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Home > Encyclopedia > Butylamine

Butylamine

Butylamine structure

Butylamine 

structure
  • CAS No:

    109-73-9

  • Formula:

    C4H11N

  • Chemical Name:

    Butylamine

  • Synonyms:

    1-Butanamine;Butylamine;1-Aminobutane;Mono-n-butylamine;Norvalamine;n-Butylamine;Monobutylamine;1-Butylamine;NSC 8029;42939-72-0;50929-03-8;85404-21-3

  • Categories:

    Organic Chemistry  >  Amides

Description

n-Butylamine is a derivative of ammonia in which one of the hydrogen atoms is replaced with an alkyl group of four carbons. As such, it reacts with water and acids to form bases and salts, respectively. Acting as a very weak acid, it can react with acyl halides, anhydrides, and esters. With carbon disulfide and carbon dioxide, it forms the butyl ammonium salt of dithiocarbamic and carbamic acids, respectively. With isocyanic acid and alkyl or aryl isocyanates, it forms substituted ureas.


N-butylamine appears as a clear colorless liquid with an ammonia-like odor. Flash point 10°F. Less dense (6.2 lb / gal) than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR. TURNS YELLOW ON STANDING.|Colourless liquid, tends to yellow on standing; Ammoniacal aroma|Colorless liquid with a fishy, ammonia-like odor.


N-butylamine appears as a clear colorless liquid with an ammonia-like odor. Flash point 10°F. Less dense (6.2 lb / gal) than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.|Butan-1-amine is a primary aliphatic amine that is butane substituted by an amino group at position 1.|Butylamine is a colourless liquid which acquires a yellow colour upon storage in air. It is one of the four isomeric amines of butane. It is known to have the fishy, ammonia-like odor common to amines.

Butylamine Basic Attributes

73.14

73.14

605269

203-699-2

N2QV60B4WR

0374

8029

1125

DTXSID1021904

CLEAR, COLORLESS LIQUID

29211980

Characteristics

26

0.86

Clear Liquid

0.7327 g/cm3 @ Temp: 25 °C

-50 °C

78 °C

30 °F

n 20/D 1.401(lit.)

water: miscible

2-8°C

68 mm Hg ( 20 °C)

2.5 (vs air)

Oral-Rat  LD50: 366 mg/kg; Oral-Mouse LD50: 430  mg/kg

Inflammable in case of open flame, high temperature, oxidant; burning produces toxic nitrogen oxide fumes; corrosive

1.5-9.8%(V)

Amine odor

10.8(at 20 °C)

1.74e-05 atm-m3/mole|Henry's Law constant = 1.74X10-5 atm cu-m/mol at 25 °C

10.8 (at 20 °C)|pKa = 10.78 at 20 °C (conjugate acid)

1 MG/L IS EQUIVALENT TO 334 PPM; 1 PPM IS EQUIVALENT TO 2.99 MG/CU M|Surface tension 19.7 dynes/cm when in contact with nitrogen @ 41 °C.|Liquid butylamine will attack some forms of plastics, rubber, and coatings.|It weighs 6.2 lb/gal

Highly flammable. Dissolves in water with evolution of heat. The resulting solutions are basic.

Amines, Phosphines, and Pyridines

Highly Flammable

N-BUTYL AMINE reacts violently with strong oxidizing agents and acids. Attacks copper and copper compounds [Handling Chemicals Safely 1980 p. 123]. Reacts with hypochlorites to give N-chloroamines which may be explosive when isolated [Bretherick 1979 p. 108].

594 °F (USCG, 1999)|594 °F (312 °C)|312 °C

-3018.4 kJ/mole (liquid) at 25 °C

8.71 eV

Lower flammable limit: 1.7% by volume; Upper flammable limit: 9.8% by volume|Class IB Flammable Liquid: Fl.P. below 73°F and BP at or above 100°F.

The vapour is heavier than air and may travel along the ground; distant ignition possible.

It may corrode some metals in the presence of water.

35.72 kJ/mole at 25 °C

CRITICAL TEMPERATURE: 484 °F = 251 °C = 524 DEG K; CRITICAL PRESSURE: 603 PSIA = 41 ATM = 4.16 MN/SQ M|Critical temperature: 531.9 K; critical pressure: 4.25 MPa

Safety Information

II

3

UN 1125 3/PG 2

1

11-20/21/22-35

3-16-26-29-36/37/39-45

EO2975000

F,C

The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids

Explosive when mixed with air

Stable. Incompatible with oxidizing agents, aluminium, copper, copper alloys, acids. Highly flammable.

P210-P261-P280-P303 + P361 + P353-P305 + P351 + P338-P370 + P378

H225-H290-H302-H311 + H331-H314

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.|Incineration; incinerator is equipped with a scrubber or thermal unit to reduce NOx emissions. Alternatively it may be poured into sodium bisulfate, neutralized and flushed with water.|/Absorb small spills with paper and/ burn the paper in a suitable location away from combustible materials. Large quantities can be reclaimed or collected & atomized in suitable combustion chamber equipped with appropriate effluent gas cleaning device.

Forms explosive mixture with air. May accumulate static electrical charges, and may cause ignition of its vapors. n-Butylamine is a weak base; reacts with strong oxidizers and acids causing fire and explosion hazard. Incompatible with organic anhydrides, isocyanates, vinyl acetate, acrylates, substituted allyls, alkylene oxides, epichlorohydrin, ketones, aldehydes, alcohols, glycols, phenols, cresols, caprolactum solution. Attacks some metals in presence of moitsure. /Butyl Amines/|Incompatiblities: Contact with strong oxidizers may cause fires and explosions. Contact with strong acids will cause spattering.|Strong oxidizers, strong acids.|Explodes on contact with perchloryl fluoride.

European Chemicals Bureau; IUCLID Dataset, Butylamine (CAS # 109-73-9) (2000) gives information on usage patterns, ecotoxicity, and toxicity provided to the European Union by industry.|Anon; Dangerous Prop Ind Mater Rep, 6(2): 45-48 (1986) Safety of butylamine|Canadian Centre for Occupational Health and Safety p.1 (1990). Chemical safety information sheet.

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. Behavior in Fire: Vapor is heavier than air and may travel to a source of ignition and flash back. Containers may explode in fire. (USCG, 1999)|Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.|Flammable - 3rd degree

|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P370+P378, P403+P235, P405, and P501|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 2231 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P310, P311, P312, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501|P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P312, P314, P321, P322, P330, P361, P363, P370+P378, P403+P235, P405, and P501

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb with earth, sand or other non-combustible material and transfer to containers (except for Hydrazine). Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet should be immediately removed due to its flammability hazard(i.e. for liquids with flash point Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Teflon is recommended by safety equipment suppliers/manufacturers for n-Butylamine and Chlorinated polyethylene (CPE) and VITON/chlorobutylene for Isobutylamine. Contact lenses should not be worn when working with this chemical. Wear dust-proof chemical goggles and face shield unless full face-piece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash. /Butyl Amines/|SRP: When working with strong solutions of acids or bases or other caustic or corrosive materials, always wear a full face mask. When working with caustic or corrosive gases or vapors, a full face mask will not protect the eyes or prevent inhaling the material. A full face respirator is required.|Breakthrough times of chlorinated polyethylene by butylamine are less (usually significantly less) than one hour, reported by (normally two or more testers).|To prevent contact with skin and eyes, /use/ ... splash goggles, face shield, apron, boots, impervious shirt and trousers, hard hat with brim. Chemical-proof suits should be available and worn as appropriate.|For more Personal Protective Equipment (PPE) (Complete) data for N-BUTYLAMINE (14 total), please visit the HSDB record page.|(See protection codes)

Flammable

lel: 1.7%; uel: 9.8%|Explosive limits , vol% in air: 1.7-9.8

Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.|Do not use a solid stream of water because the stream will scatter and spread the fire. ... Fire fighters should wear self-contained breathing apparatus and full set of protective clothing.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.|Fire Fighting: Use self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode.

VAPORS ARE HEAVIER THAN AIR & MAY TRAVEL CONSIDERABLE DISTANCE TO SOURCE OF IGNITION & FLASH BACK.

Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable. /Butyl Amines/|Evacuate danger area! Consult an expert! Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT let this chemical enter the environment. Personal protection: chemical protection suit including self-contained breathing apparatus.|1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quantities, absorb on paper towels. Evaporate in a safe place (such as fume hood). Allow sufficient time for evaporating vapors to completely clear the hood ductwork. ... butylamine should not be allowed to enter a confined space, such as sewer, because of the possibility of an explosion. Sewers designed to preclude the formation of explosive concentrations of butylamine vapors are permitted.|Environmental considerations-land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Apply appropriate foam to diminish vapor and fire hazard. Neutralize with sodium bisulfate (NaHSO4).|For more Cleanup Methods (Complete) data for N-BUTYLAMINE (6 total), please visit the HSDB record page.

... Substitution of less irritating substances ... redesign of operations ... prevent contact, provision of a physical barrier against contact, proper washing facilities, work clothing and storage facilities, protective clothing, and barrier creams. Medical control ...|Clothing contaminated with liquid butylamine should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of butylamine from the clothing. If the clothing is to be laundered or otherwise cleaned to remove the butylamine, the person performing the operation should be informed of butylamine's hazardous properties. Where there is any possibility of exposure of an employee's body to liquid butylamine, facilities for quick drenching of the body should be provided within the immediate work area for emergency use. Any clothing which becomes contaminated with liquid butylamine should be removed immediately and not reworn until the butylamine is removed from the clothing.|Provide general and local exhaust ventilation (explosion proof) to meet TLV requirements. ... Fume hoods should have an average face velocity of 100 linear ft/min. All electrical service in use or storage areas should have an explosion-proof design. ... If liquid gets on the skin, the exposed area should be drenched with water immediately, make ... eyewash stations readily available in use and handling areas.|Ground and bond containers and equipment when transferring or pouring liquid to prevent static sparks. Use non-sparking tools. Do not smoke in areas where this material is handled or stored.|For more Preventive Measures (Complete) data for N-BUTYLAMINE (12 total), please visit the HSDB record page.

/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Fire or Explosion: Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Health: May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for N-BUTYLAMINE (8 total), please visit the HSDB record page.

Requires a shipping label of: "Flammable Liquid." It falls into DOT Hazard Class 3 and Packing Group II.|No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Potent skin, eye, mucous membrane irritant.

Permissible Exposure Limit: Table Z-1 Ceiling value: 5 ppm (15 mg/cu m). Skin designation.

Recommended Exposure Limit: 15-Min Ceiling Value: 5 ppm (15 mg/cu m). Skin.

Evacuate danger area! Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Ventilation. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Fireproof. Separated from food and feedstuffs. See Chemical Dangers.

A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.

The substance and the vapour are corrosive to the eyes, skin and respiratory tract. Inhalation of the vapour may cause lung oedema. The effects may be delayed. Medical observation is indicated.

Repeated or prolonged contact with skin may cause dermatitis.

NO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. n-Butylamine is produced, as an intermediate or a final product, by process units covered under this subpart.

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

In 16 finished water concentrates collected from advanced waste treatment plants across the US, n-butylamine was detected, but not quantified, in 1087 of 2097 detection instances(1). In a laboratory study, n-butylamine was detected in the automobile exhaust of two gasoline fueled vehicles, concn not specified(2).

n-Butylamine has been determined to be a volatile component of cattle feed lots, probably from the decomposition of manure(1). n-Butylamine is a constituent of tobacco smoke(2).

Toxicity

highly toxic

Oral rat LD50 is 366 mg/kg.

LD50 Rat oral 500 mg/kg|LD50 Rat oral 366 mg/kg|LD50 Rat ip 48 mg/kg|LC50 Rat inhalation 4.2 mg/cu m/4 hr|For more Non-Human Toxicity Values (Complete) data for N-BUTYLAMINE (11 total), please visit the HSDB record page.

/AQUATIC SPECIES/ Of 78 binary mixtures of equitoxic concns of 13 amines, the ethyl amine-aniline mixture (I-II) showed the greatest (32-fold) toxicity potentiation in a /freshwater algae/ Scenedesmus subspicatus reproduction test. ... Combining I with Butylamine ... potentiated the toxicity 8-fold.

... Employees /with chronic respiratory, skin, or eye disease are/ at increased risk from butylamine exposure.

... amines from decomposing fish ... /Amines/|OCCURS NATURALLY IN MULBERRY LEAVES.|n-Butylamine has been reported to be a component of animal waste(1).

n-Butylamine's production and use as a chemical intermediate for pharmaceuticals, dyestuffs, rubber chemicals, emulsifying agents, insecticides, and synthetic tanning agents(1), as well as its use in sewage treatment, fertilizer manufacture, fish processing, and rendering plants(2), may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 15 to 107(2) indicate that n-butylamine is expected to have high mobility in soil(SRC). The pKa of n-butylamine is 10.78(3) indicating that this compound will exist almost entirely in the cation form in the environment and therefore volatilization from moist soil surfaces is not expected to be an important fate process(SRC). The potential for volatilization of n-butylamine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 92.9 mm Hg(4). Numerous screening studies indicate that n-butylamine will biodegrade readily(5-8); n-butylamine reached 67% of its theoretical BOD in 12 days using an activated sludge inoculum(5).|AQUATIC FATE: Based on a classification scheme(1), a Koc value range of 15 to 107 in soil and sediment(2), indicates that n-butylamine is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 10.78(3) indicates n-butylamine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Numerous screening studies indicate that n-butylamine will biodegrade readily(8-11); n-butylamine reached 67% of its theoretical BOD in 12 days using an activated sludge inoculum(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-butylamine, which has a vapor pressure of 92.9 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-butylamine 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 11 hours(SRC) from its estimated rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(3).

The rate constant for the vapor-phase reaction of n-butylamine with photochemically-produced hydroxyl radicals has been estimated as 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the aqueous-phase reaction with photochemically-produced hydroxyl radicals has been determined to be 7.7X10+9 L/mol-sec at pH 8-13(2). This corresponds to as aqueous half-life of approximately 104 days at an aqueous hydroxyl radical concn of 1.0X10-17 mol/l(2). n-Butylamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3).

An estimated BCF of 3 was calculated in fish for n-butylamine(SRC), using a log Kow of 0.97(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

75.86 L/kg|The Koc of n-butylamine has been determined to be 15, 105 and 107 in Podzol soil, Alfisol soil and sediment, respectively(1). According to a classification scheme(2), these Koc values suggest that n-butylamine is expected to have high mobility in soil(SRC). The pKa of n-butylamine is 10.78(3) indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

A pKa of 10.78(1) indicates n-butylamine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(2). The potential for volatilization of n-butylamine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 92.9 mm Hg(5).

SURFACE WATER: n-Butylamine was detected in the River Elbe from 1 of 2 sites at a concn of 1.5 ppb; not detected at 7 other sites (detection limit not given)(1).

n-Butylamine has been detected to occur naturally in the following foods: kale, 7 ppm; pickles: cucumbers in aromatic vinegar, 0.6 ppm, cucumbers pickled with mustard, 5.3 ppm; cheese: Tilsiter, 3.7 ppm, Camembert and Limburger, not detected; brown bread, 1.1 ppm(1). Not detected in: spinach, red cabbage, cauliflower, white beet, carrot, red beet, large raddish, red radish, celery(1). n-Butylamine has been identified as a volatile component of boiled beef, concn unknown(2).

... The presence of volatile aliphatic amines ... in human breast milk and amniotic fluid /was measured/ to assess their role in neonatal hypergastrinemia. These volatile nitrogenous amino acid metabolites have been previously demonstrated to stimulate gastrin release in in vivo and in vitro laboratory preparations. ... The present study ... demonstrated that these gastrin-stimulatory volatile amines were present in significant concentrations in breast milk during the first several weeks after parturition and in amniotic fluid. The individual amines that were identified in both human milk and amniotic fluid samples were methylamine, dimethylamine, ethylamine, trimethylamine, propylamine, isobutylamine, and butylamine. This study provides indirect evidence to support the possibility that the hypergastrinemia measured in the fetus/neonate during the period immediately before and after birth may be attributable, in part, to the ingestion of fluid containing high concentrations of gastrin-stimulating amines.

Butylamine can affect the body if it is inhaled, and if it comes in contact with the eyes or skin. ... It may enter the body through the skin.|NIOSH (NOES Survey 1981-1983) has statistically estimated that 413 workers (85 of these are female) are potentially exposed to n-butylamine in the US(1). Occupational exposure to n-butylamine may occur through inhalation and dermal contact with this compound at workplaces where n-butylamine is produced or used(SRC). Monitoring data indicate that the general population may be exposed to n-butylamine via ingestion of food(SRC).

Drug Information

... Recovered little ... n-butylamine in the urine after oral administration of the hydrochloride of this compound to humans ...|Amines are well absorbed from gut & respiratory tract. /Aliphatic amines/

Monoamine oxidase and diamine oxidase (histaminase) occur widely in animal tissues ... it is assumed that they play an important part in "detoxication" of amines not normally present /in the body/. /Aliphatic amines/

Inhalation causes irritation, nausea, vomiting, headache, faintness, severe coughing and chest pains; can cause lung edema. Ingestion causes severe irritation of mouth and stomach. Contact with eyes causes severe irritation and edema of the cornea. Contact with skin causes burns; absorption through skin may cause nausea, vomiting and shock. (USCG, 1999)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting. Thus, the risk of increasing the medical problems by inducing vomiting of a volatile corrosive chemical is very high. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(See procedures)


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


Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .


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

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mg/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/|Immediate skin and eye reactions are not appreciably altered by prolonged washing or attempts at neutralzation when these are commenced within 15 sec after application.

/SIGNS AND SYMPTOMS/ Workers with daily exposures of from 5 to 10 ppm complain of nose, throat, and eye irritation, and headaches. ... Daily exposures to less than 5 ppm (most often between 1 and 2 ppm) produce no complaints or symptoms.|/SIGNS AND SYMPTOMS/ Exposure to excessive concn of vapor may result in erythema, ... faintness, coughing, chest pains, dizziness, depression, convulsions, /CNS depression/, and possibly unconsciousness. Exposure of this nature is unlikely, however, because of the irritating properties of the vapor. ... Contact with the eyes may cause burns, severe damage, and loss of vision. Ingestion of n-butylamine causes irritation to the mouth, throat, and gastrointestinal tract and may cause nausea, vomiting, and possibly death. Skin absorption may cause nausea, vomiting, and shock.|/SIGNS AND SYMPTOMS/ Potent skin, eye, mucous membrane irritant.|/OTHER TOXICITY INFORMATION/ Immediate skin and eye reactions are not appreciably altered by prolonged washing or attempts at neutralzation when these are commenced within 15 sec after application.|/OTHER TOXICITY INFORMATION/ ... The presence of volatile aliphatic amines ... in human breast milk and amniotic fluid /was measured/ to assess their role in neonatal hypergastrinemia. These volatile nitrogenous amino acid metabolites have been previously demonstrated to stimulate gastrin release in in vivo and in vitro laboratory preparations. ... The present study ... demonstrated that these gastrin-stimulatory volatile amines were present in significant concentrations in breast milk during the first several weeks after parturition and in amniotic fluid. The individual amines that were identified in both human milk and amniotic fluid samples were methylamine, dimethylamine, ethylamine, trimethylamine, propylamine, isobutylamine, and butylamine. This study provides indirect evidence to support the possibility that the hypergastrinemia measured in the fetus/neonate during the period immediately before and after birth may be attributable, in part, to the ingestion of fluid containing high concentrations of gastrin-stimulating amines.

1-butylamine

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, skin, nose, throat; headache; skin flush, burns


Sore throat. Cough. Burning sensation. Headache. Flushing of the face. Vomiting. Dizziness. Shortness of breath. Laboured breathing. Symptoms may be delayed.


MAY BE ABSORBED! Pain. Redness. Blisters. Skin burns.


Pain. Redness. Severe deep burns. Loss of vision.

Eyes, skin, respiratory system

Butylamine Use and Manufacturing

Methods of Manufacturing

The preparation method is to pass butanol, ammonia and hydrogen at 170~200℃ through a Cu-Ni catalyst with clay as the carrier to obtain a mixture of three kinds of amines, namely n-butylamine, di-n-butylamine and tri-n-butylamine, and then carry out the product. Fractional distillation to obtain n-butylamine, di-n-butylamine and tri-n-butylamine products. Reaction equation: C4H9OH+NH3[H2]→C4H9NH2[C4H9OH]→(C4H9)2NH[C4H9OH]→(C4H9)3N or using butanol as the raw material, reacting with hydrogen chloride to produce chlorobutane, the ammonia-containing ethanol, ammonia water Pressurize with chloroprene into the autoclave, stir and heat up to 85~95℃, pressure is 539~637kPa, keep for 6h, cool, after the reaction is completed, heat the reaction liquid to recover ammonia gas, then add hydrochloric acid to pH=3~4, and then recover Ethanol, add alkaline solution to pH=11~12 in this crude liquid, separate the upper layer liquid, and collect the fraction below 95℃ by distillation to divide into n-butylamine product. Reaction equation: C4H9OH+HCl→C4H9Cl+H2OC4H9Cl+NH3[C2H5OH]→CH3(CH2)3NH2+HCl

Uses

Intermediate for pharmaceuticals, dyestuffs, rubber chemicals, emulsifying agents, insecticides, synthetic tanning agents.


Intermediates

Production

1,000,000 - 10,000,000 lb|(1978) 1.86X10+9 G|(1982) 1.11X10+9 G|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1457]|This chemical is listed as a High Production Volume (HPV) (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).

CHEM INT FOR RUBBER-PROCESSING CHEMICALS, (EG, ACCELERATORS, VULCANIZING AGENTS, & ANTIOXIDANTS), 50%; CHEM INT FOR PESTICIDES, 50% (1982)

Agriculture, forestry, fishing and hunting|1-Butanamine: ACTIVE|Aziridines are hydrogenated in the presence of typical hydrogenation catalysts to give alkyl amines.

N-BUTYLAMINE IS DETERMINED IN AIR BY GAS CHROMATOGRAPHY WITH FLAME IONIZATION DETECTOR AFTER ADSORPTION ON H2SO4 TREATED SILICA GEL & DESORPTION WITH 50% METHANOL. METHOD VALIDATED OVER RANGE OF 8.09-35.5 MG/CU M AT ATM TEMP & PRESSURE OF 24 °C & 769 MM HG USING 15-L SAMPLE VOL.|TWENTY-EIGHT DIFFERENT AROMATIC & ALIPHATIC AMINES WERE SEPARATED BY TLC; 20 SOLVENT SYSTEMS WERE EXAMINED.|DETERMINATION OF PRIMARY & SECONDARY AMINES IN WINES AND SOY SAUCE BY HIGH-PERFORMANCE LIQ CHROMATOGRAPHY.|A GC analytical column, alkalized SEPABEAD GHP-1, was prepared to determine the C1-C4 aliphatic amines without interferences of water, and handy SP cartridges impregnated with phosphoric acid were used to perform trace determination of these amines in air samples. The proposed method may be useful in routine analyzing a large number of air samples in studies of air pollution. The recovery of tert-butylamine from the SP cartridge was 93.4%.|For more Analytic Laboratory Methods (Complete) data for N-BUTYLAMINE (9 total), please visit the HSDB record page.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fire Hazards -> Flammable - 3rd degree

Flavoring Agents

Computed Properties

Molecular Weight:73.14
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:73.089149355
Monoisotopic Mass:73.089149355
Topological Polar Surface Area:26
Heavy Atom Count:5
Complexity:13.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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