Synthesis of tetramethylammonium triiodide

By
Priyakorn Nithikultanon 5961043
Phetvarisa Predavankul 5961051
Panita Mongkolajala 5961072
Bhu Koosongdham 5961073
Sakornchon Mattariganont 5961143
Archaree Charoenpanitch 5961224

Chemistry 11
Ms. Sorasaree Tonsiengsom

Mahidol University International Demonstration School

Semester 1 Academic Year 2016-2017
Abstract:
 The experiment that we conducted is for synthesis a Tetramethylammonium triiodide by
using 0.5 grams of tetramethylammonium iodide, 0.6 grams of iodine and 12 mL of ethanol as a
solvent. The process that has been done is called crystallization, a process that heat and cool
down to purify the crystal. The result of this laboratory is linked to the relation of reactant and
product of the chemical reaction.

Objective:
The purpose of this experiment is to study and create a deeper understanding of chemical
reaction between the reactant and the product by looking at how they change and also to perform
crystallization as a product of the experiment, which could be associated with the method of
determining yield and limiting reagent of this experiment.

Introduction:
Stoichiometry is a method of calculating the substance mol, gram and number of
molecules for each of the chemical substance (Khanacademy, 2017). This experiment is
calculated on (CH3)4N+I- + I2 -----> (CH3)4N+I3-, where (CH3)4N+I- + I2 is the reactant of
the synthesis of tetramethylammonium iodide and (CH3)4N+I3- is the product of the synthesis.
According to Chemical Formula (2008), the chemical equation has to be balanced before any
chemical reaction can happen. Crystallization is the process of where the solid crystals were
formed after the solution cools down (Reciprocal Net, 2004).

Materials:
1. 0.5 g of tetramethylammonium iodide
2. 0.6 g of iodine
3. 12 mL of 95% ethanol
4. 2 weighing papers
5. 2 spatulas
6. Electronic balance
7. 1 stirring rod
8. 1 50mL beaker
9. 50 mL Cylinder
10. 1 Magnetic bar
11. Hot plate
12. Fume hood
13. Ice Bath
14. 1 Filter paper
15. Vacuum filtration
16. 2*7 mL hexanes
17. 1 Petri dish
Procedure:
1. Add to a 50 mL beaker, tetramethylammonium iodide (0.5g). Use a stirring rod to break up
clumps of (CH3)4N+I-.
2. Add iodine (0.6 g) and 95 % ethanol (12 mL)
3. In the fume hood, gently heat the beaker on a hot plate with stirring for about 10 minutes until
tetramethylammonium iodide has dissolved.
4. Heat at a low temperature to prevent premature crystallization.
5. Remove from the heat and allow the beaker to cool undisturbed. (Agitating the solution can
cause smaller crystals to form which are more difficult to isolate and tend to occlude impurities)
6. The crystals should form during this time.
7. Once at room temperature, further cooling can be achieved by placing the beaker in an ice
bath for about 10 minutes. Only put the solution on ice if necessary. During this time, set up the
apparatus for suction filtration for filtration and washing of compounds.
8. Using vacuum filtration, collect the crystals and wash them twice with hexanes (2´7 mL).
9. Air-dry the product and weigh.
10. Hand in a sample, in a capped vial, labeled with your name, the name of compound and the
date to the lab instructor.

Results:
As the result the product turns out to be glistening shining purple crystal of 1.44 gram.
The weight of the product is increased. The product does not stick together as it can be blown off
with the wind if the product is placed in somewhere windy or just right under the air condition.

Calculations:
(CH3)4N+I- = 0.5 g * 1 mol (CH3)4N+I- / 201 g (CH3)4N+I- * 1 mol (CH3)4N+I3- / 1 mol
(CH3)4N+I- * 455 g (CH3)4N+I3- / 1 mol (CH3)4N+I3- = 1.132 g (CH3)4N+I3-
I2 = 0.6 g * 1 mol I2 / 254 g I2* 1 mol (CH3)4N+I3- / 1 mol I2 * 455 g (CH3)4N+I3- / 1 mol
(CH3)4N+I3- = 1.0748 g I2

% yield = Actual yield / Theoretical yield * 100 = 0.88 g / 1.0748 g * 100 = 81.87 %

Reactant 1 Reactant 2 Product

Chemical formula (CH3)4N+I- I2 (CH3)4N+I3-

Amount Gram 0.5 g 0.6 g 0.88

Amount Mol 0.00248756 0.0023622 0.0019

Excess Reagent Limiting Reagent

Discussion:
This is the analysis of the lab result which will include failures and successes we came
across during the experiment. The goal of this experiment is to perform a crystallization to be
able to see the change due to chemical reaction. We expect to learn and apply stoichiometry into
this experiment, especially in the calculation part.
In order to start, we need to have basic knowledges of chemical reaction, stoichiometry,
balancing equation, calculation, and crystallization. We also needed to be careful during
crystallization past because the solution has to be clear. It should not be contaminated by any
factors. If the solution is contaminated, there will be difficulties to form a crystal as something
has blocked its site to attach and to form into a crystal. As well as we need to keep the same
temperature and make sure that the solution is well placed, that it did not create any disturbance
to the crystallisation process. We can say that the crystallization is a fragile process where little
mistakes can lead to unsuccessful result.
In this experiment, the site for attaching was the magnetic bar that is placed into the
solution. The iron flakes are then attached to the bar in the crystallisation process. If the solution
moves, there is a high chance that the iron flakes would not attach to the bar properly.
The failures we have run into are wrong timing and wrong measurement of Ethanol. At
first, we measure the Ethanol with filter paper and get 1.55 grams, but for the second time we get
1.44 grams. We decided to measure again for two times to get the stable measurement of Ethanol
and finally we got 1.44 grams. We realized in the end that we put the Ethanol too close to the
electronic balance which increased the mass and made the mass not stable. For the second
failures, the wrong timing. We expected to put our beaker into the ice bath to cool them after
bringing them out of the fume hood. The appropriate time to measure is ten minutes. However,
we’ve put the beaker in the ice bath for too long which might cause a smaller crystal to form.
Even though we have followed the instruction, we still found that some errors were happening.
Our group member could have followed them more carefully, so that we can eradicate chance of
having small mistakes.

Conclusion:
At the end of this experiment , we have a glistened shining purple crystal as our result of
the experiment. The (CH3)4N+I3- was synthesized by the reactants, (CH3)4N+I-, which is the
excess reagent and I2, which is the limiting reagent. After the calculation, our product got the
mass of 0.88g (without mass of filter paper), 0.0019mole, and 81.87 % yield.

References:
Stoichiometry (article). (n.d.). Retrieved December 06, 2017, from
https://www.khanacademy.org/science/chemistry/chemical-reactions-stoichiome/stoichiometry-
ideal/a/stoichiometry
Balancing chemical equations. (n.d.). Retrieved December 06, 2017, from
http://www.chemicalformula.org/basic-chemistry/balancing-chemical-equations

(n.d.). Retrieved December 06, 2017, from

http://www.reciprocalnet.org/edumodules/crystallization/

Worklog:
Members Role

Archaree Lab intro + materials + procedures + discussion

Bhu Calculation + Discussion

Panita Conclusion + Discussion

Phetvarisa References + Discussion + Objective + materials

Sakornchon results + calculation +Abstract

Priyakorn Discussion + results