Synthesis of Tetramethylammonium Pentaiodide

1104: Waritsaree, Papatsorn, Natdnai , Natchanon, Phuwadej, Prai

Abstract:
This experiment have three main chemicals called Iodine Ethanol and
Tetramethylammonium pentaiodide,C4H12IN + 2I2 --> C4H12I5N .
After the experiments we found that the chemicals, that we leave it to dry overnight is
turn out to be greyish and dark green colour and look like coals and dry without any liquid. We
found that limiting agent is Iodine and % yeild is %126.7

Discussion:
The factor that maybe cause us to failed the experiments is temperature maybe too
high,not enough stirring, wrong measurement of the chemicals,and the error of timing while heat
up the substances.
Calculated mole of Tetramethylammonium pentaiodide:
0.5g Tetramethylammonium pentaiodide x (1 mole Tetramethylammonium pentaiodide/201.07g
Tetramethylammonium pentaiodide) = 2.735 x 10-3 mole
Calculated mole of Iodine:
1.3g of Iodine x (1 mole Iodine/ 507.6g Iodine) = 2.561 x 10-3
Calculate mole of ethanol:
12 ml of ethanol x 1 mol of ethanol/ 46.07 ml of ethanol = 0.7467
Limiting Agent of Iodine:
2.561 x 10-3g of Iodine x (1 mole of Product C4H12I5N/2 mole of I2) x (708.6g of C4H12I5N/1 mole
of C4H12I5N) = 0.9074g of C4H12I5N
Limiting agent of this problem is iodine

2.735 x 10-3g of Tetramethylammonium pentaiodide x (1 mole of Product C4H12I5N/1 mole of

Tetramethylammonium pentaiodide) x (708.6g of C4H12I5N/1 mole of C4H12I5N) = 1.938g of
Tetramethylammonium pentaiodide

Percent yield
1.15g of C4H12I5N(actual) / 0.9074 g of C4H12I5N(theoretical) x 100 = 126.7

Objective:
To find out how to form the crystallization and to understand the findings of limiting
reagents.
Introduction:
This experiment is all about the formation of crystal by the composition of Iodine, Ethanol
and Tetramethylammonium Pentaiodide. Crystallization is how to form a solid crystal by a
homogeneous solution; it is a crucial technique to separate in solid from liquid (Maragret E.,
2004). This experiment could be complete by understanding method of mole and limiting
reagent. Mole is the usual measurement of amount and it could be found by divided the weight of
original substance together. The limiting reagent is the reactant that could define how much
products could be made in the process (Limiting Reagents and Percent Yield, 2015).

Experiment:
Material:
- Iodine 1.3g
- Ethanol 12 mL
- Tetramethylammonium pentaiodide 0.5g

Laboratory Apparatus:
- Stirring Rod
- Electronic Balance
- Filter paper
- Watch glass
- Beaker
- Goggles
- Gloves
- Lab coat
- Hot Plate
- Aluminium Floid
- Weighing Paper
- Fume Hood
- Ice bath

Procedure:
Synthesis of tetramethylammonium pentaiodide
C4H12IN + 2I2 --> C4H12I5N

1. Add 0.5 g C4H12IN to 50 mL beaker. Stirring Me4N+I-

2. Add iodine (1.3 g) and 95% ethanol (12 mL) in the same beaker
3. Heat the beaker and stirring for 10 minutes until the chemicals dissolve.
4. Heat at a low temperature
5. Remove from the heat and let the beaker to cool down
6. Crystal will form in this time
7. In room temperature, placing the beaker in an ice bath for 10 minutes.
8. Dry the product with air during the night
 9. Put it to rest
10. Hand in with your name labelled, the name of compound and the date.

Result
From the result of the experiment, the color of the crystal that formed was greyish green,
which the amount of the iodine was the variable that determine the color of the crystal. The
shape of the crystal was small pieces of flat object that formed after the chemical cooled down
from the process of making crystal. As for the weight, the calculated of the final weight of the
crystal was 1.70 g

Name of Substances Iodine 1.3g Ethanol 12 mL Tetramethylammoniu

m pentaiodide 0.5g

Weight 1.3 g. 12 mL 0.66 g.

Status Solid Liquid Solid

Appearance bluish-black, lustrous At room temperature, White solid.

solid. ethanol is a clear,
colorless, volatile
liquid

Conclusion
The experiment has fulfilled the objective of finding the method of crystallization and
understanding the result of limiting reagents. The researching on crystallization has been done to
proceed the experiment and calculation method. The limiting agent of this experiment is Iodine.
 When we compare our result to the limiting reagents we have calculated, percent yield of
Tetramethylammonium Pentaiodide is 126.7% which is higher than theoretical expectation. In
addition, the reactant presented in greyish and dark green colour revealing failure of the
experiment instead of having only dry green and white color. We hypothesize that the error might
came from external factors such as temperature or human error such as chemical weighing and
timing during the heat-up process. What we can improve the next experiment by control over
temperature, be more precise in measuring, and be more careful to time at the exact moment of
the process.

Reference
(1951, September). Retrieved from http://pubs.acs.org/doi/pdf/10.1021/ja01153a086
Chang, R. (1994). Chemistry. New York: McGraw-Hill.

1104
Waritsaree
Papatsorn
Natdnai
Natchanon
Phuwadej
Prai