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p-Phenylenediamine

Outline P-phenylene diamine rubber antioxidant Chemical Properties Uses Production method Category Toxicity grading Acute toxicity Irritation data Hazardous characteristics of explosive Flammability and hazard characteristics Storage characteristics Extinguishing Media Professional standards
p-Phenylenediamine
p-Phenylenediamine structure
CAS No.
106-50-3
Chemical Name:
p-Phenylenediamine
Synonyms
nakoh;furrod;Nako H;rodold;ursold;Furro D;peltold;renalpf;Rodol D;Ursol D
CBNumber:
CB9852680
Molecular Formula:
C6H8N2
Formula Weight:
108.14
MOL File:
106-50-3.mol

p-Phenylenediamine Properties

Melting point:
139 °C
Boiling point:
267 °C(lit.)
Density 
1.135 g/cm3 (20℃)
vapor density 
3.7 (vs air)
vapor pressure 
1.08 mm Hg ( 100 °C)
refractive index 
1.6339 (estimate)
Flash point:
156 °C
storage temp. 
2-8°C
solubility 
Soluble in alcohol, chloroform, ether and hot benzene.
Colour Index 
76060
form 
Powder or Flakes
pka
4.17(at 25℃)
color 
White, gray, or purple to brown
PH
9 (50g/l, H2O, 20℃)
PH Range
NonQ uorescence (3.1) to orange/yellow Q uorescence (4.4)
Water Solubility 
47 g/L (25 ºC)
Merck 
14,7285
BRN 
742029
Exposure limits
TLV-TWA 0.1 mg/m3 (ACGIH 1989); TWA skin 0.1 mg/m3 (MSHA and OSHA); IDLH 25 mg/m3 (NIOSH); carcinogenicity: Animal Inadequate Evidence (IARC). .
Stability:
Stable, but oxidizes when exposed to air. Incompatible with oxidizing agents. Store under inert atmosphere.
Major Application
Nanoparticles, liquid crystal displays, chemical mechanical polishing, bottom antireflective coatings, electrochromic materials, inks, rubber, hair dyes, cosmetics, treatment of virus skin infection
InChIKey
CBCKQZAAMUWICA-UHFFFAOYSA-N
CAS DataBase Reference
106-50-3(CAS DataBase Reference)
NIST Chemistry Reference
1,4-Benzenediamine(106-50-3)
EPA Substance Registry System
1,4-Benzenediamine(106-50-3)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  T,N,T+,Xn
Risk Statements  23/24/25-36-43-50/53-63-36/37/38-45-40-48/22-67-52/53
Safety Statements  28-36/37-45-60-61-28A-24/25-23-53-26
RIDADR  UN 1673 6.1/PG 3
WGK Germany  3
RTECS  SS8050000
8-10-23
Autoignition Temperature 567 °C
TSCA  Yes
HazardClass  6.1
PackingGroup  III
HS Code  29215119
Hazardous Substances Data 106-50-3(Hazardous Substances Data)
Toxicity LD50 in rats (mg/kg): 80 orally, 37 i.p. (Burnett)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H301 Toxic if swalloed Acute toxicity,oral Category 3 Danger P264, P270, P301+P310, P321, P330,P405, P501
H311 Toxic in contact with skin Acute toxicity,dermal Category 3 Danger P280, P302+P352, P312, P322, P361,P363, P405, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H331 Toxic if inhaled Acute toxicity,inhalation Category 3 Danger P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H336 May cause drowsiness or dizziness Specific target organ toxicity,single exposure; Narcotic effects Category 3 Warning P261, P271, P304+P340, P312,P403+P233, P405, P501
H351 Suspected of causing cancer Carcinogenicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
H400 Very toxic to aquatic life Hazardous to the aquatic environment, acute hazard Category 1 Warning P273, P391, P501
H410 Very toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 1 Warning P273, P391, P501
H412 Harmful to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 3 P273, P501
Precautionary statements:
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P311 Call a POISON CENTER or doctor/physician.
P301+P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313 IF eye irritation persists: Get medical advice/attention.
P405 Store locked up.

p-Phenylenediamine price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 695106 p-Phenylenediamine anti-fade reagent 106-50-3 1g $76.7 2018-11-20 Buy
Sigma-Aldrich 695106 p-Phenylenediamine anti-fade reagent 106-50-3 5g $263 2018-11-20 Buy
TCI Chemical P0170 1,4-Phenylenediamine >98.0%(GC)(T) 106-50-3 25g $18 2018-11-22 Buy
TCI Chemical P0170 1,4-Phenylenediamine >98.0%(GC)(T) 106-50-3 250g $56 2018-11-22 Buy
Alfa Aesar A15680 p-Phenylenediamine, 97% 106-50-3 250g $38.9 2018-11-13 Buy

p-Phenylenediamine Chemical Properties,Uses,Production

Outline

P-phenylenediamine is one of the simplest aromatic diamine with the pure product being white to purple red crystals. It turns purple or dark brown color when being exposed to the air. It is slightly soluble in cold water, soluble in alcohol, ether, chloroform and benzene. It can be used for making azo dyes, high-molecule polymers and can also be used for the production of fur dyes, rubber antioxidants and photo developer and is mainly used for Kevlar, azo dyes, sulfur dyes, acid dyes as well as being used for the production of black fur D, black fur DB, brown fur N2 as well as rubber antioxidant DNP, DOP and MB. It can also be used as the raw material of cosmetic hair p-Phenylenediamine series, gasoline polymerization inhibitor and developer. P-phenylenediamine, as a chemical dye, is currently permitted for use in hair dye production, but there is a clear usage limits. According to China "Hygienic Standard for Cosmetics," the content of p-phenylenediamine in hair dyes should not exceed 6%. According to the introduction of experts, although five kinds of "Yixihei" shampoo have their p-phenylenediamine content being within 1.1% to 1.4%. However, the shampoo has high frequency of usage with long-term accumulation being prone to pose a threat to the health and safety of consumers. There is still no literatures regarding to whether phenylenediamine is carcinogenic or not; but there is literature basis regarding to that p-phenylenediamine drug is toxic organic. We can refer to Shanghai Science and technology press (November 1985) "reagent Handbook" (second edition), page 980. Overseas research has shown that for population being subject to frequent hair dying has the incidence of breast cancer, skin cancer and leukemia increased. In addition, p-phenylenediamine is also a common sensitive reagent for testing iron and copper. In the international arena, it is also used for aircraft coatings, bullet-proof clothing intima and walls paint.
The domestic development and production of p-phenylenediamine started earlier. Before 2003, the major manufacturers were concentrated in Jiangsu and Zhejiang area with the total number of enterprises being more than 20. In 2004 China's total production capacity of p-phenylenediamine can be about 13,500 tons/year. Market research has demonstrated that p-phenylenediamine in general exhibit a situation of supplying being more than the demand of the situation. Since the 1990s, the demand can increase annually at a rate of 3%-5%. The difficulty of transportation of phenylenediamine and pollution caused by p-phenylenediamine production pollution has also largely limited the production and yield of p-phenylenediamine.

P-phenylene diamine rubber antioxidant

As the antioxidant variety in rubber industry with the largest consumption, the production capability and yield of domestic production of p-phenylenediamine-class antioxidant has maintained rapid growth in recent years with the annual increasing rate from 2002 to 2008 being 28.1% which is comparable with the average annual growth rate of domestic tire (22.6 %). From the perspective of future market development, our country will still be a large demand for p-phenylenediamine-class rubber antioxidant. In recent years, with the eastward shifting of the global tire industry, China has become the world's largest tire producer with major foreign tire companies constructing joint ventures or wholly-owned enterprises in China. In the past five years, domestic tire production has an average annual growth rate being maintained at 20%. Although severely affected by the global financial crisis in late 2008, tire production in 2008 still was up to 546.15 million (NBS) with an increase of about 7%. According to the prediction of automobile tires, in 2008 to 2010, domestic demand for rubber phenylenediamine antioxidant was maintained at an average annual growth rate of about 5%; from 2010 to 2015, there is decrease on the demand with the average annual growth rate being about 8 %. Therefore, in 2010, 2015, the domestic demand for p-phenylenediamine rubber antioxidant will expected to reach 98,000 tons and 14.4 million tons.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Chemical Properties

It is white to purple red crystal. It will turn purple red or dark brown when exposure to the air. It can be dissolved in water, alcohol, ether, chloroform and benzene.

Uses

It is important dye intermediates and is mainly used in the manufacture of dyes and sulfur dyes; it can also be used for the production of fur black D and rubber antioxidant DNP, 288, DOP, DBP etc. P-phenylenediamine can also be used as the raw material of cosmetic hair dye “WuErsi D”, gasoline polymerization inhibitor and developer.

Production method

It can be obtained from the reduction of P-nitroaniline via iron in acid medium. Put the iron into hydrochloric acid and heat to 90 °C. Add with stirring of p-nitroaniline. After completion of the adding, have them reacted at 95-100 ℃ for 0.5h, and then add drop wise of concentrated hydrochloric acid so that the reduction reaction is completed. After cooling, use saturated sodium carbonate solution for neutralizing to PH7-8, after boiling and have hot filtration; use host water to wash the filter cake. The filtrate and washings were combined and subject to concentration under reduced pressure; after cooling crystallization or vacuum distillation, we can obtain the p-phenylenediamine with the yield of being 95%.

Category

Pesticide

Toxicity grading

Highly toxic

Acute toxicity

Oral-rat LD50: 80 mg/kg; oral-mouse LDL0: 100 mg/kg.

Irritation data

Skin-rabbit 250 mg/24 hours, moderate.

Hazardous characteristics of explosive

It is explosive when mixed with air.

Flammability and hazard characteristics

It is combustible upon fire, heat and oxidants with combustion releasing toxic fumes of nitrogen oxides.

Storage characteristics

Treasury: ventilation, low-temperature and dry; store it separately from oxidants and food additives.

Extinguishing Media

Carbon dioxide, sand and water spray.

Professional standards

TWA 0.1 mg/m³; STEL 0.3 mg/m3.

Chemical Properties

Off-white flakes

Chemical Properties

p-Phenylenediamines are white to slightly red crystalline solids. They have been described as gray “light brown” which may result from exposure to air.

Uses

p-Phenylenediamine is used for dyeing hairand fur, in the manufacture of azo dyes, inaccelerating vulcanization of rubber, and inantioxidants.

Uses

A hair dye component, paraphenylenediamine, as a contact allergen for treatment of inflammatory diseases.

Definition

ChEBI: A phenylenediamine in which the amino functions are at positions 1 and 4 of the benzene nucleus.

General Description

A white to purple crystalline solid (melting point 234 F) that turns purple to black in air. Flash point 309 F. Toxic by skin absorption, inhalation or ingestion. Used for production of aramid fiber, antioxidants, as a laboratory reagent, in photographic developing, and as a dye for hair and furs.

Air & Water Reactions

Oxidizes on exposure to air. The finely powdered base if suspended in air poses a significant dust explosion hazard. Soluble in water. Even as a solid will spot downwind areas purple/black (Roger Patrick, DuPont Engineer).

Reactivity Profile

p-Phenylenediamine is the stongest of the weak aromatic bases. p-Phenylenediamine neutralizes acids in weak exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Reacts readily with oxidizing agents .

Health Hazard

p-Phenylenediamine is a moderate to highlytoxic compound; the acute, subacute andchronic toxicity of this amine is greater thanthat of its ortho- and meta-isomers. The acutepoisoning effects in animals were manifestedby lacrimation, salivation, ataxia, tremor,lowering of body temperature, increasedpulse rate, and respiratory depression. Anintraperitoneal dose of 10.8 mg/kg (sus pended in propylene glycol) in male ratscaused the formation of methemoglobin tothe extent of 12.9% after 5 hours (Watan abe et al. 1976). The hydrochloride of thisamine has been reported to cause edemaof the head and neck in animals dosedwith 120–350 mg/kg. p-Phenylenediamine in hair dye formulations produced skinirritation and mild conjunctivial inflamma tion in a variety of test animals (Lloydet al. 1977). In guinea pigs, contact pro duced skin sensitization. Hair dyes con taining p-phenylenediamine damaged visionwhen applied into eyes. In addition, allergicasthma and inflammation of the respiratorytract resulted from exposure to higher con centrations. Reports in early literature citeseveral cases of human poisoning resultingfrom the use of hair dyes containingp-phenylenediamine. The toxic symptomsreported were liver and spleen enlargement,vertigo, gastritis, jaundice, atrophy of liver,allergic asthma, dermatitis, cornea ulcer,burning and redness in eyes, and presbyopia(the latter effects arising from using hair dyeson the eyebrows and eye lashes).
Tests for mutagenicity in Salmonellamicrosome assays (in vitro) were negative.With metabolic activation, upon oxidationwith hydrogen peroxide, most mutagenictests showed positive results. Tests forcarcinogenicity were negative, although itslightly increased the overall tumor ratein experimental animals. After oxidationwith hydrogen peroxide, the amine producedtumors in the mammary glands of female rats(Rojanapo et al. 1986).

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Contact allergens

PPD is a colorless compound oxidized by hydrogen peroxide in the presence of ammonia. It is then polymerized to a color by a coupling agent. Although a wellknown allergen in hair dyes, PPD can be found as a cause of contact dermatitis in chin rest stains or in milk testers. It is also a marker of group sensitivity to para amino compounds such as benzocaine, some azo dyes, and some previous antibacterial sulphonamides.

Safety Profile

Suspected carcinogen with experimental tumorigenic data. Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Mildly toxic by skin contact. A human skin irritant. Mutation data reported. Implicated in aplastic anemia, Can cause fatal liver damage. The p-form is more toxic and a stronger irritant than the 0and misomers. Wen used as a hair dye it caused vertigo, anemia, gastritis, exfoliative dermatitis, and death. Has caused asthma and other respiratory symptoms in the fur-dyeing industry. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use water, Con, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also other phenylenediamine entries and AMINES

Potential Exposure

p-Phenylenediamine has been used in dyestuff manufacture, in hair dyes; in photographic developers; in synthetic fibers; polyurethanes, and as a monomer and in the manufacture of improved tire cords. Also used as a gasoline additive and in making antioxidants.

First aid

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water or a slurry of activated charcoal in water; and induce vomiting. Do not make an unconscious person vomit.

Shipping

UN1673 Phenylenediamines (o-, m-, p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Crystallise the diamine from EtOH or *benzene, and sublime it in vacuo; protect it from light. The acetate has m 304o. [Beilstein 13 IV 104.]

Incompatibilities

Dust may form explosive mixture with air. A strong reducing agent. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, acid chlorides; acid anhydrides; chloroformates, and strong bases. Incompatible with organic anhydrides; isocyanates, aldehydes. Heat and light contribute to instability. Keep away from metals.

Waste Disposal

Controlled incineration whereby oxides of nitrogen are removed from the effluent gas by scrubber, catalytic or thermal device.

p-Phenylenediamine Preparation Products And Raw materials

Raw materials

Preparation Products


p-Phenylenediamine Suppliers

Global( 344)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Hefei TNJ Chemical Industry Co.,Ltd.
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View Lastest Price from p-Phenylenediamine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-04-10 p-Phenylenediamine
106-50-3
US $1.00 / KG 1KG 99% Factory have in stock thousand metric tons capacity Factory Chemwill Asia Co.,Ltd.
2018-12-18 p-Phenylenediamine
106-50-3
US $1.00 / kg 1kg 99% Customized career henan chemical co
2019-04-16 p-Phenylenediamine
106-50-3
US $10.00 / kg 1kg 99% 10 mt Hebei Guanlang Biotechnology Co., Ltd.

p-Phenylenediamine Spectrum


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