EXPERIMENT : SOAP MAKING (SAPONIFICATION)

In this experiment we prepare soap from animal fat (lard) or vegetable oil. Animal fats and
vegetable oils are esters of carboxylic acids; they have a high molecular weight and contain the
alcohol, glycerol. Chemically, these fats and oils are called triglycerides (See chapter 27.3 of
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soap by adding an essential oil. You can purchase the scent you want to add or isolate it from
the natural source using a process of steam distillation (see ‘Natural Product Isolation’ procedure
at the end of this lab)

O
- +
R 1C O CH 2 R 1CO O Na HO CH 2

O
NaOH
R 2C O CH R 2CO O- Na + + H O CH 2
saponification
or
hydrolysis
O
- +
R 3C O CH 2
R 3CO O Na HO CH 2

Triglycerides Carboxylic Glycerol

(Fat or Oil) acid salts
(Soap)

The natural acids are rarely of a single type in any given fat or oil. In fact, a single
triglyceride molecule in a fat may contain three different acid residues (R1COOH, R2COOH,
R3COOH), and not every triglyceride in the substance will be identical. Each fat or oil,
however, has a characteristic statistical distribution of the various types of acids possible—See
chapter 26.3, pg 1121 of Bruice for some examples.
The fats and oils that are most common in soap preparations are lard and tallow from animal
sources, and coconut, palm, and olive oils from vegetable sources. The length of hydrocarbon
chain and the number of double bonds in the carboxylic acid portion of the fat or oil determine
the properties of the resulting soap. For example, a salt of a saturated long-chain acid makes a
harder, more insoluble soap. Chain length also affects solubility.
Tallow is the principal fatty material used in making soap. The solid fats of cattle are melted
with steam, and the tallow layer formed at the top is removed. Soapmakers usually blend tallow
with coconut oil and saponify this mixture. The resulting soap contains mainly the salts of
palmitic, stearic, and oleic acids from the tallow, and the salts of lauric and myristic acids from
the coconut oil. The coconut oil is added to produce a softer, more soluble soap. Lard (from
hogs) differs from tallow (from cattle or sheep) in that lard contains more oleic acid.
 Tallow CH 3(CH 2)14CO OH CH 3(CH 2)16CO OH
Palmitic acid Stearic acid
CH 3(CH 2)7CH CH(CH 2)7CO OH
Oleic acid
Coconut oil CH 3(CH 2)10CO OH CH 3(CH 2)12CO OH
Lauric acid Myristic acid

Pure coconut oil yields a soap that is very soluble in water. The soap contains essentially the
salt of lauric acid with some myristic acid. It is so soft (soluble) that it will lather even in
seawater. Palm oil contains mainly two acids, palmitic acid and oleic acid, in about equal
amounts. Saponification of this oil yields a soap that is an important constituent of toilet soaps.
Olive oil contains mainly oleic acid. It is used to prepare Castile soap, named after the region in
Spain in which it was first made.
Toilet soaps generally have been carefully washed free of any alkali remaining from the
saponification. As much glycerol as possible is usually left in the soap, and perfumes and
medicinal agents are sometimes added. Floating soaps are produced by blowing air into the soap
as it solidifies. Soft soaps are made by using potassium hydroxide, yielding potassium salts
rather than the sodium salts of the acids. They are used in shaving cream and liquid soaps.
Scouring soaps have abrasives added, such as fine sand or pumice.

To Prepare for this lab: Read section 17.14 of Bruice for a review of Soaps.

Prelab to be turned into your instructor before you begin:

1)Write the balance equation for this reaction (use a C18 triaceylglyceride for you ‘oil’)

2) State what oil (or mixture of oils) that you will be using to make your soap. Use 100g of total
oil. Also be sure to have calculated the amount of sodium hydroxide and water that you will be
using (see procedure below for an explanation).

Think about what mold you may want to use --the bottom of quart size milk carton is pre lined
and works great and bring one if you can.

The soap making procedure and advice below was graciously produced by Sean Choi, an
exceptional soap maker. A recommended soap making website that you can refer to is
‘Thesage.com’. This website will also give you ideas as to what oils to use and scents (essential
oils) that can be added. Note that you can add an essential oil to scent your soap.

Many oil will be provided (olive oil, Veg oil and a few others) but you are encouraged to
purchase/bring some from home to produce you own unique soap.

You can also purchase soap molds and essential oil at Zenith supply on 63rd and Roosevelt.
http://www.zenithsupplies.com/
SOAP MAKING ADVICE AND PROCEDURE:

Introduction: The reaction in making soap (saponification) is a base (usually

NaOH or KOH) hydrolysis of triglycerides to make three salts (soap) and glycerol.
The molecules crystallize differently depending on the base used. NaOH
produces a harder bar while KOH is used more frequently for liquid soaps.

The two most commonly used methods to make soap at home are called the cold
process and the hot process. Both require a heat source and careful calculations
to ensure that no caustic base is left unreacted in the soap. The hot process
uses heat to speed the reaction resulting in fully saponified soap by the time you
pour your soap into molds. The cold process uses just enough heat to ensure
that all the fat is melted prior to reacting it with the base. I prefer the cold
process because it is simpler, requires less time and energy, while resulting in a
creamier bar. We will use the cold process in this experiment.

In this experiment you must calculate the amount of base required to make a
soap using a specific oil.

To calculate the amount of NaOH required, you must refer to the table at the end
of this experiment. The figures in the third column (NaOH – Bar Soap) give the
grams of base required to saponify 1 gram of the oil. For example, 1.0 gram of
avocado would require 0.133 g of solid NaOH. In this experiment, you will use a
5 % excess of the oil to ensure that nearly all of the sodium hydroxide is
consumed in the saponification process. Otherwise, the soap will be too basic
and could be harmful to use. If 100 g of avocado oil were used, then the amount
of NaOH required (assuming a 5% excess of oil) would be 95 g oil x 0.133 g
NaOH/1.0 g oil = 12.63 g of solid NaOH. Water is also required for this soap.
For most soaps, a good amount of water is 35% of the mass of oil used. In this
case, the amount of water required would be 35 g ( or 35 mL).

It is sometimes desirable to use more than one kind of oil. Here are the
calculations for a soap containing 30% coconut oil and 70% olive oil. Assume
that 70 g of coconut oil and 30 g of olive oil are used. First, calculate the mass of
95% of each oil to ensure that there is a 5% excess of oil. Then do the following
calculation:
28.5 g coconut oil x 0.181 g NaOH/g oil + 66.5 g olive oil x 0.134 g NaOH/g oil
= 5.16 g + 8.91 g = 14.07 g NaOH required.

The recipe would be 30 g of coconut oil, 70 g of olive oil, 14.06 g NaOH, and 35
mL of water.

Note: A great all around soap is made with 30% coconut oil, 35% Crisco
shortening, and 35% olive oil. Not too dry and good cleaning.

PROCEDURE

1. Determine how much soap you want to make. In this experiment, you should
use 100 g of oil, either 100% of one oil or a mixture.

2. Decide which oil/oils you will be using. Each oil has differing properties that
react differently and produce different qualities in your soap. For example,
coconut oil will give you a hard bubbly bar with excellent cleaning properties,
however, bars with more than 40% coconut oil can be drying to the skin. On
the other hand, olive oil makes a super moisturizing soap but the bar is softer,
doesn’t last as long, and can leave behind an oily feeling. 100% olive oil bars
also take considerably longer to react. In general, oils that are great for
cleaning produce a harder bar but aren’t that moisturizing, while moisturizing
oils produce softer bars and don’t clean as well. 30% coconut oil and 70%
other oil/oil blend reacts easily and makes a great all around bar.

3. Each oil requires a different amount of base to react completely and can be
looked up in a saponification table (attached). Calculate the amount of NaOH
required to react all but 5 % of your oil(s). You want a 5% excess of oil in your
soap to ensure that no caustic base remains unreacted in your soap. The
excess oil is also great for the skin.

4. Prepare your mold, anything that will hold its shape will do. You will want to
either grease your mold with petroleum jelly or line with freezer paper,
parchment paper, or plastic wrap. DO NOT use aluminum foil because it will
react with your base and release hydrogen gas. The bottom of quart size milk
carton is pre lined and works great.

5. Make your aqueous base solution. Weigh out the amount of NaOH calculated
in step 3 and put aside. Then pour 35.0 mL of distilled water into a 250-mL
beaker. Slowly add the base to the water (never water to base!) while stirring
with a glass stirring rod until dissolved and let cool to 33-43°C.

Caution: NaOH is caustic and can burn you! Wear gloves! When NaOH
is dissolved in water, a lot of heat is given off. This solution may become
very hot.
6. Weigh and place oils into a beaker and melt/heat on a hot plate to 33-43°C.
Mixing the oils and base at similar temperatures facilitates the reaction and
prevents separation.

7. Once both the base solution and your oils are 33-43°C, you can begin slowly
pouring the aqueous base solution into the oils while stirring. A magnetic stir
bar may facilitate this process. Continue stirring until the mixture begins to
thicken and you can see trails of your mixture on the surface upon lifting your
spoon/stirrer above the surface. This stage is called ‘trace’ and some oils take
longer than others to reach this stage. Once you have reached ‘trace’, you
can add any fragrances or additives, mix thoroughly, then pour into your mold.
Be mindful not to pour your stir bar into the mold. If you do, wear gloves when
fishing it out and change gloves afterwards.

(A helpful hint for cleaning the beaker is to let it sit until next lab period. By that
time, the glass will be lined with soap rather than an oily caustic film. This is one
of the few times in life where it pays off to put it off!)

8. Optionally you can insulate your mold with towels to trap heat and facilitate
the reaction, or not. Some prefer to even chill the mixture at this point to
prevent the soap from going through a ‘gel’ stage which occurs when the
reaction heats up, turning the soap transparent for a short time before turning
opaque again. The soap will appear different having gone through, or not
having gone through ‘gel’ stage. Either way, your soap should be nearly
completely saponified in 24-48 hours, at which point it can be removed from
the mold. Though safe to use at this point, curing for 4-6 weeks will react any
trace amounts of base and evaporate excess water, resulting in a smoother
and longer lasting bar.

9. Before using your soap, you must test the pH to make sure that it is not too
basic. You will test the pH in three different ways. Using a sharp device such
as a knife or scalpel, shave off about 1 g of your soap in small pieces. Add to
20 mL of water in a small beaker and stir. Transfer about 2 mL of this mixture
to a test tube and add a couple drops of phenolphthalein. The test range for
phenolphthalein is ~ pH 8-10, changing from colorless to a deep pink.
Colorless to light pink is fine. The more intense the pink, the more basic it is.
A soap that gives a deep pink color may be an indication of an erroneous
measurement or non-uniform mixture. A soap giving a deep pink color
could be dangerous. Verify the pH using a pH meter. Soaps with a pH > 10
can be irritating to the skin depending on skin type. Soaps with a pH >
11 should NOT be used on the skin. They can be grated and used as
laundry soap which generally has a pH of 10-12. Finally test a couple drops of
the soap solution on pH paper to see if you get similar results.
 For the saponifcation table below simply find you oil that you are using, and multiply the
grams that you will use of that oil times the value given under the base you are using (in
this case sodium hydroxide). This product of this value is the weight of base (in grams)
that you need (see sample calculation above).

Oil SAP NaOH KOH INCI Name

Sodium Potassium

Hydroxide Hydroxide

(Bar Soap) (Liquid

Soap)

Almond Butter, 90 - 140 0.098 0.139 Prunus amygdalus dulcis (Sweet Almond) Oil
Sweet

Almond Oil 190 - 200 0.137 0.194 Prunus amygdalus dulcis (Sweet Almond) Oil
Sweet

Almond Oil, 190 - 200 0.137 0.193 Prunus amygdalus dulcis (Sweet Almond) Oil
Sweet, Organic

Aloe Butter 220 - 260 0.176 0.247 Cocos Nucifera (Coconut) Oil and Aloe
Barbadensis Leaf Extract

Aloe Vera Oil 185 - 200 0.135 0.191

Apricot Kernel 130 - 145 0.097 0.1361 Prunus armeniacae (Apricot) Kernel Oil
Butter

Apricot Kernel Oil 185 - 195 0.135 0.190 Prunus armeniaca (Apricot) Kernel Oil

Apricot Kernel 185 - 195 0.135 0.190 Prunus armeniaca (Apricot) Kernel Oil
Oil, Organic
Avocado Butter 177 - 198 0.132 0.186 Hydrogenated Persea gratissima (Avocado)
Seed Oil

Avocado Oil 177 - 198 0.133 0.188 Persea gratissima (Avocado) Oil

Babassu Oil 245-256 0.178 0.251 Orbignya oleifera (Babassu) Seed Oil

Baobab Oil 190 - 220 0.143 0.202 Adansonia digitata (Baobab) Seed Oil

Beef Tallow 190 - 200 0.140 0.196

Beeswax White 89 - 103 0.067 0.095 Beeswax

Beeswax, yellow 89 - 103 0.067 0.095 Beeswax

Blackcurrant Oil 185 - 195 0.134 0.188 Ribes nigrum (Blackcurrant) Fruit Oil

Borage Oil 175 - 196 0.134 0.189 Borago officinalis (Borage) Seed Oil

Brazil Nut Oil 245-256 0.176 0.247

Camellia Oil 185 - 197 0.134 0.189 Camellia oleifera (Camellia) Seed Oil

Candelilla Oil 43 - 65 0.038 0.053

Canola Oil 0.132 0.187

Castor Oil 175 - 187 0.127 0.179 Ricinus communis (Castor) Seed Oil
Cherry Kernel Oil 182-202 0.138 0.194 Prunus avium (Cherry) Kernel Oil

Cocoa Butter 188 - 200 0.136 0.192 Theobroma cacao (Cocoa) Seed Butter
(deodorized) Deodorized

Cocoa Butter 188 - 200 0.136 0.192 Theobroma cacao (Cocoa) Seed Butter
(food grade)

Cocoa Oil 173-188 0.127 0.179 Theobroma cacao (Cocoa) Oil

Coconut Oil 76 250 - 264 0.181 0.256 Cocos nucifera (Coconut) Oil

Coconut Oil, 250 - 264 0.178 0.252 Cocos Nucifera (Coconut) Oil
Organic

Cod Liver Oil 0.132 0.1848

Coffee Seed Oil 0.130 0.182

Corn Oil 0.135 0.190

Cottonseed Oil 0.137 0.192

Emu Oil (Fully 185 - 200 0.135 0.191 Emu Oil

Refined)

Evening 175 - 196 0.133 0.188 Oenothera biennis (Evening Primrose) Oil
Primrose Oil

Evening 175 - 196 0.133 0.188 Oenothera biennis (Evening Primrose) Oil
Primrose Oil,
Organic
Flax Seed Oil 188 - 196 0.135 0.190 Linum usitatissimum (Linseed) Seed Oil

Flax Seed Oil, 188 - 196 0.135 0.190 Linum usitatissimum (Linseed) Seed Oil
Organic

Fractionated 325 - 340 0.237 0.334 Caprylic/Capric Triglyceride

Coconut Oil

Grape Seed Oil 185 - 200 0.134 0.187 Vitis vinifera (Grape) Seed Oil

Hazelnut Oil 180 - 200 0.136 0.192 Corylus americana (Hazel) Seed Oil

Hemp Seed 175 - 200 0.133 0.1875 Cannabis sativa Seed Oil (and) Hydrogenated
Butter Vegetable Oil

Hemp Seed Oil 190 - 195 0.137 0.193 Cannabis sativa (Hemp) Seed Oil

Hemp Seed Oil, 190 - 195 0.135 0.191 Cannabis sativa (Hemp) Seed Oil
Organic

Illipe Butter 188 - 200 0.136 0.192 Shorea stenoptera (Illipe) Seed Butter

Jojoba Golden 91 - 93 0.068 0.096 Simmondsia chinensis (Jojoba) Seed Oil

Jojoba, Organic 91 - 93 0.068 0.096 Simmondsia chinensis (Jojoba) Seed Oil

Kokum Butter 187 - 193 0.134 0.188 Garcinia indica (Kokum) Seed Butter

Kukui Nut Oil 190 - 195 0.135 0.191 Aleurites moluccana (Kukui) Nut Oil

Lard 0.141 0.199

Lavender Butter 175 - 200 0.133 0.1875 Prunus Amygdalus Dulcis (Sweet Almond) Oil
(and) Lavendula angustifloia extract, (and)
Hydrogenated Vegetable Oil

Macadamia Nut 175 - 200 0.133 0.1875 Macadamia ternifolia Seed Oil (and)
Butter Hydrogenated Vegetable Oil

Macadamia Nut 190 - 200 0.138 0.195 Macadamia (Macadamia ternifolia) Seed Oil
Oil

Mango Butter 183 - 198 0.135 0.190 Mangifera indica (Mango) Seed Butter

Marula Oil 188 - 196 0.135 0.190 Sclerocarya birrea (Marula) Kernel Oil

Meadowform Oil 169 0.120 0.169 Limnanthes alba (Meadowfoam) Seed Oil

Moringa Oil 193.2 0.136 0.191 Moringa (Moringa oleifera) Oil

Neem Oil 175 - 205 0.138 0.194 Azadirachtin indica (Neem) Oil

Olive Butter 175 - 200 0.138 0.193 Olea Europaea (Olive) Fruit Oil (and)
Hydrogenated Vegetable Oil

Olive Oil A 184 - 196 0.134 0.190 Olea europaea (Olive) Fruit Oil

Olive Oil, Extra 184 - 196 0.135 0.190 Olea europaea (Olive) Fruit Oil
Virgin

Olive Squalane, 184 - 196 0.135 0.190

Refined
Organic 184 - 191 0.133 0.1875 Rubus Idaeus (Red Raspberry) Seed Oil
Raspberry Seed
Oil

Palm Butter 0.155 0.218

Palm Kernel Oil 220 0.155 0.218 Elaeis guineensis (Palm) Kernel Oil

Palm Oil 190 - 205 0.144 0.203 Elaeis guineensis (Palm) Oil

Palm Oil, 190 - 205 0.144 0.203 Elaeis guineensis (Palm) Oil
Organic

Peanut Oil 0.136 0.190

Perilla Oil 185 - 200 0.135 0.191 Perilla ocymoides (Perilla) Seed Oil

Pistachio Nut 175 - 200 Pistacia Vera Seed Oil (and) Hydrogenated
Butter Vegetable Oil

Pomace Olive Oil 0.133 0.188 Olea europaea (Olive) Fruit Oil

Poppyseed Oil 0.137 0.194

Pumpkin Seed 187 - 195 0.132 0.186 Cucurbita pepo (Pumpkin) Seed Oil
Oil

Rapeseed 182 - 193 0.124 0.175

(Canola) Oil

Rice Bran Oil 180 - 190 0.131 0.185 Oryza sativa (Rice) Bran Oil
Rosehip Oil 185 - 193 0.133 0.187 Rosa canina (Rosehip) Fruit Oil

Safflower Oil, 185 - 198 0.135 0.190 Carthamus tinctorius (Safflower) Seed Oil
High Linoleic

Sal Butter 178 - 192 0.130 0.183

Seabuckthorn Oil 130 - 200 0.116 0.163 Hippophae rhamnoides (Seabuckthorn) Oil

Sesame Oil 186-199 0.135 0.191 Sesamum indicum (Sesame) Seed Oil

Shea Butter 170 - 185 0.126 0.178 Butyrospermum parkii (Shea Butter) Fruit

Shea Butter Ultra 160 - 180 0.131 0.185 Butyrospermum parkii (Shea Butter) Fruit)

Shortening 0.136 0.192

(vegetable)/Tallo
w

Soybean Oil 190 0.134 0.188 Glycine soja (Soybean) Oil

Sunflower Seed 185 - 198 0.136 0.191 Helianthus annuus (Sunflower) Seed Oil
Oil

Turkey Red Oil 0.127 0.178 Sulfated Ricinus communis (Castor) Oil

Virgin Coconut 250 - 264 0.178 0.252 Cocos nucifera (Virgin Coconut) Oil
Oil

Walnut Oil 190 - 197 0.136 0.192 Juglans regia (Walnut) Seed Oil
Wheat Germ Oil 180 - 200 0.132 0.186 Triticum vilgare (Wheat) Germ Oil