L,2-Epoxy-3-phenoxypropane

SYNS l,2-EPOXY-3-PHENOXYPROPANE 2,3-EPOXYPROPYLPHENYL ETHER FENYL-GLYCIDYLETHER (CZECH) GLYCIDYL PHENYL ETHER PGE PHENOL-GLYCIDAETHER (GERMAN)... 

Hydrogen halides Acetamide. Ammonium acetate. Ammonium formate. Epichloro-hydrin. l,2-Epoxy-3-phenoxypropane. Ethylenediamine. Ethylene oxide. Magnesium oxide. Propylene oxide. 

The reaction between the epoxy and the end groups of the polyester was modeled by using l,2-epoxy-3-phenoxypropane and n-octanoic acid. An equimolar solution of the two was prepared in tetrahydrofuran (THF) with a catalytic amount of pyridine a few drops of this solution were placed on a NaCl window and the THF allowed to evaporate. The reaction was carried out at 100 °C, and the IR spectrum of the mixture was recorded every 15 min. Similar experiments were performed without a catalyst. The reaction between... 

Figure 2. Infrared spectrum of a mixture of l,2-epoxy-3-phenoxypropane and n-octanoic acid at 100 °C as a function of time, showing the rapid disappearance of acid carbonyl absorption in the presence of pyridine as a catalyst.

In the preparation of 2-phenoxymethylperhydro-imidazo[l, 2-a]pyridine (221), the ring opening of l,2-epoxy-3-phenoxypropane (219) with 2-aminopyridine followed by catalytic reduction of the hydrochloride of the resultant amino alcohol over Rh/C gave 220. Treatment of220 with thionyl chloride followed by base produced the required 221 (70IJC707). 

SYNONYMS l,2-epoxy-3-phenoxypropane, 2,3-epoxypropylphenyl ether, glycidyl phenyl ether, pge, phenoxy methyloxirane, phenyl-2,3-epoxypropyl ether. 

Di( 1-prop yll) ether Di(2-propynyl) ether Di n propo methane l,2 Epoxy-3-isopropoxy propane l,2 Epoxy-3-phenoxypropane Ethoxyacetophenone... 

Prepreg of 2,2 -propylidene-bis(l, 2-epoxy-3-phenoxypropane) polymerized with 0.2 moles of l,2-epoxy-3-phenoxypropane-(l-methylidene)-l,4-phenylene-oxy(2-propanol)... 

The hypothesis of the existence of a pure ionic mechanism, involving species such as CgHjO or CgHjCOO in the reaction of epoxy with either phenol or benzoic acid, has been mentioned in the earliest publications relating to this reaction Shechter et al. studying the reaction between l,2-epoxy-3-phenoxypropane and octanoic acid in the presence of a basic catalyst (KOH or benzyldimethylamine), proposed an ionic mechanism with the carboxylate ion as active species. However, their hypothesis has no fundamental kinetic grounds. 

Some authors have denied the existence of mechanisms involving only ionic or only complex forms. Thus, Fiala and Lidarik studied the benzyldimethylamine-catalyzed reaction of 1,2-epoxy-3-benzoatepropane with benzoic acid in xylene. The order in acid, epoxide, and catalyst are 0.5,1, and 0.6, respectively. Like Kakiuchi and Tanaka for l,2-epoxy-3-phenoxypropane/benzoic acid systems, they found that the relation log k = a log D + b (where D is the dielectric constant of the system)... 

Kakiuchi and Tanakaextended this study to several substituted acids and l,2-epoxy-3-phenoxypropane. In addition to reactions (44) to (46), they took into consideration the following ... 

Tanaka interestingly discussed the factors which influence the stereochemistry of the transition-state species IV for the reaction of benzoic acid with l,2-epoxy-3-phenoxypropane catalyzed by substituted pyridines in xylene. As in Ref. it was shown that reaction (47) to (SO) do not take place and that the kinetics is second order with respect to acid and epoxide. The plot of the rate constant k against [Cat] is a straight line which does not pass through the origin ... 

Using infra-red spectra analysis, Pirozhnaya and Gromov claimed that the formation of complex IV is not sufficient to explain the kinetics of the tertiary amine-catalyzed reaction of butanoic acid with l,2-epoxy-3-phenoxypropane. According to them, aromatic and aliphatic tertiary amines have similar kinetic activity, but differ greatly in their ability to form complexes with butanoic add. 

Madec and Mar6chal i i i studied the system N,N-dimethyIdodecylamine/ benzoic acid/l,2-epoxy-3-phenoxypropane in different solvents. They confirmed the formation of a cyclic complex and, at the same time, they showed that a side reaction contributes to the general kinetic pattern. This will be developed in Sect. 4.2.4. 

Studying the reaction of substituted l,2-epoxy-3-phenoxypropane with benzoic acid in the presence of a tertiary amine, Kakiuchi and Tanaka reported Hammett s plots obtained in solvents such as xylene, mono- and dichlorobenzene, and nitrobenzene. They obtained the following values of g ... 

F%. 1. Isokinetic rdationship in the reaction of l,2-epoxy-3-phenoxypropane and benzoic acid with dimethyldodecylaniine in xylene. Symbols are R from RC H40CH2< I H2" ... 

Kakiuchi and Endo studied the influence of the nature of the solvent on the pyridine-catalyzed reaction of benzoic acid with l,2-epoxy-3-phenoxypropane. The reaction is first order for acid, epoxide, and catalyst it was carried out in toluene-nitrobenzene and in toluene-dioxane mixtures as well as in different pure solvents. The dielectric constant was measured before the reaction started and after the reaction stopped it was noted that this constant hardly changes during the course of the reaction. A linear relationship between log q and D was dbserved in toluene-nitrobenzene, but not in dioxane-nitrobenzene according to the authors, this could be due to a specific solvating effect of dioxane. 

Madec and Marechal i ) discussed the influence of the nature of the solvent on the reaction rate of the main and of one of the side reactions in the N,N-dimethyl-dodecylamine-catalyzed reaction of benzoic acid with l,2-epoxy-3-phenoxypropane their results are discussed in Sect. 4.2.4. 

Sorokin and Gershanova analyzed the system hexanoic add/l,2-epoxy-3-phenoxypropane/MeOH, where Me is an alkaline metal (K or Na). The true catalyst is obviously RCOOMe. They found the following kinetic relation ... 

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