NONYL PHENOL 40 FLAKE

Synonyms:
Nonil fenol 40; Nonil fenol 40 etoksile; nonylphenol; nonylphenol 40 ; Nonil fenol 40 etoksile; Nonil fenol etoksile; Nonil fenol 40 etoksile; Nonyl phenol 40 40; polioksietilen; Nonyl phenol ethoxylate-40; Nonil fenol 40 EO; Nonil fenol ETHOXYLATE POE nonil Fenil Eter; Etoksile Nonil fenol; Polioksietilen nonilfenil eter; nonilfenil eter, polietilen glikol, noniyonik; makrogol nonilfenil eter; Polietilen Mono (nonilfenil) eter, Glikoller; polioksi etilen; polioxyetilen; poli-oksietilen; polioksi-etilen; polioksi,etilen; akropal; AKROPAL; Nonyl phenol ethoxylate-40; Nonyl phenol Ethoxylate 40; Nonyl phenol ethoxylate 40; Nonyl phenol Ethoxylate;Nonyl phenol 40; Ethoxylate;polyoxyethylene alkyl phenyl ether; alkyl phenyl polyoxyethylene ether;anti-was agent OP-1021; KONION NP-2; KONION NP-3; KONION NP-4; KONION NP-5; KONION NP-6; KONION NP-8; KONION NP-8.5; KONION NP-9; KONION NP-10; KONION NP-12; 20427-84-3, 2-[2-(4-nonylphenoxy)ethoxy]ethanol, 2-(2-(4-Nonylphenoxy)ethoxy)ethanol,; 2[2-(4-Nonylphenoxy)ethoxy]ethanol, 238635_ALDRICH, 238651_ALDRICH, 238678_ALDRICH, 26027-38-3, 9016-45-9, 9062-77-5, A 740, A 740 (surfactant), Adekatol NP, Adekatol NP 1000, Adekatol NP 1100, Adekatol NP 638, Adekatol NP 650,Adekatol NP 660, Adekatol NP 675, Adekatol NP 683,Adekatol NP 686, Adekatol NP 690, Adekatol NP 700, Adekatol NP 710, Adekatol NP 720, Adekatol NP 760, Adekatol NP 900, Afilan CVH, Agral, Agral 600, Agral 90, Agral LN, Agral Plus, Agral R, Akyporox NP 105, Akyporox NP 95, Alcosist PN, Alfenol, Alfenol 10, Alfenol 18, Alfenol 22, Alfenol 28, Alfenol 710, Alfenol 8, Alfenol N 8, Alkasurf NP, Alkasurf NP 11, Alkasurf NP 15, Alkasurf NP 8, alpha-(Nonylphenyl)-omega-hydroxypoly(oxy-1,2-ethanediyl),  alpha-(Nonylphenyl)-omega-hydroxypolyoxyethylene, Antarox 897, Antarox CO, Antarox CO 440, Antarox CO 540,  Antarox CO 640, Antarox CO 740, Antarox CO 850, Arkopal N-090, C19H32O3, Carsonon N-9, Caswell No. 605, Chemax NP series, Conco NI-90, DIETHYLENE GLYCOL P-NONYLPHENYL ETHER, Dowfax 9N20, EINECS 243-816-4, Emulgen - 913,EPA Pesticide Chemical Code 079005, Ethanol, 2-(2-(4-nonylphenoxy)ethoxy)-, Ethanol, 2-[2-(4-nonylphenoxy)ethoxy]-, Ethoxylated Nonyl phenol, Glycols, polyethylene, mono(nonylphenyl) ether, Glycols, polyethylene, monononylphenyl ether, Glycols,polyethylene mono(nonylphenyl) ether (nonionic), HSDB 6825, Igepal CO-210, Igepal CO-640, Igepal CO-720, Igepal CO-890, Lissapol NX, LS-118796, LS-15337, NCGC00164410-01, Neutronyx 600, Nonoxinolum [INN-Latin], Nonoxynol-3, Nonoxynol-40, Nonoxynol-4, Nonoxynol-44, Nonyl phenol, ethoxylated, Nonyl phenol,polyoxyethyleneether, Nonylphenoxy polyethoxyethanol, (Nonylphenoxy) polyethylene oxide, Nonylphenoxypoly(ethyleneoxy)ethanol, branched, Nonyl phenyl polyethylene glycol, Nonyl phenyl polyethylene glycol ether, omega-Hydroxy-alpha-(nonylphenyl)poly(oxy-1,2-ethanediyl), PEG-13 Nonyl phenyl ether, PEG-15 Nonyl phenyl ether, PEG-40 Nonyl phenyl ether, PEG-3 Nonyl phenyl ether, PEG-44 Nonyl phenyl ether, PEG-4 Nonyl phenyl ether, PEG-9 Nonyl phenyl ether, Polyethylene glycol (13) nonyl phenyl ether, Polyethylene glycol (15) nonyl phenyl ether, Polyethylene glycol 200 nonyl phenyl ether, Polyethylene glycol (40) nonyl phenyl ether, Polyethylene glycol (3) nonyl phenyl ether, Polyethylene glycol (44) nonyl phenyl ether, Polyethylene glycol 450 nonyl phenyl ether, POLYETHYLENE GLYCOL NONYLPHENYL ETHER, Poly(oxy-1,2-ethanediyl), alpha-(nonylphenyl)-omega-hydroxy-, Polyoxyethylene(10)nonylphenyl ether, Polyoxyethylene(12) nonylphenyl ether, branched, Polyoxyethylene (13) nonyl phenyl ether, Polyoxyethylene (15) nonyl phenyl ether, Polyoxyethylene(2) nonylphenyl ether, branched, Polyoxyethylene (40) nonyl phenyl ether, Polyoxyethylene(40) nonylphenyl ether, Polyoxyethylene (3) nonyl phenyl ether, Polyoxyethylene(40) nonylphenyl ether, branched, Polyoxyethylene (44) nonyl phenyl ether, Polyoxyethylene (4) nonyl phenyl ether, Polyoxyethylene (9) nonyl phenyl ether, Polyoxyethylene Nonyl phenol, Prevocel #12, Protachem 640, Rewopol HV-9, Synperonic NX, Tergetol NP, Tergitol NP-10, Tergitol NP-14, Tergitol NP-27, Tergitol NP-33 (nonionic), Tergitol NP-35 (nonionic), Tergitol NP-40 (nonionic),  Tergitol NPX, Tergitol TP-9 (nonionic), Triton N-100, Trycol NP-1,; 4-Nonyl phenol; p-Nonyl phenol; 4-n-Nonyl phenol; Phenol, 4-nonyl-; 104-40-5; para-Nonyl phenol; p-n-Nonyl phenol; Phenol, nonyl-; Phenol, p-nonyl-; 4-nonyl phenol; Nonyl phenol (mixed); Phenol, nonyl derivs.para Nonyl phenol; p -n -Nonyl phenol; CCRIS 1251; HSDB 5359; EINECS 203-199-4; BRN 2047450; CHEBI:34440IGFHQQFPSIBGKE-UHFFFAOYSA-N; MFCD00002396; SBB059316; DSSTox_CID_1857; DSSTox_RID_79098; DSSTox_GSID_33836; 68081-86-7; 4-NP; CAS-104-40-5; C9-Alkylated phenol; (C9)Alkylated phenol; UNII-I03GBV4WEL; p-nonyl phenol; Para-nonyl phenol; 4-Nonyl-Phenol; 4-n-Nonyl phenol;; EINECS 268-359-8; Spectrum_001973; SpecPlus_000624; AC1Q2VYR Spectrum2_001832; Spectrum3_000872; Spectrum4_000712; Spectrum5_002066; 4-n-Nonyl phenol, 85%; 4-n-Nonyl phenol, 98% I03GBV4WEL; 1-(4-Hydroxyphenyl)nonane; AC1L1C5R; AC1Q7A7Y; BIDD:PXR0002; SCHEMBL15887; BSPBio_002543; ER0006; DivK1c_006720; SPBio_001903; CHEMBL154062; DTXSID5033836; CTK0I0829; KBio1_001664; KBio2_002540; KBio2_005098; KBio2_007666KBio3_002043; MolPort-001-792-012; 4-Nonyl phenol, analytical standard; ZINC1850497; Tox21_201241;Tox21_403647; BDBM50410532; CCG-39613; LMPK15010001; LS-375; STL453644; AKOS015888197; MCULE-5940378829; P-Nonyl phenol (ENDOCRINE DISRUPTER); KB-193654; TL8000182; TR-000982; FT-0619310; ST50827096;C14550; 4-Nonyl phenol, PESTANAL(R), analytical standard; C-33468; J-001167; I01-10138; I14-50858 4-Nonyl phenol, certified reference material, TraceCERT(R); 4-Nonyl phenol (mixture of compounds with branched sidechain); 29832-11-9; polioksi etilen; polioxyetilen; poli oksi etilen; nonilphenol 40; nonylfenol 40; Nonil fenol 40; Nonil fenol etoksilat; Nonil fenoletoksilat; Nonil fenol40etoksilat; Np 40; Np-40; NP,40; NP 40; DETERGENT BIOGRAD FL-70 TERGITOL(TM) TMN-6; TERGITOL(TM) TMN-10; TERGITOL TMN-6; TERGITOL TMN; TERGITOL(TM) 15-S-9 TERGITOL(TM) 15-S-7; TERGITOL(TM) 15-S-5;127087-87-0 BioChemical DETERGENT BIOGRAD FL-70 TERGITOL(TM);TMN-6 TERGITOL(TM) TMN-10; TERGITOL TMN-6; TERGITOL TMN; TERGITOL(TM) 15-S-9; TERGITOL(TM) 15-S-7; TERGITOL(TM) 15-S-5;  TERGITOL(TM) 15-S-40;TERGITOL(TM) 15-S-40; TERGITOL(TM) 15-S-3; TERGITOL(R) TMN 6; TERGITOL(R) TMN 3; TERGITOL(R) 15-S-5; TERGITOL(R) TMN 10;TERGITOL TYPE 15-S-9; TERGITOL TYPE 15-S-7; TERGITOL TYPE 15-S-5; TERGITOL TYPE 15-S-40; TERGITOL TYPE 15-S-12;TERGITOL TYPE NP-7; TERGITOL TYPE NP-10; TERGITOL TYPE NP-9; POLYETHYLENE GLYCOL TRIMETHYLNONYL ETHER; Detergents Non-Ionic 2-ethanediyl),alpha-(4-nonylphenyl)-omega-hydroxy-poly(oxy-branched 2-ethanediyl) poly(oxy-alpha-(4-nonylphenyl)-omega-hydroxy-poly(oxy-branched alpha-(4-nonylphenyl)-omega-hydroxypoly(oxy-1,2-ethanediyl)- branched tergitolnp-4surfactant TERGITOL TYPE NP-4; TERGITOL NP-10; NONIONIC TERGITOL NP-7; NONIONIC TERGITOL TYPE NP-40 70% SOLUTION Np-15(Tergitol) Poly(oxy-1,2-ethanediyl),alpha.-(4-nonylphenyl)-.omega.-hydroxy-,branchedNONOXINOL10 ONYLPHENOLETHOXYLATEWITH NOLESOFETHYLENEOXIDE TERGITOLNP-4 polyethylene glycol mono-p-nonylphenyl ether, branched Detergents Detergents A to ZDetergents Non-Ionic Nonyl phenol polyethylene glycol ether, Triton(R) C9H19C6H4OCH2CH29OH; Polyethylene glycol mono(branched p-nonylphenyl) ether; 4-Nonyl phenol branched ethoxylated; Tergitol Tergitol(R) NP-4, Surfactant Tergitol(R) NP-40, Surfactant Tergitol(R) NP-7, Surfactant Tergitol(R) NP-9, Surfactant Tergitol 4-Nonyl phenol branched ethoxylated Tergitol[R]4-Nonyl phenol branched ethoxylated -(4-NONYLPHENYL)-OMEGA-HYDROXYPOLY-(OXY-1,2-ETHANEDIYL)-BRANCHED Poly(oxy-1,2-ethanediyl),a-(4-nonylphenyl)-w-hydroxy-, branched; Polyethylene glycol nonylphenyl ether;alpha-(Nonylphenyl)-omega-hydroxypoly(oxy-1,2-ethanediyl); Poly(oxy,1,2-ethanediyl) alpha-(4-nonylphenyl)-omega-hydroxy- branched;4-Nonyl phenol POLYETHYLENE GLYCOL ETHER BRANCHED; 4-Nonyl phenol, branched, ethoxylatedBRANCHED Nonyl phenol POLYETHYLENE GLYCOL ETHER; Nonyl phenol and its ethoxylates Poly(oxy-1,2-ethanediyl), ?-(4-nonylphenyl)-?-hydroxy-branched; Poly(oxy-1,2-ethanediyl), ?-(4-nonylphenyl)-?-hydroxy-, branched Poly(oxy-1,2-ethanediyl), ?-(4-nonylphenyl)-?-hydroxy-, branched; POLY(OXY-1,2-ETHANEDIYL), ?-?-HYDROXY-,BRANCHED?-(4-Nonylphenyl)-?-hydroxypoly(oxy-1,2-ethanediyl), branched; ?-(4-Nonylphenyl)-?-hydroxypoly(oxyethane-1,2-diyl) ramifie;4-Nonyl phenol, branched, ethoxylated; Poly(oxy,1,2-ethanediyl) alpha-(4-nonylphenyl)-omega-hydroxy- branched4-Nonyl phenol branched ethoxylated; NPE; NP 40; Nonil fenol 40; Nonil fenol 40 etoksile; Nonyl phenol ethoxylate; Cas No : 127087-87-0;Nonil fenol 40 EO; Polyoxyethylene Alkylphenyl Ether; arkopal; polyoxyethylene; NP 40; Nonyl phenol with 40 ethoxylate; Nonyl phenol ethoxylate- 40; Polyoxyethylene Alkylphenyl Ether; NP-40; NP40; NP/40; Nonil fenol40; nonil fenol 40; Nonil fenol etoksilat;  polioksietilen alkilfenil eter; polioksietilen; poli oksietilen; poli oksi etilen; polioksi etilen; NP 40, Nonil fenol 40, Nonil fenol 40 etoksile, Nonyl phenol ethoxylate, Cas No : 127087-87-0, Nonil fenol 40 EO, , Polyoxyethylene Alkylphenyl Ether, arkopal,polyoxyethylene; NP 40, Nonyl phenol with 40 ethoxylate, Nonyl phenol ethoxylate- 40; Polyoxyethylene Alkylphenyl Ether ;nonifenol; non i fenol; noni fenol; noniphenol; non i phenol; noni phenol; nonylfenol; nony fenol; nonyl fenol; Nonyl phenol; nonyl Phenol; nonil phenol; nonifenol40 ; non i fenol40; noni fenol40; noniphenol40; non i phenol40; noni phenol40; nonylfenol40; nony fenol40; nonyl fenol40; Nonyl phenol40; nonyl Phenol40; nonil phenol40;  nonifenol-40 ; non i fenol-40; noni fenol-40; noniphenol-40; non i phenol-40; noni phenol-40; nonylfenol-40; nony fenol-40; nonyl fenol-40; Nonyl phenol-40; nonyl Phenol-40; nonil phenol-40;  Nonil fenol; non il fenol; nonil fenol; nonilphenol; non il phenol; nonil phenol; nonylfenol; nony fenol; nonyl fenol; Les nonylphénols; nonylphénols Les Nonyl phenols;  nonylphénols; NONYL PHENOL 40 FLAKE; NONYL PHENOL 40; NONYL PHENOL-40; Np-40; NP 40; Nonilfenol 40; Nonilfenol

Nonyl phenol 40 

Nonyl phenol
Nonyl phenoles V.svg
Names
IUPAC name
4-(2,4-dimethylheptan-3-yl)phenol
Other names
Phenol, nonyl-
Identifiers
CAS Number
25154-52-3 General class ☑
104-40-5 4-n-Nonyl phenol ☒
84852-15-3 Branched 4-Nonyl phenols ☒
11066-49-2 IsoNonyl phenols ☒
3D model (JSmol)
Interactive image
ChEMBL    
ChEMBL154062 ☒
ChemSpider    
60628 ☑
PubChem CID
67296
InChI[show]
SMILES[show]
Properties
Chemical formula
C15H24O
Molar mass    220.35 g/mol
Appearance    Light yellow viscous liquid with phenolic smell [1]
Density    0.953
Melting point    −8 to 2 °C (18 to 36 °F; 265 to 275 K)
Boiling point    293 to 297 °C (559 to 567 °F; 566 to 570 K)
Solubility in water
6 mg/L (pH 7)
Hazards
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).
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Infobox references
Nonyl phenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. Nonyl phenols can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers.[2] These compounds are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and Nonyl phenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. Nonyl phenol 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.[3] The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain.[4][5][6] Nonyl phenol has been found to act as an agonist of the GPER (GPR40).[7]

Structure and basic properties
Nonyl phenols fall into the general chemical category of alkylphenols.[8] The structure of Nonyl phenols 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 Nonyl phenol, 4-Nonyl phenol, is the most widely produced and marketed Nonyl phenol.[9] The mixture of Nonyl phenol isomers is a pale yellow liquid, although the pure compounds are colorless. The Nonyl phenols are moderately soluble in water [9] but soluble in alcohol.

Nonyl phenol arises from the environmental degradation of Nonyl phenol ethoxylates, which are the metabolites of commercial detergents called alkylphenol ethoxylates. Nonyl phenols are a clear to light orange color liquid. Nonyl phenol ethoxylates are nonionic in water, which means that they have no charge. Because of this property they are used as detergents, cleaners, emulsifiers, and a variety of other applications. They are amphipathic, meaning they have both hydrophilic and hydrophobic properties, which allows them to surround non-polar substances like oil and grease, isolating them from water.[2]

Production
Nonyl phenol can be produced industrially, naturally, and by the environmental degradation of alkylphenol ethoxylates. Industrially, Nonyl phenols are produced by the acid-catalyzed alkylation of phenol with a mixture of nonenes. This synthesis leads to a very complex mixture with diverse Nonyl phenols.[10][11][12] Theoretically there are 211 constitutional isomers and this number rise to 550 isomers if we take the enantiomers into account.[4] To make Nonyl phenols, manufacturers treat Nonyl phenol 40 with ethylene oxide under basic conditions.[9] Since its discovery in 1940, Nonyl phenol production has increased exponentially, and between 100 and 500 million pounds of Nonyl phenol are produced globally every year,[9][13] meeting the definition of High Production Volume Chemicals.

Nonyl phenols are also produced naturally in the environment. One organism, the velvet worm, produces Nonyl phenol as a component of its defensive slime. The Nonyl phenol 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.[14]

Another surfactant called nonoxynol, which was once used as intravaginal spermicide and condom lubricant, was found to metabolize into free Nonyl phenol when administered to lab animals.[8]

Applications
Nonyl phenol is used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers.[2] It 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 Nonyl phenol are also used as heat stabilizers for polyvinyl chloride (PVC).[15] Nonyl phenol is also often used an intermediate in the manufacture of the non-ionic surfactants Nonyl phenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. Nonyl phenol and Nonyl phenol ethoxylates are only used as components of household detergents outside of Europe.[2] Nonyl Phenol, is used in many epoxy formulations mainly in North America.

Prevalence in the environment
Nonyl phenol persists in aquatic environments and is moderately bioaccumulative. Nonyl phenol is not readily biodegradable, and it can take months or longer to degrade in surface waters, soils, and sediments. Nonbiological degradation is negligible.[3] Nonyl phenol is partially removed during municipal wastewater treatment due to sorption to suspended solids and biotransformation. [16] [17] Many products that contain Nonyl phenol have "down-the-drain" applications, such as laundry and dish soap, so the contaminants are frequently introduced into the water supply. In sewage treatment plants, Nonyl phenol ethoxylate degrades into Nonyl phenol, which is found in river water and sediments as well as soil and groundwater.[18] Nonyl phenol photodegrades in sunlight, but its half-life in sediment is estimated to be more than 60 years. Although the concentration of Nonyl phenol in the environment is decreasing, it is still found at concentrations of 4.1 μg/L in river waters and 1 mg/kg in sediments.[2]

A major concern is that contaminated sewage sludge is frequently recycled onto agricultural land. The degradation of Nonyl phenol in soil depends on oxygen availability and other components in the soil. Mobility of Nonyl phenol in soil is low.[2]

Bioaccumulation is significant in water-dwelling organisms and birds, and Nonyl phenol has been found in internal organs of certain animals at concentrations of 10 to 1,000 times greater than the surrounding environment.[3] Due to this bioaccumulation and persistence of Nonyl phenol, it has been suggested that Nonyl phenol could be transported over long distances and have a global reach that stretches far from the site of contamination.[19]

Nonyl phenol is not persistent in air, as it is rapidly degraded by hydroxyl radicals.[3]

Environmental hazards
Nonyl phenol is considered to be an endocrine disruptor due to its ability to mimic estrogen and in turn disrupt the natural balance of hormones in affected organisms.[4][5][6][20][21] The effect is weak because Nonyl phenols are not very close structural mimics of estradiol, but the levels of Nonyl phenol can be sufficiently high to compensate.

Structure of the hormone estradiol and one of the Nonyl phenols.
The effects of Nonyl phenol in the environment are most applicable to aquatic species. Nonyl phenol can cause endocrine disruption in fish by interacting with estrogen receptors and androgen receptors. Studies report that Nonyl phenol competitively displaces estrogen from its receptor site in rainbow trout.[22] It has much less affinity for the estrogen receptor than estrogen in trout (5 x 10-5 relative binding affinity compared to estradiol) making it 100,000 times less potent than estradiol.[22][23] Nonyl phenol causes the feminization of aquatic organisms, decreases male fertility, and decreases survival in young fish.[2] Studies show that male fish exposed to Nonyl phenol have lower testicular weight.[22] Nonyl phenol can disrupt steroidogenesis in the liver. One function of endogenous estrogen in fish is to stimulate the liver to make vitellogenin, which is a phospholipoprotein.[22] Vitellogenin is released by the maturing female and sequestered by developing oocytes to produce the egg yolk.[22] Males do not normally produce vitellogenin, but when exposed to Nonyl phenol they produce similar levels of vitellogenin to females.[22] The concentration needed to induce vitellogenin production in fish is 10 ug/L for Nonyl phenol 40 in water.[22] Nonyl phenol can also interfere with the level of FSH (follicle-stimulating hormone) being released from the pituitary gland. Concentrations of Nonyl phenol 40 that inhibit reproductive development and function in fish also damages kidneys, decreases body weight, and induces stressed behavior.[24]

Human health hazards
Alkylphenols like Nonyl phenol and bisphenol A have estrogenic effects in the body. They are known as xenoestrogens.[25] 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 against natural estrogens. Nonyl phenol has been shown to mimic the natural hormone 17β-estradiol, and it competes with the endogeous hormone for binding with the estrogen receptors ERα and ERβ.[2] Nonyl phenol was discovered to have hormone-like effects by accident because it contaminated other experiments in laboratories that were studying natural estrogens that were using polystyrene tubes.[8]

Effects in pregnant women
Subcutaneous injections of Nonyl phenol in late pregnancy causes the expression of certain placental and uterine proteins, namely CaBP-9k, which suggest it can be transferred through the placenta to the fetus. It has also been shown to have a higher potency on the first trimester placenta than the endogenous estrogen 17β-estradiol. In addition, early prenatal exposure to low doses of Nonyl phenol cause an increase in apoptosis (programmed cell death) in placental cells. These “low doses” ranged from 10−13-10−9 M, which is lower than what is generally found in the environment.[26]

Nonyl phenol has also been shown to affect cytokine signaling molecule secretions in the human placenta. In vitro cell cultures of human placenta during the first trimester were treated with Nonyl phenol, which increase the secretion of cytokines including interferon gamma, interleukin 4, and interleukin 10, and reduced the secretion of tumor necrosis factor alpha. This unbalanced cytokine profile at this part of pregnancy has been documented to result in implantation failure, pregnancy loss, and other complications.[26]

Regulation
The production and use of Nonyl phenol and Nonyl phenol ethoxylates is prohibited in the European Union due to its effects on health and the environment.[2][44] In Europe, due to environmental concerns, they also have been replaced by more expensive alcohol ethoxylates, which are less problematic for the environment due to their ability to degrade more quickly than Nonyl phenols. The European Union has also included Nonyl phenol 40 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 Nonyl phenol 40 was proposed to be 0.3 ug/l.[2] In 2013 Nonyl phenols were registered on the REACH candidate list.

In the US, the EPA set criteria which recommends that Nonyl phenol concentration should not exceed 6.6 ug/l in fresh water and 1.7 ug/l in saltwater.[45] In order to do so, the EPA is supporting and encouraging a voluntary phase-out of Nonyl phenol in industrial laundry detergents. Similarly, the EPA is documenting proposals for a "significant new use" rule, which would require companies to contact the EPA if they decided to add Nonyl phenol to any new cleaning and detergent products. They also plan to do more risk assessments to ascertain the effects of Nonyl phenol on human health and the environment. It was suggested that Nonyl phenol could be added to the list of chemicals on the Toxic Substances Control Act of 1976, but this has yet to occur as of 2014.[3]

In other Asian and South American countries Nonyl phenol is still widely available in commercial detergents, and there is little regulation.[45]

4-Nonyl phenol is a member of the class of phenols that is phenol which is para-substituted with a nonyl group. It has a role as an environmental contaminant.

ChEBI
Environmental pollutant arising from the degradation of nonionic surfactants in sewage Nonoxynol-9, one of the APEs, is used as a surfactant in cleaning and cosmetic products, and as a spermicide in contraceptives. Nonyl phenol is an organic compound of the wider family of alkylphenols. It 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, Nonyl phenols are classified as xenobiotics. In Nonyl phenols, a hydrocarbon chain of nine carbon atoms is attached to the phenol ring in either the ortho (2), meta (3), or para (4) position, with the most common ring isomers being ortho or para (e. g. figure 1 para-Nonyl phenol). Moreover, the alkyl chains can exist as either linear n-alkyl chains, or complex branched chains. Nonyl phenol 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 Nonyl phenol crystallize readily at room temperatures and for example, para-n-Nonyl phenol, forms white crystals at room temperature. Nonyl phenol, 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 Nonyl phenol as it is probably reactive with atmospheric radicals and/or is photoactive.

Human Metabolome Database (HMDB)

Nonyl phenol is a toxic xenobiotic compound classified as an endocrine disrupter capable of interfering with the hormonal system of numerous organisms. It originates principally from the degradation of Nonyl phenol ethoxylates which are widely used as industrial surfactants. Nonyl phenol ethoxylates reach sewage treatment works in substantial quantities where they biodegrade into several by-products including Nonyl phenol. Due to its physical–chemical characteristics, such as low solubility and high hydrophobicity, Nonyl phenol accumulates in environmental compartments that are characterised by high organic content, typically sewage sludge and river sediments, where it persists. The occurrence of Nonyl phenol in the environment is clearly correlated with anthropogenic activities such as wastewater treatment, landfilling and sewage sludge recycling. Nonyl phenol is found often in matrices such as sewage sludge, effluents from sewage treatment works, river water and sediments, soil and groundwater. The impacts of Nonyl phenol in the environment include feminization of aquatic organisms, decrease in male fertility and the survival of juveniles at concentrations as low as 8.2 μg/l. Due to the harmful effects of the degradation products of Nonyl phenol ethoxylates in the environment, the use and production of such compounds have been banned in EU countries and strictly monitored in many other countries such as Canada and Japan. Although it has been shown that the concentration of Nonyl phenol in the environment is decreasing, it is still found at concentrations of 4.1 μg/l in river waters and 1 mg/kg in sediments. Nonyl phenol has been referred to in the list of priority substances in the Water Frame Directive and in the 3rd draft Working Document on Sludge of the EU. Consequently there is currently a concern within some industries about the possibility of future regulations that may impose the removal of trace contaminants from contaminated effluents. The significance of upgrading sewage treatment works with advanced treatment technologies for removal of trace contaminants is discussed.
Nonyl phenol
Nonyl phenol (NP) is a subset of the alkylphenol, and is used as an intermediate in the production of non-ionic surfactants of Nonyl phenol ethoxylate.
Nonyl phenol
Shinichi Miyagawa, ... Taisen Iguchi, in Handbook of Hormones, 2016

Environment
In the environment, Nonyl phenol 40 originates from degradation of Nonyl phenol ethoxylates, and the principal source is treated wastewater effluent [3,4]. Sumpter and Jobling suggested that Nonyl phenol 40 contained in effluent from sewage treatment works is associated with vitellogenesis in male rainbow trout [5]. Nonyl phenol 40 has greater binding affinity for fish ER than for human ER, and induces the formation of testis–ova (oocytes in the testis) of Japanese medaka at environmentally relevant concentrations [6]. In vitro reporter gene assay revealed that relative potency of Nonyl phenol 40 to estradiol-17β for medaka estrogen receptor α is 0.5% [7]. In in vivo experiments, Nonyl phenol was found to induce vitellogenins (female egg yolk proteins) in the male liver at 20.3 μg/l in rainbow trout, and at 11.6 μg/l in medaka [8,9].

Q1. What are Nonyl phenols?
Nonyl phenols, also known as Nonyl phenols and Nonyl phenol ethoxylates, are nonionic surfactants, or detergent-like substances, with uses that lead to widespread release into aquatic environments. Nonyl phenols are highly toxic to aquatic life. Note: EPA’s September 2014 proposed Significant New Use Rule covers only Nonyl phenols that are no longer being used in manufacturing or in products; the SNUR would give EPA the opportunity to review new or resumed use of these 15 Nonyl phenols.

Q2. How are Nonyl phenols used?
NPs/Nonyl phenols, which are produced in large volumes, are used for industrial processes and in consumer laundry detergents, personal hygiene, automotive, latex paints, and lawn care products.

Q3. What action is EPA taking?
EPA is proposing a Significant New Use Rule, also known as a SNUR, under the Toxic Substances Control Act (TSCA). The rule would require manufacturers to provide at least 90 days notice to EPA before commencing or resuming any significant new use of the 15 Nonyl phenols that are no longer used in commerce. This would give EPA the opportunity to evaluate the intended use and, if warranted, take action to prohibit or limit the activity before it occurs.

Q4. Why is EPA proposing a SNUR for Nonyl phenols?
Nonyl phenols chemicals are highly toxic to aquatic life and have a wide variety of industrial and consumer uses that could lead to environmental releases. This action is part of EPA’s work to ensure chemical safety in order to protect human health and the environment.

Q5. How many chemicals are in the proposed SNUR?
There are 15 Nonyl phenols chemicals in this proposed SNUR; four Nonyl phenolss and 11 Nonyl phenols.

Q6. What are the potential risks to people?
Nonyl phenols has been detected in human breast milk, blood, and urine and is associated with reproductive and developmental effects in rodents.

Q7. Is there an easy way for consumers to avoid using products with Nonyl phenols?
Consumers can avoid products with Nonyl phenols by looking for products with EPA’s Safer Choice Label on the shelves of major retailers. When you see the safer product label on a product it means that EPA scientists have evaluated every ingredient in the product to ensure it meets stringent human health and environmental criteria. Learn more about consumer products that carry the safer product label at:http://www2.epa.gov/saferchoice/learn-about-safer-choice-label.

Q8. Are there alternatives to Nonyl phenols?
As part of its Safer Product Labeling Program, Design for the Environment has evaluated hundreds of surfactants. Design for the Environment has posted almost 200 non-Nonyl phenols safer surfactants on its Safer Chemical Ingredient List (SCIL) available at http://www2.epa.gov/saferchoice/safer-ingredients.

Q9. What other action is EPA taking to evaluate the potential risks of Nonyl phenols?
In 2010, under EPA’s Design for the Environment Safer Detergents Stewardship Initiative (SDSI), the Textile Rental Services Association of America and its members achieved a 50 percent phase out of Nonyl phenols from the industrial laundry detergents market. In May 2012, a Design for the Environment Program Alternatives Assessment identified eight classes of surfactants that are safer alternatives to Nonyl phenols in a broad range of uses.

ABSTRACT Nonyl phenol is a toxic xenobiotic compound resulted from biodegradation of Nonyl phenol ethoxlates and alkyl phenol ethoxylates, and Nonyl phenol is considered to be an endocrine disrupter capable of interfering with the hormonal system of numerous organisms. Because of Nonyl phenols toxic nature, Nonyl phenol is on the 'priority list' of EPA and the European Water Framework Directive. Ever since Nonyl phenol was first synthesized, Nonyl phenols use and production have been increasing almost exponentially. NNonyl phenol has been used as wide range number of fields (textile, leather, paper, cleaning and cosmetics etc.). The annual production of Nonyl phenol reached to 73,500 tons in Europe, 40,000 tons in Japan and 145,000 tons in USA. The major source of Nonyl phenol in the environment is the discharge of effluents from sewage treatment plants. Low concentrations of Nonyl phenol 40 can cause damage in the skeletal system, and high concerations can inhibit the growth of embryos. In Europe and the World in 2020, Nonyl phenol will be planned that NPEO and APE will enter to the list of the priority chemicals, and also researches are conducted aiming to prevent the introduction of these harmful chemicals into the water environment.Nonyl phenols accumulate in the sediments and biological sewage sludges because of their amphiphilic natures. Nonyl phenol is determenied that NPs could be removed by several treatment methods such as aerobic, anaerobic, UV, ozonation, activated carbon and aerobic composting. However, these methods are expensive and cause to increase CO2 emission. Therefore, in order to remove Nonyl phenols which are of great importance in terms of environment and human health, Nonyl phenol should be considered to new treatment methods for these type of trace contaminants.

NPEs (Nonyl phenol ethoxylates) break down in the environment into Nonyl phenol (NP), one of the most notorious examples of persistent, bioaccumulative and toxic chemicals (PBTs). Widely recognized for extreme aquatic toxicity to fish and wildlife, Nonyl phenol ethoxylates and Nonyl phenol  may also threaten the health of the developing fetus and young children. Despite being phased out of laundry detergents, widespread use in other consumer products routinely releases NPEs into our homes and the environment.

Potential health effects include:

Hormone (endocrine) disruption
Extreme aquatic toxicity
Skin and eye irritation
Reproductive harm
Birth defects
Persistent and bioaccumulative
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-Nonyl phenol)
Consumer tips:

Nonyl phenol s are rarely listed as an ingredient on a product label. Since Nonyl phenol s are widely used in large amounts in virtually all household paints, you should ask paint manufacturers to reformulate with safer alternatives.

Wash new clothes before you wear them to reduce exposure to Nonyl phenol s in your home. (Nonyl phenols still need to be phased out of textile processing to protect the environment).

Reduce reliance on toys and games that use synthetic rubber, plastics and foams. Search the State of Washington database for specific children’s products that contain Nonyl phenol .

Urge Gap Inc. and other members of the footwear and apparel industry coalition to achieve their goal of zero discharge of hazardous chemicals, including NPEs, by 2020.

Don’t use pesticides inside your home. Avoid buying food packaged in plastics whenever practicable.

* Under our weak federal laws, it’s impossible for us to know all the uses of Nonyl phenol  in consumer products. As a result, this is not an exhaustive list of all products containing Nonyl phenol s.

Overview of Nonyl phenol 40 40;

Nonyl phenol (NP) and Nonyl phenol Ethoxylates (NPE) are the most widely used members of the larger alkylphenol and alkylphenol ethoxylate family of non-ionic surfactants. They are produced in large volumes, with uses that lead to widespread release to the aquatic environment.

Nonyl phenol is persistent in the aquatic environment, moderately bioaccumulative, and extremely toxic to aquatic organisms. NP's main use is in the manufacture of NPEs. NPEs are used in a wide variety of industrial applications and consumer products. NPEs, though less toxic than NP, are also highly toxic to aquatic organisms, and in the environment degrade to more environmentally persistent NP. Nonyl phenol 40 has also been detected in human breast milk, blood, and urine and is associated with reproductive and developmental effects in fish.

Nonyl phenols were once commonly used in household laundry detergents. EPA and the detergent manufacturers have cooperated to eliminate this use. However, NPEs are still widely used in large quantities in industrial laundry detergents and have some additional uses that lead to releases to water.