Direct Fluorination of Organic Compounds
Abstract
The synthesis of perfluoro organic compounds by direct fluorination has been studied. The compounds studied included: ortho-toluic acid, meta-toluic acid, para-toluic acid, sodium acetate, diglycolic acid, diphenyl ether, 2- ethoxyethylacetate, 3-oxoglutaric acid, 2-oxoglutaric acid, methoxyasetic acid, methoxyphenoxyacetic acid, diethyl carbonate, malonic acid, adipic acid. These materials have been fluorinated at low concentrations of fluorine and at a variety of temperatures varying from room temperature to -78C. Invariably with extremely low fluorine con-centrations, the resulting products contained very little fluorinated material as evidenced by their infrared spectra. Under longer reaction times and/or higher fluorine concentrations, the materials tended to be degraded into low molecular weight volatiles. Polyethylene has been surface fluorinated and the kinetics of the process have been studied from 25 to 50 C. The rate of constants for each temperature and the activation energy of the process are reported. Natural rubber samples were surface treated with fluorine and appear to survive acceptably with a subsequent lowering of surface energy. Matrix isolation studies of organic molecules in fluorine matrices are also reported. The species studied were methane, ethane, ethylene, acetylene, and formic acid. It was found that fluorine molecules at 4-15 K behaved essentially like an inert substrate, but fluorine atoms, prepared in situ by photolysis, are very reactive and lead to various fluorinated derivatives.
Document Details
- Document Type
- Technical Report
- Publication Date
- Feb 01, 1972
- Accession Number
- AD0894598
Entities
People
- A. P. Conroy
- F. D. Catrett
- J. J. Wang
- John L. Margrave
- R. B. Badachhape
Organizations
- Rice University