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4-Amino diphenylamine

4-Amino diphenylamine

CAS: 101-54-2

Molecular Formula: C12H12N2

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4-Amino diphenylamine - Names and Identifiers

Name 4-Amino diphenylamine
Synonyms azosaltr
Azosalt R
C.I. 76085
C.I. 37240
blackbasep
Luxan Black R
fastbluersalt
FastblueRTbase
acnablackdfbase
Fast Blue R Salt
C.I. Developer 15
VARIAMINE BLUE RT
Acna Black DF Base
4-amino-diphenylamin
p-Aminodiphenylamine
4-Aminodiphenylamine
C.I. Oxidation Base 2
4-Amino diphenylamine
4-(Phenylamino)aniline
Variamine Blue RT Base
Benzenediamine, N-phenyl-
N-phenylbenzene-1,4-diamine
N-Phenyl-P-Phenylenediamine
4-Benzenediamine,N-phenyl-1
C.I. Azoic Diazo Component 22
N-Phenyl-1,41phenylenediamine
CAS 101-54-2
EINECS 202-951-9
InChI InChI=1/C12H12N2/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,13H2

4-Amino diphenylamine - Physico-chemical Properties

Molecular FormulaC12H12N2
Molar Mass184.24
Density1.09
Melting Point69 °C
Boling Point354 °C
Flash Point193°C
Water SolubilitySoluble in water at 20°C 0.6g/L. Soluble in (10 mg/mL) ethanol.
Solubility ethanol: soluble10mg/mL, clear, very dark red (Violet to brown to black solution)
Vapor Presure1 hPa
AppearanceForm Liquid, color Clear
ColorClear
BRN908935
pKa5.20±0.10(Predicted)
PH8.9 (0.5g/l, H2O, 20℃)
Storage ConditionStore below +30°C.
StabilityStable. Combustible. Incompatible with strong oxidizing agents, strong acids, plastics.
Refractive Index1.6266 (estimate)
Physical and Chemical PropertiesGray needle crystal.
melting point 72 ℃
boiling point 354 ℃
solubility soluble in organic solvents such as ethanol, ether, can also be soluble in acid, alkali solution, slightly soluble in water.
UseIntermediates for dyes and auxiliaries

4-Amino diphenylamine - Risk and Safety

Risk CodesR22 - Harmful if swallowed
R36 - Irritating to the eyes
R43 - May cause sensitization by skin contact
R42/43 - May cause sensitization by inhalation and skin contact.
R36/37/38 - Irritating to eyes, respiratory system and skin.
R20/22 - Harmful by inhalation and if swallowed.
R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
Safety DescriptionS26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36 - Wear suitable protective clothing.
S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.
S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. 
S60 - This material and its container must be disposed of as hazardous waste.
S36/37 - Wear suitable protective clothing and gloves.
UN IDsUN3077
WGK Germany3
RTECSST3150000
FLUKA BRAND F CODES8
TSCAYes
HS Code29215990
Hazard NoteIrritant
Hazard Class9
Packing GroupIII
ToxicityLD50 orally in Rabbit: 464 mg/kg LD50 dermal Rabbit > 5000 mg/kg

4-Amino diphenylamine - Upstream Downstream Industry

Raw Materials1-Chloro-4-nitrobenzene
Aniline
1-Chloro-4-nitrobenzene
Formic acid
Sodium sulfide
Hydrogen
Potassium carbonate
Nitrobenzene
Downstream ProductsN-isopropyl-N'-phenyl-p-phenylenediamine
N-1,3-dimethylbutyl-N'-phenyl-p-phenylenediamine

4-Amino diphenylamine - Nature

Open Data Verified Data

gray needle crystal. Melting Point 72 °c. Boiling point 354 °c. Soluble in organic solvents such as ethanol, ether, soluble in acid, alkali solution, slightly soluble in water. It is easy to oxidize and change color in air.

Last Update：2024-01-02 23:10:35

4-Amino diphenylamine - Preparation Method

Open Data Verified Data
  1. with P-nitrochlorobenzene and aniline in N-formyl aniline and potassium carbonate in the presence of direct condensation reaction, get 4 nitrodiphenylamine, after neutralization, water washing, and then sulfide alkali reduction (or hydrogenation reduction) water washing and distillation to obtain the finished product.
  2. with diphenylamine as raw material, after nitrosation in the organic solvent, to get the nitrosodiphenylamine. After the sulfide alkali reduction, to obtain the finished product.
Last Update：2022-01-01 10:52:47

4-Amino diphenylamine - Use

Open Data Verified Data

dye and rubber auxiliary intermediate, used in the synthesis of amine antioxidant, such as antioxidant 4010, 4010Na, 4020, etc.

Last Update：2022-01-01 10:52:47

4-Amino diphenylamine - Safety

Open Data Verified Data
  • toxic. Can be absorbed through the skin caused by poisoning, the pathological phenomenon similar to aniline. The production site should be well ventilated and the equipment should be closed. Operators should wear protective equipment to avoid direct contact with the human body.
  • sealed in iron drum, 200kg net weight per drum. Storage to fire, sun protection, moisture. According to the provisions of the storage and transportation of toxic chemicals.
Last Update：2022-01-01 10:52:48

4-Amino diphenylamine - Reference Information

Color index 37240
LogP1.82 at 20℃ and pH7
dissociation constant 5.45-5.47 at 20 ℃
NIST chemical information information provided by: webbook.nist.gov (external link)
EPA chemical substance information information provided by: ofmpeb.epa.gov (external link)
Use intermediates for dyes and auxiliaries
dye intermediates. Mainly used in the manufacture of antioxidant 4010NA,4020 and 668 and other important antioxidant; The manufacture of blue salt RT, acid red GR, disperse Yellow GFL and so on.
redox indicator (oxidized red, reduced colorless). Dye Intermediates. Drug. Photographs were taken. Print, coat dye.
production methods the production routes adopted at home and abroad are 4-nitrodiphenyl gum reduction method and 4-nitrosodiphenylamine reduction method. The former is divided into aniline and formamide method according to the raw materials used. And 4-nitrosodiphenylamine method, due to the diphenyl gum as raw material, also known as diphenylamine method. In addition, there is a method of reducing soap yellow. 1. Aniline process 4-nitrochlorobenzene was condensed with aniline (molar ratio 1:1.78) in the presence of copper catalyst (such as copper oxide and acid binding agent potassium carbonate) at 170-215 °c for 14h to give 4-nitrodiphenylamine, the yield was 90.6% based on p-nitrochlorobenzene. Raw material consumption quota: P-nitrochlorobenzene 1100kg/t, aniline 820kg/t, formic acid 500kg/t, potassium carbonate 650kg/t, sulfide alkali 1950kg/t. 2. Formyl aniline method formic acid and aniline condensation formyl aniline, and then with P-nitrochlorobenzene (formyl aniline dosage than the theoretical excess of 0%-100%), in the presence of acid binding agent potassium carbonate, at 120-195 ℃ reaction, 4-nitrodiphenylamine was obtained. The 4-nitrodiphenylamine obtained by the above two methods can be reduced by sulfide alkali or hydrogenation, or can be electrochemically reduced at 20-50 ° C. With a yield of 96%. 3.4-nitrosodiphenylamine method diphenylamine in the presence of acid, nitrosation with nitrite in solvent to obtain N-nitrosodiphenylamine, and then carried out translocation and rearrangement with anhydrous hydrogen chloride to obtain 4-nitrosodiphenylamine, the yield is 98%-99%. The temperature of nitrosation, translocation and rearrangement was 17-30 ℃. 4-nitrosodiphenylamine can be reduced at 50-100 ° C. With a sulfide base at atmospheric pressure, or it can be reduced by catalytic hydrogenation. In recent years, the research and development of hydrogenation reduction with nickel as Catalyst, the yield can reach 97%-98%. 4-nitrosodiphenylamine can also be obtained by electrochemical reduction in the yield of 96%. 4. Soap yellow Reduction Method: Add 55L of water, 23kg of 50% sodium sulfide and 6.6kg of sulfur into the reaction kettle, heat to boiling with stirring to dissolve all the materials, and then add 280L of water, 42.4 100% soap yellow, closed reactor, heated to 135 degrees Celsius, hot pressing 5H. After cooling to room temperature, filtered and rinsed with clean water until the filtrate was not yellow, 100% 4-aminodiphenylamine 19.9 was obtained. The yield was 90%.
category toxic substances
toxicity grade high toxicity
Acute toxicity oral-rat LD50: 464 mg/kg; Oral-mouse LD50: 464 mg/kg
stimulation data eyes-rabbits 100 mg/24 h moderate
flammability hazard characteristics open flame flammable; Thermally decomposed toxic nitrogen oxide gas
storage and transportation characteristics The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials
extinguishing agent sand and water
spontaneous combustion temperature >500°C
toxic substance data information provided by: pubchem.ncbi.nlm.nih.gov (external link)
Last Update：2024-04-10 22:29:15
4-Amino diphenylamine
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4-Amino diphenylamine
Raw Materials for 4-Amino diphenylamine
1-Chloro-4-nitrobenzene
Sodium sulfide
Downstream Products for 4-Amino diphenylamine
N-isopropyl-N'-phenyl-p-phenylenediamine
N-1,3-dimethylbutyl-N'-phenyl-p-phenylenediamine
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