Quantitation of the reductive cleavage of aryl ethers of SRC and coals. Semi Annual report, September 1980-March 1981

PDF Version Also Available for Download.

Description

During the first period of this contract our work has focused on the synthesis of appropriate aryl ethers to use in testing ether cleavage reactions. These compounds were prepared by standard literature conditions. Generally, an appropriate aryl halide was treated with sodium phenoxide at 150 to 250/sup 0/C using a copper powder catalyst. After separating from the copper and extracting the unreacted sodium phenoxide with water, the residual crude phenyl ether was purified by crystallization, distillation or column chromatography. Several grams of each ether has been obtained. The study of the reductive cleavage of ethers by electrochemical means has been ... continued below

Physical Description

Pages: 6

Creation Information

Woolsey, N.F. & Bartk, D.E. April 1, 1981.

Context

This report is part of the collection entitled: Office of Scientific & Technical Information Technical Reports and was provided by UNT Libraries Government Documents Department to Digital Library, a digital repository hosted by the UNT Libraries. More information about this report can be viewed below.

Who

People and organizations associated with either the creation of this report or its content.

Publisher

Provided By

UNT Libraries Government Documents Department

Serving as both a federal and a state depository library, the UNT Libraries Government Documents Department maintains millions of items in a variety of formats. The department is a member of the FDLP Content Partnerships Program and an Affiliated Archive of the National Archives.

Contact Us

What

Descriptive information to help identify this report. Follow the links below to find similar items on the Digital Library.

Description

During the first period of this contract our work has focused on the synthesis of appropriate aryl ethers to use in testing ether cleavage reactions. These compounds were prepared by standard literature conditions. Generally, an appropriate aryl halide was treated with sodium phenoxide at 150 to 250/sup 0/C using a copper powder catalyst. After separating from the copper and extracting the unreacted sodium phenoxide with water, the residual crude phenyl ether was purified by crystallization, distillation or column chromatography. Several grams of each ether has been obtained. The study of the reductive cleavage of ethers by electrochemical means has been initiated. Cyclic voltammetry was used to determine the reduction potentials and radical anion stabilities for a series of aryl ethers in N,N'-dimethylformamide (DMF). Table 1 summarizes the ethers, which have been currently investigated by cyclic voltammetry. All of these ethers are reduced to a radical anion in a one-electron step at a platinum electrode in DMF using tetrabutylammonium perchlorate (TBAP) as the supporting electrolyte. The stability of the resultant anion radical of the ether is apparently determined by the ability of the anion to delocalize charge away from the carbon-oxygen bond of the ether. The diphenyl ether radical anion is unstable on the time scale of the electrochemical experiment. For example, the radical anion appears to be virtually absent during the reverse scan at a scan rate of 1.0 V/s. This would imply a half-life of less than 10/sup -1/ seconds for the radical anion of diphenyl ether. In contrast, the radical anion of dibenzofuran is quite stable on the electrochemical experimental time scale; there appears to be very little decomposition of the radical anion at reverse scan rates of 0.01 V/s. This is indicative of a half-life of greater than 10/sup 2/ seconds for the dibenzofuran radical anion at 25/sup 0/C.

Physical Description

Pages: 6

Notes

NTIS, PC A02/MF A01.

Language

Item Type

Identifier

Unique identifying numbers for this report in the Digital Library or other systems.

  • Report No.: DOE/PC/30227-T1
  • Grant Number: FG22-80PC30227
  • DOI: 10.2172/6527732 | External Link
  • Office of Scientific & Technical Information Report Number: 6527732
  • Archival Resource Key: ark:/67531/metadc1205306

Collections

This report is part of the following collection of related materials.

Office of Scientific & Technical Information Technical Reports

Reports, articles and other documents harvested from the Office of Scientific and Technical Information.

Office of Scientific and Technical Information (OSTI) is the Department of Energy (DOE) office that collects, preserves, and disseminates DOE-sponsored research and development (R&D) results that are the outcomes of R&D projects or other funded activities at DOE labs and facilities nationwide and grantees at universities and other institutions.

What responsibilities do I have when using this report?

When

Dates and time periods associated with this report.

Creation Date

  • April 1, 1981

Added to The UNT Digital Library

  • July 5, 2018, 11:11 p.m.

Description Last Updated

  • Oct. 23, 2018, 5:46 p.m.

Usage Statistics

When was this report last used?

Congratulations! It looks like you are the first person to view this item online.

Interact With This Report

Here are some suggestions for what to do next.

Start Reading

PDF Version Also Available for Download.

International Image Interoperability Framework

IIF Logo

We support the IIIF Presentation API

Woolsey, N.F. & Bartk, D.E. Quantitation of the reductive cleavage of aryl ethers of SRC and coals. Semi Annual report, September 1980-March 1981, report, April 1, 1981; United States. (digital.library.unt.edu/ark:/67531/metadc1205306/: accessed December 14, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.