Ethylbenzene

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Ethylbenzene
Identifiers
AbbreviationsEB
CAS number100-41-4 YesY
PubChem7500
ChemSpider7219 YesY
UNIIL5I45M5G0O YesY
DrugBankDB01722
KEGGC07111 YesY
ChEBICHEBI:16101 YesY
ChEMBLCHEMBL371561 YesY
RTECS numberDA0700000
Beilstein Reference1901871
Jmol-3D imagesImage 1
Properties
Molecular formulaC8H10
Molar mass106.17 g mol−1
Appearancecolorless liquid
Density0.8665 g/mL
Melting point−95 °C; −139 °F; 178 K
Boiling point136 °C; 277 °F; 409 K
Solubility in water0.015 g/100 mL (20 °C)
log P3.27
Vapor pressure9.998mmHg
Refractive index (nD)1.495
Viscosity0.669 cP at 20 °C
Dipole moment0.58 D[1]
Thermochemistry
Specific heat capacity, C1.726 J/(gK)
Hazards
R-phrasesR11 R20
S-phrases(S2) S16 S24/25 S29
Main hazardsFlammable
NFPA 704
NFPA 704.svg
3
2
0
Flash point22.22 °C; 72.00 °F; 295.37 K
Autoignition temperature430 °C; 806 °F; 703 K
Explosive limits1%-7.8%
LD505460 mg/kg
Related compounds
Related aromatic
hydrocarbons
styrene, toluene
Related compoundsbenzene
polystyrene
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references
 
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Ethylbenzene
Identifiers
AbbreviationsEB
CAS number100-41-4 YesY
PubChem7500
ChemSpider7219 YesY
UNIIL5I45M5G0O YesY
DrugBankDB01722
KEGGC07111 YesY
ChEBICHEBI:16101 YesY
ChEMBLCHEMBL371561 YesY
RTECS numberDA0700000
Beilstein Reference1901871
Jmol-3D imagesImage 1
Properties
Molecular formulaC8H10
Molar mass106.17 g mol−1
Appearancecolorless liquid
Density0.8665 g/mL
Melting point−95 °C; −139 °F; 178 K
Boiling point136 °C; 277 °F; 409 K
Solubility in water0.015 g/100 mL (20 °C)
log P3.27
Vapor pressure9.998mmHg
Refractive index (nD)1.495
Viscosity0.669 cP at 20 °C
Dipole moment0.58 D[1]
Thermochemistry
Specific heat capacity, C1.726 J/(gK)
Hazards
R-phrasesR11 R20
S-phrases(S2) S16 S24/25 S29
Main hazardsFlammable
NFPA 704
NFPA 704.svg
3
2
0
Flash point22.22 °C; 72.00 °F; 295.37 K
Autoignition temperature430 °C; 806 °F; 703 K
Explosive limits1%-7.8%
LD505460 mg/kg
Related compounds
Related aromatic
hydrocarbons
styrene, toluene
Related compoundsbenzene
polystyrene
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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[edit]

Ethylbenzene[2] 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).[3] It is classified as a monocyclic aromatic hydrocarbon since it is a compound that contains only carbon and hydrogen atoms.,[2][4]

Occurrence and applications[edit]

Ethylbenzene occurs naturally in coal tar and petroleum, although this is not the main source of this compound.[5]

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

C
6
H
5
CH
2
CH
3
→ C6H5CH=CH2 + H
2

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

Niche uses[edit]

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.[5] Used in the recovery of natural gas, ethylbenzene many be injected into the ground.

Production[edit]

Ethylbenzene is produced in on a large scale by combining benzene (C
6
H
6
) and ethylene (C
2
H
4
) in an acid-catalyzed chemical reaction:

C
6
H
6
+ C
2
H
4
C
6
H
5
CH
2
CH
3

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.[6]

Small amounts of ethylbenzene is recovered from the mix of xylenes by superfractioning, an extension of the distillation process.[2]

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.[7]

Approximately 24,700,000 tons were produced in 1999.[8]

Health effects[edit]

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.[8] Eye and throat sensitivity can occur when high level exposure to ethylbenzene in the air occurs. At higher level exposure, ethylbenzene can cause dizziness.[5] Once inside the body, ethylbenzene biodegrades to 1-phenylethanol, acetophenone, phenylglyoxylic acid, mandelic acid, benzoic acid and hippuric acid.[8]

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 Safety and Health Administration (OSHA) limits exposure to workers to an average 100 ppm for an 8-hour work day, a 40-hour workweek.[5]

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.[2] When transporting ethylbenzene, it is classified as a flammable liquid in class 3, Packing Group II.[2]

Environmental effects[edit]

Ethylbenzene is found mostly as a vapor in the air since it can easily move from water and soil.[5] A median concentration of 0.62 parts per billion (ppb) was found in urban air in 1999.[3] 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.[5] 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.[9] 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.[5]

As of 2012, according to the EU Dangerous Substances Directive, ethylbenzene is not classified as hazardous to the environment.[2]

Biodegredation[edit]

Certain strands of the fungus Cladophialophora can grow on ethylbenzene.[10]

References[edit]

  1. ^ Lange's Handbook of Chemistry (15th ed.). 1999. 
  2. ^ a b c d e f "ETHYLBENZENE : ENVIRONMENTAL, HEALTH & SAFETY GUIDELINES". CEFIC. Retrieved 14 February 2013. 
  3. ^ a b "Technology Transfer Network Air Toxics Web Site: Ethylbenzene". US Environmental Protection Agency. Retrieved 13 February 2013. 
  4. ^ --, William H. Brown ... [et al.]. (2009). Organic Chemistry. (5th ed. . ed.). Belmont, CA: Brooks/Cole Cengage Learning. pp. 56, 208. ISBN 9780495388579. 
  5. ^ a b c d e f g "Ethylbenzene". Agency for Toxic Substances and Disease Registry. Retrieved 12 February 2013. 
  6. ^ Market Study Benzene, published by Ceresana, July 2011 [1]
  7. ^ "Ethylbenzene (EB) Production and Manufacturing Process". PIERS. Retrieved 14 February 2013. 
  8. ^ a b c Vincent A.Welch, Kevin J. Fallon, Heinz-Peter Gelbke “Ethylbenzene” Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a10_035.pub2
  9. ^ "Ethylbenzene". eco-usa.net. Retrieved 12 February 2013. 
  10. ^ Francesc X. PRENAFETA-BOLDU; Andrea KUHN; Dion M. A. M. LUYKX; Heidrun ANKE; Johan W. van GROENESTIJN; Jan A. M. de BONT (April 2001). Isolation and characterisation of fungi growing on volatile aromatic hydrocarbons as their sole carbon and energy source 105 (4). pp. 477–484. 

External links[edit]