95-80-7 Usage
Chemical Properties
2,4-Diaminotoluene is an organic compound with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. It is a synthetic, colorless to brown crystalline solid that is soluble in water, ethanol, ether and benzene. It is used primarily as an intermediate in the production of toluene diisocyanate, which is used to produce polyurethane.
Uses
2,4-diaminotoluene is used primarily in the production of 2,4-toluene diisocyanate, which is used in the production of polyurethane. It is used as an intermediate in the synthesis of dyes and heterocyclic compounds. 2,4-Diaminotoluene has been used as a developer for direct dyes, particularly to obtain black, dark blue, and brown shades, and to obtain navy blue and black colors on leather. Other applications include the preparation of impact resins, polyamides with superior wire-coating properties, antioxidants, hydraulic fluids, urethane foams, and fungicide stabilizers, and as a photographic developer (HSDB 2009).
Preparation
2,4-Diaminotoluene is prepared by hydrogenation of 2,4-dinitrotoluene using a nickel catalyst. Commercial samples often contain up to 20% of the 2,6-isomer.
Definition
ChEBI: 2,4-diaminotoluene is an aminotoluene that is para-toluidine with an additional amino group at position 2. It has a role as a metabolite. It derives from a p-toluidine.
General Description
A colorless crystalline solid. Toxic by ingestion and inhalation. Irritates skin and eyes. Slightly soluble in water and neutrally buoyant in water. Decomposes with emission of toxic oxides of nitrogen at high temperatures. Used in making dyes.
Air & Water Reactions
Soluble in water, alcohol and ether.
Reactivity Profile
2,4-Diaminotoluene 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. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. Reacts vigorously with oxidizing agents [USCG, 1999].
Health Hazard
2,4-Toluenediamine is a cancer-causing compound. Animal studies indicate sufficient evidence of its carcinogenicity. Oral applicationof this amine resulted in blood and liver cancers in rats and mice.The acute oral toxicity was moderate tohigh in test animals. It produced methe moglobinemia, cyanosis, and anemia. Theoral LD50 value in rats is 250–300 mg/kg.It is a mild skin irritant. The irritation effecton rabbits'eyes was moderate.Acute (short-term) exposure to high levels of toluene-2,4-diamine in humans has caused severe skin and eye irritation sometimes leading to permanent blindness. Other effects include respiratory problems, stomach gas, rise in blood pressure, dizziness, convulsions, fainting, and coma.
Fire Hazard
Noncombustible solid. It ignites when mixed
with red fuming nitric acid. Reactions with strong oxidizers and hypochlorites can be
violent.
Flammability and Explosibility
Nonflammable
Safety Profile
Confirmed carcinogen
with experimental carcinogenic data. Poison
by intraperitoneal and subcutaneous routes.
Experimental reproductive effects. Human
mutation data reported. A skin and eye
irritant. This material has a marked toxic
action upon the liver and can cause fatty
degeneration of that organ. When heated to
decomposition it emits toxic fumes of NOx.
See also other toluenediamine entries and
AROMATIC AMINES.
Potential Exposure
2,4-Diaminotoluene can be found in flexible and rigid polyurethane foams, upholstery, polyurethane coatings, for dyes used on textiles, leather, furs, in hair-dye formulations, sealants, adhesives gums and fibers. The substance is also commonly used when manufacturing other substances.
Carcinogenicity
2,4-Diaminotoluene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Shipping
UN1709 2,4-Toluylenediamine, solid or 2,4Toluenediamine, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3814 2,4-Toluylenediamine, solution or 2,4-Toluenediamine, solution, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification Methods
Recrystallise the diamine from water containing a very small amount of sodium dithionite (to prevent air oxidation), and dry it under vacuum. It also crystallises from *benzene. [Beilstein 13 IV 235.]
Incompatibilities
Strong acids; chloro formates, oxidizers.
Check Digit Verification of cas no
The CAS Registry Mumber 95-80-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 5 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 95-80:
(4*9)+(3*5)+(2*8)+(1*0)=67
67 % 10 = 7
So 95-80-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H10N2.ClH/c1-5-2-3-6(8)4-7(5)9;/h2-4H,8-9H2,1H3;1H
95-80-7Relevant articles and documents
Designing of Highly Active and Sustainable Encapsulated Stabilized Palladium Nanoclusters as well as Real Exploitation for Catalytic Hydrogenation in Water
Patel, Anish,Patel, Anjali
, p. 803 - 820 (2020/08/12)
Abstract: Encapsulated nanoclusters based on palladium, 12-tunstophosphoric acid and silica was designed by simple wet impregnation methodology. The catalyst was found to be very efficient towards cyclohexene hydrogenation up to five catalytic runs with substrate/catalyst ratio of 4377/1 at 50?°C as well as for alkene, aldehyde, nitro and halogen compounds. Graphic Abstract: Silica encapsulated Pd nanoclusters stabilized by 12-tungstophosphoric acid is proved to be sustainable and excellent for water mediated hydrogenation reaction with very high catalyst to substrate ratio as well as TON.[Figure not available: see fulltext.]
Depolymerization of Technical-Grade Polyamide 66 and Polyurethane Materials through Hydrogenation
Zhou, Wei,Neumann, Paul,Al Batal, Mona,Rominger, Frank,Hashmi, A. Stephen K.,Schaub, Thomas
, p. 4176 - 4180 (2020/11/30)
Chemical recycling provides a promising solution to utilize plastic waste. Here, a catalytic hydrogenative depolymerization of polyamide 66 (PA 66) and polyurethane (PU) was developed. The system employed Ru pincer complexes at high temperature (200 °C) in THF solution, and even technical-grade polymers could be hydrogenated with satisfactory yields under these conditions. A comparison of the system with some known heterogeneous catalysts as well as catalyst poisoning tests supported the homogeneity of the system. These results demonstrate the potential of chemical recycling to regain building blocks for polymers and will be interesting for the further development of polymer hydrogenation.
Superhydrophobic nickel/carbon core-shell nanocomposites for the hydrogen transfer reactions of nitrobenzene and N-heterocycles
Duan, Zhiying,Liu, Fangfang,Pang, Shaofeng,Su, Qiong,Wang, Yanbin,Xie, Xin,Zhang, Ping,Zhang, Yujing,Zhou, Feng
, p. 1996 - 2010 (2020/04/07)
In this work, catalytic hydrogen transfer as an effective, green, convenient and economical strategy is for the first time used to synthesize anilines and N-heterocyclic aromatic compounds from nitrobenzene and N-heterocycles in one step. Nevertheless, how to effectively reduce the possible effects of water on the catalyst by removal of the by-product water, and to further introduce water as the solvent based on green chemistry are still challenges. Since the structures and properties of carbon nanocomposites are easily modified by controllable construction, a one step pyrolysis process is used for controllable construction of micro/nano hierarchical carbon nanocomposites with core-shell structures and magnetic separation performance. Using various characterization methods and model reactions the relationship between the structure of Ni?NCFs (nickel-nitrogen-doped carbon frameworks) and catalytic performance was investigated, and the results show that there is a positive correlation between the catalytic performance and hydrophobicity of catalysts. Besides, the possible catalytically active sites, which are formed by the interaction of pyridinic N and graphitic N in the structure of nitrogen-doped graphene with the surfaces of Ni nanoparticles, should be pivotal to achieving the relatively high catalytic performance of materials. Due to its unique structure, the obtained Ni?NCF-700 catalyst with superhydrophobicity shows extraordinary performances toward the hydrogen transfer reaction of nitrobenzene and N-heterocycles in the aqueous state; meanwhile, it was also found that Ni?NCF-700 still retained its excellent catalytic activity and structural integrity after three cycles. Compared with traditional catalytic systems, our catalytic systems offer a highly effective, green and economical alternative for nitrobenzene and N-heterocycle transformation, and may open up a new avenue for simple construction of structure and activity defined carbon nanocomposite heterogeneous catalysts with superhydrophobicity.
