9 10-dihydro-9 10-ethanoanthracene- 11 12-dicarboxylic Anhydride Boiling Point

Okay, here is a comprehensive article on 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride, focusing on its boiling point characteristics, properties, synthesis, applications, and related considerations.

9,10-Dihydro-9,10-Ethanoanthracene-11,12-Dicarboxylic Anhydride: Properties, Synthesis, and Considerations Around Boiling Point

Introduction

9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride, often shortened to ethanoanthracene dicarboxylic anhydride or similar variations, is a complex organic compound. This compound is primarily used as a precursor in polymer synthesis and as a component in various advanced materials. Understanding its physical and chemical properties, particularly its boiling point, is crucial for its effective use in industrial and research applications. The boiling point affects the conditions under which it can be processed, purified, and incorporated into other materials.

Comprehensive Overview

Definition and Chemical Structure

9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride is a derivative of anthracene, modified by the formation of an ethano bridge across the 9 and 10 positions and the addition of a dicarboxylic anhydride group. Its chemical formula is C20H12O3. The compound consists of a central anthracene ring system that has been modified by the addition of an ethano bridge and a dicarboxylic anhydride moiety.

The ethano bridge creates a constrained three-dimensional structure, while the dicarboxylic anhydride provides a reactive site for further chemical modifications. This combination of structural features makes the compound valuable in the synthesis of polymers and other advanced materials.

Physical Properties

Understanding the physical properties of 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride is vital for predicting its behavior in various applications. Key properties include:

• Molecular Weight: Approximately 300.31 g/mol.
• Appearance: Typically appears as a white to off-white solid.
• Melting Point: The melting point is a more commonly reported property for this compound, often cited around 255-265°C.
• Solubility: Soluble in organic solvents such as chloroform, dichloromethane, and tetrahydrofuran. Its solubility in water is generally low.

Boiling Point Considerations

The boiling point of 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride is not typically a directly measured or frequently cited property for several reasons:

1. High Molecular Weight and Complexity: The compound has a relatively high molecular weight and complex structure, leading to strong intermolecular forces.
2. Thermal Decomposition: Before reaching a boiling point, many complex organic molecules tend to decompose. The high temperatures required to transition from a solid to a gaseous state can cause the compound to break down into simpler substances.
3. Experimental Challenges: Measuring the boiling point of high-melting solids can be experimentally challenging. Techniques such as distillation are often impractical due to the risk of decomposition.

Sublimation as an Alternative

Instead of boiling, many high-melting organic compounds, including 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride, undergo sublimation. Sublimation is the transition of a substance directly from the solid to the gaseous phase without passing through the liquid phase. This process can be used for purification and deposition of thin films.

• Sublimation Temperature: The sublimation temperature is a more relevant property for this compound. The compound can be sublimed under reduced pressure to purify it without causing decomposition. Typical sublimation temperatures range from 200-230°C under vacuum.

Synthesis of 9,10-Dihydro-9,10-Ethanoanthracene-11,12-Dicarboxylic Anhydride

The synthesis of 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride typically involves a Diels-Alder reaction between anthracene and maleic anhydride.

1. Diels-Alder Reaction:

   • Anthracene reacts with maleic anhydride in a Diels-Alder cycloaddition. This reaction combines the diene (anthracene) and the dienophile (maleic anhydride) to form the adduct, 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride.
   • The reaction is typically carried out in a solvent such as xylene or toluene at elevated temperatures (e.g., 140-180°C) to increase the reaction rate.
   • The reaction mixture is heated under reflux for several hours to ensure complete conversion.

2. Work-Up and Purification:

   • After the reaction is complete, the mixture is cooled to room temperature.
   • The product is often precipitated from the solution by adding a non-solvent such as hexane or diethyl ether.
   • The solid product is collected by filtration and washed with a suitable solvent to remove any unreacted starting materials or by-products.
   • Further purification can be achieved through recrystallization from a suitable solvent or by sublimation under reduced pressure.

Applications

9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride is a versatile compound with several important applications, primarily in the synthesis of polymers and advanced materials.

1. Polymer Synthesis:

   • Polyimides: It is used as a monomer in the synthesis of polyimides, which are high-performance polymers known for their excellent thermal stability, chemical resistance, and mechanical properties.
   • Polyesters: It can be reacted with diols to form polyesters with unique structural properties.

2. Advanced Materials:

   • Organic Electronics: Derivatives of this compound are used in organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs) due to their ability to modify the electronic properties of the materials.
   • Coatings and Adhesives: It is used in the formulation of coatings and adhesives to improve their thermal and mechanical properties.

3. Chemical Modifications:

   • Derivatization: The anhydride group can be easily modified to introduce various functional groups, allowing for the creation of a wide range of derivatives with tailored properties.

Safety and Handling

When working with 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride, it is essential to follow standard safety protocols for handling chemicals.

• Personal Protective Equipment (PPE): Always wear appropriate PPE, including gloves, safety glasses, and a lab coat.
• Ventilation: Work in a well-ventilated area or under a fume hood to avoid inhalation of dust or vapors.
• Storage: Store the compound in a cool, dry place away from incompatible materials.
• Disposal: Dispose of waste materials in accordance with local regulations.

Factors Affecting Thermal Behavior

Several factors can influence the thermal behavior of 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride. These include:

1. Impurities: The presence of impurities can affect the melting point and sublimation temperature. Impurities disrupt the crystal lattice, leading to a lower melting point.
2. Atmospheric Conditions: Sublimation is typically carried out under reduced pressure to lower the sublimation temperature and prevent decomposition. The presence of air can promote oxidation and degradation of the compound.
3. Heating Rate: The rate at which the compound is heated can also affect its thermal behavior. Rapid heating can cause decomposition, while slow heating allows for more controlled sublimation.

Tren & Perkembangan Terbaru

• Nanomaterials: Current research explores the use of 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride derivatives in the synthesis of nanomaterials. These materials are being investigated for applications in drug delivery, catalysis, and energy storage.

• Sustainable Chemistry: There is growing interest in developing more sustainable methods for the synthesis of this compound and its derivatives. This includes the use of bio-based starting materials and environmentally friendly solvents.

• High-Performance Polymers: Ongoing research focuses on incorporating this compound into high-performance polymers for aerospace, automotive, and electronic applications. These polymers are designed to withstand extreme conditions and provide enhanced performance.

Tips & Expert Advice

• Purification Techniques: If you need to purify 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride, consider sublimation under reduced pressure. This method effectively removes impurities without causing decomposition.
• Solvent Selection: When working with this compound, choose solvents carefully. Chloroform, dichloromethane, and tetrahydrofuran are good options, but always ensure the solvent is dry and free of impurities.
• Reaction Conditions: Optimize reaction conditions for Diels-Alder reactions. Temperature, solvent, and reaction time can significantly impact the yield and purity of the product.
• Storage: Store the compound in a tightly sealed container under nitrogen or argon to prevent oxidation and moisture absorption.

FAQ (Frequently Asked Questions)

Q: What is the primary use of 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride? A: It is primarily used in the synthesis of polyimides and other high-performance polymers, as well as in the creation of advanced materials for organic electronics and coatings.

Q: Why is the boiling point not a commonly reported property for this compound? A: The compound tends to decompose at high temperatures before reaching its boiling point, making sublimation a more practical method for purification and handling.

Q: How can I purify 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride? A: Sublimation under reduced pressure is an effective method for purifying this compound.

Q: What are the safety precautions I should take when working with this compound? A: Wear appropriate PPE, work in a well-ventilated area, and store the compound in a cool, dry place away from incompatible materials.

Q: Can this compound be used in organic electronics? A: Yes, derivatives of this compound are used in organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs).

Conclusion

9,10-Dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride is a valuable compound in polymer synthesis and advanced materials. While its boiling point is not a commonly reported property due to its tendency to decompose at high temperatures, understanding its thermal behavior, particularly its sublimation characteristics, is essential for its effective use.

By following best practices for synthesis, purification, and handling, researchers and engineers can harness the unique properties of this compound to create innovative materials with tailored properties.

How might future research further expand the applications of ethanoanthracene dicarboxylic anhydride in new and emerging fields?