The dominant application of ethylbenzene is its role as an intermediate in the production of polystyrene. Catalytic dehydrogenation of ethylbenzene gives hydrogen and styrene:
C 6H 5CH 2CH 3 → C6H5CH=CH2 + H 2
As of May 2012, more than 99% of all the ethylbenzene produced is used for this purpose.
Ethylbenzene is added to gasoline as an anti-knock agent to reduce engine knocking and increase the octane rating. Ethylbenzene is often found in other products, including pesticides, cellulose acetate, synthetic rubber, paints, and inks.[4] Used in the recovery of natural gas, ethylbenzene may be injected into the ground.
In 2012, more than 99% of ethylbenzene was produced in this way.[citation needed]
Small amounts of ethylbenzene are recovered from the mix of xylenes by superfractioning, an extension of the distillation process.[5]
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 zeolitecatalysts. This offers low benzene-to-ethylene ratios, reducing the size of the required equipment and lowering byproduct production.[6]
Industrial accidents
On June 3, 2014 an explosion occurred in the Dutch Moerdijk industrial area. This happened in a chemical reactor operated by Shell which overheated due to an exothermalrunaway reaction between the metal oxide catalyst and ethylbenzene.[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.[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.[4] Once inside the body, ethylbenzene biodegrades to 1-phenylethanol, acetophenone, phenylglyoxylic acid, mandelic acid, benzoic acid and hippuric acid.[8] Ethylbenzene exposure can be determined by testing for the breakdown products in urine.
As of September 2007, the United States Environmental Protection Agency (EPA) determined that drinking water with a 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 workday, 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. The National Toxicology Program conducted an inhalation study in rats and mice. Exposure to ethylbenzene resulted in an increased incidence of kidney and testicular tumors in male rats, and trends of increased kidney tumors in female rats, lung tumors in male mice, and liver tumors in female mice.
As with all organic compounds, ethylbenzene vapors form an explosive mixture with air.[5] When transporting ethylbenzene, it is classified as a flammable liquid in class 3, Packing Group II.[5]
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.[9] 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 the 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.[10] 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.[5]
^ abcdefg"Ethylbenzene ToxFAQs" (PDF). Agency for Toxic Substances and Disease Registry. Retrieved 21 May 2018.
^ abcd. CEFIC. Archived from the original on 19 September 2014. Retrieved 14 February 2013.
^"Ethylbenzene (EB) Production and Manufacturing Process". PIERS. Retrieved 14 February 2013.
^Summary shell moerdijk onderzoeksraad.nl July 2018
^ abVincent 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
^"Technology Transfer Network Air Toxics Web Site: Ethylbenzene". US Environmental Protection Agency. Retrieved 13 February 2013.
^. eco-usa.net. Archived from the original on 25 December 2012. Retrieved 12 February 2013.
^Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. ISSN 1660-4601. PMC3084482. PMID 21556207.
^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". Mycological Research. 105 (4): 477–484. doi:10.1017/s0953756201003719.
^Rabus, R.; Widdel, F. (1995). "Anaerobic degradation of ethylbenzene and other aromatic hydrocarbons by new denitrifying bacteria". Archives of Microbiology. 163 (2): 96–103. doi:10.1007/s002030050177. PMID 7710331.
National Toxicology Program. Toxicology and Carcinogenesis Studies of Ethylbenzene (CAS No. 100-41-4) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). TR No. 466. U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health, Bethesda, MD. 1999.
External links
NLM Hazardous Substances Databank – Ethylbenzene
Intox Chemical database
CDC - NIOSH Pocket Guide to Chemical Hazards
August 21, 2023
ethylbenzene, organic, compound, with, formula, c6h5ch2ch3, highly, flammable, colorless, liquid, with, odor, similar, that, gasoline, this, monocyclic, aromatic, hydrocarbon, important, petrochemical, industry, reaction, intermediate, production, styrene, pre. 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 a reaction 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 NamesIUPAC name EthylbenzeneOther names Ethylbenzol Phenylethane alpha Methyltoluene EBIdentifiersCAS Number 100 41 4 Y3D model JSmol Interactive imageAbbreviations EBBeilstein Reference 1901871ChEBI CHEBI 16101 YChEMBL ChEMBL371561 YChemSpider 7219 YDrugBank DB01722 YECHA InfoCard 100 002 591KEGG C07111 YPubChem CID 7500RTECS number DA0700000UNII L5I45M5G0O YCompTox Dashboard EPA DTXSID3020596InChI InChI 1S C8H10 c1 2 8 6 4 3 5 7 8 h3 7H 2H2 1H3 YKey YNQLUTRBYVCPMQ UHFFFAOYSA N YInChI 1 C8H10 c1 2 8 6 4 3 5 7 8 h3 7H 2H2 1H3Key YNQLUTRBYVCPMQ UHFFFAOYAMSMILES CCc1ccccc1PropertiesChemical formula C 8H 10Molar mass 106 168 g mol 1Appearance colorless liquidOdor aromatic 1 Density 0 8665 g mLMelting point 95 C 139 F 178 K Boiling point 136 C 277 F 409 K Solubility in water 0 015 g 100 mL 20 C log P 3 27Vapor pressure 9 998 mmHgMagnetic susceptibility x 77 20 10 6 cm3 molRefractive index nD 1 495Viscosity 0 669 cP at 20 CDipole moment 0 58 D 2 ThermochemistryHeat capacity C 1 726 J gK HazardsOccupational safety and health OHS OSH Main hazards FlammableGHS labelling PictogramsSignal word DangerHazard statements H225 H304 H320 H332 H335 H336 H351 H360 H373 H400 H411Precautionary statements P201 P202 P210 P233 P240 P241 P242 P243 P260 P261 P264 P271 P273 P280 P281 P301 P310 P303 P361 P353 P304 P312 P304 P340 P305 P351 P338 P308 P313 P312 P314 P331 P337 P313 P370 P378 P391 P403 P233 P403 P235 P405 P501NFPA 704 fire diamond 230Flash point 22 22 C 72 00 F 295 37 K Autoignitiontemperature 430 C 806 F 703 K Explosive limits 1 7 8 Lethal dose or concentration LD LC LD50 median dose 5460 mg kgLCLo lowest published 4000 ppm rat 4 hr 3 NIOSH US health exposure limits PEL Permissible TWA 100 ppm 435 mg m3 1 REL Recommended TWA 100 ppm 435 mg m3 ST 125 ppm 545 mg m3 1 IDLH Immediate danger 800 ppm 1 Related compoundsRelated aromatichydrocarbons styrene tolueneRelated compounds benzenepolystyreneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Occurrence and applications 1 1 Niche uses 2 Production 2 1 Industrial accidents 3 Health effects 3 1 Environmental effects 3 2 Biodegradation 4 References 5 External linksOccurrence and applications EditEthylbenzene occurs naturally in coal tar and petroleum 4 The dominant application of ethylbenzene is its role as an intermediate in the production of polystyrene Catalytic dehydrogenation of ethylbenzene gives hydrogen and styrene C6 H5 CH2 CH3 C6H5CH CH2 H2As of May 2012 more than 99 of all the ethylbenzene produced is used for this purpose Ethylbenzene hydroperoxide a reagent and radical initiator is produced by autoxidation of ethylbenzene C6H5CH2CH3 O2 C6H5CH O2H CH3Niche uses Edit Ethylbenzene is added to gasoline as an anti knock agent to reduce engine knocking and increase the octane rating Ethylbenzene is often found in other products including pesticides cellulose acetate synthetic rubber paints and inks 4 Used in the recovery of natural gas ethylbenzene may be injected into the ground Production EditEthylbenzene is produced on a large scale by combining benzene and ethene in an acid catalyzed chemical reaction C6 H6 C2 H4 C6 H5 CH2 CH3In 2012 more than 99 of ethylbenzene was produced in this way citation needed Small amounts of ethylbenzene are recovered from the mix of xylenes by superfractioning an extension of the distillation process 5 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 Industrial accidents Edit On June 3 2014 an explosion occurred in the Dutch Moerdijk industrial area This happened in a chemical reactor operated by Shell which overheated due to an exothermal runaway reaction between the metal oxide catalyst and ethylbenzene 7 Health effects EditThe 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 4 Once inside the body ethylbenzene biodegrades to 1 phenylethanol acetophenone phenylglyoxylic acid mandelic acid benzoic acid and hippuric acid 8 Ethylbenzene exposure can be determined by testing for the breakdown products in urine As of September 2007 the United States Environmental Protection Agency EPA determined that drinking water with a 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 workday 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 The National Toxicology Program conducted an inhalation study in rats and mice Exposure to ethylbenzene resulted in an increased incidence of kidney and testicular tumors in male rats and trends of increased kidney tumors in female rats lung tumors in male mice and liver tumors in female mice As with all organic compounds ethylbenzene vapors form an explosive mixture with air 5 When transporting ethylbenzene it is classified as a flammable liquid in class 3 Packing Group II 5 Environmental effects Edit 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 9 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 the 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 10 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 5 Ethylbenzene is a constituent of tobacco smoke 11 Biodegradation Edit Certain strains of the fungus Cladophialophora can grow on ethylbenzene 12 The bacterium Aromatoleum aromaticum EbN1 was discovered due to its ability to grow on ethylbenzene 13 References Edit a b c d NIOSH Pocket Guide to Chemical Hazards 0264 National Institute for Occupational Safety and Health NIOSH Lange s Handbook of Chemistry 15th ed 1999 Ethyl benzene Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH a b c d e f g Ethylbenzene ToxFAQs PDF Agency for Toxic Substances and Disease Registry Retrieved 21 May 2018 a b c d ETHYLBENZENE ENVIRONMENTAL HEALTH amp SAFETY GUIDELINES CEFIC Archived from the original on 19 September 2014 Retrieved 14 February 2013 Ethylbenzene EB Production and Manufacturing Process PIERS Retrieved 14 February 2013 Summary shell moerdijk onderzoeksraad nl July 2018 a b 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 Technology Transfer Network Air Toxics Web Site Ethylbenzene US Environmental Protection Agency Retrieved 13 February 2013 Ethylbenzene eco usa net Archived from the original on 25 December 2012 Retrieved 12 February 2013 Talhout Reinskje Schulz Thomas Florek Ewa Van Benthem Jan Wester Piet Opperhuizen Antoon 2011 Hazardous Compounds in Tobacco Smoke International Journal of Environmental Research and Public Health 8 12 613 628 doi 10 3390 ijerph8020613 ISSN 1660 4601 PMC 3084482 PMID 21556207 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 Mycological Research 105 4 477 484 doi 10 1017 s0953756201003719 Rabus R Widdel F 1995 Anaerobic degradation of ethylbenzene and other aromatic hydrocarbons by new denitrifying bacteria Archives of Microbiology 163 2 96 103 doi 10 1007 s002030050177 PMID 7710331 National Toxicology Program Toxicology and Carcinogenesis Studies of Ethylbenzene CAS No 100 41 4 in F344 N Rats and B6C3F1 Mice Inhalation Studies TR No 466 U S Department of Health and Human Services Public Health Service National Institutes of Health Bethesda MD 1999 External links EditNational 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 Retrieved from https en wikipedia org w index php title Ethylbenzene amp oldid 1166454803, wikipedia, wiki, book, books, library,
