Phenol[2], commonly known as carbonic acid), definition: molecular formula CsixHsixO，It is mainly made from cumene through oxidation and decomposition, which is importantOrganic chemical industryRaw materials, which can be used to produce phenolic resin, bisphenol A and other chemical products and intermediates, as well as solvents and disinfectants[2]。
Phenol is a kind ofOrganic compound, chemical formula is CsixHfiveOH，It is a colorless needle shaped crystal with special smell and is toxic. It is used to produce some resins, fungicides, preservatives and drugs (such asaspirin）Important raw materials.It can also be used to disinfect surgical instruments and excreta, sterilize skin, relieve itching and otitis media.Melting point 43 ℃, slightly soluble in water at room temperature, easily soluble in organic solvents;When the temperature is higher than 65 ℃, it can be mutually soluble with water in any proportion.Phenol Yescorrosive, contact will cause localProtein denaturationThe solution can be washed with alcohol if it touches the skin.A small part of phenol is oxidized toQuinoneIt is pink.It turns purple in case of ferric ion, and this method is usually used to test phenol.
twoOn October 27, 2017, the list of carcinogens published by the International Agency for Research on Cancer of the World Health Organization was preliminarily sorted out and referred to. Phenol was included in the list of Category 3 carcinogens.[3]
Chinese name
phenol
Foreign name
Phenol，phenyl hydroxide
Alias
Carbolic acid、phenol、Hydroxybenzene
chemical formula
CsixHfiveOH
molecular weight
ninety-four point one one one
CAS login number
108-95-2
EINECS login number
203-632-7
Melting point
43 ℃
Boiling point
181.9 ℃
Density
1.071 g/cm³
Appearance
Colorless or white crystalline powder
Flash point
72.5 ℃
Application
Chemical synthesis, oilfield industry, electroplating, solvent, medicine
Security description
S24/25；S26；S28；S36/37/39；S45
Hazard symbol
F (flammable), T (toxic), C (corrosive)
Hazard description
R23/24/25；R34；R48/20/21/22；R68
UN dangerous goods number
two thousand eight hundred and twenty-one
Solubility
Slightly soluble in cold water, miscible in ethanol, ether, chloroform, glycerin
chemical property
Weak acid, highly toxic, mutagen, reducing
stability
stable
Contraband
Strong oxidant, strong acid, strong base
Storage method
Cool and ventilated, low temperature and dark, pay attention to leakage
PSA
twenty point two three zero zero zero
LogP
one point three nine two two zero
Refractive index
one point five four two five
Customs code
two billion nine hundred and seven million one hundred and eleven thousand
In 1834, the German chemist Runge Fcoal tarIt is also called carbonic acid.It is the famous British doctor Liszt who made phenol famous for the first time.Lister found that most of the patients died of wound suppuration and infection after surgery.Occasionally, dilute phenol solution was used to spray surgical instruments and doctors' hands. As a result, the infection of patients was significantly reduced.This discovery makes phenol a powerful surgical disinfectant.Liszt is also known as the "father of surgical disinfection".[4]Laurent first made crystalline phenol in 1841[7]。
molecular structure
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Phenol molecule is composed of a hydroxyl group directly connected to the benzene ring.Due to the stability of the benzene ring, such a structure can hardly be transformed into a keto structure.
Figure 1
The resonance structure of phenol is shown in the figure.The oxygen atom of phenol hydroxyl group is determined by using sptwoHybridization, providing a pair of lone electrons to form with six carbon atoms of benzene ringOff field key。Large π bondEnhancedEnolThe polarity of the O-H bond is strengthened by the acidity of the hydroxyl group and the electron pushing effect of the hydroxyl group. Therefore, the hydrogen of the hydroxyl group in phenol can be ionized out.
Molecular structure data
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Molar refractive index: 28.13
Molar volume (cmthree/mol）：87.8
Isotonic specific volume (90.2K): 222.2
Surface tension (dyne/cm): 40.9
Polarization (10-24cmthree）：11.15[1]
physical property
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Molecular formula: CsixHfiveOH
Density: 1.071g/cmthree
Melting point: 43 ℃
Boiling point: 182 ℃
Flash point: 72.5 ℃
Refractive index: 1.553
Viscosity: 11.04 (mPa · s, 20 º C)[6]
Saturated vapor pressure: 0.13kPa (40.1 ℃)
Critical temperature: 419.2 ℃
Critical pressure: 6.13MPa
Ignition temperature: 715 ℃
Upper explosive limit（V/V）：8.5%
Lower explosive limit（V/V）：1.3%
Solubility: slightly soluble in cold water, miscible in ethanol, ether, chloroform, glycerin[1]
CAS No.: 108-95-2
EINECS No. 203-632-7
Soluble in water, miscible with ethanol, ether, acetic acid, chloroform, acetone, benzene and carbon disulfide.
It forms an azeotropic mixture with water. At this time, the content of this product is 9.2%, and the azeotropic point is 99.6 ℃.
Phenol is a kind of edible spice temporarily allowed to be used according to the provisions of GB2760-1996.
chemical property
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Acid-base reaction
The hydrogen of hydroxyl is easy to dissociate into hydrogen ions, so it is acidic and reacts with sodium hydroxide to produce sodium phenolate: PhOH+NaOH → PhONa+HtwoO
Phenol Ka=1.28 × 10-10The acidity is between the two levels of ionization of carbonic acid, so phenol cannot be mixed with NaHCOthreeIsoweak base reaction:
PhOˉ+COtwo+HtwoO→PhOH+HCOthreeˉ
This reaction phenomenon: white turbidity appears in the solution after carbon dioxide is introduced.
Cause: phenol precipitates due to low solubility.
Chromogenic reaction
Phenol turns purple when it meets ferric chloride solution, because phenol ion and Fe form a colored complex.
6PhOH+FeClthree→Hthree[Fe(OPh)six](Purple)+3HCl
Substitution reaction
The reactions on the aromatic ring of phenol are mainly electrophilic substitution reactions, such as halogenation, nitration, sulfonation, alkylation, acylation, carboxylation and coupling reaction with diazonium salt.This is due to the electron donating effect of hydroxyl group, which increases the electron cloud density of benzene ring.
It should be noted that the electrophilic substitution of phenol always occurs in the ortho and para positions of hydroxyl groups.This is the commonness of electron donating groups such as hydroxyl group.The hydrogen atom on the substituted phenolic hydroxyl group can be replaced by the carbon containing group to form ether or ester.
Redox
Phenol is easily oxidized to form benzoquinone (pink), and further oxidized to form brown polymer:
Phenol oxidation reaction
The oxidation products of phenol are generallyP-benzoquinone。This reaction can also use BrtwoAs oxidant.
It can be reduced to benzene by interaction with metal zinc;Under the action of nickel catalyst, hydrogenation can be reduced to cyclohexanol.
condensation reaction
Phenol and formaldehyde are condensed under the catalysis of acid or base to form phenolic resin.
Calculate chemical data
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Reference value for drainage parameter calculation (XlogP): None
Number of hydrogen bond donors: 1
Number of hydrogen bond receptors: 1
Number of rotatable chemical bonds: 0
Number of tautomers: 2
Topological molecular polar surface area: 20.2
Number of heavy atoms: 7
Surface charge: 0
Complexity: 46.1
Number of isotope atoms: 0
Determine the number of atomic structure centers: 0
Number of uncertain atomic structure centers: 0
Determine the number of chemical bond structure centers: 0
Number of uncertain chemical bond structure centers: 0
Number of covalent bond units: 1[1]
toxicology data
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Phenol is highly toxic. It is highly corrosive to the skin and mucous membrane, and can be absorbed by the skin and mucous membrane to cause poisoning. It starts to appear irritation, local anesthesia, and then becomes ulcer.Low concentration can denature protein and high concentration can precipitate protein, so it will directly damage various cells.In addition, phenol can cause kidney damage after separation in vivo, which may lead to secondary death.When phenol is taken by mistake, it strongly stimulates the stomach, causing severe abdominal pain.The tissue in contact with it is obviously corroded.When inhaling phenol vapor for a long time, you may suffer from phenol collapse, and feel headache, cough, fatigue, weakness, loss of appetite at the beginning. Later, you may suffer from continuous cough, skin itching, pressure in the kidney area, heaviness in the chest, severe insomnia, pale skin, proteinuria, and finally death due to chronic nephritis.The lethal dose of phenol taken by people is about 2~15g, and pure phenol is more toxic.TJ 36-79 stipulates that the maximum allowable concentration in workshop air is 5mg/mthree。[6]
acute toxicity
LDfifty: 317mg/kg (rat by mouth);270mg/kg (mouse by mouth);669mg/kg (rat percutaneous);630mg/kg (rabbit percutaneous)
LCfifty：316mg/mthree(Inhalation of rats, 4h)
thrill
Rabbit percutaneous: 500mg (24h), severe irritation.
Rabbit eye: 1mg, severe irritation.
Subacute and chronic toxicity
Animals inhale phenol vapor for a long time (115.2~230.2mg/mg/mthree）It can cause dyspnea, lung damage, weight loss and paralysis.
Mutagenicity
DNA inhibition: human Hela cells 1mmol/L.
Sister chromatid exchange: human lymphocytes 5 μ mol/L.
Teratogenicity
Female mice were exposed to 2800 mg/kg orally 6~15 days after pregnancy, which caused craniofacial (including nose and tongue) malformations, and 4g/kg caused musculoskeletal system development malformations.
other
The lowest oral toxic dose (TDLo) of rats: 1200mg/kg (6-15d pregnancy), causing embryotoxicity.[1]
Skin contact: immediately take off the contaminated clothes, wipe with glycerin, polyethylene glycol or polyethylene glycol and alcohol mixture (7:3), and then thoroughly clean with water.Or flush with plenty of flowing water for at least 15 minutes.Get medical attention.
Eye contact: immediately lift the eyelid, and thoroughly flush it with a large amount of flowing water or physiological saline for at least 15 minutes.Get medical attention.
Inhalation: quickly leave the site to a place with fresh air.Keep the respiratory tract unobstructed.If breathing is difficult, give oxygen.If breathing stops, perform artificial respiration immediately.Get medical attention.
Ingestion: drink 15~30mL vegetable oil immediately.Emetic.Get medical attention.
Fire fighting measures
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Hazard characteristics: flammable in case of open fire and high heat.
Isolate the leakage contaminated area and restrict access.Cut off the ignition source.It is recommended that emergency personnel wear dust masks (full face masks) and gas suits.
Small amount of leakage: cover with dry lime and soda ash.
Large amount of leakage: collect and recycle or transport to waste disposal site for disposal.
Handling storage
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Precautions for operation: closed operation, providing sufficient local ventilation.Isolate as much as possible.Operators must be specially trained and strictly abide by the operating procedures.It is recommended that operators wear self-priming filter type dust masks, chemical safety goggles, gas permeable gas suits, and chemical gloves.Keep away from kindling and heat sources, and smoking is strictly prohibited in the workplace.Use explosion-proof ventilation systems and equipment.Avoid dust generation.Avoid contact with oxidants, acids and alkalis.Load and unload gently during transportation to prevent damage to packaging and containers.Fire fighting equipment and leakage emergency treatment equipment of corresponding types and quantities shall be provided.Empty containers may leave harmful substances.
Precautions for storage: store in a cool and ventilated warehouse.Keep away from kindling and heat sources.Avoid light.The storage temperature shall not exceed 30 ℃, and the relative humidity shall not exceed 70%.Packing and sealing.It shall be stored separately from oxidants, acids, alkalis and edible chemicals, and mixed storage is strictly prohibited.Equip with corresponding types and quantities of fire-fighting equipment.The storage area shall be equipped with appropriate materials to contain leakage.The "five pairs" management system for extremely toxic substances shall be strictly implemented.
Determination of acidity of phenol
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Experimental operation
1. Take 2mL of phenol solution in the test tube, drop litmus reagent, and observe the phenomenon.
2. Take a small amount of phenol solid in three test tubes respectively, and add 2-3mL sodium hydroxide solution, 2-3mL sodium carbonate solution, 2-3mL sodium bicarbonate solution, fully shake, observe and compare the phenomenon (pay attention to whether there are bubbles in the test tube with salt solution)
3. Take 2mL of sodium hydroxide solution in the test tube, add 2-3 drops of phenolphthalein test solution, then add a small amount of phenol solid, and observe the color change.
Experimental phenomenon
Phenol does not redden litmus.
Phenol solid is easily soluble in sodium hydroxide solution and sodium carbonate solution, without bubbles;It is insoluble in sodium bicarbonate solution.
Phenol gradually lightens the red solution (sodium hydroxide solution with phenolphthalein test solution).
empirical conclusion
Phenol has weak acidity, which is between carbonic acid and bicarbonate ion.The acidity of phenol is too weak to make litmus reagent red.(The color change range of litmus test solution is: pH 5-8.)
Add sodium hydroxide solution drop by drop into the phenol solution just prepared while shaking until it is just clear. The product isSodium phenolate。Then continue to inject carbon dioxide gas, and the solution becomes turbid (carbon dioxide and water generate carbonic acid, and carbonic acid reacts with sodium phenolate to generate phenol and sodium bicarbonate).
In conclusion, according to the principle of strong acid making weak acid, acidity: HtwoCOthree＞ NaHCOthree。It is also known that the acidity of carbonic acid is stronger than that of phenol.
preparation
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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 through synthesis. There are many methods for the synthesis of phenol, mainly using cumene method.
Cumene process
In this method, propylene and benzene are catalyzed by aluminum trichloride to form cumene, which is oxidized to cumene hydroperoxide, and then decomposed by cation exchange resin to obtain phenol and acetone.Each ton of phenol produced can produce 0.62 tons of acetone.
Sulfonation method
Benzene sulfonic acid is generated from benzene by sulfonation with sulfuric acid, neutralized with sodium sulfite, dissolved with caustic soda, and phenol is obtained through acidification and vacuum distillation.
Hydrobenzene hydrolysis
Hydrobenzene is hydrolyzed with caustic soda under high temperature and pressure to produce sodium phenolate, which is neutralized to obtain phenol.
Major phenol manufacturers in China: Beijing Yanshan Petrochemical Company, Shanghai Gaoqiao General Chemical Plant, Jinxi Chemical Plant, Jilin Petrochemical, Taiyuan Chemical Plant, Bluestar Harbin Petrochemical Plant, Jiangxi Pingxiang Chemical Plant.[7]
application area
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It is widely used in the manufacture of phenolic resin, epoxy resin, nylon fiber, plasticizer, developer, preservative, insecticide, bactericide, dye, medicine, spice and explosives.
1. Instrument disinfection and excreta treatment 1%~5% aqueous solution.
2. Skin sterilization and antipruritic: apply 2% ointment to the affected part.
3. Ear drops of 1%~2% phenol glycerin were used for otitis media, three times a day.
Preparation and specification
Phenol ointment: 2%.
Phenol glycerin: ① 1%; ②2%。
Medication instructions
This product has strong tissue penetration and can only be used on small areas of skin.High concentration of external application can cause tissue damage, even necrosis.The aqueous solution is used on the body surface, and the concentration should not exceed 2%. After external use, no package is added.
Adverse reactions
This product is corrosive and irritant to tissues.It was reported that in places with poor ventilation, the cradle and mattress were disinfected and cleaned with phenol, which caused newbornshyperbilirubinemia, proved fatal to infants.
Contraindication
It is forbidden for children with diaper dermatitis and infants under 6 months old.Avoid applying to damaged skin and wounds.
Pharmacopoeia information
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source
This product contains CsixHsixO shall not be less than 99.0%.
character
This product is colorless to reddish acicular crystal or crystalline block, with special odor and moisture absorption. The aqueous solution shows weak acid reaction, and its color gradually darkens when exposed to light or in the air.
This product is easily soluble in ethanol, chloroform, ether, glycerin, fatty oil or volatile oil, soluble in water, slightly soluble in liquid paraffin.
Freezing point
The freezing point of the product (general rule 0613) is not lower than 40 ℃.
identify
Take 0.1g of this product, add 10mL of water to dissolve it, and then test it according to the following method.
1. Take 5mL of solution, add 1 drop of ferric chloride test solution, and it will turn blue and purple.
2. Take 5mL of solution, add bromine test solution, and a white precipitate will be generated immediately, but when the bromine test solution is excessive, a lasting precipitate will be generated.
3. The infrared absorption spectrum of this product should be consistent with the control spectrum (spectrum set 240 figure).
inspect
Nonvolatile matter
Take 5.0g of this product, evaporate and evaporate it in a water bath, dry it at 105 ° C to constant weight, and the residual residue shall not exceed 2.5mg.
Assay
Take about 0.15g of this product, precisely weigh it, put it into a 100mL measuring bottle, add appropriate amount of water to dissolve it and dilute it to the scale, shake it up, precisely measure 25mL, put it into a sulfonic bottle, precisely add 30mL of bromine titrant (0.05mol/L), then add 5mL of hydrochloric acid, immediately seal it, shake it for 30 minutes, after standing for 15 minutes, pay attention to slightly open the bottle plug, add 6mL of potassium iodide test solution, immediately seal it, after fully shaking, add 1mL of chloroform,Shake well, and titrate with sodium thiosulfate titrant (0.1mol/L). When the end point is near, add starch indicator solution, continue titrating until the blue color disappears, and correct the titration result with blank test.Every 1mL bromine titrant (0.05mol/L) is equivalent to 1.569mg CsixHsixO。
category
Disinfection and antiseptic.
Storage
Shading, sealed storage.[5]
security information
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Safety terminology
S24/25：Avoid contact with skin and eyes.
Avoid skin and eye contact.
S26：In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
After eye contact, immediately flush with plenty of water and seek medical advice.
S28：After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer).
After skin contact, immediately use a large amount of(designated by the manufacturer).
S36/37/39：Wear suitable protective clothing, gloves and eye/face protection.
Wear appropriate protective clothing, gloves and eye/face protection.
S45：In case of accident or if you feel unwell, seek medical advice immediately (show the lable where possible).
In case of an accident or feeling unwell, seek medical advice immediately (show the label if possible).
Risk terminology
R23/24/25：Toxic by inhalation, in contact with skin and if swallowed.
Toxic by inhalation, in contact with skin, and if swallowed.
R34：Causes burns.
Causes burns.
R48/20/21/22：Harmful : danger of serious damage to health by prolonged exposure through inh.,in contact with skin and if swallowed.
Harmful: danger of serious damage to health through long-term exposure through inhalation, skin and ingestion.
