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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/13 13:45:55」(JST)

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Chemical structure of the alkylphenol nonylphenol

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]

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

These xenobiotic compounds are known to be weak endocrine disruptors.

References

^ ^a ^b Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim.doi:10.1002/14356007.a19_313.
^ 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. edit
^ European Bans on Surfactant Trigger Transatlantic Debate

English Journal

Altered ventral neck muscle deformation for individuals with whiplash associated disorder compared to healthy controls - a case-control ultrasound study.

Peterson G1, Dedering Å2, Andersson E3, Nilsson D4, Trygg J4, Peolsson M4, Wallman T5, Peolsson A3.
Manual therapy.Man Ther.2015 Apr;20(2):319-27. doi: 10.1016/j.math.2014.10.006. Epub 2014 Oct 15.
Previous studies have shown altered neck muscle function in individuals with chronic whiplash associated disorder (WAD). However, we lack real-time investigations with non-invasive methods that can distinguish between the different ventral neck muscle layers. This study investigated deformations and
PMID 25454684

Group learning capacity: the roles of open-mindedness and shared vision.

Lord M1.
Frontiers in psychology.Front Psychol.2015 Feb 27;6:150. doi: 10.3389/fpsyg.2015.00150. eCollection 2015.
Open-mindedness (OPM) is a construct that is considered a key foundational aspect of learning in individuals, groups and organizations. Also known as critical inquiry or reflection, OPM is believed to increase learning through examination of prior beliefs, decisions and mistakes, and also through op
PMID 25774141

Successful leukocytapheresis therapy in a patient with rheumatoid arthritis on maintenance hemodialysis.

Maeshima K1, Torigoe M, Iwakura M, Yamanaka K, Ishii K.
Modern rheumatology / the Japan Rheumatism Association.Mod Rheumatol.2015 Jan;25(1):154-7. doi: 10.3109/14397595.2013.874752. Epub 2014 Feb 11.
We report the case of a 44-year-old female undergoing maintenance hemodialysis in whom early-phase rheumatoid arthritis (RA) was successfully treated by leukocytapheresis (LCAP). The effects of prednisone, tacrolimus, and etanercept were limited, but LCAP was highly effective and its efficacy contin
PMID 24517518

Japanese Journal

潰瘍性大腸炎に対する1.5l血液処理白血球除去療法(1.5l LCAP療法)の治療効果と長期予後についての検討

島田昌明,岩瀬弘明,都築智之 [他]
医療 : 国立医療学会誌 66(5), 208-213, 2012-05
NAID 40019360583

関節リウマチ患者に対する白血球除去療法の治療効果発現のメカニズム

日高利彦
日本臨床免疫学会会誌 = Japanese journal of clinical immunology 34(6), 447-455, 2011-12-31
NAID 10030465082

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