1st Year

Organic Chemistry
-Laboratory
___

Ateneo de Manila University

Mr. Jude Reyes
Crystallization: Recrystallization of
Benzoic Acid
Crystallization

Distillation: Identification of Unknown

Liquids
Simple Distillation

Simple Distillation Setup

Simple Distillation Techniques

Natural Product Extraction: Isolation of

Caffeine from Tea (Part 1)
Extraction
Types of Extraction
Isolation of Caffeine from Tea Leaves

Natural Product Extraction: Isolation of

Caffeine from Tea (Part 2)
Chromatography
Thin Layer Chromatography

Preparation of Soap
Soap Chemistry
Soap Making
Crystallization

Crystallization

● One of the steps usually involved in the purification of solid organic

compounds
○ Solid organic compounds are often impure.
■ They are prepared in the laboratory or extracted from natural
sources (i.e. leaves).
● Slow formation of a crystalline solid

General Process of Crystallization

● Success is based on differences in the solubilities of the compound and the

impurities.
○ Most compounds are more soluble in a hot solvent than a cold one
(solubility: hot>cold)

1. The crude compound is dissolved in a minimal amount of hot solvent.

○ Gravity filtration: Insoluble impurities separated from hot
solution.
○ If colored impurities are present, the solution is treated with
decolorizing charcoal and then filtered.
2. A hot, saturated solution is allowed to cool slowly so the desired
compound crystallizes at a moderate rate.
3. When crystals are fully formed, isolate them from the mother liquor
(solution) by filtration.

Crystallization vs. Precipitation

● Crystallization: slow formation

○ If the solution slowly cools down, impurities are likely excluded.
■ Crystal structure molecules are in equilibrium with solution
molecules.
 ■ Molecules unsuitable for crystal lattice return to solution.
■ Caveat: Impurities are often found in low concentration so
they remain in solution as solution cools.
○ More selective process

● Precipitation: rapid formation

○ If the solution is cooled too quickly, compound may precipitate.
■ Precipitate may still contain impurities.
To obtain pure compounds

● Recrystallization of the harvested crystals is often employed

○ But this is with the disadvantage of some loss of the desired
compound, which remains in the solution.
Prelab Answers

Benzoic acid has higher antimicrobial activity than sodium salt.

Why is sodium benzoate preferred over benzoic acid as a
preservative?

● The free acid form is poorly soluble in water and the sodium salt (sodium
benzoate) is often used because of its higher solubility in water (200 times
more soluble).

Why should you not place the hot crystallization solution

immediately in an ice bath?

● The system will favor the formation of a solid (any solid!) so strongly that
there may be little preference for purity. A rushed crystal formation will
trap impurities within the crystal lattice. Furthermore, the resulting
crystals will be smaller.

When the crystallization solution is allowed to slowly cool down,

a watch glass or beaker is used to cover the flask. This is to
prevent solvent evaporation. Why must it
be prevented?

● Some of the compounds of the solution can disappear in the air by

evaporation. To avoid recrystallization in the funnel as rapid
crystallization will occur if there is maximum evaporation.

In a laboratory session, when is the best time to put the flask

and funnel in the oven?
 ● During the first steps of the experiment ensure that it is hot by the time of
gravity filtration.

How do you avoid premature crystallization when filtering off

the insoluble impurities from the hot solution? How do you keep
the solution hot?
● If it is necessary to perform a hot filtration, it is prudent to add 2-5% of
solvent to prevent premature crystallization during this operation. If
adding solvent fails to dissolve any more solid, insoluble impurities are
likely present. These can be removed by hot filtration.
Simple Distillation

As mentioned in previous experiments on crystallization and extraction,

purifying a compound is a critical step in organic synthesis. It is very
important to free a compound of impurities, especially when its structure
is to be established or its physical properties are to be accurately
determined. Basic separation techniques, such as crystallization and
extraction, are employed to purify the compound of interest.

Boiling Point

● Useful molecular constant for the characterization and identification of

pure compounds.

Boiling Point Range

● A good measure of a liquid’s purity

History of Distillation

● Done as early as 1810 BC in Mesopotamia

○ Used to produce hundreds of liters of balms, essences, and incense
from natural products.
● Medieval times
○ Every alchemist’s laboratory housed a distillation setup

Distillation

● Used not only to separate and purify compounds but also to determine the
boiling points of certain substances.
● Simplest separation technique
○ Since this method dates back to ancient times and has undergone
countless improvisations
● Takes advantage that a boiling mixture initially gives off vapor which
constitutes the lower-boiling components of the mixture
○ Vapor can be condensed back to its liquid form, the distillate, which
is rich in low-boiling components
■ Original mixture is left with the higher boiling components
Simple Distillation Setup

Water Condenser

● the vapor emitted goes into it

● The vapor condenses due to continuous water flowing through the
condenser, which in turn goes into the receiving flask.
○ Water flow against gravity
● Water inlet - found near the mouth of the receiver adapter
 ● Water outlet -found near the still head.

Round Bottom Flask

● where a certain liquid is heated to boiling

Pot Liquid

● mixture in a round bottom flask

When pot liquid is heated to boiling

● molecules in the liquid move faster.

○ increase in the speed of molecular motion enables these molecules
to break away from intermolecular interactions and escape into the
gas phase
● Vaporization (liquid to gas) - endothermic

As heating continues

● amount of molecules in the vapor phase increases

● some of them tend to be pushed towards the condenser.
● Since condenser temp < inside the flask temp
■ the vapor condenses back into its liquid state.
● Condensation (gas to liquid) - exothermic

During heating

● thermometer temp will rapidly rise until the boiling point of the
lowest-boiling component (BP of LBC).
○ heat energy is being used to increase the temperature of the mixture
○ Based on Gay-Lussac’s law (pressure directly proportional to
temperature)

Once the temperature reaches BP of LBC

● temperature is constant until all of the low-boiling components are

distilled out.
 ● Vaporization (liquid to gas)
● Vapor temperature (VT) remains the same and pot liquid temperature (PT)
increases

VT remains the same and PT increases

● VT = BP of LBC
● VT remains constant until all of LBC has been distilled off.
● Heat energy is used for vaporization rather than increasing temperature

If other compounds are in the mixture

● temperature rise to the next boiling point

○ depending on the nearest low-boiling component
Simple Distillation Techniques

1. Once the pieces of glassware have been set up, highly recommended that
they be secured with rubber bands.
● prevent the pieces of glassware from slipping out
● Placement:
○ water outlet rubber band connected to still head neck
○ water inlet rubber band connected to receiver adapter neck
2. The flask and condenser are firmly secured by clamps
● clamps must be properly attached to stable iron stands.
3. The amount of mixture in the flask must not greatly exceed two-thirds of
the flask’s volume.
● For sufficient clearance above the surface of the liquid
○ liquid is not propelled into the condenser = compromising
distillate purity.
● ensure more efficient evaporation
○ larger surface area = more molecules are exposed to the heat
● liquid must also not be too little = the risk of the flask running dry
○ heat from the Bunsen burner could crack/shatter the flask
○ inaccurate results as not all components of the mixture may
have been distilled
4. Smooth and even boiling is important
● Ideally
○ heat source is a heating mantle or sometimes, an oil bath
○ For a liquid with BP < 90°C, water bath
● In this experiment
○ low-boiling liquids will be used
○ Boiling chips were added to facilitate even boiling
■ make sure no liquid spurts directly into the condenser
● For high-boiling compounds
○ air condenser or
 ○ air is allowed to pass through the water condenser jacket
instead of the water
5. Collecting several distillate fractions over certain temperature ranges is
required
● Happens because other impurities cause a deviation in the boiling
points of liquids
● Thus, there is a forerun
○ distillate collected even before the supposed boiling point
○ usually collected until the temperature remains constant or
when the change in temperature is minimal
● When the forerun is all collected
○ receiving flask is replaced by a new one which will collect
distillate over a constant temperature
● When the temperature suddenly rises
○ new flask will be collecting the distillate
6. Once the flask appears dry, immediately put off the heat source
● May contain substances, such as organic solids, which are explosive
at high temperatures
Extraction

Definition

● Separation technique
● Usually employed as part of the purification procedure in many organic
reactions.
● Transfer of a particular solute from one phase to another

Types of Extraction

Solid-Liquid Extraction

● Separation technique
● Isolation of natural products usually employs this type of extraction
○ Components in plants and animal tissues have a wide range of
polarities.
○ Selective extraction can be performed by using solvents of the right
polarity.
● Process
1. The specimen to be analyzed is finely ground and extracted with the
appropriate solvent.
2. The extract is separated from the residue and the residue is again
extracted with another solvent.
3. Depending on the polarity of the solvent used, the extracts contain
several families of compounds that can be separated and analyzed
through liquid-liquid extraction, chromatography, and distillation.
● Screening
○ process of extracting a group of compounds of similar properties
● Extraction of nonpolar compounds
○ E.g. petroleum ether
○ Uses a nonpolar solvent
 ● Solvent of medium to high polarity
○ E.g. methanol
○ used to extract pigments, alkaloids, tannins, flavonoids, and other
polar compounds.
● Water
○ used to remove salts, small sugars, proteins, and other very polar
compounds
● Example: leaves of a certain miracle plant believed to stop aging are
soaked in a particular liquid. The target molecules are extracted into the
liquid, processed, and packaged as a product that “makes you feel brand
new.”

2 Major Techniques in Solid-Liquid Extraction

● Batch Extraction
○ Solid specimen is mixed with the solvent and heated.
○ High temperatures and long extraction times = increase yield
■ But heating should only be done if the compounds to be
extracted are stable at high temperatures.
● Batch extraction is done when the component to be extracted is present in
great quantity or the yield of the process is a matter of little consequence.
Otherwise, continuous extraction which
● makes use of a Soxhlet apparatus is employed.

Liquid-Liquid Extraction

● Transfer of solute between two immiscible liquids

○ Immiscible liquids - usually water and an organic solvent.
● Transfer happens at the interface between the two liquid phases.
○ If one substance in the first liquid layer is more soluble in the second
layer
■ substance will transfer to the second liquid layer.
■ To speed up this transfer, the two liquids are vigorously
shaken.
 ■ Greater surface area, made possible by the formation of
droplets during shaking, allows more contact between the two
liquids and increases the rate of transfer of solute

Isolation of Caffeine from Tea Leaves

Process

● Involves both solid-liquid and liquid-liquid extractions.

● Initially
○ tea leaves are soaked in water, boiled, then filtered.
● Later on
○ Caffeine is isolated from the filtrate by washing with methylene
chloride.
○ Crude caffeine is then obtained when ethyl acetate evaporates.
● Cellulose
○ main component of tea leaves
○ material that makes up the principal structure of all plants.
○ polymer of glucose.
● Aside from the 2-3.5% caffeine content in tea leaves, proteins and amino
acids (3- 5%), polyphenols or tannins, pigments, and small amounts of
saponins are present.

Tannins

● phenolic compounds having molecular weights between 500 and 3000 Da.
● widely used to “tan” leather.
● Divided into two classes:
○ hydrolyzable tannins
■ most prominent in tea leaves
■ Due to their acidic character, the ester bonds are easily
hydrolyzed in the presence of a base to form glucose and gallic
acid salts.
 ■ From the reaction above, it can be inferred that tannins are
made up of a glucose backbone that is condensed with gallic
acid (galloyl and digalloyl groups)
○ Nonhydrolyzable tannins
■ condensation polymers of catechin are formed by linking at
ring positions 4 and 8.

Pigments such as chlorophyll and flavonoids give color to plants.

● The brown color of a tea solution is due to:

○ presence of the flavonoid pigments and chlorophylls
○ their respective oxidation numbers.

Saponins

● Used as a defense mechanism against predators.

● They have similar properties to soap from which their name is derived
(from Latin: sapo, soap).
● Thus, saponins tend to induce the formation of emulsions between water
and organic solvents.

In experiment

● The tea leaves are soaked in an aqueous solution of sodium carbonate to

hydrolyze the tannins.
● The hydrolyzed tannins will dissolve in the aqueous layer.
● The components of the mixture are then separated through filtration.
● Caffeine, hydrolyzed tannins, residual pigments, small amounts of
glucose, free amino acids, some proteins, and saponins go to the aqueous
filtrate.
● The residue is left with cellulose and the nonhydrolyzed tannins.
● Caffeine is then isolated from the other components in the aqueous layer
based on the difference in polarity among the various components.
● Caffeine will prefer to be isolated in the organic layer rather than the
aqueous layer.
 ● On the other hand, glucose, amino acids, proteins, and gallic acid salts are
insoluble in organic solvents.
● The only obstacle is in the ability of the pigments, such as chlorophyll, to
partition between the organic and aqueous layers.
○ However, since they are only present in small amounts, they can be
eliminated at a later stage during the purification of caffeine.
● The product is then identified through thin-layer chromatography (TLC).

Chromatography

Origin

● Comes from the Greek words chroma meaning "color" and graphein
meaning "to write."
● Mikhail Tswett - Creator of the technique
○ Wanted to separate various plant pigments
1. Prepared a solution containing the pigments
2. Ran down through a glass column closely packed with finely
divided calcium carbonate.
● Separated compounds = colored bands on the column
○ Stationary phase: calcium carbonate column
○ Mobile phase: solvent used in his pigment solution

Today

● Components are separated

○ carried through a stationary phase by a liquid or gaseous mobile
phase.
● Component Separation Rate
○ depend on properties (polarity, size, etc.) of:
■ stationary phase
■ mobile phase
■ species to be separated
Polar stationary phase

● most polar = easily retained in the stationary phase

● most nonpolar = can still travel through the stationary phase.

Kinds of chromatography

● Column chromatography
○ Tswett’s method
● Gas chromatography (GC)
● High-performance liquid chromatography (HPLC)
● Thin-layer chromatography (TLC)
● Paper chromatography

Thin Layer Chromatography

Purpose

● Not only for separating

● Investigate purity of sample
● Decide solvent system best for column chromatography
● Determine the number of components present in the mixture
● Adsorption technique

Components

● Adsorbent - stationary phase

○ Most common: Finely ground silica (Si02•nH20) [AKA silica gel]
■ Relatively polar
● EN (O-S): 3.5-1.8 = 1.7 (Polar)
○ TLC Plates
■ Made through binding a certain adsorbent to a glass plate
● Developer - mobile phase
○ move the sample across the adsorbent layer
○ Too polar = all components about the same distance
 ■ Poor separation
○ Too nonpolar = NOT all components across the adsorbent.
○ Must be polar: nonpolar
● Sample

Binding Forces

● Some molecular interactions are stronger than others.

● When the mobile phase and the sample come into contact with the
adsorbent, several molecular interactions between the three components
may arise.
● Some molecular interactions might end up having the same binding
strength.
● Binding strengths: ion-dipole > dipole-dipole (H-bonds) > dipole-dipole
(others) > dipole-induced dipole > van der Waals
● More bulky groups tend to have stronger binding
○ Especially for compounds with similar molecular interactions with
the adsorbent
○ A larger surface area allows more possibility of molecular
interactions with the adsorbent

Adsorb and Desorb

● When the developer carries components across the TLC plate, some are
adsorbed by the adsorbent.
● As the developer passes over these components, it competes with the
adsorbent to desorb the components back to itself.
● The sites in which the components were adsorbed are then occupied by
some developer molecules to prevent readsorption of the components to
that site. However, the components can be adsorbed at a new site as it
moves along the TLC plate and again desorbed by the developer.
● If the component is more tightly bound to the adsorbent, then it spends
more time in the adsorbent than in the developer.
● The distance traveled by the component would be shorter.
 ● The same goes otherwise. If the component is a more tightly bound
developer, it spends less time in the adsorbent and is carried at a longer
distance.
● Stronger the binding forces, shorter distance traveled.
● There must be a very large adsorbent area to sample size ratio
○ Involves many readsorptions of components
● Large amount of sample
● contain great amounts of solute (components).
● TLC Plate size:
○ Readsorptions of many solutes = very large TLC plate.
○ For small plates = usually less than a milligram sample
○ TLC is NOT a preparative technique

Absorption vs. Adsorption

● Adsorption
○ Adherence/binding of a substance to a surface (a surface
phenomenon).
● Absorption
○ Passage of molecules into the interior of another substance
○ Cotton takes in water making it heavier than usual.
■ The water is absorbed by the cotton, which is the absorbent.

Ratio to Front, Rf

● Rf
○ Distance traveled relative to the Distance traveled by solvent at a
given time.
○ Component Rf is dependent on:
■ Structure
■ Polarity
■ Size
○ TLC is a good technique for identifying compounds because of the
qualities checked.
 ○ Rf is dependent on:
■ Adsorbent layer thickness
■ Type of developer

● Reference spots of known samples can be spotted on the same TLC plate
along with the mixture spot

○ Instead of comparing experimental Rf values to literature values

Spotting Techniques

1. Dip the micropipettes (or capillary tubes) in the sample

2. Lightly touch capillary tubes/micropipettes to a marked surface on the TLC
plate.
● The spot must be no > 2 mm in diameter
● Practice TLC spotting before sample spotting
● Spotting must not be TOO HARD as if punching a microscopic hole
● Press too hard = too concentrated
○ it will run as a smear or streak
● Press too little = not concentrated enough
○ nothing on the plate
Plate Development

● Sample carried through the adsorbent by the developer

● The most common way of Plate Development:
○ Spot the sample near the edge of the plate using a micropipette
■ The solvent is allowed to dry
○ TLC plate is placed in the developing chamber.
■ Developing chamber
● Covered container with a little amount of the developer
● The developer must be deep enough to touch and wet
the tip of the plate but shallow enough not to directly
touch the sample spot on that plate.
● Care must be taken in dipping the edge of the plate in
the developer.
● All the surface of the edge must simultaneously touch
the developer as the plate is being lowered down.
● The developing chamber must not be moved after the
TLC
○ Plate is placed inside to ensure the solvent front travels uniformly
up the plate
■ When the plate enters the solvent at an angle, it causes a slanted
solvent front line. This can affect separation quality.
■ If the plate were not placed inside, the solvent front might move
unevenly, leading to poor separation and misalignment of spots.

Visualization

● Several methods are employed to locate the components after separation.

● A common method (Usually for organic components)
○ Spray the TLC plate with a solution of iodine or sulfuric acid.
■ Organic components react with the sprayed solution
● Appear as dark spots on the plate
● Non-destructive method
 ○ Place the TLC plate (incorporated with a fluorescent material) under
UV light
■ Nonfluorescent components = dark spots under the UV light

Solubility Tests

Qualitative Organic Analysis

● Also known as wet analysis

● the most traditional way of identifying compounds

Solubility in Water

● Soluble in water
○ most probably contains four carbons, or less, and a nitrogen or
oxygen atom
○ The resulting solution is then tested with NaHCO3, a base.
■ Carboxylic acid: Bubbling or solubility
● Insoluble in water,
○ Necessary to go on to the next solubility test.

Solubility in 5% NaOH

● Alkaline test solution (5% NaOH) reacts with acidic compounds to form
water-soluble products
● Soluble to 5% NaOH but insoluble in water
○ Acidic (either a phenol ArOH or a carboxylic acid RCOOH)
■ To distinguish, test the compound’s solubility in NaHCO3.
● Insoluble in 5% NaOH
○ Proceed to test its solubility in 5% HCl.

Solubility in 5% NaHCO3

● As base: NaHCO3 < NaOH

● Sodium bicarbonate
○ usual ingredient of some over-the-counter antacids
 ● Phenols VS carboxylic acids
○ Bicarbonate ions react with carboxylic acids but not with phenols to
produce water-soluble salts.
○ The reaction also yields carbon dioxide, as evidenced by the
formation of bubbles.

Solubility in 5% HCl

● Soluble
○ Basic organic compounds, such as amines, react with the acid to give
water-soluble products.
● Insoluble
○ Test sulfuric acid solubility.

Solubility in Concentrated H2SO4

● Soluble
○ Unsaturated hydrocarbons and N- or O-containing compounds
■ protonated by this extremely powerful acid
■ products dissolve in the acid
● Insoluble
○ Compounds that contain only alkyl groups (RH), halogen atoms
(RX), and benzene rings (ArH, ArX)

Tests for Functional Groups

Ignition Test

● To distinguish aliphatic compounds (alkene/alkane) from aromatics

(hydrocarbons) by observing the flame and the smoke.
● Highly unsaturated compounds: a yellow flame with sooty smoke while
straight-chain compounds: a yellow flame with non-sooty smoke.

Baeyer Test

● Determine the presence of an alkene

 ○ treating the alkene with potassium permanganate at room
temperature to give a vicinal diol
● Positive
○ reddish-brown precipitate, in contrast to the purple color of
potassium permanganate

Lucas Test

● SN1 reaction
● Only applicable to alcohols up to 5- 6 carbons only
● Lucas reagent: zinc chloride dissolved in HCl.
● Reactions
○ React fastest: Tertiary alcohols
○ Take more time: Secondary and allylic alcohols
○ Not react at room temperature: primary alcohols
● Positive
○ formation of a second phase.

Chromic Acid Test

● Not react: Tertiary alcohols

● At room temperature: chromic acid oxidizes
○ primary alcohols into aldehydes
○ secondary alcohols into ketones
● Also react: Aldehyde
○ can be readily oxidized into carboxylic acids.
● Positive
○ formation of a green precipitate (Cr3+).

Hydroxamic Acid Test

● Produce hydroxamic acid

○ esters react with hydroxylamine (NH2OH) under an alkaline
environment
● Acid then complexes with iron (III) chloride
 ○ form a red-violet octahedral complex under an acidic medium

Iodoform Test

● Characterization test for methyl ketones, ethanol, and methyl carbinols

(alkylmethylmethanols)
● Positive: Yellow precipitate of iodoform (CHI3)

2,4-Dinitrophenylhydrazine Test

● React immediately: Aldehydes and ketones

○ yellow to red precipitates (2,4-dinitrophenylhydrazones)
○ The more intense the red color = the more conjugation is present in
the sample.
● Since 2,4-DNPH is red-orange
○ precipitates can be washed to see the true color.
● The reagent can also oxidize allylic and benzylic alcohols
○ produce small amounts of precipitate.
● Positive: the presence of a considerable amount of precipitate.
○ Very small yields are ignored.`

Tollens’ Test

● To distinguish an aldehyde from a ketone

● Tollens’ reagent: a solution of silver ion in ammonia
● Aldehyde is made to react with the reagent
○ give a carboxylic acid and a silver mirror
● Otherwise, a black precipitate of Ag2O will just be observed.
● Ketones do not produce metallic silver.
● How to produce the silver mirror
○ make sure that the test tube being used is clean and grease-free
Soap Chemistry

Soap

● Metal salts of fatty acids

● Purpose
○ As surfactants for washing, bathing, or cleaning
○ In lubricants as a thickening agent

Common Soap

● Sodium salts of medium to long chain fatty acids containing 12 to 18

carbon atoms.
○ Fatty acids obtained from triglycerides, esters of fatty acids, and
glycerol
■ Triglycerides - a principal constituent of animal/vegetable fats
and oils.

Saponification

● Reaction of triglycerides with a strong base

● Base-promoted hydrolysis of triglycerides to form soap and glycerol

Soap and Base

● The type of base used determines the kind of soap formed

○ Sodium soaps (from NaOH) = firm
○ Potassium soaps (from KOH) = softer, more fluid
○ Lithium and calcium soaps = hard
■ often found in greases

Soap Surface Tension

● Hydrophilic, charged carboxylate head

○ highly soluble in water
 ● Hydrophobic hydrocarbon tail
○ highly soluble in fats, oils, or grease
● Reaction
1. In water, the hydrophobic tails buckle together leaving the
hydrophilic heads on the outside to form water-soluble micelles
2. Fats, oils, or grease, which are insoluble in water, become
encapsulated in the hydrophobic pocket of the micelles
● Shields them from water molecules
3. The entire micelle is washed away with water.

Soap Cleaning Power

● Depends on the length of the fatty acid

○ < 10 carbon atoms = soaps with no detergent action
○ > 18 carbon atoms = insoluble soaps even in hot water
○ 10-18 carbon atoms = preferred for soaps

SAP Chart

● Fatty acid composition of fats and oils changes depending on the

conditions where:
○ the plant was grown or the animal was raised
○ on the source itself
● amount of base needed to completely saponify fats and oils varies
depending on its source
● Determined experimentally through SAP chart
● SAP value
○ amount of KOH (in mg) needed to completely saponify 1 g of fat/oil
● Convert SAP value to mg NaOH when using sodium hydroxide
○ multiply the ratio of the molecular weights of NaOH and KOH
(0.71289).
Soap Making

Three Variations

● Cold process, hot process, or fully-boiled process

● Cold and hot process
○ requires the exact amounts of fats/oils and base
■ prevent the finished product from containing excess amounts
of base or fat/oil
● Fully-boiled process
○ requires the use of an excess amount of base

Cold Process

1. Fat/oil (liquefied with heating)

2. Base (dissolved in water)
3. Fat and Base are combined until the two phases are completely emulsified.
● TAMA: Mixture begins to trace
○ The mixture thickens into a batter-like consistency
4. If some of the mixture is drizzled on the surface, it leaves behind a trail
that takes a while to sink back into the mixture.
● It is at this point where additives, such as fragrance and solid
additives may be added.
5. The mixture is poured into molds where saponification will continue for 12
to 48 hours.
6. The soap is removed and allowed to cure for 2-6 weeks on a drying rack
before use.
● Trace amounts of the base are consumed by saponification or
neutralized with carbon dioxide in the air.
● The soap hardens as the excess water evaporates.

Hot Process

● The mixture is heated = Saponification is completed

 ○ Before the mixture is poured into molds
● Discount by 2-5% to retain a slight excess of fat/oil for a gentler soap (too
much leaves the soap greasy)
● Glycerol byproduct of saponification remains in the soap and acts as a
moisturizing agent

Fully-Boiled Process

● Mixture boil until saponification is completed

● Soap is precipitated from the rest of the mixture with the addition of salt
○ Impurities in the fat/oil, excess lye, and glycerol are removed to
leave a purer, whiter soap
● Soap is then dried
○ additives such as fragrance, color, emollients (moisturizers),
exfoliants, and other additives are added before the soap is extruded,
cut, and then stamped into its final shape