EXPERIMENT 25: Synthesis of Cyclic Carboxylic Acid Anhydrides: Phthalic Anhydride Date: March 21, 2006 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 Brian Humphrey

TABLE OF REACTANTS AND PRODUCTS: Physical Properties of Reactants Compound MW Amount Phthalic Acid 166.14 100mg Acetic 102.09 200μL Anhydride Phthalic 148.11 Anhydride REACTIONS: Mmol 0.60 212 m.p.(°C) 210 128.5 b.p.(°C) 140 D 1.08 nD 1.3901

THEORECTICAL YIELD: 1 mol Phthalic Anhydride 148.1 g Phthalic Anhydride Phthalic Acid 0.00060mol ------------------------------ -----------------------1 mol Phthalic Acid = .00060mol / .889g 1 mol Phthalic Anhydride

EXPERIMENT 25: Synthesis of Cyclic Carboxylic Acid Anhydrides: Phthalic Anhydride Date: March 21, 2006 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. Brian Humphrey

EXPERIMENT 25: Synthesis of Cyclic Carboxylic Acid Anhydrides: Phthalic Anhydride Date: March 21, 2006 RESULTS -NOTES AND ADDENDUEM: • An infrared spectrum was obtained. Brian Humphrey

OBERVATIONS: o Weight of empty 3.0mL conical vial + spin vane o Weight of product + filter paper o Weight of product o Melting point of product 19.815g 0.2033g 0.182g 128.5°C

YIELD DATA: Actual Yield of Phthalic Anhydride Theoretical Yield of Phthalic Anhydride Percentage Yield of Phthalic Anhydride (0.182g ÷ 0.889) * 100% = PRODUCT ANALYSIS:

0.182g 0.00060mol / .889g 20.5%

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

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