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Lesson 11 Reactions of Esters

Esters are formed from a condensation reaction between an alcohol and a carboxylic acid. They have characteristic sweet or fruity fragrances and are used in food flavorings and perfumes. Esters can undergo hydrolysis when reacted with water, especially in the presence of an acid or base catalyst. Saponification and transesterification are examples of base-catalyzed hydrolysis, where triglycerides are broken down into glycerol and fatty acid salts or biodiesel, respectively.

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87 views

Lesson 11 Reactions of Esters

Esters are formed from a condensation reaction between an alcohol and a carboxylic acid. They have characteristic sweet or fruity fragrances and are used in food flavorings and perfumes. Esters can undergo hydrolysis when reacted with water, especially in the presence of an acid or base catalyst. Saponification and transesterification are examples of base-catalyzed hydrolysis, where triglycerides are broken down into glycerol and fatty acid salts or biodiesel, respectively.

Uploaded by

dela2
Copyright
© © All Rights Reserved
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
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Reactions of Esters

Esters have fruity sweet-smelling fragrances.


What are they?
How are they made?
Formed when an alcohol reacts with a carboxylic
acid.
Very slow reaction, unless! an acid catalyst used
(usually sulphuric acid)
A condensation reaction
The condensation reaction between the hydroxyl
group and the carboxylic acid known as
esterification.
Reverse reaction = ester hydrolysis
Names of esters
Naming end in –oate.

Named after alcohol & carboxylic acid from which


they are derived.
O let’s name
some esters!
C CH3
CH3 CH2 O
ethyl ethanoate

this part comes from the this part from the acid
alcohol & is named after it and is named after it
Structural formulae
Although the previous structural formula are the clearest
way of showing esters, they can draw out in a
shortened form. In this version
the acid part
ethyl ethanoate has been
Or…
O written first
Either… O
CH3 C O CH2 CH3
CH3 CH2 O C CH3
 Identify the group attached to the C=O – this is from
the acid
 The group attached to the –O- is from the alcohol.
Wait! What’s that smell?
ester fragrance
ethyl methanoate raspberries
3-methylbutyl ethanoate pears
ethyl 2-methylbutanoate apples
phenylmethyl ethanoate jasmine

• Esters have strong, sweet smells.


• Their bouquet is often floral or fruity.
• This means they are used in food flavourings &
perfumes.
• Also, very good at dissolving organic compounds so
often used as solvents.
Ester hydrolysis

Breakdown of an ester by water.


Process sped up by catalysis
Can use an acid to catalyse (H2SO4)
Alkali catalysts (e.g. sodium hydroxide) can also
be used but instead of producing carboxylic acid
a carboxylate salt is formed.
Alkaline hydrolysis goes to completion & hence is
usually preferred.
Hydrolysis of Esters - Reaction with H2O
• Esters are hydrolyzed only slowly, even in boiling water
• hydrolysis becomes more rapid if they are heated with either aqueous acid or base

Acid Catalyzed Hydrolysis of Esters


 Hydrolysis in aqueous acid is the reverse of esterification
 The reaction is catalysed by dilute acid, and so the ester is heated under
reflux with a dilute acid like dilute hydrochloric acid or dilute sulphuric
acid.
dil. acid

reflux
Acid Catalyzed Hydrolysis of Esters
 Notice that the reactions are reversible.
 To make the hydrolysis as complete as possible, you would
have to use an excess of water.
 The water comes from the dilute acid, and so you would mix
the ester with an excess of dilute acid.
Note:
 HYDROLYSIS is favoured by dilute acid
 ESTERIFICATION is favoured by concentrated acid
Base Catalyzed Hydrolysis of Esters
 Hydrolysis of an ester in aqueous base is often called
saponification
 The ester is heated under reflux with a dilute alkali like sodium
hydroxide solution.

Advantages
 The reactions are one-way rather than reversible, and
 the products are easier to separate.
Example:

CH3COO-Na+ (aq) + CH3CH2CH2OH (aq)


propyl ethanoate base sodium ethanoate propan-1-ol
Saponification
• a process by which triglycerides are reacted with sodium or potassium
hydroxide to produce glycerol and a fatty acid salt, called 'soap'.
• Soaps are the sodium or potassium salts of long chain carboxylic acids.
• ‘soft’ toilet soap is generally made by the base hydrolysis of the esters in
vegetable oils
• If the large esters present in animal or vegetable fats and oils are heated with
concentrated sodium hydroxide solution exactly the same reaction happens
as with the simple esters.
• A salt of a carboxylic acid is formed - in this case, the sodium salt of a big
acid such as octadecanoic acid (stearic acid). These salts are the important
ingredients of soap
•Generally,
An alcohol is also produced - in this case, the more complicated alcohol,
propane-1,2,3-triol (glycerol).
Saponification
Example:

propane-1,2,3-triol
+ 3NaOH(aq) (glycerol)

Triglyceride +
(vegetable oil)

Sodium palmitate(a Soap)


Transesterification
• Transesterification - is the process by which esters exchange alkyl groups
with alcohols usually in the presence of a catalyst.

• Biodeisel production - is the act of producing the biofuel, biodiesel


through transesterification. The process involves reacting vegetable oils
or animal fats catalytically with short chain aliphatic alcohols (such as
methanol and ethanol)
• Biodiesel – a fuel composed of mono-alkyl esters of long chain fatty
acids derived from vegetable oils or animal fats.
• Almost all biodiesel is produced from virgin vegetable oils using base-
catalyzed technique requiring only low temperature and pressure at 98%
yield
Transesterification
Example:

KOH catalyst
+ 3CH3OH

Esters in vegetable oil methanol methyl esters propane-1,2,3-triol


(Biodiesel) (glycerol)

Note: do not confuse this process with saponification


Transesterification
• Transesterification can be either acid-catalyzed or base-catalyzed

• The majority of the alkyl esters produced today are done with the
base catalyzed reaction because it is the most economic for several
reasons:
o Low temperature (150 F) and pressure (20 psi) processing.

o High conversion (98%) with minimal side reactions and reaction time.

o Direct conversion to methyl ester with no intermediate steps.

o Exotic materials of construction are not necessary.

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