EXPERIMENT 25: Synthesis of Cyclic Carboxylic Acid Anhydrides: Phthalic Anhydride

Date: March 21, 2006 Brian Humphrey

EQUIPMENT:

• 3.0mL conical vial w/ spin vane and reflux condenser

• Pasteur pipet
• Calcium drying tube
• Filter paper
• Sand Bath
• Ice Bath
• Hirsh funnel
• Hood

TABLE OF REACTANTS AND PRODUCTS:

Physical Properties of Reactants

Compound MW Amount Mmol m.p.(°C) b.p.(°C) D nD
Phthalic Acid 166.14 100mg 0.60 210
Acetic 102.09 200μL 212 140 1.08 1.3901
Anhydride
Phthalic 148.11 128.5
Anhydride

REACTIONS:

THEORECTICAL YIELD:

1 mol Phthalic Anhydride 148.1 g Phthalic Anhydride

Phthalic Acid 0.00060mol ------------------------------ ------------------------

1 mol Phthalic Acid 1 mol Phthalic Anhydride

= .00060mol / .889g
EXPERIMENT 25: Synthesis of Cyclic Carboxylic Acid Anhydrides: Phthalic Anhydride

Date: March 21, 2006 Brian Humphrey

PROCEDURE:

1. We weighed and added 100mg (0.60mmol) of Phthalic acid to a 3.0mL conical

vial containing a magnetic spin vane.

2. Next we added a 200μL (2.1mmol) of acid anhydride and then attached the vial to
a reflux condenser protected by a calcium drying tube.

3. We cautiously dispensed the acetic anhydride under the hood using an automatic
delivery pipet.

REACTION CONDITIONS:

4. The reaction solution was carefully positioned at the bottom in a sand bath and
heated to a temperature of 150 - 160°C for 30 minutes.

5. Allowed the mixture to cool to room temperature, whereupon the product

crystallized. Placed the product in an ice bath for 10 minutes and collected the
solid via vacuum filtration using a Hirsch funnel.

6. After vacuum filtration, we carefully rinsed the filter cake by drop-wise addition
of 0.4mL of cold hexane using a Pasteur pipet.

7. Completed the drying of the solid by placing the crystals on filter paper.

PURIFICATION AND CHARACTERIZATION:

8. After the product was dry, we weighed the product and calculated the percentage
yield, determined melting point, and obtain an infrared spectrum.
EXPERIMENT 25: Synthesis of Cyclic Carboxylic Acid Anhydrides: Phthalic Anhydride

Date: March 21, 2006 Brian Humphrey

RESULTS

-NOTES AND ADDENDUEM:

• An infrared spectrum was obtained.

OBERVATIONS:

o Weight of empty 3.0mL conical vial + spin vane 19.815g

o Weight of product + filter paper 0.2033g

o Weight of product 0.182g

o Melting point of product 128.5°C

YIELD DATA:
Actual Yield of Phthalic 0.182g
Anhydride
Theoretical Yield of Phthalic 0.00060mol / .889g
Anhydride
Percentage Yield of Phthalic
Anhydride 20.5%
(0.182g ÷ 0.889) * 100% =

PRODUCT ANALYSIS:

Product color was light pink and crystallizes in structure.

DISCUSSION AND REFERENCE:

We believe our product is Phthalic Anhydride, because our sample’s melting point
of 128.5C is within a 98.1% confidence range of the Phthalic Anhydride
experimentally determined melting point of 131C. Our IR spectrum with a strong
C═O at 2800cm-1 and peak and a prominent C═C peaks at 1690cm-1 and at
1430cm-1, further support our findings.
EXPERIMENT 25: Synthesis of Cyclic Carboxylic Acid Anhydrides: Phthalic Anhydride

Date: March 21, 2006 Brian Humphrey