Accelerated Chemistry 11

Synthesis of Tetramethylammonium
Pentaiodide

Achitphol Poollarp
Parinada Suriyaworakul
Phaphat Aowsathaporn
Wanwarisa Krittiyasrisumet
Phatsakorn Rodphol

#1101

Abstract :
 In this experiment, we demonstrate about synthesis of
tetramethylammonium pentaiodide. We also present the relation between mass
of reactant and product. We inserted 1.3 g of Iodine, 0.5 g of
Tetramethylammonium iodide and 12 ml of 95% Ethanol as reactant. After we
prepared all materials that we needs, we start to do the experiment by following
the step from the flow chart. We starts with mixing all ingredients together in
beaker. After that we put the beaker in the hot plate for ten minutes. For the next
ten minutes we leave beaker to cool down at the room temperature. Then,
Putting the beaker in an ice bath to catalyze process of crystallization for
another ten minutes. For the next step, we separated the crystal from the liquid
by using the Vacuum filtration. We have to beware of contamination in this
step. As the result, we got 0.94 g of Tetramethylammonium Pentaiodide. From
the result, a dark green mixture between flake crystal and powder are found.
From this experiment, Tetramethylammonium iodide is a limiting reagent that
can form 1.7624 g of product and Iodine is excess reagent which can formed
1.8149 g of product. Thus, 1.7624 g of product is a theoretical yield. Our
experiment got 53.27% yield.

Introduction :
Stoichiometry represents the relationship between the mass of the
reactant and the mass of the product. This concept is known as the conservation
of mass. In addition, the total mass of the reactant will equal to the total mass of
the product by balancing the chemical reaction. The ratio from the balancing
chemical equation can also use to calculate the amounts of reactant and
product. The number in front of the element species are called the stoichiometry
coefficient. The stoichiometry will make the ratio that can describe the relative
proportion of chemical in the reaction. This ratio are called the mole ratio. The
mole ratio are the factor that create the relation between the reactant and
product. The mole ratio can also use to calculate the mass of reactant and
product by using𝑚𝑚𝑚𝑚 = 𝑚𝑚𝑚𝑚 (𝑚)/
𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚ℎ𝑚 (𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚)[1]. In the chemical equation,
the reactant that limited the amount of product are called the limited reagent. In
addition, the limited reagent are the factor that use to determine how much
produce are made. The other reactant are called the excess reactant because it
will be some leftover after the limited is completely used up. The limited
reactant can be identified by using the 𝑚𝑚𝑚𝑚 = 𝑚𝑚𝑚𝑚 (𝑚)/
𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚ℎ𝑚 (𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚). The reactant that have the
smallest number of mole will be the limited reactant. Furthermore, the percent
yield is calculated by 𝑚𝑚𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚𝑚 = 𝑚𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚𝑚/
𝑚ℎ𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚𝑚 × 100. The theoretical yield is the amount of
product from the reaction and calculated by the limited reagent. In addition, it is
based on the calculation. The actual yield is the amount of product that get from
the real chemical reaction in lab.
Crystallization is a process that form a in the high organized structure known as
crystal from solution. This process is occur when the solution became the
supersaturated solution, which is when the solution cannot dissolve any more
solutes. After the solution start cool down, the crystal will start growing.
Crystallization can occur from the result of the precipitation. The crystal from
the crystallization process can may seem many different shape such as the
cubic, tetragonal, hexagonal, and trigonal.

In the experiment, the Tetramethylammonium (0.5g), Iodine(1.3g), and

Ethanol (12 ml) are mixed together in the beaker by using the stirring rod. Then,
the beaker are heated on the hot plate about 10 minutes in the fume hood. This
step with make the Tetramethylammonium dissolved in the solution. Then, the
beaker are removed from the hot plate and put it into the ice bath to allow the
beaker cool down. The crystals will start forming in this step. The solution in
the beaker with pour into buchner funnel on top of the suction flask that connect
to the pump. The solution are wash by the hexanes on the filtration paper inside
the buchner funnel . Then, air dry the product and weight the amount of
product.

Equipment:
- Stirring rod
- 50 mL beaker
- Filtration paper
- Petri dish
- Hot plate
- Weighing paper
- Electronic balance
- 50 ml graduated cylinder
- Fumehood
- Suction flask
- Ice bath
- Magnet bar
- buchner funnel
- air pump
- dropper

Material :
- 95% Ethanol 12 ml
- Iodine 1.3 g
- Tetramethylammonium iodide 0.5 g
- hexane

Data and Result :

Materials Amount
Tetramethylammonium Iodide 0.5 g
(limiting reagent)

Iodine 1.3 g

Ethanol 12 mL

Tetramethylammonium Pentaiodide 0.94 g

What do we get from experiment?

The product that we get from this experiment is tetramethylammonium
pentaiodide. We yielded 0.94 grams of the product. The product come out just
like in the picture below. The color is dark green and there is not a lot of crystal
in our product. The structure of the crystals are flakes and we suppose to get
that green flakes of crystal in our petri dish, but there are some errors, so all we
get is just powder of tetramethylammonium pentaiodide, but we can’t really see
the shape of the crystal.

Calculation:
C4H12N+I- + 2I2 = C4H12N+I5-
- Molecular weight of C4H12N+I-: 201.051g
- Molecular weight of 2I2: 253.808g
- Molecular weight of C4H12N+I5-: 708.667g
C4H12N+I-:
0.5𝑚 −3
1. mol = 201.051𝑚= 2.49 × 10

−3
2. g = (2.49 × 10 ) ×708.667 = 1.7624g C4H12N+I5-

I2 :
1.3𝑚 −3
1. mol = 253.808𝑚= 5.122 × 10
2. (5.122 × 10 −3) ÷2 = 2.561 × 10−3
3. g = (2.561 × 10−3 )×708.667 = 1.8149g C4H12N+I5-

Limiting Reagent: C4H12N+I-

Amount of excess reagent remaining:

0.5𝑚 −3
1. mol = = 2.49 × 10
201.051𝑚
2. (2.49 × 10 )×2 = 4.98 × 10−3
−3

3. g = (4.98 × 10−3 )×253.808 = 1.26g I2

Excess: 1.3g - 1.26g = 0.04g

𝑚𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚𝑚
% yield = × 100
𝑚ℎ𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚𝑚
0.94
= × 100
1.76458
= 53.27%

Analysis:
According to the result, the experimental yield of tetramethylammonium
pentaiodide is 0.94 grams. It is very low compared to the theoretical yield,
which is 1.76 grams. Therefore, the percent yield is only 53.27%. Almost half
of the amount of product is lost. This loss is predicted to be caused by the error
in our experiment. Because there is very a few crystal formed in our product
and mostly are small ones, so the mass might be less. When we did the
experiment, in the step of cooling the solution down, we might unnoticeably
disturbed the solution by moving the beaker a lot and quickly, so the solution
got shaken and disturbed. Another reason is when we filtrate the solution, we
did use a stirring rod to poke out all the solution, so that there won’t be any
solute remain in the beaker. From doing this, the process of crystallization has
been disturbed. Therefore the nice crystal flakes that we suppose to get are
ruined, so as a result only very a few crystals are formed (mostly are just
powder of the product) and the amount of product that we yielded is very low
too.

Conclusion :
0.94 grams of Tetramethylammonium Pentaiodide are formed by mixing
and reacting 0.5g of tetramethylammonium iodide with 1.3 grams of iodine and
12 mL of 95% ethanol solution. Small crystals are formed after the reaction had
occurred and time passed. Green pigment of product sticks together but some
don’t. No clear crystal is seen, but there are small white crystals formed
separately within the product, and they don’t seem to stick together.

Recommendation :
Improvement that we can do in the next lab is to be more careful when
the crystal is forming. This time we need to share 1 ice bath to 4 beaker of
chemical which we place our beaker. We need to move our beaker to create
space for other which cause interaction and interrupt crystallization process.
The time of heating chemical and cooling the chemical is too fast and may be
not enough for crystal to fully formed. We could pay more time on each step.

References
- Nijmeh J. & Tye M. (2015, Oct 15). Stoichiometry and Balancing Reactions.
Libretexts. Retrieved from:
https://chem.libretexts.org/Core/Inorganic_Chemistry/Chemical_Reactions/Stoichiom
etry_and_Balancing_Reactions [1]

Worklog
Name work
Tarn Equipment & Conclusion
Field Introduction
Pretty Result, Calculation & Analysis
Ping(p) Material & Recommendation
Mill Abstract & Procedure