Ethylene fluoride

ETHYLENE FLUORIDE (75-37-6) Flammable gas (flammability limits 3.7-18% by volume in air). Violent reaction with strong oxidizers, barium, sodium, and potassium. Incompatible with powdered aluminum, liquid oxygen, potassium,. sodium. May form explosive compounds with divalent light metals and metallic azides. Attacks some metals in the presence of moisture. Undergoes thermal decomposition when exposed to flame or red-hot surfaces. Flow or agitation of substance may generate electrostatic charges due to low conductivity. 

CAS 75-37-6 EINECS/ELINCS 200-866-1 Synonyms DIfluoroethane Ethylene fluoride Ethylidene fluoride Fluorocarbon 152a Halocarbon 152a... 

Ethylene fluoride. See 1,1-Difluoroethane Ethylene formate. See Ethylene glycol diformate Ethylene glycol... 

Alkyl fluorides may be prepared in moderate yield by interaction of an alkyl bromide with anhydrous potassium fluoride in the presence of dry ethylene glycol as a solvent for the inorganic fluoride, for example ... 

In a dry 500 ml. three-necked fiask, equipped with a mercury-sealed stirrer, a 100 ml. dropping funnel and a short fractionating column (1), place a mixture of 116 g. of anhydrous, finely-powered potassium fluoride (2) and 200 g. of dry ethylene glycol (3). Connect the fractionating... 

Redistil laboratory grade ethylene glycol under reduced pressure and collect the fraction of b.p. 85-90°/7 mm. for use as a solvent for the potassium fluoride. 

Chapter III. 1 Heptene (111,10) alkyl iodides (KI H3PO4 method) (111,38) alkyl fluorides (KF-ethylene glycol method) (111,41) keten (nichrome wire method) (111,90) ion exchange resin catalyst method for esters (111,102) acetamide (urea method) (111,107) ethyl a bromopropionate (111,126) acetoacetatic ester condensation using sodium triphenylmethide (111,151). 

Fluorinated ethylene-propylene resin Poly(vinylidene fluoride) Ethylene-tetrafluoroethylene copolymer Ethylene- chlorotrifluoro- ethylene copolymer Cellulose- filled Glass-fiber- reinforced... 

Magnesium Air, beryllium fluoride, ethylene oxide, halogens, halocarbons, HI, metal cyanides, metal oxides, metal oxosalts, methanol, oxidants, peroxides, sulfur, tellurium... 

TFE copolymers pLUORINE COMPOUNDS, ORGANIC - TETRAFLUOROETHYLENE-ETHYLENE COPOLYTffiRS] (Vol 11) -vinyl fluoride from pLUORINE COMPOUNDS, ORGANIC - POLY(VINYL FLUORIDE)] (Vol 11)... 

Perfluorinated ethylene—propylene copolymers, Tetrafluoroethylene—ethylene copolymers, Tetrafluoroethylene—perfluorovinyl ether copolymers, Poly(vinyl fluoride),... 

Another use of hydrogen fluoride, although not in halogen exchange, is the reaction with ethylenes or acetylenes to form the addition products, 1,1-difluoroethane [75-37-6] and vinyl fluoride [75-02-5]-. 

In 1954 the surface fluorination of polyethylene sheets by using a soHd CO2 cooled heat sink was patented (44). Later patents covered the fluorination of PVC (45) and polyethylene bottles (46). Studies of surface fluorination of polymer films have been reported (47). The fluorination of polyethylene powder was described (48) as a fiery intense reaction, which was finally controlled by dilution with an inert gas at reduced pressures. Direct fluorination of polymers was achieved in 1970 (8,49). More recently, surface fluorinations of poly(vinyl fluoride), polycarbonates, polystyrene, and poly(methyl methacrylate), and the surface fluorination of containers have been described (50,51). Partially fluorinated poly(ethylene terephthalate) and polyamides such as nylon have excellent soil release properties as well as high wettabiUty (52,53). The most advanced direct fluorination technology in the area of single-compound synthesis and synthesis of high performance fluids is currently practiced by 3M Co. of St. Paul, Minnesota, and by Exfluor Research Corp. of Austin, Texas. 

Difluoropyridines. 2,4-Difluoropyridine can be prepared (26% yield) from 2,4-dichloropyridine and potassium fluoride in sulfolane and ethylene glycol initiator (403). The 4-fluorine is preferentially replaced by oxygen nucleophiles to give 2-fluoro-4-hydroxypyridine derivatives for herbicidal apphcations (404). 

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. 

The equimolar copolymer of ethylene and tetrafluoroethylene is isomeric with poly(vinyhdene fluoride) but has a higher melting point (16,17) and a lower dielectric loss (18,19) (see Fluorine compounds, organic-poly(VINYLIDENE fluoride)). A copolymer with the degree of alternation of about 0.88 was used to study the stmcture (20). Its unit cell was determined by x-ray diffraction. Despite irregularities in the chain stmcture and low crystallinity, a unit cell and stmcture was derived that gave a calculated crystalline density of 1.9 g/cm. The unit cell is befleved to be orthorhombic or monoclinic (a = 0.96 nm, b = 0.925 nm, c = 0.50 nm 7 = 96%. 

Vlayl fluoride [75-02-5] (VF) (fluoroethene) is a colorless gas at ambient conditions. It was first prepared by reaction of l,l-difluoro-2-bromoethane [359-07-9] with ziac (1). Most approaches to vinyl fluoride synthesis have employed reactions of acetylene [74-86-2] with hydrogen fluoride (HF) either directly (2—5) or utilizing catalysts (3,6—10). Other routes have iavolved ethylene [74-85-1] and HF (11), pyrolysis of 1,1-difluoroethane [624-72-6] (12,13) and fluorochloroethanes (14—18), reaction of 1,1-difluoroethane with acetylene (19,20), and halogen exchange of vinyl chloride [75-01-4] with HF (21—23). Physical properties of vinyl fluoride are given ia Table 1. 

Copolymers of VF and a wide variety of other monomers have been prepared (6,41—48). The high energy of the propagating vinyl fluoride radical strongly influences the course of these polymerizations. VF incorporates well with other monomers that do not produce stable free radicals, such as ethylene and vinyl acetate, but is sparingly incorporated with more stable radicals such as acrylonitrile [107-13-1] and vinyl chloride. An Alfrey-Price value of 0.010 0.005 and an e value of 0.8 0.2 have been determined (49). The low value of is consistent with titde resonance stability and the e value is suggestive of an electron-rich monomer. 

Many cellular plastics that have not reached significant commercial use have been introduced or their manufacture described in Hterature. Examples of such polymers are chlorinated or chlorosulfonated polyethylene, a copolymer of vinyUdene fluoride and hexafluoropropylene, polyamides (4), polytetrafluoroethylene (5), styrene—acrylonitrile copolymers (6,7), polyimides (8), and ethylene—propylene copolymers (9). 

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