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1,1-Diphenylethylene
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1,1-Diphenylethene.png 1,1-(Ethene-1,1-diyl)dibenzene Ethene-1,1-diyldibenzene 530-48-3 correct CAS correct FDA BX0L5B6LLL 10740 10287 C=C(C1=CC=CC=C1)C2=CC=CC=C2 1S/C14H12/c1-12(13-8-4-2-5-9-13)14-10-6-3-7-11-14/h2-11H,1H2 ZMYIIHDQURVDRB-UHFFFAOYSA-N
14 12 8 °CSmith, 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. 277 °CCRC 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.
1,1-Diphenylethylene is an organic compound with chemical formula (C6H5)2C\dCH2. It is a colorless to light orange to yellow clear liquid.1,1-Diphenylethylene 530-48-3 | TCI Chemicals (India) PVT. LTD. https://www.tcichemicals.com/IN/en/p/D0886
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.Minjian Zhao Zhifeng Fu Yan Shi Wantai Yang Polymerization Mechanism in the Presence of 1,1-Diphenylethylene Part 2: Synthesis and Characterization of PMA and PSt Macromolecular Chemistry and Physics 2015 216 22 2202–2210 10.1002/macp.201500249 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.D. Freyss P. Rempp H. Benoît Polydispersity of Anionically Prepared Block Copolymers Journal of Polymer Science Part B: Polymer Letters 1964 2 2 217–222 10.1002/pol.1964.110020214 1964JPoSL...2..217F Dibenzofulvene is an analogue of a 1,1-Diphenylethylene.Tamaki Nakano Kazuyuki Takewaki Tohru Yade Yoshio Okamoto Dibenzofulvene, a 1,1-Diphenylethylene Analogue, Gives a π-Stacked Polymer by Anionic, Free-Radical, and Cationic Catalysts Journal of the American Chemical Society 2001 123 37 9182–9183 10.1021/ja0111131 11552835 2001JAChS.123.9182N
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:EP0742190 A1, BASF, 13 Nov 1996, Process for the Preparation of Diarylethanes
C6H5CH\dCH2 + C6H6 → (C6H5)2CHCH3
(C6H5)2CHCH3 → (C6H5)2C\dCH2 + H2
A laboratory route to 1,1-diphenylethylene entails dehydration of 1,1-diphenylethanol.10.15227/orgsyn.006.0032 free 1,1-Diphenylethylene Organic Syntheses 1926 6 32 C. F. H. Allen S. Converse
See also
Dibenzofulvene
Stilbene
References
Category:Phenyl compounds
Category:Vinylidene compounds