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1,1-Diphenylethylene

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1,1-Diphenylethylene
Names
Preferred IUPAC name 1,1′-(Ethene-1,1-diyl)dibenzene
Other names Ethene-1,1-diyldibenzene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.712 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H12/c1-12(13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-11H,1H2Key: ZMYIIHDQURVDRB-UHFFFAOYSA-N
SMILES
  • C=C(C1=CC=CC=C1)C2=CC=CC=C2
Properties
Chemical formula C14H12
Molar mass 180.250 g·mol
Melting point 8 °C
Boiling point 277 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

Properties

1,1-Diphenylethylene mediates the radical polymerization of methyl acrylate or styrene. Mediation by 1,1-Diphenylethylene generates low molecular weight polymer by a termination reaction. Additionally, because 1,1-Diphenylethylene has a lower pKa than styrene, it is an effective mediator in the anionic living polymerization of styrene-block-methyl methacrylate copolymers. Polystyrene homopolymers can be "capped" with 1,1-Diphenylethylene before adding methyl methacrylate, effectively adjusting the pKa of the active chain end so that 1,4-addition to methyl methacrylate is favored over 1,2-addition. Dibenzofulvene is an analogue of a 1,1-Diphenylethylene.

Synthesis

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

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. D. Freyss; P. Rempp; H. Benoît (1964). "Polydispersity of Anionically Prepared Block Copolymers". Journal of Polymer Science Part B: Polymer Letters. 2 (2): 217–222. Bibcode:1964JPoSL...2..217F. doi:10.1002/pol.1964.110020214.
  5. 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". Journal of the American Chemical Society. 123 (37): 9182–9183. doi:10.1021/ja0111131. PMID 11552835.
  6. EP0742190 A1, BASF , 13 Nov 1996, Process for the Preparation of Diarylethanes
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