Ethyl benzene

Ethylbenzene
Identifiers
Abbreviations EB
CAS number 100-41-4 YesY
PubChem 7500
ChemSpider 7219 YesY
UNII L5I45M5G0O YesY
DrugBank DB01722
KEGG C07111 YesY
ChEBI CHEBI:16101 YesY
RTECS number DA0700000
Beilstein Reference 1901871
Jmol-3D images Image 1
Properties
Molecular formula C8H10
Molar mass 106.17 g mol−1
Appearance colorless liquid
Density 0.8665 g/mL
Melting point

-95 °C, 178 K, -139 °F

Boiling point

136 °C, 409 K, 277 °F

Solubility in water 0.015 g/100 mL (20 °C)
log P 3.27
Vapor pressure 9.998mmHg
Refractive index (nD) 1.495
Viscosity 0.669 cP at 20 °C
Thermochemistry
Specific heat capacity, C 1.726 J/(gK)
Hazards
R-phrases R11 R20
S-phrases (S2) S16 S24/25 S29
Main hazards Flammable
NFPA 704
3
2
0
Flash point 22.22 °C
Autoignition
temperature
430°C
Explosive limits 1%-7.8%
LD50 5460 mg/kg
Related compounds
Related aromatic
hydrocarbons
styrene, toluene
Related compounds benzene
polystyrene
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene. Ethylbenzene is also used to make other chemicals, in fuel, and as a solvent in inks, rubber adhesives, varnishes, and paints. Ethylbenzene exposure can be determined by testing for the breakdown products in urine.

Physical and chemical properties

Ethylbenzene[1] is a colorless liquid that smells similar to gasoline with a sweet aroma, evaporates quickly and is highly flammable. It has a characteristic odor with an odor threshold at 2.3 ppm and a melting point of −95 °C (−139 °F) and a boiling point of 136 °C (277 °F).[2] It is classified as a monocyclic aromatic hydrocarbon since it is a compound that contains only carbon and hydrogen atoms.,[1][3]

Occurrence and applications

Ethylbenzene occurs naturally in coal tar and petroleum, although this is not the main source of this compound.[4]

The dominant application of ethylbenzene is role as an intermediate in the production of polystyrene. Catalytic dehydrogenation of ethylbenzene gives hydrogen and styrene:

→ C6H5CH=CH2 +

As of May 2012, greater than 99% of all the ethylbenzene produced is used for this purpose.

Niche uses

Ethylbenzene is added to gasoline as an anti-knock agent, meaning it reduces engine knocking and increase the octane rating. Ethylbenzene is often found in other manufactured products, including pesticides, cellulose acetate, synthetic rubber, paints, and inks.[4] Used in the recovery of natural gas, ethylbenzene many be injected into the ground.

Production

Ethylbenzene is produced in on a large scale by combining benzene () and ethylene () in an acid-catalyzed chemical reaction:

+

In 2012, more than 99% of ethylbenzene was produced in this way. Thus, manufacturers of ethylbenzene are the major buyers of benzene, claiming more than half of total output.[5]

Small amounts of ethylbenzene is recovered from the mix of xylenes by superfractioning, an extension of the distillation process.[1]

In the 1980s a zeolite-based process using vapor phase alkylation, offered a higher purity and yield. Then a liquid phase process was introduced using zeolite catalysts. This offers low benzene-to-ethylene ratios, reducing the size of the required equipment and lowering byproduct production.[6]

Approximately 24,700,000 tons were produced in 1999.[7]

Health effects

The acute toxicity of ethylbenzene is low, with an LD50 of about 4 grams per kilogram of body weight. The longer term toxicity and carcinogenicity is ambiguous.[7] Eye and throat sensitivity can occur when high level exposure to ethylbenzene in the air occurs. At higher level exposure, ethylbenzene can cause dizziness.[4] Once inside the body, ethylbenzene biodegrades to 1-phenylethanol, acetophenone, phenylglyoxylic acid, mandelic acid, benzoic acid and hippuric acid.[7]

As of September 2007, the United States Environmental Protection Agency (EPA) determined that drinking water with concentration of 30 parts per million (ppm) for one day or 3 ppm for ten days is not expected to have any adverse effect in children. Lifetime exposure of 0.7 ppm ethylbenzene is not expected to have any adverse effect either. The U.S. Occupational Health and Safety Administration (OSHA) limits exposure to workers to an average 100 ppm for an 8-hour work day, a 40-hour workweek.[4]

Ethylbenzene is classified as a possible carcinogen by the International Agency for Research on Cancer (IARC) however, the EPA has not determined ethylbenzene to be a carcinogen

As for all organic compounds, ethylbenzene vapors form an explosive mixture with air.[1] When transporting ethylbenzene, it is classified as a flammable liquid in class 3, Packing Group II.[1]

Environmental effects

Ethylbenzene is found mostly as a vapor in the air since it can easily move from water and soil.[4] A median concentration of 0.62 parts per billion (ppb) was found in urban air in 1999.[2] A study conducted in 2012 found that in country air the median concentration was found to be 0.01 ppb and indoors the median concentration was 1.0 ppb. It can also be released into the air through the burning of coal, gas, and oil. The use of ethylbenzene in industry contributes to ethylbenzene vapor in the air. After about three days in the air with the help of sunlight, other chemicals break down ethylbenzene into chemicals that can be found in smog.[4] Since it does not readily bind to soil it can also easily move into groundwater. In surface water, it breaks down when it reacts with chemicals naturally found in water.[8] Generally, ethylbenzene is not found in drinking water, however it can be found in residential drinking water wells if the wells are near waste sites, underground fuel storage tanks that are leaking, or landfills.[4]

As of 2012, according to the EU Dangerous Substances Directive, ethylbenzene is not classified as hazardous to the environment.[1]

References

External links

  • National Pollutant Inventory - Ethybenzene Fact Sheet
  • NLM Hazardous Substances Databank – Ethylbenzene
  • EPA Chemical database
  • Intox Chemical database
  • Agency for Toxic Substances and Disease Registry
  • CDC - NIOSH Pocket Guide to Chemical Hazards
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.