Saponification

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Saponification

Saponification is the hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
of an ester

Ester

An ester is an often Aroma compound organic chemistry or partially organic compound formed by the reaction between an acid and an alcohol or aromatic alcohol with the elimination of water....
under basic

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
conditions to form an alcohol

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
and the salt

Salt

A salt, in chemistry, is defined as the product formed from the neutralisation reaction of acids and base . Salts are ionic compounds composed of cations and anions so that the product is electrically electric charge ....
of a carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
(carboxylates). Saponification is commonly used to refer to the reaction of a metallic alkali (base

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
) with a fat

Fat

Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. Chemistry, fats are generally ester of glycerol and fatty acids....
or oil

Oil

An oil is a chemical substance that is in a viscosity liquid state at room temperature or slightly warmer, and is both hydrophobic and lipophilic ....
to form soap

SOAP

SOAP, originally defined as Simple Object Access Protocol, is a protocol specification for exchanging structured information in the implementation of Web Services in computer networks....
. Saponifiable substances are those that can be converted into soap.

Sodium hydroxide

Sodium hydroxide

Sodium hydroxide , also known as lye, caustic soda and sodium hydrate, is a caustic metallic Base . Sodium hydroxide forms a strong alkaline solution when dissolved in a solvent such as water, however, only the hydroxide ion is basic....
(NaOH) is a caustic base. If NaOH is used a hard soap is formed, whereas when potassium hydroxide

Potassium hydroxide

Potassium hydroxide is the inorganic compound with the formula potassiumhydroxide. Along with sodium hydroxide, this colourless solid is a prototypical "strong base"....
(KOH) is used, a soft soap is formed.

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Encyclopedia

Saponification is the hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which one or more water are split into hydrogen and hydroxide ions which may go on to participate in further reactions....
of an ester

Ester

Base (chemistry)

Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
and the salt

Salt

Carboxylic acid

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
) with a fat

Fat

Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. Chemistry, fats are generally ester of glycerol and fatty acids....
or oil

Oil

An oil is a chemical substance that is in a viscosity liquid state at room temperature or slightly warmer, and is both hydrophobic and lipophilic ....
to form soap

SOAP

Sodium hydroxide

Potassium hydroxide

Animal fat

Animal fats are Rendering tissue fat that can be obtained from a variety of animals....
s are fatty esters in the form of triglyceride

Triglyceride

is a glyceride in which the glycerol is esterified with three fatty acids. It is the main constituent of vegetable oil and animal fats....
s. The alkali breaks the ester bond and releases the fatty acid

Fatty acid

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail , which is either saturation or Unsaturated compound....
salt and glycerol

Glycerol

Glycerol is a chemical compound also commonly called glycerin or glycerine. It is a colorless, odorless, Viscosity liquid that is widely used in pharmaceutical formulations....
. If necessary, soaps may be precipitated

Precipitation (chemistry)

Precipitation is the formation of a solid in a solution during a chemical reaction. When the reaction occurs, the solid formed is called the precipitate, and the liquid remaining above the solid is called the supernate....
by salting it out

Salting out

Salting out is a method of separating proteins based on the principle that proteins are less soluble at high salt concentrations. The salt concentration needed for the protein to precipitate out of the solution differs from protein to protein....
with saturated

Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
sodium chloride

Sodium chloride

Sodium chloride, also known as common salt, table salt, or halite, is a chemical compound with the chemical formula SodiumChlorine....
. The saponification value

Saponification value

Saponification value represents the number of milligrams of potassium hydroxide or sodium hydroxide required to saponification 1g of fat under the conditions specified....
is the amount of base required to saponify a fat sample.

In a classic laboratory procedure the triglyceride trimyristin

Trimyristin

Trimyristin is an ester with the chemical formula C45H86O6. It is a saturated fat which is the triglyceride of myristic acid....
is obtained by extracting nutmeg

Nutmeg

The nutmegs Myristica are a genus of evergreen trees indigenous to tropical southeast Asia and Australasia. They are important for two spices derived from the fruit, nutmeg and mace....
with diethyl ether

Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
. Saponification to the sodium salt of myristic acid

Myristic acid

Myristic acid, also called tetradecanoic acid or 14:0 is a common saturated fatty acid with the molecular formula CH312COOH....
takes place with NaOH in water. The acid itself can be obtained by adding dilute hydrochloric acid

Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
. .

Mechanism

The reaction mechanism

Reaction mechanism

In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs .Although only the net chemical change is directly observation for most chemical reactions, experiments can often be designed that suggest the possible sequence of steps in a reaction mechanism....
is based on nucleophilic acyl substitution

Nucleophilic acyl substitution

Nucleophilic acyl substitution describes the substitution reaction involving nucleophiles and acyl compounds. Acyl compounds are carboxylic acid derivatives including esters, amides and acid halides....
. Attack of the hydroxyl anion on the carbonyl group of the ester gives an orthoester

Orthoester

In organic chemistry, an orthoester is a functional group containing three alkoxy groups attached to one carbon atom. The name can also refer to any organic compound that contains this functional group....
:

The carbonyl group reforms with generation of an carboxylic ester and an alkoxide

Alkoxide

An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They can be written as RO–, where R is the organic substituent....
:

This alkoxide is less acidic than the acid and proton transfer takes place in step three

Corpses

Saponification can also refer to the other soft tissue in a conversion of the fat of a corpse into adipocere

Adipocere

Adipocere or grave wax or mortuary wax is a water-insoluble material consisting mostly of saturated fatty acids. It is formed by the slow hydrolysis of fats in decomposing material such as a human cadaver by action of anaerobic bacteria....
, often called "grave wax." This process is more common where the amount of fatty tissue

Adipose tissue

In histology, adipose tissue or fat is loose connective tissue composed of adipocytes. Adipose tissue is derived from lipoblasts. Its main role is to store energy in the form of fat, although it also cushions and Thermal insulation the body....
is high, the agents of decomposition

Decomposition

Decomposition refers to the process by which tissues of dead organisms break down into simpler forms of matter. Such a breakdown of dead organisms is essential for new growth and development of living organisms because it recycles the finite chemical constituents and frees up the limited physical space in the biome....
are absent or only minutely present, and the burial ground is particularly alkaline.

Fire extinguishers

Fires involving cooking fats and oils (classified as Class K

Fire classes

In firefighting, fires are identified according to one or more fire classes. Each class designates the fuel involved in the fire, and thus the most appropriate fire control....
) burn hotter than other typical combustible liquids, rendering a standard class B extinguisher ineffective. Such fires should be extinguished with a wet chemical extinguisher

Fire extinguisher

A fire extinguisher is an active fire protection device used to extinguish or control small fires, often in emergency situations. It is not intended for use on an out-of-control fire, such as one which has reached the ceiling, endangers the user , or otherwise requires the expertise of a fire department....
. Extinguishers of this type are designed to extinguish cooking fats and oils through saponification. The extinguishing agent rapidly converts the burning substance to a non-combustible soap. This process is endothermic

Endothermic

In thermodynamics, the word endothermic "within-heating" describes a process or reaction that absorbs energy in the form of heat. Its etymology stems from the Greek prefix endo-, meaning ?inside? and the Greek suffix ?thermic, meaning ?to heat?....
, meaning it absorbs thermal energy

Thermal energy

Thermal energy is a form of energy that manifests itself as an increase of temperature. It is also the sum of sensible heat and latent heat....
from its surroundings, decreasing the temperature and eliminating the fire.

External links

- Soapmaking articles, forum and supplier links.
- Resources for natural handmade soapmakers.
- Soapmaking explained.
- Soap making at About.com
- A collection of terms, definitions and acronyms for today's soap maker.
- A book from 1908.

Saponification

Mechanism

Corpses

Fire extinguishers

See also

External links