1,1-Diphenylethylene

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

1,1-Diphenylethylene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.712
UNII
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

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 Editon, 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.
  5. EP0742190 A1, BASF , 13 Nov 1996, Process for the Preparation of Diarylethanes


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