HKDSE CHEMISTRY — A Modern View (Second Edition)

Part XIII Industrial chemistry

Chemistry: Chapter 55 Green chemistry for industrial processes

Structured questions

Section 55.1
|!|CMELF0135500001|!|
Glyceryl tristearate can be used to produce sodium stearate, which is an ingredient in
a type of soap:

+ 3NaOH X + 3CH3(CH2)16COONa+
heat

(a) Name the above reaction. (1 mark)

(b) Suggest what X is. (1 mark)

(c) Calculate the atom economy of the reaction.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0, Na = 23.0) (2 marks)

(d) Suggest ONE reason why the above reaction is NOT considered as a green
reaction. (1 mark)

##
(a) Saponification / alkaline hydrolysis 1
(b) Glycerol 1

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(c) Mass of atoms in 1 mole of glyceryl tristearate (C57H110O6)

= (12.0 × 57 + 1.0 × 110 + 16.0 × 6) g = 890 g
Mass of atoms in 3 moles of NaOH = (23.0 + 16.0 + 1.0) × 3 g = 120 g
Mass of atoms in 3 moles of sodium stearate (CH3(CH2)16COONa+)
= (12.0 × 18 + 1.0 × 35 + 16.0 × 2 + 23.0) × 3 g = 918 g 1

Atom economy of the reaction = × 100% = 90.9% 1

(d) The reaction involves the use of corrosive sodium hydroxide solution.
(Accept other reasonable answers.) 1
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##

|!|CMELF0135500002|!|
Benzenesulphonic acid (C6H5SO3H) can be synthesized by two pathways as follows:
Pathway 1: benzene + sulphur trioxide  benzenesulphonic acid
Pathway 2: benzene + sulphuric acid  benzenesulphonic acid + water

(a) Write the chemical equations for the above reactions. (2 marks)

(b) State and explain which of the pathways is greener in terms of atom economy.
(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0, S = 32.1) (5 marks)

##
(a) Pathway 1: C6H6 + SO3  C6H5SO3H 1
Pathway 2: C6H6 + H2SO4  C6H5SO3H + H2O 1

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(b) Mass of atoms in 1 mole of C6H6 = (12.0 × 6 + 1.0 × 6) g = 78.0 g

Mass of atoms in 1 mole of SO3 = (32.1 + 16.0 × 3) g = 80.1 g
Mass of atoms in 1 mole of H2SO4 = (1.0 × 2 + 32.1 + 16.0 × 4) g
= 98.1 g
Mass of atoms in 1 mole of C6H5SO3H
= (12.0 × 6 + 1.0 × 6 + 32.1 + 16.0 × 3) g = 158.1 g

For pathway 1, atom economy = × 100% 1

= 100% 1

For pathway 2, atom economy = × 100% 1

= 89.8% 1
As pathway 1 has a higher atom economy, it is greener. 1
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##

|!|CMELF0135500003|!|
Ethanol can be produced by two pathways as follows:
Pathway I: CH2=CH2 + H2O  C2H5OH
Pathway II: C6H12O6  2C2H5OH + 2CO2

(a) (i) Name the reaction of pathway II. (1 mark)

(ii) Suggest a catalyst used in pathway II. (1 mark)

(b) In terms of atom economy, state and explain which pathway is greener.
(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (5 marks)

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##
(a) (i) Fermentation 1
(ii) Enzymes in yeast 1
(b) Mass of atoms in 1 mole of CH2=CH2 = (12.0 × 2 + 1.0 × 4) g = 28.0 g
Mass of atoms in 1 mole of H2O = (1.0 × 2 + 16.0) g = 18.0 g
Mass of atoms in 1 mole of C6H12O6
= (12.0 × 6 + 1.0 × 12 + 16.0 × 6) g = 180 g
Mass of atoms in 1 mole of C2H5OH
= (12.0 × 2 + 1.0 × 6 + 16.0) g = 46.0 g

For pathway I, atom economy = × 100% 1

= 100% 1

For pathway II, atom economy = × 100% 1

= 51.1% 1
As pathway I has a higher atom economy, it is greener. 1
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##

|!|CMELF0135500004|!|
Volatile organic compounds (VOCs) are organic compounds with low melting points.
They are common solvents used in industry.

(a) Give TWO examples of VOCs. (2 mark)

(b) State ONE pollution problem caused by VOCs. (1 mark)

(c) Suggest ONE reason why the use of VOCs does NOT comply with the principles
of green chemistry. (1 mark)

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(d) Suggest a green solvent to replace VOCs. (1 mark)

##
(a) Any TWO:
Benzene / chloroform / tetrachloromethane (accept other reasonable
answers) 2
(b) It causes photochemical smog. 1
(c) Many VOCs are harmful / flammable / toxic. 1
(d) (Supercritical) carbon dioxide / ionic liquids 1
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##

|!|CMELF0135500005|!|
‘Designing degradable chemical products’ is one of the green chemistry principles.

(a) Using the above principle, explain why the following chemical products are
NOT green.
(i) Polyethene plastic bags (1 mark)

(ii) Polystyrene foam with CFCs as blowing agents (2 marks)

(iii) DDT (1 mark)

(b) As using polyethene plastic bags is not a green practice, there are alternatives to
replace the use of polyethene plastic bags. Suggest TWO such alternatives.
(2 marks)

##
(a) (i) They are non-biodegradable and stay in landfills for a very long time. 1
(ii) Polystyrene foam is non-biodegradable and stays in landfills for a

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very long time.

Besides, CFCs can deplete the ozone layer. 1
(iii) As DDT is not degradable, it accumulates in plants and animals,
causing damage to humans. 1
(b) Any TWO:
Photodegradable plastic bags / biodegradable plastic bags / paper bags 2
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##

Section 55.2
|!|CMELF0135500006|!|
In Wacker process, ethene is oxidized by oxygen to ethanal in the presence of
palladium(II) chloride and copper(II) chloride catalyst. The ethanal is then further
oxidized to ethanoic acid.

(a) State ONE green chemistry practice adopted by the process. (1 mark)

(b) Suggest TWO reasons why the process is NOT a green one. (2 marks)

(c) State TWO applications of ethanoic acid. (2 marks)

(d) State another industrial process that can be used to produce ethanoic acid.
(1 mark)

##
(a) Using catalysts 1
(b) It produces harmful chlorinated by-products, which require separation
and disposal. 1
The atom economy of the overall reaction is low. 1
(c) Any TWO:

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It is used to produce PET for making water bottles / polyvinyl acetate for
making glues and synthetic fibers / table vinegar / pickled vegetables. 2
(d) Oxidation of naphtha or butane / Monsanto process / CATIVA process 1
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|!|CMELF0135500007|!|
The Monsanto process is an important method for the manufacture of acetic acid by
catalytic carbonylation of methanol.

(a) State the catalysts used in the process. (1 mark)

(b) State TWO green chemistry practices adopted by the process. Explain briefly.
(2 marks)

(c) There are some side reactions in the process. Write an equation for ONE side
reaction. (1 mark)

(d) Suggest TWO limitations of the process. (2 marks)

##
(a) Rhodium and hydrogen iodide 1
(b) The use of catalyst can speed up the chemical reaction and get more
products in a relatively shorter period of time. 1
The atom economy of carbonylation of methanol is 100%. 1
(c) CO + H2O  CO2 + H2 1
(d) Any TWO:
A very large volume of water is used in the reaction vessel / the catalyst
used (rhodium) is expensive / the process requires separation step for

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Part XIII Industrial chemistry

removing the by-products produced. (Accept other reasonable answers) 2

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|!|CMELF0135500008|!|
It is known that CATIVA process is greener than Monsanto process.

(a) State the catalyst used in the CATIVA process. (1 mark)

(b) Explain why the catalyst used in the CATIVA process is better than that in the
Monsanto process. (1 mark)

(c) State THREE advantages of the CATIVA process over the Monsanto process.
(3 marks)

##
(a) Iridium 1
(b) Iridium is about five times cheaper than rhodium (the catalyst used in the
Monsanto process). 1
(c) The reaction rate is significantly higher. 1
Less water is required. 1
There are fewer by-products produced. 1
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##

|!|CMELF0135500009|!|
Ethanoic acid can be synthesized by Monsanto process or CATIVA process.

(a) Write an equation for the synthesis of ethanoic acid in Monsanto process and
CATIVA process. (1 mark)

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(b) State the catalysts used in Monsanto process and CATIVA process respectively.
(2 marks)

(c) Write an equation for the side reaction occurring in Monsanto process. (1 mark)

(d) Give TWO advantages of CATIVA process over Monsanto process. (2 marks)

##
(a) CH3OH + CO  CH3COOH 1
(b) Monsanto process: rhodium metal and hydrogen iodide 1
CATIVA process: iridium metal 1
(c) CO + H2O  CO2 + H2 1
(d) Any TWO:
Iridium is much cheaper than rhodium / the reaction is significantly faster
/ less water is used / the side reaction occurring in Monsanto process is
not likely to occur in CATIVA process. 2
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##

|!|CMELF0135500010|!|
Acetic acid is an important chemical. It can be produced by several ways such as
fermentation and carbonylation of methanol.

(a) In terms of the following green chemistry principles, state and explain why
fermentation is NOT a green way.
(i) Waste prevention (1 mark)

(ii) Designing for energy efficiency (1 mark)

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(b) In terms of the following green chemistry principles, state and explain why
carbonylation of methanol is a green way.
(i) Atom economy (1 mark)

(ii) Using renewable raw materials (1 mark)

##
(a) (i) Fermentation produces a considerable amount of biodegradable
waste which may be hazardous to the environment. 1
(ii) Fermentation includes the step for recovering pure ethanoic acid by
distillation. This step is energy-consuming and expensive. 1
(b) (i) Carbonylation of methanol has an atom economy of 100%. 1
(ii) The starting material, methanol, can be produced from renewable
resources such as biomass, wastes and sewages from the community. 1
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|!|CMELF0135500011|!|
Ethanoic acid can be manufactured by the following two processes.
(1) Direct oxidation of naphtha
At 180C and 50 atm, naphtha reacts with oxygen in air to produce ethanoic acid
without the use of catalyst. Carbon monoxide, carbon dioxide and water are the
by-products formed.
(2) Monsanto process
In the presence of Rh and HI as catalysts, methanol reacts with carbon monoxide
at 180C and 30 atm to give ethanoic acid

(a) Write a chemical equation for the Monsanto process. (1 mark)

(b) Calculate the atom economy of the Monsanto process.

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(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

(c) Suggest TWO reasons to explain why process (2) is considered to be greener
than process (1). (2 marks)

(d) Ethanoic acid can be used to produce 1,2-dichloroethane. Outline the synthetic
route, with no more than three steps, to accomplish the conversion of ethanoic
acid to 1,2-dichloroethane. For each step, give the reagent(s), reaction conditions
and structure of the intermediate. (3 marks)

##
(a) CH3OH + CO  CH3COOH 1
(b) Mass of atoms in 1 mole of CH3OH = (12.0 + 1.0 × 4 + 16.0) g = 32.0 g
Mass of atoms in 1 mole of CO = (12.0 + 16.0) g = 28.0 g
Mass of atoms in 1 mole of CH3COOH
= (12.0 × 2 + 1.0 × 4 + 16.0 × 2) g = 60.0 g 1

Atom economy = × 100% = 100% 1

(c) No by-product forms in process (2). 1

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Catalyst can speed up the reaction. More products can be obtained in a

relatively shorter period of time. 1
(d)
1
1. LiAlH4, dry ether
2. H+(aq)

1
conc. H2SO4
heat

1
Cl2(g)
(in organic solvent)

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##

Section 55.3
|!|CMELF0135500012|!|
Ethanol forms by reacting ethene with steam in the presence of phosphoric acid.
H3PO4
CH2=CH2(g) + H2O(g) CH3CH2OH(g)

(a) State the function of phosphoric acid. (1 mark)

(b) Calculate the atom economy of the above reaction.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

(c) State TWO green chemistry practices adopted by the process. (2 marks)

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##
(a) Phosphoric acid acts as a catalyst. 1
(b) Mass of atoms in 1 mole of CH2=CH2 = (12.0 × 2 + 1.0 × 4) g = 28.0 g
Mass of atoms in 1 mole of H2O = (1.0 × 2 + 16.0) g = 18.0 g
Mass of atoms in 1 mole of CH3CH2OH
= (12.0 × 2 + 1.0 × 6 + 16.0) g = 46.0 g 1

Atom economy = × 100% = 100% 1

(c) The use of phosphoric acid as catalyst can speed up the chemical reaction
and get more products in a relatively shorter period of time. 1
The atom economy of the process is 100%. 1
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##

|!|CMELF0135500013|!|
Esters can be prepared by the following two methods:
Method 1: CH3COCl + CH3CH2OH  CH3COOCH2CH3 + HCl
Method 2: CH3COOH + CH3CH2OH  CH3COOCH2CH3 + H2O

(a) Calculate the atom economy of the above two methods.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0, Cl = 35.5) (4 marks)

(b) Determine which method is greener for the preparation of ester. Give TWO

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reasons to support your answer. (2 marks)

##
(a) Mass of atoms in 1 mole of CH3COCl
= (12.0 × 2 + 1.0 × 3 + 16.0 + 35.5) g = 78.5 g
Mass of atoms in 1 mole of CH3COOH
= (12.0 × 2 + 1.0 × 4 + 16.0 × 2) g = 60.0 g
Mass of atoms in 1 mole of CH3CH2OH
= (12.0 × 2 + 1.0 × 6 + 16.0) g = 46.0 g
Mass of atoms in 1 mole of CH3COOCH2CH3
= (12.0 × 4 + 1.0 × 8 + 16.0 × 2) g = 88.0 g

For method 1, atom economy = × 100% 1

= 70.7% 1

For method 2, atom economy = × 100% 1

= 83.0% 1
(b) Method 2 is greener. The atom economy of method 2 is higher than that
of method 1. 1
Method 1 generates a corrosive acidic gas (HCl). However, method 2
only generates water as the by-product. Water is non-polluting. 1
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|!|CMELF0135500014|!|
Polyvinyl chloride is manufactured by heating chloroethene at about 60C in the
presence of a catalyst.

(a) Write an equation for the polymerization. (1 mark)

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(b) State ONE use of polyvinyl chloride. (1 mark)

(c) In terms of the following green chemistry principles, explain why manufacturing
polyvinyl chloride is NOT green.
(i) Producing safer chemical products (2 marks)

(ii) Designing degradable chemical products (2 marks)

##
(a)

1
(b) Making floor tiles / pipes / shower curtains / raincoats / artificial leather /
insulating coverings for electrical wire 1
(c) (i) PVC may release toxic chemicals. 1
Besides, burning PVC would form poisonous hydrogen chloride,
chlorine and dioxins. 1
(ii) PVC is non-biodegradable. 1
It stays in landfills for a very long time. 1
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|!|CMELH0135500015|!|

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

The flowing mercury cell and the membrane cell are widely used technology in the
chloroalkali industry.

(a) What is the raw material for chloroalkali industry? (1 mark)

(b) Write an overall equation for the electrolysis in chloroalkali industry. (1 mark)

(c) State ONE structural difference of the flowing mercury cell and the membrane
cell. (2 marks)

(d) State and explain which technology is greener. (2 marks)

##
(a) Brine (concentrated sodium chloride solution) 1
(b) 2NaCl(aq) + 2H2O(l)  2NaOH(aq) + Cl2(g) + H2(g) 1
(c) Any ONE:
- The cathode of the flowing mercury cell is made of mercury 1
while that of the membrane cell is made of nickel. 1
- An ion-permeable membrane is present in the membrane cell to
separate the anode and cathode compartment. (1)
In the flowing mercury cell, there is no such membrane. (1)
(d) The flowing mercury cell involves the use of poisonous mercury. Serious
environmental problems arise if mercury leaks from the cell. 1
However, the membrane cell does not involve the use of mercury. Hence,
the membrane cell uses less hazardous chemicals during the process. 1
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|!|CMELF0135500016|!|

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

Polyvinyl chloride (PVC) and polylactic acid (PLA) are common plastics used in
daily life. PLA is a type of new plastics developed recently. PLA is applied in making
food packaging. It can be degraded in the presence of oxygen. In terms of the
following green chemistry principles, explain why PLA is greener than PVC.

(a) Using renewable raw materials (2 marks)

(b) Producing safer chemical products (2 marks)

(c) Designing degradable chemical products (2 marks)

##
(a) The raw material for synthesizing PVC is chloroethene. It is obtained
from fossil fuels which are non-renewable resources. 1
However, the raw material for synthesizing PLA is corn starch which is a
renewable resource. 1
(b) PVC contains toxic substances. 1
However, PLA is not toxic as it can be used to make food packaging. 1
(c) PVC is non-biodegradable. It stays in landfills for a very long time. 1
However, PLA is biodegradable. 1
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|!|CMELH0135500017|!|
Ibuprofen is an anti-inflammatory drug. Its chemical structure is shown below:

(a) (i) Which type of stereoisomerism does ibuprofen exhibit? (1 mark)

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(ii) Suggest a way to distinguish the stereoisomers of ibuprofen. Explain briefly.

(2 marks)

(b) There are two methods for synthesizing ibuprofen.

A traditional synthetic method:

A new synthetic method:

In terms of the following green chemistry principles, explain which method is

greener.
(i) Reducing derivatives (2 marks)

(ii) Using catalysts (2 marks)

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##
(a) (i) Enantiomerism 1
(ii) The enantiomers can be distinguished by using a polarimeter. 1
They rotate the plane of polarized light to opposite directions. 1
(b) (i) The traditional method involves six steps while the new one
involves three steps only. 1
The traditional method generates more derivatives. More reagents
are needed and more waste will be generated. Hence, the new one is
greener. 1
(ii) The new method involves the use of palladium and nickel catalysts
while the traditional one does not. 1
Catalysts speed up the chemical reaction. More products can be
obtained in a relatively shorter period of time. Hence, the new one is
greener. 1
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|!|CMELH0135500018|!|
Ethylene oxide ((CH2CH2)O) is commonly used as a disinfectant in hospital for
sterilizing tools and equipment. It can be synthesized industrially by two methods ─
chlorohydrin process and direct oxidation of ethene.
Ca(OH)2
Chlorohydrin process
CH2=CH2 + Cl2 + H2O  OHCH2CH2Cl + HCl  (CH2CH2)O + CaCl2 + 2H2O

Direct oxidationAg
of ethene
2CH2=CH2 + O2  2(CH2CH2)O

(a) Calculate the atom economy of the above two reactions. (4 marks)
(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0, Cl = 35.5, Ca = 40.1)

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(b) Deduce, from THREE perspectives, which method is greener. (3 marks)

##
(a) Mass of atoms in 1 mole of CH2=CH2 = (12.0 × 2 + 1.0 × 4) g = 28.0 g
Mass of atoms in 1 mole of Cl2 = (35.5 × 2) g = 71.0 g
Mass of atoms in 1 mole of H2O = (1.0 × 2 + 16.0) g = 18.0 g
Mass of atoms in 1 mole of Ca(OH)2 = [40.1 + 2 × (16.0 + 1.0)] g = 74.1 g
Mass of atoms in 1 mole of (CH2CH2)O
= (12.0 × 2 + 1.0 × 4 + 16.0) g = 44.0 g
Mass of atoms in 1 mole of O2 = (16.0 × 2) g = 32.0 g
For chlorohydrin process, atom economy

= × 100% 1

= 23.0% 1

For direct oxidation of ethene, atom economy = × 100% 1

= 100% 1
(b) The direct oxidation of ethene is greener.
Any THREE:
- The atom economy of the direct oxidation of ethene is higher than

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that of chlorohydrin process. 1

- The chlorohydrin process involves the use of toxic chlorine.
However, the direct oxidation of ethene only uses non-toxic oxygen. 1
- The direct oxidation of ethene is a single-step synthesis. This
reduces the formation of derivatives. 1
- The direct oxidation of ethene uses silver as the catalyst. We can get
more products in a relatively shorter period of time. (1)
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|!|CMELH0135500019|!|
Esters are important ingredients in cosmetics and personal care products.

(a) Traditionally, esters are produced from esterification of an alcohol and a

carboxylic acid. State the conditions required. (2 marks)

(b) Recently, some scientists have investigated a new method for producing esters.
In the new method, enzymes are used to catalyse the esterification between
unsaturated fatty acids and alcohols at mild temperatures. In terms of the
following green chemistry principles, explain why the new method is greener
than the traditional one.
(i) Designing for energy efficiency (2 marks)

(ii) Using renewable raw materials (2 marks)

(iii) Using less hazardous chemical syntheses (2 marks)

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##
(a) Concentrated sulphuric acid is used as the catalyst. 1
The reaction mixture is heated under reflux. 1
(b) (i) The traditional method requires high temperatures while the new
method only requires mild temperatures. 1
Therefore, the new method can minimize the energy used. 1
(ii) The traditional method uses organic acids and alcohols as the raw
materials. They come from non-renewable petroleum. 1
However, the new method uses unsaturated fatty acids as the raw
materials. They come from vegetable oils which are renewable
resources. 1
(iii) The traditional method uses corrosive concentrated sulphuric acid as
the catalyst. 1
However, the new method uses enzymes as the catalyst. Hence, the
new method uses less hazardous chemicals during the synthesis. 1
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|!|CMELF0135500020|!|
In the Haber process, nitrogen and hydrogen is converted to ammonia in the presence
of a catalyst.

(a) Suggest a catalyst used in the conversion. (1 mark)

(b) State and explain the effect of the catalyst on the

(i) rate of reaction; (2 marks)

(ii) equilibrium position of the reaction. (2 marks)

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(c) State TWO green practices in Haber process. (2 marks)

##
(a) Finely divided iron 1
(b) (i) In the presence of the catalyst, the number of particles with energy
equal to or greater than the activation energy increases. 1
The number of effective collisions increases and hence the rate of
reaction increases. 1
(ii) The catalyst has no effect on the equilibrium position. 1
A catalyst increases the rates of both forward and backward
reactions to the same extent. 1
(c) Any TWO:
The atom economy of the reaction is 100% / the unused nitrogen and
hydrogen are recycled / the use of catalyst can reduce the use of energy. 2
(Accept other reasonable answers) ___
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##

|!|CMELA0135500021|!|
In the production of methanol, syngas is first produced from methane by steam-
methane reforming. Methanol can be manufactured from syngas.
CO(g) + 2H2(g) CH3OH(g) ΔH = 90 kJ mol1
Consider the following sets of reaction conditions:
Set A B C
Temperature 600C 260C 260C
Pressure 50100 atm 50100 atm 1 atm
Catalyst None Cu/ZnO/Al2O3 Cu/ZnO/Al2O3

(a) Which sets of conditions should best be adopted to give the highest yield of
methanol? Explain your choice with reference to each condition. (3 marks)

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(b) Explain why the use of catalyst complies with the principle of green chemistry.
(1 mark)

(c) In recent years, direct oxidation of methane to methanol has been the focus of
many researches. However, methanol is often further oxidized to methanal in the
process. Explain, in view of green chemistry, why it is worthwhile to develop
this new technique. (2 marks)

##
(a) Set B should be adopted. 1
As the forward reaction is exothermic, a lower temperature shifts the
equilibrium position to the right. A lower temperature is favoured. 1
Since there is greater number of moles of gas at the left-hand side of the
equation, a high pressure shifts the equilibrium position to the right. A
higher pressure is favoured. 1
(b) The use of catalyst can reduce the use of energy / the catalysed reaction is
more efficient as more products can be obtained in a relatively shorter
period of time. 1
(c) In the single-step direct oxidation of methane, no derivatives or
intermediates form. 1
This helps minimize the use of energy and reagents. 1
(Accept other reasonable answers) ___
6
##

|!|CMELF0135500022|!|
Englerin-A is a compound that can be extracted from plants. It is a potential drug for
cancer. In one of the synthetic steps of englerin-A, compound C forms when

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

compounds A, B and zinc metal are heated under reflux.

+Zn benzene +ZnBr2

+ 25C
reflux

A B C
Molar mass: Molar mass: Molar mass:
152.0 206.9 280.0

(a) Draw a labelled diagram for the experimental set-up of the reaction. (2 marks)

(b) In an experiment, 0.300 g of A reacts with 0.523 g of B and 0.164 g of zinc. The
mass of C obtained is 0.474 g. Calculate the percentage yield of the reaction.
(Relative atomic masses: Zn = 65.4, Br = 79.9) (3 marks)

(c) Calculate the atom economy of the reaction. (2 marks)

(d) Is the reaction a green reaction? Explain briefly. (1 mark)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

##
(a)

water out

reflux condenser

water in

reaction mixture
anti-bumping
granule water bath

heat
Correct drawing 1
Correct labels 1

(b) Number of moles of A used = = 0.00197 mol

Number of moles of B used = = 0.00253 mol

Number of moles of zinc used = = 0.00251 mol 1

From the equation, mole ratio of A : B : Zn = 2 : 2 : 1.

∴ A is the limiting reactant.
Theoretical mass of C formed = 280.0 g mol1 × 0.00197 mol = 0.552 g 1

∴ Percentage yield = × 100% = 85.9% 1

(c) Atom economy = × 100% 1

= 71.5% 1
(d) This is a green reaction as it has a fairly high atom economy. / This is
NOT a green reaction as it requires the use of benzene which is
carcinogenic. (Accept other reasonable answers.) 1
___

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

8
##

|!|CMELH0135500023|!|
Traditionally, propylene glycol is manufactured from the hydrolysis of propylene
oxide. The product of the reaction is a mixture of propylene glycol, dipropylene
glycol and tripropylene glycol. Recently, a new production method has been
developed. The starting material for the new method is glycerol, which is a by-product
in the production of biofuel from vegetable oil. A transition metal catalyst is used in
the reaction. The overall reaction is shown below.
CH2(OH)CH(OH)CH2OH(g) + H2(g) CH2(OH)CH(OH)CH3(g) + H2O(g)

(a) Name the process used to obtain glycerol directly from vegetable oil. (1 mark)

(b) Calculate the atom economy for the new method.

(Relative atomic masses: H = 1.0, C = 12.0, O = 16.0) (2 marks)

(c) Explain, in TWO different perspectives, why the new method is greener than the
traditional method. (2 marks)

(d) Explain why a high pressure is used in the new method. (1 mark)

(e) It is found that the percentage yield of the new method is 73.0%. In a microsacle
experiment, a chemist wants to obtain 14.0 g of propylene glycol using the new
method. Calculate the mass of glycerol needed. (2 marks)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

##
(a) Alkaline hydrolysis / saponification 1
(b) Mass of atoms in 1 mole of CH2(OH)CH(OH)CH2OH
= (12.0 × 3 + 1.0 × 8 + 16.0 × 3) g = 92.0 g
Mass of atoms in 1 mole of H2 = (1.0 × 2) g = 2.0 g
Mass of atoms in 1 mole of CH2(OH)CH(OH)CH3
= (12.0 × 3 + 1.0 × 8 + 16.0 × 2) g = 76.0 g 1

Atom economy = × 100% = 80.9% 1

(c) Any TWO:

- Glycerol is a renewable resource that is readily available in plants.
However, propylene oxide is produced from petrochemical industry. 1
- The use of catalyst in the new method allows more products to be
obtained in a shorter period of time. This saves energy and the cost
of production. 1
- Fewer by-products form in the new method. (1)
(d) At higher pressure, reactant particles have a greater chance to collide. 1

(e) Theoretical yield of propylene glycol = = 19.2 g

Number of moles of propylene glycol needed = = 0.253 mol 1

From the equation, mole ratio of glycerol : propylene glycol = 1 : 1.

Mass of glycerol needed = 0.253 mol × 92.0 g mol1 = 23.3 g 1
___
8
##

|!|CMELA0135500024|!|
Dilute hydrogen peroxide (H2O2) solution is used in paper bleaching.

(a) H2O2 decomposes slowly at room conditions.

(i) Suggest a catalyst for the decomposition. (1 mark)

(ii) Explain briefly why the catalyst can speed up the decomposition. (1 mark)

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

(iii) With the help of a Maxwell-Boltzmann distribution curve, explain why the
decomposition of H2O2 is faster at 60C than at 25C. (3 marks)

(b) The following two methods can be used to synthesize H2O2.

(1) Two-stage process involving an organic compound, anthraquinone
Stage 1: H2 + anthraquinone  anthraquinol
Stage 2: O2 + anthraquinol  H2O2 + anthraquinone
(2) The reaction of barium peroxide (BaO2) with sulphuric acid
BaO2(s) + H2SO4(aq)  BaSO4(s) + H2O2(aq)

(i) Calculate the atom economy of method (2).

(Relative atomic masses: H = 1.0, O = 16.0, S = 32.1, Ba = 137.3) (2 marks)

(ii) Besides atom economy, suggest TWO reasons why method (1) is greener
than method (2). (2 marks)

##
(a) (i) Manganese(IV) oxide / MnO2 1

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

(ii) The catalyst provides an alternative reaction pathway with lower

activation energy for the decomposition of H2O2 to proceed. 1
(iii)

Number of particles

25C

60C

Ea Kinetic energy

Correct sketching of the two curves 1

Correct labelling of axes 1
At a higher temperature, the number of particles possessing energy
equal to or greater than the activation energy increases. Hence, the
number of effective collisions per unit time increases. 1
(b) (i) Mass of atoms in 1 mole of BaO2 = (137.3 + 16.0 × 2) g = 169.3 g
Mass of atoms in 1 mole of H2SO4 = (1.0 × 2 + 32.1 + 16.0 × 4) g
= 98.1 g
Mass of atoms in 1 mole of H2O2 = (1.0 × 2 + 16.0 × 2) g = 34.0 g 1

Atom economy = × 100% = 12.7% 1

(ii) The use of anthraquinone as a catalyst can eliminate the generation

of by-products. 1
More products can be obtained in a relatively shorter period of time. 1
(Accept other reasonable answers) ___
9
##

|!|CMELH0135500025|!|
Melamine (C3H6N6) is an organic compound widely used in plastic industry. The
structure of melamine is shown below:

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

It can be synthesized from urea in an industrial process, in which urea (NH2CONH2)

decomposes to give melamine, carbon dioxide and ammonia.

(a) Calculate the percentage by mass of nitrogen in melamine. (1 mark)

(b) Write a chemical reaction of synthesizing melamine from urea. (1 mark)

(c) Melamine can also be synthesized by heating dicyandiamine ((NH2)2C=NCN)

above its melting point. Write an equation for the reaction involved. (1 mark)

(d) Which synthetic route of melamine, using urea or dicyandiamine as the starting
material, is greener? Give TWO reasons to support your answer. (2 marks)

##
(a) Percentage by mass of nitrogen in C3H6N6

= × 100% = 66.7% 1

(b) 6NH2CONH2  C3H6N6 + 6NH3 + 3CO2 1

(c) 3(NH2)2C=NCN  2C3H6N6 1
(d) The synthetic route using dicyandiamine as the starting material is greener.
The atom economy of the reaction is 100%. 1
No ammonia gas is produced in the process. 1
(Accept other reasonable answers) ___
5

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

##

|!|CMELH0135500026|!|
Vitamin C can be found in citric fruits. It can be produced by the Reichstein process.
The following table shows the steps in Reichstein process.
Step 1 Glucose is reduced to sorbitol by hydrogenation.
Step 2 Sorbitol is oxidized to sorbose by fermentation.
Step 3 Sorbose is converted to an intermediate compound called KGA.
Step 4 KGA undergoes condensation using a catalyst to give vitamin C.
Step 5 Vitamin C is purified by recrystallization.

(a) Explain why there is a need to produce vitamin C industrially. (1 mark)

(b) Name a catalyst that can be used in step 1. (1 mark)

(c) The following equation represents the reaction for step 2:

Explain why common oxidizing agents such as acidified potassium

permanganate solution are NOT used in this step. (1 mark)

(d) Suggest TWO reasons why the Reichstein process is a green process. (2 marks)

##
(a) The supply of vitamin C from plants cannot meet the worldwide
demand / there is an inadequate and shrinking supply of natural vitamin
C. 1

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 HKDSE CHEMISTRY — A Modern View (Second Edition)
Part XIII Industrial chemistry

(b) Platinum 1
(c) Other hydroxyl groups in sorbitol will also be oxidized by common
oxidizing agents. 1
(d) Any TWO:
Glucose is a renewable raw material / fermentation can reduce the use of
hazardous chemicals / the use of catalyst in step 4 can speed up the
reaction. (Accept other reasonable answers) 2
___
5
##

© Aristo Educational Press Ltd 2015 Chapter 55