Hydroxyethyl Formate (HCOOCH₂CH₂OH): Structure, Properties & Applications

Introduction of HCOOCH₂CH₂OH

Hydroxyethyl Formate (systematically, HCOOCH₂CH₂OH) is a bifunctional organic compound combining an ester (formate) and an alcohol (hydroxyethyl) group. Sometimes referred to in shorthand as “HCOOCH CH₂ H₂O” in web literature, it embodies the synergy of formic acid and ethylene glycol molecules. This structure grants it versatility across industrial, pharmaceutical, cosmetic, and green chemistry applications.

1. Molecular Structure & Physical Properties

• Chemical Structure: Formed by esterifying formic acid (HCOOH) with ethylene glycol (HO–CH₂–CH₂–OH), resulting in:

  H–C(=O)–O–CH₂–CH₂–OH


• Formula: C₃H₆O₃

• Appearance: A clear, colorless-to-pale-yellow liquid with a mild, sweet odor .

• Physical Traits: High boiling point (~175–180 °C), density ~1.18 g/cm³—denser than water.

2. Synthesis & Reactions

Synthesis

Synthesized via esterification—formic acid reacts with ethylene glycol using acid catalysts:

Typical conditions: 60–80 °C, azeotropic water removal.

Reactivity

• Under acidic or basic conditions, it undergoes hydrolysis, reverting to formic acid and glycol.

• In transesterification, it can exchange ester groups with other alcohols.

• Compatible with mild oxidation or dehydration reactions due to its ester-alcohol structure.

3. Chemical Behavior & Properties of HCOOCH₂CH₂OH

• Solubility: Moderately soluble in water; excellent in polar organic solvents .

• Hydrogen Bonding: The -OH group enables hydrogen bonding—key for solvent behavior and reactivity.

• Polarity: Its polar nature allows it to act as a solvent and mediator in reactions involving formic acid or esters.

4. Industrial & Commercial Applications

4.1 Green Solvent

Used in pharmaceuticals, coatings, and laboratory synthesis as a safer, biodegradable alternative to traditional organic solvents.

4.2 Cosmetics & Personal Care

Acts as a humectant and solvent in lotions and skincare products, improving moisture retention and ingredient stability.

4.3 Energy & Batteries

Explored for use in battery electrolytes and fuel cells, leveraging formate’s hydrogen-donating and proton-conducting capability.

4.4 Agricultural Chemicals

Serves as an intermediate in pesticide and herbicide synthesis via ester chemistry .

4.5 Pharmaceutical Intermediates

Used in drug-form formulations (e.g., sustained-release) and as a chemical intermediate due to its structural versatility .

5. Safety & Environmental Profile

• Hazard Traits: May cause skin or eye irritation; low acute toxicity .

• Handling Guidelines: Use in ventilated areas, wear protective gloves and goggles.

• Environmental Fate: Biodegradable—with mild acidity and organic breakdown products.

6. Hydrolysis & Redox Behavior

Hydrolysis

Reverse of the initial reaction: ester + water → formic acid + glycol.

Redox Role

While not strongly redox-reactive alone, formate can act as a mild reducing agent, useful in metal-catalyzed processes.

7. Analytical & Lab Uses

• Solvent Medium: Useful in analytical chemistry for polar reactions.

• pH Modulator: Adds controlled acidity in aqueous systems.

• Reference Substance: Included in material studies and NMR calibration.

8. Research & Emerging Frontiers

• Catalytic Systems: Being paired with nanocatalysts for eco‑friendly syntheses .

• Biomass Processing: Used in converting biomass into formate esters and renewable chemicals .

• New Material Science: Basis for smart resins/polymers with moisture or pH responsiveness .

9. Advantages & Challenges

Advantages

• Eco-friendly, biodegradable

• Dual-function chemistry (ester and alcohol)

• Solvent versatility in many industries

• Mild acidity with moderate reactivity

Challenges

• Requires careful temperature control during synthesis

• Hydrolysis may limit application in aqueous environments

• Cost and scalability depend on renewable feedstock availability

Conclusion

Hydroxyethyl Formate (HCOOCH₂CH₂OH) merges formic acid’s acidity with an alcohol’s versatility. With balanced polarity, hydrogen bonding, and green solvent status, it’s serving emerging roles in cosmetics, energy, and sustainable chemistry. Ongoing research into catalysis and material science underscores its growing relevance in chemical innovation.