Chanikan Tangjitmungmun,Gam

Nattha Theevarajirasab, Nut

Suthida Termthong, Pufai
Pimploy Chankiew, Pim
Dec 18, 2015
Iodide Crystals

Abstract
The recrystallization was processed by the combination of tetramethylammonium
iodide (Me4N+I- ), 0.6 g of iodine, and 12 mL of 95% ethanol. The reactants were heated and
cooled afterward. We got the purple crystals by (CH3)4NI + I2 to (CH3)4NI3 which it is a
tetramethylammonium triiodide with 32.98% yield.

Object/Purpose
The purpose of this experiment was to observe the relationship between the structure
and color of the compound.

Introduction
Polyhalogen ion is polyatomic of halogens only. It could be classed into two classes
which is isopolyhalogen and heteropolyhalogen. The isopolyhalogen have both cation and
anion, but this experiment was focused on the isopolyhalogen anion, which is triiodide and
pentaiodide. They are composed of same element, but different numbers of iodine which
produce an effect of different structures. Triiodide is composed of three iodine atoms, while
pentaiodide has five iodine atoms. As shown in the figure (1) is triiodide, and figure (2) is
pentaiiodide.

(1) Structure of the triiodide anion (2) Structure of the pentaiodide anion
There are many methods to purification compound such as centrifugation, distillation,
evaporation, and recrystallization. One of the great purification laboratory techniques is to
recrystallize. This technique uncontaminated solids by taking advantage of the different
solubility properties of compounds. It removes the impurities out and get only the pure
compound by heat the solution to dissolving compound and solvent. To dissolve iodine with
ethanol, adding tetramethylammonium will make it become faster to attach with organic
compund as ethanol. As shown in the figure (3) is the structure of tetramethylammonium.

(3) structure of tetramethylammonium

When the solution is cooled down and become crystals that turn up during the
cooling, it has to be separated to get only the pure crystals by using suction filtration. Its a
technique for separating the solid from the liquid mixture, which allows a greater rate of
filtration. The suction filtration the fast application of reduced pressure pours the liquid
mixture through the filter paper in a Bchner funnel. While the liquid mixture is drawn by
forces through the filter paper in a gravity filtration.
In this experiment, we used the 0.6 g of iodide to do the crystallisation.

Procedure
1. Prepare 50mL beaker, weighing paper, spatula, and stirring rod (glass stick).
2. Put the weighing paper on the mass scale and set to zero.
3. Weight 0.5g tetramethylammonium by using a spatula and add in the beaker.
4. Break tetramethylammonium clumps by using stirring rod.
5. Weigh 0.6g iodine byusing spatula and add into the beaker
6. Use a stirring rod to break down the Me4N+I-
7. Add 12mL of 95% ethanol by using a graduated cylinder
8. Heat it on the hot plate. Do not make it too hot and being careful because it boil
easily.
9. Do this until dissolved.
10. Make sure that the liquid mixture is all dissolved.
11. Take the beaker out and wait until it become crystal. Do not disturb it.
 12. When crystal has formed, put on the ice bath to make it has more crystals.
13. During crystalization, set up the suction siltration.
14. Place the crystals to suction siltration.
15. Wash the crystals by hexane.
16. Open the vacuum filtration to suck liquid off.
17. Repeat steps 15-16 five times until liquid has no colour.
18. Bring the crystal out of the suction siltration.
19. Set the watch glass on the mass scale and set to zero.
20. Put the crystal on watch glass by using spatula. Weight the crystals and record it.
21. Replace the crystal into epi tube. And put the remainder on the waste.

Data/Results
The table shows the amount of compounds that use in experiment

Tetramethylammonium Iodide 0.5 g

Iodine 0.6 g

Final product Me4NI3 0.71g

Figure(4): The weight of crystal was 0.71grams.

Figure(5): 12 mL of Ethanol mix with 0.5g of tetramethylammonium iodide and Me 4 N + I

Calculations
0.5 g
201 g/mol = 2.49 10 3 Yield of Tetramethylammonium Iodide
0.6 g 3
126.904 g/mol = 4.73 10 Yield of Iodine
0.71 g
455 g/mol = 1.56 10 3 Yield of final product

Discussion
Some compounds have the same substances with different properties, because of
different amount of elements. The color of crystal also depends on the amounts of iodine
added. If the amounts of iodine is 1.3g, the color of crystal is green, while if adding 0.6g of
iodine, the color is purple. According to the result, the crystals are all in purple without any
green, because purple crystals will occur before green crystals. The iodine is combine with a
Tetramethylammonium pentaiodide and form (CH 3 ) 4 N + I 3 , which causes purple color.
Actual Yield is the amount of percent actually obtaned from a reaction. Theoretical
Yield is the amount of prduct that would result if all the limiting reagant reacted.
Actual Y ield
Percent Yield = T heoretical Y ield 100%
3
Percent Yield = 1.5610 3 100%
4.73 10
Percent Yield = 32.98%
 To isolate the solution by using suction filtration is faster and more efficient way to
filtrating the crystals. Meanwhile, the gravity filtration is the one use to remove solid
impurities from an organic liquid, while the suction filtration is use to collect a desired solid.
For example, the collection of crystals in a recrystallization procedure.
Iodine is less reactive than other elements in the Halogen group and takes time and
not easily to dissolve. It has a high atomic number, low toxicity, and easily attach with
organic compounds. Adding tetramethylammonium makes iodine become faster to attach
with ethanol which is oreganic compund. The reactants was heated during the procedure to be
easier to dissolve. However, using other solvent might generate different result.

Conclusion
The 0.5g tetramethylammonium iodide (Me4N+I-) with 0.6g of iodine is purified by
crystallization method into 0.71 g and the percent yield of crystal of tetramethylammonium
pentaiodide is 32.98%. Due to the results of the experiment, the crystal color is purple. It can
be assumed that different bonding structures of same element cause the different color of the
resultant.

References
1. Polyhalogen Compounds. (n.d.). Retrieved December 18, 2015, from
<http://www.learnnext.com/nextgurukul/wiki/concept/CBSE/XII/Chemistry/Polyhaloge
n-Compounds.htm>
2. Vacuum filtration. (n.d.). Retrieved December 18, 2015, from
<http://www.chem.ucla.edu/~bacher/General/30BL/tips/vacuum.html>
3. Recrystallization Technique. (n.d.). Retrieved December 18, 2015, from
<https://www.erowid.org/archive/rhodium/chemistry/equipment/recrystallization.html>
4. Suction Filtration. (n.d.). Retrieved December 18, 2015, from
<http://www.chem.yorku.ca/profs/hempsted/chemed/equipment/suction.html>
5. Recrystallization.(2013, October 2). Retrieved December 18, 2015, from
<http://chemwiki.ucdavis.edu/Physical_Chemistry/Physical_Properties_of_Matter/Solut
ions_and_Mixtures/Case_Studies/RECRYSTALLIZATION>
6. The Addition of Iodine to Tetramethylammonium Iodide.(n.d.). Retrieved December 18,
2015, from
 <http://pubs.acs.org/doi/abs/10.1021/j150502a025>

Tasks
1.Abstract: Nattha Theevarajirasab, Nut
2.Object/Purpose: Chanikan Tangjitmungmun,Gam
3.Introduction:Chanikan Tangjitmungmun,Gam
4.Procedure: Nattha Theevarajirasab, Nut / Chanikan Tangjitmungmun,Gam
5.Data/Results: Suthida Termthong, Pufai
6.Calculations: Suthida Termthong, Pufai
7.Discussion: Pimploy Chankiew, Pim / Suthida Termthong, Pufai
8.Conclusion: Nattha Theevarajirasab, Nut
9.References: Pimploy Chankiew, Pim