N-Ethylanilin

Nitrogen Compounds -> Amines, Aromatic

Flammable agents - 2nd degree

log Kow= 2.16

2.16

0.958 at 77 °F (NTP, 1992) - Less dense than water; will float

0.9625 @ 20 °C/4 °C

Relative density (water = 1): 0.96

Colorless liquid

CLEAR TO STRAW-COLORED, YELLOW-BROWN OIL

less than 1 mg/mL at 72 °F (NTP, 1992)

Insol in water; miscible with alcohol, ether, and many other organic solvents

Very sol in acetone; sol in organic solvents

In water, 2.41X10+3 mg/l @ 25 °C

Solubility in water, g/100ml at 25 °C: 0.24

185 °F (NTP, 1992)

185 °F (85 °C) (OPEN CUP)

85 °C o.c.

400.5 °F at 760 mmHg (NTP, 1992)

204.5 °C

205 °C

Decomposes on contact with air or light.

When heated to decomposition ... it emits highly toxic fumes of aniline and nitroxides.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: Benzenamine, N-ethyl-

Status: Active Update: 01-12-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/5338

Ethylaniline: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 85 °C explosive vapour/air mixtures may be formed.

Combustible liquid

MANY AROMATIC AMINES.../SUCH AS/ N-ETHYLANILINE...ARE HYPERGOLIC WITH RED FUMING NITRIC ACID. WHEN THE AMINES ARE DISSOLVED IN TRIETHYLAMINE, IGNITION OCCURS AT -60 °C & BELOW.

Flammable when exposed to heat or flame ...

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

N-ETHYLANILINE may react violently with nitric acid. May react with strong oxidizing agents. (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

Store away from heat, oxidizing materials, and sunlight in a dry, well-ventiliated location. Outside or detached storage is preferred.

KEEP WELL CLOSED & PROTECTED FROM LIGHT.

Approach release from upwind. Stop or control the leak, if this can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Absorb in noncombustible material for proper disposal. Control runoff and isolate discharged material for proper disposal.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that N-ethylaniline is expected to have high mobility in soil(SRC). However, aromatic amines (including anilines) bind to humic material found in soil in two phases(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). Also, a pKa value of 5.09(4) suggests that N-ethylaniline will exist partially in the protonated form in moist soils and the protonated form of N-ethylaniline is expected to bind strongly to soil surfaces. Volatilization of the neutral species from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(5). The few biodegradation studies that have been located have conflicting results concerning the extent of biodegradation. N-ethylaniline has acheived 0-64% of its theoretical BOD in biodegradation studies(6,7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from an estimation method(2), indicates that N-ethylaniline is not expected to adsorb to sediment and suspended solids in water(SRC). Volatilization of the neutral species from water surfaces is expected(3) based upon a Henry's Law constant of 1.6X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 41 hrs and 22 days, respectively(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humic material in the water column(5). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(5). Subsequently, there is a slow reaction that is not readily reversed(5). A pKa value of 5.12(6), suggests that N-ethylaniline will exist partially in the protonated form in aqueous environments and the protonated form of N-ethylaniline does not volatilize from water. According to a classification scheme(7), a BCF ranging from 3 to 13 (8), suggests the potential for bioconcentration in aquatic organisms is low. There is not enough experimental data to determine the biodegradation potential of N-ethylaniline. The few studies that have been located have conflicting results concerning the extent of biodegradation(SRC). N-Ethylaniline has acheived 0-64% of its theoretical BOD in biodegradation studies(8,9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-ethylaniline, which has a vapor pressure of 0.204 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N-ethylaniline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.5 hrs(SRC), calculated from its estimated rate constant of 5.1X10-11 cu cm/molecule-sec at 25 °C determined using a structure estimation method(3).

Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.

Redness. Pain. See Inhalation.

Redness. Pain.

Weakness. See Inhalation.

Effluent from 3 New Jersey publicly owned treatment works (POTWs) was analyzed for the presence of pollutants(1). These POTWs were sampled for 1 year with POTW-A located in a rural area with no known industrial contributor, POTW-B located in an industrial area with intake water having 27% industrial (consisting of pharmaceutical, yeast, paper processing and chemical manufacturing) contribution and POTW-C located in another industrial area with 18% industrial (mostly textile and dye manufacturers) contribution to intake water(1). N-Ethylaniline was only detected in effluent water from POTW-C at 12 ppb(1).

A pKa value of 5.12(1) suggests that N-ethylaniline will exist partially in the protonated form in moist soils and the protonated form of N-ethylaniline is expected to bind strongly to soil surfaces(SRC). Using a structure estimation method based on molecular connectivity indices(2), the Koc for N-ethylaniline can be estimated to be 120(SRC). According to a classification scheme(3), this estimated Koc value suggests that N-ethylaniline is expected to have high mobility in soil. However, primary and secondary amines (including anilines) bind to humic material found in soil in two phases(4). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(4). Subsequently, there is a slow reaction that is not readily reversed(4).

EXCESSIVE EXPOSURE CAUSES RESP PARALYSIS.

HIGHLY TOXIC ON ABSORPTION THROUGH SKIN, BY INHALATION OR INGESTION.

AEROBIC: N-Ethylaniline, present at 100 mg/l, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1). N-Ethylaniline was introduced into a sand-filtration system in which the reduction of organic chemicals was primarily through microbial decomposition(2). In two water treatment plants using slow sand-filtration techniques, N-ethylaniline was detected at greater than 10 ng/l in the effluent (initial concn not specified)(2). It was not clear the percent (if any) of biodegradation that occurred in this study(2). In a study of the biological oxygen demand (BOD) over 5 days, N-ethylaniline reached 64% of its chemical oxygen demand (COD) while in a BOD test over 30 days, N-ethylaniline reached 70% of its COD(3).

The Henry's Law constant for N-ethylaniline is estimated as 1.6X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that the neutral species of N-ethylaniline is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 41 hrs(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 22 days(SRC). However, volatilization from water surfaces may be attenuated by adsorption to humic material in the water column(3). Initially, a rapid, reversible equilibrium is established, which may represent formation of imine linkages with the humic carbonyls(3). Subsequently, there is a slow reaction that is not readily reversed(3). N-Ethylaniline's Henry's Law constant(1) indicates that volatilization of the neutral species from moist soil surfaces may occur(SRC). N-Ethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.204 mm Hg(4). A pKa value of 5.12(5), suggests that N-ethylanilne will exist partially in the protonated form in aqueous environments and the protonated form of N-ethylaniline does not volatilize from water or moist soil surfaces(SRC).

METABOLIZED TO ANILINE; N-ETHYL-P-AMINOPHENOL & PHENYLHYDROXYLAMINE IN RABBIT. PHENYLHYDROXYLAMINE IN PIG. /FROM TABLE/

N-ETHYLANILINE WAS CONVERTED TO PHENYLHYDROXYLAMINE BY RABBIT LIVER MICROSOMES. THE OXYGENATING SYSTEM HAD LOW AFFINITY FOR OXYGEN, WAS NOT INHIBITED BY CARBON MONOXIDE & WAS NOT STIMULATED BY SC TREATMENT OF RABBITS WITH SODIUM PHENOBARBITAL 50 MG/KG 10 TIMES IN 2 WEEKS. P-CHLOROMERCURIBENZOATE, N-ETHYLMALEIMIDE & 2,4-DICHLOROPHENOL STIMULATED N-HYDROXYLATION. 8-HYDROXYQUINONE & SEMICARBAZIDE INHIBITED N-HYDROXYLATION. OXYGENATION WAS MOST RAPID AT PH 8.5 & DECREASED AS LENGTH OF STORAGE INCREASED.

IN LIVER MICROSOMES FROM RABBITS TREATED FOR 19 DAYS WITH SODIUM PHENOBARBITAL 40 MG/KG/DAY SC, THE CONTENT OF CYTOCHROME B5 WAS INCR 4- TO 5-FOLD, CYTOCHROME P450, ETHYL ISOCYANIDE 430, & ETHYL ISOCYANIDE 434 8- TO 9-FOLD, & ETHYL ISOCYANIDE 455 13-FOLD. P-HYDROXYLATION & THE OPTICALLY MEASURED BINDING OF N-ETHYLANILINE INCR TO SAME EXTENT AS ETHYL ISOCYANIDE 455. N-HYDROXYLATION WAS NOT STIMULATED. CYTOCHROME P450 OR ONE OF THE ETHYL ISOCYANIDE COMPD IS INVOLVED IN DEALKYLATION & P-HYDROXYLATION BUT NOT IN THE N-HYDROXYLATION.

CARBON MONOXIDE, IN ABUNDANCE IN ATMOSPHERE OF REACTION VESSELS, INHIBITS P-HYDROXYLATION (BUT NOT N-HYDROXYLATION), & INHIBITS DEALKYLATION OF N-ETHYLANILINE BY MICROSOMES OF LIVER FROM RABBITS. EFFECTS REVERSED BY IRRADIATION WITH MERCURY HIGH PRESSURE LAMPS.

For more Metabolism/Metabolites (Complete) data for N-ETHYLANILINE (6 total), please visit the HSDB record page.

.../ABSORBED/ THROUGH SKIN, BY INHALATION OR INGESTION.

... Readily absorbed by the inhalation, dermal and oral routes.

Used to manufacture dyes and explosive stabilizers; [HSDB]

Organic synthesis

Used as an explosive stabilizer and in dye stuff manufacturing as a cyclic intermediate.

Feed stock for the manufacture of dyes and stabilizers

Explosive stabilizer

... by heating aniline hydrochloride and alcohol at 180 °C.

By heating aniline and ethyl alcohol in presence of sulfuric acid, with subsequent distillation.