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 O CH O C (CH2)14CH3 + 3 NaOH O CH2 O C (CH2)14CH3
glyceryl tripalmitate (tripalmitin) sodium hydroxide

CH2 OH
O CH OH + 3 Na+ -OC (CH2)14CH3 CH2 OH
glycerol
3 sodium palmitate (soap)

A Phospholipid
polar head

nonpolar tails

(a) chemical structure of a phospholipid

polar head
Timberlake, Chemistry 7th Edition, page 576

nonpolar tails

(b) simplified way to draw a phospholipid

A Model of a Cell Membrane

Polar Nonpolar

Cholesterol

Proteins

Phospholipid bilayer

Timberlake, Chemistry 7th Edition, page 587

Formation of a Triglyceride

Stearic Acid
Fatty acid Carboxylic acid group

Soap

COO- bonds to a metal ion (Na+) Na+ H+ lost from COOH

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

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

vs.

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

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