1.2- Epoxy-3-phenoxypropane

The conversion of dextran with 1,2-epoxy-3-phenoxypropane, epoxyoctane or epoxydodecane may be exploited for the preparation of amphiphilic dextran derivatives. Polymeric surfactants prepared by hydrophobic modification of polysaccharides have been widely studied, starting with the pioneering work of Landoll [261]. Neutral water-soluble polymeric surfactants can be obtained by reaction of dextran with 1,2-epoxy-3-phenoxypropane in 1 M aqueous NaOH at ambient temperature (Fig. 35, [229,233]). The number n of hydrophobic groups per 100 Glcp units varies between 7 and 22 depending on the reaction conditions. 2-Hydroxy-3-phenoxy propyl dextran ethers (DexP) behave like classical associative polymers in aqueous solution. In dilute solution, the intrinsic viscosity decreases significantly whereas... 

In the preparation of 2-phenoxymethylperhydro-imidazo[l, 2-a]pyridine (221), the ring opening of 1,2-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). 

The poiyether poiy(bisphenol F digiycidyi ether) shows a weight ioss as low as 80° C in NaOH [23]. Some other poiyethers are described in literature, such as poly[bis(2,3-epoxy-cyclopentyl)ether], poly(1,4-butandioi digiycidyi ether), poly(phenyl glycidyi ether), poly(1,2-epoxy-3-phenoxypropane), etc. The structures of the main sequence of these poiymers after curing are shown beiow ... 

CAS 122-60-1 EINECS/ELINCS 204-557-2 Synonyms 1,2-Epoxy-3-phenoxypropane 2,3-Epoxypropyl phenyl ether Glicidyl phenyl ether Glycidyl phenyl ether Oxirane, (phenoxymethyl)- PGE Phenol glycidyl ether 3-Phenoxy-1,2-epoxypropane Phenoxy-propene oxide Phenoxypropylene oxide Phenyl-2,3-epoxypropyl ether Classification Aromatic epoxy ether Empirical C5FI10O2... 

A global analysis of the kinetic results relative to the model reactions of benzoic acid with 1,2-epoxy-3-phenoxypropane in solution and of octadecanoic acid... 

Several mechanisms have been proposed, but very few authors have shown that the orders in reactants depend on the nature of the reaction medium, although Madec and Mar6chal, studying the benzoic/1,2-epoxy-3-phenoxypropane system found that the overall order is 2 in xylene, chlorobenzene, and orthodichlorobenzene as solvent the authors suggested a bimolecular process. However, compared to the amine-catalyzed reaction, the reaction is very slow. 

Such pure ionic mechanisms have been severely criticized by several authors. Thus, Ishii et al. studying the reaction of various substituted benzoic acids with 1,2-epoxy-3-phenoxypropane in the presence of NMcj, determined values of Hammett s plot. They observed that q is positive and decreases with increasing reaction temperature. According to these authors, this shows that ionic dissociation of benzoic acid is not the rate-controlling factor, since q values relative to the dissociation constant of substituted benzoic acid do not change with temperature Even if Ishii s comments about the values of q are not clear, his experimental observations fit those of Kakiuchi and Tanaka... 

Sorokin and Gershanova carried out a kinetic study of hexanoic acid with various epoxy compounds 1,2-epoxy-3-phenoxypropane and various substituted derivatives, 1,2-epoxy-3-allyloxypropane, l,2-epoxy-3-hydroxypr( ane. Th found a zero order in add and first order in epoxy and catalyst, respectively. 

Sakai et al. proposed the following mechanism for the base-catalyzed reaction of 1,2-epoxy-3-phenoxypropane with benzoic add in non-polar solvents ... 

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