107-12-0

Usage

Uses

1. Chemical Intermediate:
Propionitrile is used as a chemical intermediate in various organic syntheses, such as the Houben-Hoesch reaction, and for the production of pharmaceuticals like ketoprofen and fragrances.
2. Solvent:
Propionitrile serves as a solvent in multiple applications, including:
a. Extraction solvent for fatty acids, oils, and unsaturated hydrocarbons.
b. Solvent for spinning and casting processes.
c. Removing agent of coloring matters and aromatic alcohols.
d. Non-aqueous solvent for titrations and for inorganic salts.
e. Recrystallization of steroids.
3. Industrial Applications:
a. Used in the chemical industry as a selective solvent and in petroleum refining.
b. Employed experimentally as an ulcerogen.
4. Dielectric Fluid:
Propionitrile is utilized as a dielectric fluid in various industrial applications.
5. Stabilizer:
It acts as a stabilizer for chlorinated solvents.
6. Catalyst Component:
Propionitrile is a component of transition-metal complex catalysts, contributing to their catalytic activity.
7. By-product Formation:
It is formed as a by-product of the electrodimerization of acrylonitrile to adiponitrile, which can be further utilized in various chemical processes.

Production Methods

Propionitnle may be prepared by dehydration of propionamide (or propionic acid plus ammonia) or by distilling ethyl sulfate and concentrated aqueous KCN. It also is formed as a byproduct of the electrohydrodimerization of acrylonitrile or by the hydrogenation of acrylonitrile with the use of copper, rhodium or nickle catalysts . U.S. production is estimated for 1980 to range between 10-15 million pounds.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Propionitrile is incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents. After refluxing for 24 hours at 221°F, a mixture of Propionitrile with N-bromosuccinimide exploded.

Hazard

Toxic by ingestion and inhalation. Flammable, dangerous fire risk.

Health Hazard

Propionitrile is highly toxic. This super toxic compound has a probable oral lethal dose in humans of less than 5 mg/kg or a taste (less than 7 drops) for a 70 kg (150 lb.) person. It is a mild to moderate skin and eye irritant.

Health Hazard

Reports of human toxicity data for propionitrile have not been found in the literature. However, Deichman indicated that propionitrile is rapidly absorbed through the skin and that it is one of the most toxic organic cyanides known. Clinical symptoms are characterized as loss of conciousness, salivation, nausea and vomiting. Hypopnea and dyspnea with bitter almond odor in breath and vomitus also were observed. Due to high concentrations of oxy- and cyanohemoglobin in venous blood, pink coloration of the skin was observed .

Health Hazard

Propionitrile is a moderate to highly toxic compound, an eye irritant, and a teratomer. The toxic symptoms are similar to acetonitrile. However, the acute inhalation toxicity is greater than that associate with acetonitrile. Willhite (1981) reported a median lethal concentration of 163 ppm in male mice exposed for 60 minutes. By comparison, acetonitrile and butyronitrile exhibited median lethal concentrations of 2693 and 249 ppm, respectively. The toxic routes are inhalation, ingestion, and absorption through skin. The target organs are kidney, liver, central nervous system, lungs, and eyes. Inhalation of 500 ppm for 4 hours was lethal to rats. When administered intraperitoneally to mice, it caused corneal damage, ataxia, and dyspnea. The acute oral toxicity of Propionitrile was found to be moderately high in rodents. LD50 value, oral (mice): 36 mg/kg Scolnick et al. (1994) have reported two cases of human intoxication from propionitrile. In the more severe case, the victim was comatose, acidotic, and hypotensive. Sodium nitrite/sodium thiosulfate therapy followed by treatment with hyperbaric oxygen at 2 atm was effective. In the second case, the symptoms were nausea, dizziness, and headache. The measured blood cyanide concentration in this case was 3.5μg/ml and the concentration of propionitrile at work site shortly after the exposure was found to be 77.5 mg/m3 in the air. The authors have suggested the use of hyperbaric oxygen as a valuable adjunct therapy in addition to the cyanide antidote kit for all nitrile poisoning. Propionitrile exhibited teratogenic effects in hamsters. Intraperitoneal administration of 238 mg/kg caused cytological changes in embryo and developmental abnormalities in the central nervous system. There is no report of any cancer-causing effects of Propionitrile in animals or humans.

Fire Hazard

When heated to decomposition, Propionitrile emits toxic fumes of nitrogen oxides and cyanide. Propionitrile is a flammable/combustible material and may be ignited by heat, sparks or flames. Vapors may travel to a source of ignition and flash back. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Generates cyanide ions. Poisonous on contact with acids. stable, but may become unstable at elevated temperatures and pressures.

Safety Profile

Poison by ingestion, skin contact, intravenous, and intraperitoneal routes. Moderately toxic by inhalation. Experimental teratogenic effects. Other experimental reproductive effects. A skin and eye irritant. Dangerous fire hazard when exposed to heat, flame (sparks), oxidners. Mixture with N- bromosuccinimide may explode when heated. To fight fire, use water spray, foam, mist, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx and CN-. Used as a solvent in petroleum refining, and as a raw material for drug manufacture. See also NITRILES.

Potential Exposure

Used as a solvent in petroleum refin- ing, as a chemical intermediate; a raw material for drug manufacture; and a setting agent.

Shipping

UN2404 Propionitrile, Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poisonous material. UN1992 Flammable liquids, toxic, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Shake the nitrile with dilute HCl (20%), or with conc HCl until the odour of isonitrile has gone, then wash it with water, and aqueous K2CO3. After a preliminary drying with silica gel or Linde type 4A molecular sieves, it is stirred with CaH2 until hydrogen evolution ceases, then decant and distil from P2O5 (not more than 5g/L, to minimise gel formation). Finally, it is refluxed with, and slowly distilled from CaH2 (5g/L), taking precautions to exclude moisture. [Beilstein 2 IV 728.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlo- rine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides., reducing agents. Hydrogen cyanide is produced when propionitrile is heated to decomposition. Reacts with acids, steam, warm water; producing toxic and flammable hydrogen cyanide fumes. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompati- ble with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids .

Waste Disposal

Alcoholic NaOH followed by calcium hypochlorite may be used, as may incineration . Consult with environmental regulatory agencies for guid- ance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

InChI:InChI=1/C3H5N/c1-2-3-4/h2H2,1H3

Upstream product

• 71-23-8 propan-1-ol 
• 102-69-2 tri-n-propylamine 
• 74-96-4 ethyl bromide 
• 151-50-8 potassium cyanide 
• 64-67-5 diethyl sulfate 
• 187737-37-7 propene 
• 74-98-6 propane 
• 60-29-7 diethyl ether 
• 74-90-8 hydrogen cyanide 
• 29443-39-8 methyl ethyl ketone hydrazone 
• 543-67-9 n-propyl nitrite 
• 74-85-1 ethene 
• 75-00-3 chloroethane 
• 460-19-5 ethanedinitrile 

Downstream Products

• 30805-19-7 1,3,5-tripropionylperhydro-1,3,5-triazine 
• 6301-77-5 2-methyl-4-[2]pyridyl-2-(2-[2]pyridyl-ethyl)-butyronitrile 
• 3592-81-2 N-propylcyclohexylamine 
• 13182-64-4 2-Isopropyl-3H-quinazolin-4-one 
• 33802-51-6 α-methyl-β-phenylpropionitrile 
• 3137-64-2 2-ethyl-3H-quinazolin-4-one 
• 18936-17-9 2-methylbutanenitrile 
• 80606-31-1 2-methyl-2-propylpentanenitrile 
• 6339-13-5 2-methyl-Pentanenitrile 
• 19264-34-7 N-acetylpropionamide 
• 4468-47-7 2-methyl-3-oxo-butyronitrile 
• 55324-06-6 4-methyl-5-phenyl-1H-1,2,3-triazole 
• 13960-36-6 5-methyl-2,6-diphenyl-pyrimidin-4-ylamine 
• 53094-22-7 3-amino-2-methyl-3-phenyl-acrylonitrile 

Related news

Study of thermodynamic properties of binary mixtures of Propionitrile (cas 107-12-0) with dimethylsulfoxide (or diethylsulfoxide) at temperatures from (298.15 to 323.15)K08/18/2019

In this work the thermodynamic properties such as volumetric and viscosity properties of binary mixtures of propionitrile with dimethylsulfoxide (or diethylsulfoxide) have been investigated with the use of density and viscosity measurements over the full range of compositions at temperatures fro...detailed

Relevant academic research and scientific papers

Application of the Water-gas Shift Reaction. III. Reduction of Oxidized Nitrogen Compounds with CO and H2O Catalyzed by (BPh4)2

The ruthenium(II) complex, 4>(BPh4)2 (cod=1,5-cyclooctadiene, py=pyridine) has been shown to catalyze the reduction of oxidized nitrogen compounds with CO and H2O.In this reaction, primary, secondary, and tertiary nitroalkanes are converted into amides, ketones, and amines, respectively.Nitrosobenzene and picoline N-oxides are also reduciable to amines in good yields.

Selective Dehydrogenation of Alkylamines to Nitriles over Metal Oxide Catalysts

Decompositions of alkylamines over ZrO2, SiO2-Al2O3, and MgO were examined in a closed recirculation reactor.ZrO2 showed the highest activities and selectevities for the formation of nitriles, especially in di- and trialkylamine decomposition.In contrast, SiO2-Al2O3 catalyzed dealkylation and deamination reactions exclusively.MgO exhibited high selectivity for the dehydrogenation of primary alkylamine.The high activity of ZrO2 is attributed to its acid-base bifunctional properties.

Preparation of Highly Active Hydrogenation Catalyst by Immobilization of Polymer-Protected Colloidal Rhodium Particles

Colloidal dispersion of rhodium protected by copolymer of mathyl acrylate and N-vinyl-2-pyrrolidone is treated with polyacrylamide gel having amino groups, resulting in immobilization of the rhodium particles onto the gel.The gel-immobilized rhodium particles exhibit 2-22 fold larger catalytic activities than a rhodium carbon catalyst for hydrogenation of olefins at 30 deg C under 1 atm.

Calixarene-Catalyzed Generation of Dichlorocarbene and Its Application to Organic Reactions: The Catalytic Action of Octopus-Type Calixarene

The dichlorocarbene generation reaction from CHCl3 and solid KOH in CH2Cl2 was catalyzed by the p-t-butylcalixarene derivative 1 which bears six 3,6,9-trioxadecyl substituents on the phenolic oxygens.Dichlorocarbene generated by this method reacted efficiently with alkenes and amides to give dichlorocyclopropane derivatives and nitriles, respectively, in high yields.The reaction with alkadiene having isolated double bonds gave mixtures of the mono- and bis-dichlorocarbene adducts, but the monoadduct formation always predominated.The catalytic action of the calixarene and the reactivity features of dichlorocarbene generated by the above procedure are discussed on the basis of kinetic measurements.They are also compared with those of the 18-crown-6-catalyzed reactions.

Study on the conversion of glycerol to nitriles over a Fe 19.2K0.2/γ-Al2O3 catalyst

An Fe19.2K0.2/γ-Al2O3 catalyst for the catalytic amination of glycerol to propionitrile was prepared. Acetonitrile as a major product was obtained over this catalyst from the amination of glycerol. Additionally, propionitrile, ethylene and propylene were also obtained. The parameters influencing the catalyst performance were studied thoroughly, and an optimised process for the amination of glycerol to acetonitrile and propionitrile over the catalyst was obtained. Under the optimised conditions, which were a reaction temperature of 525 °C, an atmospheric pressure with an ammonia/glycerol molar ratio of 8:1 and GHSV of 1338 h-1, the total yield of acetonitrile and propionitrile was 58.4%, and the converted amount of glycerol over one gram of catalyst reached 0.42 g h-1. The catalyst was characterised by XRD, XPS, TEM and IR of the adsorbed pyridine. The characterisation results indicated that the dehydration reaction in the tandem reaction mainly occurred on the Lewis acid sites and revealed that both Fe2O3 and Fe 3O4 are active species for the dehydrogenation of imines to nitriles, but the former is more active than the latter. It also revealed that the catalyst deactivation was due to carbon deposits, the transformation of Fe2O3 to the Fe3O4 phase, as well as agglomeration of the Fe2O3 or Fe3O 4 phase during the catalytic run and regeneration process.

Thermal decomposition of 4-methylpyrimidine. Experimental results and kinetic modeling

The decomposition of 4-methylpyrimidine was studied behind reflected shock waves in a pressurized driver single-pulse shock tube at 1160-1330 K and overall densities of ～ 3 × 10-5 mole/cc. A plethora of decomposition products, both with and without nitrogen, (HCN, CH3CN, C2H3CN, CH4, C2H6, C2H4, etc.) was found in the post-shock mixtures. The attack of methyl radicals on the methyl group in 4-methylpyrimidine produced CH4, which was a major product among the species not containing nitrogen, leaving the radical 4-methylene pyrimidyl. The H atoms and methyl radicals initiated a chain mechanism by abstraction of an H atom from the methyl group and by dissociative attachment of an H atom and removal of a methyl group from the ring. The decomposition mechanism was discussed.

Synergistic Effects of Superbasic Catalysts on the Selective Formation of Acrylonitrile via Oxidative Methylation of Acetonitrile with Methane

The oxidative methylation of acetonitrile with methane to acrylonitrile occurs more actively and selectivelybialkali promoted CaO catalysts thanany monoalkali promoted system.The most effective catalytic systems are obtained with LiA + CsA, NaA + CsA, or KA + CsA (A = SO42- , OH-, Cl-, CH3COO-, CO32-, or NO3-) supported on CaO, containing total alkali loadings of 10 molpercent with equal molar amounts of both alkalis.At 750 deg C, under atmospheric pressure, at CH4 : O2 : CH3CN : He partial pressure ratios of 5.0 : 1.0 : 1.5 : 6.5, and at a space velocity of 15,000 cm3 g-1 h-1, the highest selectivity to acrylonitrile (70.0 molpercent) and yield (25 percent) are obtained(5 molpercent Na+ + 5 molpercent Cs+)/CaO (prepared from the sulfate precursors).Any bialkali-promoted system containing Rb was less effective, whereas the Li-containing systems, though active initially, gradually lost the activity due to its volatility.The performances of the effective bialkali systems, after an initial increase, remained almost unchanged for a period of 60 h.In contrast, the stability of any monoalkali promoted system with time-on-stream was very low and the maximum initial yield of acrylonitrile was only 11.5 percent under the aforementioned conditions.The synergistic increase in the catalytic performance of the bialkali promoted CaO is reflected in the synergistic increase of the surface basicity (leading to superbasicity) caused by the high enrichment of the surface layer with the alkali ions.The relationship between the catalytic performances and the physicochemical characteristics of the catalysts revealed by XPS, AAS, and basicity measurement is explored.

Selective Formation of Acrylonitrile via Oxidative Methylation of Acetonitrile with Methane over Superbasic Catalysts

Promotion of CaO or MgO with various binary alkali metal compounds such as NaA + CsA, KA + CsA, LiA + CsA or LiA + NaA, where A = SO42-, OH-, Cl-, AcO-, CO32- or NO3-, leads to highly basic (superbasic) catalysts, which exhibit a noticeable synergistic effect compared with the effect produced by any monoalkali promoted system in the selective formation of acrylonitrile via oxidative methylation of acetonitrile with methane.

Synergy in N-Ethylformamide Dehydration by Mixtures of MoO3 and α-Sb2O4

Mixtures of separately prepared MoO3 and α-Sb2O4 show a remarkable synergy in the dehydration of N-ethylformamide to propionitrile when a small amount of oxygen is fed together with the main reagent.The surface acidity of the samples was investigated by TPD of ammonia.ESR and XPS were used for investigating the behavior of the mixtures in reducing and oxidizing conditions.The acidity is attributed mainly to Bronsted sites situated on MoO3.Oxygen is neccessary to maintain these sites.The interpretation is that oxygen is provided, to the surface of MoO3, in the form of spillover oxygen, by α-Sb2O4.Such a mechanism corresponds to what has been called a remote control.

Chemoselective hydrogenation of α,β-unsaturated nitriles

The chemoselective hydrogenation of cinnamonitrile to 3-phenylallylamine proceeds with up to 80% selectivity at conversions of > 90% with Raney cobalt and up to 60% selectivity with Raney nickel catalysts. Best results were obtained with a doped Raney cobalt catalyst (RaCo/Cr/Ni/Fe 2724) in ammonia saturated methanol at 100°C and 80 bar. Major problems are the formation of hydrocinnamonitrile and of secondary amines, and overreduction to 3-phenylpropylamine. Important parameters are the catalyst type and composition, the solvent type and the presence and concentration of ammonia. The catalytic system tolerates functional groups like OH, OMe, Cl, C=O, but not aromatic nitro groups. Preliminary experiments indicate that other unsaturated nitriles with di- or trisubstituted C=C bonds are also suitable substrates.