Synthesis Of Cellulose Acetate

Fuentes, C.K.A.
1
,Gales, B.T.B.
1
,Gepulango, E.P.A.
1
,Hernandez, M.R.
1
, Lantion, E.A.S.
1
1
University of Santo Tomas: Faculty of Pharmacy
Group 4 3F Pharmacy Pharmaceutical Chemistry Laboratory

ABSTRACT

Cellulose acetate is a well-known industrial product that finds many commercial applications. In
the experiment, Cellulose acetate is synthesized through reaction with acetic acid and acetic
anhydride in the presence of a catalyst of sulfuric acid which yielded very little product.

INTRODUCTION
Cellulose [(C6H10)5)n] is a polysaccharide
consisting of a linear chain of several hundred to
over ten thousand (1>4) linked D-glucose
units . It is a substance that makes up the plants
cell wall, many forms of algae, and the
oomycetes. It is a long chain of linked sugar
molecules giving strength to woods.

















Figure 1. Structure of Cellulose

Cellulose has many uses. It can be used as a
fiber supplement, calorie reducer, emulsifier, and
stabilizer. It can also be used to make papers,
cotton linen, film, explosives, and plastics.
Cellulose is tasteless, odorless crystalline that
does not coil or branch; thus, adopting an
extended and stiff rod-like conformation. It is
insoluble in water and most organic solvents,
chiral, and biodegradable. Cellulose can be
broken down chemically into its glucose units
through the treatment of concentrated acids,
such as sulfuric acid, at high temperature.

The synthesis of cellulose involves two
separate processes named chain initiation and
elongation. Cellulose synthetase (CesA) proteins
catalyze the chain elongation step in glucan
plolymerization. It initiates the polymerization
through a steroid primer, sitosterol-beta-
glucoside, and UDP-glucose. Cellulose synthesis
utilizes UDP-D-glucose precursors to elongate the
growing cellulose chain.

Acetic acid is classified as a weak acid, because it
does not completely dissociate into its component
ions when dissolved in aqueous solution. At a
concentration of 0.1 M, only about 1% of the
molecules are ionized. In solution, there is a
dynamic equilibrium between the neutral
molecules and the acetate and hydronium ions.
Acetic acid is an important industrial chemical.










Figure 2. Structure of Acetic Acid

The primary use of this chemical is in the
manufacture of assorted acetate esters. These
are substances formed by reacting acetic acid
with a substance containing a hydroxyl (OH)
group. Cellulose, found in cotton and wood, is a
polymeric material containing multiple hydroxyl
groups. It reacts with acetic acid to yield
cellulose acetate, which is used to make films
and textiles.

Moreover, Acetic anhydride is a clear, colorless,
mobile (free-flowing) liquid with a sharp odor
similar to that of acetic acid. It hydrolyzes in
water to yield acetic acid. In its liquid or vapor
state, acetic anhydride can irritate body tissues,
possibly leading to the death of such tissue.
Acetic anhydride melts at 73EC, boils at 139EC,
and has a density of1.080 g/mL at 15EC. It is
flammable with a flash point of 54EC. This
compound is readily combustible and represents
a fire hazard.











Figure 3. Structure of Acetic Anhydride

The primary use of acetic anhydride is used in
the manufacture of cellulose acetate for films and
plastic goods; about 75 percent of the acetic
anhydride produced annually in the United States
is used for this purpose.

EXPERIMENTAL
A. Materials
20 mL graduated cylinder, 250 mL erlenmeyer
flask, filter paper, stirring rod, 1 L beaker, oven,
watch glass, parafilm

Compounds tested(or samples used)
Acetic acid, acetic anhydride, sulfuric acid,

B. Procedure
1. Synthesis of cellulose acetate
In a 125 mL erlenmeyer flask, 8mL of acetic
anhydride, 20 mL of acetic acid and 2 drops of
sulfuric acid were placed. The solution was then
mixed for 10 minutes to ensure that it was
completely mixed. After mixing the solution, 0.5
of cut filter paper was added and it was mixed
with a stirring rod until the structure of the filter
paper completely broke. The flask was cover with
parafilm and was kept. After a week, 500 mL of
water was placed into a 1 L beaker. The solution
that was prepared a week ago was poured into
the beaker. It was stirred vigorously until a
precipitate was formed. The solution was then
filtered, removing as much water as possible. The
residue that was gotten from filtration was place
in an evaporating dish and placed in the oven at
110 C for 10 minutes. After drying it in the oven,
the evaporating dish was weighed and
percentage yield was calculated. Half of the
product was dissolved in an enough amount of
acetone to make a thin paste. It was placed
above a watch glass and allowed it to dry until a
cellulose acetate film was formed.

RESULTS AND DISCUSSION



Figure 4 Structure of Cellulose Acetate

The maximum yield obtain is about 12.83








REFERENCE
Chemistry 10th Edition by Chang (2010)
Pastro, D. J., John, C. R., & Miller, M. S. (1998).
Experiment and Techniquesin Organic Chemistry.
New Jersey: Prentice Hall. Pg. 43-46
Pavia, D. L., Lampman, G. M., Kriz, G. S., &
Engel, R. G. (1999). OrganicLaboratory
Techniques: A MicroscaleApproarch (3rd Ed.).
Harcourt CollegePubliser. Pg. 558-576
Acetic Acid & Acetic Anhydride Retrived from
http://scifun.chem.wisc.edu/chemweek/pdf/aceti
cacid.pdf

Acetic anhydride (acetyl ether). (n.d.). Retrieved
fromhttp://chemicalland21.com/petrochemical/A
CETIC%20ANHYDRIDE.htm
CelluloseRetrievedfrom
http://www.academia.edu/1745723/Cellulose

General Chemistry.Cellulose Retrievedfrom
http://antoine.frostburg.edu/chem/senese/101/c
onsumer/faq/what-is-cellulose.shtml

VirtualChembook.ElhmhurstCollege.
Retrievedfromhttp://www.elmhurst.edu/~chm/vc
hembook/547cellulose.html