Chapter 5: Recrystallization of Benzoic Acid & Melting Point of Benzoic Acid

Joseph Personelli
Lab Partners: Dominic Gonzalez & Benjamin Lowry
Chemistry 2400
Instructor: Joseph Kappel
Laboratory Assistant: Stacey Mendigutia
January 13, 2015
Results:
i.

Structures:
O

HO

OH

Pure Benzoic Acid

ii.

CH3

Mehtanol

Measured/Collected Data:
Trial 1
Pure Benzoic
Acid& H2O
Filter Paper (g)
Benzoic Acid (g)

0.106 g
0.0600 g

Trial 2
Impure Benzoic
Acid & H2O
0.107 g
0.0600 g

Trial 3
Impure Benzoic
Acid, H2O &
Methanol
0.103 g
0.0604 g

Table 1: This table shows weights of the filter paper and the added benzoic acid
Trial 1
Pure Benzoic
Acid& H2O

Trial 2
Impure Benzoic
Acid & H2O

Trial 3
Impure Benzoic
Acid, H2O &
Methanol

Mass of Filter
paper after drying
(1st )
(2nd )
(3rd )
Final mass of
Filter Paper

0.151 (g)

0.118 (g)

0.122 (g)

0.135 (g)
0.130 (g)
0.130 (g)

0.116 (g)
0.115 (g)
0.115 (g)

0.119 (g)
0.119 (g)
0.119 (g)

Table 2: This table shows the weight of the filter paper with dried benzoic acid.

Starting to melt (C)

Pure Benzoic Acid
Impure Benzoic Acid
Trial 1 Product
Trial 2 Product
Trial 3 Product

Completely
Liquefied(C)
122 (C)
115 (C)
114 (C)
114 (C)
110 (C)

105 (C)
100 (C)
105 (C)
106 (C)
95 (C)

Table 3: This table shows the temperature that each substance started to melt and
when each substance became completely liquefied
iii.

Calculated Results:
Melting Point
Pure Benzoic Acid
Impure Benzoic Acid
Trial 1 Product
Trial 2 Product
Trial 3 Product

7 (C)
15 (C)
9 (C)
8 (C)
15 (C)

Table 4: The calculated melting points of each substance

Trial 1
Pure Benzoic
Acid& H2O
Mass of dried
benzoic acid (g)

0.024 (g)

Trial 2
Impure Benzoic
Acid & H2O
0.008 (g)

Trial 3
Impure Benzoic
Acid, H2O &
Methanol
0.016 (g)

Table 5: Mass of the dried benzoic acid that was left on the filter paper
Percent Yield
Trial 1
40 %
Pure Benzoic
Acid& H2O
Trial 2
13%
Impure Benzoic
Acid & H2O
Trial 3
26.5%
Impure Benzoic
Acid, H2O &
Methanol
Table 6: The calculated percent yield for trial 1, trial 2, and trial 3

iv.

Calculations:

Mass of dried benzoic acid = final mass of dried filter paper filter paper

Trial 1: 0.130(g) 0.106(g) = 0.024 (g)

Trial 2: 0.115(g) 0.107(g) = 0.008 (g)
Trial 3: 0.119(g) 0.103(g) = 0.016 (g)

Melting Point = Temperature substance becomes completely liquefied temperature

substance initially starts to melt

Pure Benzoic Acid: 122 (C) 105 (C) = 17 (C)

Impure Benzoic Acid: 115 (C) 100 (C) = 15 (C)
Trial 1 Product: 114 (C) 105 (C) = 9 (C)
Trial 2 Product: 114 (C) 106 (C) = 8 (C)
Trial 3 Product: 110 (C) 95 (C) = 15 (C)

Percent Yield = (mass of dried benzoic acid / mass of initial benzoic acid)* 100

v.

Trial 1 Product: (0.024 / 0.0600) * 100 = 40 %

Trial 2 Product: (0.008 / 0.0600) * 100 = 13 %
Trial 3 Product: (0.016 / 0.0604) * 100 = 26.5%

Discussion:

The purpose of this experiment was to dissolve pure benzoic acid and impure
benzoic acid and recrystallize it to get a new product of pure benzoic acid. A
purification technique was used to purify the impure benzoic acid. Dissolving the
impure benzoic acid in warm water and in one trial warm water and methanol did
this. The idea behind this was that the impurities would remain in the water solutions
and the benzoic acid would recrystallize together when it was quickly cooled by
being placed in a beaker of ice water. Pure benzoic acid has a melting point of 122
C. The trial 1 product, pure benzoic acid and water, had a melting point of 115 C. In
theory, trial 1 should have a very close melting point that of pure benzoic acid.
Because there was a 17C change in the melting point this could indicate some
impurities in the water. The trial 1 product of pure benzoic acid had a percent yield of
40% of the original weight of the pure benzoic acid that was added. This percent yield
was relatively higher when compared to the percent yield of trial 2 product and trial 3
product of 13% and 26.5% respectively. One possible reason for such a low percent
yield even for the trial 1 product is that some of the product could have missed the
filter paper in the vacuum filter apparatus and fell into the catch flask. To eradicate
this from happening again, larger pieces of filter paper could be used to line the
apparatus to catch all of the recrystallized benzoic acid.

vi.

Questions:

5-26: After isolating 45 mg of purified substance it can be calculated that 75% of the
substance was recovered. After receiving an addition of 8mg from the mother
substance there is an 88% percent total recovery.

6-5: Filter paper is a poor choice of surface to powder or crush a solid crystalline
sample before placing it into a capillary melting-point tube because the crushing of
the sample with the tube could cause the paper to mix into the powder. This could
result in a change of melting point if bits of the filter paper get mixed into the powder
substance.