1,1-Diphenylethylene
Names
Preferred IUPAC name
1,1′-(Ethene-1,1-diyl)dibenzene
Other names
Ethene-1,1-diyldibenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.712
UNII
  • InChI=1S/C14H12/c1-12(13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-11H,1H2
    Key: ZMYIIHDQURVDRB-UHFFFAOYSA-N
  • C=C(C1=CC=CC=C1)C2=CC=CC=C2
Properties
C14H12
Molar mass 180.250 g·mol−1
Melting point 8 °C[1]
Boiling point 277 °C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,1-Diphenylethylene is an aromatic hydrocarbon with chemical formula C14H12.

Properties

1,1-Diphenylethylene mediates the radical polymerization of methyl acrylate or styrene. Meditation by 1,1-Diphenylethylene generates low molecular weight polymer by a termination reaction.[3] Dibenzofulvene is an analogue of a 1,1-Diphenylethylene.[4]

Synthesis

1,1-Diphenylethylene is technical prepared by alkylating benzene by styrene in presence of a zeolite beta and subsequent dehydrogenation.[5]

styrene + benzene → 1,1-diphenylethane → 1,1-diphenylethylene + H2

See also

References

  1. ↑ Smith, R.H.; Andrews, D.H.: Thermal Energy Studies I. Phenyl Derivatives of Methane, Ethane and Some Related Compounds in J. Am. Chem. Soc. 53 (1931) 3644.
  2. ↑ CRC Handbook of Data on Organic Compounds, 2nd Edition, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1.
  3. ↑ Minjian Zhao; Zhifeng Fu; Yan Shi; Wantai Yang (2015). "Polymerization Mechanism in the Presence of 1,1-Diphenylethylene Part 2: Synthesis and Characterization of PMA and PSt". Macromolecular Chemistry and Physics. 216 (22): 2202–2210. doi:10.1002/macp.201500249.
  4. ↑ Tamaki Nakano; Kazuyuki Takewaki; Tohru Yade; Yoshio Okamoto (2001). "Dibenzofulvene, a 1,1-Diphenylethylene Analogue, Gives a π-Stacked Polymer by Anionic, Free-Radical, and Cationic Catalysts". J. Am. Chem. Soc. 123 (37): 9182–9183. doi:10.1021/ja0111131. PMID 11552835.
  5. ↑ EP0742190 A1, BASF , 13 Nov 1996, Process for the Preparation of Diarylethanes
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