Insight into the hydrophobic functionalization of cellulose microfibrils using the Passerini three-component reaction

Area of Science:

• Materials Science
• Polymer Chemistry
• Green Chemistry

Background:

• Microfibrillated cellulose (MFC) is a sustainable biomaterial with potential applications.
• Functionalization of MFC is crucial for tailoring its properties and expanding its utility.
• Developing efficient and environmentally friendly modification methods is essential.

Purpose of the Study:

• To employ an aqueous, catalyst-free Passerini 3-component reaction (P-3CR) for functionalizing dialdehyde cellulose (DAC).
• To investigate the kinetics and efficiency of the P-3CR on DAC derived from MFC.
• To explore the impact of reaction parameters on the degree of substitution (DS) and introduce hydrophobicity.

Main Methods:

• Periodate oxidation of MFC to produce dialdehyde cellulose (DAC).
• Aqueous, catalyst-free one-pot Passerini 3-component reaction (P-3CR) for DAC functionalization.
• Characterization using 13C and 15N CP-MAS NMR, FTIR, and analysis of reaction kinetics and DS.

Main Results:

• The P-3CR reaction reached completion within 6-18 hours, demonstrating good atom economy.
• Variable degrees of substitution (0.08-0.37) were achieved by controlling DAC oxidation levels.
• Successful introduction of hydrophobic chains (C4-C11) onto cellulose, with cosolvent effects varying based on chain length.

Conclusions:

• The aqueous P-3CR is a versatile and efficient method for tailoring the functionalization of MFC.
• This approach enables the introduction of hydrophobicity to cellulose-based materials.
• The developed method offers a sustainable route for creating advanced cellulose materials.