ジブチルアミン

Nitrogen Compounds -> Amines, Aliphatic

Corrosives

log Kow= 2.83

2.83

2.68

0.759 at 68 °F (USCG, 1999) - Less dense than water; will float

0.7601 @ 20 °C/4 °C

Density (at 20 °C): 0.76 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.01

0.7613 @ 20°C

Liquid

Colorless

Soluble (NTP, 1992)

Sol in alcohol

Very sol in ether and ethanol; sol in acetone

3500 mg/l in water @ 25 °C

Solubility in water, g/100ml: 0.35 (slightly soluble)

125 °F (NTP, 1992)

57 °C

57 °C (open cup)

51.6 °C (open cup)

47 °C

318 to 320 °F at 760 mmHg (NTP, 1992)

159-160 °C

159 °C

159.6 °C @760 [mm Hg]

When heated to decomp it emits toxic fumes of /nitrogen oxides/.

Products of decomposition include carbon monoxide, carbon dioxide, hydrocarbons, & oxides of nitrogen as well as amine vapors.

-76 to -74 °F (NTP, 1992)

-60 to -59 °C

-59 °C

-61.9 °C

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P361+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Chemical: 1-Butanamine, N-butyl-

1-Butanamine, N-butyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Butanamine, N-butyl- 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)

Status: Active Update: 01-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13527

1-Butanamine, N-butyl-: 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.)

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fires. (USCG, 1999)

· Flammable/combustible material.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 47 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion on contact with strong acids or strong oxidizing agents.

Inhalation causes irritation of nose, throat, and lungs; coughing; nausea; headache. Ingestion causes irritation of mouth and stomach. Contact with eyes causes irritation. Contact with skin causes irritation and dermatitis. (USCG, 1999)

· May cause toxic effects if inhaled or ingested.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Dibutylamine is included on this list.

DI-N-BUTYLAMINE 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.

Decomposes on burning. This produces toxic fumes including nitrogen oxides. The substance is a strong base. Reacts violently with strong oxidants. This generates fire and explosion hazard. Attacks some metals and some plastics. Solutions in water slowly etch glass.

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:

Use alcohol-resistant foam, water, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Refer immediately for medical attention .

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give nothing to drink. Do NOT induce vomiting. Refer immediately 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:

· Wear positive pressure self-contained breathing apparatus (SCBA).

173.0 [ppm]

Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool.

USE WATER SPRAY, DRY CHEM, "ALCOHOL" FOAM, OR CARBON DIOXIDE. USE WATER SPRAY TO KEEP FIRE-EXPOSED CONTAINERS COOL. IF LEAK OR SPILL HAS NOT IGNITED, USE WATER SPRAY TO DISPERSE VAPORS & TO PROTECT MEN ATTEMPTING TO STOP LEAK. WATER SPRAY MAY BE USED TO FLUSH SPILLS AWAY FROM EXPOSURES.

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.

Remove all ignition sources. Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Cover the spilled material with inert absorbent or sand. Then store and dispose of according to local regulations. Wash away remainder with plenty of water.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Nitrite ... is used as a food additive in meats and smoked fish. Some fish, vegetables, and fruit juices contain secondary amines. The acidic environment of the stomach facilitates a chemical reaction between nitrite and secondary amines, leading to the formation of carcinogenic nitrosamines. /Secondary amines/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 825(SRC) for the unprotonated form from a log Kow of 2.83(2) and a regression derived equation(3) indicates that dibutylamine is expected to have low mobility in soil(SRC). A pKa value of 11.39(4) indicates that the protonated form of dibutylamine will be the dominant species in moist soil surfaces and cations generally adsorb strongly to soils. Volatilization of dibutylamine from moist soil surfaces is not expected to be an important fate process since the cation is not expected to volatilize. The potential for volatilization of dibutylamine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2.59 mm Hg at 25 °C(5). 94-97% of the theoretical BOD was achieved for dibutylamine using an activated sludge inoculum during a 4 week incubation period(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 825(SRC) from a log Kow of 2.83(2) and a regression derived equation(3) indicates that dibutylamine is expected to adsorb to suspended solids and sediment in water(SRC). A pKa value of 11.39(4) indicates that the protonated form of dibutylamine will be the predominant species in water. Volatilization from water surfaces is not expected to be important fate process(SRC) since the protonated form will not volatilize at environmental pH. According to a classification scheme(5), an estimated BCF of 30(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). In a screening study, dibutylamine completely degraded within 14 days at 10 ppm with both an activated sludge and freshwater sediment inoculum(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibutylamine, which has a vapor pressure of 2.59 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dibutylamine 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 4 hours(SRC), from its rate constant of 8.98X10-11 cu cm/molecule-sec at 25 °C(3). Dibutylamine is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(SRC).

... Amines from decomposing fish have been suspected as a cause of keratitis. ... /Amines/

Dibutylamine was detected in pepperoni at a concn of 3.4 ppm(1). An average dibutylamine concn of 10 ppb was found in 3 samples of cod roe; however, it was not detected in samples of fish sausage, baked ham, spinach, or miso(2).

Cough. Sore throat. Burning sensation. Shortness of breath. Laboured breathing.

Redness. Pain. Serious skin burns.

Redness. Pain. Blurred vision. Severe burns.

Burns in mouth and throat. Burning sensation behind the breastbone. Abdominal pain. Vomiting. Shock or collapse.

In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, dibutylamine was identified in discharges of the following industrial category (frequency of occurrence, median concn in ppb): iron and steel mfg (4; 170.4), plastics and synthetics (1; 89.1), electronics (1; 6723.3)(1). Dibutylamine was reported to be released from effluent of sewage treatment plants(2).

The Koc of dibutylamine was estimated as 825(SRC), using a log Kow of 2.83(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dibutylamine is expected to have low mobility in soil(SRC). The pKa of dibutylamine is 11.73(4), indicating that the protonated form will be the predominant species in moist soils and cations are expected to adsorb strongly to soil surfaces.

Acute inhalation toxicity was evaluated in groups of 5 male and 5 female Sprague-Dawley albino rats exposed to dibutylamine at actual concentrations of 0.76, 1.08, 1.18, 1.39 or 3.91 mg/l of air for 4 hours. Mortality was observed in 2 animals in the 0.76 mg/l dose group, 4 in the 1.18 mg/l dose group, and all 10 in both the 1.39 and 3.91 mg/l dose groups. The LC50 value was calculated to be 1.15 mg/l (standard error of 0.095 mg/l) by the log probit method of Miller and Tainter. Clinical observations included excessive salivation, lacrimation, gasping, convulsions, abnormal breathing, ataxia, lethargy, rales, and staining of the urogenital area. Gross necropsy revealed lung congestion in decedents.

The inhibition of nonspecific esterase activity, and/or inhibition of aromatic amino acid esterase activity, and/or potential effects on specific cellular functions (phagocytosis, immunoglobin G synthesis, and inflammatory and immune mediator release) were evaluated with organic chemicals added to human peripheral blood monocytes. Di-n-butylamine stimulated monocyte alpha- naphthyl acetate esterase activity by 104% at a concentration of 1 mM, and 116% at 0.25 mM and stimulated monocyte aromatic amino acid esterase activity by 103% at 250 uM. Only the low-dose value for alpha-naphthyl acetate esterase stimulation was considered to be statistically significant.

The dermal sensitization potential of di-n-butylamine (CAS # 111-92-2) was evaluated in 10 CF1(BR) mice inducted with 3 daily 0.1 ml topical applications of a 0.1% (v/v in ethanol) test solution to clipped abdomens. A group of 10 mice likewise inducted over 3 days with 0.1 ml dermal applications of 0.5% (w/v) DNCB served as the positive control. Challenge and rechallenge were administered 7 and 14 days later in .01 ml dermal applications of a 25% (v/v) solution to both dorsal and ventral surfaces of the left and right ears respectively of inducted test mice. The thickness of treated left ears relative to that of solvent control (ethanol) right ears indicated the degree of sensitization. One animal challenged with di-n-butylamine exhibited a positive sensitization response (20% increase in ear thickness over control) at 48-hour evaluation only. None of either test or irritation control groups had responded to challenge by the 24-hour evaluation and none responded to rechallenge. Conversely, 60% and 50% positive response in the DCNB-inducted and challenged groups at 24-hour and 48-hour evaluations, respectively, confirmed the validity of the test system.

The clastogenic potential of di-n-butylamine (CAS # 111-92-2) was evaluated by incidence of micronucleated polychromatic erythrocytes in bone marrow of Harlan Sprague-Dawley ICR mice (20/sex/group) administered single oral gavage doses at 55, 110, or 220 mg/kg bodyweight. Mortality occurred among high-dose males (3/20) and females (1/20), and lethargy was observed in both males and females of all treatment groups. While treated mice exhibited slight reductions in polychromatic erythrocytes to erythrocyte ratios (up to 19%) relative to vehicle control (corn oil) animals, there was no significant increase in micronucleated polychromatic erythrocytes at 24, 48 or 72-hour post-treatment examination in either male or female treated mice when compared to controls.

There is some indication that dibutylamine may occur naturally in some soils(1) and food items(2). Amines are produced by microbial processes in decaying organic matter and dibutylamine's emission from sewage treatment plants(3) suggests that it may also be a product of microbial metabolism(SRC).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Dibutylamine is included on this list.

Used as a corrosion inhibitor and chemical intermediate; [HSDB]

Corrosion inhibitor; intermediate for emulsifiers, rubber accelerators, dyes, insecticides, flotation agent, inhibitor for butadiene

2023: 10,000,000 - <50,000,000 lb

(1972) 1.7X10+9 GRAMS

(1975) PROBABLY GREATER THAN 9.08X10+5 GRAMS

(1981) 6,279X10+3 lb

(1985) 4,141X10+3 lb

By reaction of butanol or butyl chloride with ammonia

From butyl bromide & ammonia with separation of the mono-, di-, & tributylamines formed.

All Other Basic Organic Chemical Manufacturing

1-Butanamine, N-butyl-: ACTIVE