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Toluene-2,4-diisocyanate

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Identification
Molecular formula
C9H6N2O2
CAS number
584-84-9
IUPAC name
1,3-diisocyanato-2-methyl-benzene;2,4-diisocyanato-1-methyl-benzene
State
State

At room temperature, Toluene-2,4-diisocyanate is in liquid form.

Melting point (Celsius)
22.00
Melting point (Kelvin)
295.00
Boiling point (Celsius)
251.00
Boiling point (Kelvin)
524.00
General information
Molecular weight
174.16g/mol
Molar mass
174.1570g/mol
Density
1.2200g/cm3
Appearence

Toluene-2,4-diisocyanate appears as a clear to pale yellow liquid. It sometimes has a sharp, pungent characteristic odor that can be irritating to the skin and eyes. When exposed to air, it has a tendency to react with moisture, which can cause it to form a solid crust on exposed surfaces.

Comment on solubility

Solubility of 1,3-diisocyanato-2-methyl-benzene and 2,4-diisocyanato-1-methyl-benzene

When considering the solubility of 1,3-diisocyanato-2-methyl-benzene and 2,4-diisocyanato-1-methyl-benzene, both compounds exhibit unique characteristics primarily due to their isocyanate functional groups. Here are some key points regarding their solubility:

  • Polar Nature: The presence of isocyanate groups (–N=C=O) introduces polarity, which can enhance solubility in polar solvents.
  • Hydrophobic Characteristics: The aromatic rings contribute significant hydrophobic character, likely reducing solubility in water.
  • Common Solvents: These compounds are generally more soluble in organic solvents such as:
    • Toluene
    • Chloroform
    • Dimethyl sulfoxide (DMSO)
  • Limited Water Solubility: Due to their hydrophobic properties, both compounds show very limited solubility in water, making them challenging to dissolve in aqueous environments.

It can be concluded that the solubility profile of these isocyanates is influenced strongly by their structure, where polarity contributes to solubility behaviors in organic solvents while limiting their interaction with water. As such, they are commonly utilized in various industrial applications where organic solubility is paramount.

Interesting facts

Interesting Facts about 1,3-Diisocyanato-2-methyl-benzene

1,3-Diisocyanato-2-methyl-benzene, commonly known as m-Tolylene diisocyanate (TDI), is an important industrial compound in the production of polyurethane foams. Here are some fascinating aspects:

  • Versatile Uses: TDI is primarily used in the manufacturing of flexible polyurethane foams, which are found in various applications like furniture, mattresses, and automotive seating.
  • Production Process: The synthesis of TDI involves the phosgenation of toluene diamine, making it crucial in chemical industries that require specific reaction conditions and safety measures due to its toxic nature.
  • Health and Safety: As an isocyanate, TDI is associated with respiratory problems and skin sensitization, necessitating the use of personal protective equipment (PPE) when handling the compound.
  • Pharmaceutical Potential: Recent studies have investigated the use of TDI in drug delivery systems due to its ability to form stable complexes with various therapeutic agents.

A Unique Isomer

Interestingly, TDI exists in two isomeric forms, and their specific distributions can affect the properties of the final polyurethane products. This highlights the importance of chemistry in tailoring material properties.


Interesting Facts about 2,4-Diisocyanato-1-methyl-benzene

2,4-Diisocyanato-1-methyl-benzene, often referred to as p-Tolylene diisocyanate (also TDI), is similarly vital in polyurethane production. Here are some key insights:

  • Different Isomer, Similar Uses: Like its counterpart, p-TDI is utilized extensively in producing polyurethane foams, showcasing the structural flexibility in isocyanate-based chemical synthesis.
  • Polymer Chemistry: The reaction of p-TDI with polyols results in versatile polyurethane materials that have significant applications in coatings, adhesives, and sealants.
  • Environmental Considerations: The production and use of p-TDI come with environmental responsibilities, as the compound is subject to regulations due to its potential ecological impact.
  • Innovative Research: Ongoing research explores the utilization of p-TDI for modifying existing polymers to enhance durability and resistance to extreme conditions.

Innovation and Challenges

The dual nature of TDI isomers presents both challenges and opportunities in polymer science, leading to innovative solutions in material engineering. As scientists explore the balance between functionality and safety, the importance of these compounds in industrial applications remains paramount.

Synonyms
DTXSID10953412
1,3-Diisocyanato-2-methylbenzene--2,4-diisocyanato-1-methylbenzene (1/1)
RefChem:1052853
DTXCID901381464
MFCD01778251
2,4-tolylene diisocyanate 2,6-tolylene diisocyanate
Diisocyanatotoluene; Methylphenylene ester Isocyanic Acid; Methyl-m-phenylene isocyanate; Methylphenylene isocyanate; Toluene Diisocyanate
SCHEMBL5613485
DB-225917
T0264
1,3-diisocyanato-2-methyl-benzene;2,4-diisocyanato-1-methyl-benzene
1,3-diisocyanato-2-methylbenzene;2,4-diisocyanato-1-methylbenzene
1,3-Diisocyanato-2-methylbenzene-2,4-diisocyanato-1-methylbenzene (1:1)