Diphenyl oxidation

Brominated Diphenyl Oxides. Brominated diphenyl oxides are prepared by the bromination of diphenyl oxide. They are often referred to as diphenyl ethers. Taken together, the class constitutes the largest volume of brominated flame retardants. They range ia properties from high melting sohds to hquids. They are used, as additives, ia virtually every polymer system. 

DecabromodiphenylOxide. Decabromodiphenyl oxide [1163-19-5] (decabrom) is the largest volume bromiaated flame retardant used solely as an additive. It is prepared by the bromination of diphenyl oxide ia neat bromine usiag AlCl as a catalyst (32). The bromination may also be carried out ia an iaert solvent such as methylene dibromide [74-95-3] (33). The commercially available grades are >98% decabromodiphenyl oxide with the remainder being the nonabromo species. 

Octabromodiphenyl Oxide. Octabromodiphenyl oxide [32536-52-0] (OBDPO) is prepared by bromination of diphenyl oxide. The degree of bromination is controlled either through stoichiometry (34) or through control of the reaction kinetics (35). The melting poiat and the composition of the commercial products vary somewhat. OBDPO is used primarily ia ABS resias where it offers a good balance of physical properties. Poor uv stabiUty is the primary drawback and use ia ABS is being supplanted by other brominated flame retardants, primarily TBBPA. 

Pentabromodiphenyl Oxide. Pentabromodiphenyl oxide [32534-81-9] (PBDPO) is prepared from diphenyl oxide by bromiaation (36). It is primarily used as a flame retardant for flexible polyurethane foams. For this appHcation PBDPO is sold as a blend with a triaryl phosphate. Its primary benefit ia flexible polyurethanes is superior thermal stabiUty, ie, scorch resistance, compared to chloroalkyl phosphates (see Phosphate esters). 

Dowtherm LE is a mixture of diphenyl oxide and methylated biphenyl for use in Hquid-phase systems. The low crystal point and low viscosity obviate protection from freezing at temperatures down to —30°C. 

Biphenyl, terphenyl, and their alkyl or hydrogenated derivatives generally serve markets where price and performance, rather than composition, is the customer s primary concern. Performance standards for heat-transfer appHcations are usually set by the fluid suppHer. The biphenyl—diphenyl oxide eutectic (26.5% biphenyl, 73.5% DPO) represents a special case. This composition has become a widely recogni2ed standard vapor-phase heat-transfer medium. It is sold throughout the world under various trademarks. In the United States, Dow (Dowtherm A) and Monsanto (Therminol VP-1) are the primary suppHers. Alkylated biphenyls and partially hydrogenated terphenyls serving the dielectric and carbonless copy paper dye solvent markets likewise are sold primarily on the basis of price and performance characteristics jointly agreed on by producer and user. 

Condensing Organic Va.por, The eutectic mixture of diphenyl and diphenyl oxide is an excellent vapor medium for precise temperature control at temperatures higher than those practical using steam. This mixture can achieve 315°C while holding pressure at 304 kPa (3 atm) absolute. In contrast, steam would require 10.6 MPa (105 atm) pressure. 

Benzo[c]thiophene, 1,3-diphenyl-oxidative ring opening, 4, 768 synthesis, 4, 141-142... 

Imidazoline-2-thione, 4,5-diphenyl-oxidation, 5, 405, 445 Imidazoline-2-thione, 4-methyl-Mannich reaction, S, 405 oxidation, 5, 445... 

Chlorinated camphene (toxaphene) Chlorinated diphenyl oxide Chlorine... 

Chlorinated camphene Chlorinated diphenyl oxide Chlorine Chlorine dioxide Chlorine trifluoride Chloroacetaldehyde... 

Chemical Designations - Synonyms Phenyl Ether Diphenyl Oxide Phenoxybenzene Chemical Formula C HjOCuH. ... 

Diphenyl dichlorosilane, 59 Diphenyl oxide, 59 Diphenylamine, 58 1,2-DiphenyUiydrazine, 59 DIPLAST , phthalates, 59 Dipropyl ketone, 59 Dipropylamine, 59 Dipropylene glycol methyl ether, 59 Diquat, 59... 

On the other hand, Davies5 , studying the reaction of adipic add with 1,5-pentanediol in diphenyl oxide or diethylaniline found an order increasing slowly from two with conversion. From this result he concluded that Flory s1,252-254> and Hinshelwood s240,241 interpretations are erroneous. Two remarks must be made about the works of Davies5 experimental errors relative to titrations are rather high and kinetic laws are established for conversions below 50%. Under such conditions the accuracy of experimental determinations of orders is rather poor. 

Several results were reported by Russian authors. They are completely different from those reported above. Sorokin14 found an overall reaction order of 2 for the system heptanoic acid/l,2-ethanediol/diphenyl oxide. Bolotina16 studied the reaction of 2-ethylhexyl hydrogenphthalate with 2-ethylhexanol in the corresponding diester and found an order of 1 with respect to acid and of 2 with respect to alcohol. 

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