Isopropyl alcohol structure, properties, synthesis and uses

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Anthony Golden

The isopropyl alcohol or isopropanol is an organic compound whose chemical formula is CH3CHOHCH3 or (CH3)twoCHOH. It belongs to one of the most important families in organic chemistry: alcohols, as its name indicates..

It is a liquid, colorless, strong-smelling, volatile and flammable chemical compound. It is a weak acid and base at the same time, similar to water, depending on the pH of the solution and / or the presence of an acid or a base stronger than it. Isopropyl alcohol vapors cause very mild irritation to the mucosa of the nose, throat and eyes..

Source: Ryan Hyde via Flickr

Isopropyl alcohol is used as the main ingredient in various products in the pharmaceutical, chemical, commercial and household industries. Due to its antimicrobial properties, it is widely used as an antiseptic on the skin and mucosa, and as a disinfectant in inert materials..

It is very useful as a solvent, since it has low toxicity, and it is also used as a gasoline additive..

Likewise, it is the raw material for the synthesis of other organic compounds by substituting the hydroxyl (OH) functional group. In this way, this alcohol is very useful and versatile to obtain other organic compounds; such as alkoxides, alkyl halides, among other chemical compounds.

Article index

  • 1 Structure of isopropyl alcohol or isopropanol
  • 2 Physical and chemical properties
    • 2.1 Molecular weight
    • 2.2 Physical appearance
    • 2.3 Odor
    • 2.4 Melting point
    • 2.5 Boiling point
    • 2.6 Density
    • 2.7 Solubility
    • 2.8 pKa
    • 2.9 Conjugate base
    • 2.10 Absorbance
  • 3 Nomenclature
  • 4 Synthesis
  • 5 Uses
    • 5.1 In summary 
    • 5.2 For cleaning
    • 5.3 Antimicrobial
    • 5.4 Medicine
    • 5.5 Solvent
  • 6 References

Structure of isopropyl alcohol or isopropanol

Source: Jynto [CC0], from Wikimedia Commons

The upper image shows the structure of isopropyl alcohol or isopropanol with a model of spheres and bars. The three gray spheres represent the carbon atoms, which make up the isopropyl group, attached to a hydroxyl (red and white spheres).

Like all alcohols, structurally they are made up of an alkane; in this case, propane. This gives alcohol the characteristic of lipophilic (ability to dissolve fats given its affinity for them). It is attached to a hydroxyl group (-OH), which on the other hand gives the structure the hydrophilic characteristic.

Therefore, isopropyl alcohol can dissolve grease or stains. Note that the -OH group is attached to the middle carbon (2nd, that is, attached to two other carbon atoms), which shows that this compound is a secondary alcohol.

Its boiling point is lower than that of water (82.6 ° C), which can be explained from the propane skeleton, which can hardly interact with each other by means of London dispersion forces; lower than hydrogen bonds (CH3)twoCHO-H - H-O-CH (CH3)two.

Physical and chemical properties

Molecular weight

60.10 g / mol.

Physical appearance

Liquid and colorless and flammable.

Odor

Strong smell

Melting point

-89 ° C.

Boiling point

82.6 ° C.

Density

0.786 g / ml at 20 ° C.

Solubility

It is soluble in water and soluble in organic compounds such as chloroform, benzene, ethanol, glycerin, ether, and acetone. It is insoluble in saline solutions.

pKa

17

Conjugate base

(CH3)twoCHO-

Absorbance

Isopropyl alcohol in the visible ultraviolet spectrum has a maximum absorbance at 205 nm.

Nomenclature

In the nomenclature of organic compounds, there are two systems: that of common names, and the internationally standardized IUPAC system..

Isopropyl alcohol corresponds to the common name, ending in the suffix -ico, preceded by the word alcohol and with the name of the alkyl group. The alkyl group is made up of 3 carbon atoms, two methyl ends and the one in the center attached to the -OH group; i.e. isopropyl group.

Isopropyl alcohol or isopropanol has other names such as 2-propanol, sec-propyl alcohol, among others; but according to the IUPAC nomenclature, it is called propane-2-ol.

According to this nomenclature, it is first 'propane' because the carbon chain contains or is made up of three carbon atoms.

Second, the position of the OH group is indicated on the carbon chain using a number; in this case it is 2.

The name ends in 'ol', characteristic of organic compounds of the alcohol family because they contain the hydroxyl group (-OH).

The name isopropanol is considered incorrect by the IUPAC, due to the absence of the hydrocarbon isopropane.

Synthesis

The chemical synthesis reaction of isopropyl alcohol on an industrial level is basically a water addition reaction; that is, hydration.

The starting product for the synthesis or obtaining is propene, to which water is added. Propene CH3-CH = CHtwo It is an alkene, a hydrocarbon derived from petroleum. By hydration a hydrogen (H) is replaced by a hydroxyl group (OH).

Water is added to the alkene propene in the presence of acids, to produce isopropanol alcohol..

There are two ways to hydrate it: the direct one, and the indirect one carried out under polar conditions, generating isopropanol..

CH3-CH = CHtwo (Propene) => CH3CHOHCH3 (Isopropanol)

In direct hydration, in the gas or liquid phase, the propene is hydrated by acid catalysis at high pressure.

In indirect hydration, propene reacts with sulfuric acid, forming sulfate esters that by hydrolysis produce isopropyl alcohol.

Isopropyl alcohol is also obtained by hydrogenating acetone in the liquid phase. These processes are followed by distillation to separate the alcohol from the water, generating anhydrous isopropyl alcohol with a yield of approximately 88%..

Applications

Isopropyl alcohol has a wide range of uses on a chemical level. It is useful for making other chemical compounds. It has numerous applications at an industrial level, for cleaning equipment, at a medical level, in household products and for cosmetic use..

This alcohol is used in perfumes, hair dyes, lacquers, soaps, among other products as you will see below. Its use is mainly and basically external, since its inhalation or ingestion is very toxic for living beings.

In summary

From it, alkyl halides can be obtained by generally substituting bromine (Br) or chlorine (Cl), the functional group alcohol (OH).

By carrying out a process of oxidation of isopropyl alcohol with chromic acid, acetone can be given rise. It can form alkoxides as a result of the reaction of isopropyl alcohol with some metals such as potassium.

For cleaning

Isopropyl alcohol is ideal for cleaning and maintaining optical glasses such as lenses and electronic equipment, among others. This alcohol evaporates quickly, does not leave residues or traces, and does not present toxicity in its applications or external use.

Antimicrobial

Isopropanol has antimicrobial properties, causes denaturation of bacterial proteins, dissolves lipoproteins of the cell membrane, among other effects.

As an antiseptic, isopropyl alcohol is applied to the skin and mucous membranes and evaporates quickly, leaving a cooling effect. It is used to perform minor surgeries, insertion of needles, catheters, among other invasive procedures. In addition, it is used as a disinfectant for medical instruments..

Medicine

Apart from its use as an antimicrobial, it is required in laboratories for cleaning, conservation of samples, and DNA extraction..

This alcohol is also very useful in the preparation of pharmacological products. Isopropyl alcohol is mixed with fragrances and essential oils, and is used in therapeutic compounds to rub on the body.

Solvent

Isopropyl alcohol has the property of dissolving some oils, natural resins, gums, alkaloids, ethylcellulose, among other chemical compounds.

References

  1. Carey, F. A. (2006). Organic Chemistry Sixth Edition. Mc Graw Hill Publishing House
  2. Morrison, R. and Boyd, R. (1990). Organic Chemistry. Fifth edition. Editorial Addison-Wesley Iberoamericana.
  3. PubChem. (2019). Isopropyl alcohol. Recovered from: pubchem.ncbi.nlm.nih.gov
  4. Wikipedia. (2018). Isopropyl alcohol. Recovered from: en.wikipedia.org
  5. Wade, L. (April 5, 2018). Isopropyl alcohol. Encyclopaedia Britannica. Recovered from: britannica.com

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