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HCOOCH CH2 H2O represents ethylene glycol monoformate, an ester formed when formic acid reacts with ethylene glycol. This organic compound consists of a formate group bonded to ethylene glycol, with water produced as a byproduct during synthesis. It serves as a chemical intermediate in various industrial processes.
The notation HCOOCH CH2 H2O describes ethylene glycol monoformate, though the spacing can create confusion. Breaking down the formula reveals its structure: HCOO (formate group) + CH₂CH₂OH (ethylene glycol minus one hydrogen) + H2O (water formed during the reaction).
The proper molecular formula is C₃H₆O₃, with the IUPAC name 2-hydroxyethyl formate. The CAS registry number is 628-35-3. This ester belongs to the formate family, characterized by the presence of a formic acid derivative bonded to an alcohol.
The confusion around this notation stems from non-standard chemical writing. Standard practice would write this as HCOOCH₂CH₂OH (ethylene glycol monoformate) or show the reaction as HCOOH + HOCH₂CH₂OH → HCOOCH₂CH₂OH + H₂O. The inclusion of “H2O” in the formula indicates the complete reaction equation rather than the compound itself.
You’ll encounter this compound primarily in organic synthesis labs and certain industrial processes where it acts as a reactive intermediate. Its dual functionality—containing both an ester group and a free hydroxyl group—makes it useful for further chemical modifications.
Ethylene glycol monoformate contains three distinct sections that determine its chemical behavior. The formate group (HCO-O-) provides ester functionality and mild acidity. The ethylene bridge (-CH₂CH₂-) offers structural flexibility. The terminal hydroxyl group (-OH) enables hydrogen bonding and further reactions.
The molecular weight calculates to 90.08 g/mol. The compound exists as a colorless liquid at room temperature with moderate volatility. Its structure allows it to participate in reactions typical of both esters and alcohols.
Compared to simple formate esters like methyl formate (HCOOCH₃, 60.05 g/mol) or ethyl formate (HCOOCH₂CH₃, 74.08 g/mol), ethylene glycol monoformate has higher molecular weight and an additional reactive site. This makes it more versatile but also more prone to side reactions.
The ester bond in ethylene glycol monoformate is susceptible to hydrolysis under acidic or basic conditions. The free hydroxyl group can undergo esterification, etherification, or oxidation depending on reaction conditions.
Ethylene glycol monoformate forms through a condensation reaction between formic acid and ethylene glycol. The reaction proceeds as:
HCOOH + HOCH₂CH₂OH ⇌ HCOOCH₂CH₂OH + H₂O
The mechanism follows typical esterification pathways. The carbonyl carbon of formic acid acts as an electrophile, attacked by the nucleophilic oxygen of ethylene glycol’s hydroxyl group. A tetrahedral intermediate forms, then collapses to release water and form the ester bond.
Acid catalysts (typically sulfuric acid or p-toluenesulfonic acid) speed up the reaction by protonating the carbonyl oxygen, making the carbon more electrophilic. The catalyst also helps protonate the leaving water molecule, facilitating its departure.
The reaction is reversible and reaches equilibrium. Water removal drives the reaction toward ester formation. Common techniques include Dean-Stark apparatus for continuous water removal, or use of molecular sieves as desiccants.
Temperature affects both rate and equilibrium. Reactions typically run at 60–100°C. Higher temperatures increase rate but may cause decomposition of formic acid to carbon monoxide and water. Lower temperatures slow the reaction but improve selectivity.
The presence of two hydroxyl groups on ethylene glycol creates selectivity challenges. Without careful control, ethylene glycol diformate (both hydroxyl groups esterified) can form. Controlling the stoichiometry—using excess ethylene glycol or limiting formic acid—favors monoformate production.
Ethylene glycol monoformate exhibits properties intermediate between simple formate esters and diols. Its boiling point sits around 174°C at atmospheric pressure, significantly higher than methyl formate (31.5°C) due to hydrogen bonding from the free hydroxyl group.
The compound shows good solubility in water and polar organic solvents like ethanol, acetone, and DMSO. This amphiphilic character—having both hydrophilic (hydroxyl) and hydrophobic (ester/alkyl) regions—makes it useful as a coupling solvent in mixed systems.
Density measures approximately 1.18 g/cm³ at 20°C. The refractive index is around 1.418. These physical constants help identify the compound and confirm purity in laboratory settings.
Stability varies with conditions. In neutral aqueous solution at room temperature, ethylene glycol monoformate remains relatively stable. However, exposure to acids or bases triggers hydrolysis back to formic acid and ethylene glycol. The rate depends on pH, temperature, and concentration.
The free hydroxyl group makes this compound reactive toward:
The ester group undergoes typical ester reactions including transesterification with other alcohols, reduction to corresponding alcohols with LiAlH₄, and aminolysis with amines to form formamides.
Ethylene glycol monoformate serves multiple roles in chemical manufacturing. Its primary use is as a reactive intermediate in organic synthesis. The dual functionality allows sequential reactions—one at the ester site, another at the hydroxyl group.
In polymer chemistry, it acts as a monomer or co-monomer for polyester synthesis. The free hydroxyl group can react with diisocyanates to form polyurethanes, or with diacids/dianhydrides to form polyesters. This creates polymers with specific properties tailored for coatings or adhesives.
Solvent applications take advantage of its polarity and hydrogen bonding capability. It dissolves both polar and moderately nonpolar substances, useful in formulations requiring mixed solubility characteristics.
Pharmaceutical synthesis occasionally uses ethylene glycol formate as a protecting group or as a starting material for drug intermediates. The formate can be cleaved under mild conditions, making it suitable for multi-step syntheses where protecting groups are needed.
The compound appears in some specialty chemical production routes, particularly where controlled hydrolysis or ester exchange reactions are needed. Its moderate reactivity provides a balance between stability during storage and reactivity during processing.
| Compound | Formula | Mol. Weight | Boiling Point | Key Difference |
|---|---|---|---|---|
| Methyl formate | HCOOCH₃ | 60.05 g/mol | 31.5°C | Simple formate ester; more volatile |
| Ethyl formate | HCOOCH₂CH₃ | 74.08 g/mol | 54°C | Slightly larger; fruity odor |
| Ethylene glycol monoformate | HCOOCH₂CH₂OH | 90.08 g/mol | 174°C | Contains free hydroxyl; dual functionality |
| Ethylene glycol diformate | (HCOO)₂CH₂CH₂ | 118.09 g/mol | ~177°C | Both positions esterified; no free OH |
Methyl and ethyl formate are simple esters with single functional groups. They’re more volatile and primarily used as solvents or flavor compounds. Their chemistry is straightforward ester chemistry without additional complications.
Ethylene glycol monoformate bridges simple esters and more complex molecules. The free hydroxyl adds reactivity and hydrogen bonding capability that simple formates lack. This makes it more useful for step-wise synthesis but also more prone to side reactions.
Ethylene glycol diformate represents complete esterification. It lacks reactive hydroxyl groups, making it more stable but less versatile for further reactions. It’s used where a stable, non-reactive formate ester is needed.
Ethylene glycol monoformate requires standard laboratory safety protocols. While less toxic than ethylene glycol itself, the compound can cause irritation to skin, eyes, and respiratory system upon exposure.
Store in tightly sealed containers away from strong acids, bases, and oxidizing agents. Cool, dry storage prolongs shelf life by minimizing hydrolysis. Typical storage temperature is 2–8°C for extended stability.
Handle in well-ventilated areas or under fume hood. Wear appropriate personal protective equipment including safety glasses, gloves (nitrile or neoprene), and lab coat. Avoid inhalation of vapors or mist.
In case of skin contact, wash immediately with soap and water. For eye contact, rinse with water for 15 minutes and seek medical attention. If inhaled, move to fresh air. If ingested, do not induce vomiting—seek immediate medical help.
Dispose according to local regulations for organic esters. Typically this involves collection in appropriate waste containers for incineration or chemical treatment. Do not pour down drains due to potential environmental impact and hydrolysis products.
Fire hazard is moderate. The compound is combustible but not highly flammable. Use water spray, foam, or CO₂ for firefighting. Avoid using water jets directly as they may spread the liquid.
It primarily serves as a chemical intermediate in organic synthesis and polymer production. The dual functionality (ester plus hydroxyl) allows sequential reactions in multi-step processes.
Under specific conditions, trace amounts might form from the reaction of formic acid and ethylene glycol in biological or environmental systems. However, it’s not a common natural product and is typically synthesized deliberately.
Ethylene glycol monoformate has an additional hydroxyl group, making it less volatile, more water-soluble, and capable of participating in more types of chemical reactions. Methyl formate is simpler with only ester functionality.
It’s moderately stable in neutral water at room temperature but will slowly hydrolyze over time. Acids and bases accelerate hydrolysis significantly, breaking it back down to formic acid and ethylene glycol.
Use standard lab safety equipment including gloves, safety glasses, and fume hood. Store in sealed containers at cool temperatures. Avoid contact with strong acids, bases, or oxidizers which can cause unwanted reactions.
