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Saponification

What is Saponification

The process of converting fats, oil, and lipid into soap using an aqueous alkali is called saponification. Vegetable oil and animal fats are triesters, called triglycerides, that can be saponified in one or two steps. During this process, the triglyceride reacts with an aqueous hydroxide ion to form a mixture of glycerol and fatty acid derivative. The sodium or potassium salts of long-chained fatty acids are a significant component of soap [1-6].

General Equation for Saponification

During saponification, esters are cleaved in the presence of aqueous alkali to form an alcohol and an alkali-metal salt of carboxylic acid. The alkali used in this process is sodium hydroxide (NaOH) or lye for hard soap and potassium hydroxide (KOH) for soft soap.

The general reaction, using NaOH, is given by:

RCOOR’ + NaOH → ROH + R’COO Na+

Saponification

Examples of Saponification [2-6]

1. Sodium stearate

Sodium stearate (C18H35NaO2) is the sodium salt of stearic acid (C18H36O2). It is used as a soap and a detergent. It is a significant component of soaps and contains both a hydrophobic and a hydrophilic part. It is produced when glyceryl tristearate ((C18H35O2)3C3H5), the triglyceride of stearic acid, is hydrolyzed with aqueous sodium hydroxide (NaOH).

(C18H35O2)3C3H5 + 3 NaOH → C3H5(OH)3 + 3 C18H35O2Na

2. Sodium palmitate

Sodium palmitate (C16H31NaO2) is the sodium salt of fatty palmitic acid (C16H32O2). It is found in soaps and detergents. It can be derived by the saponification of glyceryl palmitate ((C16H31O2)3C3H5) using sodium hydroxide (NaOH) in the form of caustic soda, lye, or lime.

(C16H31O2)3C3H5 + 3 NaOH → C3H5(OH)3 + 3 C16H31O2Na

3. Methyl salicylate

Methyl salicylate (HOC6H4COOCH3) reacts with sodium hydroxide (NaOH) to form a thick white solid of sodium salicylate (HOC6H4COONa+).

HOC6H4COOCH3 + NaOH → HOC6H4COONa+ + CH3OH

4. Methyl acetate

Methyl acetate (CH3COOCH3) saponifies in the presence of sodium hydroxide (NaOH) to sodium acetate (CH3COONa+).

CH3COOCH3 + NaOH → CH3COONa+ + CH3OH.

5. Methyl benzoate

Methyl benzoate (C8H8O2) reacts with aqueous sodium hydroxide (NaOH) to give sodium benzoate (water-soluble) and methanol (miscible with water).

C8H8O2 + NaOH → C7H5O2Na + CH3OH

Saponification Reaction Example

Saponification Mechanism

The mechanism of saponification is a nucleophilic carbonyl substitution process, which is explained in the following steps [4-6].

Step 1: The nucleophilic hydroxide ion attacks the ester group and forms an intermediate.

Step 2: The intermediate splits by releasing the leaving group to form a carboxylic acid and an alkoxide.

Step 3: Deprotonation removes the hydrogen from the carboxylic acid resulting in a carboxylate ion and alcohol.

Saponification Reaction Mechanism

Saponification Value

Saponification value (SV) or saponification number (SN) represents the number of milligrams of potassium hydroxide (KOH) required to saponify one gram of fat under a specific condition. The saponification value is a significant parameter used to characterize and evaluate the quality of edible fats and oils. Also, the saponification number provides information about the fatty acids’ average molecular weight. The higher the number, the lower the molecular weight of all fatty acids [7].

Unit: mg KOH/g

The following table gives the saponification values of various oils and fats.

Oil/ fatSaponification value (mg KOH/ g)
Canola oil182 – 193
Sunflower oil189 – 195
Olive oil184 – 196
Soyabean oil187 – 195
Coconut oil248 – 265
Cottonseed oil189 – 207
Palm kernel oil230 – 254
Palm oil190 – 209
Castor oil176 – 187

Applications of Saponification

The main application of saponification is in the manufacture of soaps. There are different kinds of soaps serving different purposes like laundry, cleaning, and lubrication. Soaps may be precipitated by salting them out with saturated sodium chloride. Saponification also works with fire extinguishers. Fire extinguishers use it to convert burning fats and oil into non-combustible soap, which helps to reduce the fire[7].

Saponification is also significant, especially in the food industry, because it helps to know the amount of free fatty acid present in a food item. The amount of free fatty acid can be distinguished by determining the amount of alkali added to the fat or oil to make it neutral.

Esterification vs. Saponification[8]

Why is Saponification the Reverse of Esterification

During esterification, acid and alcohol combine to form an ester and release water. On the other hand, saponification breaks the bonds in an ester to form alcohol and long-chained fatty acid derivative.

Example of Esterification

C2H5OH + CH3COOH → CH3COOC2H5OH + H2O

The following table shows the difference between saponification and esterification.

EsterificationSaponification
DefinitionProcess of preparing esterProcess of preparing soap
ProcessAcid reacts with alcohol in the presence of concentrated sulfuric acidEster reacts with aqueous alkali
HeatYesNo
CatalystAcidBase
ByproductWaterAlcohol

FAQs

Q.1. What is the purpose of ethanol in the saponification reaction?

Ans. Ethanol is less polar than water. It helps to dissolve the nonpolar fat so that it can react with sodium hydroxide.

Q.2. Is saponification reaction endothermic or exothermic?

Ans. Saponification reaction is endothermic as it takes heat from the surroundings.

References

  1. Web.fscj.edu
  2. Chem.ucla.edu
  3. Chem.latech.edu
  4. Web.fscj.edu
  5. Chem.libretexts.org
  6. Thoughtco.com
  7. Metrohm.com
  8. Differencebetween.com

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