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Toward The Synthesis of Functionalized Poly (Ether Ether Ketone): Monitoring the meta-Fluorine Displacement in 3,5,4’-trifluorobenzophenone

Covarrubias, Giovanni
http://rave.ohiolink.edu/etdc/view?acc_num=wright1495051005255892

Abstract Details

2017, Master of Science (MS), Wright State University, Chemistry.
The synthesis of functionalized, linear poly (ether ether ketone), tailored to be semi-crystalline and soluble in a variety of organic-solvents was explored. Nucleophilic aromatic substitution was a chemical reaction method used to condense 3,5,4’-trifluorobenzophenone (TFK) with four different phenols at its para-positioned carbon-fluorine site: 4-methoxyphenol, 3-aminophenol, 4-bromophenol, and m-cresol. Further poly-condensation of functionalized TFK occurred at the meta-positioned carbon-fluorine sites with 4,4’-Bis[4-hydroxyphenoxy] benzophenone (Big A2) and 4,4’-difluorobenzophenone at molar equivalents of 1 to 0.5, respectively. The reaction afforded products that became insoluble in solvents needed for nuclear magnetic resonance spectroscopic (e.g. DMSO-d6) analysis. The lack of desirable compounds compelled the necessity of examining the displacement of the fluorine groups in TFK located meta to the electron withdrawing group, the carbonyl moiety. Gas Chromatography/Mass Spectrometry (GC/MS) and Nuclear Magnetic Resonance Spectroscopy (NMR), 1H and 13C, were used to analyze samples at varying reaction times and revealed that while it is possible to displace at least one of the meta-fluorine atoms in mono-substituted TFK with Big A2 and Bisphenol A, more time and a potentially higher temperature may be needed to complete the reaction. The synthesis of 75:25 PEEK-co-meta-PEEK, 5, from a previous project was successfully replicated and verified using Differential Scanning Calorimetry (DSC).
Eric Fossum, Ph.D. (Advisor)
William Feld, Ph.D. (Committee Member)
Daniel Ketcha, Ph.D (Committee Member)
64 p.
Chemistry
PAE; PEEK; Trifluorobenzophenone; Difluorobenzophenone; Functionalization

Recommended Citations

Citations

  • Covarrubias, G. (2017). Toward The Synthesis of Functionalized Poly (Ether Ether Ketone): Monitoring the meta-Fluorine Displacement in 3,5,4’-trifluorobenzophenone [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1495051005255892

    APA Style (7th edition)

  • Covarrubias, Giovanni. Toward The Synthesis of Functionalized Poly (Ether Ether Ketone): Monitoring the meta-Fluorine Displacement in 3,5,4’-trifluorobenzophenone. 2017. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1495051005255892.

    MLA Style (8th edition)

  • Covarrubias, Giovanni. "Toward The Synthesis of Functionalized Poly (Ether Ether Ketone): Monitoring the meta-Fluorine Displacement in 3,5,4’-trifluorobenzophenone." Master's thesis, Wright State University, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=wright1495051005255892

    Chicago Manual of Style (17th edition)

wright1495051005255892
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© 2017, all rights reserved.
This open access ETD is published by Wright State University and OhioLINK.