Soap Making

A 20-mule team hauling borax out of the valley. Photo provided by the National Park Service.

Borax (Na2B4O7 _10H2O), the most widespread borate mineral was found to
help remove dirt from people and cloth. Borax is crumbly and powdery, and
dissolves easily in water. Borax became an alternative to the very harsh soap
which was used prior to the discovery of borax in the late 1800's. This light and
easy to use substance was hailed the world over as a washing, cleansing,
antiseptic, preservative, and medicine miracle.
In the 1880s, large borate deposits were discovered in Death Valley,
California. However, the Death Valley borate deposits were located almost 170
miles from the nearest railway. In order to get the borate to the railway
economically, the owners of the Death Valley mines used large wagons pulled
by teams of 20 mules. The detergents made from this borate were thus sold
as "20 Mule Team Borax".
A 20 mule team hauling borax in Death Valley

Saponification
Process of making soap from animal fat or vegetable oil using a base.
O
CH2 O C (CH2)14CH3

CH2 OH
O

O
CH O C (CH2)14CH3

+ 3 NaOH

CH OH + 3 Na+ -OC (CH2)14CH3

O
CH2 O C (CH2)14CH3
glyceryl tripalmitate
(tripalmitin)

CH2 OH
sodium
hydroxide

glycerol

3 sodium palmitate
(soap)

A Phospholipid
polar head

nonpolar tails

(a) chemical structure of a phospholipid

polar head

nonpolar tails

(b) simplified way to draw a phospholipid

Timberlake, Chemistry 7th Edition, page 576

A Model of a Cell Membrane

Polar
Nonpolar

Cholesterol

Timberlake, Chemistry 7th Edition, page 587

Proteins

Phospholipid
bilayer

Formation of a Triglyceride

Stearic Acid
Fatty acid
Carboxylic acid group

Soap

COO- bonds to a metal ion (Na+)

Na+
H+ lost from

Kelter, Carr, Scott, Chemistry A Wolrd of Choices 1999, page 257

COOH

Copyright 2007 Pearson Benjamin Cummings. All rights reserved.

Sodium
stearate:
a soap

Sodium
dodecyl
sulfate:
a detergent

Copyright 2007 Pearson Benjamin Cummings. All rights reserved.

Cleaning Action
of Soap
Micelle

Timberlake, Chemistry 7th Edition, page 573

Micelle

Copyright 2007 Pearson Benjamin Cummings. All rights reserved.

micelle

Copyright 2007 Pearson Benjamin Cummings. All rights reserved.

SOAP
-- made from animal and
vegetable fats
water

vs.

DETERGENT
-- made from petroleum
-- works better in hard

Hard water contains minerals w/ions like Ca2+, Mg2+, and Fe3+
that
replace Na1+ at polar end of soap molecule. Soap is changed
into
an insoluble precipitate (i.e., soap scum).

micelle: a liquid droplet covered

w
/soap or detergent molecules

Solvation
Like Dissolves Like
NONPOLAR

POLAR
NONPOLAR

POLAR

Solvation
Soap / Detergent

polar head with long nonpolar tail

dissolves nonpolar grease in polar water

micelle