Preparation of a Detergent P. L. K. E., Experiments in Organic Chemistry. p.

357 - 361

Andrew Aspaas and Levi Stanley 5 January, 2000

Introduction: Detergents are synthetic cleaning compounds which work well in all types water, and are useful alternatives to soaps, which are derived from natural reactants and do not work well in hard water. However, detergents cannot be biodegraded by microbes in sewage treatment systems, thereby causing pollution in some water sources. Commercially, detergents are not sold as pure compounds. Rather, they contain several additives such as phosphate builders which help to keep hard water ions in solution. These present their own problems, however, as phosphate buiders can cause eutrophication in lakes and other bodies of water. Nevertheless, many detergents remain in common use due mostly to their low price and high effectiveness.

In this experiment, sodium lauryl sulfate, a detergent, was prepared from lauryl alcohol and chlorosulfonic acid. First, lauryl alcohol, in the presence of acetic acid, was added to chlorosulfonic acid to form the lauryl ester of sulfuric acid. Aqueous sodium carbonate was then added to form the sodium salt, or sodium lauryl sulfate. The product is then extracted with 1butanol.

Experimental: A 25 mL Erlenmeyer flask was cooled in an ice bath. A gas trap with 3 M sodium hydroxide was prepared. 0.300 mL glacial acetic acid was cooled in the flask for about 5 minutes. 0.105 mL chlorosulfonic acid was added dropwise to the flask. 0.36 mL dodecyl alcohol was added with a magnetic stirrer and the gas trap was attached. It was left to stir and react for 15 minutes.

A flask of deionized water was cooled on an ice bath. Water was added dropwise until the solution became a uniform consistency (about 60 drops). It continued to stir for a few minutes. Solution was not perfectly white, and was foamy. 0.90 mL 1-butanol was added, which liquefied the mixture further. It was stirred for five minutes. 0.45 g sodium carbonate was added and CO2 was observed bubbling off. It was transferred to a vial and allowed to seperate. The bottom aqueous layer was removed and re-extracted with more 1-butanol. The aqueous layer was discarded and the organic layers were combined. It was left to sit overnight in a drying cabinet to evaporate the

butanol.

After evaporation, we had a thick, slightly colored liquid. When mixed with water and shaken, the mixture foamed up about 2 mL and retained the foam for several minutes. When CaCl2 was added, the mixture foamed as before.

compound acetic acid chlorosulfonic acid lauryl alcohol 1-butanol sodium lauryl sulfate

MW 60.03 116.52 223.60 74.12 288.40

mass (g) 0.31 0.18 0.30 0.73 0.40

vol (mL) 0.30 0.10 0.36 0.90 -

d (g/mL) 1.05 1.75 0.83 0.81 -

mmol 5.24 1.58 1.34 9.83 1.37

percent yield =

1.37 mmol = 102.2% 1.34 mmol

Results and Discussion: As the product of this experiment, 0.40 g of sodium lauryl sulfate was isolated. This calculates to a 102.2% yield. This showed that there was some other impurity present in the final product that was adding extra mass. It is probable that there was still 1-butanol present in the product which did not get fully evaporated away. This was determined by methods of FTIR spectroscopy. The spectrum of the final product was not characteristic of pure sodium lauryl sulfate, as compared to the literature spectrum. However, when a spectrum of pure 1-butanol was subtracted from the original spectrum, a spectrum that more closely matched the reference was obtained. The large -OH stretch from 3300 - 3000 cm-1 was removed while the S=O stretch at approx 1700 cm-1 remained. Due to the thick consistency of our product, the spectra were run in a NUJOL mull. The NUJOL may account for some of the extra peaks in our spectrum that were not in the reference. Foaming tests also supported the conclusion that sodium lauryl sulfate was successfully synthesized. When mixed with water and shaken, a large amount of foam was produced. When calcium chloride, a common hard water solute, was added, the mixture foamed up just as much, which indicated that the final product was indeed a detergent, as a soap would not have foamed up in the presence of hard water minerals.