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The Synthesis of Room-Temperature Ionic Liquids and Their Metathesis Reactions with Dilithium Phthalocyanine

Beauchamp, Andrew Michael

Abstract Details

2012, Master of Science (MS), Wright State University, Chemistry.
A series of alkoxyalkylammonium salts has been synthesized for use in metathesis reactions with dilithium phthalocyanine. The salts, which were ionic liquids at or near room temperature, were synthesized by a nucleophilic substitution of tris[2-(2-methoxyethoxy)ethyl]amine and iodomethane, iodoethane, bromoethane, 1-bromo-propane, 1-bromo-2-(2-methoxyethoxy)ethane, and [2-[2-(2-methoxyethoxy)ethoxy]-ethoxy] p-toluenesulfonate in yields ranging from 67% - 88%. The methyl, ethyl, propyl and tetra[2-(2-methoxyethoxy)ethyl]ammonium salts were obtained for use in metathesis reactions. The salts were liquid at room temperature, with the exception of tetra[2-(2-methoxyethoxy)ethyl]ammonium bromide which was found to melt at 46° and were thermally stable to approximately 200°. The four salts were used in metathesis reactions with dilithium phthalocyanine to produce an alkoxyalkylammonium cation lithium phthalocyanine anion complex in yields from 43% - 73%. The complex products were found to be thermally stable to approximately 300° with melting temperatures ranging from 118° - 160°. The structures of tris[2-(2-methoxyethoxy)ethyl]methylammonium lithium phthalocyanine, tris[2-(2-methoxyethoxy)ethyl]propylammonium lithium phthalocyanine, and tetra[2-(2-methoxyethoxy)ethyl]ammonium lithium phthalocyanine were determined by single crystal x-ray diffraction experiments.
William Feld, PhD (Advisor)
Eric Fossum, PhD (Committee Member)
Vladomir Katovic, PhD (Committee Member)
102 p.

Recommended Citations

Citations

  • Beauchamp, A. M. (2012). The Synthesis of Room-Temperature Ionic Liquids and Their Metathesis Reactions with Dilithium Phthalocyanine [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1334348776

    APA Style (7th edition)

  • Beauchamp, Andrew. The Synthesis of Room-Temperature Ionic Liquids and Their Metathesis Reactions with Dilithium Phthalocyanine. 2012. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1334348776.

    MLA Style (8th edition)

  • Beauchamp, Andrew. "The Synthesis of Room-Temperature Ionic Liquids and Their Metathesis Reactions with Dilithium Phthalocyanine." Master's thesis, Wright State University, 2012. http://rave.ohiolink.edu/etdc/view?acc_num=wright1334348776

    Chicago Manual of Style (17th edition)