Methyl formate

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Methyl formate
Methyl formate structure.png
Names
IUPAC name
Methyl formate
Preferred IUPAC name
Methyl formate
Other names
R-611
Properties
C2H4O2
Molar mass 60.05 g/mol
Appearance Colorless volatile liquid
Odor Pleasant, lemonade-like
Density 0.987 g/cm3 (15 °C)
0.98 g/cm3 (20 °C)
Melting point −100 °C (−148 °F; 173 K)
Boiling point 32 °C (90 °F; 305 K)
30 g/100 ml (20 °C)
23 g/100 ml (25 °C)
Solubility Miscible with acetone, chloroform, ethanol, methanol
Vapor pressure 476 mmHg (20 °C)
Hazards
Safety data sheet Simga-Aldrich
Flash point −19 °C
Lethal dose or concentration (LD, LC):
1,500 mg/kg (rat, oral)
1,622 mg/kg (rabbit, oral)
Related compounds
Related compounds
Ethyl formate
Methyl acetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methyl formate or methyl methanoate, is the methyl ester of formic acid, the simplest ester.

Properties

Chemical

Methyl formate can be hydrolyzed to methanol and formic acid using a strong acid.

Aminolysis of methyl formate gives formamide or dimethylformamide.

Physical

Methyl formate is a colorless organic liquid, with an ethereal odor, low surface tension and high vapor pressure. It has a melting point of −100 °C and boils at 32 °C. Methyl formate has a density of 0.97 g/cm3 at standard conditions. It is soluble in water (30 g/100 ml) and other solvents, such as acetone, diethyl ether, ethanol, ethyl acetate. The flash point of methyl formate is -19 °C and its auto-ignition temperature is 449 °C.

Availability

Methyl formate is available from chemical suppliers.

Preparation

Methyl formate can be synthesized by reacting anhydrous formic acid with dry methanol, over a strong desiccant, such as calcium chloride. Due to its low boiling point, methyl formate can be extracted via fractional distillation.

Industrially, it is prepared by via carbonylation of methanol, using sodium methoxide as a catalyst and pyridine as a temperature promoter, in an extremely dry medium. The smallest traces of water can disrupt the reaction.

CH3OH + CO → HCOOCH3[1]

This route however is uneconomical for the amateur chemist, thus the first method is cheaper and more accessible.

Projects

Handling

Safety

Methyl formate vapors may irritate lungs, so it's best to work in a well ventilated area. Since its boiling point is lower than the human body temperature, samples of methyl formate should not be kept too long in hand.

Storage

Due to its low boiling point, methyl formate should be stored in closed bottles, away from any source of heat or light, preferable in a fridge. This is mandatory during hot summers.

Disposal

Methyl formate can be safely burned.

References

  1. http://www.bjb.dicp.ac.cn/jngc/2004/2004-04-225.pdf

Relevant Sciencemadness threads