110-96-3 Usage
Description
Diisobutylamine is a secondary amine that appears as a clear, colorless liquid with an ammonia-like odor. It is insoluble in water and less dense than water, causing it to float on the surface. When burned, it produces toxic oxides of nitrogen. The chemical reactivity of diisobutylamine is similar to other aliphatic amines, with its unshared electron pair on the nitrogen atom making it a strong base that tends to form salts with acids. It can also be nitrosated under acidic conditions, leading to the formation of carcinogenic and mutagenic N-nitrosodiisobutylamine.
Uses
Used in Chemical Research:
Diisobutylamine is used as an achiral amine in the study of the effect on hydrogenation of ethyl pyruvate over a cinchonidine-Pt/Al2O3 catalyst system.
Used in Agricultural Industry:
Diisobutylamine is used as a chemical intermediate for the manufacture of various agricultural products.
Used in Pharmaceutical Industry:
Diisobutylamine is used as a chemical intermediate in the production of several pharmaceutical products.
Production Methods
Diisobutylamine can be produced by the reaction of ammonia and butanol over a
dehydration catalyst at high temperature and pressure (Hawley 1977). Alternatively,
ammonia, butanol, and hydrogen can be passed over a dehydrogenation
catalyst. In 1976, 18,000 tons of diisobutylamine were produced (Schweizer et al
1978). Diisobutylamine is also naturally present in foods and soil.
As with other secondary amines, diisobutylamine can be nitrosated to form the
highly toxic (Olah 1975) N-nitrosodiisobutylamine (Guttenplan 1987; Vlasenko et
al 1981; Spiegeholder et al 1978). Thus, nitrosation of commercial preparations of
diisobutylamine occurs on standing, presumably by reaction with nitrogen oxides
in the air (Spiegelhalder et al 1978) and N-nitrosodiisobutylamine has been found
in various fishery products (Kawabata et al 1974) and other foods (Osborne 1972;
Telling 1972).
Air & Water Reactions
Highly flammable. Sensitive to heat and air. Insoluble in water.
Reactivity Profile
Diisobutylamine can react vigorously with oxidizing materials . 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 of high concentrations of vapor will cause irritation of the respiratory tract and the lungs. Contact with liquid may result in severe skin and eye irritation. Exposure to concentrated vapors may result in corneal edema. Poisonous if swallowed.
Health Hazard
Diisobutylamine is a relatively strong base and is therefore irritating to the eyes,
respiratory tract, and skin. Inhalation of vapors can result in pulmonary edema
following prolonged exposure. Ingestion of liquid can cause severe burning of the
esophagus.
Safety Profile
Poison by ingestion. A
dangerous fire hazard when exposed to heator flame; can react vigorously with oxidizing
materials. To fight fire, use alcohol foam,
CO2, dry chemical. When heated to
decomposition it emits toxic fumes of Nox
Metabolism
There is little information available on the metabolism of diisobutylamine.
Check Digit Verification of cas no
The CAS Registry Mumber 110-96-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 110-96:
(5*1)+(4*1)+(3*0)+(2*9)+(1*6)=33
33 % 10 = 3
So 110-96-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H19N/c1-5-7(3)9-8(4)6-2/h7-9H,5-6H2,1-4H3/p+1/t7-,8-/m1/s1
110-96-3Relevant articles and documents
One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis
Coeck, Robin,De Vos, Dirk E.
supporting information, p. 5105 - 5114 (2020/08/25)
The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).
Colloid and nanosized catalysts in organic synthesis: XVII. Reductive amination of carbonitriles in the presence of supported nickel nanoparticles
Popov, Yu. V.,Mokhov,Latyshova,Panov,Shirkhanyan
, p. 2546 - 2551 (2017/12/26)
Reductive amination of carbonitriles catalyzed by nickel nanoparticles applied onto a solid support in a plug flow reactor in the gas phase or the gas–liquid–solid catalyst system occurs at atmospheric pressure of hydrogen affording the nonsymmetrical secondary or tertiary amines. The effect of the support type on the target product yield and conversion of the substrate has been studied.
Colloid and nanosized catalysts in organic synthesis: XVI.1 Continuous hydrogenation of carbonitriles catalyzed by nickel nanoparticles applied on a support
Popov, Yu. V.,Mokhov,Latyshova,Nebykov,Panov,Pletneva, M. Yu.
, p. 2276 - 2281 (2017/11/24)
Conversion of the starting nitriles and selectivity of the products formation during continuous hydrogenation of various nitriles catalyzed by Ni0/Ceokar-2 have been studied as functions of temperature. Performing the process at temperature 120–260°С has led to the formation of a mixture of products containing di- and trialkylamines as well as the corresponding imines and enamines.
