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Nitrobenzene

Description References
Nitrobenzene
Nitrobenzene structure
CAS No.
98-95-3
Chemical Name:
Nitrobenzene
Synonyms
NCI-C60082;NITROBENZOL;MYRBANE OIL;MIRBANE OIL;Nitrobenzen;oilofmyrbane;NITROBENZENE;Nitrobenzeen;nitro-benzen;Mitrobenzole
CBNumber:
CB7854756
Molecular Formula:
C6H5NO2
Formula Weight:
123.11
MOL File:
98-95-3.mol

Nitrobenzene Properties

Melting point:
5-6 °C(lit.)
Boiling point:
210-211 °C(lit.)
Density 
1.205
vapor density 
4.2 (vs air)
vapor pressure 
0.15 mm Hg ( 20 °C)
refractive index 
n20/D 1.551(lit.)
Flash point:
190 °F
storage temp. 
2-8°C
solubility 
1.90g/l
pka
3.98(at 0℃)
form 
Liquid
color 
Clear yellow
PH
8.1 (1g/l, H2O, 20℃)
Relative polarity
4.5
explosive limit
1.8-40%(V)
Water Solubility 
slightly soluble
Merck 
14,6588
BRN 
507540
Exposure limits
TLV-TWA 1 ppm (~5 mg/m3) (ACGIH, MSHA, and OSHA); IDLH 200 ppm (NIOSH).
Stability:
Stable. Incompatible with strong oxidizing agents, strong reducing agents, strong bases. Flammable. Note wide explosion limits.
CAS DataBase Reference
98-95-3(CAS DataBase Reference)
NIST Chemistry Reference
Benzene, nitro-(98-95-3)
EPA Substance Registry System
Benzene, nitro-(98-95-3)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
  • NFPA
Hazard Codes  T,N,F,Xn
Risk Statements  23/24/25-40-48/23/24-51/53-62-39/23/24/25-11-36/37/38-60-52/53-48/23/24/25-36-20/21/22
Safety Statements  28-36/37-45-61-28A-16-7-27-53-26
RIDADR  UN 1662 6.1/PG 2
WGK Germany  2
RTECS  DA6475000
Autoignition Temperature 899 °F
TSCA  Yes
HazardClass  6.1
PackingGroup  II
Hazardous Substances Data 98-95-3(Hazardous Substances Data)
Toxicity LD50 orally in rats: 600 mg/kg (PB91-108398)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H227 Combustible liquid Flammable liquids Category 4 Warning P210, P280, P370+P378, P403+P235,P501
H300 Fatal if swallowed Acute toxicity,oral Category 1, 2 Danger P264, P270, P301+P310, P321, P330,P405, P501
H310 Fatal in contact with skin Acute toxicity,dermal Category 1, 2 Danger P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
H330 Fatal if inhaled Acute toxicity,inhalation Category 1, 2 Danger P260, P271, P284, P304+P340, P310,P320, P403+P233, P405, P501
H351 Suspected of causing cancer Carcinogenicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H361 Suspected of damaging fertility or the unborn child Reproductive toxicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
H372 Causes damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 1 Danger P260, P264, P270, P314, P501
H401 Toxic to aquatic life Hazardous to the aquatic environment, acute hazard Category 2 P273, P501
H411 Toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 2
H412 Harmful to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 3 P273, P501
Precautionary statements:
P201 Obtain special instructions before use.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P320 Specific treatment is urgent (see … on this label).
P330 Rinse mouth.
P304+P340 IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P308+P313 IF exposed or concerned: Get medical advice/attention.
P370+P378 In case of fire: Use … for extinction.
P405 Store locked up.
P403+P235 Store in a well-ventilated place. Keep cool.

NFPA 704

Diamond Hazard Value Description
2
3 1
Health   3 Short exposure could cause serious temporary or moderate residual injury (e.g. liquid hydrogen, sulfuric acid, calcium hypochlorite, hexafluorosilicic acid)
Flammability   2 Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur and multiple finely divided suspended solids that do not require heating before ignition can occur. Flash point between 37.8 and 93.3 °C (100 and 200 °F). (e.g. diesel fuel, sulfur)
Instability   1 Normally stable, but can become unstable at elevated temperatures and pressures (e.g. propene)
Special  

(NFPA, 2010)

Nitrobenzene price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 06084 Nitrobenzene PESTANAL , analytical standard 98-95-3 1ml-f $16.7 2018-11-13 Buy
Sigma-Aldrich 06084 Nitrobenzene PESTANAL , analytical standard 98-95-3 5ml-f $52.5 2018-11-13 Buy
Alfa Aesar A10585 Nitrobenzene, 99% 98-95-3 2500g $79.7 2018-11-13 Buy
Alfa Aesar A10585 Nitrobenzene, 99% 98-95-3 500g $26.6 2018-11-13 Buy
Sigma-Aldrich 40054 Nitrobenzene solution certified reference material, 5000 μg/mL in methanol 98-95-3 40054 $35.3 2018-11-23 Buy

Nitrobenzene Chemical Properties,Uses,Production

Description

Nitrobenzene (chemical formula: C6H4NO2) is a yellowish, oily, aromatic nitro-compound. The most important application of nitrobenzene (consuming 95%) is for the manufacturing of aniline, which is an important industrial precursor. Besides aniline, it can also be used to generate related derivatives such as azobenzene, nitrosobenzene and phenylhydroxylamine. Moreover, it can be used for the production of lubricating oils, dyes, drugs, pesticides, and synthetic rubber. Another special application of it is masking unpleasant odors emitting from shoe, floor polisher, and leather as well as paint solvents. In addition, it can sometime used as a solvent, especially for electrophilic reagents in the laboratory. The nitrobenzene is mainly manufactured through the nitration of benzene with the mixture of concentrated sulfuric acid, water and nitric acid. However, the reaction process is quite dangerous due to the exothermicity of the reaction.

References

https://pubchem.ncbi.nlm.nih.gov/compound/nitrobenzene#section=Top
https://en.wikipedia.org/wiki/Nitrobenzene

Chemical Properties

Aromatic nitro compounds mixed with nitrobenzene are explosives of high sensitivity and detonation velocities and are spark detonatable).

Chemical Properties

yellow liquid

Chemical Properties

Nitrobenzene is a pale yellow to dark brown oily liquid whose odor resembles bitter almonds (or black paste shoe polish).

Uses

The primary use of nitrobenzene is in the captive production of aniline, with about 97.5% of nitrobenzene production consumed in this process. The major use of aniline is in the manufacture of polyurethanes. Nitrobenzene is also used as a solvent in petroleum refining, in the manufacture of cellulose ethers and acetate, and in Friedel-Crafts reactions to hold the catalyst in solution. It is also used in the synthesis of other organic compounds including acetaminophen, which is an over-the-counter analgesic commonly known as Tylenol?.
Nitrobenzene is used as a flavoring agent, a perfume for soaps and as a solvent for shoe dyes.

Uses

Nitrobenzene is an organic compound used a standard for detection and analyses as well as its removal from the environment. The compound’s cytotoxic effects have been studied in a hepatocarcinoma cell line.

Uses

For the manufacture of aniline; in soaps, shoe polishes; for refining lubricating oils; manufacture of pyroxylin Compounds.

Production Methods

Nitrobenzene is produced by the direct nitration of benzene with a mixture of sulfuric and nitric acids. U.S. capacity for nitrobenzene production is approximately 1.5 billion pounds . The most important use for nitrobenzene is in the production of aniline. Nearly 98% of the nitrobenzene produced in the U.S. is converted to aniline.

Definition

ChEBI: A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.

Preparation

Nitrobenzene is produced commercially by the exothermic nitration of benzene with fuming nitric acid in the presence of a sulfuric acid catalyst at 50 to 65℃. The crude nitrobenzene is passed through washer-separators to remove residual acid and is then distilled to remove benzene and water.

Definition

A yellow organic oil obtained by refluxing benzene with a mixture of concentrated nitric and sulfuric acids. The reaction is a typical electrophilic substitution on the benzene ring by the nitryl cation (NO2+).

Definition

nitrobenzene: A yellow oily liquid,C6H5NO2; r.d. 1.2; m.p. 6°C; b.p.211°C. It is made by the nitration ofbenzene using a mixture of nitricand sulphuric acids.

General Description

A pale yellow to dark brown liquid. Flash point 190°F. Very slightly soluble in water. Toxic by inhalation and by skin absorption. Combustion give toxic oxides of nitrogen. Density 10.0 lb /gal.

Air & Water Reactions

Very slightly soluble in water.

Reactivity Profile

Aluminum chloride added to Nitrobenzene containing about 5% phenol caused a violent explosion [Chem. Eng. News 31:4915. 1953]. Heating a mixture of Nitrobenzene, flake sodium hydroxide and a little water led to an explosion, discussed in [Bretherick's 5th ed. 1995]. Mixed with oxidants, i.e. dinitrogen tetraoxide, fluorodinitromethane, nitric acid, peroxodisulfuric acid, sodium chlorate, tetranitromethane, uranium perchlorate, etc., forms highly sensitive explosive, [Bretherick 5th ed, 1995]. Heated mixtures of Nitrobenzene and tin(IV) chloride produce exothermic decomposition with gas production [Bretherick, 5th Ed., 1995].

Hazard

Toxic by ingestion, inhalation, and skin absorption. Methemoglobinemia. Possible carcinogen.

Health Hazard

Can cause death due to respiratory failure. Classified as extremely toxic. The mean lethal oral dose is probably between 1 and 5 grams. Systemic effects may be delayed for a few hours. Nitrobenzene is rapidly absorbed through the skin. It is a powerful methemoglobin former. Ethyl alcohol aggravates intoxication caused by Nitrobenzene exposure.

Health Hazard

The routes of entry of nitrobenzene intothe body are the inhalation of its vaporsor absorption of the liquid or the vaporthrough the skin and, to a much lesserextent, ingestion. The target organs are theblood, liver, kidneys, and cardiovascular system. Piotrowski (1967) estimated that in anexposure period of 6 hours to a concentration of 5 mg/m3, 18 mg of nitrobenzene wasabsorbed through the lungs and 7 mg throughthe skin in humans. Furthermore, about 80%of inhaled vapor is retained in the respiratorytract. The dermal absorption rate at this concentration level is reported as 1 mg/h, whilethe subcutaneous absorption of the liquidis between 0.2 and 0.3 mg/cm3/h (ACGIH1986).
The symptoms of acute toxicity are headache, dizziness, nausea, vomiting, and dyspnea. Subacute and chronic exposure cancause anemia. Nitrobenzene effects the conversion of hemoglobin to methemoglobin. Itis metabolized to aminophenols and nitrophenols to about 30%, which are excreted.

Health Hazard

The most consistently reported toxic effect in humans exposed to nitrobenzene is methemoglobinemia. Numerous case reports have appeared in the literature, and there is no clear-cut correlation between suspected dose and severity of the methemoglobinemia. Infants are apparently particularly sensitive to nitrobenzeneinduced methemoglobinemia. A number of case histories relate neurologic symptoms to nitrobenzene exposure. The signs and symptoms include headache, confusion, vertigo, nausea, loss of cognition, hyperalgesia, paresthesia, and polyneuritis . Hepatotoxic effects have also been reported to occur in humans exposed to nitrobenzene. A female patient who had been exposed to high concentrations of nitrobenzene for 17 months developed an enlarged and tender liver, icterus, and an increased retention of bromosulfophthalein.

Fire Hazard

Moderate explosion hazard when exposed to heat or flame. Reacts violently with nitric acid, aluminum trichloride plus phenol, aniline plus glycerine, silver perchlorate and nitrogen tetroxide. Avoid aluminum trichloride; aniline; gycerol; sulfuric acid; oxidants; phosphorus pentachloride; potassium; potassium hydroxide. Avoid sunlight, physical damage to container, freezing, and intense heat.

Industrial uses

Nitrobenzene is mainly utilized for aniline production. The aniline is used primarily for the manufacture of 4,4'-methylenebis (phenyl isocyanate) and polymers thereof (50%). The second largest use of aniline is in the manufacture of chemicals for rubber production (30%). Dyes and dye intermediates, hydroquinone and drugs account for about 8% of the aniline produced, while 10% of the aniline is converted to agricultural products such as pesticides and defoliants (Northcott 1978). It also is used as a solvent for cellulose ethers and an ingredient in polishes for metals and shoes (HSDB 1988).

Safety Profile

Confirmed carcinogen. Human poison by an unspecified route. Poison experimentally by subcutaneous and intravenous routes. Moderately toxic by ingestion, skin contact, and intraperitoneal routes. Human systemic effects by ingestion: general anesthetic, respiratory stimulation, and vascular changes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. An eye and skin irritant. Can cause cyanosis due to formation of methemoglobin. It is absorbed rapidly through the skin. The vapors are hazardous. to heat and flame. Moderate explosion hazard when exposed to heat or flame. Explosive reaction with solid or concentrated alkali + heat (e.g., sodium hydroxide or potassium hydroxide), aluminum chloride + phenol (at 12O°C), aniline + glycerol + sulfuric acid, nitric + sulfuric acid + heat. Forms explosive mixtures with aluminum chloride, oxidants (e.g., fluorodinitromethane, uranium perchlorate, tetranitromethane, sodium chlorate, nitric acid, nitric acid + water, peroxodsulfuric acid, dinitrogen tetraoxide), phosphorus pentachloride, potassium, sulfuric acid. Reacts violently with aniline + glycerin, N20, AgCLO4. To fight fne, use water, foam, CO2, dry chemical. Incompatible with potassium hydroxide. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Potential Exposure

Nitrobenzene is used in the manufacture of explosives and aniline dyes and as solvent and intermediate. It is also used in floor polishes; leather dressings and polished; and paint solvents, and to mask other unpleasant odors. Substitution reactions with nitrobenzene are used to form m-derivatives. Pregnant women may be especially at risk with respect to nitrobenzene as with many other chemical compounds, due to transplacental passage of the agent. Individuals with glucose-6-phosphate dehydrogenase deficiency may also be special risk groups. Additionally, because alcohol ingestion or chronic alcoholism can lower the lethal or toxic dose of nitrobenzene, individuals consuming alcoholic beverages may be at risk.

First aid

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

Metabolism

Nitrobenzene vapor is readily absorbed through the skin and lungs. At an airborne nitrobenzene concentration of 10 mg/m3 humans may absorb 18 to 25 mg in 6 h through the lungs and from 8 to 19 mg through the skin in the same length of time .
Urine is the major route of excretion of nitrobenzene metabolites in rabbits , rats and mice . The most abundant metabolite in earlier studies in rabbits and rats was p-aminophenol. This compound, or its glucuronide or sulfate conjugates, accounted for 19% to 31% of the dose. In a later study in rats in which the acid hydrolysis step employed by earlier workers to cleave conjugates was replaced by enzyme hydrolysis, no p-aminophenol was found in the urine of male Fischer-344 or CD rats .
About 9% of a nitrobenzene dose was excreted by B6C3F1 mice as the sulfate conjugate. The major metabolites found in Fischer-344 rat urine were p-hydroxyacetanilide sulfate (19% of the dose), p-nitrophenol sulfate (20% of the dose) and m-nitrophenol sulfate (10% of the dose) .
In addition, an unidentified metabolite accounted for about 10% of the dose .
Male CD rats excreted the same metabolites after an oral dose of nitrobenzene, but in slightly different proportions. They excreted about half as much of the dose as the glucuronide or sulfate conjugates of P-hydroxyacetanilide (9% of the dose) and P-nitrophenol (13% of the dose), approximately the same amount of m-nitrophenol (8% of the dose), and about twice as much as the unidentified metabolite. Interestingly, whereas Fischer-344 rats excreted the phenolic metabolites of nitrobenzene exclusively as sulfates, CD rats excreted the same metabolites in the free form (15-17% of the total metabolite) and as glucuronides (4-20% of the total metabolite).
Approximately 4% of the dose also was excreted as p-hydroxyacetanilide by B6C3F1 mice and as p- and m-nitrophenol (7% and 6% of the dose, respectively) sulfates, glucuronides and free metabolites .
Clearly, ring hydroxylation and reduction are important metabolic steps in the biotransformation of nitrobenzene in rabbits, rats, mice and humans . Since no significant isotope effect was found in the metabolism of deuterated nitrobenzene to these products in rats in vivo , the o- and p-nitrophenols may be formed through an arene oxide intermediate. A significant isotope effect was noted in the formation of m-nitrophenol from deuterated nitrobenzene in the same rats, leading to the conclusion that m-nitrophenol is formed by a direct oxygen insertion mechanism or by some other mechanism which does not involve an arene oxide intermediate. The reduction of nitrobenzene in vivo is largely, if not exclusively, due to the action of anaerobic intestinal microflora. Treatment with antibiotics totally eliminated the ability of cecal contents of Fischer-344 rats to reduce nitrobenzene in vitro, and rats treated with antibiotics eliminated p-hydroxyacetanilide as 0.9% of an oral dose of nitro-benzene. Normal rats excreted 16.2% of an oral dose of nitrobenzene as that metabolite .
The reduction of most nitro compounds by hepatic microsomes is not detectable under aerobic conditions, but is readily observable under anaerobic conditions. Mason and Holtzman proposed that the first intermediate in the microsomal reduction of nitroaromatic compounds is the nitro anion radical, the product of a one electron transfer to nitrobenzene or other nitroaromatic compound. Oxygen would rapidly oxidize the radical to yield the parent nitro compound and Superoxide anion. Both the nitro anion radical and Superoxide anion are potentially toxic compounds.
Both P-nitrophenol and P-aminophenol have been detected in human urine after exposure to nitrobenzene. p-Aminophenol has been found only after large accidental exposures and acid hydrolysis of urine. Since acid conditions convert p-acetamidophenol to P-aminophenol, the identity of the metabolite actually excreted is in doubt. P-Nitrophenol has been found in the urine of volunteers exposed to low inhalation doses of nitrobenzene, and Kuzelova and Popler have suggested that urinary P-nitrophenol be used to monitor exposure to nitrobenzene.

Shipping

UN1662 Nitrobenzene, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Common impurities include nitrotoluene, dinitrothiophene, dinitrobenzene and aniline. Most impurities can be removed by steam distillation in the presence of dilute H2SO4, followed by drying with CaCl2, and shaking with, then distilling at low pressure from BaO, P2O5, AlCl3 or activated alumina. It can also be purified by fractional crystallisation from absolute EtOH (by refrigeration). Another purification process includes extraction with aqueous 2M NaOH, then water, dilute HCl, and water, followed by drying (CaCl2, MgSO4 or CaSO4) and fractional distillation under reduced pressure. The pure material is stored in a brown bottle, in contact with silica gel or CaH2. It is very hygroscopic. [Beilstein 5 H 233, 5 I 124, 5 II 171, 5 III 591, 5 IV 708.]

Incompatibilities

Concentrated nitric acid, nitrogen tetroxide; caustics; phosphorus pentachloride; chemically-active metals, such as tin or zinc. Violent reaction with strong oxidizers and reducing agents. Attacks many plastics. Forms thermally unstable compounds with many organic and inorganic compounds.

Waste Disposal

Incineration (982℃, 2.0 seconds minimum) with scrubbing for nitrogen oxides abatement . 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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