Name | p-Phenylenediamine |
Synonyms | PDA C.I. 76060 JAROCOL PPD 4-AMINOANILINE fur black 41866 P-Phene Diamine 1,4-benzenediamie C.I. Developer 13 3,4-Dichloraniline 1,4-Diaminobenzene 1,4-BENZENEDIAMINE 1,4-DIAMINOBENZENE 1,4-Benzenediamine p-Phenylenediamine BENZENE-1,4-DIAMINE benzene-1,4-diamine P-PHENYLENE DIAMINE 1,4-PHENYLENEDIAMINE 1,4-Phenylenediamine para Phenylene diamine C.I. Oxidation Base 10 P-PHENYLENE DIAMINE FLAKE |
CAS | 106-50-3 |
EINECS | 203-404-7 |
InChI | InChI=1/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2 |
InChIKey | CBCKQZAAMUWICA-UHFFFAOYSA-N |
Molecular Formula | C6H8N2 |
Molar Mass | 108.14 |
Density | 1.135 g/cm3 (20℃) |
Melting Point | 138-143 °C (lit.) |
Boling Point | 267 °C (lit.) |
Flash Point | 156 °C |
Water Solubility | 47 g/L (25 ºC) |
Solubility | Soluble in alcohol, chloroform, ether and hot benzene. |
Vapor Presure | 1.08 mm Hg ( 100 °C) |
Vapor Density | 3.7 (vs air) |
Appearance | Powder or Flakes |
Color | White, gray, or purple to brown |
Exposure Limit | TLV-TWA 0.1 mg/m3 (ACGIH 1989); TWAskin 0.1 mg/m3 (MSHA and OSHA); IDLH25 mg/m3 (NIOSH); carcinogenicity: Animal Inadequate Evidence (IARC).. |
Merck | 14,7285 |
BRN | 742029 |
pKa | 4.17(at 25℃) |
PH | 9 (50g/l, H2O, 20℃) |
Storage Condition | Store below +30°C. |
Stability | Stable, but oxidizes when exposed to air. Incompatible with oxidizing agents. Store under inert atmosphere. |
Refractive Index | 1.6339 (estimate) |
Physical and Chemical Properties | melting point 138-143°C |
Use | Used as a fluorescent indicator, analytical reagent and coat stain, also used in the synthesis of dyes |
Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R36 - Irritating to the eyes R43 - May cause sensitization by skin contact R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R63 - Possible risk of harm to the unborn child R36/37/38 - Irritating to eyes, respiratory system and skin. R45 - May cause cancer R40 - Limited evidence of a carcinogenic effect R48/22 - Harmful danger of serious damage to health by prolonged exposure if swallowed. R67 - Vapors may cause drowsiness and dizziness R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
Safety Description | S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S28A - S24/25 - Avoid contact with skin and eyes. S23 - Do not breathe vapour. S53 - Avoid exposure - obtain special instructions before use. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
UN IDs | UN 1673 6.1/PG 3 |
WGK Germany | 3 |
RTECS | SS8050000 |
FLUKA BRAND F CODES | 8-10-23 |
TSCA | Yes |
HS Code | 29215119 |
Hazard Class | 6.1 |
Packing Group | III |
Toxicity | LD50 in rats (mg/kg): 80 orally, 37 i.p. (Burnett) |
Downstream Products | Diafen NN |
white to light purple-red crystals. Flammable. Turn purple-red or dark brown when exposed to air. Melting point 140 °c. Boiling point 267 °c. Flash point 155 ℃, can sublimate. Soluble in water, ethanol, ether, chloroform and benzene.
p-Nitroaniline is reduced with iron powder in acidic medium, and the reaction product is separated and distilled to obtain a finished product.
mainly used in the manufacture of azo dyes and sulfur dyes. It can also be used as a fur dye (e. G., fur black D, fur blue black DB, fur brown N2, etc.). It can also be used as a cosmetic hair dye, uresd, and can be used for the production of rubber antioxidant DNP, 288 and imaging agent.
color index | 76060 |
pH indicator color change ph range | NonQ uorescence (3.1) to orange/yellow Q uorescence (4.4) |
main applications | Nanoparticles, liquid crystal displays, chemical mechanical polishing, bottom antireflective coatings, electrochromic materials, inks, rubber, hair dyes, cosmetics, treatment of virus skin infection |
LogP | -0.84 at 20℃ |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
(IARC) carcinogen classification | 3 (Vol. 16, Sup 7) 1987 |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Overview | p-phenylenediamine (English p-Phenylenediamine), also known as Ursi D, is one of the simplest aromatic diamines. The pure product is white to lavender Red crystals turn purple or dark brown when exposed to the air. Slightly soluble in cold water, soluble in ethanol, ether, chloroform and benzene. It can be used to produce azo dyes, high molecular polymers, fur coloring agents, rubber anti-aging agents and photo developers. It is mainly used for aramid, azo dyes, vulcanized dyes, acid dyes, and can also be used as fur black D, fur blue black DB, fur brown N2, and rubber anti-aging agents DNP, DOP, MB production. It is also used as a raw material for cosmetic hair dye Ursi D series, gasoline polymerization inhibitor and developer. As a chemical stain, p-phenylenediamine is currently allowed to be used in hair dye production, but there are clear restrictions on its use. According to my country's "Cosmetic Hygiene Standards", the content of p-phenylenediamine in hair dyes shall not be higher than 6%. According to experts, although the content of p-phenylenediamine in the five "one-wash black" shampoos is between 1.1% and 1.4%, the high frequency of shampoo use and long-term accumulation can easily pose a threat to the health and safety of consumers. There is no documentary basis for whether p-phenylenediamine is a carcinogen; but p-phenylenediamine is organic and has drugs. It can be seen that the "Reagent Manual" (Second Edition) published by Shanghai Science and Technology Press in November 1985 is page 980. Foreign studies have shown that the incidence of breast cancer, skin cancer, leukemia, and skin cancer will increase in people who often dye their hair. In addition, p-phenylenediamine is also a commonly used sensitive reagent for testing iron and copper. Internationally, it is also used in aircraft paint, body armor pants, wall paint, etc. The development and production of p-phenylenediamine in China started earlier. Before 2003, the main manufacturers were concentrated in Jiangsu and Zhejiang, with a total of more than 20 enterprises. In 2004, the total production capacity of p-phenylenediamine in China was about 13,500 tons/year. Market research showed that the overall supply of p-phenylenediamine exceeded the demand. Since the 1990s, the demand has increased at a rate of 3%-5%. The difficulty of transportation of p-phenylenediamine and the pollution of p-phenylenediamine production have limited the production of p-phenylenedi. |
p-phenylenediamine rubber antioxidant | as the antioxidant variety with the largest consumption in the rubber industry, the production capacity and output of p-phenylenediamine rubber antioxidant in China have maintained rapid growth in recent years, with an average annual growth rate of 28.1% from 2002 to 2008, which is not much different from the 22.6% average annual growth rate of domestic tires. From the perspective of future market development, my country will still have a large demand for p-phenylenediamine rubber antioxidant. In recent years, with the eastward movement of the global tire industry, my country has become the world's largest tire producer, and major foreign tire companies are all In China, the average annual growth rate of domestic tire production has remained above 20% in the past five years. Despite the severe impact of the global financial crisis in the second half of 2008, tire production in 2008 was still as high as 546.15 million (data from the National Bureau of Statistics), an increase of about 7% year-on-year. According to the future development forecast of automobiles and tires, the domestic demand for p-phenylenediamine rubber antioxidant will maintain an average annual growth rate of about 5% from 2008 to 2010. Demand will increase from 2010 to 2015, with an average annual growth rate of about 8%. Therefore, the domestic demand for p-phenylenediamine rubber antioxidant will reach 98,000 tons and 144,000 tons respectively in 2010 and 2015. |
Uses | is an important dye intermediate, mainly used in the manufacture of azo dyes and vulcanized dyes, and can also be used in the production of fur black D and rubber antioxidant DNP, etc. Used as fluorescent indicator, analytical reagent and fur stain, and also used in the synthesis of dyes Mainly used in the manufacture of azo dyes and vulcanized dyes, it is also used in the production of fur black D, fur blue black DB, fur brown NZ and rubber antioxidant DNP, 288, DOP and DBP. p-phenylenediamine is also used as a raw material for cosmetic hair dye Ursi D, gasoline polymerization inhibitor and developer. It is mainly used for fur dyeing, and can also be combined with other dyes. It is often used as a mordant Verification of ammonia, copper, gold, hydrogen sulfide, iron, magnesium, oxidant, ozone, sulfur dioxide and vanadium, and determination of chromium. Fluorescent indicator for acid-base titration (pH≤ 3.1 without fluorescence, pH≥ 4.4 with orange-yellow fluorescence). Reducing agent. |
Production method | It is obtained by reducing p-nitroaniline with iron powder in acidic medium. Put iron powder into hydrochloric acid, heat to 90 ℃, and add p-nitroaniline under stirring. After addition, react at 95-100 ℃ for 0.5h, and then add concentrated hydrochloric acid dropwise to complete the reduction reaction. After cooling, neutralize with saturated sodium carbonate solution until PH7-8, boil and filter while hot, and wash the filter cake with hot water. The filtrate is combined with the washing solution, concentrated under reduced pressure, cooled and crystallized or distilled under reduced pressure to obtain p-phenylenediamine with 95% yield. |
category | pesticide |
toxicity classification | highly toxic |
acute toxicity | oral administration-rat LD50:80 mg/kg; Oral administration-mouse LDL0: 100 mg/kg |
stimulation data | skin-rabbit 250 mg/24 hours moderate |
explosive hazard characteristics | blastable when mixed with air |
flammability hazard characteristics | open flame, high heat, oxidant combustible; combustion releases toxic nitrogen oxide smoke |
storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidants and food additives |
fire extinguishing agent | carbon dioxide, sand, mist water. |
occupational standard | TWA 0.1 mg/m3; STEL 0.3 mg/m3 |
spontaneous combustion temperature | 567°C |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
immediate life-threatening and health concentration | 25 mg/m3 |