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Dimethyl phthalate, Dimethyl isophthalate, Dimethyl terephthalate

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Identification
Molecular formula
C10H10O4
CAS number
Dimethyl phthalate: 131-11-3; Dimethyl isophthalate: 1459-93-4; Dimethyl terephthalate: 120-61-6
IUPAC name
dimethyl benzene-1,2-dicarboxylate;dimethyl benzene-1,3-dicarboxylate;dimethyl benzene-1,4-dicarboxylate
State
State

At room temperature, dimethyl phthalate is in liquid state, while dimethyl isophthalate and dimethyl terephthalate are in solid state.

Melting point (Celsius)
142.00
Melting point (Kelvin)
415.15
Boiling point (Celsius)
295.00
Boiling point (Kelvin)
568.15
General information
Molecular weight
194.18g/mol
Molar mass
194.1840g/mol
Density
1.1910g/cm3
Appearence

Dimethyl phthalate is a clear colorless liquid. Dimethyl isophthalate appears as a white solid, usually crystalline in form. Dimethyl terephthalate is a white crystalline solid with a slightly aromatic odor.

Comment on solubility

Solubility of Dimethyl Benzene-1,2-Dicarboxylate, Dimethyl Benzene-1,3-Dicarboxylate, and Dimethyl Benzene-1,4-Dicarboxylate

The solubility of the dimethyl benzene dicarboxylates (also known as phthalates) varies depending on their specific structure, leading to differences in their physical properties. These compounds, characterized by their carboxylate groups, exhibit significant interactions with solvents. Key points regarding their solubility include:

  • Polarity: The presence of two carboxylate groups in each compound increases polarity, enhancing solubility in polar solvents such as water.
  • Alcohol Compatibility: They tend to be more soluble in organic solvents like methanol and ethanol due to favorable dipole-dipole interactions.
  • Temperature Sensitivity: Solubility can vary with temperature; generally, an increase in temperature leads to greater solubility for most organic compounds.
  • Isomeric Variations: The solubility of the 1,2-, 1,3-, and 1,4-dicarboxylates can differ, where steric factors and molecular interactions play crucial roles in the solubility behavior.

Specifically, it is commonly observed that:

  1. Dimethyl Benzene-1,2-Dicarboxylate: Often shows higher solubility due to its rigid molecular structure allowing better interaction with polar solvents.
  2. Dimethyl Benzene-1,3-Dicarboxylate: Moderate solubility, influenced by the distance between the functional groups affecting molecular packing.
  3. Dimethyl Benzene-1,4-Dicarboxylate: Typically exhibits lower solubility because of more extensive intermolecular forces, making it less favorable for solvation in polar environments.

In summary, the solubility of these dimethyl benzene dicarboxylates is a complex interplay of molecular structure, polarity, and environmental conditions. As a result, understanding their solubility characteristics is vital for applications in various chemical and industrial processes.

Interesting facts

Exploring Dimethyl Benzene Dicarboxylates

Dimethyl benzene dicarboxylates, commonly recognized as dimethyl phthalates, are an intriguing class of compounds with varying structural isomers—specifically, the 1,2-, 1,3-, and 1,4- configurations.

Unique Features

  • Structural Diversity: Each isomer presents a distinct arrangement of carboxylate groups, leading to unique chemical and physical properties.
  • Industrial Applications: These compounds are primarily utilized in the production of plasticizers, which enhance the flexibility and durability of plastics.
  • Flavor and Fragrance: Certain isomers are also found in the formulation of perfumes and flavoring agents, contributing sweet and floral notes.
  • Toxicology: While their utility is vast, ongoing studies have raised concerns regarding their environmental impact and potential health effects, thus necessitating careful handling and usage guidelines.

Reactivity and Uses

Dimethyl benzene dicarboxylates are not only important in industrial settings but are also a crucial subject of study in organic chemistry due to their ability to participate in various reactions:

  • Polymerization: They are often featured in reactions to create high-performance polymer materials.
  • Biodegradation Studies: Researchers are investigating the breakdown pathways of these compounds in natural environments, aiming to understand their persistence and degradation mechanisms.
  • Analytical Chemistry: In techniques like gas chromatography, these compounds serve as important reference materials due to their well-defined structure.

As we study dimethyl benzene dicarboxylates, it is essential to acknowledge both their utility and their environmental implications. As chemists, understanding how these compounds interact within various contexts expands our knowledge of organic chemistry and its applications in real-world scenarios.

Synonyms
DIMETHYL BENZENEDICARBOXYLATE
26638-01-7
DTXSID70181178