1,1-Diphenylethylene

1,1-Diphenylethylene
Names
	Preferred IUPAC name 1,1′-(Ethene-1,1-diyl)dibenzene
	Other names Ethene-1,1-diyldibenzene
Identifiers
CAS Number	530-48-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	10287;
ECHA InfoCard	100.007.712
PubChem CID	10740;
UNII	BX0L5B6LLL ;
CompTox Dashboard (EPA)	DTXSID5060190 ;
	InChI 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;
	SMILES C=C(C1=CC=CC=C1)C2=CC=CC=C2;
Properties
Chemical formula	C14H12
Molar mass	180.250 g·mol−1
Melting point	8 °C
Boiling point	277 °C
	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. 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 technical prepared by alkylating benzene by styrene in presence of a zeolite beta and subsequent dehydrogenation.^[6]

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

References

^ 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.
^ 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.
^ 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.
^ D. Freyss; P. Rempp; H. Benoît (1964). "Polydispersity of Anionically Prepared Block Copolymers". J. Polymer Sci. 2 (2): 217–222. doi:10.1002/pol.1964.110020214.
^ 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.
^ EP0742190 A1, BASF , 13 Nov 1996, Process for the Preparation of Diarylethanes

[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". J. Polymer Sci. 2 (2): 217–222. 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". J. Am. Chem. Soc. 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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Properties

Synthesis

See also

References