Code | 29071100 |
Hazard Class | 6.1 |
Packing Group | II |
Toxicity | LD50 orally in rats: 530 mg/kg (Deichmann, Witherup) |
colorless needle-like crystals or white crystals. There is a special odor, very dilute solution has a sweet taste. The impure product changes to light red or red under the action of light and air, and changes color faster in case of alkali. Rate 11 54178, flash point 79. 44 ℃ (closed Cup), 85 ℃ (Open Cup), spontaneous ignition point 715 ℃, combustion limit of 1_ 7%~ 8.6% of the mixture of steam and air. Flammable, strong corrosion. Toxic. 1g of phenol dissolved in about 15ml of water (0.67%,25 deg C after heating can be dissolved in any proportion), 12mL of benzene. Soluble in ethanol, ether, chloroform, glycerol, carbon disulfide, petrolatum, volatile oil, fixed oil, strong alkali aqueous solution. Almost insoluble in petroleum ether. The pH of the aqueous solution was about 6.0.
There are mainly sulfonation method and cumene method. The sulfonation method is based on benzene as raw material, sulfonated with sulfuric acid to generate benzene sulfonic acid, neutralized with sulfurous acid, and then alkali fusion with caustic soda, and prepared by sulfonation and vacuum distillation and other steps. Cumene method is propylene and benzene in aluminum chloride catalyst under the formation of cumene, cumene by oxidation of hydrogen peroxide cumene, and then sulfuric acid decomposition, phenol and acetone.
This product contains C6H6O not less than 99.0%.
The freezing point of this product (General rule 0613) is not less than 40°C.
used in oil field industry, is also an important organic chemical raw materials, it can be used to prepare phenolic resin, caprolactam, bisphenol A, salicylic acid, picric acid, pentachlorophenol, phenolphthalein, N-acetoethoxyaniline and other chemical products and intermediates in chemical raw materials, alkyl phenols, synthetic fibers, plastics, synthetic rubber, pharmaceuticals, pesticides, spices, dyes, coatings and oil refining and other industries have a wide range of applications.
take 0.lg of this product, add 10ml of water to dissolve, and test according to the following method.
Non-volatile matter 5.0g of this product is taken, after being distilled and dispersed in a water bath, it is dried at 105 ° C. To constant weight, and the remaining residue shall not exceed 2.5mg.
take about 0.15g of this product, accurately weigh it, put it in a 100ml measuring flask, add an appropriate amount of water to dissolve and dilute to the scale, shake well; Take 25ml of precision measurement, put it in an iodine bottle, add 30ml of bromine titration solution (0.05mol/L) and 5ml of acid, immediately plug, shake for 30 minutes, after standing for 15 minutes, pay attention to opening the stopper, and add 6ml of potassium iodide test solution, immediately plug, fully shake, add chloroform 1ml shake, with sodium thiosulfate titration solution (0.1 mol/L titration, to the near end point, add starch indicator solution, continue titration to blue disappeared, and the titration results are corrected by blank test. Each 1ml of bromine titration solution (0.05mol/L) corresponds to 1.569mg of C6H6O.
Disinfection antiseptic.
light shielding, sealed storage.
FEMA | 3223 | PHENOL |
olfactory threshold (Odor Threshold) | 0.0056ppm |
freezing point | 41 ℃ |
Henry's Law Constant | 1.09 at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997) |
LogP | 1.47 at 30℃ |
(IARC) carcinogen classification | 3 (Vol. 47, 71) 1999 |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
important organic chemical raw material | phenol is an important organic chemical raw material, mainly used in the manufacture of phenolic resin, bisphenol a, pesticide fungicide salicylic acid, herbicide 2,4-D, explosive picric acid, etc. In addition, this product is also a raw material for the manufacture of nylon, epoxy resin, paint, paint, perfume, synthetic detergent and plasticizer. Phenol is abbreviated as phenol, commonly known as carbolic acid. It is a weak acid and has acid properties. Phenol is extremely weak in acidity and carbonic acid is weak, which cannot fade the acid-base indicator. The molecule of phenol contains hydroxyl (OH), and the compounds that are directly connected to the benzene ring are called phenols. Common phenols include: o-cresol, m-cresol, p-cresol, m-diphenol, p-diphenol. The chemical properties of phenol are more active, and it gradually becomes reddish crystals in the air or in case of unclean substances. It has a special smell, is toxic, and is highly corrosive. In humid air, it can absorb the moisture in the air by itself and gradually liquefy. Slightly soluble in water, soluble in benzene and alkaline solution, soluble in ethanol, ether, chloroform, glycerin and other organic solvents. Phenol is weakly acidic, and it reacts with alkali to form a salt, which looks blue when it meets ferric chloride solution. Coal tar was once the main source of phenol and can be extracted from it with sodium hydroxide solution. With the development of industry, natural products have been in short supply. By the 2030s, the output of synthetic phenol has exceeded that of natural products. Industrial production was the first to use the sulfonation method, which eutectic sodium benzenesulfonate and sodium hydroxide to form a sodium salt of phenol, which was obtained by acid treatment. This method is troublesome to operate, but it does not require strict equipment and has a high yield. In recent years, chlorobenzene hydrolysis and cumene oxidation are mainly used in industry. The by-product acetone obtained by the latter is also an important industrial raw material, so this method has greater economic value, but it has stricter equipment and technology requirements. The following figure shows the technological process of preparing phenol by cumene method: |
synthesis and preparation method of phenol | phenol exists in coal tar, so coal tar is one of the industrial sources of phenol, but it is far from meeting the requirements. most phenol is obtained by synthesis. there are many methods for synthesis of phenol phenol, mainly cumene method. 1. Cumene method: This method is to generate propylene and benzene under the catalysis of aluminum trichloride to generate cumene, which is oxidized to generate cumene hydroperoxide, and then decomposed with cation exchange resin to obtain phenol and acetone. Every ton of phenol produced can produce 0.62 tons of acetone by-product. 2. Sulfonation method: benzene is used as raw material, sulfonated with sulfuric acid to generate benzenesulfonic acid, neutralized with sodium sulfite, and then dissolved with caustic soda. Phenol is obtained by acidification and decompression distillation. 3. Hydrobenzene hydrolysis method: Hydrobenzene is hydrolyzed with caustic soda under high temperature and high pressure to produce sodium phenol, and then neutralized to obtain phenol. major phenol manufacturers in China: Beijing Yanshan petrochemical company, Shanghai Gao Qiao chemical plant, Jinxi chemical plant, Jilin petrochemical plant, Taiyuan chemical plant, blue star Harbin petrochemical plant, Jiangxi Pingxiang chemical plant. At present, about half of the phenol is used to make phenolic resin, followed by bisphenol A. In the presence of sulfuric acid, acetone can be condensed to produce bisphenol A in a large and quantitative manner, which is used as a raw material for epoxy or polycarbonate resin. A part of phenol is used for the addition of long-chain olefins such as diisobutene or tripolypropylene and tetra-polypropylene to make isooctylphenol, isononylphenol or iso-dodecylphenol, which is used as a raw material for non-ionic surfactants. |
solubility | slightly soluble in water at room temperature, soluble in benzene and alkaline solution, soluble in ethanol, ether, chloroform, glycerol, glycerol, glacial acetic acid and other organic solvents, insoluble in petroleum ether. The solubility in water is: 4.832% at 11 ℃; 2.360% at 35 ℃; 7.330% at 58 ℃; 11.830% at 77 ℃; phenol and water can be miscible in any proportion at 84 ℃. |
solubility in water (g/100ml) | dissolution grams per 100ml of water at different temperatures (℃): 8.3g/20 ℃; Miscibility/40 ℃ |
disinfectant | phenol can denature proteins, so it has a bactericidal effect. it shows strong antibacterial activity against many microorganisms, such as gram-positive bacteria, gram-negative bacteria, mycobacteria and certain fungi and viruses, and has poor killing power against tuberculosis, spores and acid-resistant bacteria. Phenol has the strongest activity in acidic solution; increasing temperature can also improve its antibacterial activity; the presence of organic matter will make its activity disappear. Dilute solution phenol can be used as a disinfectant and has been used in surgery. In the 19th century, although the British doctor Lister had superb surgical techniques, he could not solve the problem of death due to infection after surgery, and the mortality rate was 5%. He managed to find drugs to kill the microorganisms that infected the wound. Once he discovered that a cleaner used carbolic acid to eliminate the odor of the gutter, which inspired him to use a dilute carbolic acid solution for surgical operations for the first time. The patients treated with such disinfection did not have any accidents such as infection. This incident caused a sensation all over the world. In 1876, he completed the disinfection paper. Only 10 years after its publication, the disinfection method was fully applied all over the world. phenol is mainly used as an antibacterial preservative in injection and topical preparation products. the effective concentration is 0.1% ~ 0.5%, which can inhibit the growth of common bacteria. bacteria can be killed at 1% concentration, but 3% concentration is required to kill staphylococcus and streptococcus, and more than 1.3% concentration is required to kill mold. Spores and viruses are very tolerant to this product, so they are generally ineffective. Commonly used 1% ~ 5% concentration for disinfection of houses, poultry (livestock) houses, sites and other environments, 3% ~ 5% concentration for disinfection of utensils and instruments. The application method is spraying or soaking, and the soaking and disinfection of utensils and instruments should be more than 30~40 minutes, but the food trough and drinking device can only be used after soaking and disinfection with normal water before washing. phenol is highly corrosive and toxic, mainly acting on the central nervous system, and the oral lethal dose for adults is about 1g. It has irritation, anesthesia and necrosis effects on the skin and mucous membranes. It is toxic to skin contact, swallowing or inhaling phenol; taking a small amount of phenol by mistake can cause nausea, vomiting, shock, coma, and even death due to respiratory failure. When phenol is used as a preservative, the dosage is small, so there are fewer adverse reactions. Because phenol is corrosive and irritating to tissues, it has been replaced by more effective and low-toxicity phenolic derivatives, but the carbolic acid coefficient can still be used to express the bactericidal strength. If the carbolic acid coefficient of phenol is 1, when the carbolic acid coefficient of cresol to typhoid bacillus is 2, it means that the bactericidal ability of cresol is 2 times that of phenol. Reference materials: Hu Gongzheng, Li Honor, Editor-in-Chief Xu Lanju. New Handbook of Practical Veterinary Drugs. Zhengzhou: Henan Science and Technology Press. |
Reaction with concentrated bromine water | Substitution reaction of phenol and bromine water, because phenol can dissolve tribromophenol that is hardly soluble in water, in order to prevent the dissolution of tribromophenol by phenol that has not been reacted, concentrated bromine water should be used in the experiment, preferably saturated bromine water. At the same time, the phenol aqueous solution should be as dilute as possible. In the experiment, attention should also be paid to controlling the amount of bromine water, because excessive concentrated bromine water will react with tribromophenol to generate yellow precipitate, therefore, the amount of bromine water should not be too much. When white precipitate appears, immediately stop adding bromine water. If phenol is added dropwise to bromine water, the generated precipitate will not dissolve. |
toxicity | contact of skin with phenol aqueous solution produces local anesthesia and ulcer. Can cause acute poisoning. LD50530mg/kg (rat, oral). |
usage limit | FEMA(mg/kg): soft drinks, cold drinks, candy, baked goods, gelatin sweets and pudding, all 0.5 |
hazard | this product is in danger of combustion when exposed to open flame, high temperature and strong oxidant. when heated, it will release flammable steam, which can form explosive mixture with air. Phenol contact with the human body can cause severe tissue burns. The lethal dose can be reached by skin absorption or inhalation. The maximum allowable concentration in air is 5mg/m3. The corrosive properties of its aqueous solution destroy cells. It should be stored in a cool, ventilated, and high-dryness place, away from fire and heat sources, isolated from oxidants, and the packaging should be sealed to prevent moisture absorption and deterioration. Contact with the skin will turn white or red, first wash with water, then apply ointment. Reduce irritation and pain. Wear gas masks and gloves when handling spills. Fire fighting can use water, sand, foam and carbon dioxide. Contaminated areas are washed with soapy water. UN No.: 1671/6225/6.1-04/710, domestic name number: 61067. |
use | is an important organic synthetic raw material, used to make phenolic resin, bisphenol A, phenolphthalein, picric acid, salicylic acid, alkyl phenol and other chemicals, and can also be used as a solvent used as a raw material for making resins, synthetic fibers, plastics, also used in the production of medicines, pesticides, etc. It is a raw material for the production of phenolic resins, paints, and medicines Used as analytical reagents GB 2760-1996 regulations are temporarily allowed to use edible spices. Phenol is an important organic chemical raw material. It can be used to produce phenolic resin, caprolactam, bisphenol A, salicylic acid, picric acid, pentachlorophenol, 2,4-D, adipic acid, phenolphthalein N-Acetylethoxyaniline and other chemical products and intermediates have important uses in chemical raw materials, alkylphenols, synthetic fibers, plastics, synthetic rubber, medicine, pesticides, fragrances, dyes, coatings and oil refining industries. In addition, phenol can also be used as a solvent, experimental reagent and disinfectant. In 1997-2002, the demand for phenol in major regions such as the United States, Western Europe and Japan maintained an average annual growth rate of 4.2%. Phenol is an important raw material for pesticide production. It can produce insecticides carbofuran, fenothion, fruit and vegetable phosphorus, fungicides prochloraz, triadimefon, difenoconazole, herbicides 2,4-drop, 2,4-drop butyl ester and rodenticide rodenticide rodent phosphorus, brominated rodent phosphorus. In addition, phenol alkylation produces alkylphenols, such as nonylphenol, dinonylphenol, secondary octylphenol, and polyarylphenols, such as 2-methylbenzylphenol, 2-dimethylbenzylphenol, etc., are important intermediates of surfactants. Colorimetric determination of nitrate and nitrite in sulfuric acid solution. Indirect determination of potassium. Used to bind excess free halogen. Determination of oxides of alkaline earth metals. Verification of ammonia, hypochlorite, 1 hydroxy acid. As a solvent for determining the molecular weight of refractory compounds. Microscopic staining, etc. |
production method | the preparation method is as follows. Sulfonation alkali fusion method The old industrial production method of phenol is sulfonation alkali fusion method, which uses concentrated sulfuric acid or sulfur trioxide as a sulfonating agent to sulfonate benzene in the gas phase and convert it into benzenesulfonic acid, and then neutralize it with sodium sulfite, and then make sodium benzenesulfonate react with the caustic soda in the molten state to generate sodium phenol and Na2SO3 dissolved in water, crystallize to separate it, and the sodium phenol solution after dipping and separation is acidified with sulfur dioxide or dilute sulfuric acid to produce crude, the finished product is distilled under reduced pressure. Propylene separated from cracked gas by the cumene method is in the presence of aluminum trichloride catalyst, and benzene undergoes alkylation reaction at 80~90 ℃ atmospheric pressure, and is separated by distillation to obtain cumene. cumene is directly oxidized to cumene hydroperoxide with air at 100~120 ℃ and 300~400 kPa pressure, the oxidation solution is concentrated to about 80%, cumene hydroperoxide is cracked into phenol and acetone with sulfuric acid at 60 ℃ atmospheric pressure, finally, acetone and phenol were refined respectively. The method has low cost and less three wastes. The raw materials come from propylene and petroleum benzene in petroleum gas, and phenol and acetone can be obtained at the same time. These two products are chemical raw materials with a wide range of uses. The intermediate product cumene hydroperoxide can be separated as an initiator for the rubber industry, and the intermediate cumene can be used as a raw material for the production of the intermediate p-isopropylaniline for the herbicide isopropylon. This method is suitable for large-scale continuous production. At present, most phenol production in the world uses this method. Phenol was first recovered from coal tar, and most of it is currently synthesized. By the mid-2060s, the technical route of producing phenol and acetone by the cumene method has been developed to account for half of the world's phenol production. At present, the phenol produced by this process has accounted for more than 90% of the world's phenol production. Other production processes include toluene chlorination, chlorobenzene and sulfonation. There are two production methods in China: cumene method and sulfonation method. As the sulfonation method consumes a large amount of sulfuric acid and caustic soda, China will also retain only a few sulfonation devices, and gradually produce mainly by the cumene method. 1. Sulfonation method uses benzene as raw material, sulfonates with sulfuric acid to generate benzene sulfonic acid, neutralizes with sulfurous acid, and then uses caustic soda for alkali melting, and is prepared by sulfonation and decompression distillation. Raw material consumption quota: pure benzene 1004 kg/t, sulfuric acid (98%)1284 kg/t, sodium sulfite 1622 kg/t, caustic soda (100%)1200 kg/t. 2. Propylene and benzene by the cumene method generate cumene under the action of aluminum trichloride catalyst. cumene is oxidized to generate cumene hydroperoxide, and then decomposed by sulfuric acid or resin. Phenol and acetone were obtained at the same time. About 0.6t of acetone per ton of phenol. Raw material consumption quota: benzene 1150kg/t, propylene 600kg/t. 3. Chlorobenzene hydrolysis method Chlorobenzene is catalytically hydrolyzed with caustic soda aqueous solution under high temperature and high pressure to generate sodium benzene, and then neutralized with acid to obtain phenol. 4. Crude phenol refining method is obtained from coal tar crude phenol refining. 5. In the presence of a solid molybdenum catalyst, Rasciphene underlies a chlorine oxidation reaction at high temperature to generate chlorobenzene and water. Chlorobenzene underlies catalytic hydrolysis to obtain phenol and hydrogen chloride, which is recycled. Cumene is formed from benzene and propylene in the presence of aluminum trichloride, cumene hydroperoxide is formed by oxidation, and then phenol and acetone are decomposed by dilute sulfuric acid. After separation, an appropriate amount of zinc powder is added to decolorise, and then steamed. |
category | toxic substances |
toxicity classification | highly toxic |
acute toxicity | oral-rat LD50: 317 mg/kg; Oral-mouse LD50: 270 mg/kg |
stimulation data | skin-rabbit 500 mg/24 hours severe; Eyes-rabbit 5 mg/30 seconds mild |
explosive hazard characteristics | corrosive to skin and cornea |
flammability hazard characteristics | combustible in case of open flame, high temperature and strong oxidant; Stimulating smoke produced by combustion |
storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidant. |
fire extinguishing agent | sand, foam, water |
occupational standard | TLV-TWA 5 PPM (19 mg/m3); STEL 10 PPM (38 mg/m3) |
spontaneous combustion temperature | 715°C |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
immediate life-threatening and health concentration | 250 ppm |