PAMANTASAN NG LUNGSOD NG MAYNILA

(University of the City of Manila)

College of Engineering and Technology
Chemical Engineering Department

Condensation of Hydrolyzed
Cotton Stalks for the
Production of Diphenolic Acid

Submitted by:
Barros, Diego Silvano J.
De Guzman, Khaye Anne
Enriquez, Maria Angelyn C.
Reyes, Jonathan P.

____________________________
Engr. Milagros R. Cabangon

____________________________
Engr. April Anne Tigue

PAMANTASAN NG LUNGSOD NG MAYNILA

(University of the City of Manila)
College of Engineering and Technology
Chemical Engineering Department

RAW MATERIAL
COTTON STALK

Cotton stalk is one of the crop residues left after

the cotton harvest. This residue is abandoned as
waste, but are often incinerated or ploughed into
the soil as they may host insects that can infest
the next cotton crop (Wuren Huang et al., 2012).
Also, the problems associated with the burning
of these solid fuels are the emissions of dark
smoke and the carry-over of partially carbonized
fibrous particulates due to incomplete combustion of the fuels can be tackled by
commercially-proven technologies in the form of high-pressure boilers.
Cotton stalk contains high amount of cellulose compared to other biomass as
shown in the table.

PAMANTASAN NG LUNGSOD NG MAYNILA

(University of the City of Manila)
College of Engineering and Technology
Chemical Engineering Department
PROCESS

The production of Diphenolic Acid is divided into three main stages;

1. Pretreatment of Palm Kernel Shells;
2. Conversion of Palm Kernel Shells to Levulinic Acid;
3. Conversion of Levulinic Acid to Diphenolic Acid.
Figure 2: Process Diagram of the Production of Diphenolic Acid Using
Cotton Stalk

PAMANTASAN NG LUNGSOD NG MAYNILA

(University of the City of Manila)
College of Engineering and Technology
Chemical Engineering Department

1. Pretreatment of Cotton Stalks

The pretreatment of cotton stalks involves drying, size reduction
and screening. Drying is important to reduce the moisture content of the
cotton stalk because excessive water would hinder the hydrolysis. The cotton
stalks are grinded to reduce its particle size and are sieved to uniform the
particle size.
2. Conversion of Cotton Stalk to Levulinic Acid
2.1 Alkali Digestion
Alkali pretreatment increases the accessibility of hydrolysis to the
cellulose as it removes lignin and a part of the hemicellulose. Alkali pretreatment
appears to be the most effective method in breaking the ester bonds between
lignin, hemicellulose and cellulose, and avoiding fragmentation of the hemicellulose
polymers (Harmsen et. al, 2010).

2.2

Acid Hydrolysis

A biomass hydrolysate may be obtained by acid hydrolysis of biomass.

Suitable acids in the acid hydrolysis of biomass or C6 sugars include
sulphuric acid, hydrochloric acid, and phosphoric acid. A preferred acid is
sulphuric

acid,

preferably

diluted

sulphuric

acid,

for

example

at

concentration between 1.5-3%. The temperature in the acid hydrolysis may

depend on the source of carbohydrates, and typically ranges between 120-

PAMANTASAN NG LUNGSOD NG MAYNILA

(University of the City of Manila)
College of Engineering and Technology
Chemical Engineering Department

250 C., preferably between 120-200 C. Said process may comprise one,
two, or more stages. The pressure may also depend on the source of the
biomass carbohydrates, as well as on the temperature, and may be
anywhere between 1 and 50 bar, preferably between 5 and 40 bar, even
more preferably between 10 and 30 bar

Figure 3: Conversion of Lignocellulose Biomass to Levulinic Acid

3. Conversion of Levulinic Acid to Diphenolic Acid

Diphenolic Acid is prepared by condensation reaction of phenol
with levulinic acid in the presence of hydrochloric acid. The reaction
involved is:
2C6H5OH + CH3C(O)CH2CH2COOH CH3C(p-C6H4OH)2CH2CH2COOH + H2O

PAMANTASAN NG LUNGSOD NG MAYNILA

(University of the City of Manila)
College of Engineering and Technology
Chemical Engineering Department

PRODUCT

Diphenolic Acid (C17H18O4)

is one of the

derivatives of levulinic acid and has a

carboxylic acid group. Its appearance varies
from white to brown crystals. It is slightly
soluble in water and soluble in organic
solvents

such

as

acetic

acid, ketones,

ethanol, and isopropanol. Diphenolic acid

gets the interest of the market because it
can take the place of Bisphenol A which is the raw material for the
production of epoxy resin.

It is used in preparing alkyd resin, phenol

formaldehyde resins, printing-inks, adhesives and coatings.

References

PAMANTASAN NG LUNGSOD NG MAYNILA

(University of the City of Manila)
College of Engineering and Technology
Chemical Engineering Department

Retrieved from http://www.patentsencyclopedia.com/app/20150299087

c3cy01058a
http://www.google.com/patents/WO2014037560A1?cl=en
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crd95M&hl=en&sa=X&ved=0ahUKEwjF7aKpyZrNAhVKC8AKHVavD7QQ
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