Synthesis of tetramethylammonium pentaiodide

By

Supapitch Ngamsangapong (Mook) 5961077

Anunya Phakhasetthakarn (Cherrie) 5961126

Arraya Tanyanurak (Peakpeak) 5961050

Napat Sienglue(Jaguar)5961198

Kulpassorn Nonthapiboon (Gail) 5961135

Chanyanut Pinyotanmakorn (Ning) 5961193

Abstract
In the experiment, Iodine(1.3 g.), Ethanol(12mL), and Tetramethylammonium
Iodine(0.5 g.), which is the limiting reagent, were used during the process in order to
synthesis the tetramethylammonium pentaiodide. After heated and cooled it down, the dark
green crystal formed in grain shape with weight measured 1.27 grams. Lastly, the percent
yield from this experiment is 71.72%.

Objective
The purpose of this experiment is to study chemical reaction between two starting material;
iodide and tetramethylammonium that perform crystallization​ ( CH 3 ) 4 N + I 5− and to
determine limiting reagent, percent of yield.
Introduction

​Chemical structure​ is the arrangement of chemical bonds between atoms in a

molecule. It’s about which atoms are chemically bonded to what other atoms with what kind
of chemical bond, together with any information on the geometric shape of the molecule
needed to uniquely identify the type of molecule. (Chemical structure,2017).

Chemical reaction ​is the process which one or more substances changed into other
new substance. Chemical equation uses chemical symbol to show what happened during a
reaction from reactants to products.To balance an equation, we change the number in front
of the formula (which is the coefficient) and make sure that the coefficient of each element in
the reactant and the product part are equal to each other.

In the calculation, the ​limiting reagent ​is the reactant used up first in a reaction, while
the ​excess reagent ​is the reactant in quantities greater than necessary to react with the
limiting reagent.

​Crystallization ​is a technique that has long been used in the purification of
substances.(Crystallization, n.d.), which means mass transfer occurs from the liquid solution
to a pure solid crystalline phase. It’s also the solidification of atom or molecule into a highly
structure form called a crystal. (Thoughtco., 2017). Crystal can be form from either pure melt
or from deposition of gas phase. The process of crystallization occur when atom or molecule
cluster together. If the cluster become stable, crystal growth can occur. The example of
crystallization are snowflake formation, gemstone crystal deposition, crystallization of honey
in a jar, etc. There are various methods to crystallize a substance, such as cooling a solution
or melt, evaporating solvent, sublimation. The most common process is to dissolve the
solute in a solvent in which it is at least partially soluble. The temperature of the solution is
increased to increase solubility, so the maximum amount of solute goes into solution. Next,
the warm or hot mixture is filtered to remove undissolved material or impurities. The
remaining solution (the filtrate) slowly cool to induce crystallization.

Material & Method

:Material:
1.) Iodine (0.6g.)
2.) Ethanol 95% (12ml.)
3.) 50 ml beaker
4.) stiring rod
5.) Hot plate
6.) Ice bath
7.) Vaccum filtration
8.) capped vial
9.) Hexane
10.) Tetramethylammonium iodide (0.5g)

Method:
1. Add to a 50 mL beaker tetramethylammonium iodide (0.5 g). Use a stirring rod to break up
clumps of Me4N+I-.
2. Add iodine (1.3 g) and 95% ethanol (12 mL).
3. In a fumehood, gently heat the beaker, with stirring, on a hot-plate 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 from 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.
8. Using vacuum filtration, collect the crystals and wash them with hexanes (5 mL portions
until filtrate dropping from funnel is colorless, max. 5 washings).
9. Air-dry the product with weigh.
10. Hand in a sample, in a capped vial, labelled with your name, the name of the compound
and the date to the lab instructor.

Result
The shape of the crystallization is grain, the color is dark green, starting material; iodide
1.3g, tetramethylammonium 0.5g, and the amount of yield is 1.27 g.

compound amount of compound

iodide 1.3 g

tetramethylammonium 0.5 g

Product amount of product

1.77 g. (Limiting reagent)

tetramethylammonium pentaiodide 1.81 g. (Excess reagent)
 Calculation

( CH 3 ) 4 N + I − + 2I 2 → ( CH 3 ) 4 N + I −5

Starter material (Mass)

Iodide: 1.3 g
Tetramethylammonium pentaiodide: 0.5 g
Filter paper: 0.56 g

Molecular weight

C = 12
H=1
N = 14
I = 12

( CH 3 ) 4 N + I − : ​4[ 12+ (1x 3) ] + 14 + 127 → 4 (15) + 141 = 201 g/ mol ​( CH 3 ) 4 N + I−

2I 2 : ​(127x 2) = 254 g/ mol 2I 2

Mole of each starting materials

Tetramethylammonium pentaiodide:
0.5 ÷ 201 ≈ 2.49 x 10−3
≈ 0.00249 mol (CH 3 ) 4 N + I −
Iodide: ​1.3 ÷ 254 ≈ 5.12 x 10−3 ≈ 0.00512 mol

Theoretical yield : ​ 1.77 g (CH 3 )4 N + I 3−

Actual Yield ​: ​1.27 g 2I 2

( CH 3 ) 4 N + I − :​ ​Limiting reagent
 1 mol (CH 3 ) 4 N + I − 1 mol (CH 3 ) 4 N + I −5 48 + 12 + 14 + (127 × 5) g (CH 3 ) 4 N + I −5
0.5 x 201 g (CH 3 ) 4 N + I −
x + − x
1 mol (CH 3 ) 4 N I 1 mol (CH 3 ) 4 N + I −5
+ −
+ −
1 mol (CH 3 ) 4 N I 1 mol (CH 3 ) 4 N I 5 709 g (CH 3 ) 4 N + I −5
≈ 0.5 x + − x
201 g (CH 3 ) 4 N I 1 mol (CH 3 ) 4 N I + − x
1 mol (CH 3 ) 4 N + I −5
≈ 1.77 g (CH 3 )4 N + I 5−

2I 2 :​ ​Excess reagent
1 mol (CH 3 ) 4 N + I − 1 mol (CH 3 ) 4 N + I −5 48 + 12 + 14 + (127 × 5) g (CH 3 ) 4 N + I −5
1.3 g 2I 2 x 254 g 2I 2
x 2 mol 2I 2
x 1 mol (CH 3 ) 4 N + I −5
+ −
1 mol (CH 3 ) 4 N + I − 1 mol (CH 3 ) 4 N I 5 709 g (CH 3 ) 4 N + I −5
≈ 1.3 g 2I 2 x 254 g 2I 2
x 2 mol 2I 2
x 1 mol (CH 3 ) 4 N + I −5
≈ 1.81 g (CH 3 ) 4 N + I 5−

Percent Yield
actual yield
% Yield = theoretical yield x 100
≈ 1.27 × 100 ≈ ​71.72 %
1.77

Discussion Question

We can calculate the amount of moles by the equation listed in the calculation
part. We have 0.5 grams of Tetramethylammonium iodide which were resulted in the
amount of 0.00249 mol and the iodide of 1.3 grams with the moles of 0.00512 mol
which we use those numbers to calculate the following reagent: the limiting reagent
and the excess reagent. The limiting reagent of the reaction is ( CH 3 ) 4 N + I − ,
resulted as theorical yield of 1.77 grams (CH 3 )4 N + I 5− and the excess reagent of is
2I 2 which have a actual yield of 1.81 grams (CH 3 ) 4 N + I 5− . The result of 2 reagents
lead as to the calculation of the percentage of the yield. We have 71.72% of yields,
the percent of yield of (CH 3 )4 N + I 5− can be calculate by actual yield divided by the
actual yield
theoretical yield and multiply with 100 as this written equation of theoretical yield
x 100.g

Conclusion

The product appearance is dark green in color. The amount of product are 1.77 and 1.81 g.
of tetramethylammonium pentaiodide. The limiting reagent is (CH3)4N+I-.
References

Chemical structure. (2017). Retrieved from

https://en.wiktionary.org/wiki/chemical_structure
Crystallization. (n.d.). Retrieved from
https://www.britannica.com/science/separation-and-purification/Exclusion-and-clathr
ation#ref619631
Thoughtco.. (2017). Retrieved from
https://www.thoughtco.com/definition-of-crystallize-605854