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Analyzing 2-Methoxy-2-Methylpropane: Structure, Properties, and Applications

Feb 19, 2024

In the realm of organic chemistry, 2-methoxy-2-methylpropane, also known by its common name tert-butyl methyl ether (TBME), is a versatile and widely used compound. This article aims to provide a comprehensive analysis of 2-methoxy-2-methylpropane, exploring its molecular structure, physical properties, chemical properties, and diverse applications across various industries.

Molecular Structure:
2-Methoxy-2-methylpropane consists of a central carbon atom bonded to three methyl groups and one methoxy group (-OCH3). The molecular formula for this compound is C5H12O, and its structure can be represented as follows:Copy

     CH3    CH3

      |     |

   H – C – O – C – H

      |     |

     CH3    CH3

Physical Properties:

  • Appearance: Colorless liquid at room temperature
  • Odor: Mild, ethereal odor
  • Molecular Weight: 88.15 g/mol
  • Melting Point: -108.6 °C (-167.5 °F)
  • Boiling Point: 55.2 °C (131.4 °F)
  • Density: 0.74 g/mL at 25 °C (77 °F)
  • Vapor Pressure: 100 mmHg at 20 °C (68 °F)
  • Solubility: Miscible with water, alcohol, and most organic solvents

Chemical Properties:

  • Ether Functional Group: The presence of the ether functional group (-O-) in 2-methoxy-2-methylpropane makes it a relatively stable compound.
  • Reactivity: TBME is generally unreactive under normal conditions but can undergo certain reactions such as oxidation, hydrolysis, and acid-catalyzed cleavage.
  • Flammability: 2-Methoxy-2-methylpropane is highly flammable and has a low flash point, making it a potential fire hazard.

Applications:

  1. Fuel Additive:
    1. TBME is primarily used as an oxygenate in gasoline, helping to improve fuel efficiency and reduce emissions.
  2. Solvent:
    1. Due to its excellent solvency properties, 2-methoxy-2-methylpropane is widely used as a solvent in various industries, including paints, coatings, and adhesives.
  3. Chemical Intermediate:
    1. TBME serves as a key intermediate in the synthesis of other organic compounds, such as isobutylene and methacrylic acid.
  4. Pharmaceutical Excipient:
    1. In the pharmaceutical industry, TBME is employed as a solvent and penetration enhancer in certain drug formulations.
  5. Aerosol Propellant:
    1. 2-Methoxy-2-methylpropane is used as a propellant in aerosol products, such as hairsprays and insecticides.

Comparative Analysis Of 1-Methoxy-2-Methylpropane and 2-Methoxy-2-Methylpropane

Physical Properties:

Property1-Methoxy-2-Methylpropane (IBME)2-Methoxy-2-Methylpropane (TBME)
AppearanceColorless liquidColorless liquid
OdorMild, ethereal odorMild, ethereal odor
Molecular Weight88.15 g/mol88.15 g/mol
Melting Point-117.2 °C (-179.0 °F)-108.6 °C (-167.5 °F)
Boiling Point52.3 °C (126.1 °F)55.2 °C (131.4 °F)
Density0.73 g/mL at 25 °C (77 °F)0.74 g/mL at 25 °C (77 °F)
Vapor Pressure160 mmHg at 20 °C (68 °F)100 mmHg at 20 °C (68 °F)
SolubilityMiscible with water, alcohol, and most organic solventsMiscible with water, alcohol, and most organic solvents

Chemical Properties:

  • Reactivity: Both IBME and TBME are relatively unreactive under normal conditions but can undergo certain reactions such as oxidation, hydrolysis, and acid-catalyzed cleavage.
  • Ether Functional Group: The presence of the ether functional group (-O-) in both compounds makes them relatively stable.

Applications:

  • Fuel Additives:
    • IBME and TBME are both used as oxygenates in gasoline, helping to improve fuel efficiency and reduce emissions.
  • Solvents:
    • IBME and TBME are widely used as solvents in various industries, including paints, coatings, and adhesives.
  • Chemical Intermediates: 

Both compounds serve as key intermediates in the synthesis of other organic compounds.