Polarity of p-phenylenediamine and aniline

organic compound

China? |? This entry is reviewed by the writing and application project of "Popular Science China".

Review expert? Hu

P-phenylenediamine, also known as Ursi D, is an organic compound with the chemical formula of C6H8N2. It is one of the simplest aromatic diamines and a widely used intermediate. It can be used to prepare azo dyes and polymers, and to produce fur dyes, rubber antioxidants and photo developers. In addition, p-phenylenediamine is also a common sensitive reagent for the detection of iron and copper.

On October 27th, 2065438+071KLOC-0, the list of carcinogens published by the International Agency for Research on Cancer of the World Health Organization was preliminarily sorted out for reference, and p-phenylenediamine was in the list of three carcinogens. [2]

Chinese name

Ursol

Foreign name

ursol

Another name

Ursolic acid d, 1, 4- phenylenediamine, 1, 4- diaminobenzene.

chemical formula

C6H8N2

molecular weight

108. 14

Basic information, physical and chemical properties, molecular structure data, chemical calculation data, toxicology data, ecological data, application of first aid measures, protective measures, packaging, storage and transportation safety information.

Basic information

Chemical formula: C6H8N2

Molecular weight: 108. 14

Si Nuo. : 160-50-3

EINECSno。 : 203-404-7

physicochemical property

physical features

Density: 1. 15g/cm3

Melting point: 139℃

Boiling point: 267℃

Flash point: 135.9

Logarithmic coordinate: -0.68

Refractive index: 1.6 1

Critical pressure: 5.18mpa

Upper explosion limit (V/V): 9.8%

Lower explosion limit (V/V): 1.3%

Appearance: white to lavender solid

Solubility: slightly soluble in water, soluble in ethanol, ether, benzene, chloroform and acetone [1]

chemical property

1, flammability

2, weak alkalinity: because there are amino groups, there is weak alkalinity.

3. Reducibility: amino groups are reducible and easily oxidized by strong oxidants.

4. Substitution reaction: The influence of the amino group on the benzene ring enhances the activity of the ortho-para hydrogen of the amino group on the benzene ring, making it easy to be substituted.

5. Addition reaction: The benzene ring can undergo addition reaction.

Molecular structure data

Molar refractive index: 34.72

Molar volume (cc/mol): 93.9

Isotonic specific volume (90.2 k): 258.9

Surface tension (dyne/cm): 57.5

Polarity (10-24cm3): 13.76.

Computational chemical data

Reference value of hydrophobic parameter calculation (XlogP): None.

Number of hydrogen bond donors: 2

Number of hydrogen bond acceptors: 2

Number of rotatable chemical bonds: 0

Number of tautomers: 0

Polar surface area of topological molecules: 52

Number of heavy atoms: 8

Surface charge: 0

Complexity: 54.9

Atomic number of isotope: 0

Determine the number of atomic solid centers: 0

The number of uncertain atomic solid centers: 0

Determine the number of solid centers of chemical bonds: 0

The number of uncertain chemical bond solid centers: 0

* * * Number of valence bond units: 1[ 1]

Toxicological data

1, acute toxicity: LD 50: 80 mg/kg (taken orally by rats).

2, irritation: human skin: 250mg(24h), mild irritation.

3. Mutation

Microbial mutagenicity: Salmonella typhimurium 2μmol/ dish.

DNA inhibition: 200 mg/kg in mice.

Cytogenetic analysis: hamster ovary1.5 mg/L.

Sex chromosome deletion and non-segregation: Drosophila took orally 15500μmol/L(3d).

4, carcinogenicity

Review of IARC carcinogenicity: G3, the evidence of carcinogenicity to humans and animals is insufficient.

Ecological data

1, ecotoxicity

LD50: 5.74 mg/L (48 hours) (goldfish)

50% effective concentration: 74 mg/L (60 hours) (Tetrahymena pyriformis); 37 mg/L (30 minutes) (luminescent bacteria, micro-toxicity test).

2, biodegradability

Aerobic biodegradation: 168~672h

Anaerobic biodegradation: 672 ~ 2688 hours

3. Nonbiodegradable

Maximum absorption value of photolysis: 308nm.

Half-life of photooxidation in water: 30 ~1740 h.

Half-life of photooxidation in air: 0.28 ~ 2.8 hours.

App application

Synthetic dyes and pigments

P-phenylenediamine is an intermediate of azo disperse dyes, acid dyes, direct dyes and sulfide dyes. Add 3% hydrogen peroxide to turn black, and add 5% ferric chloride to turn brown. It has a strong affinity for keratin in hair, and its oxidation process is the fixation process of color when dyeing hair. It is not only the most effective component in hair dye, but also the most potentially harmful substance to human health.

synthetic resin

Aramid 14 14, which is condensed from p-phenylenediamine and terephthalic acid, is a kind of synthetic fiber with excellent properties and wide applications.

The reaction of p-phenylenediamine with maleic rosin monochloride can produce polyamide-imide resin with good performance, which can be used for film forming or wire drawing. It is a kind of resin with great practical value.

Kevlar is a polymer obtained by polycondensation of p-phenylenediamine and terephthaloyl chloride, which belongs to high temperature resistant polymer liquid crystal resin and is now used as a composite material for supersonic aircraft.

P-phenylenediamine can react with phosgene to produce its diisocyanate (PPDI), and then polyurethane with high crystallinity can be prepared. The product has excellent high temperature performance and can be used as thermoplastic and castable elastomer.

P-phenylenediamine reacts with aromatic dicarboxylic acid to produce aromatic polyamide, which can then be made into fiber fabric. They can be used as reinforcing materials for tires and V-belts, as reinforcing plastics, sports equipment, brake linings and other products requiring high strength and high modulus.

Rubber antioxidant

P-phenylenediamine and antioxidants synthesized from p-phenylenediamine have good effects, and there are many varieties at home and abroad. Mainly used as antioxidant for natural rubber and diene synthetic rubber.

P-phenylenediamine can be directly used to prevent the aging of raw rubber. One example is the combination of p-phenylenediamine and organic acid cobalt salt used in raw rubber, which is used to produce steel wire tires, and overcomes the aging problem caused by adding drilling salt to improve the adhesion between steel wire and rubber during storage and vulcanization.

The condensate of p-phenylenediamine and furfural can also improve the adhesion between steel wire and rubber.

Anti-aging 288 is obtained by condensation of p-phenylenediamine with octanol -2 or the corresponding ketone. It is an excellent anti-ozone agent, which is effective for aging caused by oxygen and deflection, and has a protective effect on atmospheric exposure and cracking. Suitable for natural rubber and synthetic rubber.

The anti-aging performance of the condensate of epoxy vegetable oil and p-phenylenediamine is equivalent to 40 10NA, but it does not volatilize and frost, and its solvent resistance is better than 40 10NA.

Epoxy resin curing agent

Using p-phenylenediamine as the curing agent of epoxy resin alone does not show any advantages, but the epoxy resin cured with p-phenylenediamine modified phenolic resin has good heat resistance and chemical resistance, and the heat resistance is 50℃ higher than that of phenolic resin cured product.

The reaction products of p-phenylenediamine with N-(4- hydroxy) maleimide and p-phenylenediamine with 2- amino -N- (hydroxyphenyl) succinimide, as curing agents of epoxy resin, have glass transition temperatures of 227℃ and 202℃ respectively, and can be used for printed circuit boards. The glass transition temperature of 4,4'-diaminodiphenyl sulfone cured product is 65438 044℃.

petroleum products additive

The condensate of p-phenylenediamine, dibutyl phosphate and dibutyl maleate as lubricating oil additive shows excellent anti-aging, anti-fatigue and load corrosion resistance when the dosage is 1%. The condensate of p-phenylenediamine, ethylene oxide and propylene oxide is better than Dissolvan44 1 1 as demulsifier for crude oil.

The condensate of p-phenylenediamine with sulfur, alkylphenol and paraformaldehyde can be used as detergent for gasoline and lubricating oil.

Carbon black treating agent

Carbon black treated with p-phenylenediamine is used as the developer of zinc oxide-based electrophotographic photosensitive paper. The contact time is 0.3 seconds, and the image contrast is sharp, so high quality Cowper can be obtained. The carbon black treated with p-phenylenediamine can be used as pigment, which can improve the blackness and the stability of slurry, and can be used for products with excellent properties such as ink.

Treating insulating paper

Treating electrical insulating paper with p-phenylenediamine can improve the heat resistance and reduce the loss of electrical, physical and mechanical properties caused by aging at 160℃, which can be used for insulation of high-power turbine motors.

flameproof

The reaction product of p-phenylenediamine and tetrabromophthalic anhydride is used for flame retardant of low density polyethylene. When 20% is added, the combustion speed decreases from 65,438 0.24 inch/min without flame retardant to 0.36 inch/min, and the elongation decreases from 3.0 inch without flame retardant to 0.25 inch.

The reaction product of p-phenylenediamine and dichlorophenyl phosphate is used for flame retardant of polyimide glass cloth reinforced plastics, and does not burn at 2000 ℉ (1093℃) 15 minutes.

other

Chelating resin produced by the reaction of p-phenylenediamine with EDTA dehydrate can be used to extract metals.

The condensate of p-phenylenediamine and glyoxal can be used as an anti-sticking agent in vinyl chloride polymerization kettle. When the dosage was 0.0 1g/m2, the adhesion of PVC decreased by 40 times.

In addition, p-phenylenediamine is used in blood microanalysis, complexometric titration indicator and combined with catechol as ultrafine particle developer.

P-phenylenediamine and maleic anhydride are used as aquatic biotoxic substances. After six months, the attached area of shellfish and algae was only 65,438+0%, while that of those untreated with toxic substances reached 65,438+0,000%.

P-phenylenediamine can also be used as a crosslinking catalyst for stabilizing unsaturated polyester resins (including polymerization inhibitors).

Emergency treatment

Skin contact: take off contaminated clothes and rinse skin thoroughly with soapy water and clean water. See a doctor.

Eye contact: Lift eyelids and rinse with running water or normal saline. See a doctor.

Inhalation: leave the scene quickly and go to a place with fresh air. Keep the respiratory tract unobstructed. If you have difficulty breathing, give oxygen. If breathing stops, give artificial respiration immediately. See a doctor.

Intake: Drink enough warm water to induce vomiting. See a doctor.

protective measure

Engineering control: tightly sealed to provide sufficient local exhaust. Provide safety shower and eye washing equipment.

Respiratory system protection: Wear a self-priming filter dust mask when the dust concentration in the air exceeds the standard. Self-contained breathing apparatus should be worn during emergency rescue or evacuation.

Eye protection: Wear safety glasses.

Physical protection: wear anti-virus infiltration overalls.

Hand protection: wear rubber gloves.

Other protection: Smoking and eating are prohibited in the workplace. Change work clothes in time. Don't drink before and after work, take a bath with warm water. Carry out pre-job and regular physical examination.

Packaging, storage and transportation

Packing method: plastic bag or double kraft paper bag, steel drum with full opening or middle opening; Fiberboard barrels, plywood barrels and cardboard barrels outside plastic bags or double-layer kraft paper bags; Ordinary wooden cases outside plastic bags or double kraft paper bags; Screw-capped glass bottles, iron-capped glass bottles, plastic bottles or ordinary wooden cases outside metal barrels (cans); Threaded glass bottles, plastic bottles or tin-plated steel drums (cans) are equipped with bottom plate boxes, fiberboard boxes or plywood boxes.

Precautions for storage and transportation: check whether the packaging container is complete and sealed before transportation to ensure that the container does not leak, collapse, fall or be damaged during transportation. It is strictly prohibited to mix with acids, oxidants, food and food additives. Exposure, rain and high temperature should be prevented during transportation. Store in a cool and ventilated warehouse. Stay away from fire and heat sources. The package is sealed. Should be stored separately from oxidants, acids and edible chemicals, and should not be mixed. Equipped with corresponding varieties and quantities of fire fighting equipment. The storage area should be equipped with suitable materials to control leakage. Strictly implement the "five pairs" of highly toxic substances

Safety/security information

Safety terminology

S23: Do not inhale gas/smoke/steam/spray.

Do not inhale gas/smoke/steam/spray.

S24/25: Avoid contact with skin and eyes.

Avoid contact between skin and eyes.

S28: Immediately after contact with skin, use a large amount of ... (specified by the manufacturer).

Immediately after skin contact, use a large amount of ... (specified by the manufacturer).

S36/37: Wear appropriate protective clothing and gloves.

Wear appropriate protective clothing and gloves.

S45: If you have an accident or feel unwell, seek medical attention immediately (show the label if possible).

If you have an accident or feel unwell, seek medical attention immediately (if possible, show the label).

S53: Avoid exposure-get special instructions before use.

Avoid contact and get special instructions before use.

S60: The material and/or its container must be treated as hazardous waste.

The substance and its container must be treated as hazardous waste.

S6 1: Avoid releasing into the environment. Please refer to special instructions/safety data sheets.

Avoid releasing into the environment, please refer to the special instructions/safe receiving instructions.

Risk terminology

R23/24/25: Toxic by inhalation, skin contact and swallowing.

Toxic by inhalation, skin contact and swallowing.

R36: Stimulate eyes.

Irritate the eyes.

R43: Skin contact may cause allergy.

Contact with skin may cause allergies.

R50/53: It is highly toxic to aquatic organisms and may cause long-term adverse effects on aquatic environment.

It is extremely toxic to aquatic organisms and may have long-term adverse effects on the water environment.

put right

reference data

[1] p-phenylenediamine. Huayuan Net [reference date 202 1-06-22]

[2] List of Three Carcinogens of the World Health Organization and List of Carcinogens of the International Agency for Research on Cancer (***502). Shaoxing Municipal Bureau of Market Supervision [citation date 2022- 1 1-22]

It turned out to be true that the whole family got a green card of more than 200 thousand RMB! (released by American immigrants)

Yimei advertisement

Zodiac Dragon: The "Dragon" of 1988 is changeable in wealth, marriage and career after the age of 34.

Birthday approval is only for entertainment advertisements.

Shanghai hydroquinone-purity 99.9%, domestic, factory direct sales.

People who care about hydroquinone are also watching.

Hydroquinone-can be used to prepare black and white developer, anthraquinone dye, azo dye, rubber antioxidant, stabilizer and antioxidant. The price is close to the people Welcome new and old customers to inquire for free.

Shandong yukang chemical co., ltd. advertisement

Amine compound

detail

triethylamine

Triethylamine is an organic compound with the chemical formula C6H 15N. It is a colorless oily liquid, slightly soluble in water, soluble in most organic solvents such as ethanol, ether and acetone, and is mainly used for dissolution.

aniline

Aniline, also known as aminobenzene, is an organic compound with the chemical formula of C6H7N. It is a colorless oily liquid. It decomposes when heated to 370℃, slightly soluble in water and easily soluble in ethanol and ether.

ethylenediamine

Ethylenediamine (EDA), chemical formula C2H8N2, is a typical aliphatic diamine, colorless or yellowish oily or watery.

Ursol

P-phenylenediamine, also known as Ursi D, is an organic compound with the chemical formula of C6H8N2, which is the simplest aromatic diamine.

dimethylamine

Dimethylamine is an organic substance with the chemical formula C2H7N. It is a colorless gas or liquid. When liquefied or compressed at a high concentration, it has a strong unpleasant smell of ammonia, and it has a fishy smell when it is extremely low.

diethylamine

Diethylamine is an organic compound with the molecular formula C4H 1 1N, which is a water-white flammable liquid with a strong ammonia smell and is mainly used for

trimethyl amine

Trimethylamine is an organic compound with chemical formula C3H9N, which is mainly used as disinfectant, natural gas alarm agent, analytical reagent and organic synthesis raw material, and also used in medicine, pesticide,

diphenylamine

Diphenylamine is an organic compound with the chemical formula of C 12H 1 1N, which is a white crystalline powder and is mainly used to manufacture antioxidant for lubricating oil.

m-phenylenediamine

M-phenylenediamine, also known as 1, 3- phenylenediamine, or MPD for short, is an organic compound with the chemical formula of C6H8N2. White needle-like crystal at room temperature, soluble in ethanol, water and chlorine.

P-nitroaniline

P-nitroaniline, also known as 4- nitroaniline, is an organic compound with the chemical formula of C6H6N2O2. It is yellow crystalline powder, insoluble in water, slightly soluble in benzene and soluble in ethanol.

ethylamine

Ethylamine is an organic compound with the chemical formula C2H7N. At normal temperature and pressure, it is a colorless gas with strong ammonia smell. It is soluble in water, ethanol,

Monomethylamine

Methylamine is an organic compound with the chemical formula CH3NH2. It is a colorless gas at normal temperature and pressure, and its specific gravity is 1.07 times that of air.

diisopropylamine

Diisopropylamine is an organic compound with the chemical formula of C6H 15N, which is mainly used as rubber accelerator, pharmaceutical intermediate, pesticide herbicide and surfactant.

isopropamide

Isopropylamine is an organic compound with the chemical formula C3H9N. Its aqueous solution is alkaline, its mixture with air is explosive, and it can react strongly with oxidant. Used as an insecticide,

xylidine

N, N- dimethylaniline is an organic compound with the chemical formula of C8H 1 1N, which is mainly used to prepare vanillin, azo dyes, triphenylmethane dyes,

Read more