1,1-Diphenylethylene

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1,1-Diphenylethylene
1,1-Diphenylethene.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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).

1,1-Diphenylethylene is an organic compound with chemical formula (C6H5)2C=CH2. It is a white solid.

Contents

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. [3] 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. [4] Dibenzofulvene is an analogue of a 1,1-Diphenylethylene. [5]

Synthesis

1,1-Diphenylethylene is prepared commercially by alkylating benzene with styrene to give 1,1-diphenylethane. This conversion requires a zeolite catalyst. In a subsequent step, this ethane derivative undergoes dehydrogenation: [6]

C6H5CH=CH2 + C6H6 → (C6H5)2CHCH3
(C6H5)2CHCH3 → (C6H5)2C=CH2 + H2

A laboratory route to 1,1-diphenylethylene entails dehydration of 1,1-diphenylethanol. [7]

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. Bibcode:2001JAChS.123.9182N. doi:10.1021/ja0111131. PMID   11552835.
  6. ↑ EP0742190 A1, BASF , 13 Nov 1996, Process for the Preparation of Diarylethanes
  7. ↑ Allen, C. F. H.; Converse, S. (1926). "1,1-Diphenylethylene". Organic Syntheses. 6: 32. doi:10.15227/orgsyn.006.0032.
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