Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > N,N-Diethyl-p-phenylenediamine

N,N-Diethyl-p-phenylenediamine

N,N-Diethyl-p-phenylenediamine structure

N,N-Diethyl-p-phenylenediamine 

structure
  • CAS No:

    93-05-0

  • Formula:

    C10H16N2

  • Chemical Name:

    N,N-Diethyl-p-phenylenediamine

  • Synonyms:

    1,4-Benzenediamine,N1,N1-diethyl-;p-Phenylenediamine,N,N-diethyl-;1,4-Benzenediamine,N,N-diethyl-;N1,N1-Diethyl-1,4-benzenediamine;N,N-Diethyl-p-phenylenediamine;p-(Diethylamino)aniline;p-Amino-N,N-diethylaniline;N,N-Diethyl-4-aminoaniline;4-(Diethylamino)aniline;DPD;N,N-Diethyl-1,4-benzenediamine;N,N-Diethyl-1,4-phenylenediamine;PPD 89;4-Amino-N,N-diethylaniline;4-(N,N-Diethylamino)aniline;NSC 147488;4-(Diethylamino)phenylamine;1-N,1-N-Diethylbenzene-1,4-diamine

  • Categories:

    Cosmetic Ingredient  >  Hair Dyeing

Description

dark brown to black solid or liquid, depending upon room temperature


Reddish brown or black liquid. (NTP, 1992)


Reddish brown or black liquid. (NTP, 1992)

N,N-Diethyl-p-phenylenediamine Basic Attributes

164.25

164.25

202-214-1

0QQA4DFV2J

147488

1673

DTXSID2025058

Liquid|Pale yellow liquid

29215190

Characteristics

29.3

2.69620

Clear yellow-brown to dark brown Liquid or Low Melting Solid

0.988 g/cm3

144 °C

260-262 °C

>230 °F

n20/D 1.571(lit.)

H2O: <0.1 g/100 mL at 19 ºC

Freezer

pKa= 7.96 (conjugate acid)

Colorless needles; soluble in water, alcohol; insoluble in ether /Hydrochloride/

Insoluble in water.

Amines, Aromatic

N,N-DIETHYL-P-PHENYLENEDIAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Safety Information

III

6.1(b)

UN 2922 8/PG 2

1

25-34

26-36-45

SS9275000

T

Stability Air and light sensitive. Incompatible with strong oxidizing agents, strong acids.

P280-P301 + P310-P305 + P351 + P338-P310

H301-H314

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

This chemical is probably combustible. (NTP, 1992)

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 44 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P264, P270, P272, P280, P301+P310, P302+P352, P321, P330, P333+P313, P363, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

N,N-Diethyl-p-phenylenediamine's production and use as a dye(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from a structure estimation method(2), indicates that the non-protonated form of N,N-diethyl-p-phenylenediamine is expected to have moderate mobility in soil(SRC). Volatilization of N,N-diethyl-p-phenylenediamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.3X10-8 atm-cu m/mole(3), using a fragment constant estimation method(3). A pKa of 7.96(5) indicates N,N-diethyl-p-phenylenediamine will exist primarily in the protonated form at pH values of 5 to 9.Cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts. N,N-Diethyl-p-phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-3 mm Hg(SRC), determined from a fragment constant method(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from an estimation method(2), indicates that the non-protonated form of N,N-diethyl-p-phenylenediamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.3X10-8 atm-cu m/mole(4), developed using a fragment constant estimation method(4). A pKa of 7.96(5) indicates N,N-diethyl-p-phenylenediamine will exist primarily in the ionized form at pH values of 5 to 9. According to a classification scheme(6), an estimated BCF of 11(SRC), from an estimated log Kow of 2.2(7),and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-diethyl-p-phenylenediamine, which has an estimated vapor pressure of 3.0X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the vapor-phase in the ambient atmosphere. Vapor-phase N,N-diethyl-p-phenylenediamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). N,N-Diethyl-p-phenylenediamine absorbs light in the environmental spectrum and has the potential for direct photolysis(4).

The rate constant for the vapor-phase reaction of N,N-diethyl-p-phenylenediamine with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of approximately 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).

An estimated BCF of 11 was calculated for N,N-diethyl-p-phenylenediamine(SRC), using an estimated log Kow of 2.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for N,N-diethyl-p-phenylenediamine can be estimated to be 470(SRC). According to a classification scheme(2), this estimated Koc value suggests that the non-protonated form of N,N-diethyl-p-phenylenediamine is expected to have moderate mobility in soil. The pKa of N,N-diethyl-p-phenylenediamine is 7.96(3), indicating that this compound will exist in the cation form. Cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process because the cation is not expected to volatilize(SRC).

The Henry's Law constant for N,N-diethyl-p-phenylenediamine is estimated as 5.3X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that N,N-diethyl-p-phenylenediamine is expected to be essentially nonvolatile from water surfaces(2). N,N-Diethyl-p-phenylenediamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-3 mm Hg(SRC) determined from a fragment constant method(3).

Occupational exposure to N,N-diethyl-p-phenylenediamine may occur through inhalation and dermal contact with this compound at workplaces where N,N-diethyl-p-phenylenediamine is produced or used.(SRC)

Drug Information

FOLLOWING IN VIVO APPLICATION OF 1-(14)C-LABELED 4-AMINO-N,N-DIETHYLANILINE TO GUINEA PIG SKIN, BINDING TO EPIDERMAL PROTEINS WAS DEMONSTRATED, ALTHOUGH IT WAS RELATIVELY LABILE, & NO HAPTEN-AMINO ACID ADDUCT COULD BE ISOLATED.

AN AZOTOBACTER VINELANDII ELECTRON TRANSPORT-ACTIVE 0 R3 FRACTION RAPIDLY OXIDIZED N,N-DIETHYL-P-PHENYLENEDIAMINE.

SYMPTOMS: Symptoms of exposure to this compound may include skin irritation, dermatitis, and hemorrhaging. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. It is an irritant to the skin. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

4-amino-N,N-diethylaniline

N,N-Diethyl-p-phenylenediamine Use and Manufacturing

Methods of Manufacturing

Using N, N-diethylaniline as raw material, it is obtained by nitrosation, reduction and neutralization: the process is as follows: (1) For nitrosation, add 150kg water, 35kg N, N-diethylaniline and 72kg into the kettle Hydrochloric acid, cool to 0°C. At 0-5°C, add 50% sodium nitrite solution (made with 100% 18.5kg). After the addition, stir for half an hour and add 6 kg of salt. Stir for 2h. Filter to obtain p-nitroso-N, N-diethylaniline. (2) Reduction and neutralization Add 150kg water and 11kg hydrochloric acid to the kettle. Stir, add 41kg iron powder, cool to 15℃, add nitroso compound at 20-25℃. After the addition, add 5kg of iron powder and stir at 20-25℃ for 3h. Add 7kg of sodium carbonate, stir for 15min, and filter. The filter cake is washed with hot water. Add 50kg of liquid caustic soda (30%) and 15kg of salt to the filtrate and lotion, and let stand for layering. The upper material in the distillation kettle, collect the fractions by vacuum distillation at 120-150°C and a vacuum of 8kPa to obtain p-amino-N, N-diethylaniline.

Uses

Biochemical research

1,4-Benzenediamine, N1,N1-diethyl-: ACTIVE

Computed Properties

Molecular Weight:164.25
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:164.131348519
Monoisotopic Mass:164.131348519
Topological Polar Surface Area:29.3
Heavy Atom Count:12
Complexity:113
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of N,N-Diethyl-p-phenylenediamine

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.