Name: Duong Tien Quang Huy

Matriculation Number: U1840650L

BS1003 Organic Chemistry

Practical 2: Preparation and use of indigo

1. Introduction
- Dyes, which are coloured organic compound, have been used to make the colourful fabrics for
thousands of years. Ancient dyes were entirely made of natural materials such as the mucous
secretion of Murex brandaris (Tyrian purple), the roots of the madder plant (Alizarine) and the
leaves of certain plants (Indigo). Nowadays, synthetic dyes contain a large amount of polar
functional groups that allow dyes to interact with fabrics, so they are more stable and remain in
the fabric during washing. There are three main groups: vat dyes, mordant dyes and direct dyes.
- Indigo, one type of vat dyes, was obtained by fermentation of Isatis tinctoria or plants of the
Indigofera species. Modern indigo is synthetically produced from 2-nitrobenzaldehyde.
- The vat dying procedure, which is shown below, is carried out by reducing the indigo with
sodium hydrosulphite. A piece of cotton is exposited to the air after soaking in the resulting
solution.

Figure 1: Vat dying process

2. Methodology
 Weight of 2-nitrobenzaldehyde 1 grams
Volume of acetone used 20 mL
Volume of NaOH 2M used 8 mL
Volume of C2H5OH used 20 mL
Volume of H2O used More than 100 mL
Weight of Na2S2O4 0.6 grams
Cotton square 1 piece

Table 1: Material for the experiment

- Synthesis of indigo
+ Dissolve 1 gram of 2-nitrobenzaldehyde in 150 mL barker with 20 mL acetone, then add 35
mL of water, 5 mL NaOH 2M and stir vigorously with a glass rod for about 5 minutes.
+ Collect the purple-blue precipitate by using Hirsch funnel and suction filtration. Rinse the
beaker and glass rod with water to maximize the quantity of the product. Wash the precipitate by
water until the flow through the funnel is colorless, and then wash by 20 mL ethanol. Dry the
solid at the pump for 5-10 minutes.
+ Transfer the solid to a glass that has been weight-measured, dry at 120ºC for 15 minutes and
reweighs the glass, so we can calculate the mass of product.
- Vat dying of cotton
+ Add 100-200 mg of indigo into a 100 mL beaker with a few drops of ethanol to make a paste.
Add 1 mL water to suspend the paste, 3 mL NaOH 2M and a solution that contains 0.6 grams of
Na2S2O4 (sodium hydrosulphite) and 20 mL H2O.
+ Heat the mixture in the 60oC water bath until the colour of solution becomes yellow, add 40
mL of hot water to the mixture. After that, we immerse the cotton square in this yellow liquid for
40 minutes. Remove the cotton, squeeze it dry and hang it in the air for 15 minutes before
washing it in hot soapy water, and in tap water after that. Dry the cotton square by the hairdryer.
3. Result
Color of the liquid before adding NaOH Colorless
Color of the liquid after adding NaOH Dark blue
Color of cotton before hang in the air Yellow
Color of cotton after hang in the air Dark green
Color of cotton after wash and dry Blue
The weight of empty glass 53.2537 grams
The weight of glass with indigo 53.8683 grams
The actual weight of indigo 53.8683 - 53.2537 = 0.6146 g grams

Table 2: Result of experiment

4. Discussion
- The result:
+ After adding NaOH, the reaction occurs to form indigo, which is blue. Therefore, the colour of
the mixture becomes darker.

+ After adding Na2S2O4, the reaction occurs to form leucoindigo, which is yellow. Therefore, the
colour of the mixture becomes yellow. When we hang the cotton square in the air, counter-
reaction occurs to form indigo, so the colour of cotton square becomes blue.

5. Conclusion
- In this second practical, we have learnt about the mechanism of synthetic process to make
indigo from 2-nitrobenzaldehyde and the vat dyeing of cotton. We also have more information
about the natural source of some ancient dyes such as Tyrian purple, Alizarine, Indigo.