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Alkylbenzene

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(Redirected fromAlkylbenzenes)
Family of organic compounds
Toluene (or methylbenzene) is a common chemical found in chemistry laboratories.

Analkylbenzene is a chemical compound that contains a monocyclic aromatic ring attaching to one or more saturated hydrocarbon chains.[1] Alkylbenzenes are derivatives ofbenzene, in which one or more hydrogen atoms are replaced byalkyl groups. The simplest member,toluene (or methylbenzene), has the hydrogen atom of the benzene ring replaced by amethyl group. The chemical formula of alkylbenzenes is CnH2n-6.[2]

Safety hazards of toluene. Oftentimes, toluene is used as an organic solvent.

Alkylbenzenes are a very important class ofhydrocarbons, especially in the synthetic production industry. It is the raw material in the production of syntheticsulfonate detergents, which are found in a variety of household products such as soap, shampoo, toothpaste, laundry detergent, etc.Linear alkylbenzenes (LAB) and branched alkylbenzenes (BAB) are families of alkylbenzene used to preparesynthetic sulfonates. However, LABs are more industrially favoured since the discovery of its extensive biodegradable yield over BAB-based sulfonates in the 1960s.[3]

Examples

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Parent compound:

Benzene

Alkylbenzenes
BenzeneToluene
Xylenes
o-xylenem-xylenep-xylene
Trimethylbenzenes
hemimellitenepseudocumenemesitylene
Tetramethylbenzenes
prehniteneisodurenedurene
Miscellaneous
ethylbenzenecumenep-cymene
Xylene isomers are also used as solvents in laboratories. Note that in the photo,o-xylene, not being stored in a brown glass bottle, appears to have auto-oxidized.

Reactions

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Spectroscopy

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Alkylbenzene isomers can be differentiated by observing the position of alkylsubstituents on the benzene ring usingchemical ionization-proton exchange mass spectrometry. ConventionalGC-MS yields limited results because the isomers have identicalmolecular weight and substituents.[6]

Production

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Some alkylbenzenes such as toluene, trimethylbenzenes, and tetramethylbenzenes occur naturally in coaltar oil and as byproducts of the crude oilrefinery process. Others can be prepared by Friedel-Crafts alkylation.[3]

Alkylbenzenes used to be synthesized fromtetrapropylene, however, the reaction is now rarely used because of the low biodegradable alkylbenzene sulfonates it yields.[3]

Safety hazards

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Alkylbenzenes are flammable. Most of them are eye and skin irritants and pose an acute health hazard when ingested. Alkylbenzenes are toxic to aquatic life with long-lasting effects.

Application

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Synthetic sulfonates

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Alkylbenzenes are the primary raw material in making synthetic alkylbenzene sulfonates. Synthetic sulfonates are the most widely useddetergents, as industrial oil,emulsifiers,demulsifiers,rust inhibitors,dispersants,surfactants for enhanced oil recovery, ore-floatation agents, and wetting agents, among others. LABs such as alkylbenzene, dialkylbenzene, and alkyltoluene are most commonly used to prepare sulfonate detergents.[4]

Solvent use

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Some less substituted alkylbenzenes such as toluene and xylene are commonly used as solvents industrially.

Literature

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  • Allinger, Cava, de Jongh, Johnson, Lebel, Stevens:Organische Chemie, 1. Auflage, Walter de Gruyter, Berlin 1980,ISBN 3-11-004594-X, pp. 367–368, 560–562.
  • Streitwieser / Heathcock:Organische Chemie, 1. Auflage, Verlag Chemie, Weinheim 1980,ISBN 3-527-25810-8, pp. 1051, 1073–1080.
  • Beyer / Walter:Lehrbuch der Organischen Chemie, 19. Auflage, S. Hirzel Verlag, Stuttgart 1981,ISBN 3-7776-0356-2, pp. 442–444.
  • Morrison / Boyd:Lehrbuch der Organischen Chemie, 3. Auflage, Verlag Chemie, Weinheim 1986,ISBN 3-527-26067-6, pp. 707–728.

References

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  1. ^Francis, Alfred W. (1948-02-01)."Properties of Alkylbenzenes".Chemical Reviews.42 (1):107–162.doi:10.1021/cr60131a003.ISSN 0009-2665.PMID 18904921.
  2. ^Sazhin, S. S. (2022).Droplets and sprays : simple models of complex processes. Cham, Switzerland: Springer.ISBN 978-3-030-99746-5.OCLC 1333919856.
  3. ^abcGriesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2013-09-16),"Hydrocarbons", in Wiley-VCH Verlag GmbH & Co. KGaA (ed.),Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. 1–61,doi:10.1002/14356007.a13_227.pub2,ISBN 978-3-527-30673-2,S2CID 242394133, retrieved2023-04-12
  4. ^abcLubricant additives : chemistry and applications. Leslie R. Rudnick. [Place of publication not identified]. 2017.ISBN 978-1-351-64696-3.OCLC 1003859957.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)
  5. ^De, Surya K. (2021-01-26).Applied Organic Chemistry: Reaction Mechanisms and Experimental Procedures in Medicinal Chemistry (1 ed.). Wiley.doi:10.1002/9783527828166.ch5.ISBN 978-3-527-34785-8.S2CID 242435919.
  6. ^Hawthorne, Steven B.; Miller, David J. (1985-03-01)."Identifying alkylbenzene isomers with chemical ionization-proton exchange mass spectrometry".Analytical Chemistry.57 (3):694–698.doi:10.1021/ac00280a027.ISSN 0003-2700.
Saturated
aliphatic
hydrocarbons
Alkanes
CnH2n + 2
Linear alkanes
Branched alkanes
Cycloalkanes
Alkylcycloalkanes
Bicycloalkanes
Polycycloalkanes
Other
Unsaturated
aliphatic
hydrocarbons
Alkenes
CnH2n
Linear alkenes
Branched alkenes
Alkynes
CnH2n − 2
Linear alkynes
Branched alkynes
Cycloalkenes
Alkylcycloalkenes
Bicycloalkenes
Cycloalkynes
Dienes
Other
Aromatic
hydrocarbons
PAHs
Acenes
Other
Alkylbenzenes
C2-Benzenes
Xylenes
Other
C3-Benzenes
Trimethylbenzenes
Other
C4-Benzenes
Cymenes
Tetramethylbenzenes
Other
Other
Vinylbenzenes
Other
Other
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References

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