Design Analysis of Phenol
Phenol, also known as carbolic acid, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (-C6H5) bonded to a hydroxyl group (-OH). It is mildly acidic, but requires careful handling due to its propensity to cause chemical burns. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum. It is an important industrial commodity as a precursor to many materials and useful compounds.[4] Its major uses involve its conversion to plastics or related materials. Phenol and its chemical derivatives are key for building polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.
Although similar to alcohols, phenols have unique distinguishing properties. Unlike in alcohols where the hydroxyl group is bound to a saturated carbon atom,[5] in phenols the hydroxyl group is attached to an unsaturated aromatic (alternating double and single bond) hydrocarbon ring such as benzene.[6] Consequently, phenols have greater acidity than alcohols due to stabilization of the conjugate base through resonance in the aromatic ring.
Contents [hide]
1 Properties
1.1 Acidity
1.1.1 Phenoxide anion
1.1.2 Tautomerism
1.2 Reactions
2 Production
3 Uses
3.1 Niche uses
4 History
4.1 Second World War
5 Natural occurrences
5.1 Occurrence in whisky
6 Biodegradation
7 Toxicity
8 Phenols
9 See also
10 References
11 External links
Properties[edit]
Phenol is appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.88 M). Homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are also possible. The sodium salt of phenol, sodium phenoxide, is far more water soluble.
Acidity[edit]
Phenol is weakly acidic and at high pHs gives the phenolate anion C6H5O− (also called phenoxide):[7]
PhOH ⇌ PhO− +
Although similar to alcohols, phenols have unique distinguishing properties. Unlike in alcohols where the hydroxyl group is bound to a saturated carbon atom,[5] in phenols the hydroxyl group is attached to an unsaturated aromatic (alternating double and single bond) hydrocarbon ring such as benzene.[6] Consequently, phenols have greater acidity than alcohols due to stabilization of the conjugate base through resonance in the aromatic ring.
Contents [hide]
1 Properties
1.1 Acidity
1.1.1 Phenoxide anion
1.1.2 Tautomerism
1.2 Reactions
2 Production
3 Uses
3.1 Niche uses
4 History
4.1 Second World War
5 Natural occurrences
5.1 Occurrence in whisky
6 Biodegradation
7 Toxicity
8 Phenols
9 See also
10 References
11 External links
Properties[edit]
Phenol is appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.88 M). Homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are also possible. The sodium salt of phenol, sodium phenoxide, is far more water soluble.
Acidity[edit]
Phenol is weakly acidic and at high pHs gives the phenolate anion C6H5O− (also called phenoxide):[7]
PhOH ⇌ PhO− +