Organic Chemistry- Esterification Using a Dean-Stark Trap

Esterification Using a Dean-Stark Trap

Description:  The esterification of benzoic acid and n-butanol in the presence of catalytic amounts of sulfuric acid is carried out in a reflux condenser. Water is a product of the reaction, and may be removed via the stopcock at the bottom of the Dean-Stark apparatus because water is denser than the ester product, and water is insoluble to all of the organic phases of the reaction. Water is removed this way to drive the reaction to greater completion than  would otherwise be possible.

Source: Clark Landis

Year:  2006  Vol: N/A  Page: N/A

Keywords: Esterification, N-butanol, Acid catalysis, Benzoic acid

Rating:

Hazard: High

• Skin irritation
• Skin corrosion hazard
• Serious eye damage hazard
• Short term aquatic toxicity hazard
• Flammability hazard
• Carcinogenicity hazard
• Specific toxicity hazard – inhalation hazard-respiratory system, central nervous system
• Electrical shock hazard
• Burn hazard
• Acute toxicity hazard – oral
• Corrosive to metals

Effectiveness: Average

• Results are observable with guidance
• Mild effects are seen by audience
• Hard to perceive results due to scale
• Moderate failure rate
• Time to results is high
• Good connection from demo to course material

Difficulty: High

• Use of toxic substances
• Demo at non-standard conditions
• Some timed manipulations
• Multi-step procedure with specific actions
• Manipulations require care
• Demos in which a display is used

Safety Precautions:

• Eye protection required
• Gloves required
• Perform in a well-ventilated area
• Use of UL approved three-prong plug and outlet
• Spill materials on hand
• ABC fire extinguisher on hand
• Chemically resistant surface recommended
• Sodium bicarbonate on hand
• Prevent release of reagents to the environment

Class: Organic Chemistry,  Organic Synthesis

Division: General, Organic Chemistry

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