Honors Organic Chemistry Lab

Presentation
Spring 2016

Comparing Carbon Chain Lengths

on Ammonium Salt Catalysts

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General Reaction/ Work-up Procedure

1.

Add reactants to ball mill vial and seal

a.

150 mg Styrene Oxide

b.

35% molar equivalent of catalyst (Ammonium Iodide, Tetramethylammonium Iodide,

Tetrabutylammonium Iodide)
~ 2.25 g CO2 (s)
3 stainless steel balls

c.
d.

2.
3.

React in ball mill for 32 hours

Extract in ether with water work-up
a.
b.

2 x 2ml ether
2 x 2ml water

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Presenting: Ryan Muir

Introduction to Catalysts Used

+
+

Ammonium Iodide
Tetramethylammonium Iodide

Tetrabutylammonium Iodide

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Presenting: Ryan Muir

Why change the length of the Carbon Chain?

Increasing the size of the cation was expected to increase

the nucleophilic character of the of the oxygen where
indicated
Sterics
A more nucleophilic oxygen would ring close more readily
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Presenting: Ryan Muir

side peak
in the
1800s
Primary portion of the peak at
1788 where the product
carbonyl appears

Reaction of Styrene Oxide, CO2, Ammonium Iodide- IR

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Presenting: Ryan Muir

Reaction of Styrene Oxide, CO2, and Ammonium Iodide- GCMS

Presenting: Hope Guthier

5.8

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6.1

Reaction of Styrene Oxide, CO2, and Tetramethylammonium Iodide- GCMS

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Presenting: Ryan Muir

1.17

Reaction of Styrene Oxide, CO2, and Tetrabutylammonium Iodide- GCMS

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Presenting: Hope Guthier

In Summation...
Catalyst

Yield of Styrene
Carbonate

Styrene Oxide: Styrene

Carbonate

Ammonium Iodide

0.046 g

1 : 5.8

Tetramethylammonium
Iodide

0.072 g

6.1 : 1

Tetrabutylammonium Iodide

0.017 g

1.17 : 1

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Presenting: Hope Guthier

Comparing Positions in
the Ball Mill

55

Why change position?

Vial #6

Position from point of rotation to each

vial varies with location

Top vial travels on a longer path with

each cycle when compared to side and
bottom vials

Vial #1

Blank Vial

V = d/t
-

Vial #7

d- different for each vial

t- constant

Velocity of top vial > bottom

Therefore, impact force between vial and

ball varies

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Presenting: Ryan Muir

Slow motion video of inside of ball mill

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Presenting: Ryan Muir

Intermediates/ side products...

Reaction of Styrene Oxide, CO2, and Ammonium Iodide- GCMS- Vial 1 (back)
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Presenting: Ryan Muir

1.6

Reaction of Styrene Oxide, CO2, and Ammonium Iodide- GCMS- Vial 1 (Back)
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Presenting: Hope Guthier

Vial 1- Back
Observations during
Extraction:
Dark oily bubbles form
when the product is
extracted with ether and
agitated.
After water is added the
oily bubbles gather, pop,
and form a later
between the ether and
the water.
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3.2

Reaction of Styrene Oxide, CO2, and Ammonium Iodide- GCMS- Vial 6 (Top)
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Presenting: Hope Guthier

Vial 6- Top
Observations during Extraction:
When withdrawing with ether, the
solution was a distinct green color as
shown to the left.
This green color is most likely due to the
prior use of this ball mill vial with copper
based salts and not from the reaction
itself.

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1.3

Reaction of Styrene Oxide, CO2, and Ammonium Iodide- GCMS- Vial 7 (Bottom)
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Presenting: Hope Guthier

Vial 7- Bottom
Observations during
Extraction:
Vial 7 had a milky
appearance after
withdrawing from the ball
mill vial with ether.
After the addition of
water the milkiness
began dissipating and
mostly settled in the oliy
in between layer.
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1.4

Reaction of Styrene Oxide, CO2, and Ammonium Iodide- GCMS- Blank (Front)
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Presenting: Hope Guthier

Blank Vial- Front

Observations during Extraction:
Vial blank, after withdrawing from the ball
mill vial, had a large volume of dark sediment
(not shown).
After the water was added, a thick dark oil
layer formed between the ether and the water
layers; it is noticeably darker than the oil
layers previously shown.

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Yields/Ratios
Vial #

Weight of Styrene Carbonate

(g)

styrene carbonate%
((st. carb/tot)*100)

Ratio (Intermediates :
Desired)

1 (back)

0.109 g*

62%*

1 : 1.9*

6 (top)

0.125 g

65%

1 : 3.2

7
(bottom)

0.021 g

12%

1 : 1.3

Blank
(front)

0.016 g

9.5%

1 : 1.4

Based on the intermediate to desired products ratio and percentage of styrene carbonate:
The top position is optimal for a more complete reaction.
The front and bottom are fairly similar, with the bottom being the worst position.
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