CHAPTER 2

LITERATURE REVIEW

2.1 Preface

This chapter begins with the introduction of glucose and its application
towards living organisms. Then it will proceed with the hot spring mud and the
catalyst used in this study, together with the procedure of treatment and preparation
options. Then the chapter covers the acid catalyzed reaction itself, parameters that
influence the reaction which are type of catalysts and substrate concentration
including the possible product from the reaction and the type of reactor used for the
reaction takes place. This chapter ended with a summary of the literature review.
2.2 Glucose

Glucose is a simple sugar with the molecular formula of C 6H12O6. It circulates

in the blood of animals and human as blood sugar. With 6 carbon atoms, it is classed
as a hexose which is a subcategory of the monosaccharides. Glucose can be
obtained by hydrolysis of carbohydrates such as milk sugar, cane sugar, maltose,
cellulose and glycogen (Britannica, 2017). It is commonly commercially manufactured
form cornstarch by hydrolysis via pressurized streaming at controlled pH in a jet
followed by further enzymatic depolymerization.

Figure 2.1: Structure of glucose.

A pharmacist from Germany named Andreas Marggraf was found glucose in

raisins in the year 1747 (E-natural.org, 2017). However, he called it as ‘eine Art
Zucke’.It was only in 1838 when the term ‘glucose’ was introduced and this was done
by Jean Baptiste Andre Dumas. The word was derived from a Greek word glycos
which means sweet.

Glucose has benefits as well as potential risks. Without glucose, a person will
feel weak because of lack of energy. It is also aids in cellular respiration (E-
natural.org, 2017). It can be said that humans need glucose but it is equally
significant that you regulate its levels in the body. A blood glucose test can measure
the blood glucose and determine if a person has diabetes. Nowadays, it is difficult to
find foods without glucose. Some sugar monitoring need to be done to make sure our
body remains healthy.

There are 4 types of sugars stated in goodhousekeeping.com (Nestle, 2010).

Firstly, glucose is the sugar in blood. Next, fructose is the principal sugar in fruit.
Sucrose is table sugar. It is double sugar which contains one part each of glucose
and fructose. Lastly, high fructose corn syrup (HFCS) is made from corn starch. It
contains 45 – 58 % of glucose and 42 – 55 % fructose.
2.3 Hot Spring Mud (HSM)

Hot spring, or also known as thermal spring is a spring with water which at
higher temperature than the air temperature of the surrounding region. Most of the
hot spring released groundwater that is heated by shallow intrusions of magma in
volcanic areas (Encyclopaedia Britannica, 2017). In a few cases, the water is heated
by convective circulation where the groundwater percolating downward reaches
depths of kilometer where the temperature of rocks is higher due to the normal
temperature gradient of the Earth’s crust.

Many of the colors in hot springs are caused by thermophilic microorganisms,

which include certain types of bacteria. The mud normally consists of high amount of
natural silica which can be used as support materials other than alumina, zeolite and
carbon. The silica has the tendency to form large networks and has hardness in its
structure (Ali, Rahman, Sarkar, & Hamid, 2014).

Ali stated in his studies that silica has a few advantages compared to
disadvantages. Silica has high in efficiency, selectivity and stability. It is also having a
mechanical strength. On the other hand, silica has low compatibility and some
formation of aggregates or agglomerates may occur.

2.3.1 Physical and Chemical Treatment

The collected hot spring mud must be treated physically and chemically
before further processing. Physical treatment is the process where any unwanted
materials and substances are removed by hand from the mud. Kitchen sieve may be
used in this step to easy the process. Next, chemical treatment of the mud is the
process to neutralize the mud before use it in other process. Neutralize here means
removing any acidic or alkaline compound exists in the mud. This step is using
hydrochloric acid and sodium hydroxide as their neutralizing agent. Besides, any
heavy metals also been removed by this step.
2.4 Catalyst

Catalyst is defined as something that makes a chemical reaction happen

more quickly by lowering the Activation energy (EA) without itself being changed
(Cambridge Dictionary, 2017). Approximately, around 85 – 90 % of the products of
chemical industry are made from catalytic reaction. One example is the production of
cumene from benzene and propylene, zeolite catalyst is used to enhance the
reaction and giving higher yield of cumene as the final products (Grieves, Klaassen,
Connor, & Keffer, 2015).

In order to produce a new product, reactants must overcome certain energy

called activation energy (Byju, 2017). This energy is the difference between the
energy of transition state and the reactant species. Some reactant molecules have
enough kinetic energy to overcome this energy barrier whereas others don’t. Hence,
not all reactions happen at the same rate as in general conditions. Thus, certain
reagents are added which can lower the required activation energy for the conversion
of the reactants to products.

Figure 2.2: Activation energy in a reaction with and without catalyst.

There are multiple forms of catalysts, varying from atoms and molecules to
large structures. In addition, catalyst can be employed in various surroundings which
are in liquids, gases or on the surface of the solid. It can be homogeneous and
heterogeneous (I. Chorkendorff, 2005). Homogenous catalyst is the both catalyst and
the reactants are in the same phase while heterogeneous catalyst is the catalyst and
reactants are in the different phase. In general, heterogeneous catalyst is better
because the catalyst is easier to be separated after the reaction due to obviously
different in phase.

2.4.1 Type of Catalyst

Catalyst for a chemical reaction can be divided into two categories which are
heterogeneous catalyst and homogeneous catalyst. Both types have their own
advantages and disadvantages of usage which will discuss in this subchapter.

Based on chemistry definition by Dictionary.com (2015), heterogeneous is

defined as a composed of different substances or the same substance in different
phase. For example, reaction of hydrogen and nitrogen in the presence of finely
divided iron to form ammonia. As for homogeneous, it is a mixture of same
substance in the same phase. The hydrolysis process of sugar in the presence of
sulfuric acid is the best example of homogeneous reaction.

Heterogeneous catalyst is more stable and can be reusable for a few times
onwards. Besides, the preparation of heterogeneous catalyst is simple compared to
homogeneous catalyst. On the other hand, homogeneous catalyst is less in stability
has difficulties in separation and can cause corrosion to the reactor (Ali et al., 2014).
Plus, the handling for homogeneous catalyst is more complicated.

Figure 2.3: Heterogeneous catalyst and homogeneous catalyst.

2.4.2 External Diffusion

The diffusion is the spontaneous intermingling or mixing of molecules by

random thermal action (Donovan, 2008). It is very important for every catalytic
reaction because the substrate will be attached to the active site of the catalyst for
the reaction to form products. Molecules of a given species within a single phase will
always diffuse from higher concentration region to lower.

The supervening of diffusion in heterogeneous catalytic reaction is follows the

Michaelis-Menten kinetics law which is quantitatively characterized by dimensionless
parameters that are independent of the substrate concentration (Horvath &
Engasser, 1974). The movement of substrate in a catalytic reaction into the active
site of the catalyst has found to affect the overall kinetic behavior of that catalyst.

The effect of external diffusion is when the catalytic reaction only takes place
at the surface. The movement of substrate occurs by the molecular diffusion. The
rate of substrate movement or transport to the surface at steady state is equal to the
rate of substrate consumed in the reaction.
2.4.3 Surface Adsorption Theory

Old theory said that in heterogeneous catalyst reaction, the reactants in their
gaseous state or in their dissolved state in any solution will get adsorbed on the
surface of the catalyst. The increase in concentration of the reactants on the surface
of the catalyst, the availability and probability of the occurrence of a reaction between
two species increases (Byju, 2017). Thus, the rate of reaction for this chemical
reaction will increase. As in the intermediate adsorption theory, the reaction that is
desired can be achieved by the formation of an intermediate compound and the
following decomposition of the same compound into the desired products. In this
process, the catalyst is regenerated after the reaction is over.

With the combination of old theory and intermediate theory, there is modern
adsorption theory formed to explain the process in this modern era. It said that the
process of heterogeneous catalyst takes place in a several stages (Chemistry
LibreTexts, 2016). Firstly, reactants are diffused to the surface of catalyst. The
thickness of the boundary layer and bulk concentration will influence the rate of
diffusion of reactants to the surface. Next, reactants are adsorbed to the catalyst.
Bonds are formed as the reactants are adsorbed onto the surface of the catalyst.
Then, the reaction occurred where bonds form between the atoms and molecules on
the surface. After the reaction is done, the products are desorbed from the catalyst.
Bonds are broken as the products desorbs from the surface. Lastly, the products are
diffused away from the catalyst.
2.4.4 Preparation of Catalyst

The catalyst preparation methods can broadly categorized into three methods
which are bulk preparation process, impregnation process and physical mixing
process (IIT Guwahati, 2014). These processes have been widely used to prepare
the catalyst for industrial usage.

Firstly, bulk preparation process. Bulk catalysts and supports are prepared by
this method. Bulk preparation is mainly done by these two methods; precipitation and
co-precipitation process; and Solgel process. Bulk catalysts are catalyst that consist
catalytically active substance. Examples include silica-alumina catalysts for catalytic
cracking and potassium oxide for the synthesis of ammonia.

Next is impregnation process. This process used the supports that firstly
prepared by bulk preparation methods and then impregnated with the catalytically
active material. The active materials can be deposited on the supports by various
methods. Most of the methods involve aqueous solutions and liquid solid interface. In
some cases, deposition is done from the gas phase and involves gas-solid interface.
In supported catalysts, the catalytically active materials are dispersed over the high
surface area support material. For example, hydrodesulphurization is carried over
molybdenum oxide supported on alumina.

Last method is by physical mixing. Mixed agglomerated catalysts are usually

prepared by using this method. These catalysts are prepared by physically mixing the
active substances with a powdered support or precursors of support in ball mill. The
final mixture is then agglomerated and activated. This type of catalysts is used less
frequently.
2.5 Acid Catalyzed Reaction

This part will discuss more about the reaction details in term of technical and
mechanical part. Basically, the mixture is completely reacted with the help of several
controls that maintain the reaction condition. Plus, there are a few parameters that
are very important in this reaction such as reaction time and substrate concentration.
A mini batch reactor was used to perform the reaction effectively. This reaction is
assumed to be toxic free since the materials and chemicals used in this project are
less toxicity.

2.5.1 Brønsted–Lowry Acid–Base Theory

Acids and bases play significant roles in many organic chemical reactions.
So, this theory explains about the acid and base interactions in terms of proton
transfer between the chemical compounds. A Bronsted-Lowry acid is any chemical
that can donate a proton, H+ while a Bronsted-Lowry base is any chemical that can
accept proton (Khan Academy, 2017). An acid that dissociates completely into its
constituent ions in an aqueous solution is called as a strong acid. The strength of
acid somehow can affect the reaction rate of a chemical reaction.

In chemistry, both hydrochloric acid (HCl) and sulfuric acid (H2SO4) are strong
acid, but HCl is stronger because it dissociates completely in its constituent ions
when dissolved in an aqueous solution. However, a study found that H 2SO4 catalyst
gave an optimum condition to the hydrolysis of Kappaphycus alvarezii (cottonii) into
sugars (Meinita, Hong, & Jeong, 2012). This study compares the effectiveness
between HCl catalyst and H2SO4 catalyst.
2.5.2 Reaction Condition

There are so many suggestions from previous studies about the reaction
condition of acid catalyzed reaction for glucose conversion. Reaction time and
temperature are two important operation variables to affect the yield of some
products. Lourvanij and Rorrer (1993) stated that 100 % of glucose converted at 160
o
C after 8 hour of reaction time. But, this study was using solid acid Y-zeolite catalyst
which it has a difficulty to exploit the shape selectivity (Ali et al., 2014).

Besides, according to Junping Zhuang and Xueping Li (2012), the most

optimize condition for the production of levulinic acid from glucose was at 180 oC for
2 hour reaction. They used SO42-/TiO2-Al2O3-SnO2 solid acid as the catalyst and the
optimize loading was 3 gram with 2 wt% glucose. The yield of levulinic acid from this
reaction was 74.05 %. Meanwhile, in 2016, Bayu et al. found that levulinic acid can
be produced efficiently from glucose at 155 oC in 90 minutes of reaction.

These studies can conclude that the glucose conversion mostly complete at
the range of temperature from 150 oC to 180 oC with its own reaction time. The
catalysts used in the reaction and materials loading affect the reaction time. As
stated in Bronsted-Lowry theory, different strength of acid gives different reaction
rate. In this study, it begins with the determination of optimum reaction time of acid
catalyzed reaction at 160 oC as referred to Lourvanij and Rorrer.

In every chemical reaction that using catalyst to enhance the reaction, there
are a few parameters that must be take care of. To achieve higher yield of
productivity in an optimum condition, all of the parameters involved must be at an
accurate point. The parameters are temperature, pressure, agitation speed, substrate
concentration and type of catalyst and its loading into the reactor. Two of these
variables are explained in next subchapters.
2.5.3 Influence of Type of Catalysts on Activity

The different type of catalyst used in the reaction may give different products
even though the reaction condition is similar. It depends on the acid or base content
on the catalyst surface because it will react with the substrate to form a product. As in
paper by Meinita, Hong and Jeong (2012), they studied the differences of sulfuric
acid and hydrochloric acid as catalysts in hydrolysis of Kappaphycus alvarezii. They
found that sulfuric acid catalyst is more efficient in the reaction which yields higher
concentration of galactose and glucose compared to the reaction using hydrochloric
acid catalyst.

There was a study that synthesize the conversion of glucose into

hydroxymethyl furfural (HMF) by using different catalysts and solvents (Zhou et al.,
2017). The focus is in the differences of usage of catalyst in the reaction. The result
showed that maximum HMF produced differently with different catalyst in water as its
solvent at 130 oC. CrCl3.6H2O catalyst contributed higher HMF production (13.04 %)
followed by AlCl3 and FeCl3.6H2O with 11.15 % and 1.72 % of HMF respectively. This
explained that even the solvent and temperature of a reaction are same; the different
of catalysts still give deference in the productivity.

Besides, in the decomposition of hydrogen peroxide also explained the effect

of using different type of catalyst (Science, 2015). A fair test is done using same
amount of each catalyst; Manganese (IV) Oxide, Copper (II) Oxide and Zinc Oxide.
The result showed that Manganese (IV) Oxide is the best catalyst to decompose
hydrogen peroxide into oxygen and water. The Figure 2.4 below illustrates the
differences of using different catalyst in the process.
Figure 2.4: Different type of catalyst used in the reaction give different amount of
oxygen throughout the reaction. (Science, 2015)
2.5.3 Influence of Substrate Concentration on Catalytic Activity

Changing the substrate concentrations can affect the rate of reaction of a

catalyzed reaction. The rate of reaction in a catalytic reaction will be affected if the
concentration of substrate is the limiting factor of the reaction (Adam, 2016). This is a
factor that is stopping a reaction from proceeding at a higher rate. The rate of
reaction will increase as the substrate concentration increases. This is because more
substrate molecules will be colliding with enzyme molecules, so more product will be
formed. However, after a certain concentration, any increase will have no effect on
the rate of reaction, since substrate concentration will no longer be the limiting factor.

Figure 2.5: Effect of substrate concentration to the rate of reaction.

At lower concentration of substrate, the active sites on most of the catalyst

surface are not filled because there is not much substrate. When it comes to high
substrate concentration, more collisions between the molecules occurred (Michael J.
Gregory, 2016). With more molecules and more collisions, catalysts are more likely
to encounter the reactant. The maximum velocity of a reaction is reached when the
active sites are almost continuously filled. Increased substrate concentration after
this point will not increase the rate. Reaction rate therefore increases as substrate
concentration is increased but it levels off.
2.5.4 Possible Products

There are a lot products can be produced form the reaction of glucose with
different reactants and catalysts under different reaction condition. There was a study
by Xun Hu and his team which stated the reaction pathways of glucose during its
esterification process (Hu, Lievens, Larcher, & Li, 2011). In two different medium or
solvent, several products can be produced.

Methanolysis is the reaction of glucose in methanol which produces methyl a-

D-glucopyranoside (MGP) as the main product and methyl a-D-mannofuranoside
(MFS) as minor product. As the temperature increases from 90 oC to 150 oC, MGP
started to degrade to other products which are the furan derivatives (MFA, HDF,
DMF, and DOF). Methyl levulinate and methyl formate were also produced
simultaneously with the formation of DMF and other furan furan derivatives. Then,
further degradation of most of the furan derivatives produced earlier will produce
more methyl levulinate. Methyl levulinate and methyl formate are the main products
from this process which also produced a few minor products (MADA, Methyl
pyruvate, Methyl 2-furoate and MHFN) and small amount of humin-type polymer.

Meanwhile, in water-rich medium process which is using water as the solvent

will also undergo similar reaction condition, but the product produced are different.
Glucose will degrade into 5-(hydroxymethyl)furfural (HMF) and furfural. Further
process of the degradation of glucose in water will produce formic acid and levulinic
acid as the main products. A few minor products (Acetic acid, DDPN, DDMP and
HMCO) and also large amount of humin-type polymer were produced from the
hydrolysis of glucose. This study concluded that glucose can be efficiently converted
to methyl levulinate with high yield in methanol-rich medium due to suppression of
humin-type polymer formation. The reaction pathways of both solvent used in this
study is shown in Figure 2.6.

There are a lot more studies from experts stated the different products
produced from the reaction of glucose. Chidambaram and Bell (2010) also did the
reactions of glucose using dehydration process and HMF was produced from the
reaction. Further conversion of HMF in their studies can produce DMF, which can be
used as fuel or fuel additive. Besides, levulinic acid and formic acid can also be
formed from glucose through HMF by using solid acid catalyst (Junping Zhuang,
Xueping Li, 2012).

Figure 2.6: Reaction pathways of glucose. (Hu et al., 2011)

Figure 2.7: Reaction pathways of glucose to levulinic acid. (Junping Zhuang,
Xueping Li, 2012)
2.5.5 Reactor

Batch reactor is the most suitable reactor for the small scale of glucose
reactions in laboratory (Michigan, 2014). It is a closed reactor that is not receiving
further input during the reaction occurred inside. The reactor is completed with
stirring equipment and heat supply to heat up the mixture inside. The stirring
equipment can either be motor or stir bar. Small scale batch reactor, for example the
one that been used in this project, can use stir bar to stir up the mixture inside the
reactor. For the supply, normally an oil bath is used since oil can be heated up more
than 100 oC.

In the batch experiments for hydrothermal gasification of glucose and starch,

the characteristics of the produced gases were almost identical after a certain
reaction time (Kumabe, Itoh, Matsumoto, & Hasegawa, 2017). They also stated that if
the reaction undergoes in continuous reactor, the efficiency of the reaction is lower in
terms of conversion efficiency and composition of the gas produced. Figure 2.8
below illustrated the typical diagram of batch reactor.

Figure 2.8: Batch reactor.

2.6 Summary

Based on the literature studies, it can be concluded that the synthesis of solid
acid catalyst can be done in a few ways under a certain condition. By using physical
mixing method of catalyst support and acid show promising outcomes in producing
levulinic acid from glucose. All the parameters are crucial in improving the catalytic
reaction of glucose into levuinic acid. Optimal condition for the reaction have been
found to be in the water-rich medium, using acid catalyst and high stirring speed in a
batch reactor.
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