2050-92-2

Usage

Uses

Used in Organic Syntheses:
Diamylamine is used as a reagent in organic syntheses for the production of various chemicals and compounds. Its strong basic nature allows it to participate in various chemical reactions, making it a versatile component in the synthesis process.
Used as a Solvent:
Diamylamine is used as a solvent for oils, resins, and some cellulose esters. The introduction of the amyl group imparts oil solubility to otherwise oil-insoluble substances, making it a valuable solvent in the chemical industry.
Used as a Rubber Accelerator:
In the rubber industry, Diamylamine is used as a rubber accelerator, enhancing the rate of vulcanization and improving the overall properties of the rubber.
Used as a Corrosion Inhibitor:
Diamylamine is employed as a corrosion inhibitor, protecting metals from corrosion and extending the life of equipment and structures in various industries.
Used in Flotation Reagents:
In the mining industry, Diamylamine is used as a component in flotation reagents, aiding in the separation of valuable minerals from waste materials.
Used in Dye Production:
Diamylamine is utilized in the production of dyes, contributing to the development of vibrant and stable colorants for various applications.
Used in the Synthesis of Aluminophosphate Material:
Diamylamine is employed as an organic additive in the synthesis of pure AlPO4-H2 (aluminophosphate material), which has potential applications in catalysis and gas adsorption.
Used in the Synthesis of Boron Nitride Ceramic Fibers:
Diamylamine was used in the synthesis of a new melt-spinnable polymeric precursor to boron nitride ceramic fibers, which have potential applications in high-temperature and high-strength materials.
Used in Nonaqueous Capillary Electrophoresis:
Diamylamine was used to compose a background electrolyte for the separation of linear alkylbenzene sulfonates by nonaqueous capillary electrophoresis, a technique used for the separation and analysis of various compounds.
Used as a Cockroach Repellent:
Diamylamine is also used as a cockroach repellent, taking advantage of its ammonia-like odor to deter these pests.

Production Methods

Diamylamine is manufactured by the same processes as n-amylamine by reaction of amyl chloride with ammonia and then separated from the amylenes and amyl alcohol by steam distillation (Hawley 1977). It also can be synthesized by amination of alkyl halides at high temperature and pressure (Schweizer et al 1978). The commercial product may be a mixture of amyl isomers (HSDB 1989).

Air & Water Reactions

Flammable. Sensitive to air and heat. Slightly soluble in water.

Reactivity Profile

Diamylamine neutralizes acids to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides.

Health Hazard

TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn 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.

Health Hazard

Diamylamine is a strong eye, skin, and respiratory irritant owing to its basicity (HSDB 1989). Vapor exposure results in irritation of the nose and throat with distressed breathing and coughing. Prolonged exposure may lead to pulmonary edema. Direct skin contact can cause secondary burns.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily 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 and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Poison by inhalation, ingestion, and skin contact. A severe skin irritant. See also AMINES. Flammable liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx.

Metabolism

In contrast to n-amylamine, little information is available on diamylamine metabolism, particularly with respect to its suitability as a substrate for the amine oxidases. Generally, the rate of oxidation of secondary amines by monoamine oxidase is slower than that of primary amines (Beard and Noe 1981). In agreement, Yamada et al (1965) demonstrated that crystalline amine oxidase prepared from Aspergillus niger oxidized diamylamine very slowly with respect to n-amylamine. As with other secondary aliphatic amines, the propensity of diamylamine to form nitrosamines is of interest. It has been shown that treatment of diamylamine with nitrous acid in dilute aqueous solution gave optimum nitrosamine formation between pH 1 and 3, corresponding to stomach conditions (Sander et al 1968). When rats were fed a diet supplemented with sodium nitrite and secondary amines of low basicity, synthesis of nitrosamines in the stomach was observed. Malignant tumors arising through formation of nitrosamines in the stomach was demonstrated only when nitrite was present in the stomach concomitantly with secondary amines which readily formed carcinogenic nitrosamines.

Upstream product

• 5775-76-8 valeraldoxime 
• 110-59-8 pentanonitrile 
• 547751-03-1 hexanedioic acid bis-pentylamide 
• 6539-59-9 N-benzyl-N-pentylpentan-1-amine 
• 110-58-7 n-Pentylamine 
• 110-89-4 piperidine 
• 41495-45-8 1-Pentyl-1-hexylamine 
• 10324-58-0 1-pentylpiperidine 
• 7335-01-5 1-hexylpiperidine 
• 106-98-9 1-butylene 
• 51-80-9 bis-(dimethylamino)methane 
• 693-03-8 n-butyl magnesium bromide 
• 111184-76-0 bis(benzotriazol-1-ylmethyl)amine 
• 111-26-2 hexan-1-amine 

Downstream Products

• 100527-91-1 3-Dipentylamino-propionitril 
• 2567-60-4 N,N-dipentyl-2-chloroacetamide 
• 26598-27-6 N,N-dipentylformamide 
• 5439-40-7 dichloro-acetic acid dipentylamide 
• 621-77-2 tripentylamine 
• 37008-82-5 N,N-dipentylcyanamide 
• 110-59-8 pentanonitrile 
• 13256-06-9 N-nitrosodiamylamine 
• 110-58-7 n-Pentylamine 
• 2644-26-0 ethyl dipentylglycinate 
• 102-80-7 N¹,N¹,N²,N²-tetrapentylethane-1,2-diamine 
• 32529-36-5 2-Chloro-benzene-1,4-disulfonic acid 4-(acetyl-amide) 1-dipentylamide 
• 67141-63-3 2-(2,4-Dichloro-phenoxy)-N,N-dipentyl-acetamide 
• 16238-16-7 N,N-Dipentylacetamide 

Relevant academic research and scientific papers

Hydrogenation of Aliphatic Nitriles to Primary Amines over a Bimetallic Catalyst Ni25.38Co18.21/MgO–0.75Al2O3 Under Atmospheric Pressure

Abstract: A mixed oxide supported bimetallic catalyst Ni25.38Co18.21/MgO–0.75Al2O3 was readily prepared and found to be efficient in the hydrogenation of valeronitrile (VN) to amylamine (AA) under atmospheric pressure. Under the optimal conditions: H2 to VN molar ratio of 4:1, NH3 to VN molar ratio of 3:1, reaction temperature of 130?°C and residence time of 5?s, the conversion of VN reached 100% with a AA yield of 70.8%, and a diamylamine (DAA) yield of 25.9%. This catalyst was also active in the hydrogenation of other low carbon aliphatic nitriles to their corresponding primary amines. The characterization results revealed that the catalyst had the properties of large surface area, uniform and fine dispersion of metal particles in the form of Ni/Co alloy with synergy effect between the two metals, which endowed the catalyst with good catalytic performances in the hydrogenation reaction of aliphatic nitriles. Graphic Abstract: [Figure not available: see fulltext.]

Selective Synthesis of Primary Amines from Nitriles under Hydrogenation Conditions

The hydrogenation of aliphatic nitriles over Pd/C, Pd/Al2O3, and Pd?Au/Al2O3 catalysts were evaluated for the selective hydrogenation of aliphatic nitriles to the corresponding primary amines. The highest selectivity (>99%) toward primary amines was achieved when the reaction was carried out in acetic acid using 10 mol% of 25% Pd-5% Au/Al2O3 under relatively low hydrogen pressure (0.8 MPa). Characterization of the catalysts by XRD, CO adsorption experiments, and EXAFS revealed that the excellent selectivity of 25% Pd-5% Au/Al2O3 toward the synthesis of primary amines is determined by the electronic properties and/or the surface structure resulting from alloying Pd with Au. (Figure presented.).

Hydrogenolysis of Amide Acetals and Iminium Esters

Amide acetals and iminium esters were hydrogenated into amines under very mild reaction conditions over common hydrogenation catalysts. This finding provides a new strategy for the selective reduction of amides. The synthetic utility of this approach was demonstrated by the selective reduction of amides bearing ester and nitrile groups.

Catalyst-Dependent Selective Hydrogenation of Nitriles: Selective Synthesis of Tertiary and Secondary Amines

In the presence of palladium on carbon (Pd/C) as a catalyst, hydrogenation of aliphatic nitriles in cyclohexane efficiently proceeded at 25-60 °C under ordinary hydrogen gas pressure to afford the corresponding tertiary amines. However, the use of rhodium on carbon (Rh/C) led to the highly selective generation of secondary amines. Hydrogenation of aromatic nitriles and cyclohexanecarbonitrile selectively produced secondary amines in the presence of either Pd/C or Rh/C.

Continuous Production of Dialkylamines by Selective Hydrogenation of Nitriles on a Nickel-Zeolite Catalyst

Hydrogenation of aliphatic nitriles in the presence of nickel supported by NaX zeolite was studied. The data obtained were used to develop a continuous method for obtaining dialkylamines with the yield of the target product of up to 98%.

Colloid and nanosized catalysts in organic synthesis: XVI.1 Continuous hydrogenation of carbonitriles catalyzed by nickel nanoparticles applied on a support

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.

Cobalt-Catalyzed Synthesis of Aromatic, Aliphatic, and Cyclic Secondary Amines via a "hydrogen-Borrowing" Strategy

The replacement of precious metals with inexpensive, less toxic, and earth-abundant elements in typical noble-metal-mediated organic transformations is a major goal in current synthetic chemistry and industries. The metal-catalyzed N-alkylation of amines with other amines through a "hydrogen-borrowing" principle represents a green and atom-economical reaction for the synthesis of secondary amines. However, catalysts developed thus far that are effective for this process remain quite scarce and are only limited to a few ruthenium and iridium complexes. In this work, we present a cobalt-catalyzed selective alkylation of amines with amines to synthesize a large variety of secondary amines. A range of amine substrates have been converted to the corresponding products through hetero- or homocoupling between amines. Cyclic sec-amines are also achieved from diamine precursors as rare examples.

Catalytic Hydrogenation for the Preparation of Amines from Amide Acetals, Ketene N,O-Acetals or Ester Imides

The present invention relates to a process for the preparation of amines, comprising the following steps: Reaction of a (i) amide acetal of the general formula (I), or (ii) ketene N,O-acetal of the general formula (II), or (iii) ester imide of the general formula (III) with H2 in the presence of a hydrogenation catalyst, where catalyst and amide acetal or ketene N,O-acetal or ester imide are used in a molar ratio of from 1:10 to 1:100 000 and where a hydrogen pressure of from 0.1 bar to 200 bar is established and where a temperature in the range of from 0° C. to 250° C. is established.

Iron-catalyzed Cα-H oxidation of tertiary, aliphatic amines to amides under mild conditions

De novo syntheses of amides often generate stoichiometric amounts of waste. Thus, recent progress in the field has focused on precious metal catalyzed, oxidative protocols to generate such functionalities. However, simple tertiary alkyl amines cannot be used as starting materials in these protocols. The research described herein enables the oxidative synthesis of amides from simple, noncyclic tertiary alkyl amines under synthetically useful, mild conditions through a biologically inspired approach: Fe-catalyzed Cα-H functionalization. Mechanistic investigations provide insight into reaction intermediates and allow the development of a mild Cα-H cyanation method using the same catalyst system. The protocol was further applied to oxidize the drug Lidocaine, demonstrating the potential utility of the developed chemistry for metabolite synthesis. Let′s iron it out! The title reaction enables the oxidative synthesis of amides directly from tertiary, noncyclic alkyl amines under synthetically useful, mild conditions through a biologically inspired approach employing oxidative iron catalysis. Mechanistic studies suggest that hemiaminals are likely intermediates in this reaction and that the catalytic system can be employed for other Cα-H oxidations of amines.

PROCESS FOR PREPARING AMINES FROM ALCOHOLS AND AMMONIA

The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.