Experiment #1

1/26/15

Ilaria Caturegli
TA: Allison
Solids: Melting Point and Recrystallization

Introduction:
Recrystallization allows for purification of solids by heating the solid in boiling water and
then cooling to reform the crystals. Purification of impure benzoic acid and methylene bluecontaminated acetanilide will yield pure benzoic acid and acetanilide. After dissolution of the
compounds at elevated temperatures, impurities will be removed not only by heating but also by
gravity filtration to remove insoluble impurities and decoloration with carbon to remove colored
impurities. Formation of the solid as the solution cools and then isolation and drying of the
crystals will yield the pure compound. The percentage of recovery of the compound will be
calculated and recorded.
Determining a physical constant of a compound accurately is a useful step in
determining the identity of an unknown compound. Comparing measured physical constants,
such as the melting point, to tabulated values enables this characterization. The melting point
range of a substance is the temperature range at which the solid and liquid phases exist in
equilibrium. Pure substances often have a melting point range of +/- 1C; however, this range will
be altered if impurities are present. Impurities often decrease the melting point and broaden the
melting point range. The range over which the substance melts will be measured and recorded.
Experimental Procedure:
-For the recrystallization of benzoic acid, 30 mL of boiling water along with boiling stones was
added to 1.0 g of benzoic acid. More water may be added if there is difficulty in bringing the
benzoic acid into solution.
-Hot gravity filtration was performed to remove insoluble impurities from the mixture. Then the
solution was cooled in an ice bath to allow for recrystallization.
-For the recrystallization of methylene blue-contaminated acetanilide, about 40 mL of boiling
water along with boiling stones was added to 2.0 g of acetanilide. 0.2 g of decolorizing carbon
and 5 mL of cold water was added to the flask to remove the methylene blue.
-Filtration was performed to remove insoluble impurities from the mixture. Then the solution was
cooled in an ice bath to allow for recrystallization.
-A thermometer was calibrated by comparing the observed measurement to the actual value for
two temperature points, 0C and 100C.
-Using a DigiMelt, the melting temperature of naphthalene and two other pure compounds was
measured. The DigiMelt recorded the temperature data for when the sample began to melt and
stopped melting.

-The identity of an unknown compound was determined by measuring the melting point of the
sample with the DigiMelt and then comparing this measurement to tabulated values. The
measurement was first made both over a larger range and then a smaller range to determine the
melting point.
-The unknown compound was then mixed with two authentic samples, separately, in equal
proportions. The melting point of these mixtures was used to finalize the identity of the
compound.
Table of Reagents:

Compound
Napthalene
p-dichlorobenzene

Molecular Weight (g/mol) Melting Point

Physical Properties
(upper end) (C)
128.17
147

81 White crystalline solid with odor

53 Colorless solid with odor

Benzil

210.23

Cinnamic acid

148.16

132 White monoclinic crystals

Benzanilide

197.23

164 Solid

Succinic acid

118.09

186 White, odorless solid

p-nitrobenzoic acid
m-tolouic acid
Resorcinol

167.1189
136.15
110.1

94 Yellow solid

237 Light yellow crystalline powder

110 Solid
110 White solid

Benzoic acid

122.12

121 Colorless crystalline solid

trans-stilbene

180.25

122 Solid

Salicylamide

137.136

138 Solid

o-chlorobenzoic acid

156.57

138 Light brown solid

Adipic acid

146.14

150 White crystals

Benzenesulfonamide

157.19

151 Solid

p-toluamide

135.16

157 Solid

Salicylic acid

138.12

157 Colorless to white odorless

crystals

p-toluic acid

136.15

178 White crystalline solid

Compound

Molecular Weight (g/mol)

Physical Properties

Benzoic Acid

122.12 Colorless crystalline solid

Acetanilide

135.16 Odorless solid

Methylene Blue

319.85 Odorless dark green powder, contaminant

Water

18 Solvent