Carbonyl fluorides

Carbonyl fluoride, COF2, and oxygen difluoride react in the presence of cesium fluoride catalyst to give bis(trifluorylmethyl)trioxide [1718-18-9] CF OOOCF (31). CF OOF has been isolated from the reaction in the presence of excess OF2 (32). 

Tetrafluoroethylene undergoes addition reactions typical of an olefin. It bums in air to form carbon tetrafluoride, carbonyl fluoride, and carbon dioxide (24). Under controlled conditions, oxygenation produces an epoxide (25) or an explosive polymeric peroxide (24). Trifluorovinyl ethers,... 

Uses. Besides polymerizing TFE to various types of high PTEE homopolymer, TEE is copolymerized with hexafluoropropylene (29), ethylene (30), perfluorinated ether (31), isobutylene (32), propylene (33), and in some cases it is used as a termonomer (34). It is used to prepare low molecular weight polyfluorocarbons (35) and carbonyl fluoride (36), as well as to form PTEE m situ on metal surfaces (37). Hexafluoropropylene [116-15-4] (38,39), perfluorinated ethers, and other oligomers are prepared from TEE. 

Preparation of Arylcarboxylic Acids and Derivatives. The general Friedel-Crafts acylation principle can be successfully appHed to the preparation of aromatic carboxyUc acids. Carbonyl haUdes (phosgene, carbonyl chloride fluoride, or carbonyl fluoride) [353-50-4] are diacyl haUdes of carbonic acid. Phosgene [75-44-5] or oxalyl chloride [79-37-8] react with aromatic hydrocarbons to give aroyl chlorides that yield acids on hydrolysis (133) ... 

CARBON OXYFLUORIDE see CARBONYL FLUORIDE CARBON REMOVER, LIQUID CARBON TETRABROMIDE CARBON TETRACHLORIDE... 

CARBON TETRAFLUORIDE CARBONYL FLUORIDE CARBONYL SULFIDE CARBOPHENOTHION CARVONE... 

Although fluonnation of peroxoanions [S2] has been examined, the major emphasis in the fluonnation of oxygenated material is the preparation offhioroxy compounds The simplest, trifluoromethyl hypofluorite, can be prepared almost quantitatively by the action of fluorine on carbonyl fluoride (fluorophosgene) in the presence of various catalysts [Si, 84] Addition of fluorine to trifluoroacetic acid [S5] or its sodium salt [S6] gives rise to FjCF(OF)2 Long-chain fluoroxy compounds can also... 

In addition, fluonne [97, 98], trifluoromethyl hypofluorite [99, 100], bisftri-fluoromethyOperoxide [100, 101], trifluoromethyl disulfide [100]. and xenon difluoride [102, lOi, 104] react with phosphines to give the corresponding diflu-orophosphoranes in yields ranging from 25% to near quantitative. Phosphites are fluorinated by carbonyl fluoride [95, 96] or 2-hydroperfIuoropropyl azide [f05J (equation 15). 

Thermal decomposition is a major route to smaller perfluonnated molecules Tetrafluoroethylene pyrolyzed at 1100-1300 °C with carbon dioxide gives a mixture of tetrafluoromethane (19 9%), hexafluoroethane (61 3%), and carbonyl fluoride (18 6%) [87]... 

Carbonyl fluoride, COF2, is an important intermediate for organic fluorine compounds. It can be prepared by the following reaction ... 

Carbonyl fluoride C F T Steel, stainless steel, copper or brass for dry gas. Monel, copper or nickel for moist gas ... 

C NMR Data. Some typical carbon NMR data are given in Scheme 3.73 for acid fluorides and for carbonyl fluoride. 

Reaction to give tetrafluorooxathietane 2,2-dioxide (tetrafluoroethane sultone) had been used industrially and uneventfully, but reaction with excess sulfur trioxide may cause explosive decomposition to carbonyl fluoride and sulfur dioxide [1]. An incident involving the same explosion hazard was reported 11 years later [2], Use of inert gas to prevent explosion has been patented [3],... 

Treatment of these samples with SF4 gas to convert the carboxylic acids produced in the weathering process into carbonyl fluorides showed [2, 11] that the acids are actually a mixture of aliphatic and aromatic acids (Figure 18.12). Aromatic acid species are by far the predominant ones, however. The origin of these acids will be discussed below in conjunction with the overall mechanisms of photodegradation. Aliphatic acid species were detected by GC/MS in the artificial device exposure of PECT [11], Note that the PECT copolymer produced more aromatic acids with the same exposure as PET but that the aliphatic acid production was several times higher for the PECT copolymer. The photo-oxidation of the co-glycol must be the reason for this difference. 

A liquid perfluorocarbon was being used as solvent in an oxidation by oxygen under pressure more energy was released than expected [1], It is cautioned that fluorocarbons are not inert to oxidation, presumably to carbonyl fluoride. An explosion has been experienced with perfluorotoluene in like circumstances [2], A correspondent reports that perfluorotoluene is flammable in air, more saturated perfluorocarbons in pure oxygen [3], Another detailed the combustion performance of polytetrafluoroethylene 148 kcal/mole ignition temperature not below 465°C at 7000 psi of oxygen [4], the product is mostly carbonyl fluoride. Other oxidants may also present a risk in extreme circumstances. 

---