142-84-7 Usage
Description
Dipropylamine is a clear, colorless liquid with an ammonia-like odor. It is less dense than water and has a flash point of 30°F. Its vapors are heavier than air, and it can produce toxic oxides of nitrogen during combustion. As a strong base, its reactivity is governed by the unshared electron pair on the nitrogen atom, allowing it to form a hydrate with water. Dipropylamine can also react with inorganic or organic nitrites under acidic conditions and potentially with nitrogen oxides from the air to form the highly mutagenic and carcinogenic N-nitrosodipropylamine.
Uses
Used in the Rubber Industry:
Dipropylamine is used as a chemical intermediate in the rubber industry for various applications, contributing to the production and enhancement of rubber products.
Used in the Manufacture of Herbicides:
Dipropylamine is used as a chemical intermediate in the production of the herbicides S-ethyl-di-n-propylthiocarbamate and S-propyl di-n-propylthiocarbamate, which are utilized in the agricultural industry for weed control.
Used in the Purification of Perfluoro Compounds:
Dipropylamine is employed in the purification process of perfluoro compounds, where it helps convert incompletely fluorinated impurities into solids. These solids are then removed by filtration, ensuring the purity of the final product.
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). It 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. N-nitrosodipropylamine 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).
Air & Water Reactions
Highly flammable. Soluble in water.
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.
Health Hazard
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).
Fire Hazard
Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fires.
Safety Profile
Poison by ingestion.
Moderately toxic by shin contact and
inhalation. A skin irritant. A very dangerous
fire hazard, when exposed to heat or flame.
Can react with oxidizers. Explosion hazard
is unknown. Keep away from heat and open
flame. To fight fire, use foam, CO2, dry
chemical. When heated to decomposition it
emits toxic fumes of NOx,. See also
AMINES
Metabolism
There is little information available on the metabolism and disposition of dipropylamine
in biological systems. The available evidence suggests that dipropylamine
is not a substrate for monoamine oxidase, but rather is inhibitory. Valiev (1974)
administered dipropylamine intraperitoneally to rats and reported it to be moderately
inhibitory to liver monoamine oxidase. Previous work by this author demonstrated
that lethal doses of dipropylamine and other secondary and tertiary amines
significantly inhibited rat liver monoamine oxidase activity (Valiev 1968).
The carcinogenic N-nitrosodipropylamine has been detected in the stomach
when dipropylamine (present in fish, vegetables and fruit juices) comes in contact
with nitrite, which is often used as a food additive in meats and smoked fish
(HSDB 1989). Further metabolism of the carcinogen N-nitrosodipropylamine
product formed upon nitrosation of dipropylamine is required to form a highly
electrophilic carbonium ion capable of alkylating DNA, etc. (Archer 1981).
Check Digit Verification of cas no
The CAS Registry Mumber 142-84-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 2 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 142-84:
(5*1)+(4*4)+(3*2)+(2*8)+(1*4)=47
47 % 10 = 7
So 142-84-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H15N/c1-3-5-7-6-4-2/h7H,3-6H2,1-2H3/p+1
142-84-7Relevant articles and documents
Semiconductor Photocatalysis.ZnS-Catalyzed Photoreduction of Aldehydes and Related Derivatives: Two-Electron-Transfer Reduction and Relationship with Spectroscopic Properties
Yanagida, Shozo,Ishimaru, Yoshiteru,Miyake, Yoshio,Shiragami, Tsutomu,Pac, Chyongjin,et al.
, p. 2576 - 2582 (1989)
Photocatalytic activity and spectroscopic properties of ZnS suspensions for the two-electron reduction of aldehydes or related compounds in aqueous medium are described.The ZnS suspension (ZnS-0) prepared by cooling from aqueous ZnSO4 and Na2S solutions catalyzes photoredox reactions of acetaldehyde, giving ethanol without much H2 evolution as a two-electron-reduction product, and acetic acid, biacetyl, and acetoin as oxidation products.When the ZnS-0 suspension is refluxed (giving ZnS-100) or dried to powder, the resulting ZnS shows an increased activity for H2 evolution but a decreased activity for the two-electron reduction.The two-electron photoreduction is ascribed to the sequential transfer of active electrons in the conduction band of defect-free aggregates of ZnS microcrystallites (quantized ZnS).This mechanism is supported by product analysis, energetics at ZnS interfaces, the sharp and blue-shifted onset of absorption and excitation spectra, and the long-life band gap emission of the active ZnS-0 suspension.UV, emission, and ESR spectra, as well as the enhancement of the particle size and crystallinity, suggest that the activity change observed after heating or drying to powder is due to the formation of surface states which may trap active electrons.This interpretation is also supported by the generated activity of ZnS-100 for the H2 photoevolution under >350-nm irradiation.ZnS photocatalysis under >350-nm irradiation and relationship with spectroscopic properties are also discussed.
A New and Convenient Process for Separation of Carbon Monoxide
Sonoda, Noboru,Miyoshi, Noritaka,Tsunoi, Shinji,Ogawa, Akiya,Kambe, Nobuaki
, p. 1873 - 1876 (1990)
A new method for the efficient separation of carbon monoxide from a binary mixture of carbon monoxide and hydrogen has been established by use of a selenium/secondary amine reaction system.This system consists of the selective uptake of carbon monoxide by the reaction with selenium and secondary amines to form the corresponding ammonium carbamoselenoates (1) in solution and the release of carbon monoxide by thermolysis of 1 into starting components.The amount of separated carbon monoxide was stoichiometric and the purity was higher than 99.9percent.
Highly selective synthesis of primary amines from amide over Ru-Nb2O5 catalysts
Guo, Wanjun,Guo, Yong,Jia, Hongyan,Liu, Xiaohui,Pan, Hu,Wang, Yangang,Wang, Yanqin,Xia, Qineng
supporting information, (2021/12/22)
Amines are an important class of compounds in natural products and medicines. The universal availability of amides provides a potential way for the synthesis of amines. Herein, Ru/Nb2O5 catalyst is demonstrated to be highly efficient and stable for the selective hydrogenation of propionamide to propylamine (as a model reaction), with up to 91.4% yield of propylamine under relatively mild conditions. Results from XPS analyses, CO chemisorption, TEM images and DRIFTS spectra revealed that the unique properties of Nb2O5 can effectively activate the C=O group of amides, and the smaller Ru particles on Nb2O5 could further promote the activation, leading to superior catalytic performance of Ru/Nb2O5 for amide hydrogenation. Meanwhile, reducing the surface acidity of Nb2O5 can greatly inhibit the side reactions to by-products, and further enhance the selectivity to amine. Moreover, this catalytic system is also applicable for the hydrogenation of a variety of amides and provides high potential for the industrial production of primary amines from amides.
Sustainable hydrogenation of aliphatic acyclic primary amides to primary amines with recyclable heterogeneous ruthenium-tungsten catalysts
Coeck, Robin,Berden, Sarah,De Vos, Dirk E.
supporting information, p. 5326 - 5335 (2019/10/11)
The hydrogenation of amides is a straightforward method to produce (possibly bio-based) amines. However current amide hydrogenation catalysts have only been validated in a rather limited range of toxic solvents and the hydrogenation of aliphatic (acyclic) primary amides has rarely been investigated. Here, we report the use of a new and relatively cheap ruthenium-tungsten bimetallic catalyst in the green and benign solvent cyclopentyl methyl ether (CPME). Besides the effect of the Lewis acid promotor, NH3 partial pressure is identified as the key parameter leading to high primary amine yields. In our model reaction with hexanamide, yields of up to 83% hexylamine could be achieved. Beside the NH3 partial pressure, we investigated the effect of the catalyst support, PGM-Lewis acid ratio, H2 pressure, temperature, solvent tolerance and product stability. Finally, the catalyst was characterized and proven to be very stable and highly suitable for the hydrogenation of a broad range of amides.