Use of Cyclohexanol in Manufacturing

Cyclohexanol, formula (CH2)5CHOH, is a secondary alcohol existing as a colourless,

viscous liquid with a camphor-like odour. As an alcohol, its functional group is the hydroxyl

group (OH) which has 2 covalent bonds: the O−¿H bond and the C−¿O bond. The oxygen

molecule has a much greater electronegativity when compared to the hydrogen and carbon

molecules. This difference in electronegativity makes these two bonds very reactive.

Cyclohexanol undergoes typical oxidation and esterification reactions to produce cyclohexanone

and cyclohexyl esters, respectively. Additionally, the O−¿H bond is polarized by uneven charge

distribution which gives rise to hydrogen bonding within alcohols. Hydrogen bonding is a strong

intermolecular force of attraction and a lot of energy is required to overcome it. As such,

alcohols have relatively higher boiling points than comparative alkanes and other elements of

similar molecular weight that do not have hydrogen bonding. The boiling point of cyclohexanol

(lit., b.p. 161 ℃) is comparatively high to that of cyclohexane (lit., b.p. 80℃).1

Manufacturing involves the use of labour, machinery, tools, as well as, chemical and

biological processing to convert raw materials into tangible products for sale or immediate usage.

Cyclohexanol has physical and chemical properties which make it useful in the manufacture of

various products. One of its primary uses its use in the manufacture of nylon. Cyclohexanol is

also commonly used in the textile industry and the lacquer industry.

The most significant use of cyclohexanol is its role in the production of nylon. Nylon is a

light weight, synthetic fabric with great elasticity, strength and durability used to make a wide

range of items including rugs, ropes, bowls, toothbrushes, umbrellas, parachutes and clothing.

The most common form of nylon is nylon 6.6 which is a polyamide made from the reaction of

hexane-1,6-dicarboxylic acid (adipic acid) and 1,6-diaminohexane.2 Cyclohexanol is an

intermediate in the production of adipic acid, one of the key raw materials in the production of

nylon.3 The oxidation of cyclohexanol with nitric acid synthesizes the adipic acid necessary for

nylon production. Cyclohexanol, as a secondary alcohol, readily undergoes oxidation due to

presence of the hydrogen atom attached to the alpha carbon. This C−¿H bond is easily broken in

oxidative conditions and promotes the formation of the C¿O producing cyclohexanone which is

necessary for the eventual synthesis of adipic acid. The large-scale production of adipic acid is

necessary to manufacture nylon fabric. However, the synthesis of adipic acid via the oxidation

of cyclohexanol has adverse effects on the environment. As said said by Mendoza4, nitrous

oxide which is a by-product of the reaction is a major cause of global warming and ozone

depletion.

Secondly, cyclohexanol is used in the lacquer industry. Lacquer is a clear liquid which

leaves a shine, hard coat when painted on a surface; it is often used to protect wood. Lacquers

consist of pyroxylin and resin solutions. According to Freitag and Stoye5, cyclohexanol is used in

cellulose nitrate combination lacquers and oil based paints. Cyclohexanol maintains the

homogeneous appearance of lacquers and paints throughout their drying phase and improves

their flow and gloss. This is possible because of the gentle dissolution properties of

cyclohexanol. Cyclohexanol is polar due to hydroxyl group and is able to dissolve strongly polar

resins. This improves the miscibility of alcohol-soluble pyroxylins (nitrocellulose) and resin

solutions which in turn smoothens the finish of paint jobs. In a similar manner, cyclohexanol is

useful as an emulsion stabilizer and homogenizer for soap and synthetic detergent in the textile

industry. Cyclohexanol also has a non-polar end which makes it possible to dissolve both polar

and non-polar compounds. As such, it can be used to form emulsions. Additionally, Choudhyur6

states that the textile industry uses cyclohexanol as a kier-boiling assistant. Kier-boiling is the
process of removing unwanted oils, fats, waxes and any soluble impurities adhering fibre. The

process is carried out in a Kier boiler at 100℃−¿120℃ for approximately 8 hours. Therefore,

cyclohexanol is a suitable solvent for Kier-boiling since it has a high boiling point due to the

strong hydrogen bonding present. Despite the wide scale use of cyclohexanol is the textile and

lacquer industries, data on toxic effects of cyclohexanol on humans are very limited.7 A major

drawback of the application of cyclohexanol is soap and detergent making is that cyclohexanol is

an eye, skin and mucus membrane irritant.8

 References

1. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A.R. Vogel’s Textbook of

Practical Organic Chemistry, 5th ed.; John Wiley & Sons: New York, 1989.

2. Maraj, S.; Samai, A. Chemistry for Cape; Caribbean Educational Publishers: La Romaine,

Trinidad, 2011; p 329.

3. NPCS Board of Consultants and Engineers. Monohydric Alcohols. In Industrial Alcohol

Technology Handbook; Asia Pacific Business: Lawrence Road, Dehli, 2010; pp 320-321.

4. Mendoza, D. Oxidation of Cyclohexanol to Adipic Acid, 2012. Scribd.

https://www.scribd.com/doc/114328909/Oxidation-of-Cyclohexanol-to-Adipic-Acid.

(accessed November 4, 2017).

5. Freitag, W., Stoye, D., Eds. Alcohols. In Paints, Coatings and Solvents, 2nd ed.; John Wiley

& Sons: Weinheim, Germany, 1998; pp 353 – 357.

6. Choudhyur, A. Scouring Cotton. In Textile Preparation and Dyeing [Online]; Science

Publishers: Enfield, NH, USA, 2006; pp 166 – 169. https://books.google.com.jm/books?id=

(accessed November 4, 2017).

7. Rekus, J.F. Cyclohexanol. In Complete Confined Spaces Handbook. [Online]; CRC : Boca

Raton, FL, 1994; pp 62-63. https://books.google.com.jm/books?id=-

St58bzOGMcC&printsec=frontcover&source=gbs_ge_summary_r&cad=0#v=onepage&q=c

yclohexanol&f=false (accessed November 2, 2017).

8. ChemicalBook. CAS Database List. Cyclohexanol, CAS No. 108-93-0;

http://www.chemicalbook.com/ChemicalProductProperty_EN_CB7852772.htm (accessed

November 5, 2017)