Alkylphenol

Alkylphenols are a family of organic compounds obtained by the alkylation of phenols. 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.[1]

Chemical structure of the alkylphenol nonylphenol

Production

The long-chain alkylphenols are prepared by alkylation of phenol with alkenes:

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

In this way, about 500M kg/y are produced.[1]

Environmental controversy over nonylphenols

Alkylphenols are xenoestrogens.[2] 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.[3]

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 copy paper and high performance rubber products. They have been used in industry for over 40 years.

gollark: This is ***evil*** code.
gollark: Not my code.
gollark: This literally says "pay attention to what you run", *but actually warns you twice*.
gollark: ```lua --Error screen term.clear() term.setCursorPos(1,1) print("ERROR!!!") sleep(0.1) print("ERROR CODE: ERR_OS_CORRUPT") sleep(0.1) print("Detailed information for diagnostics follow:") sleep(0.1) print("0x00000001 0x00000002 0x00000010") sleep(0.1) print("0x00000101 0x00120000 0x01000300") sleep(0.1) print("0x00000000 0x00001040 0x0000000F") sleep(0.1) print("0x00010506 0x01200040 0x00000003") sleep(0.1) term.setCursorPos(1,10) sleep(0.3) print("If you installed any new hardware or software,") sleep(0.1) print("try removing them before restarting.") sleep(0.1) print("If the problem still persists, bring your computer") sleep(0.1) print("to a technician.") sleep(0.2) print("Error program left a message: Pay attention to what you run next time ;)") sleep(0.1) term.setCursorPos(1,17) sleep(0.3) print("You will lose all unsaved work.") sleep(2) print("This computer has been terminated.")```
gollark: WHY™

References
  1. Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 978-3527306732.CS1 maint: uses authors parameter (link).
  2. Kochukov, Y.; Jeng, J.; Watson, S. (May 2009). "Alkylphenol xenoestrogens with varying carbon chain lengths differentially and potently activate signaling and functional responses in GH3/B6/F10 somatomammotropes". Environmental Health Perspectives. 117 (5): 723–730. doi:10.1289/ehp.0800182. ISSN 0091-6765. PMC 2685833. PMID 19479013.
  3. European Bans on Surfactant Trigger Transatlantic Debate
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