Accession Number:

AD0677021

Title:

SYNTHESIS AND CONVERSIONS OF CERTAIN p- AND p,p'- DERIVATIVES OF DIPHENYLOXIDE (SINTEZ I PREVRASHCHENIYA NEKOTORYKH p- I p,p' PROIZVORNYKH DIFENILOKSIDA),

Descriptive Note:

Corporate Author:

FOREIGN TECHNOLOGY DIV WRIGHT-PATTERSON AFB OHIO

Personal Author(s):

Report Date:

1967-10-31

Pagination or Media Count:

14.0

Abstract:

As part of an investigation of highly stable oils and their components, a number of derivatives of diphenyl ether were prepared and their properties tested. All of the derivatives made were either monofunctional para-derivatives or difunctional di-para-derivatives. The initial reaction in either case was chloromethylation. The chloromethylated products were converted to aldehydes by the Sommelet reaction. The corresponding alcohols and acids were obtained from the aldehydes by the Canizzaro reaction. The aldehydes were converted into p-phenoxycinnamic acid and the corresponding dibasic acid by both the Claisen condensation, and the Perkin reaction. The starting chloromethylated derivatives were also converted to alkoxymethyl, acetoxymethyl, hydroxymethyl, and carboxy derivatives of diphenyl ether. The diethyl, diisobytyl, and di-2-ethylhexyl ethers of p,p-dihydroxy methyldiphenyl ether fit the boiling point, solidification point, and viscosity requirements for synthetic lubricating oils. Thermooxidative stability studies showed that at 150C, 1 mole of p,p-diisobutoxy methyldiphenyl ether absorbed 0.167 mole of oxygen, as compared to 0.8 mole of oxygen absorbed by 1 mole of diectyl sebacate under the same conditions. Author

Subject Categories:

  • Organic Chemistry
  • Lubricants and Hydraulic Fluids

Distribution Statement:

APPROVED FOR PUBLIC RELEASE