Benzyl toluenes

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The benzyltoluenes form a group of several isomeric chemical compounds . It is a group of aromatic hydrocarbons that are formally methyl-substituted diphenylmethanes and at the same time chemically closely related to dibenzyltoluene .

Representative

Benzyl toluenes
Surname o -Benzyltoluene m -Benzyltoluene p -Benzyltoluene
Structural formula o-benzyltoluene m-benzyltoluene p-benzyltoluene
other names 2-methyldiphenylmethane 3-methyldiphenylmethane 4-methyldiphenylmethane
CAS number 713-36-0 620-47-3 620-83-7
27776-01-8 (mixture of isomers)
PubChem 69738 136427 69290
Molecular formula C 14 H 14
Molar mass 182.26 g mol −1
Physical state liquid
Brief description colorless liquid with a faint odor
Melting point 6.6 ° C (0.01 Pa) −30 ° C
boiling point 281 ° C 282 ° C
283–287 ° C (mixture of isomers)
density 0.995 g cm −3 (mixture of isomers)
Vapor pressure 0.66 Pa (20 ° C, mixture of isomers)
solubility practically insoluble in water (0.003 g / l at 20 ° C), soluble in ethanol and benzene
Refractive index 1.5763 1.5712
GHS
labeling 		from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 08 - Dangerous to health
danger
H and P phrases 304-315-413
no EUH phrases
273-280-301 + 310-302 + 352-331-332 + 313

Extraction and presentation

Benzyltoluene can be obtained by condensing benzyl chloride with toluene .

o -benzyltoluene can be obtained by reacting o- xylyl chloride with benzene and zinc , p -benzyltoluene by reacting p - bromotoluene with benzene or toluene, m -benzyltoluene by reacting m -xylyl chloride with benzene and aluminum trichloride .

properties

Benzyltoluenes are flammable, hardly inflammable, colorless liquids with a faint odor that are practically insoluble in water.

use

The benzyltoluenes are mostly used (as a mixture of isomers) as technical fluids in capacitors (dielectric fluids ) or heat transfer fluids . Benzyltoluene mixtures, together with dibenzyltoluene , are also being discussed as possible liquid organic hydrogen carriers for storing hydrogen .

literature

  • Beilstein's Handbook of Organ. Chemie ( Benzyltoluenes , System No. 479), Vol. 5: H 607 , EII 498 .

Individual evidence

  1. ↑ a b c d e f g entry to benzyltoluene in the GESTIS database of IFA , accessed on November 4, 2016(JavaScript required) .
  2. ↑ a b c d e f g William M. Haynes: CRC Handbook of Chemistry and Physics, 93rd Edition . CRC Press, 2016, ISBN 978-1-4398-8050-0 , pp. 360 ( limited preview in Google Book Search).
  3. ↑ Entry on benzyltoluene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 4, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ patent-de.com: Process for the synthesis of benzyltoluene and dibenzyltoluene with a low chlorine content. - Document DE69021034T2 , accessed November 4, 2016
  5. ↑ Dr. Hans Meyer: Synthesis of the carbon compounds First part: Open chains and isocycles . Springer-Verlag, 2013, ISBN 978-3-7091-3245-6 , pp. 449 ( limited preview in Google Book search).
  6. ↑ arkema: Benzyltoluene
  7. Jump up ↑ Nicole Brückner, Katharina Obesser, Andreas Bösmann, Daniel Teichmann, Wolfgang Arlt, Jennifer Dungs, Peter Wasserscheid: Evaluation of Industrially Applied Heat-Transfer Fluids as Liquid Organic Hydrogen Carrier Systems . In: ChemSusChem . tape 7 , no. 1 , 2014, p. 229-235 , doi : 10.1002 / cssc.201300426 ( PDF ).