Indan

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Structural formula
Structure of indan
General
Surname Indan
other names
  • Hydrinds
  • Benzocyclopentane
  • 2,3-dihydro-1 H -indene
Molecular formula C 9 H 10
Brief description

colorless liquid

External identifiers / databases
CAS number 496-11-7
EC number 207-814-7
ECHA InfoCard 100.007.105
PubChem 10326
Wikidata Q420109
properties
Molar mass 118.18 g · mol -1
Physical state

liquid

density

0.96 g cm −3

Melting point

−51 ° C

boiling point

178 ° C

solubility

in water 0.109 g / l (25 ° C), easily soluble in ethanol and diethyl ether

Refractive index

1.5378 (20 ° C)

safety instructions
GHS labeling of hazardous substances
02 - Highly / extremely flammable 08 - Dangerous to health

danger

H and P phrases H: 226-304
P: 301 + 310-331
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Indan (stress on the final syllable: Ind a n ) is a chemical compound from the group of bicyclic aromatic hydrocarbons .

Extraction and presentation

Indan occurs widely in coal tar , primeval tar and as a structural element in indene resin . It can be produced from indene by catalytic hydrogenation over platinum catalysts using hydrogen or by reduction with metallic sodium in ethanol .

properties

Indan is a colorless liquid with an aromatic odor that boils at 178 ° C under normal pressure . The heat of vaporization is 49.2 kJ mol −1 . The solid can exist in two polymorphic crystal forms. The transition temperature from Form II to Form I is −199 ° C. Form I melts at −51 ° C. The heat of fusion is 8.6 kJ mol −1 , the heat of transformation from form II to form I is 0.8 kJ mol −1 .

Compilation of the most important thermodynamic properties
property Type Value [unit] Remarks
Standard enthalpy of formation Δ f H 0 liquid −11.7 kJ mol −1
Standard entropy S 0 liquid 234.35 J mol −1 K −1 as a liquid
Enthalpy of combustion Δ c H 0 liquid −4982.5 kJ mol −1
Heat capacity c p 190.25 J mol −1 K −1 (25 ° C)
130.7 J mol −1 K −1 (25 ° C) 		as a liquid
as a gas
Triple point T triple 221.77K
Critical temperature T c 684.9 K
Critical pressure p c 39.5 bar

The temperature dependence of the enthalpy of vaporization can be calculated according to the equation Δ V H 0 = A exp (−β T r ) (1 − T r ) β (Δ V H 0 in kJ / mol, T r = (T / T c ) reduced temperature) with A = 65.1 kJ / mol, β = 0.2866 and T c = 684.9 K in the temperature range between 302 K and 339 K.

use

Indane can be converted into indene by dehydration . Derivatives (indanes) are used in many ways as antibiotics, cardiac therapeutics, insecticides and fragrances (musk). A well-known derivative of indane is ninhydrin .

Related links

Web links

Individual evidence

  1. ↑ a b c d e f g Entry on Indan in the GESTIS substance database of the IFA , accessed on November 29, 2012(JavaScript required) .
  2. ^ A b Brockhaus ABC Chemie, VEB FA Brockhaus Verlag Leipzig 1965, p. 561.
  3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-302.
  4. ^ S. Hauptmann, J. Graefe, H. Remane: Textbook of Organic Chemistry , Deutscher Verlag für Grundstoffindustrie Leipzig 1980, p. 263.
  5. ↑ a b Roux, MV; Temprado, M .; Chickos, JS; Nagano, Y .: Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons in J. Phys. Chem. Ref. Data 37 (2008), pp. 1855-1996 ( doi : 10.1063 / 1.2955570 ).
  6. ↑ a b c d e Stull, DR; Sink, GC; McDonald, RA; Hatton, WE; Hildenbrand, DL: Thermodynamic properties of indane and indene in Pure Appl. Chem. 2, pp. 315-322 (1961) ( doi : 10.1351 / pac196102010315 ).
  7. ↑ Good, WD: The enthalpies of combustion and formation of indan and seven alkylindans in J. Chem. Thermodyn. 3 (1971), pp. 711-717 ( doi : 10.1016 / S0021-9614 (71) 80095-2 ).
  8. ↑ Dorofeeva OV: Thermodynamic Properties of Gaseous Polycyclic Aromatic Hydrocarbons Containing Five-Membered Rings in Institute for High Temperatures, USSR Academy of Sciences, Preprint No. 1-263 (in Russian), Moscow, 1989.
  9. ↑ Stull, DR; Sink, GC; McDonald, RA; Hatton, WE; Hildenbrand, DL: Thermodynamic properties of indane and indene in Symposium uber Thermodynamik, 1959, pp. 1-9.
  10. ↑ a b Tsonopoulos, C .; Ambrose, D .: Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic hydrocarbons in J. Chem. Eng. Data 40 (1995), pp. 547-558 ( doi : 10.1021 / je00019a002 ).
  11. ↑ Majer, V .; Svoboda, V .: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation , Blackwell Scientific Publications, Oxford, 1985, 300.
  12. ↑ Entry on Indan. In: Römpp Online . Georg Thieme Verlag, accessed on June 7, 2014.