Ethylene glycol mono-stearate

Aim: To prepare ethylene glycol monostearate from stearic acid and ethylene glycol.

Apparatus: Four necked RBF, thermowell, thermometer, condenser, heating mantle, funnel,
beaker, N2 gas purger.

Reagents: Ethylene glycol, stearic acid, Para-toluene sulfonic acid, phenolphthalein, 0.5 N KOH
solution.

Theory: Glycol stearate or glycol monostearate or ethylene glycol monostearate is an ester of

stearic acid and ethylene glycol. It is a nonionic surfactant. Non-ionic surfactants are surface active
agents that don’t dissociate into ions in aqueous solution, unlike anionic surfactants which have a
negative charge, and cationic surfactants which have a positive charge in aqueous solution. Non-
ionic surfactants like ethylene glycol monostearate are widely used in detergents formulations as
anionic surfactants are insoluble in hard waters and cationic surfactants are considered to be poor
cleaners. In addition to detergency, ethylene glycol monostearate shows excellent solvency, low
foam properties and chemical stability. It is thought that non-ionic surfactants are mild on the skin
even on high loadings and long-term exposures. The hydrophilic group of the ethylene glycol
monostearate is the polymerized ethylene oxide group. Depending on the ratio and order of oxide
addition, the chemical and physical properties may vary.

The reaction of monoethylene glycol monostearate can be represented as:

O PTSA O
OH + HO O OH + H2O
OH
Stearic acidstearic acid Ethylene glycol Ethylene glycol monostearate Water

In the above reaction one mole of stearic acid reacts with one mole of ethylene glycol to give one
of monoethylene monostearate and one mole of water. A condenser can be attached to ease the
removal of evaporated water (as the reaction is carried out at 120 ℃. The accumulated water can
be observed to determine the extent of reaction. At the end of the reaction due to formation of
ester, the acid value of the reaction mixture should be as low as possible.
The applications of ethylene glycol monostearate include:

1. To give surfactant a pearlized look.

2. It is used in cosmetics and pharmaceuticals formulations.

3. It is used in the formulation of shampoo, liquid soaps and hand cleaners as pearling and
masking agent.

4. It is used as an opacifier liquid foam baths.

5. Emulsifying agent in moisturizers, sunscreens lotions.

6. It is used as an emollients and emulsion stabilizer.

Since EGMS has multifarious applications, different standards are used for different purposes like
cosmetics, pharmaceuticals and surfactants, etc. the BIS standards of EGMS for cosmetic field are:

Requirements
Sr.No. Specifications
Emulsifying Non-emulsifying
1 Appearance White flakes White flakes
2 Acid value (max.) 5 5
3 Monostearate content (min.) 35% 40%
4 Melting range 54-57 ℃ 54-60 ℃
Iodine value of separated fatty
5 3 3
acid (max.)
6 Saponification value 155 – 165 160 – 175
7 Sulfated ash 0.4 – 0.9% Max. 0.2%
8 Iron as Fe (Max.) 20 ppm 20 ppm
9 Water content (max.) 2% 2%
10 pH of 5% dispersion 8.5 – 10 4–7
As specified by the As specified by the
11 Free glycerine
buyer buyer
Procedure:
1. Arrange the proper reaction setup using 1 liter four neck flask, condenser, stirrer,
thermowell & N2 purger.

2. Charge stearic acid, ethylene glycol and para-toluene sulfonic acid.

3. Increase the temperature of the reaction mixture to 120 ℃ under inert atmosphere.

4. Continue the reaction maintaining the temperature at 120 ℃ and checking temperature
at 5 – 10-minute interval. Also checking the acid value at the interval of 2 hours till desired
acid value (< 20) is obtained.

5. Cool the reaction mass to 80 – 85 ℃ after achieving desired acid value. Pour the mass in
the way to get flakes.

6. Analyse the product for melting point (54 – 60 ℃), %free fatty acid and % free MEA = 2.5%
(max).

Result:

Sr. No. Specifications Requirements Results

1 Appearance White flakes
2 Acid value 5 (max.)
3 Saponification value 155 – 165
4 % moisture 2% (max.)
5 Melting Range 54-60 ℃
6 Iodine value 3 (max.)
Observations & calculations:
𝑊𝑊𝑊𝑊𝑊𝑊𝑊𝑊ℎ𝑡𝑡 𝑜𝑜𝑜𝑜 𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠 𝑎𝑎𝑎𝑎𝑎𝑎𝑎𝑎 =
𝑃𝑃𝑃𝑃𝑃𝑃𝑃𝑃 𝑢𝑢𝑢𝑢𝑢𝑢𝑢𝑢 =
𝑆𝑆𝑆𝑆𝑆𝑆𝑆𝑆𝑆𝑆𝑆𝑆𝑆𝑆 𝑎𝑎𝑎𝑎𝑎𝑎𝑎𝑎 (𝑎𝑎𝑎𝑎𝑎𝑎𝑎𝑎 𝑣𝑣𝑣𝑣𝑣𝑣𝑣𝑣𝑣𝑣) =
𝑊𝑊𝑊𝑊𝑊𝑊𝑊𝑊ℎ𝑡𝑡 𝑜𝑜𝑜𝑜 𝑒𝑒𝑒𝑒ℎ𝑦𝑦𝑦𝑦𝑦𝑦𝑦𝑦𝑦𝑦 𝑔𝑔𝑔𝑔𝑔𝑔𝑔𝑔𝑔𝑔𝑔𝑔 =
𝑇𝑇ℎ𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒 𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒 𝑜𝑜𝑜𝑜 𝑤𝑤𝑤𝑤𝑤𝑤𝑤𝑤𝑤𝑤 𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝 =