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4-Nonylphenol diethoxylate

HCID 24773
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
20427-84-3
Standard SMILES
CCCCCCCCCc1ccc(OCCOCCO)cc1
InChIKey
BLXVTZPGEOGTGG-UHFFFAOYSA-N
Molecular formula
C19H32O3
Average molar mass
308.5 g/mol
Monoisotopic mass
308.23514488

Overview

The CIR Expert Panel concluded that the following 27 Nonoxynols listed below are safe in the present practices of use and concentration in cosmetics as described in this safety assessment, when formulated to be non-irritating..Nonoxynol-2...

Names & identifiers

Preferred name
4-Nonylphenol diethoxylate
IUPAC
2-[2-(4-nonylphenoxy)ethoxy]ethanol
English name
Nonylphenol Ethoxylate
Molecular formula
C19H32O3
Molecular weight
308.45558

Names & synonyms

20427-84-34-Nonylphenol diethoxylateNonoxynol-2U4A966MO25DTXSID9058600RefChem:1071320DTXCID0016588243-816-42-[2-(4-Nonylphenoxy)ethoxy]ethanol9016-45-94-Nonyl Phenol Diethoxylate2-(2-(4-Nonylphenoxy)ethoxy)ethanol
Show more names
TX-10Ethoxylated nonylphenolNP 40ethyleneoxyNonylphenol polyoxyethylene etherNonoxynolsTX-9TX-21NonoxinolNonylphenoxypoly(ethyleneoxy)ethanol
2-[2-(4-nonylphenoxy)ethoxy]ethan-1-olEthanol, 2-(2-(4-nonylphenoxy)ethoxy)-CHEMBL194034MFCD00148006Polyoxyethylene (12) nonylphenyl etherEthanol, 2-[2-(4-nonylphenoxy)ethoxy]-DSSTox_CID_16588DSSTox_RID_79288

Database identifiers

CAS
20427-84-3、9016-45-9
PubChem CID
24773
DTXSID
DTXSID9058600

Properties

Computed structural properties

XLogP
5.6
Topological polar surface area
38.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
14
Heavy atoms
22
Formal charge
0
Complexity
225

Experimental & physicochemical properties

Chemical ClassesWaste-water effluent contaminant
PolymersOther Classes -> Polyoxyethylenes
Cosmetics · 3 items

Cosmetics ingredient -> Surfactant

Cosmetic ingredients (Nonoxynol-2) -> CIR (Cosmetic Ingredient Review)

Emulsifying; Cleansing; Surfactant

FragrancesFragrance Ingredient (Poly(oxy-1,2-ethanedyl), alpha-(nonylphenyl)-omega-hydroxy-) -> IFRA transparency List
SurfactantsSurfactant -> linear alkylbenzyl sulfonate (LAS)
Solubility>1000 mg/l
Endocrine DisruptorsPotential endocrine disrupting compound
DecompositionWhen heated to decomposition it emits acrid smoke and fumes.
Melting Point42-43 °C
Food Contact Substances

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

Hazard information

Regulatory Information · 6 items

Chemical: Poly(oxy-1,2-ethanediyl), .alpha.-(nonylphenyl)-.omega.-hydroxy-

Hazard Traits - Endocrine Toxicity

Poly(oxy-1,2-ethanediyl), .alpha.-(nonylphenyl)-.omega.-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Poly(oxy-1,2-ethanediyl), .alpha.-(nonylphenyl)-.omega.-hydroxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

FRI - indicates a polymeric substance containing no free-radical initiator in its Inventory name but is considered to cover the designated polymer made with any free-radical initiator regardless of the amount used.

SP - indicates a substance that is identified in a proposed Significant New Use Rule.

Substance: 2-[2-(4-nonylphenoxy)ethoxy]ethanol

Other Safety InformationIMAP assessments - Nonylphenol and octylphenol ethoxylates and related compounds: Human health tier II assessment
Hazards SummaryA skin and eye irritant; [CAMEO] An irritant; A severe eye irritant; [MSDSonline]
TSCA Requirements · 1 item

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 2/10/00; Reporting date: 4/10/00.

Chemistry & industry

Uses & manufacturing

Uses · 6 items

CIR ingredient: Nonoxynol-2

Used as surfactant; [HSDB] Used as non-ionic surfactant, emulsifier, and metal cleaner; Uses depend on the degree of polymerization; [CAMEO] Use as industrial chemical severely restricted in the EU; [eChemPortal: ESIS] Polyethylene glycol nonylphenyl ether is a mixture of polymers with varying chain lengths. The polymeric content is generally greater than 98%. [CHEMINFO]

For nonylphenoxypolyethoxyethanol (USEPA/OPP Pesticide Code: 079005) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Additive to metal cleaners as a dispersing agent ... Used in automatic toilet tank dispensers placed directly in the tank to lower surface tension and color the water used for flushing

Surfactant

U.S. Production · 4 items

2023: 400,000 - <550,000 lb

Poly(oxy-1,2-ethanediyl), .alpha.-(nonylphenyl)-.omega.-hydroxy- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#6317]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Poly(oxy-1,2-ethanediyl), .alpha.-(nonylphenyl)-.omega.-hydroxy-. Aggregated National Production Volume: 10 to < 50 million lbs.

Consumer UsesLubricating agent
Industry UsesNot Known or Reasonably Ascertainable
Household Products · 2 items

Cosmetics product ingredient: Nonylphenolethoxylate (Nonylphenol, ethoxylated)

Information on 104 consumer products that contain Nonylphenyl polyethylene glycol ether (mixture) in the following categories is provided:

Related reactions

1 records
New reaction record
HRID 2285623 reaction equation
HRID 2285623As reactantuspto-grants-1982_04

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
ChEMBL
CHEMBL194034
UNII
U4A966MO25
EC Number
243-816-4
Nikkaji
J235.963D
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description · 2 items

Liquid; Other Solid; CBI

Colorless liquid or white solid; [CAMEO] White or pale yellow solid; Hygroscopic (n >= 15; avg 15-100); Clear colorless or pale yellow liquid; Hygroscopic (n >= 5; avg 3-15); (n = avg # moles of ethylene oxide); [CHEMINFO]

Physicochemical properties

Melting point
44 · 44-46 °C
Boiling point
250 °C · 250 °C(lit.)
Density
1.06 g/mL · 1.06 g/mL at 20 °C
vapor pressure
1.4 hPa · 1.4hPa at 25℃
refractive index
20 · n20/D 1.495(lit.)
Flash point
535 °F · 535 °F
storage temp.
-20 °C · -20°C
form
Clear, colorless liquid
color
clear colorless
PH
5 · 5-8 (5% in H2O)
biological source
rabbit
Viscosity
350 · 350-450mPa.s(20°C)
Water Solubility
25 mg/mLaqueous · water: 25mg/mLaqueous buffer: soluble
Specific Activity
613 · 613-829nmol/min·mg
Cosmetics Ingredients Functions
SURFACTANT - SOLUBILIZINGSURFACTANT - EMULSIFYINGSURFACTANT - CLEANSING
Cosmetic Ingredient Review (CIR)
Nonylphenol Ethoxylate (9016-45-9)
InChI
InChI=1S/C19H32O3/c1-2-3-4-5-6-7-8-9-18-10-12-19(13-11-18)22-17-16-21-15-14-20/h10-13,20H,2-9,14-17H2,1H3
InChIKey
BLXVTZPGEOGTGG-UHFFFAOYSA-N
SMILES
C(O)COCCOC1=CC=C(CCCCCCCCC)C=C1
LogP
3.7 · 3.7-4.48 at 25℃
Surface tension
32.3 mN/m · 32.3mN/m at 1g/L and 20℃
Substances of Very High Concern (SVHC) Candidate List
Nonylphenol, ethoxylated (9016-45-9)
REACH Annex XVII Substances List
Nonylphenol, ethoxylated (9016-45-9)
FDA 21 CFR
177.1632 · 177.1632
Indirect Additives used in Food Contact Substances
POLY(OXYETHYLENE) MONO(NONYLPHENYL) ETHER
CAS DataBase Reference
9016 · 9016-45-9
EWG's Food Scores
2 · 2-4
FDA UNII
6 FW840C8W9 · 6FW840C8W9
EPA Substance Registry System
Polyethylene glycol nonylphenyl ether (9016-45-9)
UNSPSC Code
12352300 · 12352300
NACRES
41 · NA.41
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
315 · H315-H319-H412
Precautionary statements
273 · P273-P302+P352-P305+P351+P338
Hazard Codes
Xi,N,Xn
Risk Statements
41 · 41-38-37-36/37/38-50-22
Safety Statements
26 · 26-39-36-61
RIDADR
3082 · UN 3082 9 / PGIII
WGK Germany
2 · 2
RTECS
4750000 · WZ4750000
F
3 · 3
TSCA
TSCA listed
HS Code
34021300 · 34021300
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
2 Eye · Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2
Hazardous Substances Data
9016 · 9016-45-9(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 2590uL/kg
REACH Registrations
Inactive
FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Nonylphenoxypolyethoxyethanol is found on List C. Case No: 3118; Pesticide type: Insecticide, antimicrobial; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Nonylphenoxypolyethoxyethanol; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Hazard Classes and Categories · 5 items

Skin Irrit. 2 (100%)

Acute toxicity - category 4

Specific target organ toxicity - Repeated exposure - Category 2 (cardiovascular system)

Skin corrosion/irritation - Category 2

Skin corrosion/irritation - Category 2

Safety & protection

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Protective Action Criteria (PAC) · 3 items

3.9 [mg/m3]

43 [mg/m3]

260 [mg/m3]

Toxicology

Ecotoxicity Values · 5 items

LC50; Species: Pseudokirchneriella subcapitata (Green Algae); Conditions: freshwater, renewal, 25 °C, hardness 150 mg/L CaCO3; Concentration: 12000 ug/L for 96 hr

EC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, renewal, 25 °C, hardness 150 mg/L CaCO3; Concentration: 14000 ug/L for 48 hr (95% confidence interval: 13000-16000 ug/L); Endpoint: immobilization.

LC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, renewal, 25 °C, hardness 150 mg/L CaCO3; Concentration: 9000 ug/L for 144 hr

LC50; Species: Hyalella azteca (Scud) age 10-12 days; Conditions: freshwater, static, 25 °C, 7.4-8.1, dissolved oxygen 6.3-8.2 mg/L CaCO3; Concentration: ~1000 ug/L for 96 hr

For more Ecotoxicity Values (Complete) data for POLYETHYLENE GLYCOL NONYLPHENYL ETHER (18 total), please visit the HSDB record page.

Environmental Fate · 5 items

TERRESTRIAL FATE: Polyethylene glycol nonylphenyl ether is a mixture of compounds with varying ethoxylate units and branching on the alkyl portion of the molecule. Nonylphenol and mono- and diethoxylate nonylphenol are expected to adsorb to suspended solids and sediment in water(SRC) based on sludge adsorption tests(1,2); higher oligomers should not adsorb to sediment(1,2). Therefore, polyethyleneglycol nonylphenol ether is expected to have moderate mobility in soil(SRC). Volatilization of polyethyleneglycol nonylphenol ether from moist soil surfaces is not expected to be an important fate process(SRC) based on a range of Henry's Law constants from 2.45X10-9 atm-cu m/mole for nonylphenol (a measured value)(3) to 4.1X10-12 atm-cu m/mole for nonylphenol ethoxylate (n=6), developed using a fragment constant estimation method(4). Polyethyleneglycol nonylphenol ether is not expected to volatilize from dry soil surfaces(SRC) based upon vapor pressures ranging from extrapolated 9.4X10-5 mm Hg(5) to estimated 3.2X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(6).

TERRESTRIAL FATE: Aerobic biodegradation screening studies of polyethylene glycol linear nonylphenyl ethers with sewage sludge inocula indicate rapid primary degradation to nonylphenol diethoxylate and nonylphenol ethoxylate (68% to 91% degradation in 8-21 days)(1-2). Biodegradation screening studies on the aerobic biodegradation of mixtures of branched and linear polyethylene glycol nonylphenyl ethers indicate rapid primary degradation to nonylphenol diethoxylate and nonylphenol ethoxylate under aerobic conditions and nonylphenol under anaerobic conditions(3-5). These studies suggest that if released to soil, biodegradation of linear nonyl substituted polyethylene glycol nonylphenyl ethers may be an important fate process(SRC).

AQUATIC FATE: Polyethylene glycol nonylphenyl ether is a mixture of compounds with varying ethoxylate units and branching on the alkyl portion of the molecule. Nonylphenol and mono- and diethoxylate nonylphenol are expected to adsorb to suspended solids and sediment in water(SRC) based on sludge adsorption tests(1,2); higher oligomers should not adsorb to sediment(1,2). Volatilization from water surfaces is not expected(3) based on a range of Henry's Law constants from 2.45X10-9 atm-cu m/mole for nonylphenol (a measured value)(4) to 4.1X10-12 atm-cu m/mole for nonylphenol ethoxylate (n=6), developed using a fragment constant estimation method(5). According to a classification scheme(5), BCF values of <0.2 to <1.4, measured in carp(6), indicate that bioconcentration of polyethylene glycol nonylphenol ether in aquatic organisms is low(SRC). Bioconcentration of the more lipophylic esters such as nonylphenol and mono- and diethoxylate nonylphenol may be higher(7). Under conditions simulating a river water environment downstream from a wastewater treatment plant, over 40% of the 14C ring-labeled polyethylene glycol nonylphenyl ether was converted to 14CO2 in 128 days (overall biodegradation of 87-97%)(8), suggesting that biodegradation may be an environmental fate process in acclimated aquatic systems(SRC).

AQUATIC FATE: Primary biodegradation tests with sediment and river water(1,2), indicate that primary degradation of polyethylene glycol linear nonylphenyl ether in water will be important (97% to 99% in 30 days). Biodegradation screening studies on the aerobic biodegradation of mixtures of branched and linear polyethylene glycol nonylphenyl ethers indicate rapid primary degradation to nonylphenol diethoxylate and nonylphenol ethoxylate under aerobic conditions and nonylphenol under anaerobic conditions(3-5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), polyethyleneglycol nonylphenol ethers, which have vapor pressures ranging from extrapolated 9.4X10-5 mm Hg(2) to estimated 3.2X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(3), will exist mainly in the particulate phase in the ambient atmosphere, although some of the smaller oligomers may also exist in the vapor phase. Those compounds found in the vapor phase are expected to be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC). Particulate-phase polyethylene glycol nonylphenyl ethers may be physically removed from the air by both wet and dry deposition(SRC). polyethyleneglycol nonylphenol ethers do not contain chromophores that absorb at wavelengths >290 nm(4), and therefore are not expected to be susceptible to direct photolysis by sunlight(SRC).

Toxicity Summary · 2 items

The CIR Expert Panel concluded that the following 27 Nonoxynols listed below are safe in the present practices of use and concentration in cosmetics as described in this safety assessment, when formulated to be non-irritating..Nonoxynol-2...

Safe for use in cosmetics, with qualifications

Ecotoxicity Excerpts · 2 items

/AQUATIC SPECIES/ The toxicity of the nonylphenol polyethoxylate, R-11 and the neonicotinoid insecticide, imidacloprid were evaluated on the crustacean, Ceriodaphnia dubia Richard. These compounds were evaluated separately and as a mixture because they are applied for pest control and may exist as a binary mixture in surface water. Acute mortality estimates (48hr) were developed followed by population-level studies after chronic exposure. LC50s and 95% CL for R-11 and imidacloprid were 9241(8521-9842)ug/L and 2.1 (1.1-3.4)ug/L, respectively. In the population study, C. dubia were exposed to concentrations equivalent to the acute LC25 for R-11 (8090 ug/L) and imidacloprid (0.3 ug/L) separately and as a mixture for 8d. The results of the chronic study indicated that R-11 had a greater impact on population parameters than imidacloprid and the mixture had a greater impact than either compound alone. For example, the total number of individuals at the end of the chronic study was 73%, 19%, and 6% of the control for imidacloprid, R-11, and the binary mixture, respectively. Additionally, exposure to R-11, imidacloprid, and the mixture resulted in 52%, 10%, and 91% reductions in population growth rate compared to the control, respectively. The results of this study indicate that when combined, R-11 and imidacloprid act in a more than additive manner. Therefore, it is important that their potential effects on aquatic organisms be evaluated together.

/AQUATIC SPECIES/ The ability of nonylphenol polyethoxylate (nonylphenyl polyethylene glycol, NPPG) to alter the metabolic elimination of testosterone and elicit reproductive toxicity to Daphnia magna was assessed. NPPG (5.0 mg/L inhibited the elimination of testosterone as glucose and sulfate conjugates, but had minimal effect on the rate of elimination of oxido-reduced and hydroxylated derivatives of the steroid hormone. This exposure concentration of NPPG also approximated the acute threshold-effect concentration and the chronic value for daphnids. Results demonstrated that NPPG qualitatively elicits similar effects on the metabolic elimination of testosterone by daphnids as previously characterized with its degradation product 4-nonylphenol. Unlike 4-nonylphenol, significant chronic toxicity of NPPG, due to effects on steroid elimination processes, was not evident.

Effluent Concentrations · 2 items

The concentration range of branched and linear polyethylene glycol nonylphenyl ethers in primary effluents from sewage plants in Fallaendan, Dubendorf, Zurich-Glatt, and Niederglatt, Switzerland was 1.3 to 3.8 mmole/cu m(1). The concentration range of branched and linear polyethylene glycol nonylphenyl ethers in secondary effluents from sewage plants in Fallaendan, Dubendorf, Zurich-Glatt, and Niederglatt, Switzerland was 0.02 to 0.3 mmole/cu m(1). The concentrations of nonylphenol, nonylphenol monoethoxylate, and nonylphenol diethoxylate in municipal wastewaters collected from the sewer system of Sibenik, Croatia, in 1990 and 1991, were used to calculated the daily inputs of these compounds of 0.10, 0.18, and 0.12 kg, respectively, into the Sibenik Harbor(2).

Total nonylphenols in untreated wastewaters in ug/L were reported as follows (ug/L): several cities in Spain - 24-938 (n=4-6); textile industry (Canada) - 798.4-8,811.2 (n=3-17); several cities worldwide - 844-2,250 (n=3-18); Danta Maria Nativitas, Mexico - 59.5-229 (n=4-9). Total nonylphenols in treated wastewaters in ug/L were reported as follows (ug/L): several cities in Spain - no detected - 10 (n=3-17); several cities, Canada - 1.00-52.82 (n=3-17); several cities worldwide - 3.9-2250 (n=3-18); Nativitas treatment, wetland, Mexico - 5.28-54.8 (n=4-9)(1).

Soil Adsorption/Mobility · 1 item

Adsorption of nonylphenol polyethoxylates is dependent upon the number of ethoxylate units present; sludge adsorption was greatest for nonylphenol (44-48% of the added compound adsorbed) followed by nonylphenol ethoxylate (n=1) (14-15% of the added compound adsorbed to sludge), and nonylphenol diethoxylate (6-7% of the added compound adsorbed to sludge)(1). Adsorption of nonylphenyl ethoxylate (n=6) to sediment was dependent on the organic matter concentration(2). A Koc of 6.1 was measured in sediment(2). Polyethyleneglycol nonylphenyl ether (n=1-3) was observed to Kd values ranging from 450-1460 L/kg in sediment, 230-590 L/kg in sediment without organic carbon, 25-92 L/kg in silica, and 12,000-13,000 L/kg in sludge, suggesting strong sorption may occur to the solid phase in soil(SRC).

Fish/Seafood ConcentrationsNonylphenol ethoxylates concentrations in fish tissues from the area of Chongqing, China, sampled in December, 2000(1). [Table#6315]
Artificial Pollution SourcesPolyethyleneglycol nonylphenol ether's production and use as a dispersing agent(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 5 items

AEROBIC: An aerobic biodegradation study was conducted on a mixture of polyethylene glycol linear nonylphenyl ethers utilizing sediment inocula from the Yahagi River, Kawasaki, Japan reported 97% and 98% biodegradation after 30 days for standing and stirred samples, respectively(1). An aerobic river die-away test conducted on a mixture of polyethylene glycol linear nonylphenyl ethers with an inoculum obtained from the Arakawa River, Horikiri, Japan reported 98% and 99% biodegradation after 30 days for standing and stirred samples, respectively(1). Two metabolites, nonylphenol diethoxylate and nonylphenol ethoxylate, were identified during these aerobic degradation studies of nonyl substituted polyethylene glycol linear nonylphenyl ether(1). A series of aerobic screening studies were conducted on nonyl substituted polyethylene glycol linear nonylphenyl ethers(2). Results from the aerobic biodegradation of polyethylene glycol linearnonylphenyl ethers for a river die-away, Spanish Official (adapted for anionic compounds), OECD Spanish Official (adapted for nonanionic compounds), and OECD confirmatory test were reported as degradations of 93% in 14 days, 70% in 21 days, 68% in 8 days, 91% in 8 days, and 88% at a retention time of 3 hours, respectively(2). Under conditions simulating a river water environment (Missouri River near Columbia MO, 7.5 miles downstream from the Columbia Wastewater Treatment Plant), over 40% of the 14C ring-labeled polyethylene glycol nonylphenyl ether was converted to 14CO2 in 128 days; overall biodegradation was 87-97%. The water temperature was 20 °C, dissolved oxygen 8.7 mg/L, pH 8.22, alkalinity 180 mg/L, and hardness 270 mg/L; test compound concentration was 100 ug/L(3).

AEROBIC: A coupled units test indicated 61.1% COD removal of a mixture of linear and branched polyethylene glycol nonylphenyl ethers from samples inoculated with acclimated sewage sludge under aerobic conditions. The same study indicated 80% loss of linear and branched polyethylene glycol nonylphenyl ethers in 30 days using an aerobic OECD screening test. Results from an aerobic closed bottle test conducted at an initial concentration of 2 ppm indicated 29% BODT and 84% analytical loss of a mixture of linear and branched polyethylene glycol nonylphenyl ethers after 30 days. An aerobic OECD confirmatory test was conducted using a sewage sludge inoculum acclimated for 34 days, a retention time of 3 hours, and an initial concentration of 20 ppm of a mixture of branched and linear polyethylene glycol nonylphenyl ethers. This OECD confirmatory test reported a 90% analytical loss of this mixture(1).

AEROBIC: The elimination of mixed branched and linear polyethylene glycol nonylphenyl ethers during aerobic biodegradation studies utilizing activated sludge from treatments plants in Fallendorf, Dubendorf, Zurich-Glatt, and Niederglatt, Switzerland was reported as 93%, 76%, 92%, and 92% elimination, respectively(1). Metabolites for the aerobic biodegradation of mixed branched and linear polyethylene glycol nonylphenyl ethers from these studies were reported as nonylphenol diethoxylate and nonylphenol ethoxylate(1). A metabolite for the anaerobic biodegradation of mixed branched and linear polyethylene glycol nonylphenyl ethers was reported as nonylphenol(1). A branched polyethylene glycol nonylphenyl ether underwent 98% aerobic biodegradation at 25 °C during continuous activated sludge treatment seeded with an inoculum from a treatment plant in Harris County, Texas(2). Under the same conditions, a branched polyethylene glycol nonylphenyl ether underwent 98% aerobic biodegradation while the temperature of the system was lowered from 25 to 8 °C over a 10 day period(2). However, polyethyleneglycol nonylphenol ether, present at 30 mg/L, reached 0% of its theoretical BOD in 3 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(3).

Environmental Bioconcentration · 1 item

BCF values of <0.2 to <1.4 were measured in carp at polyethylene glycol nonylphenyl ether concentrations of 2.0 and 0.2 mg/L, respectively. According to a classification scheme(3), these BCF values indicate that bioconcentration of this mixture in aquatic organisms is low(SRC). Nonylphenol, nonylphenol monoethoxylate, and nonylphenol diethoxylate are more lipophilic and may bioconcentrate in aquatic organisms to a greater extent than higher oligomers(3).

Volatilization from Water/Soil · 1 item

Henry's Law constants for polyethylene glycol nonylphenyl ethers range from 2.45X10-9 atm-cu m/mole for nonylphenol, a measured value(1), to 4.1X10-12 atm-cu m/mole for nonylphenol ethoxylate (n=6), from a fragment constant estimation method(2). These values indicate that polyethylene glycol nonylphenyl ethers should be essentially nonvolatile from water surfaces(3). Polyethylene glycol nonylphenyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon vapor pressure values ranging from extrapolated 9.4X10-5 mm Hg(4) to estimated 3.2X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(5).

Non-Human Toxicity Excerpts · 3 items

/LABORATORY ANIMALS: Acute Exposure/ The effects of surfactants (single dose of 50 or 100 mg/kg) were studied on the contents of metallothionein, heme and hemoproteins and on the activities of heme oxygenase and drug metabolizing enzymes in the liver of male Wistar rats pretreated with phenobarbital or beta-naphthoflavone. Surfactants tested included sodium dodecylsulfate, sodium-n-dodecylbenzenesulfonate and Emulgen-913. Metallothionein content was remarkably increased after the injection of surfactants. Phenobarbital alone decreased the Emulgen-913 induced elevation in the contents of zinc of metallothionein, but did not exert any significant effects on the activities of NADPH-cytochrome-c-reductase or DT-diaphorase. These findings suggest that phenobarbital enhances Emulgen-913 metabolism in vivo, and consequently might reduce the contents of surfactant or its metabolites in the liver. Beta-naphthoflavone alone markedly increased the activity of DT-diaphorase and the content of metallothionein but it decreased the activity of NADPH-cytochrome-c-reductase. The increased metallothionein content or DT-diaphorase activity caused by beta-naphthoflavone were further enhanced by Emulgen-913, while NADPH cytochrome-c-reductase was depressed. Phenobarbital pretreatment did not prevent the increase in heme oxygenase activity caused by Emulgen-913, but beta-naphthoflavone pretreatment slightly inhibited the response to Emulgen-913. Cytochrome p-450 was markedly increased by treatment with phenobarbital or beta-naphthoflavone, but these increases were remarkably depressed by subsequent injection of surfactant.

/LABORATORY ANIMALS: Acute Exposure/ The influence of in vivo administration of detergents on the hepatic microsomal cytochrome P-450 system was studied in rat. Male Wistar rats were administered detergents, Emulgen 913 (50 mg or 100 mg/kg of body wt or sodium dodecylsulfate (25 mg or 50 mg/kg of body wt) ip once a day for 3 days. Cytochrome P-450 content in liver microsomes was significantly decreased to 85% and 73% of control by the administration of 50 mg or 100 mg Emulgen, respectively, but the microsomal protein concentration was not changed by these administrations. The content of cytochrome P-450 was also reduced to 76% and 70% of control by the administration of 25 mg or 50 mg sodium dodecylsulfate/kg of body wt, respectively. The total hydroxylation activity (the sum of omega- and (omega-1)-hydroxylase activity) of laurate almost paralleled the decrease in cytochrome P-450 in detergent-treated rats. However, the omega/omega-1-hydroxylation ratio was not changed. These results suggest that the administration of these detergents lowered the level of cytochrome P-450 species catalyzing omega- and (omega-1)-hydroxylation of laurate to a similar extent. On the other hand, aminopyrine N- and p-nitroanisole O-demethylation activities in Emulgen 913-treated rats was decreased while those in sodium dodecylsulfate-treated rats did not change, though the content of cytochrome P-450 was decreased by both administrations

Regulatory information

TSCA Requirements · 1 item

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 2/10/00; Reporting date: 4/10/00.

FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Nonylphenoxypolyethoxyethanol is found on List C. Case No: 3118; Pesticide type: Insecticide, antimicrobial; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Nonylphenoxypolyethoxyethanol; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Safety data

F
3
wgk
2
tsca
TSCA listed
rtecs
WZ4750000
ridadr
UN 3082 9 / PGIII
hs_code
34021300
Toxicity
LD50 oral in rat: 2590uL/kg
risk_code
41-38-37-36/37/38-50-22
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xi,N,Xn
safety_code
26-39-36-61
Storage Class
10 - Combustible liquids
Hazard statements
H315-H319-H412
REACH Registrations
Inactive
Hazard Classifications
Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2
Precautionary statements
P273-P302+P352-P305+P351+P338
Hazardous Substances Data
9016-45-9(Hazardous Substances Data)
Use Classification · 2 items

Fragrance Ingredients

Cosmetics -> Emulsifying; Cleansing; Surfactant

General Manufacturing Information · 3 items

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Poly(oxy-1,2-ethanediyl), .alpha.-(nonylphenyl)-.omega.-hydroxy-: ACTIVE

Ethanol, 2-[2-(4-nonylphenoxy)ethoxy]-: ACTIVE

Applications · 4 items

DescriptionNonylphenol Ethoxylate, also known as NPEs, are nonionic surfactants that are liquid in form. Many different types of NPEs are determined by the number of moles of Ethylene Oxide, or EO. NPEs may function as adjuvants, cleaners, detergents, dispersants, emulsifiers, humectants, solubilizers or wetting agents. Nonylphenol Ethoxylates are used in many applications, including coatings, crop solutions, functional fluids, household, industrial, and institutional cleaning, as well as oil and gas.

UsesNP40 Cell Lysis Buffer is suitable for the preparation of cell extracts to be analyzed by Antibody Bead Immunoassay (Luminex), ELISA, and Western blotting. It can also be used as a wash buffer for immunoprecipitation reactions.

UsesArkopal N 100 is a nonionic surfactant that can be used for testing the stress cracking resistance of polyethylene materials at high temperatures. It is also suitable for enhancing the biodegradation of aromatic hydrocarbon compounds.

General Descriptionwith approx. 10 ethylene oxide units

Upstream & downstream products

Upstream raw materials

NonylphenolTripropylenePOLYETHYLENE GLYCOL MONO-4-NONYLPHENYL ETHER1-Nonanol

Downstream products

Deinking agent for papernonylphenyl polyoxyethylene ether sulfate triethanolamine

Suppliers19 total

艾吉析科技(上海)有限公司17717235263 · [email protected]
廊坊乾耀科技有限公司0316-2617888 17301291189 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
上海稳同科技有限公司02151600108 13062666369 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
凯试(上海)科技有限公司021-50135380 · [email protected]
HANGZHOU LEAP CHEM CO., LTD.+86-571-87711850 +86-15355479329 · [email protected]
热耳科技(上海)有限公司021-64400900 15800436310 · [email protected]
南京佰瑞利康生物科技有限公司18168036974 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
青岛腾龙微波科技有限公司0532-83818797 17669478191 · [email protected]
BOC Sciences+1-631-485-4226 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]

AEROBIC: An acclimated mixed bacterial culture was able to biodegrade an ethoxylated nonylphenol mixture with an average of 10 moles of ethylene oxide (present at 200 mg/L); 88% loss was reported within 4 hours(1). The average elimination rate for all nonylphenol ethoxylated (n=3-20) compounds during activated sludge treatment was 90%(2). Using a static die-away method, a mixture of nonylphenol polyethoxylates was biodegraded following inoculation with bacterial cultures originating from estuarine environments; half-lives of 23-69 days and 2.5-35 days were estimated during winter and summer temperature conditions, respectively(3). Transformation rates of larger, more hydrophilic, oligomers of nonylphenol polyethoxylates were more rapid than those measured for lower oligomers. The elimination of higher nonylphenyl polyethoxylates was followed by a significant formation of the short-chain nonylphenyl polyethoxylates (n=1-4), mainly nonylphenol diethoxylate(3). Nonylphenol, nonylphenol monoethoxylate, and nonylphenol diethoxylate are considered to be relatively resistant to further biodegradation(7). Biodegradation of alkylphenyl ethoxylate compounds generally proceeds via attack at the terminal ethoxylate group, resulting in the shortening of the ethoxylate chain one unit at a time(4,5). Tripropylene phenol ethoxylate with 8, 10, 14, 16, and 30 ethylene oxide groups (at 5 ppm) was more that 90% biodegraded in 12 days following inoculation with sewage(6).

AEROBIC: A highly branched alkyl chain made from propylene trimer and benzene and an average polyoxyethylene chain length of 9 was added to continuous biotreaters seeded with sewage; during the initial acclimation phase this mixture was completely biodegraded at 10, 20, and 40 mg/L(1). However, at 80-100 mg/L breakthrough of the feed appeared in the effluent indicating incomplete biodegradation(1). Nonylphenol polyethoxylate with either 5 or 10 ethoxylate units at four concentrations(3, 10, 30, 100 mg/L) was inoculated with activated sludge(2). BOD, as % theoretical in a BOD test, was measured after 14 days; values of 64, 57, 68, and 33% were measured for the 5 ethoxylate unit compound at 3, 10, 30, and 100 mg/L, respectively(2). Values of 57, 42, 40, and 25% were measured for the 10 ethoxylate unit compound at 3, 10, 30, and 100 mg/L, respectively(2).

/LABORATORY ANIMALS: Acute Exposure/ The influence of in vivo administration of detergents on serum lipid composition was studied in rats. Male Wistar rats received 50 mg Emulgen 913 (polyoxyethylene nonylphenylether, a nonionic detergent) or sodium dodecylsulfate (an anionic detergent) per kg of body weight ip for 3 consecutive days. Emulgen 913 and sodium dodecylsulfate administration increased the level of cholesterol esters and phospholipids, respectively. But Emulgen 913 administration reduced the level of triglycerides in the serum, and sodium dodecylsulfate administration reduced also the levels of triglycerides and cholesterol esters. In spite of the changes in serum lipid composition, the administration of these detergents did not affect the amount of total lipids in rat serum. The proportion of palmitic, oleic, and docosahexaenoic acids in phospholipids was decreased by the administration of Emulgen 913 while the level of arachidonic acid was raised. However, the level sodium dodecylsulfate administration had no effect on the fatty acid composition of the serum phospholipids. On the other hand, both Emulgen 913 and sodium dodecylsulfate administration showed an effect on the fatty acid composition of triglycerides. It is postulated that liver damage due to administration of detergents is responsible for the changes in serum lipid and fatty acid composition in detergent-treated rats.