Dibenzyltoluene

Structural formula
General structural formula of several structurally isomeric dibenzyltoluenes
General
Surname	Dibenzyltoluene
other names	Dibenzylmethylbenzene Marlotherm SH
Molecular formula	C 21 H 20
Brief description	colorless to yellowish liquid with a faint odor
External identifiers / databases
CAS number 26898-17-9 29589-57-9 53585-53-8 EC number 248-097-0 ECHA InfoCard 100.043.710 PubChem 3034397 Wikidata Q22668712
properties
Molar mass	272.38 g mol −1
Physical state	liquid
density	1.044 g cm −3 (20 ° C)
Melting point	-34 ° C
boiling point	390 ° C
Vapor pressure	10 Pa at 140 ° C
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 304-413 P: 273-301 + 310-331-405-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dibenzyltoluene is a mixture of several chemical compounds from the group of substituted aromatic hydrocarbons . It is practically always present as a mixture of several structural isomeric , lower and higher oligomers of benzyltoluene . At room temperature it is a colorless to yellowish liquid. The liquid is classified as hazardous to water (water hazard class 2) and harmful to health .

use

Dibenzyltoluene is used as a dielectric fluid in electrical engineering and as a heat transfer oil . It can be used in the temperature range from 5 ° C to 350 ° C.

In addition, its use as a liquid organic hydrogen carrier (LOHC) has increasingly become the focus of research in recent years . The hydrogen is chemically bound to an unsaturated and temperature-stable carrier substance through an exothermic hydrogenation reaction . The hydrogen can then be released again through an endothermic dehydrogenation reaction. The fully hydrogenated form of dibenzyltoluene is called perhydro-dibenzyltoluene or H18-DBT . Another name is Wassol .

Manufacturing

Dibenzyltoluene is produced by reacting toluene with benzyl chloride via Friedel-Crafts alkylation .

Individual evidence

1. ↑ ^{a b c d e f} Entry on dibenzyltoluene, isomers in the GESTIS substance database of the IFA , accessed on February 3, 2018(JavaScript required) .
2. ↑ Dutch. GefStoff database
3. ↑ ^{a b} Karsten Müller, Katharina Stark, Vladimir N. Emel'yanenko, Mikhail A. Varfolomeev, Dzmitry H. Zaitsau, Evgeni Shoifet, Christoph Schick, Sergey P. Verevkin, Wolfgang Arlt: Liquid Organic Hydrogen Carriers: Thermophysical and Thermochemical Studies of Benzyl- and dibenzyl-toluene derivatives . In: Industrial & Engineering Chemistry Research . tape 54 , no. 32 , August 19, 2015, p. 7967-7976 , doi : 10.1021 / acs.iecr.5b01840 .
4. ↑ Definition in patent DE 69021034 , sheet 2.
5. ↑ List of commercially available dielectrics
6. ↑ On p. 52 of an EU regulation from 2003
7. ^ Christian Papp, Peter Wasserscheid, Jörg Libuda, Hans-Peter Steinrück: Hydrogen, chemically stored. In: News from chemistry. 62, 2014, pp. 963-969, doi: 10.1002 / nadc.201490355 .
8. 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 ).
9. ^ Gabriel Sievi, Denise Birthig et al .: Towards an efficient liquid organic hydrogen carrier fuel cell concept. In: Energy & Environmental Science. No. 7, 2010, pp. 2305-2314, doi : 10.1039 / C9EE01324E .
10. ↑ Timm Koch : The supermolecule. 3. Edition. Westend Verlag GmbH, Frankfurt / Main 2019 ISBN 978-3-86489-240-0 , p. 169.
11. ↑ Process for the synthesis of benzyltoluene and dibenzyltoluene with low chlorine content , patent DE 69021034, filed on December 18, 1990.
12. ↑ Chen Shengzong, Chen Xin, Chen Rui, Chen Junyan: Synthesis of Benzyltoluene as Heat Conducting Oil . In: JOURNAL OF HUNAN UNIVERSITY (NATURNAL SCIENCES) . tape 6 , 1996 ( online ).