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Nonylphenol

Chemical structure and properties

Nonylphenols fall into the general chemical category of alkylphenols. Another alkylphenol is Bisphenol-A, which is found in plastic water bottles. The structure of NPs may vary. The nonyl group can be attached to the phenol ring at various locations, usually the 4- and, to lesser extent, the 2-positions, and can be either branched or linear. A branched nonylphenol, 4-nonylphenol, is the most widely produced and marketed nonylphenol. The mixture of nonylphenol isomers is a pale yellow liquid, although the pure compounds are colorless. The nonylphenols are moderatley soluble in water but soluble in alcohol.

Nonylphenol arises from the degradation of Nonylphenol ethoxylates in the environment. Nonylphenol ethoxylates fall into the general chemical category of alkylphenol ethoxylates APEs. NPEs are a clear to light orange color liquid. Nonylphenol ethoxylates are nonionic in water, which means that they have no charge. Because of this property they are used as detergents, cleaners, emulsfiers, and a variety of other applications. They are hydrophilic, water loving, at one end and hydrophobic, water fearing, at the other end, which allows them to surround non-polar substances like oil and grease, and exclude them from water.

Production

Nonylphenols are produced by acid-catalyzed alkylation of phenol with a mixture of nonenes. To make NPEs manufacturer's react NP with ethlylene oxide under basic conditions. Approximately 100 to 500 millions pounds of nonylphenol are produced anualy, based on the most widely produced nonylphenols.

Uses

Nonylphenol is used in manufacturing antiooxidants, lubricating oil additives and the production of NPEs. Nonylphenol exthoxylates have a variety of industrial and household uses including detergents, emulsifiers, wetting and dispersing agents, antistatic agents, demulsifiers and solubilisers.

Another surfactant nonoxynol, which was once used as intravaginal spermicide and condom lubricant was found to metabolize into free nonylphenol when administered to lab animals.

Occurrence in the environment

Water supplies—we will discuss how manufacturers release NPs and NPEs into the environment and how they subsequently enter water systems.

In aquatic environments waste from sewage treatment plants are the main source nonylphenol. Nonylphenol is found in river water and sediments as well as soil and groundwater. In surface water the concentration of nonylphenol will decrease due to photolysis induced by sunlight, but in sediment it is estimated that is has a half life of mare than 60 years. Due to its low solubility it is found in higher concentrations in sediment versus in water.

The occurrence of nonylphenol in soil is not as well studied as in aquatic environment, but the major concern is in sewage sludge that is recycled into agricultural land. There are many factors that influence the degradation of nonylphenol in soil including the depth of the sludge layer oxygen availability and contaminant bioavailability. Mobility of nonylphenol in soil is low.

Environmental Hazards

Aquatic toxicity

The effects of nonylphenol in the environment are the feminization of aquatic organisms, decreased male fertility, and decreased survival in young fish. Nonylphenol can cause endocrine disruption in fish by interacting with estrogen receptors and androgen receptors. In the liver NP can disrupt steriodgenesis and can interfere with the level of FSH (follicle-stimulating hormone) released from the pituitary Concentrations of NP that inhibit reproductive development and function in fish also damaged kidneys, decreased body weight, and induced a stressed behavior.

Human Exposure

Diet seems the most significant source of exposure of NPs to humans. For example, food samples were found with concentrations ranging from 0.1 to 19.4 µg/kg in a diet survey in Germany. In Taiwan NP concentrations in food ranged from 5.8 to 235.8 µg/kg. Seafood in particular was found to have a high concentration of NP.

Drinking water does not represent a significant source of exposure in comparison to other sources such as food packing materials, cleaning products, and carious skin care products. Concentrations of nonylphenol in treated drinking water varied from 85 ng/l in Spain to 15 ng/l in Germany.

Health Hazards

Toxicity—provide levels of exposure that have been to cause adverse effects.

Endocrine Disruption—discuss what physiological effects are seen in model organisms (mice). For example: decreases in epididymal sperm density or testicular sperm head counts, increased in estrous cycle length, etc.

Alkylphenols like nonylphenol and Bisphenol-A were found to have estrogenic effects in the body. They are also known as xenoestrogens. Estrogenic substances and other endocrine disruptors are compounds that have hormone-like effects in both wildlife and humans. Xenoestrogens usually function by binding to estrogen receptors and acting competitively toward natural estrogens. Alkylphenols like nonylphenol and related compounds are found in pesticides and industrial chemicals. Nonylphenol was discovered to have hormone like affects accidentally because it contaminated other experiments in laboratories that were studying natural estrogens that were using polystyrene tubes. The detergent nonylphenol is harmful when it degrades into nonylphenol ethoxylate in sewage treatment plants. Unfortunately there limited articles on the endocrine activity of nonylphenol in comparison to BPA. One study conducted in Italian women showed that nonylphenol was one of the highest contaminants at a concentration of 32 ng/mL in breast milk when compared to other alkylphenols octylphenol, nonylphenol monoethoxylate, and two octylphenol ethoxylates. The study found a positive correlation between fish consumption and the concentration of NP in breast milk. This is a large problem because breast milk is the main source of nourishment for newborns, who are in early stages of development where hormones are very influential. Elevated levels of endocrine disruptors in breast milk have been associated with negative affects on neurological development, growth and memory function.

Nonylphenol is also capable of inducing breast tumore cell proliferation.

Protection policies

The European Union has included NP on the list of priority hazardous substances for surface water in the Water Framework Directive. They are now implementing a drastic reduction policy of NP's in surface waterways. The Environmental quality standard for NP was proposed to be 0.3 ug/l. In the USA, the EPA set criteria that recommended the NP concentration shoudl not exceed 6.6 ug/l in fresh water and 1.7 ug/l in saltwater. In other Asian and South American countries there is still a large about of APE's and little regulation.

OliviaHall10 (talk) 21:09, 19 February 2014 (UTC)

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OliviaHall10/sandbox

Names
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
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL153062 N
ChemSpider	60628 Y
PubChem CID	67296
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
SMILES Oc1ccccc1CCCCCCCCC
Properties
Chemical formula	C15H24O
Molar mass	220.35 g/mol
Appearance	Light yellow viscous liquid with phenolic smell
Density	0.953
Melting point	−8 – 2 °C
Boiling point	293 to 297 °C
Solubility in water	6 mg/L (pH 7)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	low level endrocrine disruptor
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Tracking categories (test):

• SizeSet

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. 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.

Natural occurrences

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. 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. In 1984, the formation of 4-nonylphenols from nonylphenol ethoxylates in wastewater treatment plants was first discovered. Nonylphenol is persistent in the environment, 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.

For freshwater ecosystems, the Environmental Protection Agency has set two types of standards, acute and chronic. The acute criteria is a one-hour average concentration of nonylphenol not to exceed 28 μg/L more than once every three years on the average in order to protect fresh water aquatic life and their uses. The chronic criteria is a four-hour average concentration of nonylphenol not to exceed 6.6 μg/L more than once every three years on average.

For saltwater ecosystems, the acute criteria is set at 7.0 μg/L and the chronic criteria is set at 1.7 μg/L.

References

OliviaHall10 (talk) 16:47, 13 March 2014 (UTC)