2-Nitropropane Chemical Properties

Melting point:

-93 °C

Boiling point:

120 °C(lit.)

Density 

0.992 g/mL at 25 °C(lit.)

vapor density 

~3 (vs air)

vapor pressure 

~13 mm Hg ( 20 °C)

refractive index 

n20/D 1.394(lit.)

Flash point:

99 °F

storage temp. 

Flammables area

solubility 

H2O: slightly soluble

pka

pK1:7.675 (25°C)

form 

Liquid

Water Solubility 

1.7 g/100 mL (20 ºC)

Merck 

14,6628

BRN 

1740684

Henry's Law Constant

8.92 at 20.00 °C, 15.3 at 30.00 °C, 24.4 at 40.00 °C, 36.9 at 50.00 °C (inert gas stripping, Bene? and Dohnal, 1999)

Exposure limits

Potential occupational carcinogen. NIOSH REL: IDLH 100 ppm; OSHA PEL: TWA 25 ppm (90 mg/m³); ACGIH TLV: TWA 10 ppm (adopted).

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases, copper.

CAS DataBase Reference

79-46-9(CAS DataBase Reference)

IARC

2B (Vol. 29, Sup 7, 71) 1999

NIST Chemistry Reference

Propane, 2-nitro-(79-46-9)

EPA Substance Registry System

2-Nitropropane (79-46-9)

Safety Information

Hazard Codes 

T

Risk Statements 

45-10-20/22-68-52/53

Safety Statements 

53-45-61-36/37

RIDADR 

UN 2608 3/PG 3

WGK Germany 

3

RTECS 

TZ5250000

Autoignition Temperature

802 °F

HazardClass 

3.2

PackingGroup 

III

HS Code 

29042000

Hazardous Substances Data

79-46-9(Hazardous Substances Data)

Toxicity

Acute oral LD50 for rats 720 mg/kg (quoted, RTECS, 1985).

MSDS

• Language:English Provider:2-Nitropropane
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2-Nitropropane Usage And Synthesis

Description

2-Nitropropane (2-NP) is a clear colourless liquid with a pleasant odour. 2-NP is soluble in many organic solvents including chloroform. Its vapours may form an explosive mixture with air. 2-NP is primarily used as a solvent for organic compounds, coatings, inks, dyes, adhesives, and vinyl resins. Application of 2-NP improves drying time, insures more complete solvent release, provides better flow characteristics, and insures greater pigment dispersion (1,2,3,5). 2-NP has a minor use as an additive in explosives, propellants, and fuels (in racing cars). It also has limited use as a paint and varnish remover. 2-NP serves as an intermediate in the synthesis of some pharmaceuticals, dyes, insecticides, and textile chemicals. It is used for coatings as with vinyl, epoxy paints, nitrocellulose, and chlorinated rubber, in printing inks, adhesives, printing as flexographic inks, maintenance with traffic markings on roads and highways, shipbuilding and maintenance, in furniture, and plastic industries. 2-NP is also used as a solvent in food processing industries for fractionation of a partially saturated vegetable oil. Because of its large-scale use pattern, human exposure to 2-NP has become a health concern.

Chemical Properties

2-Nitropropane(2-NP) is an aliphatic nitro compound. It is a colorless, oily, and flammable liquid with a mild fruity odor. Soluble in water 1.7 mL/100 mL (20C); solubility of water in 2-nitropropane 0.6 cc/100 cc (20C); miscible with organic solvents.
As other nitroalkane, 2-NP exists in tautomeric equilibrium with its nitronic acid isomers (protonated and anionic aci forms).The aci form is amphoterically reactive, the protonated form being electrophilic and the anionic form being nucleophilic.

Chemical Properties

2-Nitropropane exists in equilibrium with 2-propane nitronic acid (HSDB 1988). A 0.01 M aqueous solution has a pH of 6.2. 2-Nitropropane reacts with inorganic bases and amines to form salts which are flammable when dry. 2-Nitropropane is sensitive to detonation when mixed with oxidizers and a mixture of the chemical with ammonium nitrate is a commercial explosive.

Physical properties

Colorless, oily liquid with a mild, fruity odor. 2-Nitropropane was detected in two studies at concentrations of 3.1 and 5.2 ppm_v (Crawford et al., 1984).

Uses

Industrial solvent; chemical intermediate; component in inks and paints

Uses

2-NP is used as an industrial solvent and additive solvent in vinyl, epoxy resin coatings, nitrocellulose, varnishes, paints, chlorinated rubber, printing inks, adhesives, printing (rotogravure and flexographic inks), traffic markings, marine coatings in shipbuilding, food packaging, plastic products, rocket propellant, and as an industrial intermediary in explosives and an additive in gasoline.

Uses

Several nitroalkanes, including nitromethane, nitroethane, 1-nitropropane (1-NP), and 2-nitropropane (2-NP) have been commercially available since 1940. By virtue of their unusual spectrum of industrially desirable properties, their production has rapidly increased for many applications. 2-NP is used widely as a specialty solvent for coatings, printing inks, paints, varnishes, and adhesives. It has also been used as an intermediate in the synthesis of dyes, pesticides, textile chemicals, and pharmaceutics, and an additive in explosives, propellants, and fuels.
Solvent (especially for vinyl and epoxy coatings), chemical synthesis, rocket propellant, gasoline additive.

Definition

A solvent.

Production Methods

Like 1-nitropropane, 2-nitropropane is produced by vapor-phase nitration of propane with nitric acid at elevated temperature and pressure (Baker and Bollmeier 1978). U.S. production in 1977 was put at 30 million pounds (Finklea 1977). Amounts in use have been greatly reduced in recent times because of concern about its carcinogenic potential.

General Description

Colorless liquid with a mild fruity odor. May float on or sink in water.

Air & Water Reactions

Highly flammable.

Reactivity Profile

2-Nitropropane is sensitive to heat. Can react with amines/heavy metal oxides, strong acids, strong alkalis, and chlorosulfonic acid. . The heat of adsorption of 2-Nitropropane on carbon, such as that found in cartridge respirators, is extremely high. Metal oxide catalysts, such as copper oxide or manganese oxide, can initiate ignition, therefore carbon respirators should not be used in environments that have a high vapor concentration of 2-Nitropropane.

Hazard

Flammable, dangerous fire risk, moderate explosion hazard when shocked or heated. Liver damage and liver cancer. Possible carcinogen.

Health Hazard

2-Nitropropane is a lung irritant (HSDB 1988). The acute effects of exposure to 2-nitropropane at 20-45 p.p.m. on workmen were anorexia, nausea, vomiting, diarrhea and severe occipital headache. Complete recovery occurred overnight (Skinner 1947). Hine et al (1978) reported 4 fatalities after exposure of workmen to products containing 11-28% 2-nitropropane. In all 4 cases, the men had been working in confined spaces with poor ventilation for several hours. Presenting symptoms were nausea, vomiting, diarrhea, weakness, dyspnea, chest pain and abdominal pain. Over the next 2 days the patients' condition deteriorated with death occurring within 6-10 d after exposure. The characteristic post-mortem findings were extensive hepatic necrosis and gastrointestinal bleeding. Hine et al (1978) were careful to point out that the only evidence for the involvement of 2-nitropropane was that it was the sole common component of the different products to which the workmen had been exposed.
Two epidemiological studies suggest that no adverse health effects arise as a result of chronic exposure of humans to 2-nitropropane. However, cautious interpretation of the results of both studies is required. Data were gathered from relatively small numbers of subjects who had, in most cases, been exposed to 2-nitropropane for less than 15-20 years. One study included 1481 employees from a 2-nitropropane production plant (NIOSH 1979), while Crawford et al (1985) studied 46 employees of a 2-nitropropane recycling plant, only 18 of whom were considered to have had potential contact with 2-nitropropane.

Fire Hazard

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.

Industrial uses

Solvent systems containing 2-nitropropane are used in various coatings, including vinyl, epoxy paints, nitrocellulose and chlorinated rubber, printing inks and adhesives. When mixed with oxidizers, it is used in explosives (HSDB 1988).

Safety Profile

Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Poison by intraperitoneal route. Moderately toxic by ingestion and inhalation. Human systemic effects by inhalation: anorexia, hypermothty, diarrhea, nausea or vomiting. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. Can cause liver and kidney injury, methemoglobinemia, and cyanosis. Very dangerous fire hazard when exposed to heat, open flame, or oxidizers. May explode on heating. Violent reactions with chlorosulfonic acid, oleum. May react with amines + heavy metal oxides (e.g., mercury oxide or silver oxide) to form explosive salts. May ignite on contact with mixtures of carbon + hopcalite, whch are used in some respirators. Hopcalite is a catalyst consisting of coprecipitated copper(Ⅱ) oxide and manganese0 oxide. To fight fire, use alcohol foam, CO2, dry chemical, water spray. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

2-Nitropropane is used as a solvent for polymers, organic compounds; cellulose, esters; gums,vinyl resins; waxes, epoxy resins, fats, dyes, and chlorinated rubber; as a stabilizer. Its combustion properties have made it useful as a rocket propellant and as a gasoline and diesel fuel additive. 2-Nitropropane also has limited use as a paint and varnish remover. It serves as an intermediate in organic synthesis of some pharmaceuticals; dyes, insecticides, and textile chemicals.

Carcinogenicity

2-Nitropropane is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Environmental Fate

Photolytic. Anticipated products from the reaction of 2-nitropropane with ozone or OH radicals in the atmosphere are formaldehyde and acetaldehyde (Cupitt, 1980).

Metabolism

After exposure of male Sprague-Dawley rats to 2-nitropropane (200 p.p.m. by inhalation, or 50 mg/kg intraperitoneally) the major pathway of elimination was by exhalation. Carbon dioxide, acetone and isopropanol were the major metabolites. Exhalation was also the major route of elimination after a dose of 10 mg/kg to chimpanzees (Muller et al 1983). Nonlinear elimination of 2-nitropropane was suggested by studies in which male Sprague-Dawley rats were exposed by inhalation to doses of 20 or 154 p.p.m. radiolabeled 2-nitropropane for 6 h (Nolan et al 1982). Average blood 2-nitropropane concentrations immediately following the 20 and 154 p.p.m. exposures were 0.6 and 7.1 μg/ml, respectively. Furthermore, raising the dose from 20 to 154 p.p.m. caused a greater fraction of the radioactivity to be excreted as unchanged 2-nitropropane. The dose-dependent changes in the elimination of 2-nitropropane may account, at least in part, for the increase in toxicity observed in rats exposed to large concentrations of 2-nitropropane (Lewis et al 1979).
Analysis of incubations of 2-nitropropane with liver microsomes of phenobarbital or 3-methylcholanthrene pretreated male Sprague-Dawley rats indicated that oxidative denitrification of 2-nitropropane produced acetone and nitrite (Ullrich et al 1978). This effect seems not to be dependent on pretreatment with a cytochrome P-450 inducer in other species or strains, since the hepatic microsomes from 5 strains of untreated mice all showed significant, but variable, NADPH-dependent ability to release nitrite from 2-nitropropane (Marker and Kulkarni 1985). Ullrich and coworkers (1978) considered that the reduction of the nitro group of 2-nitropropane to form 2-aminopropane was unlikely, at least in vitro, since the rate of oxidative denitrification of 2-nitropropane was unaltered in microsomal incubations under reduced oxygen tension. Whether any significant nitro group reduction of 2-nitropropane occurs in vivo to produce potentially reactive metabolites is unknown. Speck et al (1982), however, have shown that 2-aminopropane is not mutagenic in Salmonella tester strains.

Shipping

UN2608 Nitropropanes, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Purify it as for nitromethane. [Beilstein 1 IV 230.]

Toxicity evaluation

DNA damage can cause 2-NP metabolites such as N-isopropyl hydroxylamine (IPHA) and hydroxylamine-O-sulfonic (HAS) acid by a reactive oxygen generating process that can be inhibited by free hydroxyl radical scavengers, catalase, and deferoxamine mesylate, an iron chelating agent. IPHA causes DNA damage at thymine and HAS most frequently induces DNA damage at 5'-TG-3', 5'-GG-3', and 5' -GGG-3' sequences. Formation of 8-oxodesoxyguanine by IPHA or HAS increased in the presence of metal ions.DNA damage caused by 2-NP metabolites plays an important role in mutagenicity and carcinogenicity of 2-NP. The liver damage induced by 2-NP is related to oxidative damage and reduction in catalase (CAT) activity.

Incompatibilities

1-Nitropropane, a nitroparaffin compound, forms explosive mixture with air. Contact with heavy metal oxides may cause decomposition. Mixtures with hydrocarbons are extremely flammable. Attacks some plastics, rubber and coatings. May explode on heating. Violent reaction with strong bases; strong acids and metal oxides. Shock-sensitive compounds are formed with acids, amines, inorganic bases and heavy metal oxides. Incompatible with strong oxidizers, combustible materials. 2-Nitropropane reacts with activated carbon causing decomposition. This reaction may occur in activated carbon respirator filters.

Waste Disposal

Incineration: large quantities of material may require nitrogen oxide removal by catalytic or scrubbing processes. Dilute with pure kerosene and burn with care as it is potentially explosive. Consult with environmental regulatory agencies for guidance 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.

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