VSU Chemistry Lab Synthesizes Adipic Acid

DEPARTMENT OF PURE &
APPLIED CHEMISTRY
Visca, Baybay City, Leyte, PHILIPPINES
Telefax: + 63 563-7747
Email: dpoac@ vsu.edu.ph
Website: www.vsu.edu.ph
DEPARTMENT OF PURE AND APPLIED CHEMISTRY

VSU, Visca, Baybay City, Leyte
Name: Lab Schedule: MW, 10:00 AM – 1:00 PM

Instructor: Rating: ________________
Synthesis of Adipic Acid

Experiment No. 3
ABSTRACT:
This experiment aimed to synthesize adipic acid from the oxidative cleavage of cyclohexene treated
with a strong oxidizing agent of potassium permanganate and to provide and gain familiarity of the possible
reaction mechanism. The experiment was accomplished through the used vacuum filtration, spot test,
neutralization reaction and recrystallization technique to isolate the final product. The calculated percent
yield of adipic acid was 53.8% and its purity was analyzed via melting point determination. Results showed
that the presented experimental procedure was considered an effective way of generating a considerable
maximum pure amount of adipic acid from cyclohexene.
INTRODUCTION:
Dicarboxylic acids are organic compounds that contain two carboxyl functional groups. Adipic acid,
a dicarboxylic acid with IUPAC name Hexanedioic acid is an organic compound with the formula
(CH2)4(COOH)2. From an industrial perspective, it one of the most important dicarboxylic acid, it used for
making nylon (Wade, 2013). The industrial synthesis of adipic acid uses benzene as the starting material,
benzene is hydrogenated to cyclohexane, whose oxidation using a cobalt/acetic acid catalyst gives adipic
acid. However, it is also can be obtain by an oxidation of cyclohexene which thereby the main reaction of
this experiment.
Just as the word reduction usually refers to the addition of hydrogen to a molecule, the word
oxidation usually means the addition of oxygen. The main reaction involved a very strong oxidizer, a basic
solution, and MnO2 waste. According to Klein (2012), potassium permanganate is fairly inexpensive;
however, it is a very strong oxidizing agent, and it often causes further oxidation of the diol. The main
purpose of this experiment was to synthesize adipic acid through the permanganate oxidization of
cyclohexene via oxidative cleavage. Oxidative Cleavage of alkene was defined by Smith (2011) as the
breakage of both the pi “π” and sigma “σ” bonds of the double bond to form two carbonyl groups.
Depending on the number of R groups bonded to the double bond, oxidative cleavage yields either ketones
or aldehydes. The products are initially ketones and aldehydes, but aldehydes are oxidized to carboxylic
acids under these strong oxidizing conditions. The oxidation of an alkene was also an example of an
addition reaction. Oxygen atoms in the oxidizing agent add to the carbon-carbon double bond, and form a
cyclic intermediate. As a result, the ring opens and the dicarboxylic acid was formed.
The other objective for this laboratory exercise was to provide and illustrate a possible reaction
mechanism of the oxidation cleavage of cyclohexene. Consequently, gaining familiarization of the
laboratory method for following the progress of reactions were also noted in regards to some application of
basic laboratory techniques of organic synthesis including vacuum filtration, spot test, neutralization
reaction, recrystallization and melting point determination.
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SCHEMATIC DIAGRAM:
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RESULTS AND OBSERVATIONS:

A. Preparation of Adipic Acid (CH3CH2CH2CH2Br)
Preparation of n-butyl bromide

Reaction Equation
Actual Yield of Adipic Acid 1.57 g

Amount of Cyclohexene 2.0 mL
Theoretical Yield 2.78 g
Percent Yield 53.8%
The table below were the experimental results obtained from the experiment procedure followed by
calculations involved in obtaining the theoretical yield and the percentage yield from the amount of Adipic
acid product attained.
Given: Density of Cyclohexene (C6H10) = 0.81 g/mL

MM of C6H10 = 82.146 g/mol
MM of Adipic Acid (CH2)4(COOH)2 = 146.14 g/mol
3C6H10 + 8KMnO4 + 4H2O → 3C6H10O4 + 8KOH + 8MnO2
Theoretical Yield:
mol of C 6 H 10=2.0 ml C 6 H 10 ( 0.81 g1CmL6 H 10 )( 82.15

1 mol C 6 H 10
gC 6 H 10 )
=0.020 mol C 6 H 10
g of ( CH 2 ) 4 ( COOH ) 2=0.020 mol C 6 H 10 ( 1 mol1( CH 2 ) 4 ( COOH ) 2 146.14 g ( CH 2 ) 4 ( COOH ) 2

mol C 6 H 10 )( 1 mol ( CH 2) 4 ( COOH ) 2 )=2.92 g
Actual Yield:
g of C ( CH 2 ) 4 (COOH ) 2=1.57 g
Percent Yield:
Actual Yield
% yield= x 100 %
Theoretical Yield
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1.57 g
% yield= x 100 %=53.8 %
2.92 g
DISCUSSION:
The synthesis of adipic acid was characterized by oxidative cleavage where in an alkene, breaks
both the π and σ bonds of its double bond to form two carbonyl groups (Smith, 2017). In this particular
reaction, the solution was in warm more vigorous oxidation condition which thereby formed the adipic acid
product. The starting steps in the possible reaction mechanism below was the addition of MnO4 - ion from
the powerful oxidizing agent, KMnO4 to the π bond of cyclohexene creating the two separate Carbon-
Oxygen bonds and thus formed cyclic manganate ester intermediate.
Oxidative cleavage then occurred, breaking the unstable cyclic intermediate and converting its
cyclic structure into an alkyl chain with two terminal aldehyde groups, a di-carbonyl compound (hexanedial).
With a corresponding production of Manganese Oxide (MnO 2) that was the brown precipitate responsible
for the brown coloration in the solution of the experiment.
In the next step of the reaction, the di-carbonyl compound produced was further oxidized by the
another permanganate ion in solution, forming a product that was figuratively close to being a di-carboxylic
acid but without hydrogen. The negatively charged oxygen from the produced compound attracted the free
positively charged potassium ions in the solution from potassium permanganate (KMnO4) forming the
dicarboxylic salt product.
The addition of the concentrated hydrochloric acid to the reaction solution converted the di-
carboxylic salt product into the adipic acid. Hence, after the cooling the solution in a water bath, further
acidification was done by adding another acid. It induces the protonation of the di-carbonyl compound
which thereby breaks the bond it formed with potassium ions. This was also the final step of the reaction
mechanism and it was shown below:
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In the parts of the procedure where cyclohexene was added with potassium permanganate(KMnO4),
possible formation of excess permanganate ions at the solution would occur. The Spot test on filter paper
helped in determining the presence of the excess permanganate ions where in a purple color ring around a
brown color spot (MnO2) indicated its occurrence. These permanganate ions were removed through the
gradual addition of methanol to the solution while also heating it until the purple color ring disappeared.
Since potassium permanganate was a very strong oxidant, it could react to many functional groups, hence,
under controlled conditions, KMnO4 oxidizes very efficiently, converting primary alcohols to carboxylic
acids. According to Wade (2013), the products are initially ketones and aldehydes, but aldehydes are
oxidized to carboxylic acids under these strong oxidizing conditions. As shown in the reaction below,
methanol was partially oxidized into aldehyde first before being fully oxidized to formic acid, the carboxylic
acid product.
The addition of Sodium hydroxide (NaOH) on the other hand, aside from it rinsed the brown color of
Manganese dioxide that utterly covered the flask, it also maximizes the yield of adipic acid. Subsequently,
there was a partial oxidation of MnO 2 by NaOH in the oxidation reaction equation: 2MnO2 + 4NaOH + O2 →
2Na2MnO4 + 2H2O. The other possible used of NaOH was to neutralized the formic acid which was formed
during the oxidation of methanol. The reaction of NaOH and formic acid was an acid-base reaction forming
the salt sodium formate which was soluble in water, shown in the chemical equation: HCOOH(aq) + NaOH(aq)
→ NaCOOH(aq) + H2O(l). The addition of hydrochloric acid also neutralizes the basic solution of the mixture,
hence, the boiling procedure were used to remove the excess water present in the mixture at the same
time the formic acid left behind with a boiling point close to water (BP:100.7 oC). It also removed any
unreacted methanol from the previous step having a boiling point at 64.7oC.
After the boiling procedure, recrystallization was done in obtaining the purest possible final product.
There were approximately 1.57 grams of pure white adipic acid obtained, which also gives 53.8% yield of
the final product, considerably higher upon attaining a highest possible yield. Possible causes of the other
fraction of yield were due to the possible loss of product where in improper swirling would results to some
splashing of the mixture during the magnetic stirring, influences a reduce of yield. Some maybe from the
transferring of the solution from one container to another. Regardless of those some conditions, the purity
of the obtained pure white crystals of adipic acid was tested positive in the melting point determination.
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CONCLUSION:
Therefore, the synthesis of adipic acid was effectively prepared due to the oxidation reaction of
cyclohexene with potassium permanganate under strong oxidizing conditions. The reaction performed an
oxidative cleavage of cyclic manganate ester intermediate formed from the addition of permanganate ions
from the strong oxidizing potassium permanganate agent towards the double bond of cyclohexene. Due to
the more vigorous oxidation condition provided, it yields the final product which was the Adipic Acid. As of
today the mechanism was not yet fully specified based on the subsequent procedure done because some
pathways take several steps that were not yet fully understood. Granting, there were still at least a better
understanding on how the reaction mechanism undergoes. Nonetheless, the percent yield of the reaction
was 53.8% which was considered a fair yield and was efficiently pure.
REFERENCES:
Klein, D. (2012) Organic Chemistry. John Wiley & Sons, Inc. United States of America
McMurry, J. (2017). Organic Chemistry, Ninth Edition. Cengage Learning. 20 Channel Center Street.
Boston, MA 02210, USA.
Smith, J.G. (2011) Organic Chemistry, Third Edition. The McGraw-Hill Companies, Inc., 1221 Avenue of
the Americas, New York, NY 10020.
Wade L. G. (2013) Organic Chemistry. Eight Edition. GEX Publishing Services. Pearson Education,
Inc., Permissions Department, 1900 E. Lake Ave., Glenview, IL 60025.
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Answers to Guide Questions
1. From the reaction equation of the oxidative cleavage, how many equivalents of KMnO4 were taken per
equivalent of cyclohexene?
Based on the chemical equation, `there were eight mol of KMnO4 used to oxidize three equivalents of
cyclohexene to form 3 equivalents of adipic acid.
2. What would the oxidation product have been if cyclohexene had been treated with ozone, followed by
reductive hydrolysis?
3. A pseudo perspective drawing of the cyclohexene structure will show four of the ring carbon atoms in a
tetrahedral bonding arrangement and four of the ring carbons lying in the same plane. Illustrate.
4. Write separate balanced oxidation-reduction reactions showing all products that result when the three
isometric butenes are treated with potassium dichromate and sulfuric acid. `
15 CH2=CHCH2CH3 + 8 K2Cr2O7 + 32 H2SO4 → 20 CH3CH2COOH + 8 Cr2(SO4)3 + 8 K2SO2 + 32 H2O
3 CH3=CHCHCH3 + 4 K2Cr2O7 + 16 H2SO4 →6 CH3COOH + 4 K2SO4 + 4 Cr2(SO4)3 + 16 H2O
4 H2O + 5 H2SO4 + 2 K2Cr2O7 + 9 CH3C(CH3)=CH2 → 9 CH3C(CH3)OHCH2OH + Cr4(SO4)3 + 2 K2SO4
5. If the solubility of adipic acid at 0 OC is 0.80 g per 100 g water, and the total yield of adipic acid obtained
from the oxidation of a sample of cyclohexene amounted only to 0.87 g. What is the maximum volume
of water that should be used to recrystallize the sample and recover 0.80 g of a pure product?
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Answer:
0.87 g−0.80 g=0.07 g
g∗100 g
0.07 =8.75 g water
0.80 g
Therefore, 8.75 g or 8.75 mL of water should be used in order to recover 0.80 g of pure product.
6. Employing a different set of reagents for each reaction, show how the following compounds can be
oxidized into the products shown:
a.) toluene → benzoic acid
Benzoic acid
can be prepared
from the oxidation of toluene heated in the presence of alkaline KMnO4. The process produced the
potassium benzoate ions which then followed acidification to form benzoic acid.
b.) 2-butanone → Propanoic acid
In the first step, the butan-2-one can react with iodine in the presence of sodium hydroxide to
form the sodium propanoate and iodoform. The second step would then convert the sodium
propanoate as it was hydrolyzed in the presence of acid that leads to the formation of propanoic
acid.
c.) glucose → gluconic acid
Glucose on reaction with bromine water gives Gluconic acid. Aldehyde group is oxidized to
carboxylic group.
d.) 2,3-butanediol → acetaldehyde
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DEPARTMENT OF PURE &

DEPARTMENT OF PURE AND APPLIED CHEMISTRY

Name: Lab Schedule: MW, 10:00 AM – 1:00 PM

Synthesis of Adipic Acid

RESULTS AND OBSERVATIONS:

Preparation of n-butyl bromide

Actual Yield of Adipic Acid 1.57 g

Given: Density of Cyclohexene (C6H10) = 0.81 g/mL

mol of C 6 H 10=2.0 ml C 6 H 10 ( 0.81 g1CmL6 H 10 )( 82.15

g of ( CH 2 ) 4 ( COOH ) 2=0.020 mol C 6 H 10 ( 1 mol1( CH 2 ) 4 ( COOH ) 2 146.14 g ( CH 2 ) 4 ( COOH ) 2

Answers to Guide Questions

4 H2O + 5 H2SO4 + 2 K2Cr2O7 + 9 CH3C(CH3)=CH2 → 9 CH3C(CH3)OHCH2OH + Cr4(SO4)3 + 2 K2SO4

b.) 2-butanone → Propanoic acid

d.) 2,3-butanediol → acetaldehyde

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