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Dipropylamine is an organic compound with the formula (CH3CH2CH2)2NH.
Dipropylamine is classified as a secondary amine.
Dipropylamine is a colorless liquid with a "fishy" odor.
CAS: 142-84-7
MF: C6H15N
MW: 101.19
EINECS: 205-565-9
Synonyms
LABOTEST-BB LTBB000411;DI-N-PROPYLAMINE;DIPROPYLAMINE;DPA;DNPA;AURORA KA-7671;DIPROPYLAMINE, 99+%;Rcra waste number U110
Dipropylamine is a precursor to various herbicides such as trifluralin, oryzalin, and vernolate.
Dipropylamine is a colorless, water-white liquid with a strong ammonia-like odor.
Molecularweight= 101.22; Boiling point = 110℃; Freezing/Meltingpoint = 263℃; Vapor pressure= 29.8 mmHg at 25℃;Flash point = 17℃; Autoignition temperature= 299℃.Hazard Identification (based on NFPA-704 M RatingSystem): Health 3, Flammability 4, Reactivity
Dipropylamine is an organic compound classified as a secondary amine, characterized by the presence of two propyl groups attached to a nitrogen atom.
Dipropylamine's molecular formula is C6H15N, and it typically appears as a colorless to pale yellow liquid with a distinctive amine odor.
Dipropylamine is soluble in organic solvents and exhibits low solubility in water.
Dipropylamine has a relatively low boiling point and a moderate flash point, indicating flammability under certain conditions.
Dipropylamine is used in various applications, including as a solvent, a chemical intermediate in the synthesis of pharmaceuticals, and in the production of agricultural chemicals.
Additionally, Dipropylamine can act as a catalyst in certain chemical reactions.
Due to its amine nature, Dipropylamine can participate in hydrogen bonding, influencing its reactivity and interactions with other substances.
Safety precautions are necessary when handling Dipropylamine, as it can be irritating to the skin, eyes, and respiratory system.
Proper storage and disposal methods should be followed to mitigate environmental and health risks.
Dipropylamine is a flammable, highly toxic, corrosive amine.
Dipropylamine occurs naturally in tobacco leaves and artificially in industrial wastes.
Exposure can cause excitement followed by depression, internal bleeding, dystrophy, and severe irritation.
Dipropylamine appears as a clear colorless liquid with an ammonia-like odor.
Flash point 30°F. Less dense than water. Vapors heavier than air.
Toxic oxides of nitrogen produced during combustion.
Dipropylamine appears as a clear colorless liquid with an ammonia-like odor.
Flash point 30°F.
Less dense than water. Vapors heavier than air.
Toxic oxides of nitrogen produced during combustion.
Dipropylamine Chemical Properties
Melting point: -63 °C
Boiling point: 105-110 °C(lit.)
Density: 0.738 g/mL at 25 °C(lit.)
vapor pressure: 38 hPa (20 °C)
refractive index: n20/D 1.4049(lit.)
Fp: 39 °F
storage temp.: Store below +30°C.
solubility: 35g/l (experimental)
pka: pK1:10.91(+1) (25°C)
form: Liquid
color: Clear
explosive limit: 1.8-9.3%(V)
Water Solubility: soluble
Merck: 14,3343
BRN: 505974
Henry's Law Constant: 2.0×10-1 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
Dielectric constant: 2.9（21℃）
Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents.
InChI: 1S/C6H15N/c1-3-5-7-6-4-2/h7H,3-6H2,1-2H3
InChIKey: WEHWNAOGRSTTBQ-UHFFFAOYSA-N
LogP: 1.33 at 23℃
Dissociation constant: 11
CAS DataBase Reference: 142-84-7(CAS DataBase Reference)
NIST Chemistry Reference: 1-Propanamine, n-propyl-(142-84-7)
EPA Substance Registry System: Dipropylamine (142-84-7)
Dipropylamine, like the other short chain aliphatic amines, is a very strong base, its reactivity being governed by the unshared electron pair on the nitrogen atom.
Dipropylamine forms a hydrate with water.
The amine also can react with inorganic or organic nitrites under acidic conditions and possibly by reaction with nitrogen oxides from the air to form the highly mutagenic and carcinogenic N-nitrosodipropylamine (ATSDR 1979; Olah et al; Scanlan 1983).
Uses
Dipropylamine is a useful reagent for the preparation of perylene derivatives for photosensitive fluorescent resins.
Industrial uses
Dipropylamine is used in the rubber industry and as a chemical intermediate in the manufacture of the herbicides S-ethyl-di-n-propylthiocarbamate and S-propyl di-n-propylthiocarbamate.
Dipropylamine also is employed in the purification of perfluoro compounds to convert the incompletely fluorinated impurities to solids which are then removed by filtration.
In 1984, U.S. production was 41 million pounds.
Production Methods
Dipropylamine is manufactured by reaction of propanol and ammonia over a dehydration catalyst at high temperature and pressure (HSDB 1989).
Alternatively, propanol and ammonia can be combined with hydrogen over a dehydrogenation catalyst.
In each instance, the resulting mixture of primary, secondary, and tertiary amines can be separated by continuous distillation and extraction (Schweizer et al 1978).
Dipropylamine is a natural component of vegetables, fish, fruits, and other foods (Mohri 1987) and of tobacco products (WHO 1987).
Dipropylamine also is found in human urine (Audunsson 1988), waste water lagoons (Guzewich et al 1983) and in workplace air (Simon and Lemacon 1987).
The toxic compound, N-nitrosodipropylamine, can be produced inadvertently by nitrosation of n-dipropylamine during various manufacturing processes that use the diamine (ATSDR 1989).
The nitrosamine, therefore, occurs as an impurity in some dinitroaniline pesticides and rubber products.
Dipropylamine also is found in various foodstuffs including cheese, cured meats, cooked fish and alcoholic beverages, apparently by reaction of n-dipropylamine with the preservative sodium nitrite (ATSDR 1979; Gross and Newberne 1977; Scanlan 1983).
Reactivity Profile
Dipropylamine 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.
Health Hazard
Inhalation causes severe coughing and chest pain due to irritation of air passages; can-cause lung edema; may also cause headache, nausea, faintness, and anxiety.
Ingestion causes irritation and burning of mouth and stomach.
Contact with eyes causes severe irritation and edema of the cornea.
Contact with skin causes severe irritation.
Inhalation of dipropylamine vapors can result in severe coughing and chest pain due to irritation of airways.
Transient symptoms of exposure may include headache, nausea, faintness, and anxiety.
Prolonged breathing of vapors may result in lung edema.
Dipropylamine also can cause severe irritation and edema of the cornea.
A review of the toxicity of dipropylamine has been prepared (Anon 1987).
