Nonylphenol

Nonylphenol
IUPAC name 4-(2,4-dimethylheptan-3-yl)phenol
Other names Phenol, nonyl-
Identifiers
CAS number	25154-52-3 Y, 104-40-5, 84852-15-3, 11066-49-2
PubChem	67296
ChemSpider	60628 Y
ChEMBL	CHEMBL153062 N
Jmol-3D images	Image 1
SMILES Oc1ccccc1CCCCCCCCC
InChI InChI=1S/C15H24O/c1-2-3-4-5-6-7-8-11-14-12-9-10-13-15(14)16/h9-10,12-13,16H,2-8,11H2,1H3 Y Key: SNQQPOLDUKLAAF-UHFFFAOYSA-N Y InChI=1/C15H24O/c1-2-3-4-5-6-7-8-11-14-12-9-10-13-15(14)16/h9-10,12-13,16H,2-8,11H2,1H3 Key: SNQQPOLDUKLAAF-UHFFFAOYAP
Properties
Molecular formula	C15H24O
Molar mass	220.35 g/mol
Appearance	Light yellow viscous liquid with phenolic smell [1]
Density	0.953
Melting point	−8 – 2 °C
Boiling point	293 to 297 °C
Solubility in water	6 mg/L (pH 7)
Hazards
Main hazards	low level endrocrine disruptor
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Nonylphenol is a family of closely related organic compounds, a subset of the alkylphenols. This collection of compounds is a precursor to commercially important detergents. Nonylphenol features both polar and hydrophobic subunits, the phenol and the hydrocarbon tail.

Production and basic properties

The material known collectively as nonylphenol is produced by acid-catalyzed alkylation of phenol with a mixture of nonenes. Millions of kilograms are produced annually.^[2] The nonyl group, which is highly branched, attaches to the phenol ring via the 4- and, to lesser extent, the 2-positions. This mixture of isomers is usually available as a pale yellow liquid, although the pure compounds are colorless. The organic compound 1-nonyl-4-phenol is not normally a component of what is marketed as nonylphenol. The nonylphenols are poorly soluble in water but soluble in alcohol.

In the environment, nonylphenols arise from the degradation of the nonaphenol ethoxylates, which are detergents.

Nonylphenol has been found to be a component of the slime produced by the velvet worm as a defence mechanism.

Applications

Alkylphenols are subjected to ethoxylation to give alkylphenol ethoxylates (APEs), which are widely used as industrial surfactants. They are used in applications as disparate as the processing of wool and metals, as emulsifiers for emulsion polymerization, as laboratory detergents, and as pesticides. APEs are a component of some household detergents outside of Europe. In Europe, due to environmental concerns, they have been replaced by more expensive alcohol ethoxylates, which are less problematic environmentally. Nonoxynol-9, one of the APEs, is used as a surfactant in cleaning and cosmetic products, and as a spermicide in contraceptives.

Health and environmental hazards

Nonylphenol is considered to be an endocrine disruptor due to weak ability to mimic estrogen and in turn disrupt the natural balance of hormones in affected organisms.^[3][4][5] The effect is weak because nonylphenols are not very close structural mimics of estradiol, but the levels of nonylphenol can be sufficiently high to compensate.

Structure of the hormone estradiol and one of the nonylphenols.

Occurrence in the environment

Nonylphenols have been detected widely in waste water streams across the globe, which is a concern since it is toxic to many aquatic organisms. In the US, nonylphenols have been detected both in the Great Lakes and in the region of New York City.^[6] In 1984, the formation of 4-nonylphenols from nonylphenol ethoxylates in wastewater treatment plants was first discovered.^[7] Nonylphenol is persistent in the environment,^[8] therefore lingers with the potential to negatively affect organisms it comes in contact with.

Environmental protection policies

Nonylphenol and nonyphenol ethoxylates have been restricted in the European Union as a hazard to human and environmental safety.^[9]

For freshwater ecosystems, the Environmental Protection Agency has set two types of standards: the first which is considered acute criteria is one-hour average concentration of nonylphenol does not exceed 28 μg/L more than once every three years on the average.^[10]

For saltwater ecosystems, the standard is considered to be chronic criteria and is set to four-day average concentration of nonylphenol that does not exceed 6.6 μg/l more than once every three years on the average. ^[10]

References

1. ^ Record of Nonylphenol, mixed isomers in the GESTIS Substance Database from the IFA, accessed on 6 April 2011
2. ^ 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.
3. ^ “Review article: Nonylphenol in the environment: A critical review on occurrence, fate, toxicity and treatment in wastewaters” A. Soares, B. Guieysse, B. Jefferson, E. Cartmell, J.N. Lester Environment International 2008, Volume 34, Pages 1033-1049. doi:10.1016/j.envint.2008.01.004 PMID 18282600
4. ^ Minnesota Pollution Control Agency Statewide Endocrine Disrupting Compound Monitoring Study, 2007 - 2008
5. ^ Nonylphenol, Environmental Working Group
6. ^ D. T. Bennie, C. A. Sullivan, H.-B. Lee, T. E. Peart and R. J. Maguire (1997). "Occurrence of alkylphenols and alkylphenol mono- and diethoxylates in natural waters of the Laurentian Great Lakes and the upper St. Lawrence River". Science of the Total Environment 193 (3): 263–275. doi:10.1016/S0048-9697(96)05386-7. 
7. ^ W. Giger, P. H. Brunner, C. Schaffner (1984). "4-Nonylphenol in sewage sludge: accumulation of toxic metabolites from nonionic surfactants". Science 225 (4662): 623–625. doi:10.1126/science.6740328. PMID 6740328. 
8. ^ Dayue Y. Shang, Robie W. Macdonald, and Michael G. Ikonomou. 1999. Persistence of Nonylphenol Ethoxylate Surfactants and Their Primary Degradation Products in Sediments from near a Municipal Outfall in the Strait of Georgia, British Columbia, Canada, Environmental Science and Technology 33 (9), pp 1366–1372
9. ^ Official Journal of the European Union: DIRECTIVE 2003/53/EC OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 18 June 2003 amending for the 26th time Council Directive 76/769/EEC relating to restrictions on the marketing and use of certain dangerous substances and preparations (nonylphenol, nonylphenol ethoxylate and cement), July 17, 2003
10. ^ ^{a b} Aquatic Life Criteria for Nonylphenol, United States Environmental Protection Agency