Alkylphenols are a family of organic compounds obtained by the alkylation of phenol

Phenol

Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...

s. The term is usually reserved for commercially important propylphenol, butylphenol, amylphenol, heptylphenol, octylphenol, nonylphenol, dodecylphenol and related "long chain alkylphenols" (LCAPs). Methylphenols and ethylphenols are also alkylphenols, but they are more commonly referred to by their specific names, cresols and xylenols.

Production

The long-chain alkylphenols are prepared by alkylation

Alkylation

Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene . Alkylating agents are widely used in chemistry because the alkyl group is probably the most common group encountered in...

 of phenol

Phenol

Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...

 with alkenes:

C₆H₅OH + RR'C=CHR" → RR'CH-CHR"-C₆H₄OH

In this way, about 500M kg/y are produced.

Environmental controversy over nonylphenols

Alkylphenols are xenoestrogens. The European Union has implemented sales and use restrictions on certain applications in which nonylphenols are used because of their alleged "toxicity, persistence, and the liability to bioaccumulate" but the United States EPA has taken a slower approach to make sure that action is based on "sound science".

Uses of long-chain alkylphenols

The long-chain alkylphenols are used extensively as precursors to the detergents, as additives for fuels and lubricants, polymers, and as components in phenolic resins. These compounds are also used as building block chemicals that are also used in making fragrances, thermoplastic elastomers, antioxidants, oil field chemicals and fire retardant materials. Through the downstream use in making alkylphenolic resins, alkylphenols are also found in tires, adhesives, coatings, carbonless copypaper and high performance rubber products. They have been used in industry for over 40 years.

These xenobiotic

Xenobiotic

A xenobiotic is a chemical which is found in an organism but which is not normally produced or expected to be present in it. It can also cover substances which are present in much higher concentrations than are usual...

 compounds are known, weak endocrine disruptor

Endocrine disruptor

Endocrine disruptors are chemicals that interfere with endocrine in animals, including humans. These disruptions can cause cancerous tumors, birth defects, and other developmental disorders...

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