Ch37 (EE)

37 Green
Chemistry
37.1 Concepts of Green Chemistry
37.2 Some Green Chemistry Practices
1 New Way Chemistry for Hong Kong A-Level 3B

37.1
Concepts of
Green Chemistry

37.1 Concepts of Green Chemistry (SB p.207)
Introduction
• Chemical industry has been very
important in manufacturing
 drugs for our health
 fertilizers and pesticides
 various important products
(e.g. polymers, dyes, cosmetics)
• Our living qualities have been improved

Introduction
The manufacture of these chemical

products improve our living qualities
Sustainable Development and

Green Chemistry
• First came out of the United Nations
Commission on Environment and Development
in 1987 (Brundtland Commission)
• Defined sustainable development as:
“...... Meeting the needs of the present without

compromising the ability of future generations
to meet their own needs.”


Green Chemistry
• The Earth has a limited natural capacity
 for diluting and assimilating the waste
and pollutants that the human society
generates


Green Chemistry
• With rapidly rising population and
industrialization in recent decades,
 that capacity is exceeded
 our lifestyle is not sustainable


Green Chemistry
Promotion of
sustainable
development
in Hong Kong

Green Chemistry
The disposal problem

of computer waste is
one of the concerns
of sustainable
development


Green Chemistry
• During the early 1990s,
 the US Environmental Protection Agency
(EPA) coined the phrase “green chemistry”
 promote innovative chemical technologies
 reduce or eliminate the use or generation
of hazardous substances in the design,
manufacture and use of chemical products

Green Chemistry
• Green chemistry is the use of chemistry
for prevention of pollution problems
 involves the design of chemical
products and processes that are
environmentally benign


Green Chemistry
• Green chemistry covers all aspects and
types of chemical processes
 reduce negative impacts to
human health and the environment


Green Chemistry
• Green chemistry is environmentally benign
 links the design of chemical products
and processes with their impacts on
human health and the environment
Example
37-1
37.2
Some Green
Chemistry Practices

37.2 Some Green Chemistry Practices (SB p.209)
Decaffeination using Supercritical

Carbon Dioxide
1. Caffeine
• Occurs naturally in tea, coffee, cocoa and

chocolate products
• Added to soft drinks and a variety of both
prescription and over-the-counter drugs

1. Caffeine
• Major action:
 stimulate the central nervous system
 make people less sleepy
• Also a mild painkiller that can relieve pains

1. Caffeine
Tea, coffee and cocoa

contain caffeine
Caffeine is added
to soft drinks and
some drugs
1. Caffeine
• The IUPAC name of caffeine is
1,3,7-trimethylxanthine
• Molecular formula: C8H10N4O2
• Caffeine is white in colour and has a
bitter taste

1. Caffeine
Ball-and-stick model of Structural formula of

caffeine caffeine

2. Decaffeinated Coffee
• Coffee naturally contains caffeine

• Some people like caffeine for its stimulating
effect as well as its characteristic taste

• There are people who do not want
caffeine for health or other reasons
 can opt for decaffeinated coffee
 coffee without caffeine (or more
accurately with very low caffeine level)

Decaffeinated
coffee

3. Decaffeination
• The first decaffeinated coffee was made by
 extracting the caffeine from green
coffee beans with trichloromethane
• Since then various organic solvents (e.g.
benzene and trichloroethane) were used
 all toxic
 caused environmental and health
concerns
3. Decaffeination
• In early 1970s,
 dichloromethane, CH2Cl2, became the
solvent of choice
 1. its lower toxicity
2. its ability to selectively dissolve
caffeine without carrying off sugars,
peptides, and flavor ingredients

3. Decaffeination
• Later evidence suggested that

 dichloromethane might be
carcinogenic
 its use was sharply reduced

3. Decaffeination
• Currently, three main methods used

for decaffeination of coffee are:
 water decaffeination
 carbon dioxide decaffeination
 solvent decaffeination

3. Decaffeination
• Water decaffeination and carbon dioxide

decaffeination
 commonly used by major manufacturers
• Solvent decaffeination
 governed by legislation

3. Decaffeination
• In solvent decaffeination
 the solvent commonly used is
dichloromethane (CH2Cl2)
 may cause both environmental and
health concerns

Decaffeination using supercritical
carbon dioxide
Carbon dioxide
behaves as a
supercritical fluid
above its critical
temperature
(31°C) and
pressure (73
atm)
Phase diagram of
carbon dioxide
carbon dioxide
• Supercritical carbon dioxide is a nearly
ideal solvent
• Under normal conditions, carbon dioxide
is not a very good solvent for organic
substances
• Supercritical carbon dioxide readily
dissolves many of these substances,
including caffeine
carbon dioxide
• The use of supercritical carbon dioxide

to replace dichloromethane in extracting
caffeine from coffee beans is a green
chemistry practice
• Compared to dichloromethane,
 carbon dioxide is non-toxic and does
not cause environmental problems

Use of Hydrogen Peroxide as a

Bleaching Agent
• Bleaching agents are used to remove

colours from materials
• Very important in both textile industry and
household cleaning


Bleaching Agent
• The most common household bleaching

agent is chlorine bleach
 contains hypochlorite as the active
ingredient


Bleaching Agent
Chlorine bleach has several disadvantages:
• chlorine gas may evolve during the
bleaching process
• poisonous chlorinated organic
compounds may be formed during the
bleaching process
 causing environmental problems

Bleaching Agent
• Hydrogen peroxide (H2O2) is a viscous
liquid that has strong oxidizing power
• Available in various concentrations
 including 6%, 30% and 50%


Bleaching Agent
• Aqueous solutions of 3% hydrogen
peroxide are often used as a bleach and
as a topical antiseptic
• Commercial hair bleaches also contain
hydrogen peroxide at 6% concentration


Bleaching Agent
• Hydrogen peroxide bleaches by oxidation


Bleaching Agent
• Hydrogen peroxide is reduced to water
which is non-polluting
• The process is environmentally friendly
• Hydrogen peroxide acts as a green
bleaching agent


Bleaching Agent
• The use of a catalyst (e.g.
manganese(IV) oxide)
 greatly increases the rate of
bleaching action of hydrogen peroxide

Use of Hydrogen Peroxide as a Green

Bleaching Agent in Industry
• In paper manufacturing,
 chlorine is commonly used to remove
wood pulp from lignin
• However, the use of chlorine gives rise to
environmental problems
 the reaction of lignin with
chlorine to give dioxin as the by-product


• Dioxin is a carcinogen
 causes various health problems
 can pass along food chain and
accumulate in food products like dairy
products, pork, beef and fish
• In view of this, the use of chlorine in the
process has been discouraged

• Hydrogen peroxide was used as a bleaching
agent in the presence of the TAML iron(III)
activators
• The TAML activator acts as a catalyst
 promotes the conversion of hydrogen
peroxide into hydroxyl radicals that are
involved in the bleaching process


• The reaction product is water which is
harmless
• The catalytic activity of TAML activators
allows
 hydrogen peroxide to break down
more lignin in a shorter time and at a
much lower temperature
Check Point
43 New Way Chemistry for Hong Kong A-Level 3B 37-2
The END

Back
In what ways can green chemistry contribute to achieving

sustainability?
Answer
Green chemistry can contribute to achieving sustainability in three key
areas:
(1) It is used to harness renewable energy technologies like utilization
of solar energy, making of fuel cells and so on.
(2) Green chemists can help the switching of the reagents used
mostly derived from petroleum to renewable sources so as to
reduce our dependence on fossil fuels.
(3) Green chemistry works on the replacement of polluting
technologies by environmentally benign alternatives. Hence, it can
reduce pollution and waste production.
Back
(a) What is a hydroxyl radical?

(b) Hydroxyl radical bleaches by oxidation. Explain its
oxidizing property.
Answer
(a) Hydroxyl radical carries an odd electron (i.e. unpaired electron)
on the oxygen atom.
(b) The hydroxyl radical is highly reactive. It tends to accept an

electron in reaction so as to achieve an octet electronic
configuration of the oxygen atom. That explains why it is a strong
oxidizing agent.

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37 Green

1 New Way Chemistry for Hong Kong A-Level 3B

2 New Way Chemistry for Hong Kong A-Level 3B

3 New Way Chemistry for Hong Kong A-Level 3B

The manufacture of these chemical

Sustainable Development and

“...... Meeting the needs of the present without

5 New Way Chemistry for Hong Kong A-Level 3B

Sustainable Development and

6 New Way Chemistry for Hong Kong A-Level 3B

Sustainable Development and

7 New Way Chemistry for Hong Kong A-Level 3B

Sustainable Development and

Sustainable Development and

The disposal problem

9 New Way Chemistry for Hong Kong A-Level 3B

Sustainable Development and

Sustainable Development and

11 New Way Chemistry for Hong Kong A-Level 3B

Sustainable Development and

12 New Way Chemistry for Hong Kong A-Level 3B

Sustainable Development and

14 New Way Chemistry for Hong Kong A-Level 3B

Decaffeination using Supercritical

• Occurs naturally in tea, coffee, cocoa and

15 New Way Chemistry for Hong Kong A-Level 3B

16 New Way Chemistry for Hong Kong A-Level 3B

Tea, coffee and cocoa

18 New Way Chemistry for Hong Kong A-Level 3B

Ball-and-stick model of Structural formula of

19 New Way Chemistry for Hong Kong A-Level 3B

• Coffee naturally contains caffeine

20 New Way Chemistry for Hong Kong A-Level 3B

21 New Way Chemistry for Hong Kong A-Level 3B

22 New Way Chemistry for Hong Kong A-Level 3B

24 New Way Chemistry for Hong Kong A-Level 3B

• Later evidence suggested that

25 New Way Chemistry for Hong Kong A-Level 3B

• Currently, three main methods used

26 New Way Chemistry for Hong Kong A-Level 3B

• Water decaffeination and carbon dioxide

27 New Way Chemistry for Hong Kong A-Level 3B

28 New Way Chemistry for Hong Kong A-Level 3B

• The use of supercritical carbon dioxide

31 New Way Chemistry for Hong Kong A-Level 3B

Use of Hydrogen Peroxide as a

• Bleaching agents are used to remove

32 New Way Chemistry for Hong Kong A-Level 3B

Use of Hydrogen Peroxide as a

• The most common household bleaching

33 New Way Chemistry for Hong Kong A-Level 3B

Use of Hydrogen Peroxide as a

Use of Hydrogen Peroxide as a

35 New Way Chemistry for Hong Kong A-Level 3B

Use of Hydrogen Peroxide as a

36 New Way Chemistry for Hong Kong A-Level 3B

Use of Hydrogen Peroxide as a

37 New Way Chemistry for Hong Kong A-Level 3B

Use of Hydrogen Peroxide as a

38 New Way Chemistry for Hong Kong A-Level 3B

Use of Hydrogen Peroxide as a

39 New Way Chemistry for Hong Kong A-Level 3B

Use of Hydrogen Peroxide as a Green