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NONYLPHENOL

4-nonylphenol = para-Nonylphenol = NPE

Molecular Weight: 220.35
CAS Number: 84852-15-3
Empirical Formula (Hill Notation): C15H24O
EC Number: 284-325-5

Nonylphenol is a colorless, viscous liquid with a characteristic phenolic odour. 
Nonylphenol is a mixture of isomers containing mainly p-nonylphenol. 
Nonylphenol is soluble in aliphatic alcohols, ketones, esters and aliphatic hydrocarbons and difficult soluble in water.
Nonylphenol is an organic compound of the wider family of alkylphenols. 
4-nonylphenol is a product of industrial synthesis formed during the alkylation process of phenols, particularly in the synthesis of polyethoxylate detergents. 
Because of their man-made origins, nonylphenols are classified as xenobiotics. 
In nonylphenols, a hydrocarbon chain of nine carbon atoms is attached to the phenol ring in either the ortho, meta, or para position, with the most common ring isomers being ortho or para. 
Moreover, the alkyl chains can exist as either linear n-alkyl chains, or complex branched chains. 
Nonylphenol is commonly obtained as a mixture of isomers, and is thus usually found as a pale yellow liquid at room temperature with a freezing point of -10°C and a boiling point of 295-320°C. 
However, pure isomers of nonylphenol crystallize readily at room temperatures and for example, para-n-nonylphenol, forms white crystals at room temperature.
Nonylphenol, and a related compound tert-octylphenol, were first detected as an air pollutant in New York City and New Jersey, probably due to its evaporation from the Hudson river and other smaller rivers in the region that routinely receive municipal wastewaters. 
It is possible that the atmosphere is a destructive sink for nonylphenol as nonylphenol is probably reactive with atmospheric radicals and/or is photoactive.

Definition
Nonylphenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail.
Nonylphenols can come in numerous structures, all of which may be considered alkylphenols. 
Nonylphenols are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers.[2] 
Nonylphenols are used extensively in epoxy formulation in North America[3][4] but its use has been phased out in Europe.[5] 
Nonylphenols are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and nonylphenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics.
Nonylphenol has attracted attention due to its prevalence in the environment and its potential role as an endocrine disruptor and xenoestrogen, due to its ability to act with estrogen-like activity.[6] 
The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain


General description
Nonylphenol is a toxic xenobiotic compound classified as an endocrine disrupter capable of interfering with the hormonal system of numerous organisms. 
Nonylphenol has been reported as antiandrogen by using a yeast detection system. 
Molecular mechanism for the antiandrogenic action of nonylphenol has been reported.
NPEs are nonionic surfactants that are used in a wide variety of industrial applications and consumer products. 
Many of NPE, such as laundry detergents, are “down-the-drain” applications. 
Some others, such as dust-control agents and deicers, lead to direct release to the environment. 
NPEs, though less toxic and persistent than NP, are also highly toxic to aquatic organisms, and, in the environment, degrade into NP.

Applications
Nonylphenol is used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers. 
4-nonylphenol can also be used to produce tris(4-nonyl-phenyl) phosphite (TNPP), which is an antioxidant used to protect polymers, such as rubber, Vinyl polymers, polyolefins, and polystyrenics in addition to being a stabilizer in plastic food packaging.
Barium and calcium salts of nonylphenol are also used as heat stabilizers for polyvinyl chloride (PVC).
Nonylphenol is also often used an intermediate in the manufacture of the non-ionic surfactants nonylphenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. Nonylphenol and nonylphenol ethoxylates are only used as components of household detergents outside of Europe.[2]
NonylPhenol, is used in many epoxy formulations mainly in North America.
4-nonylphenol is used in the processing of plastic.
4-nonylphenol is used as intermediate for the production of phosphate flame retardants.
4-nonylphenol used in the epoxy resin, paints, varnishes and ink industry.
4-nonylphenol is used as intermediate for production of formaldehyde resins.
4-nonylphenol is used asintermediate for production of polyols used in polyurethane industry.
4-nonylphenol is used as an intermediate for production of antioxidants.

Uses
Nonylphenols and their ethoxylates are used in products such as paints, floor covering material, grout and sealants, degreasing agents and detergents, lubricants, adhesives and in biocides. 
Nonylphenols  may also be present in textiles imported from non-EU countries.6,7,8
Nonylphenols have been used as emulsifiers and modifiers in paints, pesticides, textiles, and some personal care products. 
Nonylphenols  have also been used as plasticizers and antioxidants in plastics and resins
Nonylphenol ethoxylates are more commonly used than octylphenol ethoxylates. 
The alkylphenol ethoxylates enter the environment through human use of products containing them, through sewage, and through manufacturing waste streams.
Nonylphenols are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers. 

Commonly used in:
Household paints, colorants and wood finishes
Clothing and textiles
Paint and stain removers
Surface and drain cleaners
Indoor pesticides
Food packaging (contains related chemicals)
Footwear, toys and games (contains 4-nonylphenol)

PHYSICAL & CHEMICAL INFORMATION
Physical State; Appearance
COLOURLESS-TO-PALE YELLOW LIQUID WITH CHARACTERISTIC ODOUR. 
Formula: C15H24O
Molecular mass: 220.3
Boiling point: 290-300°C
Melting point: -8°C
Relative density (water = 1): 0.95 (20°C)
Solubility in water, g/100ml at 25°C: 0.06 (very poor)
Vapour pressure, Pa at 25°C: 0,3
Relative vapour density (air = 1): 7.59
Relative density of the vapour/air-mixture at 20°C (air = 1): 1.05
Flash point: 141-155°C c.c.
Auto-ignition temperature: 370°C
Octanol/water partition coefficient as log Pow: 4.48  

Reactivity Profile
NONYLPHENOL behaves as a very weak organic acid. Incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. 
Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. 
Likely to react exothermically with concentrated sulfuric acid and nitric acid.


Prevalence in the environment
Nonylphenol persists in aquatic environments and is moderately bioaccumulative.
Para-Nonylphenol is not readily biodegradable, and para-Nonylphenol can take months or longer to degrade in surface waters, soils, and sediments. 
Nonbiological degradation is negligible.[6] Nonylphenol is partially removed during municipal wastewater treatment due to sorption to suspended solids and biotransformation. 
Many products that contain nonylphenol have "down-the-drain" applications, such as laundry and dish soap, so the contaminants are frequently introduced into the water supply.
 n sewage treatment plants, nonylphenol ethoxylate degrades into nonylphenol, which is found in river water and sediments as well as soil and groundwater.

First aid measures
General information:
Immediately remove any clothing soiled by the product.
Symptoms of poisoning may occur even after several hours; therefore medical observation for at least 48 hours after the accident is recommended.
After inhalation: Supply fresh air; consult doctor in case of complaints.
After skin contact: Immediately wash with water and soap and rinse thoroughly.
Seek immediate medical advice.
·After eye contact: Rinse opened eye for several minutes under running water. 
Then consult a doctor.
After swallowing: Rinse mouth. 
Do not induce vomiting.
Seek medical treatment.

STORAGE
Store para-Nonylphenol in an area without drain or sewer access. 
para-Nonylphenol should be separated from strong oxidants and strong bases. 
Provision to contain effluent of para-Nonylphenol from fire extinguishing. 

PACKAGING
Marine pollutant. 

SPILLAGE DISPOSAL    
Personal protection: complete protective clothing.
Do NOT let this chemical enter the environment. 
Collect leaking and spilled liquid in sealable containers as far as possible. 
Absorb remaining liquid in sand or inert absorbent.
Then store para-Nonylphenol and dispose of according to local regulations. 

Sources and transportation pathways
There are no natural sources of nonylphenols and their ethoxylates in the environment. 
Wastewater treatment plants are an important source of nonylphenols to the aquatic environment. 
Some point source emissions may also occur, such as emissions from industries where these alkylphenols are used, and through leach water from landfills. 
Leakage from nonylphenol-containing products is another source of these substances.
Leakage from concrete structures via stormwater also contributes to the presence of nonylphenols in the environment. 
Concrete recycling including crushing may result in higher leaching of nonylphenols compared to existing structures.


Production
Nonylphenol can be produced industrially, naturally, and by the environmental degradation of alkylphenol ethoxylates. 
Industrially, nonylphenols are produced by the acid-catalyzed alkylation of phenol with a mixture of nonenes. 
This synthesis leads to a very complex mixture with diverse nonylphenols.
Nonylphenols are also produced naturally in the environment. One organism, the velvet worm, produces nonylphenol as a component of its defensive slime. 
The nonylphenol coats the ejection channel of the slime, stopping it from sticking to the organism when it is secreted. It also prolongs the drying process long enough for the slime to reach its target.
Another surfactant called nonoxynol, which was once used as intravaginal spermicide and condom lubricant, was found to metabolize into free nonylphenol when administered to lab animals.

Alternative Names
4-nonylphenol
4-n-Nonylphenol
104-40-5
p-Nonylphenol
Phenol, 4-nonyl-
para-Nonylphenol
p-n-Nonylphenol
4-nonyl phenol
Phenol, p-nonyl-
Phenol, nonyl derivs.
Nonylphenol (mixed)
para Nonyl phenol
p -n -Nonylphenol
p-nonyl phenol
4-Nonyl-Phenol
4-n-Nonyl phenol
DSSTox_GSID_33836
4-NP
CAS-104-40-5
C9-Alkylated phenol
CCRIS 1251
(C9)Alkylated phenol
1-(4-Hydroxyphenyl)nonane
nonyl-phenol
p-nonyl-phenol
Para-nonyl phenol

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